WO2014002109A1 - Substituted tetrazole compounds and process thereof - Google Patents

Substituted tetrazole compounds and process thereof Download PDF

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Publication number
WO2014002109A1
WO2014002109A1 PCT/IN2013/000250 IN2013000250W WO2014002109A1 WO 2014002109 A1 WO2014002109 A1 WO 2014002109A1 IN 2013000250 W IN2013000250 W IN 2013000250W WO 2014002109 A1 WO2014002109 A1 WO 2014002109A1
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WIPO (PCT)
Prior art keywords
pyrazol
tetrazole
chloro
bromo
iodo
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PCT/IN2013/000250
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French (fr)
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WO2014002109A4 (en
Inventor
Sanjay Sambhajirao PALIMKAR
Jivan Dhanraj PAWAR
B Sankar
Subhash Rajaram Kadam
Rama Mohan HINDUPUR
Venkatesh M. PRABHU
Hari Narayan PATI
Vadiraj Gopinath SUPHALA
Avinash Sheshrao MANE
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Rallis India Limited
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Publication of WO2014002109A4 publication Critical patent/WO2014002109A4/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present disclosure relates to substituted tetrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof, which are useful as intermediates in the preparation of herbicidal sulfonamide or sulfonyl urea growth regulators or herbicides.
  • the present disclosure also relates to methods for the preparation of such intermediates.
  • Sulfonamide or sulfonyl urea growth regulators or herbicides are a more recent class of chemical compounds that function by inhibiting the action of a plant enzyme, stopping plant growth, and ev entually killing the plant. These are well known as being highly beneficial for controlling undesirable vegetation in agronomically desirable crops.
  • EP0204513 B l which is incorporated in . its entirety by reference, describes a method for preparation of such sulfonylureas and sulfonylthioureas herbicide from sulfonyl isocyanate or isocyanate intermediates with an appropriate heterocyclic amines.
  • the patent document further discloses the preparation of sulfonyl isocyanate intermediates by reacting appropriate sulfonamide with phosgene in presence of n-butyl isocyanate and 1 ,4- diazabicyclo[2.2.2]octane.
  • sulfonyl thioisocyanates are reported to be prepared by reacting sulfonamides with carbon disulphide and potassium hydroxide to form corresponding dipotassium salt which on treatment with phosgene provides isothiocyanate intermediates.
  • the patent US4650892 discloses a process of preparation of sulfonamide herbicides using aromatic sulfonyl chlorides and sulfonamides.
  • sulfonamide herbicides One type of sulfonamide herbicides is Azimsulfuron or N-[[(4,6-dimethoxy-2- pyrimidinyl)amino]carbonyl]- l-methyl-4-(2-methyl-2H-tetrazol-5-yl)- l H-pyrazole ⁇ - sulfonamide, which is well known and has been found to be particularly useful as post emergent herbicides when used against sensitive weeds.
  • Azimsulfuron affects sensitive weeds through inhibition of the enzyme acetolactate synthase (ALS).
  • the present disclosure relates to substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I
  • Ri is selected from H, CI, Br or I;
  • R 2 is selected from hydrogen or a straight chain or a branched C
  • R3 is selected from a straight or a branched chain Ci_ 7 alkyl; or a aryl group;
  • straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl;
  • said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C alkyl, phenyl, or a C1 -C4 alkoxy;
  • the present disclosure further provides a process for preparing substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof of formula I.
  • Halo' ' or Halogen alone or in combination with any other term means halogens such as chloro (CI), bromo (Br), fluoro (F) and iodo (1).
  • Ci- 7 alkyl refers to a monoradical branched or unbranched saturated hydrocarbon chain having 1 , 2, 3, 4, 5, 6 or 7 carbon atoms. This term is exemplified by groups such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl, n-hexyl, n- heptyl, and the like which optionally carries one or more substituents, preferably one to two, each independently selected from CI, Br, F, I,. N0 2 , CN, C1 -5 alkyl, phenyl or a C1 -C4 alkoxy.
  • C6-C14 aryl refers to an aromatic carbocyclic group of 6 to 14 carbon atoms having a single ring (e.g. phenyl) or multiple rings (e.g. biphenyl), or multiple condensed (fused) rings (e.g. naphthyl or anthranyl).
  • Preferred aryls include phenyl, naphthyl and the like which optionally carries one or more substituents, preferably one to two, each independently selected from CI, Br, F, I, C
  • the compounds described herein may contain one or more chiral centers and/or double bonds and therefore, may exist as stereo-isomers, such as geometric isomers, enantiomers or diastereomers. Accordingly, the chemical structures depicted herein encompass all possible enantiomers and stereo-isomers of the illustrated or identified compounds including stereoisomerically pure forms (e.g., geometrically pure, enantiomerically pure or diastereomerically pure) and enantiomeric and stereoisomeric mixtures. Enantiomeric ' and stereoisomeric mixtures can be resolved into their component enantiomers or stereo-isomers using separation techniques or chiral synthesis techniques well known to the person skilled in the art. The compounds may also exist in several tautomeric forms including the enol form, the keto form and mixtures thereof. Accordingly, the chemical structures depicted herein encompass all possible tautomeric forms of the illustrated or identified compounds.
  • the present disclosure provides substituted tetrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof, which are useful as intermediates in the preparation of herbicidal sulfonamide. Accordingly, the present disclosure provides substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I
  • Ri is selected from H, CI, Br or I ;
  • R.2 is selected from hydrogen or a straight chain or a branched C
  • R3 is selected from a straight or a branched chain C] _ 7 alkyl; or a C 6 -C 14 aryl group;
  • straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, 1, or phenyl;
  • said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, J, C1.5 alkyl, phenyl, or a Q -C4 alkoxy;
  • An embodiment of the present disclosure provides substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula 1
  • Ri is selected from H, CI, Br or I;
  • R 2 is selected from hydrogen or a straight chain or a branched C 1 -3 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from Br, N0 2 , CN, C i -5 alkyl, or a C 1 -C4 alkoxy; and
  • R3 is selected from a straight or a branched chain C 1.4 alkyl; or a C 6 aryl group,
  • straight or branched chain alkyl is optionally substituted with a phenyl group
  • said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, C i -2 alkyl, or a C 1 -C4 alkoxy;
  • Another embodiment of the present disclosure provides substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I wherein:
  • Ri is selected from CI, Br or I;
  • R 2 is selected from hydrogen or a straight chain or a branched C1.7 alkyl; wherein said alkyl is optionally substituted with phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N0 2 , CN, C
  • R 3 is selected from a straight or a branched chain C ] . 7 alkyl or a C 6 -C
  • straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI,
  • Ri is selected from CI, Br or 1;
  • R 2 is hydrogen or methyl
  • R3 is selected from a straight or a branched chain C 1 -7 alkyl; or a C6-C 14 aryl group;
  • straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl;
  • aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C1 -5 alkyl, or a C 1 -C4 alkoxy.
  • substituents independently selected from CI, Br, F, I, C1 -5 alkyl, or a C 1 -C4 alkoxy.
  • Still another embodiment of the present disclosure provides a substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I, se ected from
  • an embodiment of the present disclosure provides a substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I which are listed below.
  • the regio-isomers of compounds of formula I are also within the scope of the present disclosure, wherein the alkyl group of R 2 is in 1 or 2 position of the tetrazole ring. Certain compounds of the present disclosure is selected from

Abstract

The present disclosure provides a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, useful as intermediates in preparation of sulfonamide or sulfonyl urea growth regulators or herbicides. Formula I The present disclosure further provides a process for preparing compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof.

Description

TED TETRAZOLE COMPOUNDS AND PROCESS THEREOF
Figure imgf000003_0001
TECHNICAL FIELD
The present disclosure relates to substituted tetrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof, which are useful as intermediates in the preparation of herbicidal sulfonamide or sulfonyl urea growth regulators or herbicides.
The present disclosure also relates to methods for the preparation of such intermediates.
BACKGROUND
Sulfonamide or sulfonyl urea growth regulators or herbicides are a more recent class of chemical compounds that function by inhibiting the action of a plant enzyme, stopping plant growth, and ev entually killing the plant. These are well known as being highly beneficial for controlling undesirable vegetation in agronomically desirable crops.
The sulfonamide herbicides are reported to be prepared by various ways in the art. EP0204513 B l , which is incorporated in . its entirety by reference, describes a method for preparation of such sulfonylureas and sulfonylthioureas herbicide from sulfonyl isocyanate or isocyanate intermediates with an appropriate heterocyclic amines. The patent document further discloses the preparation of sulfonyl isocyanate intermediates by reacting appropriate sulfonamide with phosgene in presence of n-butyl isocyanate and 1 ,4- diazabicyclo[2.2.2]octane. Further, sulfonyl thioisocyanates are reported to be prepared by reacting sulfonamides with carbon disulphide and potassium hydroxide to form corresponding dipotassium salt which on treatment with phosgene provides isothiocyanate intermediates.
The patent US4650892 discloses a process of preparation of sulfonamide herbicides using aromatic sulfonyl chlorides and sulfonamides.
One type of sulfonamide herbicides is Azimsulfuron or N-[[(4,6-dimethoxy-2- pyrimidinyl)amino]carbonyl]- l-methyl-4-(2-methyl-2H-tetrazol-5-yl)- l H-pyrazole^- sulfonamide, which is well known and has been found to be particularly useful as post emergent herbicides when used against sensitive weeds. Azimsulfuron affects sensitive weeds through inhibition of the enzyme acetolactate synthase (ALS).
In view of the importance of the emerging sulfonamide or sulfonyl urea growth regulators or herbicides, there remains a need for developing new intermediates and viable processes for their synthesis that can be successfully used for the preparation of these herbicidal compounds.
SUMMARY
The present disclosure relates to substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I
Figure imgf000004_0001
Formula I
wherein:
Ri is selected from H, CI, Br or I;
R2 is selected from hydrogen or a straight chain or a branched C | _7 alky I; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C | .5 alkyl, phenyl, or a C 1 -C4 alkoxy; and
R3 is selected from a straight or a branched chain Ci_7 alkyl; or a
Figure imgf000004_0002
aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C alkyl, phenyl, or a C1 -C4 alkoxy;
with the proviso that when Ri is H; R2 is not methyl.
The present disclosure further provides a process for preparing substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof of formula I.
These and other features, aspects, and advantages of the present disclosure will become better understood with reference to the following description. This statement is provided to introduce a selection of concepts in a simplified form. This statement is not intended to identify key features or essential features of the subject matter, nor is it intended to be used to limit the scope of the subject matter.
DETAILED DESCRIPTION
Definitions In the structural formula given herein and throughout the present disclosure, the following terms have the indicated meaning, unless specifically stated otherwise.
The term "optionally substituted" as used herein means that the group in question is either unsubstituted or substituted with one or more of the substituents specified. When the group in question is substituted with more than one substituent, the substituents may be same or different.
"Halo'' or "Halogen", alone or in combination with any other term means halogens such as chloro (CI), bromo (Br), fluoro (F) and iodo (1).
The term "Ci-7 alkyl" refers to a monoradical branched or unbranched saturated hydrocarbon chain having 1 , 2, 3, 4, 5, 6 or 7 carbon atoms. This term is exemplified by groups such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl, n-hexyl, n- heptyl, and the like which optionally carries one or more substituents, preferably one to two, each independently selected from CI, Br, F, I,. N02, CN, C1 -5 alkyl, phenyl or a C1 -C4 alkoxy.
The term " C6-C14 aryl" refers to an aromatic carbocyclic group of 6 to 14 carbon atoms having a single ring (e.g. phenyl) or multiple rings (e.g. biphenyl), or multiple condensed (fused) rings (e.g. naphthyl or anthranyl). Preferred aryls include phenyl, naphthyl and the like which optionally carries one or more substituents, preferably one to two, each independently selected from CI, Br, F, I, C| _5 alkyl, phenyl or a C1 -C4 alkoxy.
The compounds described herein may contain one or more chiral centers and/or double bonds and therefore, may exist as stereo-isomers, such as geometric isomers, enantiomers or diastereomers. Accordingly, the chemical structures depicted herein encompass all possible enantiomers and stereo-isomers of the illustrated or identified compounds including stereoisomerically pure forms (e.g., geometrically pure, enantiomerically pure or diastereomerically pure) and enantiomeric and stereoisomeric mixtures. Enantiomeric' and stereoisomeric mixtures can be resolved into their component enantiomers or stereo-isomers using separation techniques or chiral synthesis techniques well known to the person skilled in the art. The compounds may also exist in several tautomeric forms including the enol form, the keto form and mixtures thereof. Accordingly, the chemical structures depicted herein encompass all possible tautomeric forms of the illustrated or identified compounds.
The present disclosure will be described more fully hereinafter. Indeed, the invention can be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. As used in the specification, and in the appended claims, the singular forms "a", "an", "the", include plural referents unless the context clearly dictates otherwise.
The present disclosure provides substituted tetrazole compounds, its derivatives, salts, stereo-isomers or regio-isomers thereof, which are useful as intermediates in the preparation of herbicidal sulfonamide. Accordingly, the present disclosure provides substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I
Figure imgf000006_0001
N Formula I
wherein:
Ri is selected from H, CI, Br or I ;
R.2 is selected from hydrogen or a straight chain or a branched C|„7 alkyl; wherein said alkyl is optionally substituted with phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C i_5 alkyl, phenyl, or a C1 -C4 alkoxy; and
R3 is selected from a straight or a branched chain C] _7 alkyl; or a C6-C 14 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, 1, or phenyl;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, J, C1.5 alkyl, phenyl, or a Q -C4 alkoxy;
with the proviso that when Ri is H; R2 is not methyl.
An embodiment of the present disclosure provides substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula 1
wherein:
Ri is selected from H, CI, Br or I;
R2 is selected from hydrogen or a straight chain or a branched C 1 -3 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from Br, N02, CN, C i-5 alkyl, or a C 1 -C4 alkoxy; and
R3 is selected from a straight or a branched chain C 1.4 alkyl; or a C6 aryl group,
wherein said straight or branched chain alkyl is optionally substituted with a phenyl group;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, C i -2 alkyl, or a C 1 -C4 alkoxy;
with the proviso that when R| is H; R2 is not methyl.
Another embodiment of the present disclosure provides substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I wherein:
Ri is selected from CI, Br or I;
R2 is selected from hydrogen or a straight chain or a branched C1.7 alkyl; wherein said alkyl is optionally substituted with phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C | _5 alkyl, phenyl, or a C1 -C4 alkoxy; and
R3 is selected from a straight or a branched chain C ] .7 alkyl or a C6-C|4 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI,
Br, F, I, Ci_5 alkyl, phenyl or a C1 -C4 alkoxy.
Yet another embodiment of the present disclosure provides substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I wherein:
Ri is selected from CI, Br or 1;
R2 is hydrogen or methyl; and
R3 is selected from a straight or a branched chain C 1 -7 alkyl; or a C6-C 14 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C1 -5 alkyl, or a C 1 -C4 alkoxy. Still another embodiment of the present disclosure provides a substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I, se ected from
5- 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
5-1 1 -ethyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
5- l -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-1 1 -benzyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
5-1 1 -phenyl- 1 H-pyrazoI-4-yl)-2H-tetrazole;
5- 1 -(2-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-1 1 -(3-chlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
5-1 1 -(4-chlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
5- l -(2,3-dichlorophenyl)- lH-pyrazol-4-y)]-2H-tetrazole;
5-, l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
5-, l -(2,5-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-' l -(2,6-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5 1 -(3,4-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
5- 1 -(3,5-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
5-; l -(2-bromophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5- l -(3-bromophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5- l -(4-bromophenyl)-l H-pyrazoI-4-yl]-2H-tetrazole;
5- l -(4-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-' l -(2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-, l -(2,3-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-, 1 -(2,4-dimethylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
5-! l -(2,5-dimethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5-, l -(2,6-dimethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5- l -(3,4-dimethylphenyl)- lH-pyraZol-4-yl]-2H-tetrazole;
5-1 l -(3,5-dimethylphenyl)-l H-pyrazol-4-yI]-2H-tetrazole;
5-, 1 -(2-ethy Ipheny 1)- 1 H-pyrazol-4-yI]-2H-tetrazole;
5- 1 -(4-ethy Ipheny I)- 1 H-pyrazol-4-yl]-2H-tetrazole;
5- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
5- l -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5- 1 -(4-methy Ipheny I)- 1 H-pyrazol-4-yl]-2H-tetrazole; 5-chloro-l -methyl- lH-pyrazo!-4-yl)-2H-tetrazole;
5-chloro-l -ethyl- 1 H-pyrazoI-4-yl)-2H-tetrazole;
5-chloro-l -(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole; l-benzyl-5-chloro-lH-pyrazol-4-yl)-2H-tetrazole;
5-chloro-l-phenyl-lH-pyrazol-4-yl)-2H-tetrazole;
- 5-chloro-l -(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-15-chloro-l -(3-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(2, 3-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(2, 4-dichlorophenyl)-lH-pyrazol-4-yI]-2H-tetrazole;- 5-chloro-l -(2, 5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro- 1 -(2,6-dichloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(3, 4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(3, 5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- l-(2-bromophenyl)-5-chlor0-lH-pyrazoI-4-yl]-2H-tetrazole;-11 -(3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2H-tetrazole;- l-(4-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(4-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;-, 5-chloro- 1 -(2-fluorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(2, 3-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(2, 4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(2, 5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro-l -(2, 6-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazoie;- 5-chloro-l -(3, 4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
5-chloro-l -(3, 5-dimethy Iphenyl)- lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro- l-(2-ethyiphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro- l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro- l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazoIe;-' 5-chloro- l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 5-chloro- l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
5-bromo-l-methyl-lH-pyrazol-4-yl)-2H-tetrazole;
5-bromo-l -ethyl- lH-pyrazol-4-yl)-2H-tetrazole;
5-bromo-l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole; -(l-benzyl-5-bromo-lH-pyrazol-4-yl)-2H-tetrazole;
-(5-bromo-l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
-[5-bromo- 1 -(2-chloropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;-[5-bromo-l-(3-chlorophenyI)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo- 1 -(2,5-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(3,4-dichlorophenyl)-lH-pyrazo!-4-yl]-2H-tetrazole;-[5-bromo-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazoIe;-[5-bromo-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo- 1 -(3-bromophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;-[5-bromo-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(2,3-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(2,5-dimethylphenyl)-lH-pyrazoI-4-yl]-2H-tetrazole;-[5-bromo-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo- 1 -(3,4-dimethy lphenyl)- 1 H-pyrazoI-4-yl]-2H-fetrazole;-[5-bromo-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-bromo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;-[5-bromo- 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;-[5-bromo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-(5-iodo-l -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
-(l-ethyl-5-iodo-lH-pyrazol-4-yl)-2H-tetrazole;
-i5-iodo-l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-(l -benzyl-5-iodo-l H-pyrazol-4-yl)-2H-tetrazole;
-[l -(2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
-[ 1 -(3-chloropheny l)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole; 5-[ 1 -(4-chlorophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
5-[ l -(2,3-dichlorophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(2,4-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(2,5-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-[ l -(2,6-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(3,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-[l -(3,5-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(2-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(3-bromophenyl)-5-iodo-l H-pyrazoI-4-yl]-2H-tetrazole;
5-[ 1 -(4-bromophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
5-[ 1 -(4-fluorophenyI)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(2-fluorophenyl)-5-iodorl H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(2,3-dimethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
5-[ l -(2,4-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-[i-(2,5-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(2,6-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-[l -(3,4-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(3,5-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(2-ethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
5-[l -(4-ethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
5-[5-iodo-l-(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-[5-iodo-l-(2-rnethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; or
5-[5-iodo-l-(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole.
Further an embodiment of the present disclosure provides a substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof, of formula I which are listed below. In accordance with the present invention, the regio-isomers of compounds of formula I are also within the scope of the present disclosure, wherein the alkyl group of R2 is in 1 or 2 position of the tetrazole ring. Certain compounds of the present disclosure is selected from
5-(l -ethyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole-
5-(l -ethyl-lH-pyrazol-4-yl)-l -methyl-2H-tetrazole;
2-methy I-5-[ 1 -(2-methy lpropy 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
l -methyl-5-[ l -(2-methylpropyl)- l H-pyrazol-4-yl]-2H-tetrazole; -(l -benzyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole;
-(l -benzyl- lH-pyrazol-4-yl)-l-methyl-2H-tetrazole;
-methyl-5-(l -phenyl- H-pyrazol-4-yl)-2H-tetrazole;
-methyl-5-( 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[l-(2-chlorophenyl)-l H-pyrazol-4-yl]-l-methyl-2H-tetrazole;-[l-(3-chlorophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[ 1 -(3-chlorophenyl)-l H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole;-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[l-(4-chlorophenyl)-lH-pyrazoI-4-yl]-l -methy l-2H-tetrazole;-[l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[ 1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;-[l-(2,4-dichlorophen l)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;-[l-(2,5-dichlorophenyl)-lH-pyrazoI-4-yl]-2-methyl-2H-tetrazole;-[l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;-[l-(2,6-dichlorophenyl)-'l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;-[ 1 -(3,4-dichloropheny 1)- 1 H-pyrazol-4-yl]-2-methy l-2H-tetrazole;-[l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;-[l-(3,5-dichlorophenyl)-lH-pyrazoI-4-yl]-2-methyl-2H-tetrazoie;-[l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;-[l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[l-(2-bromophenyl)-lH-pyrazol-4-yl]-l'-methyl-2H-tetrazole;-[l-(3-bromophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[ 1 -(3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazoIe;-[l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[l-(4-bromophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;-[ 1 -(4-fluoropheny I)- 1 H-pyrazol-4-y l]-2-methyl-2H-tetrazole;-[ 1 -(4-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;-[l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[l-(2-fluorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;-[l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[ 1 -(2,3-dimethylpheny 1)- 1 H-pyrazol-4-y I]- 1 -methy l-2H-tetrazole 5-[ l -(2,4-dimethylphenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole 5-[l -(2,4-dimethy (phenyl)- 1 H-pyrazol-4-y I]- 1 -methy 1-2 H-tetrazole 5-[l -(2,5-dimethylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole 5-[ 1 -(2,5-dimethy lpheny 1)- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole 5-[l -(2,6-dimethylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole 5-[ 1 -(2,6-d imethy lpheny 1)- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole 5-[l -(3,4-dimethylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole 5-[ 1 -(3,4-dimethylphenyl)- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole 5-[l -(3,5-dimethylphenyl)- l H-pyrazol-4-yl]-2-methyI-2H-tetrazole 5-[l -(3,5-dimethylphenyl)-l H-pyrazol-4-yl]-l-methyl-2H-tetrazole 5-[l -(2-ethylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[l -(2-ethylphenyl)-l H-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5-[l -(4-ethy lpheny 1)-1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[l -(4-ethylphenyl)-l H-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5-[ 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y l]-2-methyl-2H-tetrazole;
5-[l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-l -methy 1-2 H-tetrazole;
-methyl-5-[l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - methy l-5-[l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
- methyl-5-[l -(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
l -methyl-5-[l -(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-(5-chloro- 1 -methyl- 1 H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
-(5-chloro- 1 -methyl- 1 H-pyrazol-4-yl)-l -methyl-2H-tetrazole;
-(5-chloro-l -ethyl- l H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
-(5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)- l-methyl-2H-tetrazole;
-[5-chloro-l -(2-methylpropyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole; -[5-chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole; -( l -benzyl-5-chloro-l H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
-( 1 -benzy 1-5-chloro- 1 H-pyrazol-4-yl)- 1 -methy l-2H-tetrazole;
-(5-chloro- l -phenyl- l H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
-(5-chloro- 1 -phenyl- 1 H-pyrazol-4-y 1)- 1 -methy l-2H-tetrazole;
-[5-chloro-l -(2-chlorophenyl)- lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; -[5-chloro- l-(2-chlorophenyl)-l H-pyrazol-4-yl]-l -methy l-2H-tetrazole; 5· chloro- 3-chlorophenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5· -chloro- 3- chloropheny 1)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5· chloro- 4- chlorophenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5· chloro- 4-chlorophenyl)- l H-pyrazol-4-yl]-l -methy !-2H-tetrazole;
5· chloro- 2,3-dichlorophenyl )-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole
5-1 chloro- 2.3- dichlorophenyl )-l H-pyrazol-4-yl]-l -methyl-2H-tetrazole
5· chloro- 2.4- dichlorophenyl )- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole
5· -chloro- 2.4- dichlorophenyl )- l H-pyrazol-4-yl]- l -.methyl-2H-tetrazole
5- chloro- 2.5- dichlorophenyl )- 1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole
5- chloro- 2.5- dichlorophenyl )- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole
5- chloro- 2.6- dichlorophenyl )- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole
5· chloro- 2,6-dichlorophenyl )-lH-pyrazol-4-yl]- l -methyl-2H-tetrazole
5· chloro- 3,4-dichlorophenyl )-lH-pyrazoI-4-yl]-2-methyl-2H-tetrazole
5- chloro- 3.4- dichlorophenyl )- 1 H-pyrazol-4-y 1]- 1 -methyl-2H-tetrazole
5- chloro- 3.5- dichlorophenyl )- 1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole
5- chloro- 3,5-dichlorophenyl )- 1 H-pyrazol-4-y 1]- 1 -methyl-2H-tetrazole
5- (2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-methyl-2H-tetrazo!e;
5- (2-bromophenyl)-5-chloro- 1 H-pyrazol-4-y I]- 1 -methy l-2H-tetrazole;
5-1 (3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- (3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5- (4-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- (4-bromophenyl)-5-chloro- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5- chloro- l -(4-fluorophenyl)- l H-pyrazol-4-yl]-2-methyi-2H-tetrazole;
•5- chloro-l -(4-fluorophenyl)- l H-pyrazol-4-yl]-i-methyl-2H-tetrazole;
5- chloro- 1 -(2-fluorophenyl)- 1 H-pyrazol-4-y l]-2-methyl-2H-tetrazole;
5· chloro- 1 -(2-fluorophenyl)- 1 H-pyrazol-4-y 1]- 1 -methy 1-2 H-tetrazole;
5- chloro- l -(2,3-dimethylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- chloro- l-(2,3-dimethylphenyl)- l H-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- chloro- 1 -(2,4-dimethylphenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- chloro- 1 -(2,4-dimethylphenyl)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5· chloro- 1 -(2, 5-dimethylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- chloro- l -(2,5-dimethylphenyl)-l H-pyrazol-4-yl]- l -methy l-2H-tetrazole;
5- chloro- 1 -(2, 6-dimethylphenyl)- lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-chloro- l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-chloro- l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-chloro- l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-chloro- l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-chloro- l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-chloro- l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-chloro- l-(2-ethylphenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-chloro- 1 -(4-ethy Iphenyl)- 1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-chloro- l-(4-ethylphenyl)-l H-pyrazoI-4-yl]-l-methyl-2H-tetrazole; 5-chloro- l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-chloro- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole; 5-chloro- l-(2-methylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-chloro- 1 -(2-methy Iphenyl)- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole; 5-chloro- l-(4-methylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-chloro- l-(4-methylphenyl)-l H-pyrazo!-4-yl]-l-methyl-2H-tetrazole; 5-bromo- 1 -methyl- 1 H-pyrazol-4-yl)-2-methy l-2H-tetrazole;
5-bromo- 1 -methy 1-1 H-pyrazol-4-yl)-l-methyl-2H-tetrazole;
5-bromo- 1 -ethyl- 1 H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5-bromo- 1 -ethyl- lH-pyrazol-4-yl)-l -methy l-2H-tetrazole;
5-bromo- l-(2-methylpropyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; ' 5-bromo- 1 -(2-methy lpropyl)-l H-pyrazol-4-yl]- 1 -methyl-2H-tetrazoIe;
1 -benzyl- 5-bromo-lH-pyrazol-4-yl)-2-methyl-2H-tetrazole;
1-benzyl- 5-bromo-lH-pyrazol-4-yl)-l -methy l-2H-tetrazole;
' 5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)-2-methy l-2H-tetrazole;
' 5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 -methyl-2H-tetrazole;
- 5-bromo- l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- 5-bromo- 1 -(2-ch loropheny I)- 1 H-py razol-4-y 1]- 1 -methy l-2H-tetrazole ;- 5-bromo- l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- 5-bromo- 1 -(3-chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole;- 5-bromo- l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- 5-bromo- 1 -(4-ch loropheny 1)- 1 H-pyrazol-4-y 1]- 1 -methyl-2H-tetrazole;- 5-bromo- 1 -(2,3-dichlorophenyl)- 1 H-pyrazoi-4-yl]-2-methyl-2H-tetrazole;
5-bromo- 1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole; 5- [5 -bromo- -(2,4-dichlorophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(2,4-dichlorophenyl)- lH-pyrazol-4-yl]- l-methyl-2H-tetrazole;
5- [5 -bromo- -(2,5-dichlorophenyl)- H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(2,5-dichloropheny 1)- 1 H-pyrazol-4-yl]- 1 -methy !-2H-tetrazole;
5- [5 -bromo- -(2,6-dichlorophenyl)- l H-pyraz0l-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(2,6-dichlorophenyl)- 1 H-pyrazol-4-y I]- 1 -methy l-2H-tetrazole;
5- [5 -bromo- -(3,4-dichlorophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(3,4-dichlorophenyl)-l H-pyrazol-4-yI]- l -methy I-2H-tetrazole;
5- [5 -bromo- -(3,5-dichlorophenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(3,5-dichlorophenyl)-l H-pyrazol-4-yl]- l -methyl-2H-tetrazole;
5- [5 -bromo- -(2-bromopheny 1)- 1 H-pyrazol-4-y l]-2-methy l-2H-tetrazole;
5- [5 -bromo- -(2-bromophenyl)-l H-pyrazol-4-yl]- l -methy l-2H-tetrazole;
5- [5 -bromo- -(3-bromophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5- [5 -bromo- -(4-bromophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazoIe;
5- [5 -bromo- .-(4-bromophenyl)-l H-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5- [5 -bromo- -(4-fluoropheny 1)- 1 H-pyrazol-4-y l]-2-methy l-2H-tetrazole;
5- [5 -bromo- -(4-fluorophenyl)-l H-pyrazol-4-yl]- l -methy l-2H-tetrazole;
5- [5 -bromo- -(2-fluoropheny 1)- 1 H-pyrazoI-4-yl]-2-methy l-2H-tetrazole;
5- [5 -bromo- -(2-fluorophenyl)-lH-pyrazol-4-yl]- l -methyl-2H-tetrazole;
5- [5 -bromo- -(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- [5 -bromo- -(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(2,4-dimethylphenyl)- l H-pyrazoI-4-yl]- l -methyl-2H-tetrazole;
5- [5 -bromo- -(2,5-dimethylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(2,5-dimethylphenyl)- l H-pyrazol-4-yl]- l -methyl-2H-tetrazole;
• 5- [5 -bromo- -(2,6-dimethylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(2,6-dimethylpheny])-l H-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5- [5 -bromo- -(3,4-dimethylphenyl)-l H-pyrazoI-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(3,4-dimethylphenyl)- lH-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5- [5 -bromo- -(3,5-dimethylpheny 1)- 1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [5 -bromo- -(3,5-dimethylpheny 1)- 1 H-pyrazol-4-y 1]- 1 -methyl-2H-tetrazole;
5- [5 -bromo- -(2-ethylphenyl)- 1 H-pyrazoI-4-yl]-2-methy l-2H-tetrazole; 5- 5-bromd-l -(2-ethylphenyl)- lH-pyrazol-4-yl]-l -methy l-2H-tetrazole; 5- 5-bromo- 1 -(4-ethylphenyl)- 1 H-pyrazol-4-yI]-2-methy l-2H-tetrazole;
5- 5-bromo-l -(4-ethylphenyI)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- 5-bromo- 1 -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole;
5- 5-bromo- l -(2-methylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- 1 -(2-methylpheny 1)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole;
5- 5-bromo- l -(4-methylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- l -(4-methylphenyl)- l H-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5 5-iodo- 1 -methyl- 1 H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5 5 -iodo- 1 -methyl- 1 H-pyrazol-4-yl)- 1 -methyl-2H-tetrazole;
5 1 ethyl-5-iodo- 1 H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- 1 -ethy 1-5-iodo- 1 H-pyrazol-4-y 1)- 1 -methyl-2H-tetrazole;
5 5-iodo- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5 5-iodo- l -(2-methylpropyl)-l H-pyrazol-4-yI]- i -methy l-2H-tetrazole;
5 1 -benzyl-5-iodo-l H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- 1 -benzyl-5-iodo- 1 H-pyrazol-4-yl)- 1 -methy l-2H-tetrazole;
5- 5-iodo- 1 -pheny 1-1 H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- 5-iodo- 1 -phenyl- l H-pyrazol-4-yl)- l -methy 1-2 H-tetrazole;
5- 1 -(2-chlorophenyl)-5-iodo- 1 H-pyrazoI-4-yl]-2-methy l-2H-tetrazole;
5- l -(2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]- l -methy 1-2 H-tetrazole;
5- l -(3-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- l -(3-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-l -methy 1-2 H-tetrazole;
5- 1 -(4-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- l -(4-chlorophenyl)-5-iodo- l H-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- 1 -(2,3-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2-methyl-2H-tetrazole
5- 1 -(2,3-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-y I]- 1 -methy l-2H-tetrazole
5- l -(2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole
5- l -(2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l -methyl-2H-tetrazole
5- l -(2,5-dichIorophenyl)-5-iodo- lH-pyrazol-4-yl]-2-methyl-2H-tetrazole
5- 1 -(2,5-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -methy 1-2 H-tetrazole l -(2,6-dichlorophenyl)-5riodo- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole l -(2,6-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]- l -methy l-2H-tetrazole - [i- (3,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- [i- (3,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;- [i- (3,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- [i- (3,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;- [i- (2-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- [i- (2-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;- [i- (3-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- [i- (3-bromophenyl)-5-iodo- ] H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;- [i- (4-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- [i- (4-bromophenyI)-5-iodo-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;- [i- (4-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- [i- (4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-l-methyl-2H-tetrazole;- [i- (2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;- [i- (2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-l -methy I-2H-tetrazole;- [i- (2,3-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole- [i- (2,3-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole- [i- (2,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yI]-2-methyl-2H-tetrazole- [i- (2,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole- [i- (2,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole- [i- (2,5-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole- [i- (2,6-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole- ;ι- (2,6-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole- ;i- (3,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyI-2H-tetrazole- ;i- (3,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole- Ί- (3,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole- 1- (3,5-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-l-methyl-2H-tetrazole- [1- (2-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- [i- (2-ethylphenyl)-5-iodo- 1 H-pyrazoI-4-y 1]- 1 -methy l-2H-tetrazole;- [1- (4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;- (4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;- ;5- iodo- 1 -(4-methoxypheny 1)- 1 H-pyrazol-4-y l]-2-methyl-2H-tetrazole;- "5- iodo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;- 5- iodo- 1 -(2-methy Iphenyl)- 1 H-pyrazol-4-y l]-2-methy l-2H-tetrazole; -[5-iodo-l -(2-methylphenyl)- 1 H-pyrazoI-4-yI]- 1 -methyl-2H-tetrazole;-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;-ethyI-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
-ethy l-5-( 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-ethy l-5-( 1 -ethyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
-ethy l-5-( 1 -ethyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
-ethyl-5-[l-(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
- ethyl-5-[l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-(l -benzyl- 1 H-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
-( 1 -benzyl- 1 H-pyrazol-4-yl)- 1 -ethy I-2H-tetrazole;
- ethyl-5-(l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;'
-ethyl-5-( 1 -phenyl- 1 H-pyrazol-4-yI)-2H-tetrazole;
-[l-(2-chlorophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[l-(2-chlorophenyl)-l H-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
-[l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[l -(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
-[l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
-[l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
-[l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[ 1 -(3,4-dichloropheny 1)- 1 H-pyrazol-4-yI]- 1 -ethy l-2H-tetrazole;
-[l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
-[l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
-[ 1 -(2-bromopheny 1)- 1 H-pyrazol-4-y 1]- 1 -ethyl-2H-tetrazole; 5-[i -(3-bromophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[ 1 -(3-bromopheny I)- 1 H-pyrazol-4-ylJ- 1 -ethy l-2H-tetrazole; 5-[l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[ 1 -(4-bromophenyl)- 1 H-pyrazol-4-y I]- 1 -ethy l-2H-tetrazole; 2-ethyl-5-[l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- ethyl-5-[l-(4-fluorophenyl)-lH-pyrazol-4-yI]-2H-tetrazole;
2- ethyl-5-[l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazple; l-ethyI-5-[l-(2-fluorophenyI)-lH-pyrazol-4-yl]-2H-tetrazole; 5-[l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-[l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole 5-[l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-[l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole 5-[l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-[l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole 5-[ 1 -(2,6-dimethylphenyl)- 1 H-pyrazol-4-yl]-2-ethy l-2H-tetrazole 5-[ 1 -(2,6-dimethylpheny I)- 1 H-pyrazoI-4-yl]- 1 -ethyl-2H-tetrazole 5-[l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-[ 1 -(3,4-dimethy lphenyl)- 1 H-pyrazol-4-yl]- 1 -ethy l-2H-tetrazole 5-[l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-[l -(3, 5-dimethy lphenyl)-! H-pyrazol-4-yl]-l-ethyl-2H-tetrazole
2-ethyl-5- l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- ethyl-5- l-(2-ethylphenyl)-lH-pyrazol-4-y]]-2H-tetrazole;
2- ethyl-5- l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 - ethy 1-5 - l-(4-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5- l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 - ethy 1-5- l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5- l-(2-methy lphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1- ethyl-5- l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5- l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole; l-ethyl-5- l-(4-methy lphenyl)- lH-pyrazol-4-yl]-2H-tetrazole; 5-(5-chloro-l -methyl- lH-pyrazol-4-yl)-2-ethyl-2H-tetrazole; 5-(5-chloro-l -methyl- 1 H-pyrazol-4-yl)- 1 -ethyl-2H-tetrazole; 5-(5-chloro-l-ethyl-lH-pyrazol-4-yl)-2-ethyl-2H-tetrazole; - 5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)- 1 -ethy l-2H-tetrazole;
- 5-chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2-ethy l-2H-tetrazole;- 5-chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4-y I]- 1 -ethy l-2H-tetrazole;- l -benzyl-5-chloro-l H-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
- l -benzyl-5-chloro-l H-pyrazol-4-yl)-l-ethyl-2H-tetrazole;
- 5-chloro- phenyl- l H-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
- 5-chloro- phenyl- 1 H-pyrazol-4-y 1)- 1 -ethy l-2H-tetrazole;
- 5-chloro- 2-chlorophenyl)- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-chloro- 2- chlorophenyl)- 1 H-pyrazol-4-y -ethyl-2H-tetrazole;- 5-chloro- 3- chlorophenyl)- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-chloro- 3- chlorophenyl)-l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole;- 5-chloro- 4- chlorophenyl)- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-chloro- 4-chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole;- 5-chloro- 2,3 -dichlorophenyl)- 1 H -pyrazol -4-yl] -2-ethyl-2H -tetrazole- 5-chloro- 2,3 -dichlorophenyl)- I H -pyrazol -4-yl] - l -ethyl-2H -tetrazole- 5-chloro- 2,4 -dichlorophenyl)- H- -pyrazol -4-yl]- -2-ethyl-2H -tetrazole- 5-chloro- 2,4 -dichlorophenyl)- I H -pyrazol -4-yl] - l -ethyl-2H -tetrazole- 5-chloro- 2,5 -dichlorophenyl)- H -pyrazol -4-yl]- -2-ethyl-2H -tetrazole- 5-chloro- 2,5 -dichlorophenyl)- I H -pyrazol -4-yl]. - l -ethyl-2H -tetrazole- 5-chloro- 2,6 -dichlorophenyl)- I H -pyrazol -4-yl]- -2-ethyl-2H -tetrazole- 5-chloro- 2,6 -dichlorophenyl)- I H -pyrazol -4-yl] - l -ethyl-2H -tetrazole- 5-ehloro- 3,4 -dichlorophenyl)- H -pyrazol -4-yl]. -2-ethyl-2H -tetrazole- 5-chloro- 3,4 -dichlorophenyl)- I H -pyrazol -4-yl]. - l -eth l-2H -tetrazole- 5-chloro- 3,5 -dichlorophenyl)- H -pyrazol -4-yl]- -2-ethyl-2H -tetrazole- 5-chloro- 3,5 -dichlorophenyl)- H -pyrazol -4-yl]- -l -ethyl-2H -tetrazole- 1 -(2-bromophenyl)-5-chloro- 1 H-pyrazol-4-y l]-2-ethyl-2H-tetrazole;- l -(2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole;- l -(3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- l -(3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole;- 1 -(4-bromophenyI)-5-chloro- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 1 -(4-bromophenyl)-5-chloro-l H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole;- 5-chloro- l-(4-fluorophenyl)- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-chloro- 1 -(4-fluoropheny 1)- 1 H-pyrazol-4-yl]- 1 -ethy l-2H-tetrazole; 5-chloro- 2-fluorophenyI)- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-chloro- 2-fluorophenyl)- l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole;- 5-chloro- 2.3- dimethylphenyl)- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole- 5-chloro- 2.3- dimethylphenyl) H-pyrazol-4-yl]- l -ethyl-2H-tetrazole- 5-chloro- 2.4- dimethylphenyl) H-pyrazol-4-yl]-2-ethyl-2H-tetrazole- 5-chloro- 2.4- dimethylphenyl) H-pyrazol-4-yl]- l -ethyl-2H-tetrazole- 5-chloro- 2.5- dimethylphenyl) H-pyrazol-4-yl]-2-ethyl-2H-tetrazole- 5-chloro- 2.5- dimethylphenyl) H-pyrazol-4-yl]- 1 -ethy l-2H-tetrazole- 5-chloro- 2.6- dimethylphenyl) H-pyrazol-4-yl]-2-ethyl-2H-tetrazole- 5-chloro- 2,6-dimethylphenyl) H-pyrazol-4-yl]-l -ethyl-2H-tetrazole- 5-chloro- 3,4-dimethylphenyl) H-pyrazol-4-yl]-2-ethyl-2H-tetrazole- 5-chloro- 3.4- dimethylphenyl)-lH-pyrazol-4-yl]- l -ethyI-2H-tetrazole- 5-chloro- 3.5- dimethylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole- 5-chloro- 3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l -ethyl-2H-tetrazole- 5-chloro- 2-ethylphenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-chloro- 2-ethylphenyl)- l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole;- 5-chloro- 4-ethylphenyl)- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-chloro- 4-ethylphenyl)- 1 H-pyrazol-4-ylJ- 1 -ethyl-2H-tetrazole;- 5-chloro- 4-methoxyphenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-chloro- 4-methoxyphenyl)-lH-pyrazol-4-yl]- l -ethyl-2H-tetrazole;- 5-chloro- 2-methylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-chloro- 2-methylphenyl)-l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole;- 5-chloro- 4-methylphenyl)- lH-pyrazol-4-yI]-2-ethyl-2H-tetrazole;- 5-chloro- 4-methylphenyl)-l H-pyrazol-4-yl]-l -ethyI-2H-tetrazole;
5-bromo- methyl- 1 H-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5-bromo- methyl- 1 H-pyrazol-4-yl)- 1 -ethyl-2H-tetrazole;
5-bromo- ethyl- l H-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5-bromo- ethyl- l H-pyrazol-4-yl)-l-ethyl-2H-tetrazole;
5-bromo- (2-methylpropyl)-lH-pyrazol-4-yI]-2-ethyl-2H-tetrazole; 5-bromo (2-methylpropyl)-l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole; 1 -benzyl- 5-bromo- 1 H-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
1 -benzyl- 5-bromo- l H-pyrazol-4-yl)-l -ethy 1-2 H-tetrazole;
5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)-2-ethyl-2H-tetrazole; ;5-bromo- phenyl-l H-pyrazol-4-yl)-l -ethyl-2H-tetrazole;
5-bromo- 2-chIorophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- "5-bromo- 2- chlorophenyl)-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole;
5-bromo- 3- chlorophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-bromo- 3- chlorophenyl)-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5-bromo- 4- chlorophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-bromo- 4-chlorophenyl)-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5-bromo- 2,3-dichlorophenyl )-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-bromo- 2.3- dichlorophenyl - 1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole- 5-bromo- 2.4- dichlorophenyl - l H-pyrazol-4-yI]-2-ethyl-2H-tetrazole 5-bromo- 2.4- dichlorophenyl - 1 H-pyrazol-4-y 1]- 1 -ethyl-2H-tetrazole 5-bromo- 2.5- dichlorophenyl -l H-pyrazoI-4-yl]-2-ethyl-2H-tetrazole 5-bromo- 2.5- dichlorophenyl -1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole 5-bromo- 2.6- dichIorophenyl )-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-bromo- 2,6-dichlorophenyl - 1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole 5-brOmo- 3,4-dichlorophenyl - 1 H-pyrazol-4-y l]-2-ethyl-2H-tetrazole 5-bromo- 3.4- dichlorophenyl - 1 H-pyrazol-4-y 1]- 1 -ethy 1-2 H-tetrazole 5-bromo- 3.5- dichlorophenyl -l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-bromo- 3,5-dichlorophenyI - 1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole 5-bromo- 2-bromopheny 1)- 1 H-pyrazol-4-y l]-2-ethy l-2H-tetrazole; 5-bromo- 2- bromophenyl)-l H-pyrazol-4-yl]- l -ethyI-2H-tetrazole; 5-bromo- 3- bromophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-bromo- 3- bromophenyl)-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole;
5-bromo- 4- bromophenyl)- 1 H-pyrazol-4-yl]-2-ethy l-2H-tetrazole; 5-bromo- 4-bromopheny 1)- 1 H-pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole; 5-bromo- 4-fluorophenyl)- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-bromo- 4-fluorophenyl)-l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole; 5-bromo- 2-fluorophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-bromo- 2-fluorophenyl)- lH-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5-bromo- 2,3-dimethylphenyl)- H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;- 5-bromo- 2.3- dimethylphenyl)-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole;
5-bromo- 2.4- dimethylphenyl)- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-bromo- 2,4-dimethylphenyl)-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5 5-bromo- 2,5-dimethylphenyl)- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5 5-bromo- 2.5- dimethylphenyl)- lH-pyrazol-4-yl]-l -ethyl-2H-tetrazole 5 5-bromo- 2.6- dimethylphenyl)-l l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole
■ 5- 5-bromo- 2,6-dimethylphenyl)-l 1 H-pyrazol-4-yl]-l -ethyl-2H-tetrazole 5 5-bromo- 3,4-dimethylphenyl)- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5 5-bromo- 3.4- dimethylphenyl)- 1 H-pyrazol-4-ylJ- 1 -ethyl-2H-tetrazole 5 5-bromo- 3.5- dimethylphenyl)- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5- 5-bromo- 3,5-dimethylphenyl)- 1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole 5 5-bromo- 2-ethylphenyl)- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5 5-bromo- 2-ethy lpheny 1)- 1 H-pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole; 5 5-bromo- 4-ethylphenyl)-lH-pyrazol-4-yl]-2-ethyI-2H-tetrazole; 5 5-bromo- 4-ethylphenyl)- l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5 5-bromo- 4-methGxyphenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5 5-bromo- 4-methoxyphenyl)- l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole; 5 5-bromo- 2-methylphenyl)-l H-pyrazoI-4-yl]-2-ethyl-2H-tetrazole; 5 5-bromo- 2-methylphenyl)- 1 H-pyrazol-4-y 1]- 1 -ethy 1-2 H-tetrazole;
5- 5-bromo- 4-methylphenyl)- 1 H-pyrazol-4-y l]-2-ethy 1-2 H-tetrazole; 5 5-bromo- 4-methylphenyl)- l H-pyrazol-4-yl]-] -ethyl-2H-tetrazole; 2-ethyl-5-(5-iodo- 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 -ethyl-5-(5-iodo- 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2-ethyl-5-(l -ethyl-5-iodo-l H-pyrazol-4-yl)-2H-tetrazole;
1 -ethyl-5-( 1 -ethyl-5-iodo- 1 H-pyrazol-4-yl)-2H-tetrazole;
2-ethyl-5-[5-iodo-l -(2-methylpropyl)- l H-pyraz0l-4-yl]-2H-tetrazole; 1 -ethyl-5-[5-iodo- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 5-(l -benzyl-5-iodo- l H-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5-( 1 -benzyl-5-iodo- 1 H-pyrazol-4-y 1)- 1 -ethyl-2H-tetrazole;
2-ethyl-5-(5-iodo- l -phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
1 -ethyl-5-(5-iodo- l -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
5-[l -(2-chlorophenyl)-5-iodo-lH-pyrazoI-4-yl]-2-ethyl-2H-tetrazole; 5-[ 1 -(2-chloropheny l)-5-iodo- 1 H-pyrazol-4ry 1]- 1 -ethyl-2H-tetrazole; 5-[l -(3-chIorophenyl)-5-iodo- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[l -(3-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole; 5-[l -(4-chlorophenyl)-5-iodo- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 4-chlorophenyi)-5-iodo- l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole;
1 -( 22,,33--ddiicchhlloorroopphheennyyll))--55--iodo- 1 H-pyrazoI-4-yl -2-ethyl-2H-tetrazole
5- 2.3- dichlorophenyl)-5- odo-l H-pyrazol-4-yl -l -ethyl-2H-tetrazole 5- 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl -2-ethyl-2H-tetrazole 5- 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 - 1 -ethy l-2H-tetrazole ■5- 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -2-ethyl-2H-tetrazoIe 5- 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl -l -ethyl-2H-tetrazo!e 5- 2.6- dichlorophenyl)-5 odo-l H-pyrazol-4-yl -2-ethyl-2H-tetrazole 5- 2,6-dichlorophenyl)-5 odo- 1 H-pyrazol-4-yl - 1 -ethyl-2H-tetrazole ■5-, 3,4-dichlorophenyl)-5 odo- 1 H-pyrazol-4-y 1 -2-ethyl-2H-tetrazole 5- 3.4- dichlorophenyl)-5 odo- 1 H-pyrazol-4-y 1 -l -ethyl-2H-tetrazole 5- 3.5- dichlorophenyl)-5 odo- 1 H-pyrazol-4-y 1 -2-ethyl^2H-tetrazole: 5- 1 -( 33,,55--ddiicchhlloorroopphheennyyll))--55-iodo- 1 H-pyrazol-4-y 1 - 1 -ethy l-2H-tetrazole; 5- l -(2-bromophenyl)-5-iodo-l H-pyrazol-4-yI]-2-ethyl-2H-tetrazol.e; 5- l -(2-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5- l -(3-bromophenyl)-5-iOdo- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5- l -(3-bromophenyl)-5-iodo- l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5- 1 -(4-bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2-ethy l-2H-tetrazole; 5- l -(4-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 2-ethyl-5-[l -(4-fIuorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1 - ethyl-5-[l -(4-fluorophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5-[l -(2-fluorophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole; 1 -ethyl-5-[ 1 -(2-fluorophenyl)-'5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
5-[l -(2,3-dimethylphenyl)-5- odo- 1 H-pyrazol-4-y 1] ■2- -ethyl- -2H-tetrazole 5-[l -(2,3-dimethylphenyl)-5- odo-1 H-pyrazol-4-yl] •1 -ethyl- -2H-tetrazole 5-[ l -(2,4-dimethylphenyl)-5- odo- 1 H-pyrazol-4-yl] ■2- -ethyl- -2H-tetrazole 5-[l -(2,4-dimethylphenyl)-5- odo- 1 H-pyrazol-4-y 1] ■1 - -ethyl- -2H-tetrazole
5-[l -(2,5-dimethylphenyl)-5 odo- 1 H-pyrazol-4-y 1] ■2- -ethyl- -2H-tetrazole 5-[l -(2,5-dimethylphenyl)-5 odo-1 H-pyrazol-4-yl] •1 - -ethyl- -2H-tetrazole 5-[l -(2,6-dimethylphenyl)-5 odo- 1 H-pyrazol-4-yl] ■2- -ethyl- -2H-tetrazole 5-[ ί -(2,6-dimethylphenyl)-5 odo-1 H-pyrazol-4-yl] ■1 - -ethyl- -2H-tetrazole 5-[l -(3,4-dimethylphenyI)-5 odo- 1 H-pyrazol-4-yl] ■2- -ethyl- -2H-tetrazole 5-[ l -(3,4-dimethylphenyl)-5 odo-1 H-pyrazol-4-yl] 1 - -ethyl- -2H-tetrazole -[l-(3,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-et yl-2H-tetrazole;-[ 1 -(3,5-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2-ethy l-2H-tetrazole;-ethyl-5-[ 1 -(2-ethy lphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
- ethyl-5-[l:(2-ethylphenyl)-5-iodo-lH-pyrazol-4-yI]-2H-tetrazole;
- ethyl-5-[l-(4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
- ethyl-5-[l-(4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-t'etrazole;
- ethy l-5-[5-iodo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazoIe; -ethy l-5-[5-iodo- 1 -(4-methoxypheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;-ethyl-5-[5-iodo- 1 -(2-methylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole; -ethyl-5-[5-iodo- 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;-ethyl-5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazoIe;
- ethyl-5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
- ( 1 -methy lethy l)-5-( 1 -methyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
-( 1 -methylethyl)-5-( 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-( 1 -ethyl- 1 H-pyrazoI-4-yl)-2-( 1 -methylethyl)-2H-tetrazole;
-( 1 -ethyl- 1 H-pyrazol-4-y 1)- 1 -( 1 -methylethyl)-2H-tetrazole;
-(l-methylethyl)-5-[l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;-(l-methylethyl)-5-[l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;-( 1 -benzyl- 1 H-pyrazol-4-yl)-2-( 1 -methy lethyl)-2H-tetrazole;
-( 1 -benzyl- 1 H-pyrazol-4-yl)- 1 -(1 -methy lethyl)-2H-tetrazole;
-(l -methylethyl)-5-( 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-( 1 -methy lethy l)-5-( 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;^-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole; '-[l-(3-chlorophenyl)-l H-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-l-(l -methy lethyl)-2H-tetrazole;-[l -(2, 3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[l -(2, 3-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[ 1 -(2,5-dichlorophenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methy lethy l)-2H-tetrazole; -[ 1 -(2,5-dichloropheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;-[l-(2,6-dichlorophenyl)-l H-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[ 1 -(2,6-dichlorophenyl)-l H-pyrazol-4-yl]- 1 -(1 -methy lethy l)-2H-tetrazole;-[ 1 -(3,4-dichlorophenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methylethy l)-2H-tetrazole;-[ 1 -(3,4-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 -(1 -methy lethy l)-2H-tetrazole;-[l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[l -(2-bromophenyl)-l H-pyrazol-4-yl]-2-(l-methy lethy l)-2H-tetrazole;-[ 1 -(2-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethyl)-2H-tetrazole;-[l-(3-bromophenyl)-1 H-pyrazol-4-yl]-2-(1;-methylethyl)-2H-tetrazole;-[ 1 -(3-bromopheny!)-l H-pyrazol-4-yl]- 1 -(1 -methy lethy l)-2H-tetrazole;-[l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[ 1 -(4-bromopheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;-[l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[l-(4-fluorophenyl)-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;-[l -(2-fluorophenyl)-lH-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;-[l-(2-fluorophenyl)-lH-pyrazol-4-yl]-l-(l -methy lethyl)-2H-tetrazole;-[ 1 -(2,3-dimethy Iphenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methy lethy l)-2H-tetrazole-[l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l-(l -methylethy l)-2H-tetrazo!e-[l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole-[ 1 -(2,4-dimethylpheny 1)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethyl)-2H-tetrazole-[l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole:-[l-(2,5-dimethyIphenyI)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole-[ 1 -(2, 6-dimethylpheny 1)- 1 H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole:-[l -(2, 6-dimethylphenyl)-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;-[l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole:-[l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[l-(3,5-dimethylphenyl)-l H-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole:-[ 1 -(2 -ethy Iphenyl)- 1 H-pyrazol-4-y l]-2-( 1 -methy lethy l)-2H-tetrazole;-[l-(2-ethylphenyl)-l H-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;-[l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[l-(4-ethylphenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole; · -(4-methoxyphenyl)- l H-pyrazoI-4-yl]-2-(l -methy lethyl)-2H-tetrazole;
· -(4-methoxyphenyI)- l H-pyrazol-4-yl]-l -(l -methylethyl)-2H-tetrazole;
- -methylethyl)-5-[l-(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
-methylethyl)-5-[ 1 -(2-methylphenyl)- 1 H-pyrazoI-4-yl]-2H-tetrazole;
- -methylethyl)-5-[l -(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
- -methylethyl)-5-[l -(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazoIe;
- -chloro-1 -methyl- l H-pyrazoI-4-yl)-2-(l -methylethyl)-2H-tetrazole;
- -chloro- 1 -methyl- 1 H-pyrazol-4-yl)-l -( 1 -methy lethyl)-2H-tetrazole;
- -chloro- 1 -ethyl- 1 H-pyrazol-4-yI)-2-(l -methylethyl)-2H-tetrazole;
- -chloro- 1 -ethy 1- 1 H-pyrazol-4-yl)-l -( l -methy lethy l)-2H-tetrazole;
- -chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2-( 1 -methy lethy l)-2H-tetrazole;· -chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4-y I]- 1 -( 1 -methy lethy l)-2H-tetrazole;- -benzyl-5-chloro-lH-pyrazol-4-yl)-2-(l -methylethyl)-2H-tetrazole;
- -benzyl-5-chloro- 1 H-pyrazol-4-yl)-l -( 1 -methylethyl)-2H-tetrazole;
· -chloro- 1 -phenyl- lH-pyrazol-4-yl)-2-( l-methylethyl)-2H-tetrazole;
- -chloro- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 -( 1 -methylethyl)-2H-tetrazole;
-1 -chloro- l -(2-chlorophenyl)-l H-pyrazol-4-yI]-2-( l -methy lethy l)-2H-tetrazole;- -chloro-1 -(2-chlorophenyl)-l H-pyrazol-4-yl]-l -( l -methy lethy l)-2H-tetrazole;- -chloro- 1 -(3-chlorophenyl)- 1 H-pyrazol-4-yl]-2-( l -methylethyl)-2H-tetrazole;- -chloro- l -(3-chlorophenyl)- lH-pyrazol-4-y I]- 1 -(1 -methy lethy l)-2H-tetrazole;- -chloro- l-(4-chlorophenyl)-l H-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole;- -chloro- 1 -(4-chloropheny 1)- 1 H-pyrazol-4-y I]- 1 -( 1 -methy lethy l)-2H-tetrazole;-1 -chloro- 1 -(2, 3-dichlorophenyl)-l H-pyrazol-4-yl]-2- 1 -methylethyl)-2H-tetrazole· -chloro- 1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-y 1]- 1 - 1 -methylethyl)-2H-tetrazole- ■chloro- 1 -(2,4-dichlorophenyl)- 1 H-pyrazol-4-yl]-2- 1 -methylethyl)-2H-tetrazole· ■chloro- 1 -(2,4-dichlorophenyl)- 1 H-pyrazol-4-y I]- 1 - 1 -methylethyl)-2H-tetrazole- -chloro- 1 -(2,5-dichlorophenyl)- 1 H-pyrazoI-4-y l]-2- 1 -methy lethy l)-2H-tetrazole- -chloro- l -(2,5-dichlorophenyl)-l H-pyrazol-4-yl]-l - 1 -methylethyl)-2H-tetrazole- ■chloro- 1 -(2,6-dichlorophenyl)- 1 H-pyrazol-4-yl]-2-' 1 -methylethyl)-2H-tetrazole- ■chloro- 1 -(2, 6-dichloropheny 1)-1 H-pyrazol-4-y 1]-1 - 1 -methylethyl)-2H-tetrazole- •chloro- l -(3,4-dichlorophenyl)-l H-pyrazol-4-yI]-2-' 1 -methylethyl)-2H-tetrazole- ■chloro-1 -(3, 4-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 - 1 -methy lethy l)-2H-tetrazole- •chloro-1 -(3, 5-dichlorophenyl)-l H-pyrazol-4-yl]-2- 1 -methy lethy l)-2H-tetrazole -[5-chloro-l-(3,5-dichlorophenyl)-lH-pyrazoI-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[l-(2-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[ 1 -(2-bromopheny l)-5-chloro- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;-[ 1 -(3-bromophenyl)-5-chloro- 1 H-pyrazol-4-y l]-2-( 1 -methylethy l)-2H-tetrazole;-[ 1 -(3-bromopheny l)-5-chloro- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;-[l-(4-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[l-(4-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;-[5-chloro-l-(4-fluorophenyl)-l H-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[5-chloro- 1 -(4-fluorophenyl)- 1 H-pyrazol-4-y I]- 1 -( 1 -methy lethy l)-2H-tetrazole;-[5-chloro-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[5-chloro-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;-[5-chloro-l-(2,3-dimethylphenyl)-l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;-[5-chloro-l -(2, 3-dimethylphenyl)-lH-pyrazol-4-yl]-l-(l -methylethy l)-2H-tetrazole;-[5-chloro- 1 -(2, 4-dimethylphenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methy lethyl)-2H-tetrazole;-[5-chloro-l-(2, 4-dimethylphenyl)- lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazo!e;-[5-chloro-l -(2, 5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[5-chloro- 1 -(2, 5-dimethylphenyl)- lH-pyrazol-4-y l|- 1 -( 1 -methy lethy l)-2H-tetrazole;-[5-chloro-l-(2,6-dimethylphenyl)-l H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[5-chloro-l -(2, 6-dimethylphenyl)-lH-pyrazol-4-yl]-l-(l -methylethy l)-2H-tetrazole;-[5-chloro-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole;-[5-chloro-l -(3, 4-dimethylphenyl)- lH-pyrazol-4-yl]-l-(l -methy lethyl)-2H-tetrazole;-[5-chloro-l -(3, 5-dimethylphenyl)- lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[5-chloro-l -(3, 5-dimethylphenyl)- lH-pyrazol-4-yl]-l-(l -methy lethyl)-2H-tetrazole;-[5-chloro-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;
-[5-chloro-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;
-[5-chloro-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;
-[5-chloro- 1 -(4-ethylphenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethyl)-2H-tetrazole;
-[5-chloro-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[5-chloro-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-l-(l -methylethy l)-2H-tetrazole;-[5-chloro-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[5-chloro-l-(2-methylphenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[5-chloro-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[5-chloro-l-(4-methylphenyl)-lH-pyrazol-4-yl]-l-(l -methylethy l)-2H-tetrazole; - (5-bromo- 1 -methyl- 1 H-pyrazol-4-y l)-2-( 1 -methy lethy l)-2H-tetrazole;
- (5-bromo- 1 -methy I- 1 H-pyrazol-4-yl)- 1 -( 1 -methy lethyl)-2H-tetrazole;
- (5-bromo- l -ethyl- l H-pyrazol-4-yl)-2-(l -methylethyl)-2H-tetrazole;
- (5-bromo- 1 -ethyl- l H-pyrazol-4-yl)- l -(l -methylethyl)-2H-tetrazole;
- 5-bromo- 1 -(2-methylpropyl)- l H-pyrazol-4-yl]-2-( l -methy lethy l)-2H-tetrazole;- 5-bromo- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethy l)-2H-tetrazole;- 1 -benzyl- 5-bromo- 1 H-pyrazol-4-yl)-2-( 1 -methylethy l)-2H-tetrazole;
- ( 1 -benzyl- 5-bromo- 1 H-pyrazoI-4-y 1)- 1 -( 1 -methylethyl)-2H-tetrazole;
- (5-bromo- 1 -phenyl- l H-pyrazol-4-yl)-2-( l -methylethy l)-2H-tetrazole;
- (5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)- l -( l -methylethyl)-2H-tetrazole;
- 5-bromo- 1 -(2-chlorophenyl)- l H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;- 5-bromo- 1 -(2-chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethyl)-2H-tetrazole;- "5-bromo- 1 -(3-chlorophenyl)- 1 H-pyfazol-4-yl]-2-( 1 -methylethy l)-2H-tetrazole;- 5-bromo- 1 -(3-chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;- 5-bromo- l -(4-chlorophenyl)- l H-pyrazol-4-yl]-2-( l -methylethy l)-2H-tetrazole;- 5-bromo- 1 -(4-chlorophenyl)- 1 H-pyrazol-4-y 1]-1 -( 1 -methy lethyl)-2H-tetrazole;- 5-bromo- (2,3-dichIorophenyl)- 1 H-pyrazol-4-yl]-2- 1 -methylethy l)-2H-tetrazole- 5-bromo- (2,3-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1■ 1 -methylethyl)-2H-tetrazole- 5-bromo- (2,4-dichloropheny 1)- 1 H-pyrazol-4-y l]-2- 1 -methylethyl)-2H-tetrazole- 5-bromo- I -(2,4-dichlorophenyl) l H-pyrazol-4-yl]- l - 1 -methylethyl)-2H-tetrazole- 5-bromo- I -(2,5-dichlorophenyl) l H-pyrazol-4-yl]-2- 1 -methylethy l)-2H-tetrazole- 5-bromo- I -(2,5-dichlorophenyl) I H-pyrazol-4-yl]- l - 1 -methylethyl)-2H-tetrazole- 5-bromo- I -(2,6-dichlorophenyl) I H-pyrazol-4-yl]-2 1 -methylethyl)-2H-tetrazole- 5-bromo- I -(2,6-dichlorophenyl) I H-pyrazol-4-yl]- l -' 1 -methylethyl)-2H-tetrazole- 5-bromo- I -(3,4-dichlorophenyl) I H-pyrazol-4-yl]-2 1 -methylethyl)-2H-tetrazole- 5-brpmo- I -(3,4-dichlorophenyl) H-pyrazol-4-yl]- l - 1 -methylethy l)-2H-tetrazole- 5-bromo- l -(3,5-dichlorophenyl)- l H-pyrazol-4-yl]-2-> 1 -methylethyl)-2H-tetrazole- 5-bromo- I -(3,5-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 - 1 -methylethyl)-2H-tetrazole- 5-bromo- 1 -(2-bromopheny 1)-1 H-pyrazol-4-y l]-2-( 1 -methy lethy l)-2H-tetrazole;- 5-bromo- [ -(2-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethyl)-2H-tetrazole;- "5-bromo- [ -(3-bromophenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;- '5-bromo- -(3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethyl)-2H-tetrazole;- "5-bromo- -(4-bromophenyl)- l H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole; - -bromo 4-bromopheny I)- 1 H-pyrazol-4-yl]- 1-( 1 -methy lethy l)-2H-tetrazole;- -bromo 4-fluorophenyl)-l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;- -bromo 4-fluorophenyl)-l H-pyrazol-4-yl]-l -(l -methy lethy l)-2H-tetrazole;- -bromo 2-fluorophenyl)-l H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;- -bromo 2-fluoropheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethyl)-2H-tetrazole;- -bromo 2,3 -d imethylphenyl - 1 H 1 -methylethyl)-2H-tetrazole- -bromo 2,3 -d methylphenyl - 1 H 1 -methylethyl)-2H-tetrazole- -bromo 2,4 -d methylphenyl - 1 H 1 -methy lethy l)-2H-tetrazole- -bromo 2,4 -d methylphenyl) -1 H 1 -methy lethy l)-2H-tetrazole-1 -bromo 2,5 -d methylphenyl -1 H 1 -methylethyl)-2H-tetrazole· -bromo 2,5 -d methylphenyl - l H 1 -methylethyl)-2H-tetrazole· -bromo 2,6 -d methylphenyF - 1 H 1 -methy lethy l)-2H-tetrazole· -bromo 2,6 -d methylphenyl) -1 H 1 -methylethyl)-2H-tetrazole- -bromo 3,4 -d methylphenyl' -1Ή 1 -methylethyl)-2H-tetrazole- -bromo- 3,4 -d methylphenyl' - 1 H 1 -methy lethy l)-2H-tetrazole- -bromo 3,5 -d methylphenyP - 1 H 1 -methylethyl)-2H-tetrazole- ■bromo- 3,5- -d methylphenyl) -1 H 1 -methylethyl)-2H-tetrazole- -bromo 2-ethy lphenyl)- 1 H-pyrazol-4-y l]-2-( 1 -me hy lethy l)-2H-tetrazole;- -bromo 2-ethy lpheny 1)- 1 H-pyrazol-4-yl]- 1 -( 1 -me hylethyl)-2H-tetrazole;- -bromo 4-ethy lphenyl)- 1 H-pyrazoI-4-yl]-2-(l -me hylethyl)-2H-tetrazole;- -bromo- 4-ethy lphenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -me hylethyl)-2H -tetrazo 1 e ;- -bromo- 4-methoxyphenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methylethy l)-2H-tetrazole;- -bromo- 4-methoxyphenyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methylethy l)-2H-tetrazole;- -bromo- 2-methylphenyl)-l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;- -bromo- 2-methylphenyl)- lH-pyrazol-4-yl]- l -(l -methy lethyl)-2H-tetrazole;- -bromo- 4-methylphenyl)-l H-pyrazol-4-yI]-2-( l -methylethyl)-2H-tetrazole;- ■bromo- 4-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l)-2H-tetrazole;- ■iodo-1 - methyl- l H-pyrazol-4-yl)-2-( l -methylethyl)-2H-tetrazole;
- ■iodo-1-: methyl- 1 H-pyrazol-4-y 1)- 1 -( 1 -methylethy l)-2H-tetrazole;
- •ethyl-5 -iodo- 1 H-pyrazol-4-yl)-2-( 1 -methylethy l)-2H-tetrazole;
- •ethyl-5 -iodo-1 H-pyrazol-4-yl)-l -( l -methylethy l)-2H-tetrazole;
- •iodo- 1 - (2-methylpropyl)- l H-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole;- •iodo- 1 - (2-methy lpropy 1)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l) 2H-tetrazole; -( 1 -benzy 1-5-iodo- 1 H-pyrazol-4-y l)-2-( 1 -methylethy l)-2H-tetrazole;
-( 1 -benzy l-5-iodo-l H-pyrazol-4-yl)- 1 -( 1 -methy lethy l)-2H-tetrazole;
-(5-iodo-l -phenyl- lH-pyrazol-4-yl)-2-(l -methylethy l)-2H-tetrazole;
-(5-iodo-l -phenyl- lH-pyrazol-4-yl)-l-(l-methylethyI)-2H-tetrazole;
-[l-(2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[ 1 -(2-chloropheny l)-5-iodo- 1 H-pyrazol-4-yl]-l -( 1 -methylethy l)-2H-tetrazole;-[l-(3-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[ 1 -(3-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l)-2H-tetrazole;-[l-(4-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[l -(4-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethy l)-2H-tetrazole;-[l-(2,3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[l-(2,3-dichlorophenyl)-5-iodo-l.H-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[l-(2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[ 1 -(2,4-dichloropheny l)-5-iodo- 1 H-pyrazol-4-y I]- 1 -( 1 -methylethyl)-2H-tetrazole;-[l -(2,5-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2.H-tetrazole;-[l -(2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[l-(2,6-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[l -(2,6-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethyl)-2H-tetrazole;-[l -(3, 4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[ 1 -(2, 6-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-l-(l -methylethy l)-2H-tetrazole;-[l-(3,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[ 1 -(3, 5-dichloropheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -(1 -methy lethy l)-2H-tetrazole;-[l-(2-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2-.(l-methylethyl)-2H-tetrazole;-[l -(2-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-l -( 1 -methylethyl)-2H-tetrazole;-[l-(3-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[l-(3-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[ 1 -(4-bromopheny l)-5-iodo- 1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;-[l-(4-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;-[l-(4-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[l -(4-fluoropheny l)-5-iodo- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethy l)-2H-tetrazole;-[l-(2-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[l-(2-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[ 1 -(2,3-dimethy lpheny I)-5-iodo- 1 H-pyrazol-4-y l]-2-( 1 -methy lethyl)-2H-tetrazole; 5-[ 1 -(2,3-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethyl)-2H-tetrazole
5-[l-(2,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methyIethyl)-2H-tetrazoIe
5-[l -(2, 4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole
5-[l-(2,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole:
5-[ 1 -(2,5-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]- 1 -( 1 -methy lethyl)-2H-tetrazole:
5-[l-(2,6-dimethyIphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methyIethyI)-2H-tetrazole:
5-[l -(2,6-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethyl)-2H-tetrazole:
5-[ 1 -(3, 4-dimethy lpheny l)-5-iodo- 1 H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;
5-[ 1 -(3,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -( 1 -methylethyl)-2H-tetrazole:
5-[ 1 -(3, 5-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole:
5-[l-(3,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;
5-[l-(2-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[l -(2 -ethy lpheny l)-5-iodo-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;
5-[l-(4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[l-(4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;
5-[5-iodo-l-(4-methoxyphenyl)-l H-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[5-iodo-l -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethy l)-2 H-tetrazole;
5-[5-iodo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[5-iodo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-l-(l -methy lethyI)-2H-tetrazole;
5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;
2-benzy l-5-( 1 -methyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
1 -benzyl-5-( 1 -methyl-1 H-pyrazol-4-yl)-2H-tetrazole;
2-benzy l-5-( 1 -ethyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
1 -benzyl-5-( 1 -ethyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2-benzyl-5-[l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 -benzyl-5-[ 1 -(2-methylpropy 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2-benzy l-5-( 1 -benzyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 -benzyl-5-( 1 -benzyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-benzy l-5-(l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5-(l -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
l-benzyl-5-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 2-benzyl-5- 3-chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 3- chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 4- c lorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 1 -benzy 1-5- 4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 2-benzyl-5- 2,3-dichlorophenyl)- 1 H ■pyrazol-4 -yl] -2H -tetrazole
1 - benzyl-5- 2,3-dichlorophenyl)- l H -pyrazol-4 -yl] -2H -tetrazole
2- benzyl-5- 2,4-dichlorophenyl)- 1 H -pyrazol-4 -yl] -2H -tetrazole
1 - benzyl-5- 2,4-dichlorophenyI)- 1 H -pyrazol-4 -yl] -2H -tetrazole
2- benzyl-5- 2,5-dichlorophenyI)- 1 H -pyrazol-4 -yl] -2H -tetrazole
1 - benzyl-5- 2,5-dichlorophenyl)- 1 H -pyrazol-4 -yl] -2H -tetrazole
2- benzyl-5- 1 - 2,6-dichIorophenyl)- 1 H- -pyrazol-4- -yl] -2H -tetrazole
1 - benzyl-5- 2,6-dichlorophenyl)- 1H- -pyrazol-4 -yl] -2H -tetrazole
2- benzyl-5- 3,4-dichlorophenyl)- 1 H -pyrazol-4 -yl] -2H -tetrazole
1 - benzyl-5- 3,4-dichlorophenyl)- 1 H -pyrazol-4 -yl] -2H -tetrazole
2- benzyl— [ (3,5-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 3,5-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 2-bromophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 - benzyl-5- 2- bromophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 3- bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 2-benzyl-5- 4- bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; .
1 - benzyl-5- 4-bromopheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- benzyl-5- 4-fluoropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 4-fluorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5 2- luorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 2-fluorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 2,3-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 2.3- dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 2.4- dimethy lphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 2.4- dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 2.5- dimethy lphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 2.5- dimethy lphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 2.6- dimethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; l-benzyl-5- 2,6-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; -benzyl-5- l -(3,4-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
- benzyI-5- 1 -(3,4-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5- l -(3,5-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5- 1 -(3,5-dimethylpheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5- l-(2-ethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5- l -(2-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5- 1 -(4-ethy lphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
- benzyl-5- l-(4-ethylpheny.l)-l H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5- l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5- l -(4-methoxypheny'l)- l H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5- l -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
- benzyI-5- 1 -(2-methylphenyl)- 1 H-pyrazol-4-yI]-2H-tetrazole;
- benzyl-5- l-(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5- l-(4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
- benzyl-5 5-chloro- l -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5 5-chloro-l -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5 5-chloro- 1 -ethyl- 1 H-pyrazol-4-yI)-2H-tetrazole;
- benzyl-5 5-chloro- 1 -ethyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
- benzyl-5- 5-chloro-l -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5- 5-chloro- l-(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 l -benzyl-5-chloro-lH-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5 l -benzyl-5-chloro- l H-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5 5-chloro- 1 -phenyl- 1 H-pyrazol-4- l)-2H-tetrazole;
- benzyl-5 5-chloro-l -phenyl- l H-pyrazol-4-yl)-2H-tetrazo!e;
- benzyl-5- 5-chloro- l -(2-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5- 5-chloro- 1 -(2-chlorophenyI)- 1 H-pyrazol-4-y l]-2H-tetrazole;- benzyl-5- 5-chloro- l -(3-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5- 5-chloro- l -(3-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5- 5-chloro- l -(4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5-l 5-chloro- l -(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- benzyl-5- 5-chloro-l -(2,3-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzy 1-5-1 5-chloro- l -(2, 3-dichlorophenyI)- l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 5-chloro-l -(2,4-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 1- benzyl-5- 5-chloro-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-chloro-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- 5-chloro-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-chloro-l-(2,6 -dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- 5-chloro-l-(2,6 -dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-chloro-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- 5-chloro- 1 -(3,4-dichloropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- benzyl-5- 5-chloro-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- benzyI-5- 5-chloro- 1 -(3, 5-dichIorophenyl)-l H-pyrazol-4-yI]-2H-tetrazole;
2- benzyl-5-l l-(2-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5-j l-(2-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-| 1 -(3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- l-(3-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2H-tetrazole; - benzyl-5- l-(4-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- l-(4-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2H-tetrazoIe; - benzyl-5- 5-chloro- 1 4-fluoropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- 5-chioro-l: 4-fluorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazo|e;
2- benzyl-5- 5-chloro- 1 2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- 5-chloro- 1 2-fluorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole; - benzyl-5- 5-chloro- 1 2,3-dimethy Ipheny I)- 1 H-pyrazol-4-y l]-2H-tetrazole
1- benzyl-5- 5-chloro- 1 2.3- dimethylphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole - benzyl-5- 5-chloro-l 2.4- dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole
1- benzyl-5- 5-chloro- 1 2.4- dimethy Ipheny l)-lH-pyrazol-4-yl]-2H-tetrazole - benzyl-5- 5-chloro-l- 2.5- dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole
1- benzyl-5- 5-chloro-l- 2.5- dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole - benzyl-5-! 5-chloro-l- 2.6- dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole
1- benzyl-5- 5-chloro-l 2,6-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole - benzyl-5-| 5-chloro-l- 3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole
1- benzyl-5-l 5-chloro-l- 3.4- dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole - benzyl-5-' 5-chloro-l- 3.5- dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole
1- benzyl-5- 5-chloro-l 3, 5-dimethy Ipheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole - benzyl-5 5-chloro-l 2-ethylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole; l-benzyl-5-' 5-chloro-l- 2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole; -benzyl-5 [5-chloro (4-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyI-5 [5-chloro (4-ethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 [5-chloro (4-methoxyphenyl)-l H-pyrazoI-4-yl]-2H-tetrazole;- benzyl-5 [5-chloro -1 (4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazoIe;- benzyl-5 [5-chloro (2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 [5-chloro (2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 [5-chloro (4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 [5-chloro (4-methylphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;- benzyl-5 '5-bromo methyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
- benzyl-5 '5-bromo methyl- l H-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5 ^5-bromo ethyl- l H-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5 ^5-bromo ethyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
- benzyl-5 L5-bromo (2-methylpropyI)- 1 H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 [5-bromo (2-methylpropyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;- benzyl-5 -benzyl -bromo-l H-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5 -benzyl ■bromo- 1 H-pyrazol-4-y l)-2H-tetrazole;
- benzyl-5 ^5-bromo- phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5 ;5-bromo- phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
- benzyl-5 5-bromo- 2-chlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;- benzyl-5 5-bromo- 2- chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazo!e;- benzyl-5- 5-bromo- 3- chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 5-bromo- 3- chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 5-bromo- 4- chlorophenyl)- lH-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 5-bromo- 4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- benzyl-5 5-bromo- 2,3-dichlorophenyl)- 1 H-pyrazol-4-yl ]-2H-tetrazole;- benzyl-5 5-bromo- 2.3- dichlorophenyl)- 1 H-pyrazol-4-yl ]-2H-tetrazole;- benzyl-5 5-bromo- 2.4- dichlorophenyl)- l H-pyrazol-4-yl ]-2H-tetrazole;- benzyl-5 5-bromo- 2.4- dichlorophenyl)- 1 H-pyrazol-4-yl ]-2H-tetrazole;- benzyl-5J 5-bromo- 2.5- dichlorophenyl)- 1 H-pyrazol-4-yl ]-2H-tetrazole;- benzyl-5 5-bromo- 2.5- dichlorophenyl)- l H-pyrazol-4-yl ]-2H-tetrazole;- benzyl-5 5-bromo- 2.6- dichlorophenyl)- l H-pyrazol-4-yl ]-2H-tetrazole;- benzyl-5 5-bromo- 2,6-dichlorophenyl)- 1 H-pyrazol-4-yl ]-2H-tetrazole;- benzyl-5 5-bromo- 3,4-dichlorophenyl)- l H-pyrazol-4-yl ]-2H-tetrazole; 1 - benzyl-5-| 5-bromo- -(3,4-dichlorophenyl)- l H-pyraz0l-4-yl]-2H-tetrazole;
2- benzyl-5-| 5-bromo- -(3,5-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- -(3,5-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyI-5-j 5-bromo- -(2-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- -(2-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-| 5-bromo- -(3-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- -(3-bromophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-J 5-bromo- -(4-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- -(4-bromophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-| 5-bromo- -(4-fluorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- -(4-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-| 5-bromo- -(2-fluorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- -(2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-| 5-bromo- -(2,3-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5-| 5-bromo- -(2,3-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5-| 5-bromo- -(2,4-dichloropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole
1- benzyl-5-| 5-bromo- -(2,4-dichloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5-| 5-bromo- -(2,5-dichlorophenyl)-l H-pyrazoI-4-yl]-2H-tetrazole
1 - benzyl-5-| 5-bromo- -(2,5-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5-| 5-bromo- -(2,6-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5-| 5-bromo- -(2,6-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5-| 5-bromo- -(3,4-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5-| 5-bromo- -(3,4-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5-| 5-bromo- -(3,5-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5-[ 5-bromo- -(3,5-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole
2- benzyI-5-| 5-bromo- -(2-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazoIe;
1 - benzyl-5-[ 5-bromo- -(2-ethyIphenyl)-l H-pyrazol-4-yI]-2H-tetrazole;
2- benzyl-5-[ 5-bromo- -(4-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- -(4-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-[ 5-bromo- -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-[ 5-bromo- -(4-methoxyphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- benzyi-5-[ 5-bromo- -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; l -benzyl-5-[ 5-bromo- -(2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 2-benzyI-5- bromo- l-(4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- bromo- 1 -(4-methy lpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- benzyl-5-' iodo-1 -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5 iodo-1 -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5 ethyl-5-iodo-lH-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5- ethyl-5-iodo-lH-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5- iodo-1 -(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- iodo-1 -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- benzyl-5-iodo- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5- benzyl-5-iodo- 1 H-pyrazoI-4-y l)-2H-tetrazole;
2- benzyl-5- iodo- 1 -phenyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
1 - benzyl-5- iodo- 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazoIe;
2- benzyl-5- 2-chlorophenyl)-5-iodo- 1 H-pyrazoI-4-y l]-2H-tetrazole;
1 - benzyl-5- 2- chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 3- chlorophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 3- chlorophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 4- chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazoIe;
1 - benzyl-5- 4-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 2,3 -dichlorophenyl) ■5- iodo- 1 H -pyrazol -4-yl] -2H-tetrazole
1 - benzyl-5- 2,3 -dichlorophenyl) ■5- iodo- 1H -pyrazol -4-yl] -2H-tetrazole
2- benzyl-5- 2,4 -dichlorophenyl)- •5- iodo- 1 H -pyrazol -4-yl] -2H-tetrazole
1 - benzyl-5- 2,4 -dichlorophenyl)- -5- iodo- 1 H ■pyrazol -4-yl] -2H-tetrazole
2- benzyI-5- 2,5 -dichlorophenyl)- ■5- iodo- 1H -pyrazol -4-yl] -2H-tetrazole
1 - benzyl-5- 2,5 -dichlorophenyl)- •5- iodo- 1 H ■pyrazol -4-yl] -2H-tetrazole
2- benzyl-5- 2,6 ■dichlorophenyl)- •5- iodo- 1H -pyrazol -4-yl] -2H-tetrazole
1 - benzyl-5- 2,6 -dichlorophenyl)- ■5- iodo- 1 H -pyrazol -4-yl] -2H-tetrazole
2- benzyl-5- 3,4 -dichlorophenyl)- ■5- iodo- 1 H -pyrazol -4-yl] -2H-tetrazole
1 - benzyl-5- 3,4 -dichlorophenyl)- -5- iodo- 1 H- -pyrazol -4-yl] -2H-tetrazole
2- benzyl-5- 3,5 -dichlorophenyl)- -5- iodo- 1 H- -pyrazol -4-yl] -2H-tetrazole
1 - benzyl-5- 3,5 ■dichlorophenyl)- 5- iodo- 1 H- -pyrazol -4-yl] -2H-tetrazole
2- benzyl-5- 2-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 2- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-, 3- bromopheny l)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole; -benzyl-5- 3- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; -benzyl-5- 4- bromophenyl)-5-iodo-l H-pyrazol-4-yI]-2H-tetrazole; •benzyl-5- 4-bromophenyl)-5-iodo- lH-pyrazol-4-yl]-2H-tetrazole;
2■benzyl-5- 4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 1 -benzyl-5- 4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 2 -benzyl-5- 1 - 2-fluorophenyl)-5-iodo- lH-pyrazol-4-yl]-2H-tetrazole; 1■benzyl-5- 2-fluorophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
2■benzyl-5- 2,3-dimethylphenyl)-5- odo-l H-pyrazol-4-yl]-2H-tetrazole 1•benzyl-5- 2.3- dimethylphenyl)-5- odo- l H-pyrazol-4-yl]-2H-tetrazole 2■benzyl-5-ι 2.4- dimethylphenyl)-5- odo- l H-pyrazol-4-yl]-2H-tetrazole 1■benzyl-5- 2.4- dimethylphenyl)-5- odo-l H-pyrazol-4-yl]-2H-tetrazole
2■benzyl-5-| 2.5- dimethylphenyl)-5- odo-l H-pyrazol-4-yl]-2H-tetrazoIe 1■benzyl-5- 2.5- dimethylphenyl)-5- odo-l H-pyrazol-4-yl]-2H-tetrazole
2·■benzyl-5- 2.6- dimethylphenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole 1•benzyl-5- 2,6-dimethylphenyl)-5- odo- 1 H-pyrazoI-4-y l]-2H-tetrazole
• - 2·■benzyl-5- 3,4-dimethylphenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole 1■benzyl-5- 3.4- dimethylphenyl)-5- odo-l H-pyrazol-4-yl]-2H-tetrazole
2-■benzyl-5- 3.5- dimethylphenyl)-5- odo-l H-pyrazol-4-yl]-2H-tetrazole 1 -■benzyl-5- 3,5-dimethylphenyl)-5- odo-l H-pyrazol-4-yl]-2H-tetrazole 2-■benzyl-5- 2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 1•benzyl-5- 2-ethy lpheny l)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
2-■benzyl-5- 4-ethy lpheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole; 1 ·■benzyl-5- 1 -(4-ethy lphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole; 2·■benzyl-5- 5-iodo-l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; ■benzyl-5- 5-iodo-l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; ■benzyl-5- 5-iodo- l -(2-methylphenyl)-l H-pyrazol-4-ylJ-2H-tetrazole; benzyl-5- 5-iodo-l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; benzyl-5- 5-iodo-l -(4-methy lp eny l)-l H-pyrazol-4-yl]-2H-tetrazole; benzyl-5- 5-iodo- 1 -(4-methylphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
(4-bromobenzyl)-5H 1 -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
(4-bromobenzyl)-5 1-methyl-l H-pyrazol-4-yI)-2H-tetrazole;
(4-bromobenzyl)-5 1 -ethyl- lH-pyrazol-4-yl)-2H-tetrazole;
-(4-bromobenzyl)-5 l -ethyl-l H-pyrazol-4-yl)-2H-tetrazole; -(4-bromobenzyl)-5-[l-(2-methylpropyI)-l H-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(2-methylpropyI)-l H-pyrazol-4-yl]-2H-tetrazole;-( 1 -benzyl- 1 H-pyrazol-4-y l)-2-(4-bromobenzy l)-2H-tetrazole;
-( 1 -benzyl- lH-pyrazol-4-yl)- 1 -(4-bromobenzy l)-2H-tetrazole;
- (4-bromobenzyl)-5-(l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
- (4-bromobenzyl)-5-(l -phenyl- lH-pyrazoI-4-yl)-2H-tetrazole;
- (4-bromobenzyl)-5-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5-[l -(2-chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl)-5-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzy l)-5-[l-(3-chloropheny I)- lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(2,3-dichlorophenyl)-lH-pyrazol-3-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(2,3-dichlorophenyl)-lH-pyrazol-3-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(2,5-dichlorophenyl)-l H-pyrazol-4-yl|-2H-tetrazole; - (4-bromobenzy l)-5-[l -(2, 5-dichloropheny I)- lH-pyrazol-4-y I |-2H-tetrazole;- (4-bromobenzyl)-5-[l-(2i6-dichlorophenyI)-lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l -(3, 5-dichloropheny l)-lH-pyrazol-4-yl]-2H-tetrazole;.- (4-bromobenzyl)-5-[l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5-[l-(2-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzy l)-5-[l-(2-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl)-5-[l-(3-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5-[l -(3-bromophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl)-5-[l-(4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole; -(4-brorhobenzyl)-5-[ 1 -(4-bromophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;-(4-bromobenzyl)-5-[l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5-[ 1 -(4-fIuoropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl)-5-[l-(2-fluorophenyI)-lH-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl)-5- 2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
- (4-bromobenzyl)-5- 2,3-d methylphenyl)- H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5- 2.3- d methylphenyl)- H-pyrazoI-4-yl]-2H-tetrazole;-(4-bromobenzy l)-5 - 2.4- d methylphenyl)- H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5- 2.4- d methylphenyl)- H-pyrazo 1-4-y 1] -2 H-tetrazo le ;-(4-bromobenzyl)-5- 2.5- d methylphenyl)- H-pyrazol-4-yl]-2H-tetrazoIe; -(4-bromobenzyl)-5- 2.5- d methylphenyl)- H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl)-5- 2.6- d methylphenyl)- H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5- 2,6-d methylphenyl)- H-pyrazo)-4-yl]-2H-tetrazole;-(4-bromobenzyl)-5- 3,4-d methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyI)-5- 3.4- d methylphenyl)- H-pyrazol-4-yl]-2H-tetrazoIe;-(4-bromobenzyI)-5- 3.5- d methylphenyl)- H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5-' 3,5-d methylphenyl)- H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl)-5-i 2-ethy lpheny 1)- 1 H-pyr "azol-4-yl]-2H-tetrazole;
-(4-bromobenzyl)-5-S 2-ethy Iphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
-(4-bromobenzyl)-5 4-ethy lphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
-(4-bromobenzyl)-5 4-ethylphenyI)- 1 H-pyrazol-4-yl]-2H-tetrazole;
-(4-bromobenzyl)-5 4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
-(4-bromobenzyl)-5 4-methoxyphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
-(4-bromobenzyl)-5 2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
-(4-bromobenzyl)-5 2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
-(4-bromobenzyl)-5 4-methylphenyl)-l H-pyrazoI-4-yl]-2H-tetrazole;
-(4-bromobenzyl)-5 4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
-(4-bromobenzy l)-5 5-chloro- 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-(4-bromobenzyl)-5 5-chloro- 1 -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
-(4-bromobenzyl)-5 5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-(4-bromobenzyl)-5 5-chloro- 1 -ethyl- l H-pyrazol-4-yl)-2H-tetrazole;
-(4-bromobenzyl)-5 5-chloro- l -(2-methylpropyl)- l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzy l)-5 5-chloro- l -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;-(l -benzyl-5-chloro- H-pyrazol-4-yl)-2-(4-bromobenzyl)-2H-tetrazole;
-( 1 -benzyl-5-chloro- H-pyrazol-4-yl)-l -(4-bromobenzyl)-2H-tetrazole;
-(4-bromobenzyI)-5 5-chloro- 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-(4-bromobenzyl)-5 5-chloro- 1 -phenyl- 1 H-pyrazol-4-y l)-2H-tetrazole; - (4-bromobenzyl) -5- r5-chloro- l -(2-chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazoIe; - (4-bromobenzyl) -5- [5-chloro- 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl' -5- [5-chloro- 1 -(3-chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl' -5- [5-chloro- l-(3-chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl[ -5- [5-chloro-l -(4-chIorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl) -5- [5-chloro-l -(4-chlorophenyI)- 1 H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl) -5- [5-chloro- 1 -(2, 3-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; - [4-bromobenzyl[ -5- [5-chloro- 1 -(2,3-dichIorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole; - (4-bromobenzyl) -5- [5-chloro- 1 -(2,4-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; - [4-bromobenzyl[ -5- [5-chloro- 1 -(2, 4-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; - [4-bromobenzyl[ -5- [5-ehloro-l -(2, 5-dichloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyP -5- [5-chloro- 1 -(2, 5-dichloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyr -5- [5-chloro- l-(2,6-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl) -5- [5-chloro- l -(2,6-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; - [4-bromobenzyl) -5- 5-chloro- 1 -(3, 4-dichloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl) -5- [5-chloro- 1 -(3, 4-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; - [4-bromobenzyl) -5- [5-chloro- 1 -(3, 5-dichloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;
-(3, 5-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; ophenyl)-5-chloro- l H-pyrazol-4-yl]-2H-tetrazole; ophenyI)-5-chloro- 1 H-pyrazol-4-y l]-2H-tetrazole;
Figure imgf000043_0001
ophenyl)-5-chloro- l H-pyrazol-4-yl]-2H-tetrazole; - ^4-bromobenzyr -5- l -(3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2H-tetrazole; - [4-bromobenzyl) -5- 1 -(4-bromophenyl)-5-chloro- 1 H-pyrazol-4-y l]-2H-tetrazole; - (4-bromobenzyl) -5- l -(4-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl^ -5- [5-chloro- l -(4-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; - 4-bromobenzyl) -5- [5-chloro- 1 -(4-fluoropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole; - [4-bromobenzyl[ -5- 5-chloro- l -(2-fluoropheny I)- l H-pyrazol-4-yl]-2H-tetrazole; - 4-bromobenzyl^ -5- 5-chloro-l -(2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; - 4-bromobenzyl) -5- 5-chloro- 1 -(2, 3-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl) -5- 5-chloro- 1 -(2, 3-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl) -5- [5-chloro- 1 -(2,4-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl) -5- [5-chloro- l -(2,4-dimethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl) -5- 5-chloro- 1 -(2, 5-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5-[5-chloro-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole
4-bromobenzyl)-5-[5-chloro-l -(2,6-dimethylphenyl)- lH-pyrazol-4-yl]-2H-tetrazole
4-bromobenzyl)-5-[5-chloro-l -(2,6-dimethylphenyl)- lH-pyrazol-4-yl]-2H-tetrazole
4-bromobenzyl)-5-[5-chloro-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole
4-bromobenzyl)-5-[5-chloro-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole
4-bromobenzyl)-5-[5-chloro-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole
4-bromobenzyl)-5-[5-chloro-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole
4-bromobenzyl)-5-[5-chloro-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4-bromobenzyl)-5-[5-chloro-l-(2-ethylphenyl)-l H-pyrazol-4-yI]-2H-tetrazole;
4-bromobenzyl)-5-[5-chloro-l-(4-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
4-bromobenzyl)-5-[5-chloro-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4-bromobenzyl)-5-[5-chloro- 1 -(4-methoxypheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
4-bromobenzyl)-5-[5-chIoro-l-(4-methoxyphenyl)-lH-pyrazol-4^yl]-2H-tetrazole;
4-bromobenzyl)-5-[5-chloro-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4-bromobenzyl)-5-[5-chloro-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4-bromobenzyl)-5-[5-chloro-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4-bromobenzyl)-5-[5-chloro-]-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4-bromobenzyl)-5-(5-bromo-l -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
4-bromobenzyl)-5-(5-bromo-l -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
4-bromobenzyl)-5-(5-bromo-l -ethyl- lH-pyrazol-4-yI)-2H-tetrazole;
4-bromobenzyl)-5-(5-bromo-l-ethyl-lH-pyrazol-4-yl)-2H-tetrazole;
4-bromobenzyl)-5-[5-bromo-l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazoIe;
4-bromobenzyl)-5-[5-bromo-l-(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole; l-benzyl-5-bromo-l H-pyrazol-4-yl)-2-(4-bromobenzyl)-2H-tetrazole;
l-benzyl-5-bromo-l H-pyrazol-4-yl)-l-(4-bromobenzyI)-2H-tetrazole;
-1 4-bromobenzyl)-5-(5-bromo-l-phenyl-lH-pyrazol-4-yl)-2H-tetrazole;
4-bromobenzyI)-5-(5-bromo-l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
-1 4-bromobenzyl)-5-[5-bromo-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 4-bromobenzyl)-5-[5-bromo-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazoIe;- 4-bromobenzyl)-5-[5-bromo-l-(3-chIorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 4-bromobenzyl)-5-[5-bromo-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 4-bromobenzyl)-5-[5-bromo-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;- 4-bromobenzyl)-5-[5-bromo- 1 -(4-chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; - (4-bromobenzyl)-5- i 5-bromo ,3-dichloropheny I)- 1 H-pyrazol-4-y l]-2H-tetrazole- (4-bromobenzyl)-5- '5-bromo .3- dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole- ^4-bromobenzyl)-5- "5-bromo ;2,4-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole.- ^4-bromobenzyl)-5- 5-bromo '2,4-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;- ^4-bromobenzyI)-5- 5-bromo ,5-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;- ^4-bromobenzyl)-5- 5-bromo .5- dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole:- ;4-bromobenzyl)-5- 5-bromo .6- dichloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;- ^4-bromobenzyl)-5- 5-bromo ,6-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5- 5-bromo 3.4- dichlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazoIe:- (4-bromobenzyl)-5- 5-bromo 1.4- dichloropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole:- (4-bromobenzyl)-5- 5-bromo 3.5- dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole:- (4-bromobenzyl)-5- 5-bromo 3,5-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5- 5-bromo- -bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5- 5-bromo- 2- bromophenyl)- 1 H-pyrazol-4-yI]-2H-tetrazole;- (4-bromobenzyl)-5- 5-bromo- 3- bromopheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;- (4-bromobenzyl)-5- 5-bromo- 3- brornophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5- 5-bromo- 4- bromophenyl)- 1 H-pyrazol 4-y l]-2H-tetrazole;- -bromobenzyl)-5- 5-bromo- 4-bromopheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;- 4-bromobenzyl)-5- 5-bromo- 4-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;- 4-*bromobenzyl)-5- 5-bromo- -fluorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5- 5-bromo- 2-fluorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;- (4-bromobenzyl)-5- 5-bromo- 2-fluorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazo!e;- 4-bromobenzyl)-5- 5-bromo- (2,3 -dimethylphenyl) -1 H -pyrazol -4-yl] -2H-tetrazole- (4-bromobenzyl)-5- 5-bromo- (2,3 -dimethylphenyl) - 1 H -pyrazol -4-yl] -2H-tetrazole- 4-bromobenzyl)-5- 5-bromo- (2,4 -dimethylphenyl) - 1 H -pyrazol -4-yl] -2H-tetrazole- (4-bromobenzyl)-5- 5-bromo- (2,4 -dimethylphenyl) - I H -pyrazol -4-yl] -2H-tetrazole- 4-bromobenzyl)-5- 5-bromo- (2,5 -dimethylphenyl - 1 H -pyrazol -4-yl] -2H-tetrazoIe- 4-bromobenzyl)-5- 5-bromo- (2,5 -dimethylphenyl) - I H -pyrazol -4-yl] -2H-tetrazole- 4-bromobenzyl)-5- 5-bromo- (2,6 -dimethylphenyl) -I H -pyrazol -4-yl] -2H-tetrazole- 4-bromobenzy l)-5 - 5-bromo- (2,6 -dimethylphenyl) - 1 H- -pyrazol -4-yl] -2H-tetrazole- 4-bromobenzyI)-5- 5-bromo- (3,4 -dimethylphenyl) - 1 H -pyrazol -4-yl] -2H-tetrazoJe- (4-bromobenzyl)-5- 5-bromo- (3,4 -dimethylphenyl) -1 H- -pyrazol -4-yl] -2H-tetrazole- 4-bromobenzyl)-5- 5-bromo- (3,5 -dimethylphenyl) - 1 H- -pyrazol- -4-yl] -2H-tetrazole 1- (4-bromobenzyl)-5-[5-bromo-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5-[5-bromo-l-(2-et ylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[5-bromo-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5-[5-bromo-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[5-bromo-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5-[5-bromo-l-(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5-[5-bromo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 2-(4-bromobenzyl)-5-[5-bromo-l-(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[5-bromo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazoIe;
2- (4-bromobenzyl)-5-[5-bromo-l-(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[5-bromo-l-(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazoIe;
2- (4-bromobenzy l)-5-(5-iodo- 1 -methyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
1 -(4-bromobenzy l)-5-(5-iodo-l -methyl- 1 H-pyrazoI-4-y l)-2H-tetrazole;
2-(4-bromobenzyl)-5-( 1 -ethyl-5-iodo- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 - (4-bromobenzy l)-5-(l-ethyl-5-iodo-lH-pyrazol-4-yl)-2H-tetrazole;
2- (4-bromobenzyl)-5-[5-iodo-l-(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[5-iodo-l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;
5-( 1 -benzy 1-5-iodo- 1 H-pyrazol-4-y l)-2-(4-bromobenzy l)-2H-tetrazole;
5-(l-benzyl-5-iodo-lH-pyrazol-4-yl)-2-(4-bromobenzyI)-2H-tetrazole;
2- (4-bromobenzyl)-5-(5-iodo-l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
1 - (4-bromobenzy l)-5-(5-iodo-l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
- (4-bromobenzyl)-5-[l-(2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1 - (4-bromobenzy l)-5-[l-(2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
- (4-bromobenzyl)-5-[l-(3-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[l-(3-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
- (4-bromobenzyl)-5-[l-(4-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[l-(4-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
- (4-bromobenzyl)-5-[l-(2,3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[l-(2,3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazoIe; - (4-bromobenzyl)-5-[l-(2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5-[l -(2,4-dichIorophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole; -(4-bromobenzyl)-5-[l-(2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole; l-(4-bromobenzyl)-5-[l-(2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl -5- [i - (2,6-dichlorophenyI)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl) -5- [ 1 - (2,6-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl) -5- [i - (3,4-dichloropheny!)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyr -5- [i - (3,4-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyI) -5- [ i - (3,5-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl) -5- [ 1 - (3,5-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl) -5- [ i - (2-bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl) -5- [i - (2-bromophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl) -5- [ 1 - (3-bromophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole; -(4-bromobenzyr -5- [1 - (3-bromophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;-(4-bromobenzyl) -5- [i - (4-bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyr -5- [i - (4-bromophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;-(4-bromobenzyl) -5- [ i - (4-fluoropheny l)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyr -5- [1 - (4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl) -5- [ i - (2-fluorophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl) -5- ;i - (2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl) -5- ;i - (2,3-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole -(4-bromobenzyl" -5- ;i - (2,3-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole-(4-bromobenzyi; -5- 1 - (2,4-dimethy Ipheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole -(4-bromobenzyl) -5- 1 - (2,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole-(4-bromobenzyl' -5- Ί - (2,5-dimethylphenyl)-5-iodo- l H-pyrazol-4-y!]-2H-tetrazole -(4-bromobenzyl) -5- ; i - (2,5-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazo!e-(4-bromobenzyl^ -5- 1 - (2,6-dimethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole -(4-bromobenzyl) -5- ;i - (2,6-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole-(4-bromobenzyI) -5- ;i - (3,4-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole -(4-bromobenzyl) -5- - (3,4-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole-(4-bromobenzyl) -5-1 1 - (3, 5-dimethy Ipheny l)-5-iodo- 1 H-pyr-azol-4-yl]-2H-tetrazole -(4-bromobenzyl) -5-1 1 - (3,5-dimethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole-(4-bromobenzyl) -5-1 1 - (2-ethy Ipheny l)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl) -5-1 1 - (2-ethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl) -5-[ 1 - -ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl) -5-[ 1 - (4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;-(4-bromobenzyl) -5-1 5- iodo-l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5-[5-iodo-l-(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5-[5-iodo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5-[5-iodo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole; 5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
5 -( 1 -methyl- H-pyrazol-4-y 1)- 1 H-tetrazol- 1 -yljmethy 1 } benzonitri le;
5-( -ethyl- lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
5-(l-ethyl-lH-pyrazol-4-yl)-l H-tetrazol- l-yl]methyl} benzonitri le;
5-[l-(2-methylpropyl)-lH-pyrazoI-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; 5-[ 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl } methyI)benzonitrile; 5-( 1 -benzyl- 1 H-pyrazol-4-yl)-2H-tetrazol-2-y ljmethyl} benzonitri le;
5-(l -benzyl- lH-pyrazol-4-yl)-l H-tetrazol- l-yl]methyl}benzonitrile;
5-(l-phenyl-lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
5-( 1 -phenyl- 1 H-pyrazol-4-y I)- 1 H-tetrazol- 1 -y l]methy 1} benzonitrile;
5-ri-(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; 5-Γ 1 -(2-chIorophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl}methyl)benzonitrile; 5-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; 5-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1 -yljmethy l)benzonitrile; 5-f l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; 5-ri-(4-chIorophenyI)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonitrile;-( {5- 1- (2,3 -dichlorophenyl)- 1H -pyrazol -4-yl] -2H -tetrazol -2-yl}methyl)benzonitrile;-( {5- 1- (2,3 -dichlorophenyl)- H -pyrazol -4-yl] -IH -tetrazol - 1 -y 1 } methy l)benzonitri le;-( {5- 1- (2,4 -dichlorophenyl)- H -pyrazol -4-yl] -2H -tetrazol -2-yl}methyl)benzonitrile;-( {5- 1- (2,4 -dichlorophenyl)- IH ■pyrazol -4-yl] -IH -tetrazol -l-yl}methyl)benzonitrile;-( {5- ;i- (2,5 -dichlorophenyl)- IH- ■pyrazol -4-yl] -2H- -tetrazol -2-yl}methyl)benzonitrile;-( {5- ;i- (2,5 -dichlorophenyl)- IH- -pyrazol -4-yl] -1H- -tetrazol - 1 -y 1 } methy l)benzonitrile;-( {5- ;i- (2,6 -dichlorophenyl)- IH -pyrazol -4-yl] -2H- -tetrazol -2-yl} methy l)benzonitrile;-( (5- 1- (2,6 -dichlorophenyl)- IH -pyrazol -4-yl] -1H -tetrazol - 1 -y 1 } methy l)benzonitrile;-( (5- 1- (3,4 -dichlorophenyl)- IH -pyrazol -4-yl] -2H -tetrazol -2-yl} methy l)benzonitrile;-( {5- 1- (3,4 ■dichlorophenyl)- IH -pyrazol -4-yl] -IH -tetrazol -l-yl}methyl)benzonitrile;-( {5-1 1- (3,5 ■dichlorophenyl)- IH- -pyrazol -4-yl] -2H- -tetrazol -2-yl} methy l)benzonitrile;-( {5-1 1- (3,5 -dichlorophenyl)- 1H- -pyrazol -4-yl] -1H- -tetrazol -l-yl}methyl)benzonitrile; 4-( {5- [·- (2-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- [i- (2-bromophenyl)-l H-pyrazol-4-yl]- 1 H-tetrazol-1 -yl} methyl)benzonitrile;
4-( {5- [i- (3-bromophenyI)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- [i- (3-bromophenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl)benzonitrile;
4-( {5- [i- (4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( (5- [i- (4-bromophenyl)- H-pyrazolr4-yl]-lH-tetrazol-l-yl}methyl)benzonitrile;
4-( {5- [i- (4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- [i- (4-fluorophenyl)-l H-pyrazol-4-yl]-l H-tetrazol-1 -yl}methyl)benzonitrile;
4-( {5- [i- (2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- [i- (2-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -y 1 } methy l)benzonitrile;
4-( {5- [i- (2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- [i- (2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyI)benzonitrile;
4-( {5- [1- (2,4-dirnethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}rnethyl)benzonitrile;
4-( {5- i- (2,4-dimethylphenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}rnethyl)benzonitrile;
4-( {5- Ί- (2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- ;i- (2,5-dimethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonitrile;
4-( {5- ;i- (2,6-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4-( (5- ;i- (2,6-dimethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonitrile;
4-( (5- 1- (3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4-( {5- ;i- (3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile;
4-( {5- Ί- (3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- 1- (3, 5-dimethylpheny I)- lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methyl)benzonitrile;
4-( {5- 1- (2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- 1- (2-ethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile;
4-( {5-1 1- (4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4-( {5-1 1- (4-ethylphenyl)-lH-pyrazol-4-y!]-lH-tetrazol-l-yl}methyl)benzonitrile;
4-( {5-1 1- (4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4-( {5-1 1- ;4-methoxyphenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl } methy l)benzonitrile;
4-( {5-1 1- (2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4-( {5-[ 1- (2-methylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol-1 -yl} methy l)benzonitrile;
4-( {5-[ 1- ^4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4-( {5-[ 1- ^4-methylphenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -y 1 } methy l)benzonitri le;
4-{ [5-( 5- chloro-1 -methyl- lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile; 4- {[5- ^5-chloro-l -methyl- lH-pyrazol-4-yl)-l H-tetrazol- l-yl]methyl}benzonitrile;
4- {[5- (5-chloro-l-ethyl-lH-pyrazol-4-y.l)-2H-tetrazol-2-yl]methyl}benzonitrile;
4- {[5- (5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)-l H-tetrazol- 1 -yljmethyl} benzonitrile;
4- {5- 5-chloro-l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4- I{5- 5-chloro- 1 -(2-methylpropy 1)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1 } methy l)benzonitrile;
4- {[5- ;i-benzyI-5-chloro-lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzonitrile;
4- {[5- (l-benzyl-5-chloro-lH-pyrazol-4-yl)-l H-tetrazol- 1 -yljmethyl} benzonitrile;
4- {[5- ^5-chloro-l -phenyl- lH-pyrazol-4-yl)-2H-tetrazol-2-yI]methyl} benzonitrile;
4- {[5- (5-chloro- 1 -phenyl- 1 H-pyrazol-4-y 1)- 1 H-tetrazol- 1 -yljmethyl} benzonitrile;
4-( :{5- 5-chloro- l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-< :{5- 5-chloro- l-(2-chlorophenyl)-lH-pyrazol-4 ylJ-l H-tetrazol- l-yl}methyl)benzonitrile;
4-1 :{5- 5-chloro-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4-( :{5- 5-chloro- 1 -(3-chlorophenyl)- 1 H-pyrazol-4-y 1J- 1 H-tetrazol- 1 -y 1} methy l)benzonitrile;
4-( :{5- 5.-chloro-l-(4-chlorophenyl)-l H-pyrazol-4-ylJ-2H-tetrazol-2-yl} methy l)benzonitrile;
4-( '{5- 5-chloro- l-(4-chlorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile;
4-( '{5- 5-chloro- 1 -(2, 3-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazoI-2- yi] me thyl)benzonitrile;
4-( :{5- 5-chloro- 1 -(2,3-dichloropheny 1)- 1 H-pyrazol-4-y IJ- 1 H-tetrazol- 1 - yi] me thyl)benzonitrile;
4-( ;{5- 5-chloro-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yI]-2H-tetrazol-2- yi] me thyl)benzonitrile;
4-( {5- 5-chloro- 1 -(2, 4-dichloropheny 1)- 1 H-pyrazol-4-ylJ- 1 H-tetrazol- 1 - yi] me thyl)benzonitrile;
4-( {5- 5-chloro- 1 -(2,5-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2- yi] \me thyl)benzonitrile;
4-( :{5- '5-chloro- l-(2,5-dichlorophenyl)-lH-pyrazol-4-ylJ-l H-tetrazol- 1- yi] me thyl)benzonitrile;
4-( {5- 5-chloro- 1 -(2, 6-dichlorophenyl)-lH-pyrazol-4-ylJ-2H-tetrazol-2- yi] me thyl)benzonitrile;
4-( Λ5- 5-chloro- 1 -(2,6-dichloropheny l)-l H-pyrazol-4-yl]-l H-tetrazol- 1 - yi] me thyl)benzonitrile;
4-( 5-chloro-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yi] [me thyl)benzonitrile; 4- ({5- [5-chloro-l -(3,4-dichloropheny 1)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi me thyl)benzonitrile;
4- {5- [5-ch!oro- l -(3,5-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2- y' me thyl)benzonitrile;
4- ({5- 5-chloro- 1 -(3, 5-dichIorophenyl)-lH-pyrazol-4-yl]- l H-tetrazol- 1 - yi me thyl)benzonitrile;
4- i{5- 5-chloro- l -(2-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)benzonitrile;
4- ^{5- 5-chloro-l -(2-bromophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl} methyl)benzonitrile;
4- {{ 5- 5-chloro- 1 -(3-bromophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)benzonitrile;
4- {5- "5-chloro- l-(3-bromophenyl)- l H-pyrazol-4-yl]- l H-tetrazol- l -yl}methyl)benzonitrile;
4- ({ 5- 5-chloro- l -(4-bromophenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)benzonitrile;
4- 5-chloro- 1 -(4-bromophenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1 } methy l)benzonitrile;
4- 5-chloro-l -(4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)benzonitrile;
4- {5- 5-chloro- l-(4-fluorophenyl)-l H-pyrazol-4-yl]-l H-tetrazol- 1 -yl} methy l)benzonitrile;
4- :{5- 5-chloro- l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)henzonitrile;
4- I{5- 5-chloro- l -(2-fluorophenyl)- l H-pyrazol-4-yl]- l H-tetrazol- 1 -yl} methy l)benzonitrile;
4- :{5- 5-chloro- 1 -(2,3-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2- yP me thyl)benzonitrile;
4-< :{5- 5-chloro- 1 -(2,3-dimethylphenyl)- 1 H-pyrazol-4-yl]- l H-tetrazol- 1 - yi] me thyl)benzonitrile;
4-( :{5- 5 -chloro- 1 -(2,4-dimethy lpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazol-2- yi) me thyl)benzonitrile;
4-( 5-chloro- 1 -(2,4-dimethy lpheny l)- l H-pyrazol-4-yl]-l H-tetrazol- 1 - ij me thyl)benzonitrile;
4-( ;{5- 5-chloro- 1 -(2,5-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2- yi] me thyl)benzonitrile;
4-( '{5- 5-chloro- 1 -(2,5-dimethylphenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi] me thyl)benzonitrile;
4-( '{5- 5-chloro- l -(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yi] me thyl)benzonitrile;
4-( {5- 5-chloro- 1 -(2,6-dimethylphenyl)-l H-pyrazol-4-yl]-l H-tetrazol- 1 - yi] me thyl)benzonitrile; 4-( '{5- [5-chloro- 1 -(3,4-dimethylphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazol-2- yi] me thyl)benzonitrile;
4-( {5- ^5-chloro- 1 -(3,4-dimethylphenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi] me thyl)benzoriitrile;
4-( {5- L5-chloro-l -(3,5-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2- yi] me thyl)benzonitrile;
4-( {5- 5-chloro- 1 -(3,5-dimethylphenyl)-l H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yi] me thyl)benzonitrile;
4-( {5- 5-chloro- l -(2-ethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)benzonitrile;
4-( {5- 5-chloro- 1 -(2-ethy lphenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1} methy l)benzonitrile;
4-( { 5- 5-chloro- l -(4-ethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2-yI}methyl)benzonitrile;
4-( (5- 5-chloro- 1 -(4-ethy lphenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1} methy l)benzonitrile;
4-( {5- 5-chloro- l -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2- yi} me thyl)benzonitrile;
4-( {5- 5-chloro- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi} me thyl)benzonitrile;
4-( {5- 5-chloro- 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4-( { 5- 5-chloro- 1 -(2-methy Ipheny 1)- 1 H-pyrazol-4-yl]- l H-tetrazol-l -yl}methyl)benzonitrile;
4-( {5- 5-chloro- l -(4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)benzonitrile;
4-( (5- 5-chloro- l -(4-methy lphenyl)- l H-pyrazol-4-yl]- l H-tetrazol- 1-yl} methy l)benzonitrile;
4-1 r[5- (5-bromo- l -methy l- l H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzo1i,itrile;
4-1 [5- 5-bromo- 1 -methyl- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -y ljmethy 1 } benzonitrile;
4-1 I[5- (5-bromo- l -ethyl- lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
4-1 [5- (5-bromo- 1 -ethyl- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -y l]methy 1 } benzonitrile;
4-( { 5- 5-bromo-l -(2-methy lpropyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- 5-bromo-l -(2-methylpropyI)- l H-pyrazol-4-yl]- l H-tetrazol- 1 -yl} methy l)benzonitrile;
4-1 [5- (l -benzyl-5-bromo-l H-pyrazol-4-yl)-2H-tetrazol-2-y ljmethy 1} benzonitrile;
4-1 [5- ( 1 -benzyl-5-bromo- 1 H-pyrazoI-4-yl)- 1 H-tetrazol- 1 -y l]methy 1 } benzonitrile;
4-1 [5- (5-bromo-l -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazol-2-y ljmethy 1} benzonitrile;
4-1 [5- (5-bromo- l -phenyl- l H-pyrazol-4-yl)-l H-tetrazol- l -yl]methyl} benzonitrile;
4-( { 5- i5-bromo-l -(2-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( (5- ^5-bromo- 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]- l H-tetrazol- l-yI} methyl)benzonitrile;
4-( (5- 5-bromo- l -(3-chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; 4- ( {5- 5-bromo- 1 -(3-chIorophenyl)- 1 H- -pyrazol-4-yl]-l H-tetrazol- l -yl}methyl)benzonitrile;
4- 5-bromo- l -(4-chlorophenyl)-l H- -pyrazol-4-yl]-2H-tetrazoI-2-yl}methyl)benzonitrile;
4- 5-bromo- 1 -(4-chlorophenyl)- 1 H- ■pyrazol-4-yl]- l H-tetrazol- 1 -yl} methy l)benzonitrile;
4- ;{5- 5-bromo- 1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2- yi me thyl)benzonitrile;
4- :{5- 5-bromo- 1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-yl]-l H-tetrazol- 1 - yi me thyl)benzonitrile;
4- ;{ 5- 5-bromo- 1 -(2, 4-dichlorophenyI)- l H-pyrazol-4-yl]-2H-tetrazol-2- y me thyl)benzonitrile;
4- :{5- 5-bromo- l -(2,4-dichlorophenyl)- l H-pyrazol-4-yl]-l H-tetrazol- 1 - yi me thyl)benzonitrile;
4- :{ 5- 5-bromo- 1 -(2, 5-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2- yi me thyl)benzonitrile;
4- ;{5- 5-bromo- l -(2,5-dichlorophenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi me thyl)benzonitrile;
4- {5- 5-bromo-l -(2,6-dichIorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2- me thyl)benzonitrile;
4- :{5- 5-bromo- l-(2,6-dichlorophenyl)- 1 H -py razo 1 -4-y 1] - 1 H -tetrazo 1 - 1 - yi me thyl)benzonitrile;
4- :{5- 5-bromo-l -(3, 4-dichlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazoI-2- yi, me thyl)benzonitrile;
4- :{5- 5-bromo- 1 -(3,4-dichloropheny 1)- 1 H-pyrazol-4-yl]-l H-tetrazol-1 - yi me thyl)benzonitrile;
4- ;{ 5- 5-bromo- 1 -(3,5-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2- yi me thyl)benzonitrile;
4- :{5- "5-bromo- 1 -(3,5-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol-1 - yi me thyl)benzonitrile;
4- (5- 5-bromo- 1 -(2-bromophenyl)- 1 H -pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4- ({5- 5-bromo- 1 -(2-bromophenyl)- 1 H ■pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1} methy l)benzonitrile;
4- ^{5- 5-bromo- 1 -(3-bromophenyl)- 1 H ■pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;
4- ^{5- 5-bromo- 1 -(3-bromophenyl)- 1 H -pyrazol-4-yl]- l H-tetrazol-1 -yl}methyl)benzonitrile;
4- [{5- 5-bromo- 1 -(4-bromopheny 1)- 1 H -pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)benzonitrile;
4- i{5- 5-bromo- 1 -(4-bromopheny 1)- 1 H •pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1} methyl)benzonitrile; ' 4- ({5- [5-bromo-l- (4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4- ({5- [5-bromo-l- (4-fluorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonitrile;
4- ({5- ^-bromo-l- (2-fluorophenyI)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitriIe;
4- ({5- i5-bromo-l- ^-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -y 1 } methyl)benzonitrile;
4- C{5- 5-bromo-l- (2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yi me thyl)benzoni trile;
4- [{5- 5-bromo-l- (2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yi me thyl)benzoni trile;
4- ({5- 5-bromo-l- (2,4-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2- yi me thyI)benzoni trile;
4- :{5- 5-bromo-l- (2,4-dimethy lphenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yi me thyl)benzoni trile;
4- :{5- 5-bromo-l- 2,5-dimethy lphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazol-2- yi me thyl)benzoni trile;
4-< :{5- 5-bromo-l- (2,5-dimethy lphenyl)- lH-pyrazol-4-yl]-l H-tetrazol- 1 - yi] me thyl)benzoni trile;
4-( :{5- 5-bromo-l- 2,6-dimethylphenyl)- 1 H-pyrazoI-4-yl]-2H-tetrazol-2- yi] me thyl)benzoni trile;
4-( '{5- 5-bromo-l- (2,6-dimethylphenyl)- lH-pyrazol-4-yl]-l H-tetrazol- 1- yi] me thyl)benzoni trile;
4-1 '{5- 5-bromo-l- (3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yii me thyl)benzoni trile;
4-( ;{5- 5-bromo-l- (3,4-dimethylpheny 1)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi] thyl)benzoni trile;
4-( ;{5- 5-bromo-l- 3,5-dimethylphenyl)-lH-pyrazoI-4-yl]-2H-tetrazol-2- yi] me thyl)benzoni trile;
4-( '{5- 5-bromo-l- (3, 5-dimethy lphenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi] me thyl)benzoni trile;
4-( (5- 5-bromo-l- (2-ethylphenyl)-lH-pyrazoI-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( .{5- 5-bromo-l- (2-ethylphenyl)-lH-pyrazol-4-yi]-l H-tetrazol- 1 -yl}methyl)benzonitrile;
4-( .{5- 5-bromo-l- (4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( {5- 5-bromo-l- (4-ethy lphenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -y 1 } methy I)benzonitri le; 4- {5- 5-bromo- I -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2- yi me hyl)benzonitrile;
4- {5- 5-bromo-l -(4-methoxyphenyl)-l H-pyrazol-4-yl]- 1 H-tetrazol-1 - yi me hyl)benzonitrile;
4-( ;{5- 5-bromo- l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-< ;{5- 5-bromo- l-(2-methylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol-1 -yl}methyl)benzonitrile;
4-( 5-bromo- l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-( ;{5- 5-bromo- l -(2-methylphenyl)-l H-pyrazol-4-yl]- l H-tetrazol- l -yl} methyl) benzonitrile;
4- {[5- 5-iodo- 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzonitrile;
4- ([5- 5-iodo- l -methyl- l H-pyrazol-4-y I)- l H-tetrazol- l -yl]methyl} benzonitrile;
4- {[5- l -ethyl-5-iodo-l H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzonitrile;
4- {[5- 1 -ethyl-5-iodo- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -y Ijmethy 1 } benzonitrile;
4-( (5- 5-iodo- l-(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-( {5- 5-iodo- 1 -(2-methy lpropy 1)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl} methyl) benzonitrile;
4- i[5- l -benzyl-5-iodo- l H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzonitrile;
4- i[5- l -benzyl-5-iodo- l H-pyrazol-4-yl)- l H-tetrazol- 1 -yl]methyl} benzonitrile;
4- {[5- 5-iodo- l -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazol-2-y Ijmethy I } benzonitrile;
4- ( [5- 5-iodo- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -y l]methy 1 } benzonitri le;
4-( { 5- l -(2-chlorophenyl)-5-iodo- l H-pyrazoi-4-yI]-2H-tetrazol-2-yl} methyl)benzonitrile;
4-( {5- 1 ^-^chloropheny -S-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -yl} methy l)benzonitrile;
4-( {5- l -(3-chlorophenyl)-5-iodo-l H-pyrazol-4-yI]-2H-tetrazol-2-yl} methyl)benzonitrile;
4-( {5- 1 -(3-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl} methy l)benzonitrile;
4-( {5- l -(4-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2-yl } methy I)benzonitrile;
4-( {5-1 1 -(4-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl } methy l)benzonitrile;
4-( {5-1 l -(2,3-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2- yi) mel hyl)benzonitrile;
4-( {5-1 1 -(2, 3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l H-tetrazol-1 - yi) met hyl)benzonitrile;
4-( { 5-( l -(2,4-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2- yl} met hyl)benzonitrile;
4-( {5-1 1 -(2,4-dichloropheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi) met hyl)benzonitrile; 4- ({5- l-(2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2- yi me thyl)benzonitrile;
4- {5- 1 -(2,5-dichloropheny l)-5-iodo-l H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yi me thyl)benzonitrile;
4- :{5- l-(2,6-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2- yi me thyl)benzonitrile;
4- :{5- 1 -(2,6-dichlorophenyI)-5-iodo- 1 H-pyrazoI-4-y 1]- 1 H-tetrazol- 1 - yi me thyl)benzonitrile;
4- :{5- l-(3,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2- me thyl)benzonitrile;
4- [{5- 1 -(3,4-dichloropheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi me thyl)benzonitrile;
4- ;{5- l-(3,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2- me thyl)benzonitrile;
4-< ;{5- 1 -(3, 5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l H-tetrazol- 1- i me thyl)benzonitrile;
4-( :{5- l-(2-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4- :{5- l-(2-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl)benzonitrile;
4-( :{5- l-(3-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( ;{5- 1 -(3-bromopheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1} methy l)benzonitrile;
4-( :{5- l-(4-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( :{5- 1 -(4-bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -y 1} methyl)benzonitrile;
4-( ,{5- l-(4-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4-( ;{5- l-(4-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy I)benzonitrile;
4-< ;{5- l-(2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;
4- :{5- 1 -(2-fluorophenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1 } methy l)benzonitrile;
4-( :{5- l-(2,3-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2- yi] ^me thyl)benzonitrile;
4-( :{5- 1 -(2,3-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yi] me thyl)benzonitrile;
4-( J5- l-(2,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2- yi] mei thyl)benzonitrile; -1 ({5-11 -(2,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -i: }mei hyl)benzonitrile;
-1 ({5-1 1 -(2,5-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazol-2-i: }mei hyl)benzonitrile;
-1 ({5-| 1 -(2, 5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l H-tetrazol- 1-i: }mei hyl)benzonitrile;
-1 ({5-| (2,6-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazol-2-i: }mei hyl)benzonitrile;
-1 ({5-| (2,6-dimethylpheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -i;mel hyl)benzonitriIe;
-1 :{5-i l-(3,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl].-2H-tetrazol-2-i: [mel hyl)benzonitrile;
-1 ;{5-i l-(3,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l H-tetrazol- 1-
[mel hyl)benzonitrile;
-{ :{5-i l-(3,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2-i] fmel hyl)benzonitrile;
-( ;{5-i (3, 5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l H-tetrazol- 1-i] [met hyl)benzonitrile;
-( ;{5-i l-(2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;-( :{5-i 1 -(2-ethy Ipheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1 } methy l)benzonitrile;-< ;{5-i l-(4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;-( :{5-i 1 -(4-ethylphenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1 } methy l)benzonitrile;-( :{5-i 5-iodo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;-( ;{5-i 5-iodo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -y 1} methyl)benzonitrile;-( :{ -[ 5-iodo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile;-( :{5-[ 5-iodo- 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl } methyl)benzonitrile;-( :{5-[ 5-iodo- l-(4-methy Ipheny I)- lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile;-( :{5-[ 5-iodo- -(4-methylphenyI)-lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile;-( 4-m
4-methoxybenzyl)-5-( 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 -ethyl- 1 H-pyrazol-4-yl)-2-(4-methoxybenzy l)-2H-tetrazole;
1 -ethyl- 1 H-pyrazol-4-yl)-l-(4-methoxybenzyl)-2H-tetrazole;
4-methoxybenzyl)-5-[l-(2-methylpropyl)-l H-pyrazol-4-yl|-2H-tetrazole; -(4-methoxybenzyI)-5-[ 1 -(2-methy ipropyl)- 1 H-pyrazol-4-y l]-2H-tetrazole; 5-( 1 -benzyl- 1 H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5-( 1 -benzyl- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzyl)-2H-tetrazole;
-(4-methoxybenzyl)-5-(l -phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
l -(4-methoxybenzyl)-5-( l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
Figure imgf000058_0001
5- (2,3 -dimethylphenyt)- 1 H -pyrazol-4-yP 4-methoxybenzyl)-2H-tetrazole 5- (2,3 -dimethylpheny])- 1 H -pyrazoI-4-y 4-methoxybenzyl)-2H-tetrazole •5- (2,4 -dimethylphenyl)- 1 H -pyrazol-4-y 4-methoxybenzyl)-2H-tetrazole 5- (2,4 ■dimethylphenyl)- 1H -pyrazol-4-y 4-methoxybenzyl)-2H-tetrazole 5- (2,5 -dimethylphenyl)- 1H ■pyrazol-4-yl 4-methoxybenzyl)-2H-tetrazole 5- (2,5 -dimethylphenyl)- I H -pyrazol-4-yl 4-methoxybenzyl)-2H-tetrazole 5- (2,6 -dimethylphenyl)- I H -pyrazol-4-yl 4-methoxybenzyl)-2H-tetrazole 5- (2,6 -dimethylphenyl)- H -pyrazol-4-yl 4-methoxybenzyl)-2H-tetrazole 5- (3,4 -dimethylphenyl)- I H -pyrazol-4-yl 4-methoxybenzyl)-2H-tetrazole 5- (3,4 ■dimethylphenyl)- I H -pyrazol-4-yl' 4-methoxybenzyl)-2H-tetrazole 5- (3,5 ■dimethylphenyl)- I H -pyrazol-4-yl 4-methoxybenzyl)-2H-tetrazole 5- (3,5 ■dimethylphenyl)- I H -pyrazol-4-yl 4-methoxybenzyl)-2H-tetrazole 5- (2-ethy Ipheny I)- 1 H-pyrazol-4-yl]-2-(4-me hoxybenzyl)-2H-tetrazole;
5- (2-ethylphenyl)- l H-pyrazol-4-yl]- l-(4-me hoxybenzyl)-2H-tetrazole;
5- (4-ethy Ipheny I)- l H-pyrazol-4-yl]-2-(4-me hoxybenzyl)-2H-tetrazole;
5- (4-ethy Ipheny 1)-1 H-pyrazol-4-yl]-l -(4-me hoxybenzyl)-2H-tetrazole;
2- methoxybenzy l)-5-[ 1 -(4-methoxypheny 1)- H-pyrazol-4-yl]-2H-tetrazole;
2- methoxybenzyl)-5-[l -(4-methoxyphenyl)- H-pyrazol-4-yl]-2H-tetrazole;
2- methoxybenzyl)-5-[ 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - methoxybenzyl)-5-[l -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- methoxybenzy l)-5-[ l -(4-methy Ipheny l)- t H-pyrazol-4-yl]-2H-tetrazole;
1 - methoxybenzyl)-5-[] -(4-methy Ipheny l)- l H-pyrazol-4-yl]-2H-tetrazole;
5- chloro- 1 -methyl- 1 H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5- chloro-1 -methyl- 1 H-pyrazol-4-y I)- l -(4-methoxybenzyl)-2H-tetrazole;
5- chloro- 1 -ethyl- l H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5- chloro- l -ethyl-l H-pyrazol-4-yl)-l-(4-methoxybenzyl)-2H-tetrazole;
5- chloro- l -(2-methylpropyl)- l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- chloro- l -(2-methylpropyl)-l H-pyrazol-4-yl]- l -(4-methoxybenzyl)-2H-tetrazole; 5- benzyl-5-chloro-l H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5- benzyl-5-chloro-lH-pyrazol-4-yl)-l -(4-methoxybenzyl)-2H-tetrazole;
5- chloro- 1 -phenyl- l H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5- chloro- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzyl)-2H-tetrazole;
5- chloro-1 -(2-chlorophenyl)- l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2-chloropheny 1)- 1 H-pyrazol-4-y I]- 1 -< 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- l -(3-chlorophenyl)- l H-pyrazol-4-yl]-2-' 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(3-chlorophenyl)- 1 H-pyrazol-4-yI]- 1 -< 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(4-chlorophenyl)- 1 H-pyrazol-4-yl] 2- 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(4-chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 - 4-methoxybenzyl):2H-tetrazole; 5- 5-chloro-l -(2,3-dichlorophenyl)-lH-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole 5- 5-chloro- l-(2,3-dichlorophenyl)-l H-pyrazol-4-yl -l -(4-methoxybenzyl)-2H-tetrazole 5- 5-chloro- 1 -(2,4-dichlorophenyl)- 1 H-pyrazol-4-y 1 -2-(4-methoxybenzyl)-2H-tetrazole 5- 5-chloro- 1 -(2,4-dichloropheny I)- 1 H-pyrazol-4-y I - l -(4-methoxybenzyI)-2H-tetrazole 5- 5-chloro- 1 -(2, 5-dichlorophenyl)- l H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole 5- 5-chloro- 1 -(2, 5-dichlorophenyl)- l H-pyrazol-4-yl - 1 -(4-methoxy benzy l)-2H-tetrazole 5- 5-chloro- 1 -(2, 6-dichlorophenyl)-l H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole 5- 5-chloro- l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl - 1 -(4-methoxybenzy l)-2H etrazole ■5- 5-chloro- 1 -(3,4-dichlorophenyl)- 1 H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole 5- 5-chloro- 1 -(3,4-dichlorophenyl)- 1 H-pyrazol-4-y 1 -l -(4-methoxybenzyI)-2H-tetrazole 5- 5-chloro- 1 -(3, 5-dichlorophenyl)- 1 H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole 5- 5-chloro- l -(3,5-dichlorophenyl)-l H-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tetrazole 5- 1 -(2-bromopheny l)-5-chloro- 1 H-pyrazol-4-y 1J-2- 4-methoxybenzyl)-2H-tetrazole; 5- 1 -(2-bromopheny l)-5-chloro-l H-pyrazol-4-yl]- 1 - 4-methoxybenzyl)-2H-tetrazole; 5- l -(3-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2- 4-methoxybenzyl)-2H-tetrazole; 5- 1 -(3-bromophenyl)-5-chloro- 1 H-pyrazol-4-yl]- 1 - 4-methoxybenzyl)-2H-tetrazole; 5- l -(4-bromophenyl)-5-chloro- lH-pyrazol-4-yl]-2- 4-methoxybenzyl)-2H-tetrazole; 5- l -(4-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-l - 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro-l -(4-fluorophenyl)-l H-pyrazol-4-yl]-2 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(4-fluorophenyl)- 1 H-pyrazol-4-yl]-2 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- l -(2-fluorophenyl)- l H-pyrazol-4-yl]-2 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2-fluofophenyl)- 1 H-pyrazol-4-yl]- 1 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2, 3-dimethylphenyl)- l H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2, 3-dimethylphenyl)- 1 H-pyrazol-4-y ]- 1 -(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2, 4-dimethylphenyl)-l H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2, 4-dimethylphenyl)-l H-pyrazol-4-y ]- 1 -(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2, 5-dimethylphenyl)- l H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro-l -(2,5-dimethylphenyl)- 1 H-pyrazol-4-y ]-l -(4-methoxybenzyl)-2H-tetrazole; -[5-chloro- 1 -(2,6-dimethylphenyl)- 1 H-pyrazol-4-yl]-2-(4-methoxy benzy l)-2H-tetrazole-[5-chloro-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole-[5-chloro-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole:-[5-chloro-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-rnethoxybenzyl)-2H-tetrazole:-[5-chloro-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole:-[5-chloro-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(2-methylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5-chloro-l-(4-methylphenyl)-lH-pyrazol-4-yl] l-(4-methoxybenzyl)-2H-tetrazole;-(5-bromo-l -methyl- lH-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
-(5-bromo- 1 -methyl- 1 H-pyrazol-4-y 1)- 1 -(4-methoxybenzy l)-2H-tetrazole;
-(5-bromo- 1 -ethyl- 1 H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
-(5-bromo-l -ethyl- lH-pyrazol-4-yl)-l -(4-methoxybenzy l)-2H-tetrazole;
-[5-bromo-l-(2-methylpropyl).-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5-bromo-l-(2-methylpropyl)-lH-pyrazol-4-yl]-l -(4-methoxybenzy l)-2H-tetrazo|e;-(l-benzyl-5-bromo-lH-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
-(l -benzy l-5-bromo-lH-pyrazol-4-yl)-l -(4-methoxybenzy l)-2H-tetrazole;
-(5-bromo- 1 -phenyl- 1 H-pyrazol-4-y l')-2-(4-methoxybenzyl)-2H-tetrazole;
-(5-bromo-l -phenyl- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzyl)-2H-tetrazole;
-[5-bromo-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5-bromo-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-l -(4-methoxybenzy l)-2H-tetrazole;-[5-bromo-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5 -bromo- 1 -(3-chloropheny 1)- 1 H-pyrazol-4-yl]- 1 -(4-methoxybenzy l)-2H-tetrazole;-[5-bromo-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;-[5-bromo-l-(4-chlorophenyl)-l H-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;-[5-brOmo-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; - '5-bromo- -(2,3-dichlorophenyl)- 1 H-pyrazol-4-yl 1 - (4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,4-dichlorophenyl)-l H-pyrazol-4-yl 2- (4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,4-dichloropheny 1)- 1 H-pyrazol-4-y 1 1 - (4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,5-dichIorophenyl)- 1 H-pyrazol-4-y 1 2- (4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,5-dichloropheny 1)- 1 H-pyrazol-4-y 1 1 - (4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,6-dichlorophenyl)- lH-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,6-dichIqrophenyl)-l H-pyrazol-4-yl - 1 -(4-methoxybenzy l)-2H-tetrazole- 5-bromo- -(3,4-dichlorophenyl)-l H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(3,4-dichlorophenyl)-l H-pyrazol-4-yl - 1 -(4-methoxybenzy l)-2H-tetrazole- 5-bromo- -(3,5-dichloropheny 1)- 1 H-pyrazol-4-y I -2-(4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(3,5-dichlorophenyl)- 1 H-pyrazol-4-y 1 - 1 -(4-methoxybenzy l)-2H-tetrazole- 5-bromo- -(2-bromopheny 1)- 1 H-pyrazol-4-y l]-2- 4-methoxybenzy l)-2H-tetrazole;- 5-bromo- -(2-bromopheny 1)- 1 H-pyrazol-4-y 1]- 1 - 4-methoxybenzy l)-2H-tetrazole;- 5-bromo- -(3-bromophenyl)-l H-pyrazol-4-yl]-2- 4-methoxybenzy l)-2H-tetrazole;- 5-bromo- -(3-bromophenyl)- 1 H-pyrazol-4-yl]-l - 4-methoxybenzy l)-2H-tetrazole;- 5-bromo- -(4-bromopheny 1)- 1 H-pyrazol-4-yl]-2- 4-methoxybenzy l)-2H-tetrazole;- 5-bromo- -(4-bromopheny 1)- 1 H-pyrazol-4-y 1]- 1 4-methoxybenzy l)-2 H-tetrazole;- 5-bromo- -(4-fluorophenyl)-l H-pyrazol-4-yl]-2 4-methoxybenzyl)-2H-tetrazole;- 5-bromo- -(4-fluorophenyl)- 1 H-pyrazol-4-yl]-l 4-methoxybenzy l)-2 H-tetrazole;- 5-bromo- -(2-fluorophenyl)-l H-pyrazol-4-yl]-2 4-methoxybenzy l)-2H-tetrazole;- 5-bromo- -(2-fIuoropheny 1)- 1 H-pyrazol-4-yl]- 1 4-methoxybenzy l)-2H-tetrazole;- 5-bromo- -(2,3-dimethylphenyl)- 1 H-pyrazol-4-y 1] 2- (4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,3-dimethylphenyl)-l H-pyrazol-4-y - 1 -(4-methoxybenzyl)-2H-tetrazole- 5-bromo- ■(2,4-dimethy lphenyl)- 1 H-pyrazol-4-y -2-(4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,4-dimethylphenyl)-l H-pyrazol-4-y - 1 -(4-methoxybenzyl)-2H-tetrazole- 5-bromo- ■(2,5-dimethylphenyl)- 1 H-pyrazol-4-y -2-(4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,5-dimethylphenyl)- 1 H-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(2,6-dimethylpheny 1)- 1 H-pyrazol-4-y 1 -2 -(4-methoxybenzy l)-2H-tetrazole- 5-bromo- -(2,6-dimethylpheny 1)- 1 H-pyrazol-4-y 1 - 1 -(4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(3,4-dimethylphenyl)-l H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole- 5-bromo- ■(3,4-dimethylphenyl)-l H-pyrazol-4-yl - 1 -(4-methoxybenzy l)-2H-tetrazole- 5-bromo- ■(3, 5-dimethy lphenyl)- 1 H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole- 5-bromo- -(3,5-dimethylphenyl)-l H-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tetrazole -1 -bromo- l -(2-ethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;· -bromo-l -(2-ethylphenyl)-l H-pyrazol-4-yl]- l -(4-methoxybenzyl)-2H-tetrazole;· ■bromo- 1 -(4-ethy lpheny 1)- 1 H-pyrazol-4-y l]-2-(4-methoxy benzy l)-2H-tetrazole ;-1 ■bromo- 1 -(4-ethy Iphenyl)- 1 H-pyrazol-4-yl]- 1 -(4-methoxybenzy l)-2H-tetrazole;- -bromo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y l]-2-(4-methoxybenzy l)-2H-tetrazole;- -bromo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y 1]- 1 -(4-methoxybenzyl)-2H-tetrazole;· -bromo- 1 -(2-methy lpheny 1)- 1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;- -bromo- 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]- l -(4-methoxybenzyl)-2H-tetrazole;- -bromo- 1 -(4-methylphenyl)- 1 H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;· -bromo- 1 -(4-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -(4-methoxybenzyl)-2H-tetrazole;- -iodo-1 -methyl- l H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
· -iodo-1 -methyl- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzyl)-2H-tetrazole;
· -ethy 1-5-iodo- 1 H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
- -ethy 1-5-iodo- 1 H-pyrazol-4-y 1)- 1 -(4-methoxybenzy l)-2H-tetrazole;
- -iodo-1 -(2-methylpropyl)- l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;- -iodo- 1 -(2-methylpropy 1)- 1 H-pyrazoI-4-y 1]- 1 -(4-methoxybenzy l)-2H-tetrazole;- -benzyl-5-iodo- 1 H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
-1 -benzyl-5-iodo-l H-pyrazol-4-yl)-l -(4-methoxybenzy l)-2H-tetrazole;
· -iodo- 1 -phenyl- 1 H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
· -iodo- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzy l)-2H-tetrazole;
- (2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2 4-methoxybenzy l)-2H-tetrazole;- (2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]- l 4-methoxybenzyl)-2H-tetrazole;-1 (3-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2 4-methoxybenzyl)-2H-tetrazole;- -(3-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 4-methoxybenzy I )-2 H-tetrazo le ;- (4-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2 4-methoxybenzyl)-2H-tetrazole;-1 (4-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-l 4-methoxybenzyl)-2H-tetrazole;- (2,3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole- (2,3-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl - 1 -(4-methoxy benzyl)-2H-tetrazole- (2,4-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole- (2,4-dichlorophenyl)-5-iodo- l H-pyrazol-4-yl - l -(4-methoxybenzyl)-2H-tetrazole- (2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole- (2,5-dichlorophenyl)-5-iodo- l H-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tetrazole-1 (2,6-dichlorophenyl)-5-iodo- l H-pyrazoI-4-yl -2-(4-methoxybenzyl)-2H-tetrazole 2,6-dichlorophenyl)-5-iodo-l H-pyrazoI-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; 3,4-dichlorophenyl)-5-iodo-lH-pyrazoI-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
3.4- dichlorophenyl)-5-iodo-lH-pyrazoI-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
3.5- dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 3,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; 2-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
2- bromophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
3- bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-methoxybenzyI)-2H-tetrazole;
3- bromopheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -(4-methoxybenzy l)-2H-tetrazole;
4- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 4-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; 4-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 4-fIuorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; 2-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 2-fIuorophenyl)-5-iodo-lH-pyrazol-4-yl]-l -(4-methoxybenzy l)-2H-tetrazole;- 1- (2,3 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzy l)-2H-tetrazole- 1- (2,3 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzy l)-2H-tetrazole- 1- (2,4 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzy l)-2 H-tetrazole- 1- (2,4 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzyl)-2H-tetrazole- 1- (2,5 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzy l)-2 H-tetrazole- 1- (2,5 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzy l)-2 H-tetrazole-1 1- (2,6 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzy l)-2H-tetrazole-1 1- (2,6 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzyl)-2H-tetrazole-1 1- (3,4 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzy l)-2H-tetrazole-1 1- (3,4 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzy l)-2H-tetrazole-1 1- (3,5 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzy l)-2H-tetrazole-1 1- (3,5 -dimethylphenyl)-5- iodo-lH -pyrazol 4-methoxybenzyl)-2H-tetrazole
2-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-me hoxybenzyl)-2H-tetrazole; 2-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-(4-me hoxybenzyl)-2 H-tetrazole; 4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-me hoxybenzyl)-2H-tetrazole; 4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-(4-me hoxybenzyl)-2H-tetrazole; iodo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; iodo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; -iodo-l -(2-methylphenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; ■iodo- l-(2-methylphenyl)-l H-pyrazol-4-yl]- l -(4-methoxybenzyl)-2H-tetrazole; -iodo- 1 -(4-methy Ipheny 1)- 1 H-pyrazol-4-y l]-2-(4-methoxybenzy l)-2H-tetrazole; -iodo- 1 -(4-methy Ipheny 1)- 1 H-pyrazol-4-y 1]- 1 -(4-methoxy benzy l)-2 H-tetrazole; -methylbenzyl)-5-(l -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
■methy lbenzyl)-5-( 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-ethyl- l H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
■eth l- 1 H-pyrazol-4-y l)-l -(3-methylbenzyl)-2H-tetrazole;
-methy lbenzyl)-5-[ 1 -(2-methy lpropy 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;, -methylbenzyl)-5-[l -(2-methylpropy I)- 1 H-pyrazol-4-yl]-2H-tetrazole;
-benzyl- l H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
-benzyl- 1 H-pyrazol-4-yl)- 1 -(3-methylbenzyl)-2H-tetrazole;
-methylbenzyl)-5-(l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
-methylbenzyl)-5-(l -phenyl- ! H-pyrazol-4-yI)-2H-tetrazole;
2-chlorophenyl)-l H-pyrazol-4-yl]-2- 3-methylbenzy l)-2H-tetrazole;
2- chlorophenyl)-l H-pyrazol-4-yl]- l - 3-methy lbenzy I)-2H-tetrazole;
3- chlorophenyl)- 1 H-pyrazol-4-yl]-2- 3-methylbenzyl)-2 H-tetrazole;
3- chlorophenyl)-l H-pyrazol-4-yl]-l - 3-methylbenzyl)-2H-tetrazole;
4- chlorophenyl)-l H-pyrazol-4-yl]-2- 3-methyIbenzyl)-2H-tetrazole;
4-chlorophenyl)-l H-pyrazol-4-yl]-l 3-methylbenzyl)-2H-tetrazole;
2,3-dichlorophenyl - 1 H-pyrazol-4-yl -2-(3-methylbenzyl)-2H-tetrazole;
2.3- dichlorophenyl - 1 H-pyrazol-4-yl - l -(3-methylbenzyl)-2H-tetrazoIe;
2.4- dichlorophenyl 1 H-pyrazol-4-yl -2-(3-methylbenzyl)-2H-tetrazole;
2.4- dichlorophenyl - l H-pyrazoI-4-yl - 1 -(3 -methy 1 benzy 1 )-2 H-tetrazo le;
2.5- dich!orophenyl - l H-pyrazol-4-yl -2-(3 -methy lbenzy l)-2 H-tetrazole;
2.5- dichlorophenyl - l H-pyrazol-4-yl -l -(3-methylbenzyl)-2H-tetrazole;
2.6- dichIorophenyl - l H-pyrazol-4-yl -2-(3-methylbenzyl)-2H-tetrazole; 2,6-dichlorophenyl - l H-pyrazol-4-yl - 1 -(3-methylbenzy l)-2H-tetrazole; 3,4-dichlorophenyl - l H-pyrazoI-4-yl -2-(3-methy lbenzy l)-2H-tetrazole;
3.4- dichlorophenyl - l H-pyrazol-4-yl -1 -(3-methylbenzy l)-2H-tetrazole;
3.5- dichlorophenyl - l H.-pyrazol-4-yl -2-(3-methy lbenzy l)-2H-tetrazole; 3,5-dichlorophenyl - l H-pyrazol-4-yl -l -(3-methy lbenzy l)-2H-tetrazole;
2-bromophenyl)-l H-pyrazol-4-yl]-2 3-methylbenzy l)-2H-tetrazole; 2- bromophenyl)- l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole;
3- bromophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;- 3- bromophenyl)- 1 H-pyrazol-4-y 1]- 1 -(3-methy lbenzyl)-2H-tetrazole;
4- bromophenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;- 4-bromophenyl)-lH-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole; 4-fluorophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 4-fluorophenyl)-l H-pyrazol-4-yl]-l -(3-methy lbenzyl)-2H-tetrazole; 2-fluorophenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 2-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -(3-methyIbenzy l)-2H-tetrazole;
2,3-dimethy Iphenyl)- 1 H-pyrazol-4-yl]-2- 3-methy lbenzyl)-2H-tetrazole
2.3- dimethylphenyl)- 1 H-pyrazol-4-yl]- 1 - 3-methy 1 benzy l)-2 H-tetrazo le
2.4- dimethy [phenyl)- 1 H-pyrazol-4-y l]-2- 3-methy lbenzyl)-2H-tetrazole
2.4- dimethylpheny 1)- 1 H-pyrazol-4-yl]- 1 - 3-methylbenzyl)-2H-tetrazole
2.5- dimethylphenyl)-l H-pyrazol-4-yl]-2- 3-methy lbenzyl)-2H-tetrazole
2.5- dimethylphenyl)- 1 H-pyrazol-4-yl]-l - 3-methylbenzyl)-2H-tetrazole
2.6- dimethy Iphenyl)- 1 H-pyrazol-4-y l]-2- 3-methy lbenzyl)-2H-tetrazole 2,6-dimethylphenyl)- 1 H-pyrazol-4-yl]- 1 - 3-methy lbenzyl)-2H-tetrazole 3,4-dimethylphenyl)-l H-pyrazol-4-yl]-2- 3-methylbenzyl)-2H-tetrazole
3.4- dimethylphenyl)-l H-pyrazol-4-yl]- l 3-methy lbenzyl)-2H-tetrazole
3.5- dimethylphenyl)-l H-pyrazol-4-yI]-2 3-methylbenzyl)-2H-tetrazole 3,5-dimethylphenyl)- 1 H-pyrazol-4-yl]- 1 3-methylbenzyl)-2H-tetrazole 2-ethy Iphenyl)- l H-pyrazol-4-yl]-2-(3-me hylbenzyl)-2H-tetrazole; 2-ethylpheny 1)- 1 H-pyrazol-4-yl]- 1 -(3-me hylbenzyl)-2H-tetrazole; 4-ethy Iphenyl)-! H-pyrazol-4-yl]-2-(3-me hylbenzyl)-2H-tetrazole;
4-ethylphenyl)-l H-pyrazol-4-yl]-l -(3-me hylbenzyl)-2H-tetrazole; 4-methoxyphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 4-methoxyphenyl)- l H-pyrazol-4-yl]-l -(3-methylbenzyl)-2H-tetrazole; methylbenzyl)-5-[ l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; methylbenzyl)-5-[ l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; methylbenzyl)-5-[l -(4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; methylbenzy l)-5-[ 1 -(4-methy Iphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; chloro- 1 -methyl- 1 H-pyrazol-4-y l)-2-(3-methy Ibenzy l)-2H-tetrazole; chloro-1 -methyl- l H-pyrazol-4-yl)-l -(3-methylbenzyl)-2H-tetrazole; chloro- 1 -ethyl- 1 H-pyrazol-4-y l)-2-(3-methylbenzyl)-2H-tetrazole;
chloro- 1 -ethyl- 1 H-pyrazol-4-yl)- l -(3-methylbenzyl)-2H-tetrazole;
chloro- l -(2-methylpropyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]- 1 -(3-methy Ibenzy l)-2H-tetrazole; ' benzyl-5-chloro- l H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
- benzyl-5-chloro-lH-pyrazol-4-yl)-l -(3-methylbenzyl)-2H-tetrazole;
- chloro- •phenyl-l H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
- chloro- •phenyl- 1 H-pyrazol-4-y 1)- 1 -(3-methy Ibenzy l)-2H-tetrazole;
- chloro- 2-chlorophenyI)- 1 H-pyrazol-4-yl]-2- 3-methylbenzyl)-2H-tetrazole;- chloro- 2- chloropheny I)- 1 H-pyrazol-4-y 1]- 1 - 3-methy Ibenzy l)-2H-tetrazole;- chloro- 3- chlorophenyl)- l H-pyrazol-4-yl]-2- 3-methy Ibenzy l)-2H-tetrazole;- chloro- 3- chloropheny I)- 1 H-pyrazol-4-y 1]- 1 - 3-methy Ibenzy l)-2H-tetrazole;- ■chloro- 4- chlorophenyl)- 1 H-pyrazol-4-yl]-2- 3-methylbenzyl)-2H-tetrazole;- ■chloro- 4-ch loropheny 1)- 1 H-pyrazol-4-y 1]- 1 - 3-methy Ibenzy l)-2H-tetrazole;- ■chloro- 2,3-dichloropheny H -pyrazol -4-yl] -2- (3-methy Ibenzy l)-2H-tetrazole- •chloro- 2.3- dichlorophenyl H -pyrazol -4-yl] -1 - (3 -methyl benzy l)-2 H-tetrazo le- ■chloro- 2.4- dichlorophenyl H -pyrazol -4-yl] -2- (3-methy I benzy I)-2 H-tetrazole- ■chloro- 2.4- dichlorophenyl H -pyrazol -4-yl] - 1 - (3-methy Ibenzy l)-2H-tetrazole- ■chloro- 2.5- dichlorophenyl H -pyrazol -4-yl] -2- (3-methy Ibenzy l)-2 H-tetrazole- ■chloro- 2.5- dichlorophenyl H -pyrazol -4-yl] - 1 - (3-methylbenzyl)-2H-tetrazole- ■chloro- 2.6- dichlorophenyl H -pyrazol -4-yl] -2- (3-methy Ibenzy l)-2H-tetrazole- •chloro- 2,6-dichlorophenyl H -pyrazol -4-yl] - 1 - (3-methy Ibenzy l)-2H-tetrazole- ■chloro- 3,4-dichlorophenyl H -pyrazol -4-yl] -2- (3-methy Ibenzy l)-2H-tetrazole- ■chloro- 3.4- dichlorophenyl H -pyrazol -4-yl] - 1 - (3-methy Ibenzy l)-2H-tetrazole- ■chloro- 3.5- dichlorophenyl H -pyrazol -4-yl] -2- (3-methylbenzyl)-2H-tetrazole- ■chloro- 3,5-dichlorophenyl H -pyrazol -4-yl] - 1 - (3-methy Ibenzy l)-2H-tetrazole- -(2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2- 3-methy lbenzyl)-2H-tetrazole;- (2-bromophenyl)-5-chloro- 1 H-pyrazoI-4-yI]- 1 - 3-methy 1 benzy l)-2 H-tetrazo le ;- (3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2- 3-methylbenzyl)-2H-tetrazole;- (3-bromopheny l)-5-chloro- 1 H-pyrazol-4-yl]- 1 - 3-methy Ibenzy l)-2H-tetrazole;
-(4-bromopheny l)-5-chloro- 1 H-pyrazol-4-yl]-2- 3-methy Ibenzy l)-2H-tetrazole; (4-bromopheny l)-5-chloro- 1 H-pyrazol-4-y 1]- 1 - 3-methy Ibenzy l)-2H-tetrazole; chloro- l -(4-fluorophenyl)- l H-pyrazol-4-yl]-2 3-methy Ibenzy l)-2H-tetrazole; 5- 5-chloro- -(4-fluorophenyl)-l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole;
5- 5-chloro- -(2-fluorophenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- 5-chloro- -(2-fluorophenyl)- l H-pyrazol-4-yl]-l -(3-methy lbenzyl)-2H-tetrazole;
5- 5-chloro- -(2,3-dimethylphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
5- 5-chloro- -(2,3-dimethylphenyl)-l H-pyrazol-4-yl]- 1 -(3-methylbenzy l)-2H-tetrazole
5- 5-chloro- -(2,4-dimethylphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
5- ^5-chloro- -(2,4-dimethylphenyl)-l H-pyrazol-4-yl]-l -(3-methy lbenzyl)-2H-tetrazole
5- 5-chloro- -(2,5-dimethylphenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
5- 5-chloro- -(2,5-dimethylphenyl)-l H-pyrazol-4-yl]-l -(3-methy lbenzyl)-2H-tetrazole
5- 5-chloro- -(2,6-dimethylphenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzy!)-2H-tetrazole
5- 5-chIoro- -(2,6-dimethylphenyl)- l H-pyrazol-4-yl]- l -(3-methylbenzy l)-2H-tetrazole
5- 5-chloro- -(3,4-dimethylphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
5- "5-chloro- -(3,4-dimethylphenyl)-l H-pyrazol-4-yl]-l -(3-methy lbenzyl)-2H-tetrazole
■ 5- 5-chloro- -(3, 5-dimethylphenyl)-l H-pyrazol-4-yl]-2 -(3-methy lbenzyl)-2H-tetrazole
5- 5-chloro- -(3,5-dimethylphenyl)-l H-pyrazol-4-yI]-l -(3-methy lbenzyl)-2H-tetrazole
5- 5-chloro- -(2-ethylphenyl)- l H-pyrazol-4-yl]-2 -(3-methy lbenzyl)-2H-tetrazole;
5- 5-chloro- -(2-ethylphenyl)- l H-pyrazol-4-yl]- l -(3-methy lbenzyl)-2H-tetrazole;
5- 5-chloro- -(4-ethylphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- 5-chloro- -(4-ethylphenyl)-l H-pyrazol-4-yl]- l -(3-methy lbenzyl)-2H-tetrazole;
5- 5-chloro- -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- 5-chloro- -(4-methoxyphenyl)-lH-pyrazol-4-yI]-l -(3-methy lbenzyl)-2H-tetrazole;
5- "5-chloro- -(2-methylphenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- 5-chIoro- -(2-methylphenyl)- l H-pyrazol-4-yl]-l -(3-methylbenzy l)-2H-tetrazole;
5- 5-chloro- -(4-methylphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- 5-chloro- -(4-methylphenyl)-l H-pyrazol-4-yl]-l -(3-methy lbenzyl)-2H-tetrazole;
5- ^5-bromo- 1 -methyl- l H-pyrazol-4-yl)-2-(3-methylbenzyI)-2H-tetrazole;
5- ^5-bromo- I -methyl- l H-pyrazol-4-yl)-l -(3-methy lbenzyl)-2H-tetrazole;
5- 5-bromo- -ethyl- 1 H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5- (5-bromo- -ethyl- l H-pyrazol-4-yl)-l -(3-methylbenzy l)-2H-tetrazole;
5- 5-bromo- -(2-methylpropyl)-l H-pyrazol-4-yl]-2-(3-methyIbenzyl)-2H-tetrazole;
5- 5-bromo- -(2-methylpropyl)-l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole;
5- ( l -benzyl-5-bromo- l H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5- ( 1 -benzyl-5-bromo- 1 H-pyrazol-4-yl)- 1 -(3-methy lbenzyl)-2H-tetrazole; 5- (5 -bromo- -phenyl- 1 H-pyrazol-4-y l)-2-(3-methy Ibenzy l)-2H-tetrazo!e;
5- (5 -bromo- -phenyl- 1 H-pyrazol-4-yl)- 1 -(3-methyIbenzyl)-2H-tetrazole;
5- [5 -bromo- 2-chlorophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- [5 -bromo- 2- chlorophenyl)- l H-pyrazol-4-yl]-l -(3-methy Ibenzy l)-2H-tetrazole;
5- [5 -bromo- 3- chlorophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- [5 -bromo- 3- chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -(3-methy Ibenzy l)-2H-tetrazole;
5- [5 -bromo- 4- chlorophenyl)-l H-pyrazol-4-yl]-2-(3-methy Ibenzy l)-2H-tetrazole;
5- [5 -bromo- 4-chlorophenyl)- l H-pyrazol-4-yl]-l -(3-methylbenzyl)-2H-tetrazole;
5- [5 -bromo- 2,3-dichlorophenyl 1 H -pyrazol -4-yl] -2- (3 -methylbenzyl)-2H -tetrazole;
5- [5 -bromo- 2.3- dichlorophenyl 1 H ■pyrazol -4-yl] -1 - (3 -methylbenzyl)-2H -tetrazole;
5- [5 -bromo- 2.4- dichlorophenyl 1 H -pyrazol 4-yl]. -2- (3 -methylbenzyl)-2H -tetrazole;
5- [5 -bromo- 2.4- dichlorophenyl 1 H -pyrazol 4-yl]- - 1 - (3 -methylbenzyl)-2H -tetrazole;
5- [5 -bromo- 2.5- dichlorophenyl 1 H -pyrazol -4-yl] -2- (3 -methy Ibenzy l)-2H -tetrazole;
5- [5 -bromo- 2.5- dichlorophenyl 1 H -pyrazol -4-yl] - 1 - (3 -methy Ibenzy l)-2H -tetrazole;
5- [5 -bromo- 2.6- dichlorophenyl 1 H -pyrazol 4-yl]. -2- (3 -methylbenzyl)-2H -tetrazole;
5- [5 -bromo- 2,6-dichlorophenyl 1H -pyrazol 4-yl]- - 1 - (3 -methylbenzyl)-2H -tetrazole;
5- [5 -bromo- 3,4-dichlorophenyl 1 H -pyrazol -4-yl]. -2- (3 -methylbenzyl)-2H -tetrazole;
5- [5 -bromo- 3.4- dichlorophenyl 1H -pyrazol 4-y|]. - 1 - [3 -methylbenzyl)-2H -tetrazole;
5- [5 -bromo- 3.5- dichlorophenyI 1 H -pyrazol 4-y|]. -2- (3 -methy Ibenzy 1)-2H -tetrazole;
5- [5 -bromo- 3,5-dichlorophenyl 1 H -pyrazol 4-yl]. - 1 - (3 -methylbenzyl)-2H -tetrazole;
5- [5 ■bromo- 2-bromophenyl)-l H-pyrazol4-yl]-2-(3-methy Ibenzy l)-2H-tetrazole;
5- [5 -bromo- 2- bromophenyl)- 1 H-pyrazol4-yl]- 1 -(3-methylbenzy l)-2H-tetrazole;
5- [5 -bromo- 3- bromophenyl)-l H-pyrazol4-yl]-2-(3-methy Ibenzy l)-2H-tetrazole;
5- [5 -bromo- 3- bromophenyl)- l H-pyrazol4-yl]- I -(3-methylbenzyl)-2H-tetrazole;
5- [5 -bromo- 4- bromophenyl)-l H-pyrazol-4-yl]-2-(3-methy Ibenzy l)-2H-tetrazole;
5- [5 -bromo- 4-bromophenyl)-l H-pyrazol-4-yl]- l -(3-methylbenzy l)-2H-tetrazole;
5- [5 -bromo- 4-fluorophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- [5 -bromo- 4-fluorophenyl)-l H-pyrazol-4-yl]-l -(3-methylbenzy l)-2H-tetrazole;
5- [5 -bromo- 2-fluorophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- [5 ■bromo- 2-fluorophenyl)- 1 H-pyrazol-4-y I]- 1 -(3-methy Ibenzy l)-2H-tetrazole;
5- [5 -bromo- 2, 3-dimethylphenyl)-l H-pyrazol-4-yl]-2-(3-methy Ibenzy l)-2H-tetrazole;
5- [5 -bromo- 2.3- dimethylphenyl)- l H-pyrazol-4-yl]-l -(3-methy Ibenzy l)-2H-tetrazole;
5- Γ5 ■bromo- 2.4- dimethylphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; -[5-bromo-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(2,5-dimethylphenyl)-l H-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;-[5-brorno-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;-[5-brorno-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(3,4-dimethylphenyl)-l H-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;-[5-bromo- 1 -(2-ethyIphenyl)- 1 H-pyrazol-4-yl]- 1 -(3-methylbenzy l)-2H-tetrazole;-[5-bromo- 1 -(4-ethy lphenyl)- 1 H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-l -(3-methylbenzy l)-2H-tetrazole;-[5-bromo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;-[5-brorno-l-(4-methoxyphenyl)-lH-pyrazoI-4-yl]-l-(3-methylbenzyI)-2H-tetrazole;-[5-bromo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(2-methylphenyl)-l H-pyrazol-4-yl]-l -(3-methylbenzy I)-2H-tetrazole;-[5-bromo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;-[5-bromo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-l-(3-methy)benzyl)-2H-tetrazole;-(5-iodo- 1 -methyl- 1 H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
-(5-iodo-l-methyl-lH-pyrazol-4-yl)-l-(3-methylbenzyl)-2H-tetrazole;
-(l-ethyl-5-iodo-lH-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
-(l-ethyl-5-iodo-lH-pyrazol-4-yl)-l-(3-methylbenzyl)-2H-tetrazole;
-[5-iodo-l-(2-methylpropyl)-lH-pyraz0l-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
-[5-iodo-l-(2-methylpropyl)-lH-pyrazol-4-yl]-l -(3-methylbenzy l)-2H-tetrazole;
-(l-benzyl-5-iodo-lH-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
-(l-benzyl-5-iodo-l H-pyrazol-4-yl)-l -(3-methylbenzy l)-2H-tetrazole;
-(5-iodo-l -phenyl- lH-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
-(5-iodo-l-phenyl-lH-pyrazol-4-yl)-l-(3-methylbenzyl)-2H-tetrazole;
-[l-(2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
-[l-(2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l -(3-methylbenzy l)-2H-tetrazole;
-[l-(3-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
-[l-(3-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l -(3-methylbenzy l)-2H-tetrazole; 4-chloropheny l)-5-iodo- 1 H-pyrazol-4-yl]-2 3-methylbenzyl)-2H-tetrazole; 4-chlorophenyl)-5-iodo- lH-pyrazol-4-yl]- l 3-methylbenzyl)-2H-tetrazole; l -ι 2,3-dichlorophenyl)-5- odo-l H-pyrazol-4-yl -2-(3-methylbenzyl)-2H-tetrazole
2.3- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl - 1 -(3-methylbenzy l)-2H-tetrazo!e
1 - 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -2-(3-methylbenzyl)-2H-tetrazole
2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl - 1 -(3-methylbenzyl)-2H-tetrazole
2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -2-(3-methylbenzyl)-2H-tetrazole
5- 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 - 1 -(3-methylbenzy l)-2H-tetrazole 5- 2.6- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl -2-(3-methylbenzyl)-2H-tetrazole 5- 2,6-dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl - 1 -(3-methylbenzy l)-2H-tetrazole 5- 3,4-dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -2-(3-methylbenzyl)-2H-tetrazole 5- 3.4- dichlorophenyl)-5- odo-1 H-pyrazol-4-yl - l -(3-methylbenzyl)-2H-tetrazole 5- 3.5- dichlorophenyl)-5- odo-l H-pyrazol-4-yl -2-(3-methylbenzyl)-2H-tetrazole 5- 3,5-dichlorophenyi)-5 odo-l H-pyrazol-4-yl - 1 -(3-methylbenzyl)-2H-tetrazole 5- 2-bromophenyl)-5-iodo- 1 H-pyrazoI-4-yl]-2- 3-methylbenzy l)-2H-tetrazole; 5- 2- bromophenyl)-5-iodo- l H-pyrazol-4-yl]-l - 3-methylbenzy l)-2H-tetrazole; 5- 3- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2- 3-methylbenzyI)-2H-tetrazole; 5- 3- bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 - 3-methylbenzyl)-2H-tetrazole; 5- 4- bromophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2- 3-methylbenzy l)-2H-tetrazole; 5- 4-bromopheny l)-5-iodo- 1 H-pyrazol-4-yl]- 1 - 3-methylbenzy l)-2H-tetrazole; 5- 4-fluorophenyl)-5-iodo- l H-pyrazol-4-yl]-2 3-methylbenzy l)-2H-tetrazole; 5- 4-fluorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 - 3-methylbenzy l)-2H-tetrazole; 5- 2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2- 3-methylbenzy l)-2H-tetrazole; 5- 2-fluorophenyl)-5-iodo- l H-pyrazol-4-yl]-l -' 3-methylbenzy I)-2H-tetrazole; 5- 2,3-dimethylphenyl)-5- odo-1 H-pyrazol-4-y ]-2-(3-methylbenzyl)-2H-tetrazole 5- 2.3- dimethylphenyl)-5- odo- 1 H-pyrazol-4-y ]- 1 -(3-methylbenzyl)-2H-tetrazole 5- 2.4- dimethylphenyl)-5- odo-1 H-pyrazol-4-y ]-2-(3-methylbenzyl)-2H-tetrazole 5- 2.4- dimethylphenyl)-5- odo-1 H-pyrazol-4-y ]-l -(3-methylbenzy l)-2H-tetrazole 5- 2.5- dimethylphenyl)-5- odo- 1 H-pyrazol-4-y ]-2-(3-methylbenzyl)-2H-tetrazole 5- 2.5- dimethylphenyl)-5- odo- 1 H-pyrazol-4-y ]-l -(3-methylbenzy l)-2H-tetrazole 5- 2.6- dimethylphenyl)-5- odo- 1 H-pyrazol-4-y ]-2-(3-methylbenzyl)-2H-tetrazole
1 - 2,6-dimethylphenyl)-5- odo- 1 H-pyrazol-4-y ]- 1 -(3-methy lbenzyl)-2H-tetrazole 3,4-dimethylphenyI)-5- odo- 1 H-pyrazol-4-y ]-2-(3-methylbenzyl)-2H-tetrazole 1 -(3,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -(3-methylbenzyl)-2H-tetrazole;- l-(3,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;- l-(3,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;- l-(2-ethylphenyl)-5-iodo-lH-pyrazol-4-yI]-2-(3-methylbenzyl)-2H-tetrazole;- l-(2-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;- l-(4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;- l-(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;- 5-iodo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;- 5-iodo-l-(4-methoxyphenyl)-l H-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;- 5-iodo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;- 5-iodo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazoIe;- 5-iodo-l-(4-methylphenyl)-lH-pyrazoI-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;- 5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;- 1 -methyl- lH-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
- 1 -methyl- lH-pyrazol-4-yl)-l-(4-nitrobenzyl)-2H-tetrazole;
- 1 -ethyl- 1 H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
- 1 -ethyl- 1 H-pyrazol-4-yl)- 1 -(4-nitrobenzyl)-2H-tetrazole;
- l-(2-methylpropyl)-lH-pyrazoI-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
- 1 -(2-methylpropy I)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazoie;
- 1 -benzyl- 1 H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
- 1 -benzyl- 1 H-pyrazol-4-y 1)- 1 -(4-nitrobenzy l)-2H-tetrazole;
- 4-nitrobenzyl)-5-(1 -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
- 4-nitrobenzyl)-5-(l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
- l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
- l-(2-chlorophenyl)-l H-pyrazol-4-yl]-l -(4-nitrobenzy l)-2H-tetrazole;
1 -(3-chlorophenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
1 -(3-chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzy l)-2H-tetrazo!e;
l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
1 -(4-chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;
l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrdbenzyl)-2H-tetrazole;
l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazoIe;
l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole; 5- [i- (2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (2,5-dichlorophenyl)-l H-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (2,6-dichlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzyI)-2H-tetrazole;
5- [i- (3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyI)-2H-tetrazole;
5- [i- (3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (3,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (2-bromophenyl)-1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [1- (2-bromophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5- [i- ^3-bromophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [\- (3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;
5- ;i- (4-bromophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 1- ^4-br0mophenyl)-l H-pyrazol-4-yl]-l-(4-nitrobe zyl)-2H-tetrazole;
5- i- ^4-fluorophenyl)- 1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H etrazole;
5- \- (4-fluorophenyl)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzy l)-2H-tetrazole;
5- \- (2-fluorophenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- \- (2-tluorophenyl)-lH-pyrazol-4-yl]-l -(4-nitrobenzy l)-2H-tetrazole;
5- \- '2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- - (2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole,
5- 1- ,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- (2,4-dimethylphenyl)-l H-pyrazol-4-yl]-l -(4-nitrobenzy l)-2H-tetrazole;
5- j- ,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 1- ,5-dimethylphenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzy l)-2H-tetrazole;
5- Ί- (2,6-dimethylphenyl).-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 1- (2,6-dimethylphenyl)-l H-pyrazol-4-yl]-l -(4-nitrobenzy l)-2H-tetrazole;
5- 1- ,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 1- ,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5- Ί- (3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 1- (3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l -(4-nitrobenzy l)-2H-tetrazole;
5- 1- (2-ethylphenyl)-l H-pyrazol-4-yl]-2 -(4-nitrobenzy l)-2H-tetrazole;
5- 1- (2-ethylphenyl)-lH-pyrazol-4-yl]-l -(4-nitrobenzy l)-2H-tetrazole;
5- 1- (4-ethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; - l -(4-ethylphenyl)-l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole;
- 1 -(4-methoxypheny 1)- 1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
- 1 -(4-methoxypheny I)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;
- 1 -(2-methy Ipheny I)- lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
- 1 -(2-methy Ipheny 1)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzy l)-2H-tetrazole;
- 1 -(4-methylphenyl)- 1 H-pyrazol-4-yl]-2-(4-nitrobenzy l)-2H-tetrazole;
- 1 -(4-methylphenyl)- l H-pyrazol-4-yl]- 1 -(4-nitrobenzy l)-2H-tetrazole;
-' chloro- 1 -methyl- 1 H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
chloro- 1 -methyl- 1 H-pyrazol-4-yl)- 1 -(4-nitrobenzyl)-2H-tetrazole;
- chloro- 1 -ethyl- 1 H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
- chloro- 1 -ethyl- 1 H-pyrazol-4-yl)- 1 -(4-nitrobenzy l)-2H-tetrazole;
- chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;- chloro- 1 -(2-methy lpropyl)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzy l)-2H-tetrazole;- benzyl-5-chloro-l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
- benzyl-5-chloro-l H-pyrazol-4-yl)-l-(4-nitrobenzyl)-2H-tetrazole;
- ■chloro- -phenyl- 1 H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
- ■chloro- •phenyl- 1 H-pyrazol-4-y l)-2-(4-nitrobenzy l)-2H-tetrazole;
- •chloro- 2-chloropheny 1)- 1 H-pyrazol-4-y l]-2- -nitrobenzyl)-2H-tetrazole;- ■chloro- 2- chlorophenyl)- 1 H-pyrazol-4-yl]- 1■ -nitrobenzyI)-2H-tetrazole;- ■chloro- 3- chlorophenyl)-l H-pyrazol-4-yl]-2- -nitrobenzyl)-2H-tetrazole;- ■chloro- 3- chlorophenyl)- 1 H-pyrazol-4-yl]- 1■ -nitrobenzyl)-2H-tetrazole;- ■chloro- 4- chloropheny 1)- 1 H-pyrazol-4-yl]-2- -nitrobenzyl)-2H-tetrazole;- -chloro- 4-chloropheny 1)- 1 H-pyrazol-4-y 1]- 1■ -nitrobenzyl)-2H-tetrazole;- ■chloro- 2,3-dichlorophenyl l H-pyrazol-4-yl 2-(4-nitrobenzyl)-2H-tetrazole- -chloro- 2.3- dichlorophenyl 1 H-pyrazol-4-yl 1 -(4-nitrobenzyl)-2H-tetrazoIe- -chloro- 2.4- dichlorophenyl l H-pyrazol-4-yl 2-(4-nitrobenzyl)-2H-tetrazole- ■chloro- 2.4- dichlorophenyl l H-pyrazol-4-yl 1 -(4-nitrobenzyl)-2H-tetrazole- •chloro- 2.5- dichlorophenyl l H-pyrazol-4-yl 2-(4-nitrobenzyl)-2H-tetrazole- ■chloro- 2.5- dichlorophenyl l H-pyrazol-4-yl 1 -(4-nitrobenzyl)-2H-tetrazole- •chloro- 2.6- dichlorophenyl l H-pyrazol-4-yl 2-(4-nitrobenzyl)-2H-tetrazole- ■chloro- 2,6-dichlorophenyl l H-pyrazol-4-yl 1 -(4-nitrobenzyl)-2H-tetrazole- ■chloro- 3,4-dichlorophenyl l H-pyrazol-4-yl 2-(4-nitrobenzyl)-2H-tetrazole- ■chloro- 3,4-dichlorophenyl 1 H-pyrazol-4-yl 1 -(4-nitrobenzyl)-2H-tetrazole ■chloro-l -(3,5-dichloropheny])- lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
■chloro-l -(3,5-dichlorophenyl)-l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
•(2-bromophenyl)-5-chloro- l H-pyrazol-4-.yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5 ■(2-bromophenyl)-5-chloro- l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole; 5 -(3-bromophenyl)-5-chloro- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5 •(3-bromophenyl)-5-chloro- l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole; 5 ■(4-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5 -(4-bromophenyl)-5-chloro- l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole; 5 -chloro- 4-fluorophenyl)- l H-pyrazol-4-y ]-2-(4-nitrobenzyl)-2H-tetrazole; 5 -chloro- 4-fluoropheny 1)- 1 H-pyrazol-4-y ]-l-(4-nitrobenzyl)-2H-tetrazole; 5 -chloro- 2-fluorophenyl)- 1 H-pyrazol-4-y ]-2-(4-nitrobenzyl)-2H-tetrazole; 5 -chloro- 2-fluorophenyl)- 1 H-pyrazol-4-y ]- l -(4-nitrobenzyI)-2H-tetrazole; 5 -chloro- 2,3-dimethylphenyl 1 H-pyrazo -4-yl]-2-(4-nitrobenzyl)-2H-tetrazole 5 -chloro- 2.3- dimethylphenyl 1 H-pyrazo -4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole 5 ■chloro- 2.4- dimethylphenyl 1 H-pyrazo -4-yl]-2-(4-nitrobenzyl)-2H-tetrazo|e 5 -chloro- 2.4- dimethylphenyl 1 H-pyrazo -4-yl]- l -(4-nitrobenzyl)-2H-tetrazole 5 -chloro- 2.5- dimethylphenyl 1 H-pyrazo -4-yl]-2-(4-nitrobenzyl)-2H-tetrazole 5 -chloro- 2.5- dimethy [phenyl 1 H-pyrazo -4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole 5 ■chloro- 2.6- dimethylphenyl 1 H-pyrazo -4-yl]-2-(4-nitrobenzyl)-2H-tetrazole 5 ■chloro- 2,6-dimethylphenyl 1 H-pyrazo -4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole 5 -chloro- 3,4-dimethylphenyl 1 H-pyrazo -4-yl]-2-(4-nitrobenzyl)-2H-tetrazole 5 -chloro- 3.4- dimethylphenyl 1 H-pyrazo -4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole 5 -chloro- 3.5- dimethylphenyl 1 H-pyrazo -4-yl]-2-(4-nitrobenzyl)-2H-tetrazole 5 -chloro- 3,5-dimethylphenyl 1 H-pyrazo -4-yl]-l -(4-nitrobenzyl)-2H-tetrazole 5 ■chloro- 2-ethylphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5 ■chloro- 2-ethylphenyl)-l H-pyrazoI-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole; 5 -chloro- 4-ethylphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5 -chloro- 4-ethylphenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;
-chloro- 4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; -chloro- 4-methoxyphenyl)-l H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole; •chloro- 2-methylphenyl)- 1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; -chloro- 2-methylphenyl)-l H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole; -chloro- 4-methylpheriyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5- 5-chloro- l -(4-methylphenyl)-l H-pyrazol-4-yl]-l -(4-nitrpbenzyl)-2H-tetrazole;
5- 5-bromo- 1 -methyl- l H-pyrazol-4-yI)-2-(4-nitrobenzyl)-2H-tetrazole;
5- 5-bromo- l -methyl-l H-pyrazol-4-yl)-l-(4-nitrobenzyl)-2H-tetrazole;
5- 5-bromo- 1 -ethyl- l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5 5-bromo- 1 -ethyl- lH-pyrazol-4-yl)- l-(4-nitrobenzyl)-2H-tetrazole;
5 5-bromo- 1 -(2-methylpropyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5 5-bromo- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;
5 1 -benzyl- 5-bromo- l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5- 1 -benzyl- 5-bromo- 1 H-pyrazol-4-y 1)- 1 -(4-nitrobenzy l)-2H-tetrazole;
5- 5-bromo- -phenyl- l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5- 5-bromo- -phenyl- l H-pyrazol-4-yl)-l -(4-nitrobenzyl)-2H-tetrazole;
5- 5-bromo- 2-chloropheny 1)- 1 H-pyrazol-4-yl]-2 4-nitrobenzy l)-2H-tetrazole;
5- 5-bromo- 2- chloropheny 1)- 1 H-pyrazol-4-yl]- 1 4-nitrobenzy l)-2H-tetrazole;
5- 5-bromo- 3- chloropheny 1)- 1 H-py razol-4-yl]-2 4-nitrobenzy l)-2H-tetrazole;
5- 5-bromo- 3- chlorophenyl)- 1 H-pyrazol-4-yl]- 1 4-nitrobenzy l)-2H-tetrazole;
5- 5-bromo- 4- chlorophenyl)-l H-pyrazol-4-yl]-2 4-nitrobenzy l)-2H-tetrazole;
5- 5-bromo- 4-chIorophenyl)- l H-pyrazol-4-yl]-l 4-nitrobenzy I)-2H-tetrazole;
5- 5-bromo- 2,3-dichlorophenyl l H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5- 5-bromo- 2.3- dichlorophenyl 1 H-pyrazol-4-yl - 1 -(4-nitrobenzy l)-2H-tetrazole
5- 5-bromo- 2.4- dichlorophenyl l H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5- 5-bromo- 2.4- dichlorophenyi 1 H-pyrazol-4-yl - 1 -(4-nitrobenzy l)-2H-tetrazole
5- 5-bromo- 2.5- dichlorophenyl l H-pyrazol-4-yl -2-(4-nitfobenzyl)-2H-tetrazole
5- 5-bromo- 2.5- dichlorophenyl l H-pyrazol-4-yl - 1 -(4-nitrobenzyl)-2H-tetrazole
5- 5-bromo- 2.6- dichlorophenyl l H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5- 5-bromo- 2,6-dichlorophenyl 1 H-pyrazol-4-yl - l -(4-nitrobenzyl)-2H-tetrazole 5-bromo- 3,4-dichlorophenyl l H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole 5-bromo- 3.4- dichlorophenyl l H-pyrazol-4-yl - 1 -(4-nitrobenzy I)-2H-tetrazole 5-bromo- 3.5- dichlorophenyl l H-pyrazolr4-yl -2-(4-nitrobenzyl)-2H-tetrazole 5-bromo- 3,5-dichlorophenyl l H-pyrazol-4-yl -1 -(4-nitrobenzy l)-2H-tetrazole 5-bromo- 2-bromophenyl)-l H-pyrazol-4-yl]-2- 4-nitrobenzy l)-2H-tetrazole; 5-bromo- 2- bromophenyl)- 1 H-pyrazol-4-y 1]- 1■ 4-nitrobenzy l)-2H-tetrazole; 5-bromo- 3- bromophenyl)-l H-pyrazol-4-yl]-2- 4-nitrobenzy l)-2H-tetrazole; 5-bromo- 3-bromophenyl)-l H-pyrazol-4-yl]- l - 4-nitrobenzy l)-2H-tetrazole; 5- bromo- 4-bromophenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5-, bromo- 4-bromophenyl)-l H-pyrazol-4-yl]- l-(4-nitrobenzyl)-2H-tetrazole; 5-1 -bromo- 4-fluorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5- -bromo- 4-fluorophenyl)- lH-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole; 5- -bromo- 2-fluorophenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5- bromo- 2-fluorophenyl)- l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole; 5- bromo- 2,3-dimethylphenyl)- H-pyrazol-4-yl -2- (4-ti trobenzyl)-2H-tetrazole 5- bromo- 2.3- dimethylphenyl)- H-pyrazol-4-y - 1 - (4-n trobenzyl)-2H-tetrazole 5- bromo- 2.4- dimethylphenyl)- H-pyrazol-4-yl -2- (4-n trobenzyl)-2H-tetrazole 5- bromo- 2.4- dimethylphenyl)- H-pyrazol-4-y -1 - (4-n trobenzyl)-2H-tetrazole 5- bromo- 2.5- dimethylphenyl)- H-pyrazol-4-y -2- (4-n trobenzyl)-2H-tetrazole 5- bromo- 2.5- dimethylphenyl)- H-pyrazol-4-yl -1- (4-n trobenzyl)-2H-tetrazole 5- -bromo- 2.6- dimethylphenyl)- H-pyrazol-4-yl -2- (4-n tro benzy 1 )-2 H -tetrazo 1 e 5- bromo- 2,6-dimethylphenyl)- H-pyrazol-4-y -1 - (4-n trobenzyl)-2H-tetrazole 5- bromo- 3,4-dimethylphenyl)- H-pyrazol-4-yl" -2- (4-n trobenzy l)-2 H -tetrazole 5- bromo- 3.4- dimethylphenyl)- H-pyrazol-4-y - 1 - (4-n trobenzyI)-2H-tetrazole 5- bromo- 3.5- dimethylphenyl)- H-pyrazol-4-yl i -2- (4-n trobenzy l)-2H-tetrazole 5- bromo- 3,5-dimethylphenyl)- H-pyrazol-4-yl]- 1 -(4-n trobenzyl)-2H-tetrazole 5- bromo- 2-ethylphenyl)- l H-pyrazol-4-yI]-2-(4-nitrobenzyl)-2H-tetrazole; 5- bromo- 2-ethylphenyl)- l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole; 5- bromo- 4-ethylphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5- bromo- 4-ethylphenyl)- l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole; 5- bromo- 4-methoxyphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5- bromo- 4-methoxypheny 1)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzy l)-2H-tetrazole; 5- bromo- 2-methylphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; 5- bromo- 2-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzy l)-2H-tetrazole; 5- bromo- 4-methylphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; ■5- bromo- 4-methylphenyl)-l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole; 5 iodo-1 -methyl- l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5 iodo-l-methyl-l H-pyrazol-4-yl)-l -(4-nitrobenzyl)-2H-tetrazole;
5 ethyl-5-iodo-l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5 ethyl-5-iodo-l H-pyrazol-4-yl)-l -(4-nitrobenzyl)-2H-tetrazole;
5 iodo-1 -(2-methylpropyl)- ] H-pyrazol-4-yl]-2-(4-nitrobenzyI)-2H-tetrazole; 5- -iodo- l -(2-methylpropyl)- l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole;
5- -benzyl-5-iodo-l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5- ■benzyl-5-iodo-l H-pyrazol-4-yl)- l -(4-nitrobenzyl)-2H-tetrazole;
5- ■iodp-1 -phenyl- l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5- •iodo- 1 -phenyl- 1 H-pyrazol-4-y 1)- 1 -(4-nitrobenzyl)-2H-tetrazole;
5- 2-chlorophenyI)-5-iodo- 1 H-pyrazol-4-yl]-2-' 4-nitrobenzyl)-2H-tetrazole;
5- 2- chlorophenyl)-5-iodo-l H-pyrazol-4-yl]- l - 4-nitrobenzyl)-2H-tetrazole;
5- 3- chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2 4-nitrobenzyl)-2H-tetrazole;
5-[ 3- chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 4-nitrobenzyl)-2H-tetrazole;
5- 4- chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2 4-nitrobenzyl)-2H-tetrazole;
5· 4-chlorophenyl)-5-iodp-l H-pyrazol-4-yl]- l 4-nitrobenzyl)-2H-tetrazole;
5-1 2,3-dichlorophenyl)-5- odo- H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5- 2.3- dichlorophenyl)-5- odo-l H-pyrazol-4-yl - l-(4-nitrobenzyl)-2H-tetrazole
5- 1 - 2.4- dichlorophenyl)-5- odo-l H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5- 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl - l -(4-nitrobenzyl)-2H-tetrazole
5- 2.5- dichlorophenyl)-5- odo-1 H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5- 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y I - 1 -(4-nitrobenz'y l)-2H-tetrazole
5- I - 2.6- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y I -2-(4-nitrobenzyl)-2H-tetrazole
5- 2,6-dichlorophenyl)-5- odo-1 H-pyrazol-4-yl -l -(4-nitrobenzyl)-2H-tetrazole
5- 3,4-dichlorophenyl)-5 odo- 1 H-pyrazol-4-y 1 -2-(4-nitrobenzyl)-2H-tetrazole
5- 3.4- dichlorophenyl)-5 odo- 1 H-pyrazol-4-y I - 1 -(4-nitrobenzy l)-2H-tetrazole
5- 3.5- dichlorophenyl)-5 odo- 1 H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5-1 3,5-dichlorophenyl)-5 odo-1 H-pyrazol-4-yl - l -(4-nitrobenzyl)-2H-tetrazole
5- 2-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2 4-nitrobenzyl)-2H-tetrazole
5-1 2- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-l 4-nitrobenzyl)-2H-tetrazole
5- 3- bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2 4-nitrobenzy l)-2H-tetrazole
5- 3- bromophenyl)-5-iodo- l H-pyrazol-4-yl]-l 4-nitrobenzy l)-2H-tetrazole
5- 4- bromophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2 4-nitrobenzy l)-2H-tetrazole
5- 4-bromophenyl)-5-iodo-l H-pyrazol-4-yl]- l 4-nitrobenzy l)-2H-tetrazole
5- 4-fluorophenyl)-5^iodo-l H-pyrazol-4-yl]-2- 4-nitrobenzy l)-2 H-tetrazole;
5- 4-fluorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 4-nitrobenzyl)-2H-tetrazole;
5- 2-fluorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2 4-nitrobenzy l)-2 H-tetrazole;
5- 2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-l 4-nitrobenzy l)-2H-tetrazole; 2,3-dimethylphenyl)-5- odo- 1 H -pyrazol -4-yl -2-(4-nitrobenzyl)-2H-tetrazole
2.3- dimethylphenyl)-5- odo- 1 H -pyrazol -4-yl - 1 -(4-n itrobenzy l)-2 H-tetrazole
2.4- dimethylphenyl)-5- odo- 1 H -pyrazol -4-yl -2-(4-nitrobenzyl)-2H-tetrazole
2.4- dimethylphenyI)-5- odo- 1 H -pyrazol -4-yl - 1 -(4-nitrobenzy l)-2H-tetrazole
2.5- dimethylphenyl)-5- odo- l H- -pyrazol -4-yl -2-(4-nitrobenzyl)-2H-tetrazole
2.5- dimethylphenyl)-5- odo- 1 H -pyrazol -4-yl -l -(4-nitrobenzyl)-2H-tetrazole
2.6- dimethylphenyl)-5- odo- 1 H -pyrazol -4-yl -2-(4-nitrobenzyl)-2H-tetrazole 2,6-dimethylphenyl)-5- odo- 1 H- -pyrazol -4-yl - 1 -(4-nitrobenzy I)-2H-tetrazole 3,4-dimethylphenyl)-5- odo- 1 H- -pyrazol -4-yl -2-(4-nitrobenzyl)-2H-tetrazole
3.4- dimethylphenyl)-5- odo- 1 H -pyrazol -4-yl -l -(4-nitrobenzyl)-2H-tetrazole
3.5- dimethylphenyl)-5- odo- 1 H -pyrazol -4-yl -2-(4-nitrobenzyl)-2H-tetrazole
3,5-dimethylphenyl)-5- odo-l H-pyrazoI-4-yl] - 1 -(4-nitrobenzy l)-2H-tetrazole l -(2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
l -(2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
l -(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
l -(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]- l -(4-nitrobenzy l)-2H-tetrazole;
5-iodo- l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-iodo- 1 -(4-methoxypheny 1)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzy l)-2H-tetrazole;
5-iodo-l-(2-methylphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-iodo- l -(2-methylphenyl)-l H-pyrazol-4-yl]- l -(4-nitrobenzy l)-2H-tetrazole;
5-iodo- l -(4-methylphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; or
5-iodo- 1 -(4-methylphenyl)-l H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole.
The present disclosure further provides a process for preparing substituted tetrazole compounds, its derivatives, salts, stereo- isomers, or regio-isomers thereof of formula 1,
Figure imgf000079_0001
wherein:
Ri is selected from H, CI, Br or I; R.2 is selected from hydrogen or a straight chain or a branched C] .7 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C i_5 alkyl, phenyl, or a C1 -C4 alkoxy;
R3 is selected from a straight or a branched chain C 1-7 alkyl; or a C6-C 14 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C | -5 alkyl, phenyl, or a C 1 -C4 alkoxy;
said process comprising:
Figure imgf000080_0001
treating a compound of formula II with a reagent and an organic solvent selected from Ν,Ν-dimethylformamide, N,N-dimethylacetam ide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran, toluene, xylene, benzene or water to obtain a compound of formula I with R2 as hydrogen, its derivatives, salts, stereo-isomers, or regio-isomers thereof; wherein,
Ri is selected from H, CI, Br or 1;
R3 is selected from a straight or a branched chain 1 -7 alkyl; or a C6-C 14 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C1.5 alkyl, phenyl, or a C 1 -C4 alkoxy; and s aid reagent is selected from an optionally substituted sodium azide in the presence of either an ammonium halide such as ammonium chloride, ammonium bromide or ammonium iodide or a tri-n-butyl tin halide such as tri- n-butyl tin chloride, tri-n-butyl tin bromide or tri-n- butyl tin iodide; and
optionally alkylating the above compound of formula I with a dialkyl sulfate or alkyl halide such as methyl iodide or methyl bromide, in presence of a base selected from an alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di- isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline, to obtain a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, wherein R2 is selected from a straight chain or a branched C i_7 alkyl.
Another embodiment of the present disclosure provides a process for preparing a substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof of formula I, comprising:
treating a compound of formula Π with an optionally substituted sodium azide in the presence of either an ammonium halide, such as ammonium chloride, ammonium bromide or ammonium iodide; and a polar solvent selected from N,N-dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrroIidone or water or a tri-n-butyl tin halide such as tri-n- butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide in presence of a non polar solvent such as toluene, xylene or benzene, to obtain a compound of formula 1, its derivatives, salts, stereo-isomers, or regio-isomers thereof, wherein R2 is hydrogen.
Another embodiment of the present disclosure provides a process for preparing a substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof of formula I, comprising:
Figure imgf000081_0001
Formula III
treating a compound of formula III with sodium nitrite and cuprous halide selected from cuprous chloride, cuprous bromide or cuprous iodide, with a. m ineral acid selected from hydrochloric acid, hydrobromic acid, or sulfuric acid, to obtain a compound of formula I I; wherein
3 is selected from a straight or a branched chain C | -7 alkyl; or a C6-C 14 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C1.5 alkyl, phenyl, or a C1 -C4 alkoxy; and treating the compound of formula II with a substituted sodium azide in the presence of either an ammonium halide such as ammonium chloride, ammonium bromide or ammonium iodide; and a polar solvent selected from N,N-dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, or water, or a tri-n-butyl tin halide such as tri- n-butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide in presence of a non polar solvent such as toluene, xylene or benzene, to obtain the compound of formula I, its derivatives, salts, stereo-isomers, regio-isomers thereof, wherein R2 is hydrogen.
Yet another embodiment of the present disclosure provides a process for preparing a substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof of formula I, comprising:
treating malononitrile with a compound of formula V in presence of acetic anhydrid
Figure imgf000082_0001
Formula V, Formula IV
wherein R4 is independently selected from a straight or a branched C alkyl; treating the compound of formula IV with an optionally substituted N-alkyl hydrazine sulfate, or an optionally substituted N-alkyl hydrazine, or an optionally substituted N-aryl hydrazine sulfate, or an optionally substituted N-aryl hydrazine, and a base selected from an alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N- dimethylaniline, in the presence of an alcohol selected from methanol, ethanol or propanol to obtain a compound of formula III,
Figure imgf000082_0002
Formula III wherein R3 is selected from a straight chain or a branched chain C alky 1 or a Ce aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, C | -2 alkyl, phenyl or C|_c4 alkoxy;
treating the compound of formula III with sodium nitrite and cuprous halide selected from cuprous chloride, cuprous bromide or cuprous iodide, with a mineral acid selected from hydrochloric acid, hydrobromic acid, or sulfuric acid, to obtain a compound of formula II;
treating the compound of formula II with sodium azide in the presence of either an ammonium halide selected from ammonium chloride, ammonium bromide or ammonium iodide; and a polar solvent selected from Ν,Ν-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, or water, or a tri-n-butyl tin hal ide such as tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide in presence of a non polar solvent such as toluene, xylene or benzene, to obtain a compound of formula 1 , its derivatives, salts, stereoisomers, regio-isomers thereof wherein R2 is hydrogen.
Still another embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivative, salt, stereoisomer, regioisomer thereof, comprising: treating a compound of formula II with an optionally substituted sodium azide in the presence of either an ammonium halide such as ammonium chloride, ammonium bromide or ammonium iodide, and a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, or water; or a tri-n-butyl tin hal ide such as tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide in presence of a non polar solvent such as toluene, xylene or benzene, to obtain a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof wherein R2 is hydrogen; and
alkylating the above compound of formula I with a dialkyl sulfate, or alkyl halide such as methyl iodide or methyl bromide in presence of a base selected from an alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or l ithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or Ν,Ν-dimethylaniline, in the presence of a polar solvent N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N- methylpyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran or water, to obtain a compound of formula I, its derivatives, salts, stereoisomers, regio-isomers thereof wherein R2 is selected from a straight chain or a branched C | .7 alkyl.'
Further, an embodiment of the present disclosure provides a process preparing a substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof of formula I, comprising: treating malononitrile with a compound of formula V in presence of
Figure imgf000084_0001
Formula V, Formula IV
wherein R4 is selected from a straight or a branched C 1.4 alkyl; treating the compound of formula IV with an optionally substituted N-alkyl hydrazine sulfate, or an optionally substituted N-aryl hydrazine sulfate, and a base selected from an alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N- dimethylaniline, in the presence of an alcohol selected from methanol, ethanol or propanol to obtain a compound of formula III,
Figure imgf000084_0002
Formula I I I
wherein R3 is selected from a straight chain or a branched chain C alkyl or a Ce aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, C i -2 alkyl, phenyl or Ci_c4 alkoxy;
treating the compound of formula III with sodium nitrite and cuprous hal ide selected from cuprous chloride, cuprous bromide or cuprous iodide, with a m ineral acid selected from hydrochloric acid, hydrobromic acid, or sulfuric acid, to obtain a compound of formula Π;
treating the compound of formula II with sodium azide in the presence of either an ammonium halide selected from ammonium chloride, ammonium bromide or ammonium iodide; and a polar solvent selected from Ν,Ν-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, or water; or a tri-n-butyl tin halide such as tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide in presence of a non polar solvent such as toluene, xylene or benzene, to obtain a compound of formula I, its derivatives, salts, stereoisomers, regio-isomers thereof wherein R2 is hydrogen; and
alkylating the compound of formula I, wherein R2 is hydrogen, with a dialkyl sulfate, or alkyl halide such as methyl iodide or methyl bromide in presence of a base selected from an alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N- dimethylaniline, in the presence of a polar solvent Ν,Ν-dimethylformamide, N,N- dimethylacetamide, N -methylpyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2- dichloroethane, methanol, tetrahydrofuran or water, to obtain a compound of formula I, its derivatives, salts, stereo-isomers, regio-isomers thereof wherein R2 is selected from a straight chain or a branched Q.y alkyl.
Another embodiment of the present disclosure provides a process for preparing a substituted tetrazole compounds, its derivatives, salts, stereo-isomers, or regio-isomers thereof of formula I, comprising:
treating 5-chloro- l -methyl-lH-pyrazole-4-carbonitrile compound with sodium azide in the presence of either ammonium chloride, and Ν,Ν-dimethylformamide, or tri-n-butyl tin chloride and toluene to obtain 5-(5-chloro- l -methyl- lH-pyrazol-4-yl)-2H-tetrazoIe) of - formula I.
Another embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivative, salt, stereoisomer, or regioisomer thereof, comprising:
treating 5-chloro- l -methyl-lH-pyrazole-4-carbonitrile compound with sodium azide in the presence of either ammonium chloride^ and Ν,Ν-dimethylformamide; or tri-n-butyl tin chloride and toluene, to obtain 5-(5-chloro-l -methyl- lH-pyrazoi-4-yl)-2H-tetrazoIe) of formula I, wherein 2 is hydrogen; and
methylating 5-(5-chloro- l -methyl-lH-pyrazol-4-yl)-2H-tetrazole) with dimethyl sulfate and potassium carbonate in the presence of acetone, to obtain 5-(5-chloro-l -methyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole of formula I; wherein R2 is a methyl group.
The present disclosure further provides a process preparing a substituted tetrazole compounds, its derivatives, salts, stere or regio-isomers thereof of formula I,
Figure imgf000086_0001
Formula 1
wherein:
Ri is selected from Η, CI, Br or I;
R2 is selected from hydrogen or a straight chain or a branched C|-7 alkyl; wherein said alkyl is optionally substituted with phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C 1 -5 alkyl, phenyl, or a C 1 -C4 alkoxy; and
R3 is selected from a straight or a branched chain Ci-7 alkyl; or a C6-C 1 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C 1 -5 alkyl, phenyl, or a C 1 -C4 alkoxy;
said process comprising:
reacting a compound of formula VII with an alkylating agent such as alkyl halide, or dialkyl sulfate in the presence of a base selected from alkali metal hydroxide base, such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or organic bases such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or Ν,Ν-dimethylaniline, to obtain a compound of formula VI;
Figure imgf000087_0001
Formula VII Formula VI wherein:
R3 is selected from a straight or a branched chain Ci-7 alkyl; or a C6-C|4 aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, Ci-5 alkyl, phenyl, or a C, -C4 alkoxy; and
halogenating the compound of formula VI with a halogenating agent selected from N- chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in the presence of polar solvent selected from N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methyl-2- pyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran, ethyl acetate, or butyl acetate, to obtain the compound of formula I.
In an aspect of the present disclosure, the compound of formula VII is prepared by a process comprising:
treating a compound of formula X with phosphoryl chloride in the presence of a polar solvent selected from N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methyl-2 - pyrrolidone, acetonitrile, dichloromethane, 1,2-dichloroethane, or tetrahydrofuran, to obtain a compound of formula IX;
Figure imgf000087_0002
Formula X Formula IX
wherein:
. R3 is selected from a straight or a branched chain C|_ alkyl; or a C6-Ci4 aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; . said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C|-5 alkyl, phenyl, or a CrC4 alkoxy;
treating the compound of formula IX with hydroxylamine hydrochloride in the presence of an alcohol selected from methanol, ethanol or propanol, to obtain a compound of formula VIII; and
Figure imgf000088_0001
Formula VIII
treating the compound of formula VIII with sodium azide in the presence of ammonium chloride and a polar solvent selected from Ν,Ν- dimethylformamide, N,N- dimethylacetamide, N -methyl-2-pyrrolidone, tetrahydrofuran or water, to obtain the compound of formula VII.
In another aspect of the present disclosure, the compound of formula VI I is prepared by a process comprising:
treating a compound of formula X with iodine and a strong oxidizing agent such as hydrogen peroxide in aqueous medium to obtain a compound of formula XII;
Figure imgf000088_0002
Formula X Formula XII
wherein:
R.3 is selected from a straight or a branched chain C |_7 alkyl; or a C6-C 14 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C I -5 alkyl, phenyl, or a C 1 -C4 alkoxy;
treating the compound of formula XII with either
potassium ferrocyanide and palladium (II) acetate in the presence of a base selected from alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base selected from sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; and a polar solvent selected from N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N- methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran or water; or
sodium cyanide or copper cyanide in the presence of cuprous halides such as cuprous iodide and Ν,Ν-dimethyl ethylene diamine with a non polar solvent such toluene, xylene, or benzene,
to obtain a compound of formula XI; and
Figure imgf000089_0001
Formula XI
treating the compound of formula XI with sodium azide and either tri-n-butyl tin chloride in the presence of a non polar solvent selected from toluene, xylene or benzene; or ammonium chloride and Ν,Ν-dimethylformamide, to obtain the compound of formula VII.
An embodiment of the present disclosure provides a process for preparing a compound of formula I, its derivative, salt, stereoisomer, or regioisomer thereof, comprising:
reacting 5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole; and
chlorinating 2-methyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole with N- chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro- l -methyl- l H-pyrazol- 4-yl)-2-methyl-2H-tetrazole of formula I. Yet another embodiment of the present disclosure provides a process for preparing 5-(5-chloro- l -methyl- lH-pyrazole-4-yl)-2-methyl-2H-tetrazole of formula I by a process comprising:
treating 1 -methyl- lH-pyrazole with phosphoryl chloride in the presence of N,N- dimethylformamide, to obtain a 1 -methyl- lH-pyrazole-4-carbaldehyde;
treating the l -methyl-lH-pyrazole-4-carbaldehyde with hydroxylamine hydrochloride in the presence of ethanol, to obtain a 1 - methyl - lH-pyrazole-4-carbaldehyde oxime;
treating the 1 -methyl- lH-pyrazole-4-carbaldehyde oxime with sodium azide in the presence of ammonium chloride and Ν,Ν-dimethylformamide, to form the 5-(l -methyl- 1H- pyrazole-4-yl)-2H-tetrazole;
reacting 5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l -methyl-lH-pyrazol-4-yl)-2H-tetrazole; and
chlorinating 2-methyl-5-( l -methyl- l H-pyrazol-4-yl)-2H-tetrazole with N- chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l -methyl- lH-pyrazol- 4-yl)-2-methyl-2H-tetrazole of formula I.
Another embodiment of the present disclosure provides a process for preparing 5-(5- chIoro-l -methyl- lH-pyrazole-4-yl)-2-methyl-2H-tetrazole of formula I by a process comprising:
treating 1 -methyl- lH-pyrazole with iodine and hydrogen peroxide in aqueous medium to obtain a 4-iodo- l -methyl- lH-pyrazoje;
treating 4-iodo- l -methyl-lH-pyrazole with potassium ferrocyanide and palladium (II) acetate in the presence of sodium carbonate, and Ν,Ν-dimethylacetamide, to obtain a 1 - methyl- l H-pyrazole-4-carbonitrile;
treating 1 -methyl- l H-pyrazole-4-carbonitrile with sodium azide and either with tri- n-butyl tin chloride in the presence of toluene, or ammonium chloride in the presence of Ν,Ν-dimethylformamide to obtain the 5-(l-methyl-lH-pyrazol-4-yl)-2H-tetrazole;
reacting 5-(l -methyl- l H-pyrazole-4-yl)-2H-tetrazole with methyl iodide and . dimethyl sulphate, in the presence of potassium hydroxide arid potassium carbonate to obtain 2-methyl.-5-( l -methyl- lH-pyrazol-4-yl)-2H-tetrazole; and chlorinating 2-methyI-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole with N- chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro- l -methyl- lH-pyrazol- 4-yl)-2-methyl-2H-tetrazole of formula I.
The substituted tetrazole compounds of formula I, its derivatives, salts, stereoisomers, or regio-isomers thereof may be prepared following independent general synthetic routes as outlined in the Schemes 1 -4.
Scheme 1: General route for the synthesis of compounds of formula (1) its derivatives, salts, stereo-isomers, regio-isomers
Figure imgf000091_0001
(1)
The compound of. formula 1, as above is prepared either from reaction of the compound of formula 11 with an optionally substituted sodium azide in the presence of an ammonium halide selected from ammonium chloride, ammonium bromide or ammonium iodide and a polar solvent selected from N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methyl-2- pyrrolidone, or water; or by reaction of the compound of formula I I with an optionally substituted sodium azide in the presence of a tri-n-butyl tin halide such as tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide in the presence of a non-polar solvent such as toluene, xylene or benzene. The reaction temperature range from 1 10°C to , 120°C.
In the compound of formula 1 above, R| is selected from Η, CI, Br or I; R2 is hydrogen; and R3 is selected from a straight or a branched chain C i -7 alkyl; or a C6-C 14 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C|-5 alkyl, phenyl, or a C 1 -C4 alkoxy.
Scheme 2: General route for the synthesis of compounds of formula (I) its derivatives, salts, stereo-isomers, or regio-isomers thereof.
Figure imgf000092_0001
(I) (I)
(1); wherein (I ); wherein R2 is
R2 = H selected from a
straight chain or
branched C | _7 alky 1
The compound of formula I, wherein R2 is hydrogen, as above is prepared from reaction of the compound of formula II by a process as described in Scheme 1 .
Compound of formula I thus obtained is alkylated with a dialkyl sulfate or alky 1 halide such as methyl iodide or methyl bromide and a base selected from alkali metal hydroxide base, such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di- isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylani line, in the presence of a polar solvent selected from N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N- methylpyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran or water, to yield a compound of formula I; wherein R2 is selected from a straight chain or a branched Ci -7 alkyl.
Scheme 3: General route for the synthesis of compounds of formula (1) its derivatives, salts, stereoisomers, regioisomers thereof,
Figure imgf000092_0002
(i ) ( I) Malononitrile is reacted with a compound of formula V, wherein all symbols are as defined below, to yield a compound of formula IV. The reaction is carried out using acetic anhydride at a temperature in the range of 105-1 10°C for 2 to 3 hours to provide a compound of formula IV.
The compound of formula IV is cyclized to obtain a compound of formula III by a cyclization reaction. The reaction is carried out with a suitable hydrazine such as N-alkyl hydrazine sulfate, N-alkyl hydrazine, N-aryl hydrazine sulfate, or N-aryl hydrazine, in the j
presence of a base selected from alkali metal hydroxide base selected from sodium hydroxide, potassium hydroxide or lithium hydroxide; alkali metal carbonate base selected from sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base selected from triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or Ν,Ν-dimethylaniline and an alcohol selected from methanol, ethanol or propanol for about 1 -2 hours at reflux temperature.
The compound of formula III is converted to a compound of formula II by treatment with a halogenating agent such as cuprous halide selected from cuprous chloride, cuprous bromide or cuprous iodide, and sodium nitrite in the presence of a mineral acid selected from hydrochloric acid, hydrobromic acid, or sulfuric acid at room temperature.
The compound of formula I, wherein R2 is hydrogen; is either prepared from reaction of the compound of formula II with an optionally substituted sodium azide in the presence of an ammonium halide selected from ammonium chloride, ammonium bromide or ammonium iodide and a polar solvent selected from Ν,Ν-dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, or water; or from reaction of the compound of formula II with an optionally substituted sodium azide in the presence of a tri-n-butyl tin halide such as tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide in the presence of a non-polar solvent such as toluene, xylene or benzene. The reaction temperature range from 1 10°C to 120 °C.
The compound of formula I thus obtained is alkylated with a dialkyl sulfate or alkyl halide such as methyl iodide or methyl bromide and a base selected from alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline in the presence of a polar solvent selected from Ν,Ν-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran or water to yield a compound of formula I; wherein R2 is selected from a straight chain or a branched Ci-7 alkyl;
Ri is selected from H, CI, Br or I; R2 is selected from hydrogen or a straight chain or a branched Ci_7 alkyl; wherein said alkyl is optionally substituted with phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C 1 -5 alkyl, phenyl, or a C 1 -C4 alkoxy; and
R3 is selected from a straight or a branched chain Ci_7 alkyl; or a C6-C 14 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, phenyl;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C alkyl, phenyl, or a Q -C4 alkoxy;
R4 is independently selected from a straight or a branched C I -4 alkyl.
Scheme 4: General route for the synthesis of compounds of formula (I) its derivatives, salts, stereo-isomers, or regio-isomers thereof,
A compou
Figure imgf000094_0001
the presence of a polar solvent selected from N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methyl-2- pyrrolidone, acetonitrile, dichloromethane, 1 ,2-dichloroethane, or tetrahydrofuran, wherein all symbols are defined above, to yield a compound of formula IX.
The compound of formula IX is converted to a compound of formula VIII by treatment with hydroxylamine hydrochloride in the presence of an alcohol selected from methanol, ethanol or propanol at reflux temperature. The compound of VI 1 is prepared from reaction of the compound of formula VIII with an ammonium halide selected from ammonium chloride, ammonium bromide or ammonium iodide, and an optionally substituted sodium azide. The reaction is carried out in a polar solvent selected from N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methyl- 2- pyrrolidone, tetrahydrofuran or water. The reaction temperature range from 1 10°C to 120 °C. '
The compound of formula VII is further reacted with an alkylating agent such as alky 1 halide, or dialkyl sulfate and in the presence of a base selected from alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or Ν,Ν-dimethylaniline, to obtain a compound of formula VI. Halogenating the compound of formula VI with a halogenating agent selected from N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in the presence of a pol ar · solvent selected from Ν,Ν-dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2- dichloroethane, methanol, tetrahydrofuran, ethyl acetate, or butyl acetate, yields the compound of formula I, wherein: R] is selected from H, CI, Br or 1; R2 is selected froni hydrogen or a straight chain or a branched C|.7 alkyl; wherein said alkyl is optionally substituted with phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C|_5 alkyl, phenyl, or a C 1 -C4 alkoxy; and '
R3 is selected from a straight or a branched chain Ci_7 alkyl; or a C6-C14 aryl group;
wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, phenyl;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C1.5 alkyl, phenyl, or a C 1 -C4 alkoxy.
Scheme 5: General route for the synthesis of compounds of formula (I) its derivatives, salts, stereoisomers, or regioisomers thereof,
Figure imgf000096_0001
Figure imgf000096_0002
A compound of formula X is reacted with iodine and a strong oxidizing agent such as hydrogen peroxide in aqueous medium to obtain a compound of formula XII; wherein all symbols are defined above.
The compound of formula XII is treated with either potassium ferrocyanide and palladium (II) acetate in the presence of a base selected from alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonates such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; and a polar solvent selected from Ν,Ν-dimethylformamide, N,N- dimethylacetamide, n-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2- dichloroethane, methanol, tetrahydrofuran or water; or the compound of formula XII is treated with sodium cyanide or copper cyanide in the presence of cuprous halides such as cuprous iodide and Ν,Ν-dimethyl ethylene diamine in the presence of a non polar solvent such toluene, xylene, or benzene to obtain a compound of formula XI.
The compound of formula XI is converted to a compound of formula VII by treatment with sodium azide and with either tri-n-butyl tin chloride in the presence of a non polar solvent selected from toluene, xylene or benzene; or by treatment with sodium azide with ammonium chloride and, N,N-dimethylformamide, to obtain the compound of formula VII.
The compound of formula VII is reacted with an alkylating agent such as alkyl halide, or dialkyl sulfate and in the presence of a base selected from alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or organic base such as triethyl amine, di-isopropyl a mine, di- isopropyl ethyl amine, pyridine, pyrrolidine or Ν,Ν-dimethylaniline, to obtain a compound of formula VI.
Halogenating the compound of formula VI with a halogenating agent selected from N-chlorosuccinimide, N-bromosuccihimide or N-iodosuccinimide in the presence of a polar solvent selected from N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methyl-2- pyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran, ethyl acetate, or butyl acetate, yields the compound of formula I.
Abbreviations
The following abbreviations are employed in the examples and elsewhere herein:
DMF: N,N-dimethylformamide,
DCE: Dichloroethane,
THF: Tetrahydrofuran,
AlC : Aluminium Chloride,
AlBr3 : Aluminium Bromide,
AII3 : Aluminium Iodide,
H202 : Hydrogen peroxide,
Ac20: Acetic anhydride,
DCM: Dichloromethane,
HC1: Hydrochloric acid,
DI water: De-ionized water,
DM water: Demineralized water,
M/C: Moisture content,
MR: Molar ratio,
T: Times,
MP: Melting point,
BP: Boiling point,
w/w: weight/weight .
Examples
The disclosure will now be illustrated with working examples, which is intended to illustrate the working of disclosure and not intended to take restfictively to imply any limitations on the scope of the present disclosure. All stereo-isomers or regio-isomers of the compounds of the instant disclosure are contemplated, either in admixture or in pure or substantially pure form.
Example 1: 5-(5-chloro-l-methyl-lH-pyrazol-4-yl)-2H-tetrazole (Compound 1):
5-chloro-l -methyl-lH-pyrazole-4-carbonitrile (13.0 gm, 0.092 moles), was dissolved in DMF (40 ml), followed by addition of ammonium chloride (9.9 gm, 0.184 moles) and sodium azide (12.0 gm, 0.184 moles) and stirred at 100- 140°C for 10- 16 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled at 0-5°C and quenched with aqueous HC1 (78.0 ml) and stirred for 30-60 min at 0-5°C. The solid material obtained was filtered, washed with cold DM water (40 ml) and dried at 60-65°C to yield the product, 5-(5-chloro-l -methyl-lH-pyrazole-4-yl)-2H-tetrazole.
Dry wt : 16.2 gm
Yield : 1 .25 w/w (96%)
HPLC purity : 99.26%
MP : 215-219°C
Example 2: Compound 1, 5-(5-chloro-l-methyI-lH-pyrazol-4-yl)-2H-tetrazole:
Step 1: 2-(ethoxymethylene)malononitrile
A mixture of triethyl orthoformate (67.3 gm, 0.454 moles) and malononitrile (20.0 gm, 0.302 moles) in acetic anhydride (77.2 gm, 0.75 moles) was refluxed for 4-5 hours at 1 10- 140°C. The reaction was monitored by GC . Reaction mixture was cooled to room temperature. Concentrated the reaction mixture at 70°C at reduced pressure to yield crude solid product, 2-(ethoxymethylene)malononitrile. The crude product was further purified either by vacuum distillation to yield pure product, 2-(ethoxymethylene)malononitrile. Dry wt : 36.0 gm
Yield : 1.80 w/w (98%)
HPLC purity : 99%
MP : 65-67 °C
Step 2: 5-amino- l -methyl- l H-pyrazole-4-carbonitrile
A solution of 2-(ethoxymethylene)malononitrile (20.0 gm, 0.163 moles) in methanol (80.0 ml) was slowly added to a mixture of N-methyl hydrazine sulfate (23.5 gm, 0.163 moles), triethyl amine (33.0 gm, 0.326 moles) and methanol (30.0 gm). The reaction mixture was refluxed for 1 -2 hour. The progress of the reaction was monitored by HPLC. Excess methanol was distilled out at reduced pressure. To the above residue, distilled water (40.0 ml) was added and the reaction mass was cooled to 0-15°C. 15% (w/v) aqueous sodium hydroxide solution ( 18.0 ml) was added to the above reaction mixture and the reaction mixture thereto was stirred for 30-45 min at 0-5°C, filtered, washed with cold water (400 ml) and air dried to yield 5-amino- l -methyl- lH-pyrazole-4-carbonitrile at 50-75°C.
Dry wt : 15.4 gm
Yield : 0.77 w/w (77%)
HPLC purity : 98.67%
MP : 216-221 °C
Step 3: 5-chloro- l -methyl- ] H-pyrazole-4-carbonitrile
A mixture of 5-amino- l -methyI- lH-pyrazole-4-carbonitrile ( 12.1 gm, 0.099 moles), hydrochloric acid (72.6 ml, strength: 35-37%) in DM water (60.0 ml) was stirred at room temperature. Reaction mixture was cooled to 0 to 5°C and sodium nitrite solution (by dissolving sodium nitrite (8.2 gm, 0.1 19 moles) in DI water (240 ml)) was slowly added. The reaction mixture was stirred for 1 - 1.5 hours at 0 to 5°C. Urea solution prepared by dissolving urea (1.2 gm) in DI water (6.0 ml)] is added slowly to the reaction mixture. Solid cuprous chloride ( 12.8 gm, 0.129 moles) was added to the above reaction mixture, stirred the reaction mixture for 3-4 hours at 0 to 5°C. Then the reaction temperature was raised to room temperature and stirred for 12- 18 hours. Progress of the reaction was monitored by HPLC. To the above reaction mixture was added DI water ( 120 ml) and 25% (w/v) aqueous sodium hydroxide solution (80.0 ml) to adjust the pH to 3-3.5. 1 ,2-dichloroethane was poured to the reaction mixture and stirred for 10-15 min at 45-50°C. The inorganic salt was filtered off through hyflo bed. The organic layer was separated and aqueous layer was extracted with 1 ,2-dichloroethane. The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (50.0 ml). The organic layer was evaporated to obtain the 5-chloro- l -methyl- lH-pyrazole-4-carbonitrile.
Dry wt : 1 1.8 gm
Yield : 0.97 w/w (84 %)
HPLC purity : 93.34%
MP : 5 -60°C
Step 4: 5-(5-chloro-l -methyl-lH-pyrazol-4-yl)-2H-tetrazole of formula I.
5-(5-chloro-l -methyl- lH-pyrazol-4-yl)-2H-tetrazole of formula I is prepared from the above product 5-chloro-l -methyl- l H-pyrazole-4-carbonitrile by the process as in example 1. Compounds 2-30 were prepared by following the experimental procedure of Example 1 and/ or 2 using appropriate intermediates.
Figure imgf000100_0001
23 CI H 2,6 5-[5-chloro-l -(2,6-dimethylphenyl)- lH-pyrazol-
(CH3)2C6H3 4-yl]-2H-tetrazole
24 CI H 3,4 5-[5-chloro-l-(3,4-dimethylphenyl)- lH-pyrazol-
(CH3)2C6H3 4-yl]-2H-tetrazole
25 CI H 3,5 5-[5-chloro- l-(3,5-dimethy phenyl)- lH-pyrazol-
(CH3)2C6H3 4-yl]-2H-tetrazole
26 CI H 2CH2CH3C6 5-[5-chloro- l -(2-ethylphenyl)- l H-pyrazol-4-yl]- H4 2H-tetrazole
27 CI H 4CH2CH3C6 5-[5-chloro-l -(4-ethylphenyl)- lH-pyrazol-4-yl]- H4 2H-tetrazole
28 CI H 40CH3C6H4 5-[5-chloro- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4- yl]-2H-tetrazole
29 · CI H 2 CH3C6H4 5-[5-chloro- l -(2-methylphenyl)- lH-pyrazol-4- yl]-2H-tetrazole
30 CI H 4 CH3C6H4 5-[5-chloro-l -(4-methylphenyl)-lH-pyrazol-4- yl]-2H-tetrazole
Example 3: 5-(5-bromo-l-methyl-lH-pyrazol-4-yl)-2H-tetrazole (Compound 31)
5-bromo- l -methyl-lH-pyrazole-4-carbonitrile, (14.85 gm, 0.0798 moles), was dissolved in toluene ( 148 ml), and tri-n-butyl tin chloride (64.83 gm, 0.199 moles) and sodium azide ( 12.93 gm, 0. 199 moles) was added to it. The reaction mixture was stirred at 100- 1 15°C for 7-8 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled at 10-15°C and 10% ethanolic HCl solution ( 100 ml) was added and stirred for 1 - 1 .5 hours at 10-15°C. The inorganic salt was filtered off, washed with ethanol (30 ml). Mother liquor and washings were collected and excess toluene and ethanol were recovered at 50- 55°C under reduced pressure. Poured di-isopropyl ether (100 ml) to the above residue and stirred the resulting solid for 1 -2 hours at 20-25°C. The solid product was filtered, washed with di-isopropyl ether (30 ml) and air dried to yield the product, 5-(5-bromo- l -methyl- 1 H- pyrazol-4-yl)-2H-tetrazole at 60-65°C. The melting point of the 5-(5-bromo- 1 -methyl- 1H- pyrazol-4-yl)-2H-tetrazole is 215-218°C.
Dry wt 16 gm
Yield 1 .07 w/w (87%)
HPLC purity 99.72%
MP 203-207°C
Example 4: 5-(5-bromo-l-methyl-lH-pyrazol-4-yl)-2H-tetrazole:
Step 1: 2-(ethoxymethylene)malononitrile The preparation 2-(ethoxymethylene)malononitrile was carried out in a manner similar to that described in Step 1 of Example 2.
Step 2: 5-amino-l -methyl-lH-pyrazole-4-carbonitriie
The 5-amino- l-methyl-lH-pyrazole-4-carbonitrile was synthesized according to the above method described in Step 2 of Example 2.
Step 3: 5-bromo-l -methyl-lH-pyrazole-4-carbonitrile
A mixture of 5-amino-l -methyl-lH-pyrazole-4-carbonitrile (20 gm, 1.63 moles) obtained from Step 2, hydrobromic acid (280 ml, strength: 48%) in DM water (605 ml) was stirred at room at 0 to 5°C and sodium nitrite solution (by dissolving sodium nitrite (16.94 gm, 0.245 moles) in Dl water (242 ml)) was slowly added. Solid cuprous bromide (37.22 gm, 0.260 moles) was added to the above reaction mixture, stirred the reaction mixture for 3-4 hours at 0 to 5°C. Then the reaction temperature was raised to room temperature and stirred for 15- 18 hour. To the above reaction mixture, cold DI water ( 1000 ml) was added at 0-5°C and stirred the resulting suspension for 1 -2 hours. Progress of the reaction was monitored by HPLC. The solid product was filtered, washed with cold DI water (200 ml) and dried at 60- 65°C the product, 5-bromo-l -methyl-lH-pyrazole-4-carbonitrile was obtained.
Dry wt : 2 1 .2 gm
Yield : 1 .06 w/w (69%)
HPLC purity : 99.58%
MP : 90-93°C
Step 4: 5-(5-bromo-l-methyl-lH-pyrazol-4-yl)-2H-tetrazole (Compound 31)
5-(5-bromo-l -methyl- lH-pyrazol-4-yl)-2H-tetrazole was obtained from 5-bromo-l -methyl- lH-pyrazole-4-carbonitrile, obtained in step 3 by the process as in example 3.
Compounds 32-60 were prepared by following the experimental procedure of Example 3 and/or 4 using appropriate intermediates.
Figure imgf000102_0001
· Br H 3 CI C6H4 5-[5-bromo- l -(3-chlorophenyl)- lH-pyrazol- 4-yl]-2H-tetrazole
Br H 4 CI C6H4 5-[5-bromo- 1 -(4-chloropheny 1)- lH-pyrazol- 4-yl]-2H-tetrazole
Br H 2,3 Cl2 C6H3 5-[5-bromo- 1 -(2,3-dichlorophenyl)- 1 H- pyrazol-4-yl]-2H-tetrazole
Br H 2,4 C12 C6H3 5-[5-bromo-l -(2,4-dichlorophenyl)-lH- pyrazol-4-yl]-2H-tetrazole
Br H 2,5 Cl2 C6H3 5-[5-bromo-l -(2,5-dichlorophenyl)-lH- pyrazol-4-yl]-2H-tetrazole
Br H 2,6 Cl2 C6H3 5-[5-bromo- 1 -(2,6-dichlorophenyl)- 1H- pyrazol-4-yl]-2H-tetrazole
Br H 3,4 Cl2 C6H3 5-[5-bromo-l -(3,4-dichlorophenyl)- lH- pyrazol-4-yl]-2H-tetrazole
Br H 3,5 C12 C6H3 5-[5-bromo-l -(3,5-dichlorophenyl)- lH- py razo 1-4-y l]-2H-tetrazo le
Br H 2 Br C6H4 5-[5-bromo- 1 -(2-bromopheny 1)- 1 H-pyrazol- 4-yl]-2H-tetrazole
Br H 3 Br C6H4 5-[5-bromo- 1 -(3-bromopheny 1)- 1 H-pyrazol- 4-yl]-2H-tetrazole
Br H 4 Br C6H4 5-[5-bromo- 1 -(4-bromopheny 1)- 1 H-pyrazol- 4-yl]-2H-tetrazole
Br H 4 F C6H4 5-[5 -bromo- 1 -(4-fluoropheny 1)- 1 H-pyrazol- 4-yl]-2H-tetrazole
Br H 2 F C6¾ 5-[5-bromo-l -(2-fluorophenyl)-lH-pyrazol- 4-yl]-2H-tetrazole
Br H 2,3 5-[5-bromo- l -(2,3-dimethylphenyl)- lH-
(CH3)2C6H3 pyrazol-4-yl]-2H-tetrazole
Br H 2,4 5-[5-bromo- 1 -(2,4-dimethy lpheny 1)- 1 H-
(CH3)2C6H3 pyrazol-4-yl]-2H-tetrazole
Br H 2,5 5-[5-bromo-l -(2,5-dimethyIphenyl)-lH-
(CH3)2 6H3 pyrazol-4-yl]-2H-tetrazole
Br H 2,6 5-[5-bromo- l -(2,6-dimethylphenyl)-lH-
(CH3)2C6H3 pyrazol-4-yl]-2H-tetrazole
Br H 3,4 5-[5-bromo- 1 -(3,4-dimethy lpheny 1)- 1 H-
(CH3)2C6H3 pyrazol-4-yl]-2H-tetrazole
Br H 3,5 5-[5-bromo- l -(3,5-dimethylphenyl)-lH-
(CH3)2CeH3 pyrazol-4-yl]-2H-tetrazole
Br H 2 5-[5-bromo- 1 -(2-ethy lpheny 1)- 1 H-pyrazol-4-
CH2CH3C6H4 yl]-2H-tetrazole 57 Br H 4 5-[5-bromo- l -(4-ethylphenyl)- lH-pyrazol-4-
C H2CH3C6H4 yl]-2H-tetrazole
58 Br H 4 OCH3C6H4 5-[5-bromo- 1 -(4-methoxyphenyl)- 1 H- py razo 1-4-y 1] -2H-tetrazo le
59 Br H 2 CH3C6H4 5-[5-bromo-l -(2-methylphenyl)- lH-pyrazol- 4-yl]-2H-tetrazole
60 Br 4 CH3C6H4 5-[5-bromo- l -(4-methylphenyl)-lH-pyrazol- 4-yl]-2H-tetrazole
Example 5: 5-(5-chloro-l-methyl-lH-pyrazol-4-yl)-2-methyl-2H-tetrazole (Compound 61):
5-(5-chloro-l-methyl- lH-pyrazole-4-yl)-2H-tetrazole ( 10.0 gm, 0.0541 moles) obtained in Example 1, or 2, was dissolved in acetone (50.0 ml). Potassium carbonate (6.0 gm, 0.0433 moles) was added and stirred for about 1 hour at 20-30°C. To this mixture, slowly added a solution of DMS (9.5 gm, 0.0757 moles) in acetone (10.0 ml) maintaining the temperature below 30°C. The reaction mixture was stirred at room temperature for about 1 hour and monitored the progress of the reaction by HPLC. The inorganic solids were filtered off. Acetone was distilled off from the filtrate to obtain the crude product containing 5-(5- chloro-l -methyl- lH-pyrazole-4-yl)-2-methyl-2H-tetrazole), its regio-isomer, 5-(5-chloro- l - methyl-lH-pyrazole-4-yl)-l -methyl-2H-tetrazole), or mixture thereof. The desired regio- isomer, 5-(5-chloro-l -methyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole), was isolated by column chromatography.
Dry wt : 7.81 gm
Yield : 0.78 w/w (73%)
HPLC purity : 99.12 %
MP : 125-127°C
Compounds 62- 330 were prepared by following the experimental procedure of Example 5 using appropriate intermediates.
Figure imgf000104_0001
methyl-2H-tetrazole
66 CI CH3 2 C1C6H4 5-[5-chloro-l -(2-chlorophenyl)-l H-pyrazol-4- yl]-2-methyl-2H-tetrazole
67 CI CH3 3 CI C6H4 5-[5-chloro- l -(3-chlorophenyl)-lH-pyrazol-4- yl]-2-methyl-2H-tetrazole
68 CI CH3 4 CI C6H4 5-[5-chloro- l -(4-chlorophenyl)- lH-pyrazol-4- yl]-2-methyl-2H-tetrazole
69 CI CH3 2,3C12C6H3 5-[5-chloro-l -(2,3-dichlorophenyl)-lH- pyrazol-4-yl]-2-methyl-2H-tetrazole
70 CI CH3 2,4C12C6H3 5-[5-chloro- 1 -(2,4-dichlorophenyl)- 1H- pyrazol-4-yl]-2-methyl-2H-tetrazole
71 CI CH3 2,5C12C6H3 5-[5-chloro- l -(2,5-dichlorophenyl)-lH- pyrazol-4-yl]-2-methyl-2H-tetrazole
72 CI CH3 2,6C12C6H3 5-[5-chloro- 1 -(2,6-dichlorophenyl)- l H- pyrazol-4-yl]-2-methyl-2H-tetrazole
73 CI CH3 3,4C12C6H3 5-[5-ch!oro- 1 -(3,4-dichlorophenyl)- 1H- pyrazol-4-y.l]-2-methyl-2H-tetrazole
74 CI CH3 3,5Cl CgH3 5-[5-chloro-l -(3,5-dichlorophenyl)- lH- pyrazol-4-yl]-2-methyt-2H-tetrazole
75 CI CH3 2 Br C6H4 5-[l -(2-bromopheny l)-5-chloro- l H-pyrazol-4- yl]-2-methyl-2H-tetrazole
76 CI CH3 3 Br C6H4 5-[l -(3-bromophenyl)-5-chloro- lH-pyrazol-4- yl]-2-methyl-2H-tetrazole
77 CI CH3 4 Br C6H4 5-[l -(4-bromophenyl)-5-chloro- lH-pyrazol-4- yl]-2-methyl-2H-tetrazole
78 CI CH3 4 F C6H4 5-[5-chloro- 1 -(4-fluorophenyl)- 1 H-pyrazol-4- yl]-2-methyl-2H-tetrazole
79 CI CH3 2 F C¾H4 5-[5-chloro- l -(2-fluorophenyl)-lH-pyrazol-4- yl]-2-methyl-2H-tetrazole
80 CI CH3 2,3(CH3)2C 5-[5-chloro- 1 -(2,3-dimethy lpheny 1)- 1 H- pyrazol-4-yl]-2-methyl-2H-tetrazole
81 CI CH3 2,4(CH3)2 5-[5-chloro- 1 -(2,4-dimethy lpheny 1)- 1 H- C6H3 pyrazol-4-yl]-2-methyl-2H-tetrazole
82 CI CH3 2,5(CH3)2 5-[5-chloro- l -(2,5-dimethylphenyl)- lH- C6H3 pyrazol-4-yl]-2-methyl-2H-tetrazole
83 CI CH3 2,6(CH3)2 5-[5-chloro- 1 -(2, 6-dimethy lpheny 1)- 1 H- C6H3 pyrazol-4-yl]-2-methyl-2H-tetrazole
84 CI CH 3,4(CH3)2 5-[5-chloro- 1 -(3,4-dimethy lphenyl)- 1 H- C6H3 pyrazol-4-yl]-2-methyl-2H-tetrazole
85 CI CH3 3,5(CH3)2 5-[5-chloro- 1 -(3, 5-dimethy lpheny 1)- 1 H- C6H3 pyrazol-4-yl]-2-methyl-2H-tetrazole 86 CI CH3 2CH2CH3C 5-[5-chloro- 1 -(2-ethy Iphenyl)- 1 H-pyrazol-4- 6H4 yI]-2-methyl-2H-tetrazole
87 CI CH3 4CH2CH3C 5-[5-chloro- l-(4-ethylphenyl)-lH-pyrazol-4- 6H4 yl]-2-methyl-2H-tetrazole
88 CI CH3 4 5-[5-chloro- l -(4-methoxyphenyl)- lH-pyrazol-
OCH3C6H4 4-yl]-2-methyl-2H-tetrazole
89 CI CH3 2CH3C6H4 5-[5-chloro- l -(2-methylphenyl)- lH-pyrazol-4- yl]-2-methyl-2H-tetrazole
90 CI CH3 4 CH3C6H4 5-[5-chloro- 1 -(4-methy Iphenyl)- 1 H-pyrazol-4- yl]-2-methyl-2H-tetrazole
91 CI CH2CH3 CH3 5-(5-chloro- l -methyl- lH-pyrazol-4-y l)-2- ethyl-2H-tetrazole
92 CI CH2CH3 CH2CH3 5-(5-chloro- 1 -ethyl- 1 H-pyrazol-4-y l)-2-ethy I- 2H-tetrazole
93 CI CH2CH3 (CH3)2CH 5-[5-chloro- 1 -(2-methy Ipropyl)- 1 H-pyrazol-4- CH2 yl]-2-ethyl-2H-tetrazole
94 CI CH2CH3 CH2Ph 5-(l -benzyl-5-chloro-lH-pyrazol-4-yl)-2- ethyl-2H-tetrazole
95 CI CH2CH3 C6H5 5-(5-chloro- 1 -phenyl- 1 H-pyrazol-4-yl)-2- ethyl-2H-tetrazole
96 CI CH2CH3 2 C1C6H4 5-[5-chloro- l -(2-chlorophenyl)- lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
97 CI CH2CH3 3 CI C6H4 5-[5-chloro- l -(3-chlorophenyl)- lH-pyrazol-4- y 1] -2 -ethy l-2H-tet razo le
98 CI CH2CH3 4 CI C6H4 5-[5-chloro-l -(4-chlorophenyl)- lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
99 CI CH2CH3 2,3 Cl2 5-[5-chloro-l -(2,3-dichlorophenyl)-l H-
CeHj, pyrazol-4-yl]-2-ethyl-2H-tetrazole
100 CI CH2CH3 2,4 Cl2 5-[5-chloro-l -(2,4-dichlorophenyl)- 1 H- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
101 CI CH2CH3 2,5 Cl2 5-[5-chloro- l -(2,5-dichlorophenyl)- l H- C6H3 py razo 1-4-y l]-2-ethy l-2H-tetrazo le
102 CI CH2CH3 2,6 Cl2 5-[5-chloro-l -(2,6-dichlorophenyl)-lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
103 CI CH2CH3 3,4 Cl2 5-[5-chloro-l -(3,4-dichlorophenyl)-lH- CgH3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
104 CI CH2CH3 3,5 Cl2 5-[5-chloro- l -(3,5-dichlorophenyl)- lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetr'azole 105 CI CH2CH3 2 Br C6H4 5-[l-(2-bromophenyl)-5-chlon lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
106 CI CH2CH3 3 BrC6H4 5-[l-(3-bromophenyl)-5-chloro-lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
107 CI CH2CH3 4 Br C6H4 5-[l-(4-bromophenyl)-5-chloro-lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
108 CI CH2CH3 4 F C6H4 5-[5-chloro- 1 -(4-fluoropheny 1)- 1 H-pyrazol-4- yl]-2-ethyl-2H-tetrazole
109 CI CH2CH3 2 F C6H4 5-[5-chloro-l-(2-fluorophenyl)-lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
110 CI CH2CH3 2,3(CH3)2 5-[5-chloro-l-(2,3-dimethylphenyl)-lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
111 CI CH2CH3 2,4(CH3)2 5-[5-chlor0-l-(2,4-dimethylphenyl)-lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
112 CI CH2CH3 2,5(CH3)2 5-[5-chloro-l-(2,5-dimethylphenyl)-lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
113 CI CH2CH3 2,6(CH3)2 5-[5-chloro-l-(2,6-dimethylphenyl)-lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
114 CI CH2CH3 3,4(CH3)2 5-[5-chloro-l-(3,4-dimethylphenyl)-lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
115 CI CH2CH3 3,5(CH3)2 5-[5-chloro-l-(3,5-dimethylphenyl)-lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
116 CI CH2CH3 2CH2CH3C 5-[5-chloro-l-(2-ethylphenyl)-lH-pyrazol-4- βΗ4 yl]-2-ethyl-2H-tetrazole
117 ci CH2CH3 4CH2CH3C 5-[5-chloro- 1 -(4-ethylphenyl)- 1 H-pyrazol-4- yl]-2-ethyl-2H-tetrazole
118 CI CH2CH3 4 5-[5-chloro-l-(4-methoxyphenyl)-lH-pyrazol-
OCH3C6H4 4-yl]-2-ethyl-2H-tetrazole
119 CI CH2CH3 2CH3CfiH4 5-[5-chloro- 1 -(2-methylphenyl)- 1 H-pyrazol-4- yl]-2-ethyl-2H-tetrazole
120 CI CH2CH3 4CH3C6H4 5-[5-chloro-l-(4-methylphenyl)-lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
121 CI CH(CH3)2 CH3 5-(5-chloro- 1 -methyl- 1 H-pyrazol-4-yl)-2-( 1- methylethyl)-2H-tetrazole
122 CI CH(CH3)2 CH2CH3 5-(5-chloro- 1 -ethyl- 1 H-pyrazol-4-y l)-2-( 1 - methylethyl)-2H-tetrazole
123 CI CH(CH3)2 (CH3)2CH 5-[5-chloro-l-(2-methylpropyl)-lH-pyrazol-4- CH2 y l]-2-( 1 -methy lethy l)-2H-tetrazole 267 CI 4CH30 4CH2CH3 5-[5-chloro- l -(4-ethylphenyl)- lH-pyrazol-4- C6H4CH2 C6H4 yl]-2-(4-methoxybenzyl)-2H-tetrazole
268 CI 4CH30 4 5-[5-chloro- l -(4-methoxypheny])- l H-pyrazol-
C6H4CH2 0CH3C6H4 4-yl]-2-(4-methoxybenzyl)-2H-tetrazole
269 CI 4CH30 2 CH3CgH4 5-[5-chloro- 1 -(2-methylphenyl)- 1 H-pyrazol-4- C6H4CH2 yI]-2-(4-methoxybenzyI)-2H-tetrazole
270 CI 4CH30 4 CH3C6H4 5-[5-chloro-l -(4-methylphenyl)- l H-pyrazol-4- C6H4CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
271 CI 3CH3C6H4 CH3 5-(5-chloro- l -methyl- 1 H-pyrazol-4-yl)-2-(3- CH2 methylbenzyl)-2H-tetrazole
272 CI 3CH3C6H4 CH2CH3 5-(5-chloro- 1 -ethyl- l H-pyrazol-4-y l)-2-(3- CH2 methylbenzyl)-2H-tetrazole
273 . CI 3CH3C6H4 (CH3)2CH 5-[5-chloro-l -(2-methylpropyl)- l H-pyrazol-4- CH2 CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
274 CI 3CH3C6H4 CH2Ph 5-( l -benzyl-5-chloro- l H-pyrazol-4-yl)-2-(3- CH2 methylbenzyl)-2H-tetrazole
275 CI 3CH3C6H4 C6H5 5-(5-chloro-l -phenyl- 1 H-pyrazol-4-y l)-2-(3- CH2 methylbenzyl)-2H-tetrazole
276 CI 3CH3C6H4 2 CIC6H4 5-[5-chloro- l -(2-chlorophenyl)- l H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
111 CI 3CH3C6H4 3 CI C6H4 5-[5-chloro- 1 -(3-chloropheny 1)- 1 H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
278 CI 3CH3CgH4 4 CI C6H4 5-[5-chloro- l -(4-chlorophenyl)-lH-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
279 CI 3CH3C6H4 2,3 Cl2 5-[5-chloro- 1 -(2,3-dichlorophenyl)- 1H- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
280 CI 3CH3C6H4 2,4 Cl2 5-[5-chloro- l -(2,4-dichlorophenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
281 CI 3CH3C6H4 2,5 Cl2 5-[5-chloro- 1 -(2,5-dichlorophenyl)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
282 CI 3CH3CgH4 2,6 Cl2 5-[5-chloro-l -(2,6-dichlorophenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
283 CI . 3CH3C6H4 3,4 Cl2 5-[5-chloro-l-(3,4-dichlorophenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
284 Ci 3CH3C6H4 3,5 Cl2 5-[5-chloro- 1 -(3,5-dichlorophenyl)- 1 H- CH2 C&H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
285 CI 3CH3C6H4 2 Br C6H4 5-[ 1 -(2-bromophenyl)-5-chloro- 1 H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
114 286 CI 3CH3C6H4 3 Br C6H4 5-[l -(3-bromophenyl)-5-chloro- lH-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
287 CI 3CH3C6H4 4 Br C6H4 5-[l -(4-bromophenyl)-5-chloro- lH-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
288 CI 3CH3C6H4 4 F C6H4 5-[5-chloro- l -(4-fluorophenyI)- lH-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
289 CI 3CH3C6H4 2 F CgH4 5-[5-chloro- 1 -(2-fluorophenyl)- 1 H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
290 CI 3CH3C6H4 2,3(CH3)2 5-[5-chloro-l -(2,3-dimethylphenyl)-l H- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
291 CI 3CH3C6H4 2,4(CH3)2 5-[5-chloro- l -(2,4-dimethylphenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
292 CI 3CH3CgH4 2,5(CH3)2 5-[5-chloro- 1 -(2,5-dimethylpheny 1)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
293 CI 3CH3C6H4 2,6(CH3)2 5-[5-chloro-l -(2,6-dimethylphenyl)- l H- CH2 C6H3 pyrazoI-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
294 CI 3CH3C6H4 3,4(CH3)2 5-[5-chloro-l -(3,4-dimethylphenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
295 CI 3CH3C6H4 3,5(CH3)2 5-[5-chloro-l -(3,5-dimethylphenyl)- l H- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
296 CI 3CH3C6H4 2CH2CH3 5-[5-chloro- l -(2-ethylphenyl)-lH-pyrazol-4- CH2 C6H4 yl]-2-(3-methylbenzyl)-2H-tetrazole
297 CI 3CH3C6H4 4 CH2CH3 5-[5-chloro- l -(4-ethylphenyl)- ] H-pyrazol-4- CH2 C6H4 yl]-2-(3-methylbenzyl)-2H-tetrazole
298 CI 3CH3C6H4 4 5-[5-chloro-l -(4-methoxyphenyl)- lH-pyrazol- CH2 OCH3CeH4 4-yl]-2-(3-methylbenzyl)-2H-tetrazole
299 CI 3CH3C6H4 2 CH3C6H4 5-[5-chtoro-l -(2-methylphenyl)-l H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
300 CI 3CH3C6H4 4CH3C6H4 5-[5-chloro- 1 -(4-methylphenyl)- 1 H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
301 CI 4N02C6H4 CH3 5-(5-chloro- 1 -methyl- 1 H-pyrazol-4-y l)-2-(4- CH2 nitrobenzyl)-2H-tetrazole
302 CI 4N02C6H4 CH2CH3 5-(5-chloro- 1 -ethyl- 1 H-pyrazol-4-y l)-2-(4- CH2 nitrobenzyl)-2H-tetrazole
303 CI 4N02C6H4 (CH3)2CH 5-[5-chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4- CH2 CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
115 304 CI 4N02C6H4 CH2Ph 5-( l -benzyl-5-chloro- lH-pyrazol-4-yl)-2-(4- CH2 nitrobenzyl)-2H-tetrazole
305 CI 4N02C6H4 C6H5 , 5-(5-chloro-l -phenyl- lH-pyrazol-4-yl)-2-(4- CH2 nitrobenzyl)-2H-tetrazole
306 CI 4N02C6H4 2 CIC6H4 5-[5-chloro- 1 -(2-chlorophenyl)- 1 H-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
307 CI 4N02C6H4 3 CI C6H4 5-[5-chloro- 1 -(3-chloropheny 1)- 1 H-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
308 CI 4N02C6H4 4 CI C6H4 5-[5-chloro- 1 -(4-chloropheny 1)- 1 H-pyrazol-4- CH2 y l]-2-(4-n itrobenzy I)-2H-tetrazole
309 CI 4N02C6H4 2,3 Cl2 5-[5-chloro-l -(2,3-dichlorophenyl)-l H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
310 CI 4N02C6H4 2,4 Cl2 5-[5-chloro- l -(2,4-dichlorophenyl)- lH- CH2 C¾H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
31 1 CI 4N02C6H4 2,5 Cl2 5-[5-chloro- l -(2,5-dichlorophenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
312 CI 4N02C6H4 2,6 Cl2 5-[5-chloro- l -(2,6-dichlorophenyl)- lH- CH2 C6H pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
313 CI 4N02C6H4 3,4 Cl2 5-[5-chloro- 1 -(3,4-dichloropheny 1)- 1 H- CH C6H3 pyrazol-4-yl]-2-(4-nitro*benzyl)-2H-tetrazole
3 14 CI 4N02C6H4 3,5 Cl2 5-[5-chloro- l -(3,5-dichlorophenyl)-l H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
3 15 CI 4N02C6H4 2 Br C6H4 5-[ 1 -(2-bromopheny l)-5-ch!oro- 1 H-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
316 CI 4N02C6H4 3 Br C6H4 5-[l -(3-bromophenyl)-5-chloro- lH-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
317 CI 4N02C6H4 4 Br C6H4 5-[l -(4-bromophenyl)-5-chloro-lH-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
31 8 CI 4N02C6H4 4 F C6H4 5-[5-chloro-l -(4-fluorophenyl)-lH-pyrazol-4- CH2 y 1] -2-(4-n itrobenzy l)-2H-tetrazo le
3 19 CI 4N02C6H4 2 F CgH4 5-[5-chloro- 1 -(2-fl uorophenyl)- 1 H-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
320 CI 4N02C6H4 2,3(CH3)2 5-[5-chloro-l -(2,3-dimethylphenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
321 CI 4N02C6H4 2,4(CH3)2 5-[5-chloro-l -(2,4-dimethylphenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
322 CI 4N02C6H4 2,5(CH3)2 5-[5-chloro- 1 -(2,5-dimethylphenyl)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
116 323 CI 4N02C6H4 2,6(CH3)2 5-[5-chloro- l -(2,6-dimethylphenyl)- lH- CH2 C6H3 pyrazol-4-y]]-2-(4-nitrobenzyl)-2H-tetrazoIe
324 CI 4N02C6H4 3,4(CH3)2 5-[5-chloro- 1 -(3,4-dimethylphenyl)- 1H- CH2 CeH3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
325 CI 4N02C6H4 . 3,5(CH3)2 5-[5-chloro- 1 -(3,5-dimethylphenyl)- IH- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
326 CI 4N02C6H4 2CH2CH3 5-[5-chloro- l -(2-ethylphenyl)-lH-pyrazol-4- CH2 C6H4 yl]-2-(4-nitrobenzyl)-2H-tetrazole
327 CI 4N02C6H4 4CH2CH3 5-[5-chloro- l -(4-ethylphenyl)- l H-pyrazol-4- CH2 C6H4 yl]-2-(4-nitrobenzyl)-2H-tetrazole
328 CI 4N02C6H4 4 5-[5-chIoro- l -(4-methoxyphenyl)- lH-pyrazol- CH2 OCH3CgH4 4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
329 CI 4N02C6H4 2 CH3C6H4 5-[5-chloro- l -(2-methylphenyl)-lH-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
330 CI 4N02C6H4 4 CH3C6H4 5-[5-chloro- l -(4-methylphenyl)- lH-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
Example 6: 5-(5-bromo-l-methyI-lH-pyrazol-4-yl)-2-methyl-2H-tetrazole (Compound 331):
Dissolve 5-(5-bromo-l -methyl- lH-pyrazol-4-yl)-2H-tetrazoIe (9.5 gm, 0.0414 moles) obtained from Example 3 or 4, in acetonitrile (100 ml). Potassium hydroxide (5.71 gm, 0. 10 moles) and methyl iodide (24.5 gm, 0.171 moles) were added and stirred at 20-30°C for 20- 25 hour. The progress of the reaction was monitored by HPLC. The acetonitrile was recovered at 55-60°C at reduced pressure. To the above residue, dichloromethane ( 100 ml) and DI water (100 ml) were added and stirred the above reaction mixture for 10- 1 5 min at 20-25°C. The reaction mixture was allowed to settle. The organic layer was separated and aqueous layer was extracted with DCM. The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (50 ml). Stirred for 10-15 min and separated the final aqueous layer and organic layer. The organic layer was evaporated to obtain the crude product, 5-(5-chloro-l -methyl- l H-pyrazole-4-yl)-2-methyl-2H-tetrazole), or 5-(5-chloro- l -methyl- l H-pyrazole-4-yl)- l -methyl-2H-tetrazole), mixture thereof. The desired regio-isomer, 5-(5-chloro-l -methyl-lH-pyrazol-4-yl)-2-methyl-2H-tetrazole), was isolated by column chromatography.
Dry wt : 5 gm
Yield : 0.53 w/w (50%)
HPLC purity : 99.95%
117 Compounds 332-600 were prepared by following the experimental procedure of Example 6 appropriate intermediates.
Figure imgf000112_0001
118 C6H3 pyrazol-4-yl]-2-methyl-2H-tetrazole
354 Br CH3 3,4(CH3)2 5-[5-bromo- l -(3,4-dimethylphenyl)- l H- C6H3 pyrazol-4-yl]-2-methyl-2H-tetrazole
355 Br CH3 3,5(CH3)2 5-[5-bromo- l -(3,5-dimethyIphenyl)-lH- CeH3 pyrazol-4-yl]-2-methyl-2H-tetrazole
356 Br CH3 2CH2CH3 5-[5-brdmo- 1 -(2-ethy Ipheny 1)- 1 H-pyrazol-4- CgH4 yl]-2-methyl-2H-tetrazole
357 Br CH3 4CH2CH3 5-[5-bromo- 1 -(4-ethy Ipheny 1)- 1 H-pyrazol-4- C&H yl]-2-methyl-2H-tetrazole
358 Br CH3 4 5-[5-bromo-l -(4-methoxyphenyl)-lH-pyrazol-
OCH3C6H4 4-yl]-2-methyl-2H-tetrazole
359 Br CH3 2CH3CgH4 5-[5-bromo-l -(2-methy]phenyl)-lH-pyrazol-4- yl]-2-methyl-2H-tetrazole
360 Br CH3 4CH3C6H4 5-[5-bromo- 1 -(4-methy Ipheny 1)- 1 H-pyrazol-4- yl]-2-methyl-2H-tetrazole
361 Br CH2CH3 CH3 5-(5-bromo- 1 -methyl- 1 H-pyrazoI-4-y l)-2- ethyl-2H-tetrazole
362 Br CH2CH3 CH2CH3 5-(5-bromo-l -ethyl- lH-pyrazol-4-y l)-2-ethyl- 2H-tetrazole
363 Br CH2CH3 (CH3)2CH 5-[5-bromo- l -(2-methylpropyl)-lH-pyrazol-4- CH2 y]]-2-ethyl-2H-tetrazole
364 Br CH2CH3 CH2Ph 5-(l-benzyl-5-bromo- l H-pyrazol-4-yl)-2- ethyl-2H-tetrazole
365 Br CH2CH3 C6H5 5-(5-bromo- 1 -phenyl- 1 H-pyrazol-4-y l)-2- ethyl-2H-tetrazole
366 Br CH2CH3 2 C1C6H4 5-[5-bromo- 1 -(2-chloropheny 1)- 1 H-pyrazol-4- yl]-2-ethyl-2H-tetrazole
367 Br CH2CH3 3 CI C6H4 5-[5-bromo- l -(3-chlorophenyl)- l H-pyrazol-4- yl]-2-ethyl-2H-tetrazole
368 Br CH2CH3 4 CI C6H4 5-[5-bromo- l -(4-chlorophenyl)-lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
369 Br CH2CH3 2,3 CI2 5-[5-bromo- l-(2,3-dichlorophenyl)- lH- C6H3 pyrazol-4-yI]-2-ethyl-2H-tetrazole
370 Br CH2CH3 2,4 CI2 5-[5-bromo- l-(2,4-dichlorophenyl)- lH- CeH3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
371 Br CH2CH3 2,5 Cl2 5-[5-bromo- l -(2,5-dichlorophenyl)- lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
372 Br CH2CH3 2,6 Cl2 5-[5-bromo- 1 -(2,6-dichlorophenyl)- 1 H-
C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
373 Br CH2CH3 3,4 Cl2 5-[5-bromo-l -(3,4-dichlorophenyl)- lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
374 Br CH2CH3 3,5 Cl2 5-[5-bromo- l -(3,5-dichlorophenyl)-lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
375 Br CH2CH3 2 Br C¾H4 5-[5-bromo- 1 -(2-bromophenyl)- 1 H-pyrazol-4- yl]-2-ethyl-2H-tetrazole
376 Br CH2CH3 3 Br CgH4 5-[5-bromo- l -(3-bromophenyl)- lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
377 Br CH2CH3 4 Br C6H4 5-[5-bromo- 1 -(4-bromophenyl)- 1 H-pyrazol-4- yl]-2-ethyl-2H-tetrazole
119 378 Br CH2CH3 4 F C6H4 5-[5-bromo- l -(4-fluorophenyl)- lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
379 Br CH2CH3 2 F C6H4 5-[5-bromo- l-(2-fIuorophenyl)-lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
380 Br CH2CH3 2,3(CH3)2 5-[5-bromo- 1 -(2,3-dimethy lphenyl)- 1H- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
381 Br CH2CH3 2,4(CH3)2 5-[5-bromo-l -(2,4-dimethylphenyl)- lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
382 Br CH2CH3 2,5(CH3)2 5-[5-bromo- 1 -(2, 5-dimethy lphenyl)- 1 H- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
383 Br CH2CH3 2,6(CH3)2 5-[5-bromo-l -(2,6-dimethylphenyl)- lH- C6H3 py razo 1-4-y l]-2-ethy l-2H-tetrazole
384 Br CH2CH3 3,4(CH3)2 5-[5-bromo-l -(3,4-dimethylphenyl)-lH- C6H3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
385 Br CH2CH3 3,5(CH3)2 5-[5-bromo- 1 -(3,5-dimethylpheny 1)- 1 H- CfiH3 pyrazol-4-yl]-2-ethyl-2H-tetrazole
386 Br CH2CH3 2CH2CH3 5-[5-bromo-l -(2-ethylphenyl)- l H-pyrazol-4- C6H4 yl]-2-ethyl-2H-tetrazole
387 Br CH2CH3 4CH2CH3 5-[5-bromo-l -(4-ethylphenyl)- l H-pyrazol-4- C6H4 yl]-2-ethyl-2H-tetrazole
388 Br CH2CH3 4 5-[5-bromo-l-(4-methoxyphenyl)-l H-pyrazol-
OCH3C6H4 4-yl]-2-ethyl-2H-tetrazole
389 Br CH2CH3 2 CH3C6H4 5-[5-bromo- 1 -(2-methylpheny 1)- 1 H-pyrazol-4- yl]-2-ethyl-2H-tetrazole
390 Br CH2CH3 4 CH3C6H4 5-[5-bromo-l -(4-methylphenyl)-lH-pyrazol-4- yl]-2-ethyl-2H-tetrazole
391 Br CH(CH3)2 CH3 5-(5-bromo- -methyl- l H-pyrazol-4-y l)-2-( l - methylethyl)-2H-tetrazole
392 Br CH(CH3)2 CH2CH3 5-(5-bromo- 1 -ethyl- 1 H-pyrazol-4-y l)-2-( 1 - methylethyl)-2H-tetrazole
393 Br CH(CH3)2 (CH3)2CH 5-[5-bromo- l -(2-methy.lpropyl)- lH-pyrazol-4- CH2 y l]-2-( 1 -methylethyl)-2H-tetrazole
394 Br CH(CH3)2 CH2Ph 5-(l -benzyl-5-bromo- 1 H-pyrazol-4-y l)-2-( 1 - methylethyl)-2H-tetrazole
395 Br CH(CH3)2 C6H5 5-(5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)-2-( 1 - methylethyl)-2H-tetrazole
396 Br CH(CH3)2 2 C1C6H4 5-[5-bromo- l -(2-chlorophenyl)- l H-pyrazol-4- yl]-2-( 1 -methy lethy l)-2H-tetrazole
397 Br CH(CH3)2 3 CI C6H4 5-[5-bromo- l -(3-chlorophenyl)-lH-pyrazol-4- yl]-2-( 1 -methylethyl)-2H-tetrazole
398 Br CH(CH3)2 4 CI C6H4 5-[5-bromo- 1 -(4-chloropheny 1)- 1 H-pyrazol-4- y l]-2-( 1 -methy lethy l)-2H-tetrazole
399 Br CH(CH3)2 2,3 Cl2 5-[5-bromo- l -(2,3-dichlorophenyl)-lH- C6H3 pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole
400 Br CH(CH3)2 2,4 Cl2 5-[5-bromo- 1 -(2,4-dichlorophenyl)- 1 H- C6H3 pyrazol-4-yl]-2-( 1 -methylethy l)-2H-tetrazole
401 Br CH(CH3)2 2,5 Cl2 5-[5-bromo- 1 -(2,5-dichIoropheny 1)- 1 H- C6H3 pyrazol-4-y l]-2-( 1 -methylethyl)-2H-tetrazole
402 Br CH(CH3)2 2,6 Cl2 5-[5-bromo- 1 -(2,6-dichlorophenyl)- 1 H-
120 C6H3 pyrazol-4-y l]-2-( 1 -methy lethyl)-2H-tetrazole
403 Br CH(CH3)2 3,4 Cl2 5-[5-bromo-l -(3,4-dichlorophenyl)- lH- ΟόΗ3 pyrazol-4-y l]-2-( 1 -methylethy l)-2H-tetrazole
404 Br CH(CH3)2 3,5 Cl2 5-[5-bromo- l -(3,5-dichlorophenyl)-lH- C6H3 pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole
405 Br CH(CH3)2 2 Br C¾H4 5-[5-bromo- 1 -(2-bromophenyl)- lH-pyrazol-4- y l]-2-( 1 -methylethyl)-2H-tetrazole
406 Br CH(CH3)2 3 Br C¾H4 5-[5-bromo-l -(3-bromophenyl)- lH-pyrazol-4- y l]-2-( 1 -methy lethyl)-2H-tetrazole
407 Br CH(CH3)2 4 Br C6H4 5-[5-bromo-l -(4-bromophenyl)- lH-pyrazol-4- yl]-2-( 1 -methylethy l)-2H-tetrazole
408 Br CH(CH3)2 4 F C6H4 5-[5-bromo- l -(4-fluorophenyl)- lH-pyrazol-4- yl]-2-( 1 -methylethy l)-2H-tetrazole
409 Br CH(CH3)2 2 F C6H4 5-[5.-bromo- l -(2-fluorophenyl)- lH-pyrazol-4- yl]-2-(l -methylethy l)-2H-tetrazole
410 Br CH(CH3)2 2,3(CH3)2 5-[5-bromo- 1 -(2, 3-dimethy Iphenyl)- 1 H- 0¾Η3 pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole
41 1 Br CH(CH3)2 2,4(CH3)2 5-[5-bromo- 1 -(2,4-dimethylpheny 1)- 1 H- CeH3 pyrazol-4-yI]-2-(l -methy lethyl)-2H-tetrazole
412 Br CH(CH3)2 2,5(CH3)2 5-[5-bromo- l -(2,5-dimethylphenyl)- l H- C6H3 pyrazol-4-y l]-2-( 1 -methy lethy l)-2H-tetrazole
413 Br CH(CH3)2 2,6(CH3)2 5-[5-bromo- 1 -(2,6-dimethylphenyl)- 1 H- C6H3 pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole
414 Br CH(CH3)2 3,4(CH3)2 5-[5-bromo-l -(3,4-dimethylphenyl)- lH- C6H3 pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole
415 Br CH(CH3)2 3,5(CH3)2 5-[5-bromo-l -(3,5-dimethylphenyl)- IH- C6H3 pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole
416 Br CH(CH3)2 2CH2CH3 5-[5-bromo- 1 -(2-ethylphenyl)- 1 H-pyrazol-4- C6H4 yl]-2-( 1 -methylethyl)-2H-tetrazole
417 Br CH(CH3)2 4CH2CH3 5-[5-bromo- 1 -(4-ethy Iphenyl)- 1 H-pyrazol-4- C6H4 yl]-2-( 1 -methy lethy l)-2H-tetrazole
418 Br CH(CH3)2 4 5-[5-bromo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-
OCH3C6H4 4-yl]-2-(l -methylethy l)-2H-tetrazole
419 Br CH(CH3)2 2CH3CgH4 5-[5-bromo-l -(2-methylphenyl)- lH-pyrazol-4- yl]-2-(l -methylethyI)-2H-tetrazole
420 Br CH(CH3)2 4CH3C6H4 5-[5-bromo- 1 -(4-methy Iphenyl)- 1 H-pyrazol-4- y l]-2-( 1 -methylethy l)-2H-tetrazole
421 Br CH2C6H5 CH3 2-benzyl-5-(5-bromo- 1 -methyl- 1 H-pyrazol-4- yl)-2H-tetrazole
422 Br CH2CeH5 CH2CH3 2-benzy l-5-(5-bromo- 1 -eth l- 1 H-pyrazol-4- yl)-2H-tetrazole
423 Br CH2C6H5 (CH3)2CH 2-benzy l-5-[5-bromo- 1 -(2-methy lpropy 1)- 1 H- CH2 pyrazol-4-yl]-2H-tetrazole
424 Br CH2C6H5 CH2Ph 2-benzy l-5-(l -benzyl-5-bromo-lH-pyrazol-4- yl)-2H-tetrazole
425 Br CH2C6H5 C6H5 2-benzy l-5-(5-bromo- l -phenyl- lH-pyrazol-4- yl)-2H-tetrazole
426 Br CH C6Hs 2 CIC6H4 2-benzy l-5-[5-bromo- l -(2-chlorophenyl)-lH- pyrazol-4-yl]-2H-tetrazole
121 427 Br GH2C6H5 3 CI C6H4 2-benzyl-5-[5-bromo- l -(3-chlorophenyl)- lH- pyrazol-4-yl]-2H-tetrazole
428 Br CH2C6H5 4 CI C6H4 2-benzy l-5-[5-bromo- 1 -(4-chlorophenyl)- 1 H- pyrazol-4-yl]-2H-tetrazole
429 Br CH2C6H5 2,3 Cl2 2-benzyl-5-[5-bromo- 1 -(2,3-dichlorophenyl)- C6H3 lH-pyrazol-4-yl]-2H-tetrazole
430 Br CH2CeH5 2,4 Cl2 2-benzyl-5-[5-bromo- l-(2,4-dichlorophenyl)- .
C6H3 lH-pyrazol-4-yl]-2H-tetrazole
431 Br CH2C6H5 2,5 Cl2 2-benzyl-5-[5-bromo- l -(2,5-dichlorophenyl)- C5H3 lH-pyrazol-4-yl]-2H-tetrazole
432 Br CH2C6H5 2,6 Cl2 2-benzyI-5-[5-bromo- 1 -(2,6-dichlorophenyl)- C6H3 lH-pyrazol-4-yl]-2H-tetrazole
433 Br CH2C6H5 3,4 Cl2 2-benzyl-5-[5-bromo- l -(3,4-dichlorophenyl)- C6H3 lH-pyrazol-4-yl]-2H-tetrazole
434 Br CH2C6H5 3,5 Cl2 2-benzyl-5-[5-bromo- l-(3,5-dichlorophenyl)- C6H3 lH-pyrazol-4-yl]-2H-tetrazole
435 . Br CH2C6H5 2 Br C¾H4 2-benzyl-5-[5-bromo- 1 -(2-bromophenyl)- 1 H- pyrazol-4-yl]-2H-tetrazole
436 Br CH2CgH5 3 Br CgH4 2-benzyl-5-[5-bromo- 1 -(3-bromophenyl)- 1 H- pyrazol-4-yl]-2H-tetrazo!e
437 Br CH2C6H5 4 Br C6H4 2-benzyl-5-[5-bromo- l -(4-bromophenyl)- l H- pyrazol-4-yl]-2H-tetrazole
438 Br CH2C6H5 4 F C6H4 2-benzy l-5-[5-bromo- 1 -(4-fluoropheny 1)- 1 H- pyrazol-4-yl]-2H-tetrazole
439 Br CH2C6H5 2 F C6H4 2-benzyl-5-[5-bromo- 1 -(2-fluorophenyl)- 1H- pyrazol-4-yl]-2H-tetrazole
440 Br CH2C6H5 2,3(CH3)2 2-benzyl-5-[5-bromo-l-(2,3-dichlorophenyl)- C6H3 lH-pyrazol-4-yl]-2H-tetrazole
441 Br CH2C6H5 2,4(CH3)2 2-benzyl-5-[5-bromo-l -(2,4-dichlorophenyl)- C6H3 lH-pyrazol-4-yl]-2H-tetrazole
442 Br CH2C6H5 2,5(CH3)2 2-benzyl-5-[5-bromo-l -(2,5-dichlorophenyl)- C6H3 lH-pyrazol-4-yl]-2H-tetrazole
443 Br CH2C6H5 2,6(CH3)2 2-benzyl-5-[5-bromo- l -(2,6-dichlorophenyl)- C6H3 lH-pyrazol-4-yl]-2H-tetrazole
444 Br CH2C6H5 3,4(CH3)2 2-benzy l-5-[5-bromo- 1 -(3,4-dichloropheny 1)- C6H3 lH-pyrazol-4-yl]-2H-tetrazole
445 Br CHjCeHs 3,5(CH3)2 2-benzyl-5-[5-bromo- 1 -(3,5-dichloropheny 1)- C6H3 1 H-py razol-4-y 1] -2H-tetrazo 1 e
446 Br CH2C6H5 2CH2CH3 2-benzy l-5-[5 -bromo-1 -(2-ethy Iphenyl)- 1 H- CeH4 pyrazol-4-yl]-2H-tetrazole
447 Br CH2C6H5 4CH2CH3 2-benzyl-5-[5-bromo- l -(4-ethylphenyl)-lH- C6H4 pyrazol-4-yl]-2H-tetrazole
448 Br CH2C6H5 4 2-benzyl-5-[5-bromo- l -(4-methoxyphenyl)-
OCH3C6H4 lH-pyrazol-4-yl]-2H-tetrazole
449 Br CH2C6H5 2CH3C6H4 2-benzyl-5-[5-bromo- 1 -(2-methy Iphenyl)- 1 H- pyrazol-4-yl]-2H-tetrazole
450 Br CH2C6H5 4CH3C6H4 2-benzyl-5-[5-bromo- l -(4-methy Iphenyl)- 1H- pyrazol-4-yl]-2H-tetrazole
451 Br 4BrC6H4 CH3 2-(4-bromobenzyl)-5-(5-bromo- l -methyl- 1H-
122 CH2 pyrazol-4-yl)-2H-tetrazole
452 Br 4BrC6H4 ' CH2CH3 2-(4-bromobenzyl)-5-(5-bromo-l -ethyl- 1 H- CH2 pyrazol-4-yl)-2H-tetrazole
453 Br 4BrC6H4 (CH3)2CH 2-(4-bromobenzyl)-5-[5-bromo- l -(2- CH2 CH2 methylpropy 1)- 1 H-pyrazol-4-yI]-2H-tetrazole
454 Br 4BrC6H4 CH2Ph 5-(l-benzyl-5-bromo- lH-pyrazol-4-yl)-2-(4- CH2 bromobenzyl)-2H-tetrazole
455 Br 4BrC6H4 C6H5 2-(4-bromobenzy l)-5-(5-bromo- 1 -phenyl- 1 H- CH2 pyrazol-4-yl)-2H-tetrazole
456 Br 4BrC6H4 2 ClCgH4 2-(4-bromobenzyl)-5-[5-bromo-l -(2- CH2 chloropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazoIe
457 Br 4BrC6H4 3 CI C6H4 2-(4-bromobenzyl) 5-[5-bromo- l -(3- CH2 chlorophenyl)- lH-pyrazol-4-yl]-2H-tetrazole
458 Br 4BrC6H4 4 CI C6H4 2-(4-bromobenzy l)-5-[5-bromo-l -(4- CH2 chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole
459 Br 4BrC6H4 2,3 Cl2 2-(4-bromobenzyl)-5-[5-bromo- l -(2,3- CH2 CeH3 dichIorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole
460 Br 4BrC6H4 2,4 Cl2 2-(4-bromobenzyl)-5-[5-bromo-l -(2,4- CH2 CeH3 dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole
461 Br 4BrC6H4 2,5 Cl2 2-(4-bromobenzyl)-5-[5-bromo-l -(2,5- CH2 C6¾ dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole
462 Br 4BrC6H4 2,6 Cl2 2-(4-bromobenzyl)-5-[5-bromo- l -(2,6- CH2 CeH3 dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole
463 Br 4BrC6H4 3,4 Cl2 2-(4-bromobenzyl)-5-[5-bromo- 1 -(3,4- CH2 C6H3 dichlorophenyl)- lH-pyrazol-4-yl]-2H-tetrazole
464 Br 4BrC6H4 3,5 Cl2 2-(4-bromobenzyI)-5-[5-bromo- 1 -(3,5- CH2 C6H3 dichloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole
465 Br 4BrC6H4 2 Br C6H4 2-(4-bromobenzy I)-5-[5-bromo- 1 -(2- CH2 bromophenyl)- lH-pyrazol-4-yl]-2H-tetrazole
466 Br 4BrC6H4 3 Br C6H4 2-(4-bromobenzyl)-5-[5-bromo- l -(3- CH2 bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole
467 Br 4BrC6H4 4 Br C6H4 2-(4-bromobenzyl)-5-[5-bromo- 1 -(4- CH2 bromophenyl)- lH-pyrazol-4-yl]-2H-tetrazole
468 Br 4BrC6H4 4 F C6H4 2-(4-bromobenzyl)-5-[5-bromo- l -(4- CH2 fluorophenyl)- lH-pyrazol-4-yl]-2H-tetrazole
469 Br 4BrC6H4 2 F CgH4 2-(4-bromobenzyl)-5-[5-bromo- 1 -(2- CH2 fluorophenyl)- lH-pyrazol-4-yl]-2H-tetrazole
470 Br 4BrC6H4 2,'3 (CH3)2 2-(4-bromobenzyl)-5-[5-bromo-l -(2,3- CH2 C6H3 dimethylphenyl)- l H-pyrazol-4-yl]-2H- tetrazole
471 Br 4BrC6H4 2,4(CH3)2 2-(4-bromobenzyl)-5-[5-bromo- 1 -(2,4- CH2 C6H3 dimethy lpheny 1)- 1 H-pyrazol-4-y 1]-2H- tetrazole
472 Br 4BrC6H4 2,5(CH3)2 2-(4-bromobenzyl)-5-[5-bromo- l -(2,5- CH2 C6H3 dimethylphenyl)- lH-pyrazol-4-yl]-2H- tetrazole
473 Br 4BrC6H4 2,6(CH3)2 2-(4-bromobenzyl)-5-[5-bromo- 1 -(2,6- CH2 CeH3 dimethy lpheny l)- lH-pyrazol-4-yl]-2H- tetrazole
123 474 Br 4BrC6H4 3,4(CH3)2 2-(4-bromobenzyl)-5-[5-bromo- l -(3,4- CH2 C6H3 dimethylphenyl)- lH-pyrazol-4-yl]-2H- tetrazole
475 Br 4BrC6H4 3,5 (CH3)2 2-(4-bromobenzyl)-5-[5-bromo- l -(3,5- CH2 CgH3 dimethy lpheny 1)- 1 H-pyrazol-4-y 1]-2H- tetrazole
476 Br 4BrC6H4 2CH2CH3 2-(4-bromobenzyl)-5-[5-bromo-l -(2- CH2 C6H4 ethylphenyl)-lH-pyrazoI-4-yl]-2H-tetrazole
477 Br 4BrC6H4 4CH2CH3 2-(4-bromobenzyl)-5-[5-bromo-l -(4- CH2 C6H4 ethylphenyl)- lH-pyrazol-4-yl]-2H-tetrazole
478 Br 4BrC6H4 4 2-(4-bromobenzyl)-5-[5-bromo-l -(4- CH2 OC H3C6H4 methoxyphenyl)- lH-pyrazol-4-yl]-2H- tetrazole
479 Br 4BrC6H4 2CH3C6H4 2-(4-bromobenzyl)-5-[5-bromo- l -(2- CH2 methylphenyl)- lH-pyrazol-4-yl]-2H-tetrazole
480 - Br 4BrC6H4 4 CH3C6H4 2-(4-bromobenzyl)-5-[5-bromo- l -(4- CH2 methylphenyl)- lH-pyrazol-4-yl]-2H-tetrazole
481 Br 4CNC6H4 CH3 4-{ [5-(5-bromo-.1 -methyl- 1 H-pyrazoi-4-y 1)- CH2 2H-tetrazol-2-yl]methyl}benzonitrile
482 Br 4CNC6H4 CH2CH3 4-{[5-(5-bromo- l -ethyl- lH-pyrazol-4-yl)-2H- CH2 tetrazol-2-yl]methyl}benzonitrile
483 Br 4CNC6H4 (CH3)2CH 4-({5-[5-bromo-l -(2-methylpropyl)- l H- CH2 CH2 pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile
484 Br 4CNC6H4 CH2Ph 4-{ [5-( 1 -benzyl-5-bromo- 1 H-pyrazol-4-yl)- CH2 2H-tetrazol-2-yl]methyl} benzonitrile
485 Br 4CNC6H4 C6H5 4-{[5-(5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)- CH2 2H-tetrazol-2-yl]methyl} benzonitrile
486 Br 4CNC6H4 2 C1C6H4 4-({5-[5-bromo-l -(2-chlorophenyl)- lH- CH2 pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile
487 Br 4CNC6H4 3 CI CgHU 4-({5-[5-bromo-l -(3-chlorophenyl)- lH- CH2 pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile
488 Br 4CNC6H4 4 CI C6H4 4-({5-[5-bromo-l -(4-chlorophenyl)- l H- CH2 pyrazol-4-yl]-2H-tetrazol-2- yl} methyl)benzonitrile
489 Br 4CNC6H4 2,3 Cl2 4-( { 5-[5-bromo- 1 -(2,3-dichlorophenyl)- 1 H- CH2 C6H3 pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile
490 Br 4CNC6H4 2,4 Cl2 4-({5-[5-bromo-l -(2,4-dichlorophenyl)- l H- CH2 C6H3 pyrazol-4-yl]-2H-tetrazol-2- yl} methyl)benzonitrile
491 Br 4CNC6H4 2,5 Cl2 4-({5-[5-bromo- l -(2,5-dichlorophenyl)- lH- CH2 C6H3 py razo 1 -4-y 1 ] -2H-tet razo 1 -2 - yl}methyl)benzonitrile
492 Br 4CNC6H4 2,6 Cl2 4-({5-[5-bromo- l -(2,6-dichlorophenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2H-tetrazol-2- yl} methyl)benzonitrile
124 493 Br 4CNC6H4 3,4 Cl2 4-( { 5-[5-bromo- 1 -(3,4-dichlorophenyl)- 1 H- " CH2 C6H3 pyrazol-4-yl]-2H-tetrazol-2- yl} methyl)benzonitrile
494 Br 4CNC6H4 3,5 Cl2 4-({5-[5-bromo-l -(3;5-dichlorophenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile
495 Br 4CNC6H4 2 Br C6H4 4-({ 5-[5-bromo- 1 r(2-bromopheny 1)- 1 H- CH2 pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile
496 Br 4CNC6H4 3 Br C6H4 4-({5-[5-bromo-l -(3-bromophenyl)- lH- CH2 py razo 1 -4-y 1] -2H-tetrazo 1 -2 - yl} methyl)benzonitrile
497 Br 4CNC6H4 4 Br C6H4 4-({5-[5-bromo-l -(4-bromophenyl)- l H- CH2 pyrazol-4-yl]-2H-tetrazol-2- y 1 } methy l)benzonitri le
498 Br 4CNC6H4 4 F C6H4 4-( { 5-[5 -bromo- 1 -(4-fluoropheny 1)- 1 H- CH2 pyrazol-4-yl]-2H-tetrazol-2- yl}methyI)benzonitrile
499 Br 4CNC6H4 2 F C6H4 4-( {5-[5-bromo- 1 -(2-fluoropheny 1)- 1 H- CH2 pyrazol-4-yl]-2H-tetrazol-2- y 1 } methyl)benzonitri le
500 Br 4CNC6H4 2,3 (CH3)2 4-({5-[5-bromo-l -(2,3-dimethylphenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2H-tetrazoi-2- yl} methyl)benzonitriIe
501 Br 4CNC6H4 2,4(CH3)2 4-( { 5-[5 -bromo- 1 -(2,4-dimethy lpheny 1)- 1H- CH2 CgH3 pyrazol-4-yl]-2H-tetrazol-2- y 1 } methy l)benzon itri le
502 Br 4CNC6H4 2,5 (CH3)2 4-({5-[5-bromo-l -(2,5-dimethylphenyl)-lH- CH2 CgH3 pyrazol-4-yl]-2H-tetrazol-2- y 1 } methyl)benzonitrile
503 Br 4CNC6H4 2,6 (CH3)2 4-({5-[5-bromo-l-(2,6-dimethylphenyl)-lH- CH2 CgH3 pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile
504 Br 4CNC6H4 3,4 (CH3)2 4-({5-[5-bromo- l-(3,4-dimethylphenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile
505 Br 4CNC6H4 3,5 (CH3)2 4-({5-[5-bromo- l -(3,5-dimethylphenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2H-tetrazol-2- y 1 } methyl)benzonitri le
506 Br 4CNC6H4 2CH2CH3 4-({5-[5-bromo-l -(2-ethylphenyl)- lH-pyrazol- CH2 ΟόΗ4 4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile
507 Br 4CNC6H4 4CH2CH3 4-({5-[5-bromo- 1 -(4-ethylpheny 1)- 1 H-pyrazol- CH2 CeH4 4-yl]-2H-tetrazol-2-yl} methyl)benzonitrile
508 Br 4CNC6H4 4 4-( { 5-[5 -bromo- 1 -(4-methoxypheny 1)- 1 H- CH2 OCH3C6H4 pyrazol-4-yl]-2H-tetrazol-2- yI}methyl)benzonitrile
509 Br 4CNC6H4 2 CH3CeH4 4-({5-[5-bromo- l -(2-methylphenyl)- lH- CH2 pyrazol-4-yl]-2H-tetrazol-2- yl} methyl)benzonitrile
125 Br 4CNC6H 4 CH3C6H4 4-({5-[5-bromo- 1 -(2-methy!phenyl)- 1H- CH2 pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile
Br 4CH3OC6 CH3 5-(5-bromo- 1 -methyl- 1 H-pyrazol-4-y!)-2-(4- H4CH2 methoxybenzyl)-2H-tetrazoIe
Br 4CH3OC6 CH2CH3 5-(5-bromo- 1 -ethyl- 1 H-pyrazol-4-y l)-2-(4- H4CH2 methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 (CH3)2CH 5-[5-bromo-l -(2-methylpropyl)-l H-pyrazol-4- H4CH2 CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC CH2Ph 5-( 1 -benzyl-5-bromo- 1 H-pyrazol-4-yl)-2-(4- H4CH2 methoxybenzy])-2H-tetrazole
Br 4CH3OC6 C6H5 5-(5-bromo-l -phenyl- lH-pyrazol-4-y l)-2-(4- H4CH2 methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 2 C1C6H4 5-[5-bromo- l -(2-chlorophenyl)T lH-pyrazol-4- H4CH2 yI]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 3 CI C6H4 5-[5-bromo- 1 -(3-chlorophenyl)- 1 H-pyrazol-4- H4CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 4 CI C6H4 5-[5-bromo- 1 -(4-chloropheny 1)- 1 H-pyrazol-4- H4CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 2,3 Cl2 5-[5-bromo- l -(2,3-dichlorophenyl)- l H- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC6 2,4 Cl2 5-[5-bromo-l -(2,4-dichlorophenyl)- lH- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC6 2,5 Cl2 5-[5-bromo- l -(2,5-dichlorophenyl)- lH- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC6 2,6 Cl2 5-[5-bromo- 1 -(2,6-dichloropheny 1)- 1 H- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC6 3,4 Cl2 5-[5-bromo-l -(3,4-dichlorophenyl)- lH- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenz.yl)-2H- tetrazole
Br 4CH3OC6 3,5 Cl2 5-[5-bromo-l -(3,5-dichlorophenyl)- l H- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC6 2 Br C6H4 5-[5-bromo- l -(2-bromophenyl)-lH-pyrazol-4- H4CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 3 Br C6H4 5-[5-bromo- 1 -(3-bromopheny 1)- 1 H-pyrazol-4- H4CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 4 Br C6H4 5-[5-bromo-l-(4-bromophenyl)- l H-pyrazol-4- H4CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 4 F C6H4 5-[5-bromo-l -(4-fluorophenyI)-lH-pyrazol-4- H4CH2 y]]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 2 F C6H4 5-[5-bromo- 1 -(2-fluoropheny 1)- 1 H-pyrazol-4- H4CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 2,3 (CH3)2 5-[5-bromo- l -(2,3-dimethylphenyl)- l H- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-
126 tetrazole
Br 4CH3OC6 2,4 (CH3)2 5-[5-bromo- 1 -(2,4-dimethylphenyl)- 1 H- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC6 2,5 (CH3)2 5-[5-bromo-l -(2,5-dimethylphenyl)- lH- H4CH2 CeH3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC6 2,6 (CH3)2 5-[5-bromo- 1 -(2,6-dimethylphenyl)- 1H- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC6 3,4 (CH3)2 5-[5-bromo- 1 -(3,4-dimethylphenyl)- 1 H- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC6 3,5 (CH3)2 5-[5-bromo-l -(3,5-dimethylphenyl)- lH- H4CH2 C6H3 pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole
Br 4CH3OC 2 CH2CH3 5-[5-bromo- l -(2-ethylphenyl)- lH-pyrazol-4- H4CH2 C H4 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 4 CH2CH3 5-[5-bromo- l -(4-ethylphenyl)- lH-pyrazol-4- H4CH2 C6H4 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 40CH3 5-[5-bromo-l -(4-methoxyphenyl)- l H-pyrazol- H4CH2 C6H4 4-yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 2 CH3C6H4 5-[5-bromo- l -(2-methy Ipheny l)- lH-pyrazol-4- H4CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 4CH3OC6 4 CH3C6H4 5-[5-bromo- 1 -(4-methy Ipheny 1)- 1 H-pyrazol-4- H4CH2 yl]-2-(4-methoxybenzyl)-2H-tetrazole
Br 3CH3C6H4 CH3 5-(5-bromo-l -methyl- lH-pyrazol-4-y l)-2-(3- CH2 methylbenzyl)-2H-tetrazole
Br 3CH3CgH4 CH2CH3 5-(5-bromo- 1 -ethyl- 1 H-pyrazol-4-y l)-2-(3- CH2 methylbenzyl)-2H-tetrazole
Br 3CH3C6H4 (CH3)2CH 5-[5-bromo- 1 -(2-methy Ipropyl)- 1 H-pyrazol-4- CH2 CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
Br 3CH3C6H4 CH2Ph 5-(l -benzyl-5-bromo- lH-pyrazol-4-yl)-2-(3- CH2 methylbenzyl)-2H-tetrazole
Br 3CH3C6H4 C6H5 5-(5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)-2-(3- CH2 methylbenzyl)-2H-tetrazole
Br 3CH3C6H4 2 C1C6H4 5-[5-bromo- l -(2-chlorophenyl)-l H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
Br 3CH3CgH4 3 CI C6H4 5-[5-bromo- 1 -(3-chloropheny 1)- 1 H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
Br 3CH3C6H4 4 CI C6H4 5-[5-bromo- 1 -(4-chloropheny 1)- 1 H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
Br 3CH3C¾H4 2,3 Cl2 5-[5-bromo- 1 -(2,3-dichlorophenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
Br 3CH3C6H4 2,4 Cl2 5-[5-bromo- 1 -(2,4-dichloropheny 1)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
Br 3CH3C6H4 2,5 Cl2 5-[5-bromo- l -(2,5-dichlorophenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
127 552 Br 3CH3C6H4 2,6 Cl2 5-[5-bromo- 1 -(2,6-dichlorophenyl)- lH- CH2 C5H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
553 Br 3CH3C6H4 3,4 Cl2 5-[5-bromo-l -(3,4-dichlorophenyl)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
554 Br 3CH3C6H4 3,5 Cl2 5-[5-bromo- 1 -(3,5-dichlorophenyl)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
555 Br 3CH3C6H4 2 Br C6H4 5-[5-bromo-l -(2-bromophenyl)- lH-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
556 Br 3CH3C6H4 3 Br C6H4 5-[5-bromo- l -(3-bromophenyl)- lH-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
557 Br 3CH3C6H4 4 Br C6H4 5-[5-bromo- 1 -(4-bromophenyl)- lH-pyrazol-4- CH2 yl]-2-(3-methyIbenzyl)-2H-tetrazole
558 Br 3CH3C6H4 4 F C6H4 5-[5 -bromo- 1 -(4-fluoropheny 1)- 1 H-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
559 Br 3CH3C6H4 2 F C6H 5-[5-bromo-l -(2-fluorophenyl)-lH-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
560 Br 3CH3C6H4 2,3(CH3)2 5-[5-bromo- 1 -(2,3-dimethylphenyl)- 1H- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
561 Br 3CH3C6H4 2,4(CH3)2 5-[5-bromo-l-(2,4-dimethylphenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
562 Br 3CH3C6H4 2,5(CH3)2 5-[5-bromo- l -(2,5-dimethylphenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
563 Br 3CH3C6H4 2,6(CH3)2 5-[5-bromo- 1 -(2,6-dimethylpheny 1)- 1 H- CH2 C6H3 py razo 1-4-y l]-2-(3 -methy 1 benzy l)-2H-tetrazole
564 Br 3CH3C6H4 3,4(CH3)2 5-[5-bromo-l -(3,4-dimethylphenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
565 Br 3CH3C6H4 3,5((CH3)2 5-[5-bromo-l-(3,5-dimethylphenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole
566 Br 3CH3C6H4 2CH2CH3 5-[5-bromo- l -(2-ethylphenyl)-lH-pyrazol-4- CH2 C6H4 yl]-2-(3-methylbenzyl)-2H-tetrazole
567 Br 3CH3C6H4 4CH2CH3 5-[5-bromo-l -(4-ethylphenyl)- lH-pyrazol-4- CH2 C6H4 yl]-2-(3-methylbenzyl)-2H-tetrazole
568 Br 3CH3C6H4 4 5-[5-bromo- 1 -(4-methoxyphenyl)- 1 H-pyrazol- CH2 OCH3C6H4 4-yl]-2-(3-methylbenzyl)-2H-tetrazole
569 Br 3CH3C6H4 2 CH3C6H4 5-[5-bromo- l -(2-methylphenyl)- lH-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
570 Br 3CH3C6H4 4 CH3C6H4 5-[5-bromo- 1 -(4-methylphenyl)- lH-pyrazol-4- CH2 yl]-2-(3-methylbenzyl)-2H-tetrazole
571 Br 4N02C6H4 CH3 5-(5-bromo- l -methyl- lH-pyrazol-4-y l)-2-(4- CH2 nitrobenzyl)-2H-tetrazole
572 Br 4N02C6H4 CH2CH3 5-(5-bromo- 1 -ethyl- 1 H-pyrazol-4-yl)-2-(4- CH2 nitrobenzyl)-2H-tetrazole
573 Br 4N02C6H4 (CH3)2CH 5-[5-bromo- 1 -(2-methy lpropyl)- 1 H-pyrazol-4- CH2 CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazoIe
574 · Br 4NG2C6H4 CH2Ph 5-(l-benzyl-5-bromo- lH-pyrazol-4-yl)-2-(4- CH2 nitrobenzyl)-2H-tetrazole
575 Br 4N02C6H4 C6H5 5-(5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)-2-(4- CH2 n itrobenzy l)-2H-tetrazo le
576 Br 4N02C6H4 2 ClCgH4 5-[5-bromo-l -(2-chlorophenyl)- l H-pyrazol-4-
128 CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
577. Br 4N02C6H4 3 CI C6H4 5-[5-bromo- l -(3-chlorophenyl)-l H-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
578 Br 4N02C6H4 4 CI C6H4 5-[5-bromo- 1 -(4-chlorophenyl)- 1 H-pyrazoI-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
579 Br 4N02C6H4 2,3 Cl2 5-[5-bromo- 1 -(2,3-dichlorophenyl)- 1H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
580 Br 4N02C6H4 2,4 Cl2 5-[5-bromo-l -(2,4-dichlorophenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
581 Br 4N02C6H4 2,5 Cl2 5-[5-bromo-l -(2,5-dichlorophenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole ,
582 Br 4N02C6H4 2,6 Cl2 5-[5-bromo- 1 -(2,6-dichlorophenyl)- 1H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
583 Br 4N02C6H4 3,4 Cl2 5-[5-bromo- l -(3,4-dichlorophenyl)- l H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
584 Br 4N02C6H4 3,5 Cl2 5-[5-bromo-l -(3,5-dichlorophenyl)- lH- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
585 Br 4N02C6H4 2 Br C6H4 5-[5-bromo-l -(2-bromophenyl)- lH-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
586 Br 4N02C6H4 3 Br C6H4 5-[5-bromo- 1 -(3-bromophenyl)- 1 H-pyrazol-4r
CH2 yi]-2-(4-nitrobenzyl)-2H-tetrazole
587 Br 4N02C6H4 4 Br C6H4 5-[5-bromo- 1 -(4-bromopheny 1)- 1 H-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
588 Br 4N02e6H4 4 F C6H4 5-[5-bromo- 1 -(4-fluoropheny 1)- 1 H-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
589 Br 4N02C6H4 2 F C6H4 5-[5-bromo- 1 -(2-fluoropheny 1)- lH-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
590 Br 4N02C6H4 2,3(CH3)2 5-[5-bromo- 1 -(2, 3-dimethy Ipheny 1)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
591 Br 4N02C6H4 2,4(CH3)2 5-[5-bromo-l -(2,4-dimethylpheny 1)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
592 Br 4N02C6H4 2,5(CH3)2 5-[5-bromo- l-(2,5-dimethylphenyl)-lH- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
593 Br 4N02C6H4 2,6(CH3)2 5-[5-bromo- 1 -(2,6-dimethylphenyl)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
594 Br 4N02C6H4 3,4(CH3)2 5-[5-bromo- 1 -(3,4-dimethy Ipheny 1)- 1 H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
595 Br 4N02C6H4 3,5(CH3)2 5-[5-bromo-l -(3,5-dimethylphenyl)- 1H- CH2 C6H3 pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
596 Br 4N02C6H4 2CH2CH3 5-[5-bromo- 1 -(2-ethylphenyl)- 1 H-pyrazol-4- CH2 CeH4 yl]-2-(4-nitrobenzyl)-2H-tetrazole
597 Br 4N02C6H4 4CH2CH3 5-[5-bromo-l -(4-ethy Ipheny 1)- 1 H-pyrazol-4- CH2 C6H4 yl]-2-(4-nitrobenzyl)-2H-tetrazole
598 Br 4N02C6H4 4 5-[5-bromo- 1 -(4-methoxypheny 1)- 1 H-pyrazol- CH2 OCH3C6H4 4-yl]-2-(4-nitrobenzyl)-2H-tetrazole
599 Br 4N02C6H4 2CH3CeH4 5-[5-bromo- l -(2-methylphenyl)- lH-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
600 Br 4N02C6H4 4 CH3C6H4 5-[5-bromo- 1 -(4-methy Ipheny 1)- 1 H-pyrazol-4- CH2 yl]-2-(4-nitrobenzyl)-2H-tetrazole
129 Example 7: 5-(5-chloro-l-methyl-lH-pyrazol-4-yl)-2-methyl-2H-tetrazole (Compound 61)
Step 1 : 2-methyl-5-(l-methyl- lH-pyrazol-4-yl)-2H-tetrazole
A mixture of 5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole (100 gm, 0.6660 moles), potassium hydroxide (74.74 gm, 1.332 moles) and acetonitrile (500 ml) were stirred for 10 min at 20-25 °C. To the above mixture added methyl iodide (378.12 gm, 2.664 moles), stirred for about 10-15 hour at 20-25°C and progress of the reaction was monitored by HPLC. Excess acetonitrile was recovered at 60-70°C at reduced pressure. DCM (500 ml) and DM water (500 ml) was added to the reaction mixture, stirred for 30 min and the reaction mixture was kept undisturbed for 15 min. The organic layer was separated and aqueous layer was extracted with DCM (500 ml), stirred for 10 min and separated the final aqueous layer and organic layer. The organic layer was evaporated to obtain the 2-methyl-5- (1 -methyl- l H-pyrazol-4-yl)-2H-tetrazole, or l-methyl-5-( l -methyl- l H-pyrazol-4-y 1)-2H- tetrazole, or mixture thereof. The desired regio-isomer, 2-methyl-5-( l -methyl- lH-pyrazol- 4-yl)-2H-tetrazole, was isolated by column chromatography using ethyl acetate and hexane as eluent.
Dry wt 46 gm
Yield 0.46 w/w (42%)
HPLC purity 99.97
MP 172-175°C
Step 2: 5-(5-chloro-l -methyl-lH-pyrazol-4-yl)-2-methyl-2H-tetrazole
To a solution of 2-methyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole (10 gm, 0.609 moles) in acetonitrile (50 ml) was added N-chlorosuccinimide (8.22 gm, 0.0615 moles). The reaction mixture was stirred for 30 min at 60°C. Progress of the reaction was monitored by HPLC. Excess acetonitrile was recovered at 40-50°C under reduced pressure. DI water ( 100 ml) was poured to the crude product at 20-25 °C. The reaction mixture was stirred for 1 hours at 20-25°C, filtered the product, washed with cold DM water (50 ml) and dried at 60- 70°C to obtain the product, 5-(5-chloro-l -methyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole.
Dry wt 1 1 gm
Yield 1 .1 w/w (91%)
HPLC purity 99.51 %
MP 125- 127°C
130 In accordance with the present disclosure, the halogenations of 2-methyl-5-( l -methyl- l H- pyrazol-4-yl)-2H-tetrazole may preceed the methylation step to obtain the compound of formula. I.
Example 8: 5-(5-chloro-l-methyl-lH-pyrazol-4-yl)-2-methyl-2H-tetrazole (Compound 61)
Step 1: l -methyl-lH-pyrazole-4-carbaldehyde
A mixture of phosphory! chloride (467 gm, 3.045 moles) and DMF was stirred for 1 hour at 0-5°C. The reaction is exothermic so temperature should be below 5°C. To this slowly added 1 -methyl- I H-pyrazole (50 gm, 0.6090 moles) and stirred for 30 min at 0-5°C. Then slowly raised the temperature from 20-30°C to 60-70°C and stirred for 10-15 hours. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0- 5°C, to this added ethyl acetate (250 ml), DM water (1 L) and aqueous ammonia solution (350 ml, pH-6 to 7). The reaction mixture was stirred for 1 hour at 20-30°C. The inorganic salt obtained was filtered off, washed with ethyl acetate (250 ml). The filtrate was transferred in to a separating funnel. The reaction mixture was allowed to settle. The organic layer was separated and aqueous layer was extracted with ethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel, stirred for 10- 15 min and separated the final aqueous layer and organic layer. The combined organic layer having 1 - methyl- lH-pyrazole-4-carbaldehyde and ethyl acetate was used as such for Step 2 without any purification or isolation at this step.
Step 2: 1 - methyl -lH-pyrazole-4-carbaldehyde oxime
A mixture of the combined organic layer having 1 -methyl- lH-pyrazole-4-carbaldehyde and ethyl acetate obtained from step 1 and hydroxylamine hydrochloride (63.48 gm, 0.9135 moles) was refluxed at 70-80°C for 2-4 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-5°C, to this added DM water (100 ml) and 25% aqueous ammonia solution ( 100 ml) at 0-5°C. The reaction mixture was stirred for 10 min at 20-30 °C. The organic layer was separated and aqueous layer was extracted with ethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (500 ml). Stirred for 10 min and separated the final aqueous layer and organic layer. The organic layer was evaporated to obtain the 1 -methyl- 1 H-pyrazole-4-carbaldehyde oxime.
Dry wt : 70 gm
Yield : 1.40 w/w (90%) HPLC purity : 99.85%
Step 3: 5-( l -methyl-lH-pyrazol-4-yl)-2H-tetrazole
1 - Methyl- 1 H-pyrazole-4-carbaldehyde oxime (84 gm, 0.6713 moles) obtained in step 2, ammonium chloride (89.77 gm, 1.6783 moles), sodium azide ( 109.1 1 gm, 1.6783 moles) were taken in DMF (420 ml). The reaction mixture was stirred for about 10- 12 hours at 100-120°C. The progress of the reaction was monitored by HPLC. To the above reaction mixture at 0-10°C, added DM water (500 ml). The reaction mixture was stirred for 2 hours at 0- 10°C, filtered the product, washed with cold DM water (200 ml) and air dried the product, 5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole at 60-70°C.
Dry wt : 70 gm
Yield : 0.83w/w (69%)
HPLC purity : 99.98%
Step 4: 2-methyl-5-(l -methyl- l H-pyrazol-4-yl)-2H-tetrazole
2- methyl-5-(l -methyl- l H-pyrazol-4-yl)-2H-tetrazole was prepared from 5-(l - methyl-l H-pyrazol-4-yl)-2H-tetrazole as obtained in step 3, by a process of example 7, step 1.
Step 5: 5-(5-chloro- l -methyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole
5-(5-chloro- l -methyl- l H-pyrazol-4-yl)-2-methyl-2H-tetrazole was obtained by the process as described in step 2 of example 7.
Compounds 62- 330 were prepared by following the experimental procedure of
Example 7 or 8 using appropriate intermediates.
Example 9: 5-(5-chIoro-l-methyl-lH-pyrazoI-4-yI)-2-methyl-2H-tetrazoIe (Compound 61)
Step 1 : 4-iodo-l -methyl- lH-pyrazole
A mixture of 1 -methyl- lH-pyrazole (7) (37 gm, 0.6090 moles), iodine (57.1 gm, 0.225 moles), hydrogen peroxide (9.2 gm, 0.27 moles) and D| water ( 1 10 ml) were stirred for 24 hour at 20-30°C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 5-10°C. The reaction mixture was quenched with 20% aqueous sodium bisulfate (100 ml) and stirred for 1 hour at 5- 10°C. The solid obtained was filtered, washed with cold DI water (100 ml) and dried at 40-45°C to obtain the product, 4-iodo- l - methyl-lH-pyrazole.
Dry wt : 56 gm
Yield : 1.51 w/w (60%)
132 Step 2: 1 -Methyl- 1 H-pyrazole-4-carbonitrile
To a solution of 4-iodo-l -methyl- lH-pyrazole (55 gm, 0.264 moles) in N,N- dimethylacetamide (100 ml), potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles) and sodium carbonate (27.98 gm, 0.264 moles) were added. The reaction mixture was evacuated and backfilled with nitrogen (3 times). The mixture was stirred for 12 hour at 100-1 10°C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30°C, to this added DI water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30°C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 min and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70°C. The mixture was degassed for 2 hour at reduced pressure at 60-70°C, cooled the mixture to 20-30°C: Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30°C. The solid product obtained was filtered, washed with cold DI water ( 100 ml) and dried at 40-50°C to afford the product, 1 -Methyl- 1 H- pyrazole-4-carbonitrile. .
Dry wt : 17.94 gm
Yield : 0.32 w/w (63%);
Step 3: 5-( l -Methyl- lH-pyrazol-4-yl)-2H-tetrazole
1 -Methyl- 1 H-pyrazole-4-carbonitrile ( 18 gm, 0.168 moles) obtained in step 2, tri-w- butyl tin chloride (65 gm, 0.218 moles), sodium azide ( 14 gm, 0.201 moles) were taken in toluene (180 ml). The reaction mixture was stirred for 24 hours at 100- 120°C. The progress of the reaction was monitored by HPLC. The above reaction mixture was cooled to 10- 15°C, to this added 10% ethanol ic HC1 solution ( 100 ml, pH= 1 -2). The reaction mixture was stirred for 1-1.5 hours at 10-15°C, filtered off the inorganic salts, washed with ethanol (30 ml). The mother liquor, and washings were collected and toluene and ethanol were recovered at 50-55°C at reduced pressure. To the above residue at 20-25°C, added di- isopropyl ether (100 ml), stirred for 1 -2 hours at 20-25°C, filtered the solid, washed with di- isopropyl ether (30 ml) and air dried the product, 5-( l -methyl- l H-pyrazol-4-yl)-2H- tetrazole at 60-65°C.
Dry wt : 25 gm
Yield : 1.4 w/w (99%)
Theoretical yield : 1.40 w/w
133 Step 4: 2-methyl-5-(l -methyl- l H-pyrazol-4-yl)-2H-tetrazole
The preparation of 2-methyl-5-(l -methyl- l H-pyrazol-4-yl)-2H-tetrazole was carried out in a manner similar to that described in Step 1 of Example 7.
Step 5: 5-(5-chloro-l -methyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole
The 5-(5-chloro-l -methyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole was synthesized according to the method described in Step 2 of Example 7.
Although the subject matter has been described in considerable detail with reference to certain preferred embodiments thereof, other embodiments are possible. As such, the spirit and scope of the present disclosure should not be limited to the description of the preferred embodiment contained therein.
134

Claims

We claim:
1 . A compound of formula I, its derivatives salts, stereo-isomers or regio-isomers thereof,
Figure imgf000129_0001
Formula 1
wherein:
Ri is selected from H, CI, Br or I;
R2 is selected from hydrogen or a straight chain or a branched C|_7 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C 1 -5 alkyl, phenyl, or a C 1 -C4 alkoxy; and
R3 is selected from a straight or a branched chain Q.7 alkyl; or a C6-C 14 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, Ci_5 alkyl, phenyl, or a C| -C4 alkoxy;
with the proviso that when R| is H; R2 is not methyl.
2. The compound as claimed in claim 1, wherein:
Ri is selected from H, CI, Br or I;
R2 is selected from hydrogen or a or straight chain or a branched C 1.3 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from Br, N02, CN, Ci_5 alkyl, or a C 1 -C4 alkoxy; and
R3 is selected from a straight or a branched chain Cj_4 alkyl; or a C6 aryl group,
wherein said straight or branched chain alkyl is optionally substituted with a phenyl group;
135 said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, Ci .2 alkyl, or C 1 -C4 alkoxy; .
with the proviso that when R| is H; R2 is not methyl.
The compound as claimed in claim 1, wherein:
Ri is selected from CI, Br or I;
R2 is selected from hydrogen or a straight chain or a branched C 1 -7 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C\s alkyl, phenyl, or a Q-C4 alkoxy; and
R3 is selected from a straight or a branched chain C 1 -7 alkyl or a C6-C14 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C 1 -5 alkyl, phenyl or a C 1 -C4 alkoxy. ,
The compound as claimed in claim 1 , wherein:
R i is selected from CI, Br or I;
R2 is hydrogen or methyl; and
R3 is selected from a straight or a branched chain C 1.7 alkyl; or a C6-C i4 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, F, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C|_5 alkyl, or a C 1 -C4 alkoxy.
The compound as claimed in claim 1 selected from:
5- l -methyl-l H-pyrazol-4-yl)-2H-tetrazoIe;
5- 1 -ethyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
5- l -(2-methylpr0pyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5- 1 -benzyl- l H-pyrazol-4-yl)-2H-tetrazole;
5- 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
5- l -(2-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5- 1 -(3-chloropheny I)- 1 H-pyrazol-4-y l]-2H-tetrazoIe;
5- l -(4-chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5- 1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
136 -[l-(2,4-dichIorophenyI)-lH-pyrazol-4-yl]-2H-tetrazole;
-[l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-[l-(2,6-dichlorophenyI)-lH-pyrazol-4-yl]-2H-tetrazole;
-[ 1 -(3,4-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
-[l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-[l-(2-bromophenyl)-lH-pyrazoI-4-yl]-2H-tetrazole;
-[l-(3-bromophenyl)-lH-pyrazol-4-yI]-2H-tetrazole;
-[l-(4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-[l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-[ 1 -(2-fluoropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;
-[ 1 -(2,3-dimethy Iphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazoie;
-[l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-[ 1 -(2,5-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
-[ 1 -(2,6-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
-[l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-[l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-[l -(2-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
-[ί -(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
-[l-(4-methoxyphenyl)-lH-pyrazol-4-yI]-2H-tetrazole;
-[ 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
-[l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazoie;
-(5-chloro-l -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
-(5-chloro-l -ethyl- lH-pyrazoI-4-yl)-2H-tetrazole;
-[5-chloro- 1 -(2-methy lpropyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;-(l-benzyI-5-chloro-l H-pyrazol-4-yl)-2H-tetrazole;
-(5-chloro- 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-[5-chloro-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-chloro-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-chloro-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-chloro-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-chloro-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;-[5-chloro-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2Hrtetrazole;-[5-chloro- 1 -(2,6-dichlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
137 5- 5-chloro- l-(3,4-dichlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole; 5- 5-chloro- 1 -(3, 5-dichlorophenyl)-l H-pyrazoI-4-yl]-2H-tetrazole; 5- l-(2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2H-tetrazole; 5- l -(3-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2H-tetrazole; 5- l -(4-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-chloro- l -(4-fluorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-chloro- l -(2-fluorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 5- 5-chloro- 1 -(2,3-dimethy Ipheny I)- 1 H-pyrazol-4-y l]-2H-tetrazole; 5- 5-chloro- 1 -(2,4-dimethylphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazo!e; 5- 5-chloro- 1 -(2, 5-dimethy Ipheny l)- l H-pyrazol-4-yl]-2H-tetrazole; 5-, 5-chloro- 1 -(2, 6-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 5-, 5-chloro- 1 -(3, 4-dimethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-chloro- 1 -(3, 5-dimethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazo!e; 5- 5-chloro- l -(2-ethylphenyl)- lH-pyrazol-4-yl]-2H-tetrazole; 5-1 5-chloro- l -(4-ethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5-1 5-chloro- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 5- 5-chloro- l -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-chloro- 1 -(4-methy Iphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole; 5- 5-bromo- l -methyl- l H-pyrazoI-4-yl)-2H-tetrazole;
5- 5-bromo-l -elhyl- l H-pyrazol-4-yl)-2H-tetrazole;
5- 5-bromo-l -(2-methylpropyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5- l -benzyl-5-bromo- l H-pyrazol-4-yl)-2H-tetrazole;
5- 5-bromo-l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
5- 5-bromo-l -(2-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-bromo-l -(3-chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-bromo-l -(4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-bromo-l -(2,3-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-bromo-l -(2,4-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-bromo-l -(2, 5-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-bromo- 1 -(2,6-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 5- 5-bromo-l -(3,4-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-bromo- l -(3, 5-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 5- 5-bromo- 1 -(2-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
138 5· 5-bromo- l-(3-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5- 5-bromo- 1 -(4-bromophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
5· 5-bromo- 1 -(4-fIuoropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
5-15-bromo-l -(2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5- 5-bromo-l -(2,3-dimethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5· 5 -bromo- 1 -(2,4-dimethy lpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
5- 5-bromo- l-(2,5-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5- 5-bromo- 1 -(2,6-dimethylphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
5- 5-bromo- l -(3,4-dimethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5-1 5-bromo- 1 -(3, 5-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5- 5-bromo- 1 -(2-ethy lpheny 1)- 1 H-py razol-4-y l]-2H-tetrazole;
5· 5-bromo- 1 -(4-ethylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
5- 5-bromo- 1 -(4-methoxypheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;
5· 5-bromo- l -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5· 5-bromo- 1 -(4-methylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
5-15-iodo-l -methyl-l H-pyrazol-4-yl)-2H-tetrazole;
5- l-ethyl-5-iodo-l H-pyrazol-4-yl)-2H-tetrazole;
5- 5-iodo-l-(2-methylpropyl)-l H-pyrazoI-4-yl]-2H-tetrazole;
5· 1 -benzyl-5-iodo- 1 H-pyrazol-4-y l)-2H-tetrazole;
5- 1 -(2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5- l -(3-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5· l -(4-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-1 1 -(2,3-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
5- 1 -(2,4-dichlorOphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
5· l -(2,5-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5- l -(2,6-dichlorophenyl)-5-iodo-l H-pyrazol.-4-yl]-2H-tetrazole;
5- l -(3,4-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-1 l -(3,5-dichlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-1 l -(2-bromophenyl)-5-iodo-l H-pyrazoI-4-yl]-2H-tetrazole;
5-1 l -(3-bromophenyl)-5-iodo-l H-pyrazol-4-yI]-2H-tetrazole;
5-1 l -(4-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5- l-(4-f!uorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-1 1 -(2-fluoropheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
139 5-[l-(2,3-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-[l-(2,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-[l-(2,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-[l-(2,6-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-[l-(3,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-[l-(3,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-[l-(2-ethyIphenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole;
5-[l-(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
5-[5-iodo-l-(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-[5-iodo-l-(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; and
5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
The compound as claimed in claim 1 is selected from:
5-(l -ethyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5-( 1 -ethyl- 1 H-pyrazoI-4-yI)- 1 -methyl-2H-tetrazole;
2-methyI-5-[l-(2-methylpropyl)-lH-pyrazoI-4-yl]-2H-tetrazole;
1 -methyl-5-[l -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
5-( 1 -benzyl- 1 H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5-( 1 -benzyl- 1 H-pyrazol-4-y I)- 1 -methyl-2H-tetrazole;
2-methyl-5-(l -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 -methyl-5-( 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
5-[ 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[ 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole;
5-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-[ 1 -(3-chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole;
5-[ 1 -(4-chlorophenyl)- 1 H-pyrazol-4-yl]-2-methy l-2H-tetrazole;
5-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5-[l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole
5-[l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole
5-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole
5-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole
5-[l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole
5-[l -(2,5-dichlorophenyl)-l H-pyrazol-4-yI]- 1 -methy!-2H-tetrazole.
5-[l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
140 5- -(2,6-dichlorophenyl)- l H-pyrazol-4-yl]- l -methyl-2H-tetrazole;
5· -(3,4-dichlorophenyl)- l H-pyrazoI-4-yl]-2-methyl-2H-tetrazole;
5-1 -(3,4-dichloropheny 1)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5· -(3,5-dichlorophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- -(3,5-dichlorophenyl)-l H-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5· -(2-bromophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-1 -(2-bromopheny I)- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole;
5· -(3-bromophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5· -(3-bromophenyi)- 1 H-pyrazol-4-yI]- 1 -methyl-2H-tetrazole;
5· -(4-bromopheny 1)- 1 H-pyrazol-4-yl]-2-methy l-2H-tetrazole;
5- -(4-bromopheny 1)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5· -(4-fluorophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- -(4-fluoropheny 1)- 1 H-pyrazol-4-y 1J- 1 -methy l-2H-tetrazole;
5- -(2-fluorophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- -(2-fluorophenyl)- l H-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- 2,3-dimethylphenyl)-l H-pyrazol 4 -y 1] -2 -m eth y 1 -2 H -tetrazo le
5-1 2.3- dimethylphenyl)- 1 H-pyrazo -4-y 1]- 1 -methy 1-2 H-tetrazole
5- 2.4- dimethy Ipheny 1)- 1 H-pyrazol -4-yl]-2-methyl-2H-tetrazole
5· 2.4- dimethylphenyl)- l H-pyrazol■4-yl]- 1 -methy 1-2 H-tetrazole
5- 2.5- dimethylphenyl)-l H-pyrazol■4-yl]-2-methyl-2H-tetrazole
5-1 l -i 2.5- dimethylphenyl)-l H-pyrazol■4-yl]- 1 -methy l-2H-tetrazole
5 2.6- dimethylphenyl)- 1 H-pyrazol■4-yl]-2-methyl-2H-tetrazole
5- 2,6-dimethylphenyl)-l H-pyrazol■4-yl]- 1 -methy l-2H-tetrazole
5· 3, 4-dimethylphenyl)-l H-pyrazol■4-y l]-2-m ethy I -2 H-tetrazo le
5-1 3.4- dimethylphenyl)- l H-pyrazol 4-yl]- -methy l-2H-tetrazole
5- 3.5- dimethy Ipheny 1)- 1 H-pyrazol 4-yl]-2-methyl-2H-tetrazole
5- 3, 5-dimethylphenyl)- l H-pyrazol 4-yl]- 1 -methy l-2H-tetrazole
5· 2-ethylphenyl)- 1 H-pyrazol-4-y 1} 2 -m ethy 1 -2 H-tetrazo 1 e ;
5- l -i 2-ethylphenyl)-l H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole;
5- 4-ethylpheny 1)- 1 H-pyrazol-4-y 1]· 2-methyl-2H-tetrazole;
5-1 4-ethylphenyl)-l H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole;
5- 4-methoxyphenyl)- l H-pyrazol-4 yl]-2-methyl-2H-tetrazole;
5· 4-methoxyphenyl)- 1 H-pyrazol-4 y 1]- 1 -methy l-2H-tetrazole;
141 2-methyl-5-[l -(2-methylphenyl)- l H-pyrazoI-4-yl]-2H-tetrazole;
1 -methyl-5-[ 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2-methyl-5-[l -(4-methylphenyI)-l H-pyrazol-4-yl]-2H-tetrazole;
l -methyl-5-[ l -(4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5- 5-chloro-l -methyl- 1 H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- 5-chloro-l-methyl-lH-pyrazol-4-yl)-l -methyl-2H-tetrazole;
5- 5-chloro- l -ethyl- l H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- 5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)-l -methyl-2H-tetrazole;
5- 5-chloro-l -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5- 5-chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole; 5- 1 -benzyl-5-chloro- 1 H-pyrazol-4-yl)-2-methy I-2H-tetrazole;
5- l -benzyl-5-chloro-l H-pyrazol-4-yl)-l -methyl-2H-tetrazole;
5- 5-chloro- phenyl- l H-pyrazol-4-yl)-2-methyl-2H-tetrazoie;
5- 5-chloro- phenyl- l H-pyrazol-4-yl)- l -methyl-2H-tetrazole;
5- 5-chloro- 2-chlorophenyl)- 1 H-pyrazol-4-yl]-2-methyI-2H-tetrazole; 5- 5-chloro- 2- chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole; 5- 5-chloro- 3- chlorophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5- 5-chloro- 3- chloropheny 1)- 1 H-pyrazol-4-y 1]- 1 -methyl-2H-tetrazole; 5- 5-chloro- 4- chlorophenyl)-l.H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5- 5-chloro- 4-chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole; 5- 5-chloro- 2,3 -dichlorophenyl)- 1 H -pyrazol -4-yl]- 2-methyI-2H- -tetrazole; 5- 5-chloro- 2,3 -dichlorophenyl)- 1 H -pyrazol -4-ylJ- -1 -methy 1-2 H -tetrazole; 5- 5-chloro- 2,4 ■dichlorophenyl)- 1 H -pyrazol -4-yl]- 2-methyl-2H -tetrazole; 5- 5-chloro- 2,4 -dichlorophenyl)- l H -pyrazol -4-yl]- l -methyl-2H -tetrazole; 5- 5-chloro- 2,5 -dichlorophenyl)- 1 H -pyrazol -4-yl]- 2-methyl-2H -tetrazole; 5- 5-chloro- 2,5 -dichlorophenyl)- I H -pyrazol -4-yl]- l -methyl-2H- -tetrazole; 5- 5-chloro- 2,6 -dichlorophenyl)- 1 H -pyrazol -4-yl]- -2-methyl-2H -tetrazole; 5- 5-chloro- 2,6 -dichlorophenyl)- 1 H -pyrazol -4-yl]- -l -methyl-2H -tetrazole; 5- 5-chloro- 3,4 -dichlorophenyl)- I H -pyrazol -4-yl]- 2-methyl-2H -tetrazole; 5- 5-chloro- 3,4 -dichlorophenyl)- I H -pyrazol -4-yl]- l -methyl-2H- -tetrazole; 5- 5-chloro- 3,5 -dichlorophenyl)- I H -pyrazol -4-yl]- 2-methyl-2H- -tetrazole; 5-, 5-chloro- l 3,5- •dichlorophenyl)- I H- -pyrazol- -4-yl]- l -methyl-2H- -tetrazole; 5- 1 -(2-bromophenyl)-5-chloro- 1 H-pyrazol-4-y l]-2-methyl-2H-tetrazole;
142 5· 1 -(2-bromophenyl)-5-chloro- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5· 1 -(3-bromopheny l)-5-chloro- l H-pyrazoI-4-yl]-2-methyl-2H-tetrazole;
5- 1 -(3-bromopheny l)-5-chloro- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole;
5: l -(4-bromophenyl)-5-chloro- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-1 1 -(4-bromophenyI)-5-chloro- l H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5 -chloro- 4-fluorophenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5· -chloro- 4-fluorophenyl)- l H-pyrazol-4-yl]- l -methyl-2H-tetrazole;
5-1 -chloro- 2-fluorophenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5· -chloro- 2-fIuorophenyl)- 1 H-pyrazoI-4-y 1]- 1 -methyl-2H-tetrazole;
5- -chloro- 2,3-dimethylphenyl H-pyrazol-4-yl -2-methyl- -2H -tetrazole
5· ■chloro- 2.3- dimethylphenyl H-pyrazol-4-yl - 1 -methy 1- -2H -tetrazole
5· ■chloro- 2.4- dimethy Iphenyl H-pyrazo!-4-yl -2-methyl- -2H- -tetrazole
5-1 •chloro- 2.4- dimethylphenyl H-pyrazol-4-yl - 1 -methy 1■ -2H- -tetrazole
5· •chloro- 2.5- dimethylphenyl H-pyrazol-4-yl -2-methyl- -2H -tetrazole
5· ■chloro- 2.5- dimethylphenyl H-pyrazol-4-yl - 1 -methy 1- ■2H- -tetrazole
5- ■chloro- 2.6- dimethylphenyl H-pyrazol-4-yl -2-methyl- -2H- -tetrazole
5· ■chloro- 2,6-dimethylphenyl H-pyrazol-4-yl - 1 -methyl- -2H- -tetrazole
5- ■chloro- 3,4-dimethylphenyl H-pyrazol-4-yl -2-methyl- -2H- -tetrazole
5- -chloro- 3.4- dimethylphenyl H-pyrazol-4-yl - 1 -methy 1- -2H -tetrazole
5- •chloro- 3.5- dimethylphenyl H-pyrazol-4-yl -2-methyl- -2H- -tetrazole
5- ■chloro- 3,5-dimethylphenyl H-pyrazol-4-yl - 1 -methyl- ■2H- -tetrazole
5- ■chloro- 2-ethylpheny 1)- 1 H-pyrazol-4-yl]-2-methy l-2H-tetrazole;
5- ■chloro- 2-ethylphenyl)- l H-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5- ■chloro- 4-ethylphenyl)- 1 H-pyrazol-4-y l]-2-methyl-2H-tetrazole;
5· -chloro- 4-ethylphenyl)- H-pyrazol-4-yl]-l -methyl-2H-tetrazole;
5-1 •chloro- 4-methoxyphenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- ■chloro- 4-methoxyphenyl)- l H-pyrazol-4-yl]- l -methy l-2H-tetrazole;
5- ■chioro- 2-methylphenyl)- l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- ■chloro- 2-methylphenyl)- l H-pyrazol-4-yl]- l -methyl-2H-tetrazole;
5- ■chloro- 4-methy lphenyl)- 1 H-pyrazol-4-y l]-2-methy l-2H-tetrazole;
5- •chloro- 4-methylphenyl)- l H-pyrazol-4-yl]- l -methy l-2H-tetrazole;
5-1 ■bromo- methy l- l H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5· ■bromo- methyl- 1 H-pyrazol-4-y I)- 1 -methy l-2H-tetrazole;
143 5- (5-bromo- 1 -ethyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- (5-bromo- 1 -ethyl- lH-pyrazol-4-yl)-l-methyl-2H-tetrazole;
5- ^5-bromo- l-(2-methylpropyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- l-(2-methylpropyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- (1-benzyl- 5-bromo- 1 H-pyrazol-4-y l)-2-methyl-2H-tetrazole;
5- (1-benzyl- 5-bromo-lH-pyrazol-4-yl)-l-methyl-2H-tetrazole;
5- ;5-bromo- 1 -phenyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- (5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 -methyl-2H-tetrazole;
5- 5-bromo- l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
' 5- 5-bromo- l-(2-chIorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- 5-bromo- l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- l-(3-chlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- 5-bromo- l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
' 5- 5-bromo- 1 -(4-chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole;
5- 5-bromo- l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- 1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5- 5-bromo- 1 -(2,4-dichlorophenyl)- 1 H-pyrazol-4-y l]-2-methy l-2H-tetrazole;
5- 5-br6mo- l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- 5-bromo- l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- 5-bromo- 1 -(2,6-dichlorophenyl)- 1 H-pyrazol-4-y l]-2-methy l-2H-tetrazole;
5- 5-bromo- 1 -(2,6-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5- 5-bromo- l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazoIe;
■ 5- 5-bromo- l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- l-(3,5-dichlorophenyl)-l H-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- 5-bromo- l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- 5-bromo- l-(2-bromophenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- 5-bromo- 1 -(3-bromophenyl)- 1 H-pyrazol-4-yl]-2-methy l-2H-tetrazole;
5- 5-bromo- 1 -(3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole;
5- "5-bromo- l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- L5-bromo- l-(4-bromophenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- ^5-bromo- 1 -(4-fluorophenyl)- 1 H-pyrazol-4-y l]-2-methyl-2H-tetrazole;
144 5- bromo 4-fluorophenyl)- l H-pyrazol-4-yl]- l -methyl-2H-tetrazole;
5- bromo 2-fluorophenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- bromo 2-fluorophenyl)- 1 H-pyrazol-4-y 1]- 1 -methy I-2H-tetrazole;
5· bromo 2,3 -dimethylphenyl)- I H -pyrazol-4-yl] -2 -methyl -2H -tetrazole
5- bromo 2,3 -dimethylphenyl)- I H- -pyrazol-4-yl] - 1 -methyl -2H -tetrazole
5- bromo 2,4 -dimethylphenyl)- I H- -pyrazol-4-yl]- -2 -methyl -2H -tetrazole
5- bromo 2,4 -dimethylphenyl)- I H -pyrazol-4-yl] -1 -methyl -2H -tetrazole
5- bromo 2,5 -dimethylphenyl)- I H -pyrazol-4-yl] -2 -methyl -2H -tetrazole
5- bromo 2,5 -dimethylphenyl)- I H -pyrazol-4-yl] - 1 -methyl -2H -tetrazole
5- -bromo 2,6 -dimethylphenyl)- I H- -pyrazoI-4-yl]- -2 -methyl- -2H -tetrazole
5- bromo 2,6 -dimethylphenyl)- IH- -pyrazol-4-yI]- - 1 -methyl -2H -tetrazole
5- bromo 3,4- -dimethylphenyl)- I H- -pyrazol-4-yl]- -2 -methyl- -2H -tetrazole
5-1 -bromo 3,4 -dimethylphenyl)- IH- -pyrazol-4-yl]- -1 -methyl- -2H -tetrazole
5· bromo 3,5- -dimethylphenyl)- I H- -pyrazol-4-yl] -2 -methyl -2H -tetrazole
5- -bromo 3,5 -dimethylphenyl)- I H- -pyrazol-4-yl]- - 1 -methyl- -2H -tetrazole
5-1 -bromo 2-ethylpheny 1)- 1 H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-1 bromo- 2-ethylphenyl)-l H-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5-1 bromo 4-ethylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- bromo 4-ethy Ipheny I)- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole;
5- -bromo 4-methoxypheny l)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5-1 bromo 4-methoxypheny I)- 1 H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole;
5- bromo- 2-methylphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- bromo 2-methylphenyl)-l H-pyrazol-4-yl]- 1 -methyl-2H-tetrazole;
5- bromo 4-methy Ipheny I)- 1 H-pyrazol-4-y l]-2-methyl-2H-tetrazole;
5: bromo 4-methylphenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5-1 iodo- 1 -methyl- 1 H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- iodo- 1 -methyl- 1 H-pyrazol-4-y 1)- 1 -methy l-2H-tetrazole;
5- ethyl-5-iodo- 1 H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5-( ethyl-5-iodo- 1 H-pyrazol-4-yl)- 1 -methy!-2H-tetrazole;
5- iodo- l -(2-methylpropyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- iodo-l -(2-methylpropyl)-lH-pyrazol-4-yl]- l -methy l-2H-tetrazole;
5- benzyl-5-iodo-l H-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- benzyl-5-iodo- l H-pyrazol-4-yl)-l -methy 1-2 H-tetrazole;
145 5- (5-iodo-l -phenyl- lH-pyrazol-4-yl)-2-methyl-2H-tetrazole;
5- (5-iodo-l -phenyl- lH-pyrazol-4-yl)-l-methyl-2H-tetrazole;
5- [i- (2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
' 5- [i- (2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- [i- (3-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [i- (3-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- [i- (4-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [i- (4-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- [i- (2,3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [i- 3,3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- [i- (2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [i- (2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- [i- (2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- Π- (2,5-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -methy l-2H-tetrazole;
5- [·- ^2,6-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [i- (2,6-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-y 1]-1 -methy l-2H-tetrazole;
5- [i- (3,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [i- (3,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
. 5- [i- (3,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [i- ^3,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- [i- -bromophehyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [i- ;2-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;'
5- [1- ^3-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- ;i- 3-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole;
5- ;i- (4-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- ;i- (4-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazo!e;
5- Ί- ;4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- [i- (4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- [i- (2-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole;
5- ;i- -fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;
5- ;i- (2,3-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole
5- [\- (2,3-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole
5- [i- ,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole
146 5-[ 1 -(2,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]-l -methy l-2H-tetrazole 5-[l-(2,5-dimethylphenyI)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole 5-[ 1 -(2,5-dimethylpheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -methy 1-2 H-tetrazole 5-[l-(2,6-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole 5-[ 1 -(2,6-dimethylpheny !)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -methy l-2H-tetrazole 5-[l-(3,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole 5-[ 1 -(3,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -methy I -2 H-tetrazole 5-[l-(3,5-dimethylphenyI)-5-iodo-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole 5-[ 1 -(3,5-dimethy Ipheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -methy 1-2 H-tetrazole 5-[l-(2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2-methyl-2H.-tetrazole; 5-[l-(2-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-[ 1 -(4-ethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2-methy l-2H-tetrazole; 5-[l-(4-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole; 5-[5-iodo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-iodo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-l -methy l-2H-tetrazole; 5-[5-iodo-l-(2-methylphenyl)-l H-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-iodo- l-(2-methy Ipheny l)-t H-pyrazol-4-yl]-l -methy l-2H-tetrazole; 5-[5-iodo-l-(4-methy Ipheny l)-lH-pyrazol-4-yl]-2-methyl-2H-tetrazole; 5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-l-methyl-2H-tetrazole;' 2-ethyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
1- ethyl-5-(l -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2- ethyl-5-(l-ethyl-lH-pyrazol-4-yl)-2H-tetrazole;
1- ethyl-5-(l-ethyl-lH-pyrazol-4-yl)-2H-tetrazole;
2- ethyl-5-[ 1 -(2-methylpropyI)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1- ethyl-5-[l-(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5-(l -benzyl- lH-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5-( 1 -benzyl- 1 H-pyrazol-4-y 1)- 1 -ethyl-2H-tetrazole;
2- ethyl-5-( 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
l-ethyI-5-(l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
5-[ 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]-2-ethy l-2H-tetrazole;
5-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
5-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5-[ 1 -(3-chloropheny 1)- 1 H-pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole;
147 5- [i- (4-chlorophenyl)-l H -pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- [i- (4-chlorophenyl)-l H -pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole;
5- [i- (2,3-dichlorophenyl) ■lH-pyrazol-4-yl]-2-ethyi-2H-tetrazole;
5- [i- (2,3-dichlorophenyl)- ■ 1 H-pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole;
5- [i- (2,4-dichlorophenyl)- -lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5- [i- (2,4-dichlorophenyl)- ■1 H-pyrazol-4-yl]- l-ethy l-2H-tetrazole;
'5- [i- (2,5-dichlorophenyl)- lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- [i- (2,5-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole;
5- [i- (2,6-dichlorophenyl)- 1 H-pyrazol-4-yI]-2-ethyl-2H-tetrazole;
5- ;ι- (2,6-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole;
5- 1- ^3,4-dichlorophenyl)- lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- 1- (3,4-dichlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -ethyl-2H-tetrazole;
5- 1- ,5-dichlorophenyl)- lH-pyrazol-4-yl]-2-ethyl-2H-tetrazo!e;
5-1 1- (3,5-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 -ethy l-2H-tetrazole;
5- 1- ^2-bromophenyl)-l H -pyrazol-4-yl]-2-ethyl-2H-tetrazoIe;
5- 1- ^2-bromopheny 1)- 1 H ■pyrazol-4-y 1]- 1 -ethyl-2H-tetrazole;
5- 1- ;3-bromophenyl)-l H -pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- 1- (3-bromophenyl)- 1 H ■pyrazol-4-yl]-l-ethyl-2H-tetrazole;
5-1 1- ^4-bromophenyl)- 1 H- ■pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5-1 1- ^4-bromophenyl)- 1 H- ■pyrazol-4-yl]- 1 -ethyl-2H-tetrazole;
2-ethyl-5-[l-(4-fluorophenyl)-lH-pyrazol-4 yl]-2H-tetrazole;
1 - ethyl-5-[l -(4-fluoropheny 1)- 1 H-pyrazol-4 yl]-2H-tetrazole;
2- ethyl-5-[l-(2-fluorophenyl)-lH-pyrazol-4 yl]-2H-tetrazole; 1 -ethy l-5-[ 1 -(2-fluorophenyl)- 1 H-pyrazol-4 yl]-2H-tetrazole; 5-[l-(2,3-dimethylphenyl)-l H-pyrazol-4-yl ]-2-ethyl-2H-tetrazole 5-[l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl ]-l-ethyl-2H-tetrazole 5-[l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl ]-2-ethyl-2H-tetrazole 5-[l -(2,4-dimethy lpheny I)- 1 H-pyrazol-4-yl ]-l-ethyl-2H-tetrazole; 5-[l -(2,5-dimethylphenyl)-l H-pyrazol-4-yl ]-2-ethyl-2H-tetrazole 5-[l-(2,5-dimethy Iphenyl)- 1 H-pyrazol-4-yl ]-l-ethyl-2H-tetrazole; 5-[l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl ]-2-ethyl-2H-tetrazole; 5-[l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl ]-l-ethyl-2H-tetrazole: 5-[l-(3,4-dimethylphenyl)-l H-pyrazol-4-yl ]-2-ethyl-2H-tetrazole:
148 5-[l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
5-[l-(3,5-dimethyIphenyl)-lH-pyrazol-4-yl]-2-et yl-2H-tetrazole;
5-[l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
2-ethyl-5-[l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- ethyl-5-[l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5-[l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- ethyl-5-[l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- ethy|-5-[l -(4-methoxyphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1- ethyl-5-[l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5-[l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- ethyl-5-[l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5-[l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
l-ethyl-5-[l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
5-(5-chloro-l -methyl- lH-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5-(5-chloro-l -methyl- lH-pyrazol-4-yl)-l-ethyl-2H-tetrazole;
5-(5-chloro-l -ethyl- lH-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5-(5-chloro-l -ethyl- lH-pyrazol-4-yl)-l-ethyl-2H-tetrazole;
5-[5-chloro-l-(2-methylpropyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-chloro-l-(2-methylpropyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-(l-benzyl-5-chloro-lH-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5-(l-benzyl-5-chloro-lH-pyrazol-4-yl)-l-ethyl-2H-tetrazole;
5-(5-chloro-l -phenyl- lH-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5-(5-chloro- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 -ethyl-2H-tetrazole;
5-[5-chloro- 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-chloro- 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole; 5-[5-chloro-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-chloro- 1 -(3-chlorophenyI)- 1 H-pyrazol-4-yl]- 1 -ethy l-2H-tetrazole; 5-[5-chloro-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-chloro-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-[5-chloro-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-chloro- 1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 -ethyl-2H-tetrazole; 5-[5-chloro-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-chloro- 1 -(2,4-dichloropheny 1)- 1 H-pyrazol-4-yl]- 1 -ethy l-2H-tetrazole;
149 5- -chloro- 1 -(2,5-dichloropheny I)- 1 H-pyrazol-4-y l]-2-ethy l-2H-tetrazole
5- ■chloro-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole
5- ■chloro- 1 -(2, 6-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole
5- ■chloro- 1 -(2,6-dichloropheny 1)- 1 H-pyrazoI-4-yl]- 1 -ethy l-2H-tetrazole
5- -chloro-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole
5- -chloro- 1 -(3,4-dichlorophenyI)- 1 H-pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole
5· -chloro- 1 -(3,5-dichlorophenyl)- 1 H-pyrazol-4-yl]-2-ethy l-2H-tetrazole
5- -chloro- 1 -(3, 5-dichlorophenyl)-lH-pyrazol-4-yl]-l -ethy l-2H-tetrazole
5- -(2-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- -(2-bromophenyl)-5-chloro- H-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
5- -(3-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- -(3-bromopheny l)-5-chloro- 1 H-pyrazol-4-yl]- 1 -ethyI-2H-tetrazole;
5- (4-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- -(4-bromophenyl)-5-chloro-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
5- ■chloro- 1 4-fluorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- chloro- 1■ 4-fluorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
5-1 chloro- 1■ 2-fluorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- chloro-l- 2-fluorophenyl)- 1 H-pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole;
5· chloro- 1■ 2,3 -dimethylphenyl) -1H -pyrazol-4-yl]
5· ■chloro-l- 2,3 -dimethylphenyr -1H -pyrazol-4-yl]
5-1 chloro-l- 2,4 -dimethylphenyl) -1H -pyrazol-4-yl]
5- ■chloro-l- 2,4 -dimethylphenyr -1H -pyrazol-4-yl]
5· chloro-l- 2,5 -dimethylphenyl) -1H -pyrazol-4-yl]
5- chloro-l- 2,5 ■dimethylphenyr -1H -pyrazol-4-yl]
5- chloro-l- 2,6 -dimethylphenyl) -1H -pyrazol-4-yl]
5- chloro-l- 2,6 -dimethylphenyl) -1H -pyrazol-4-yl]
5- chloro-l- 3,4 -dimethylphenyl) -1H -pyrazol-4-yl]
5-1 chloro- 1 - 3,4- -dimethylphenyl) -1H -pyrazol-4-yl]
5· chloro-l- 3,5 -dimethylphenyl) -1H -pyrazol-4-yl]
5- chloro-l- 3,5- -dimethylphenyl) -1H -pyrazol-4-yl]
5- chloro-l- 2-ethylphenyl)- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
5- chloro- 1 - 2-ethylphenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole;
5- chloro-l- 4-ethy Ipheny 1)- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
150 chloro-1- (4-ethylpheny I)- 1 H-pyrazol-4-y I]- 1 -ethy l-2H-tetrazole;
5-1 chloro-1- (4-methoxyphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5- chloro-1- (4-methoxyphenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5- chloro-1- (2-methylphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5- chloro-1- (2-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -ethy l-2H-tetrazole; 5- chloro-1- (4-methyIphenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5- chloro-1- (4-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -ethy 1-2 H-tetrazole; 5-( bromo-1- methyi-1 H-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5- bromo-1- methyl- lH-pyrazol-4-yl)-l -ethy l-2H-tetrazole;
5- bromo-l- ethyl- 1 H-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5- bromo-1- ethyl- lH-pyrazol-4-yI)-l -ethy l-2H-tetrazole;
5- bromo-l- (2-methylpropyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5- bromo-1- (2-methylpropyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5- benzyl-5-■bromo-lH-pyrazol-4-yl)-2-ethyl-2H-tetrazole; .
5-1 •benzyl-5 -bromo-l H-pyrazol-4-y I)- 1 -ethy l-2H-tetrazole;
5· bromo-l-■phenyl- 1 H-pyrazol-4-y l)-2-ethyl-2H-tetrazole;
5· bromo-1- phenyl- lH-pyrazol-4-yl)-l-ethyl-2H-tetrazole;
5· bromo-l- 2-chlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5· bromo-l- 2- chlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5· bromo-l- 3- chlorophenyI)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-1 bromo-1- 3- chlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5-1 ■bromo-l- 4- chlorophenyl)-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-! ■bromo-l- 4-chlorophenyl)-lH-pyrazol-4-yl]-l-ethyl-2H-tetrazole; 5- ■bromo-l- 2,3 -dichlorophenyl)- IH ■pyrazol -4-yl]- ■2-ethyl-2H -tetrazole 5· ■bromo-l- 2,3 -dichlorophenyl)- H ■pyrazol -4-yl]- -l-ethyl-2H -tetrazole 5- •bromo-l- 2,4 -dichlorophenyl)- H ■pyrazol -4-yl]- -2-ethyl-2H -tetrazole 5- ■bromo-l- 2,4 -dichlorophenyl)- H -pyrazol -4-yl]- l-ethyl-2H -tetrazole 5- •bromo-l- 2,5 -dichlorophenyl)- H -pyrazol -4-yl]- 2-ethyl-2H -tetrazole 5- ■bromo-l- 2,5 -dichlorophenyl)- 1H -pyrazol -4-yl]- ■l-ethyl-2H -tetrazole 5- ■bromo-l 2,6 -dichlorophenyl)- IH -pyrazol -4-yl] -2-ethyl-2H -tetrazole 5-1 ■bromo-l- 2,6 -dichlorophenyl)- IH -pyrazol -4-yl]- ■l-ethyl-2H -tetrazole
■bromo-l 3,4 -dichlorophenyl)- IH -pyrazol -4-yl]- ■2-ethyl-2H -tetrazole
•bromo-l- 3,4 -dichlorophenyl)- H -pyrazol -4-yl]- ■l-ethyl-2H -tetrazole
151 5-[5-bromo- (3,5-dichlorophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-bromo- (3,5-dichlorophenyl)-l H-pyrazoI-4-yl]- l -ethyl-2H-tetrazole; 5-[5-bromo- (2-bromophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-bromo- (2-broniophenyl)- 1 H-pyi-azol-4-yl]- 1 -ethy l-2H-tetrazole; 5-[5-bromo- (3-bromophenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-bromo- (3 -bromopheny 1)- 1 H-pyrazol-4-y 1]- 1 -ethy 1-2 H-tetrazole; 5-[5-bromo- -(4-bromophenyl)- l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5r[5-bromo- -(4-bromophenyl)- l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole; 5-[5-bromo- -(4-fluoropheny 1)- 1 H-pyrazol-4-y l]-2-ethy 1-2 H-tetrazole; 5-[5-bromo- -(4-fluorophenyl)-l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole; 5-[5-bromo- -(2-fluorophenyl)-lH-pyrazol-4-yl]-2-ethy 1-2 H-tetrazole; 5-[5-bromo- -(2-fluoropheny 1)- 1 H-pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole; 5-[5-bromo- -(2,3-dimethylphenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-[5-bromo- -(2,3-dimethy lphenyl)-.1 H-pyrazol-4-y 1]- 1 -ethyl-2H-tetrazole 5-[5-bromo- -(2,4-dimethylphenyl)-l H-pyrazol-4-yl]-2-ethy 1-2 H-tetrazole 5-[5-bromo- -(2,4-dimethylphenyl)-l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole 5-[5-bromo- -(2,5-dimethylphenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-[5-bromo- -(2,5-dimethylphenyl)-l H-pyrazol-4-yl]- l -ethyl-2H-tetrazoIe 5-[5-bromo- -(2,6-dimethylphenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole 5-[5-bromo- -(2,6-dimethylphenyl)- l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole 5-[5-bromo- -(3,4-dimethy lphenyl)- l H-pyrazol-4:yl]-2-ethyl-2H-tetrazole 5-[5-bromo- -(3,4-dimethylphenyl)-l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole 5-[5-bromo- -(3,5-dimethylpheny I)- 1 H-pyrazol-4-y l]-2-ethy 1-2 H-tetrazole 5-[5-bromo- -(3,5-dimethylphenyl)- 1 H-pyrazol-4-yl]- 1 -ethy 1-2 H-tetrazole 5-[5-bromo- -(2-ethylphenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-bromo- -(2-ethy lphenyl)- 1 H-pyrazol-4-y I]- 1 -ethy l-2H-tetrazole; 5-[5-bromo- -(4-ethylphenyl)- l H-pyrazol-4-yl]-2-ethy 1-2 H-tetrazole; 5-[5-bromo- -(4-ethylphenyl)-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5-[5-bromo- -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-bromo- -(4-methoxyphenyl)- l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5-[5-bromo- -(2-methylphenyl)-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[5-bromo- -(2-methylphenyl)- l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole; 5-r5-bromo- -(4-methylpheny 1)- 1 H-pyrazol-4-y l]-2-ethy 1-2 H-tetrazole;
152 5-[5-bromo- l -(4-methylphenyl)- l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole; 2-ethyl-5-(5-iodo-l -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
1 -ethy l-5-(5-iodo- 1 -methyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
2-ethyl-5-(l -ethyl-5-iodo-l H-pyrazol-4-yl)-2H-tetrazole;
1 - ethyl-5-(l -ethyl-5-iodo-lH-pyrazoI-4-yl)-2H-tetrazole;
2- ethyl-5-[5-iodo-l -(2-methylpropyl)- lH-pyrazol-4-yl]-2H-tetrazole;
1 - ethyl-5-[5-iodo-l -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole; 5-( l-benzyl-5-iodo-lH-pyrazol-4-yl)-2-ethyl-2H-tetrazole;
5-( 1 -benzyI-5-iodo- 1 H-pyrazol-4-yl)- 1 -ethyl-2H-tetrazo!e;
10 2- ethyI-5-(5-iodo- l -phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
1 -ethyl-5-(5-iodo- 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole
2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-ethyl-2H-tetrazoIe; 2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-l -ethyl-2H-tetrazole;
5' 1 -(3-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2-ethyl-2H-tetrazole;
,15 •5 1 -(3-chlorophenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -ethy l-2H-tetrazole;
5 4-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5 4-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -ethy 1-2 H-tetrazole; 5 2,3-dichlorophenyl)-5- odo- 1 H-pyrazol-4-yI -2-ethyl-2H- tetrazole 5 2.3- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl -l -ethyl-2H- tetrazole
20 5 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y I -2-ethyl-2H- tetrazole
5' 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 ■l -ethyl-2H- tetrazole 5 2.5- dichlorophenyl)-5- odo-l H-pyrazol-4-yl -2-ethyl-2H- tetrazole 5' 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -1 -ethy 1-2 H- tetrazole 5 2.6- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -2-ethyl-2H- tetrazole
25 5 2,6-dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -l -ethyl-2H- tetrazole
5 3,4-dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 ■2-ethyl-2H- tetrazole 5 1 - 3.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -l -ethyl-2H- tetrazole 5 3.5- dichlorophenyl)-5- odo-l H-pyrazol-4-yl ■2-ethyl-2H- tetrazole 5 3,5-dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1]- 1 -ethyl-2H-tetrazole
30 5 2-bromophenyl)-5-iodo-l H-pyrazoI-4-yl]-2-ethyl-2H-tetrazole;
5 2- bromopheny l)-5-iodo- 1 H-pyrazol-4-yl]- 1 -ethy l-2H-tetrazole; 5 3- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5 3-bromophenyl)-5-iodo-l H-pyrazol-4-yl]- l -ethyl-2H-tetrazole;
153 5-[l -(4-bromophenyl)-5-iodo- lH-pyrazol-4-yl]-2-ethyl-2H-tetrazole; 5-[ 1 -(4-bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -ethy l-2H-tetrazole; 2-ethyl-5-[l -(4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1- ethyl-5-[l -(4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5-[l -(2-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2H-tetrazole; l -ethyl-5-[l -(2-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2Hrtetrazole;
5- ; i -(2,3 -dimethylphenyl)-5 -iodo- 1 H-pyrazol -4 -yl] -2-ethyl-2H -tetrazole
5- ; i -(2,3 -dimethylphenyl)-5 -iodo- 1 H-pyrazol -4 -yl] -l -ethyl-2H -tetrazole
5- ; i -(2,4 -dimethylphenyl)-5 -iodo- 1 H-pyrazol -4 -yl] -2-ethyl-2H -tetrazole
5- : i -(2,4 -dimethylphenyl)-5 ■iodo- 1 H-pyrazol -4 -yl] - 1 -ethy 1-2 H -tetrazole
5- ;i -(2,5 -dimethylphenyl)-5 ■iodo- 1 H-pyrazol -4 -yl] -2-ethyl-2H -tetrazole
5- ;i -(2,5 -dimethylphenyl)-5 ■iodo- 1 H-pyrazol -4 -yl] - l-ethyl-2H -tetrazole
5- ;i -(2,6 -dimethylphenyl)-5 ■iodo- 1 H-pyrazol- -4 -yl] -2-ethyl-2H -tetrazole
5- ;i -(2,6 -dimethylphenyl)-5 -iodo- 1 H-pyrazol -4 -yl] -l-ethyl-2H -tetrazole
5- ;'l -(3,4 ■dimethylphenyl)-5- -iodo- l H-pyrazol- -4 -yl] -2-ethyl-2H -tetrazole
5- "l -(3,4 -dimethylphenyl)-5- -iodo- 1 H-pyrazol- -4 -yl] - l -ethyl-2H -tetrazole
5- l -(3,5 -dimethylphenyl)-5- ■iodo- 1 H-pyrazol- -4 -yl] -2-ethyl-2H -tetrazole
5- l -(3,5 -dimethylphenyl)-5- ■iodo- l H-pyrazol- -4- ■yi] -2-ethyl-2H- -tetrazole
2-ethyl-5-[l -(2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1- ethyl-5-[l -(2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5-[i -(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 1 -ethyl-5-[ 1 -(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 2-ethyl-5-[5-iodo-l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - ethyl-5-[5-iodo-l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- ethyl-5-[5-iodo-l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;. l -ethyl-5-[5-iodo-l-(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 2rethyl-5-[5-iodo-l-(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - ethyl-5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- ( 1 -methy lethy l)-5-( 1 -methyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
1 -( 1 -methy lethy l)-5 -( 1 -methyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
5-(l -ethyl- l H-pyrazol-4-yl)-2-(l -methylethyl)-2H-tetrazole;
5-( 1 -ethyl- 1 H-pyrazol-4-y 1)- 1 -( 1 -methy lethy l)-2H-tetrazole;
2-( 1 -methy lethy l)-5-[ 1 -(2-methy lpropy 1)- 1 H-py razol-4-y l]-2H-tetrazole;
154 -(l-methylethyl)-5-[l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;-( 1 -benzyl- 1 H-pyrazol-4-y l)-2-( 1 -methylethy l)-2H-tetrazole;
-( 1 -benzyl- 1 H-pyrazol-4-yl)- 1 -( 1 -methylethy l)-2H-tetrazole;
-( 1 -methylethy l)-5-( 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
-(1 -methylethy l)-5-( 1 -phenyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[ I -(2 -chlorophenyl)-lH-pyrazol-4-yl]-l-(l -methylethy l)-2H-tetrazole;-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[l-(4-chlorophenyl)-l H-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole-[ 1 -(2,3-dichloropheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methylethy l)-2H-tetrazole-[ 1 -(2,4-dichlorophenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole-[ 1 -(2, 5-dichloropheny 1)- 1 H-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole:-[l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole:-[ 1 -(2, 6-dichlorophenyl)- 1 H-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole:-[ 1 -(2,6-dichloropheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methylethy l)-2H-tetrazole:-[l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;-[l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole:-[l -(3, 5-dichloropheny l)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole:-[ 1 -(2-bromophenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methylethy l)-2H-tetrazole;-[ 1 -(2-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l)-2H-tetrazole;-[l-(3-hromophenyl)-lH-pyrazol-4-yl]-2-(l -methylethy l)-2H-tetrazole;-[ 1 -(3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethyl)-2H-tetrazole;-[ 1 -(4-bromophenyl)- 1 H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[ 1 -(4-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethy l)-2H-tetrazole;-[l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[l -(4-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l)-2H-tetrazole;-[l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;-[l-(2-fIuorophenyI)-l H-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole;
155 1 - (2,3 -dimethylphenyl)- I H•pyrazol-4■yl]-2-( 1 -methylethyl)- -2H -tetrazole;
1 - (2,3 -dimethylphenyl)- [ H -pyrazol-4 -yl]-H '\ -methy lethy 1)- -2H -tetrazole;
1 - (2,4 -dimethylphenyl)- H -pyrazol-4 ■yl]-2-( Ί -methylethyl)- -2H -tetrazole;
1 - (2,4 -dimethylphenyl)- H ■pyrazol-4 -yl]- l -( Ί -methylethyl)- -2H -tetrazole;
1 - (2,5 -dimethylphenyl)- I H -pyrazol-4 -yl]-2-( -methylethyl)- -2H -tetrazole;
1 - (2,5 -dimethylphenyl)- H -pyrazol-4 -yl]- H ^l -methylethyl)- -2H -tetrazole;
1 - (2,6 -dimethylphenyl)- IH -pyrazol-4 -yl]-2-< ^l-methylethyl) -2H -tetrazole;
1 - (2,6 -dimethylphenyl)- I H -pyrazol-4 -yl]- l-< 11 -methy lethyl)- -2H -tetrazole;
1 - (3,4 -dimethylphenyl)- I H -pyrazol-4 •yl]-2-( ^l -methy lethy 1) -2H -tetrazole;
1 - (3,4 -dimethylphenyl)- H -pyrazol-4 •ylj-l-l ^l -methylethyl) -2H -tetrazole;
1 - (3,5 ■dimethylphenyl)- I H -pyrazol-4 -yl]-2-( ' 1-methylethyl)- -2H -tetrazole;
1 - (3,5 -dimethylphenyl)- H -pyrazol-4 -yl]- l -< Ί -methylethyl) -2H -tetrazole;
1 -(2-ethylpheny 1)- 1 H-pyrazol-4-yl]-2-( 1 -methylethy l)-2H-tetrazole;
1 -(2-ethy lphenyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;
1 -(4-ethyIpheriy I)- 1 H-pyrazol-4-y l]-2-( 1 -methy lethy l)-2H-tetrazole;
l -(4-ethy lphenyl)- l H-pyrazol-4-yl]- l -(l -methy lethy l)-2H-tetrazole;
l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
1 -(4-methoxypheny I)- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethy l)-2H-tetrazole;
1 -methylethy l)-5-[ 1 -(2-methy lphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 -methylethy l)-5-[l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 -methylethyl)-5-[ 1 -(4-methy lphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
l -methylethyl)-5-[l -(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
5-chloro-l -methyl- l H-pyrazol-4-yl)-2-(l -methylethy l)-2H-tetrazole;
5-chloro- l -methyl- l H-pyrazol-4-yl)-l-(l -methylethyl)-2H-tetrazole;
5-chloro-l -ethyl- l H-pyrazol-4-yl)-2-(l -methylethyl)-2H-tetrazole;
5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)- 1 -( 1 -methylethyl)-2H-tetrazo!e;
5-chloro-l -(2-methylpropyl)-l H-pyrazoI-4-yl]-2-(l -methylethyl)-2H-tetrazole; 5-chloro- 1 -(2-methy Ipropyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methylethyl)-2H-tetrazole; l -benzyl-5-chloro-l H-pyrazol-4-yl)-2-(l -methy lethy l)-2H-tetrazole;
1 -benzy 1-5-chloro- 1 H-pyrazol-4-y 1)- 1 -( 1 -methy lethyl)-2H-tetrazole;
5-chloro-l -phenyl-l H-pyrazol-4-yl)-2-( l -methylethyl)-2H-tetrazole;
5-chloro- 1 -phenyl- 1 H-pyrazol-4-y 1)- 1-( 1 -methy lethyl)-2H-tetrazole;
5-chloro- 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methy lethy l)-2H-tetrazole;
156 -chloro 2- chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l)-2H-tetrazole; -chloro 3- chlorophenyl)- l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole; ■chloro 3- chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methylethy l)-2H-tetrazole; -chloro 4- chlorophenyl)- 1 H-pyrazol-4-yI]-2-( 1 -methylethyl)-2H-tetrazole; -chloro 4-chlorophenyl)-lH-pyrazol-4-yl]-l -( l -methy lethyl)-2H-tetrazole;
5- -chloro 2,3-dichlorophenyl )- l H-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole
5- -chloro 2.3- dichlorophenyl )- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethy l)-2H-tetrazole
5- -chloro- 2.4- dichlorophenyl )- l H-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole
5- -chloro 2.4- dichlorophenyl )-l H-pyrazoI-4-yl]- l -(l -methylethyl)-2H-tetrazole
5- -chloro- 2.5- dichlorophenyl )- 1 H-pyrazol-4-y l]-2-( 1 -methy lethy l)-2H-tetrazole
5- -chloro 2.5- dichlorophenyl )- 1 H-pyrazol-4-y 1]- 1 -( 1 -methylethy l)-2H-tetrazoIe
5- -chloro 2.6- dichlorophenyl )- l H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole
5- -chloro 2,6-dichlorophenyl )- l H-pyrazol-4-yl]-l -(l -methylethy l)-2H-tetrazole
5- -chloro 3,4-dichlorophenyl )-l H-pyrazol-4-yl]-2-( l -methylethy l)-2H-tetrazole
5- -chloro 3.4- dichlorophenyl )-l H-pyrazol-4-yl]- l -(l -methy lethy l)-2H-tetrazole
5- -chloro 3.5- dichlorophenyl )-l H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole
5- -chloro 3,5-dichlorophenyI )-l H-pyrazol-4-yl]- 1 -(1 -methy lethy l)-2H-tetrazole
5- -(2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-( l -methylethyl)-2H-tetrazole;
5- -(2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]- 1 -( 1 -methy lethy l)-2H-tetrazole;
5- -(3-bromophenyl)-5-chloro- l H-pyrazol-4-yl]-2-( l -methylethyl)-2H-tetrazole;
5- (3-bromophenyl)-5-chloro-l H-pyrazol-4-yI]- l -( l -methylethy l)-2H-tetrazole;
5-1 (4-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-( l -methylethyl)-2H-tetrazoIe;
5- (4-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-l -( l -methylethyl)-2H-tetrazole;
5 chloro- l -(4-fluorophenyl)- l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5- chloro- 1 -(4-fluorophenyl)- 1 H-pyrazol-4-yl]-l -( 1 -methylethyl)-2H-tetrazole;
5 chloro- 1 -(2-fluoropheny 1)- 1 H-pyrazol-4-y I]-2-( 1 -methy lethyl)-2H-tetrazole;
5-1 chloro- 1 -(2-fluoropheny I)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethyl)-2H-tetrazole;
5- chloro- 1 -(2, 3-dimethylpheny I)- l H-pyrazol-4-yl]-2-( l -methy lethy l)-2H-tetrazole;
5- chloro-1 -(2,3-dimethylphenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethyl)-2H-tetrazole;
5- chloro- 1 -(2, 4-dimethylphenyl)- l H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;
5- chloro- 1 -(2, 4-dimethylphenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l)-2H-tetrazole;
5- chloro- 1 -(2, -dimethyIpheny!)- l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5-1 chloro- 1 -(2,5-dimethy Iphenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l)-2H-tetrazole;
157 5- 5-chloro- l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2-( l -methy lethyl)-2H-tetrazole;
5- 5-chloro- l -(2,6-dimethyIphenyl)- lH-pyrazol-4-yl]-l -( l -methylethyl)-2H-tetrazole;
5- 5-chloro- l -(3,4-dimethylphenyl)-l H-pyrazol-4-yl]-2-( l -methylethyl)-2H-tetrazole;
5- 5-chloro- 1 -(3,4-dimethylpheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methylethy l)-2H-tetrazole;
5- 5-chloro- 1 -(3,5-dimethylphenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5- "5-chloro- 1 -(3,5-dimethylphenyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methylethy l)-2H-tetrazole;
5- 5-chloro- l -(2-ethylphenyl)-l H-pyrazoI-4-yl]-2-(l -methy lethyl)-2H-tetrazole;
5- 5-chloro- l -(2-ethylphenyl)-l H-pyrazol-4-yl]-l -( l -methylethy l)-2H-tetrazole;
5- 5-chloro- l -(4-ethylphenyl)-l H-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole; · 5- "5-chloro- l-(4-ethylphenyl)- l H-pyrazol-4-yl]- l -(l -methy lethyl)-2H-tetrazole;
5- 5-chloro- l -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5- 5-chloro- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;
5- 5-chloro- l -(2-methylphenyl)-l H-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole;
5- 5-chloro- 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethy l)-2H-tetrazole;
5- 5-chloro- 1 -(4-methylphenyl)- 1 H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;
5- 5-chloro- 1 -(4-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methy lethyl)-2H-tetrazole;
5- 5-bromo- 1 -methyl- 1 H-pyrazol-4-yl)-2-(l -methy lethy l)-2H-tetrazole;
5- (5-bromo- 1 -methyl- 1 H-pyrazol-4-y 1)- 1 -( 1 -methylethy l)-2H-tetrazole;
5- 5-bromo- 1 -ethyl- l H-pyrazol-4-yl)-2-( l -methylethyl)-2H-tetrazole;
5- (5-bromo- 1 -ethyl- 1 H-pyrazol-4-y 1)- 1 -( 1 -methy lethy l)-2H-tetrazole;
5- 5-bromo- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yI]-2-( 1 -methylethy l)-2H-tetrazole;
■ 5- 5-bromo- l -(2-methylpropyl)-l H-pyrazol-4-yl]- l-(l -methylethy l)-2H-tetrazole;
5- 1 -benzyl- 5-bromo-l H-pyrazol-4-yl)-2-(l -methylethy l)-2H-tetrazole;
5- 1 -benzyl- 5-bromo-l H-pyrazol-4-yl)- l -(l -methylethy l)-2H-tetrazole;
5- (5-bromo- 1 -phenyl- l H-pyrazol-4-yl)-2-(l -methylethy l)-2H-tetrazole;
5- (5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 -( 1 -methy lethy I)-2H-tetrazole;
5- 5-bromo- l -(2-chIorophenyl)- l H-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;
5- 5-bromo- 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -rhethylethyl)-2H-tetrazole;
5- 5-bromo- 1 -(3-chlorophenyl)- lH-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole;
5- 5-bromo- 1 -(3-chlorophenyl)- lH-pyrazol-4-yl]- 1 -( 1 -methylethyl)-2H-tetrazole;
5- 5-bromo- 1 -(4-chlorophenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5- 5-bromo- 1 -(4-chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethyl)-2H-tetrazole;
5- 5-bromo- 1 -(2,3-dichlorophenyl)-l H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
158 5- ^5-bromo- -(2,3-dichIorophenyl)- l H-pyrazol-4-yl]-l 1 -methylethyl)-2H-tetrazole
5- ^5-bromo- -(2,4-dichlorophenyl)-l H-pyrazol-4-yl]-2 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(2,4-dichlorophenyl)-l H-pyrazol-4-yl]-l 1 -methylethyl)-2H-tetrazole
5- "5-bromo- -(2,5-dichlorophenyl)- 1 H-pyrazol-4-y l]-2 1 -methy lethyl)-2H-tetrazole
5- "5-bromo- -(2,5-dichlorophenyl)- l H-pyrazol-4-yl]-l 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(2,6-dichlorophenyl)-l H-pyrazol-4-yl]-2 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(2,6-dichlorophenyl)-l H-pyrazoI-4-yl]- l 1 -methy lethyl)-2H-tetrazole
5- 5-bromo- -(3,4-dichlorophenyl)- l H-pyrazol-4-yl]-2 1 -methy lethy l)-2H-tetrazole;
5- 5-bromo- -(3,4-dichlorophenyl)- l H-pyrazol-4-yI]-l 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(3,5rdichlorophenyl)-l H-pyrazol-4-yl]-2 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(3,5-dichlorophenyl)- 1 H-pyrazol-4-y 1]- 1■ 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(2-bromophenyl)-l H-pyrazol-4-yl]-2-( l -methy lethyl)-2H-tetrazole;
5- 5-bromo- -(2-bromopheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;
5- 5-bromo- -(3-bromophenyl)-l H-pyrazol-4-yl]-2-( l -methy lethyl)-2H-tetrazole;
5- 5-bromd- -(3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethyl)-2H-tetrazole;
5- 5-bromo- -(4-bromophenyl)-l H-pyrazol-4-yl]-2-( l -methy lethy l)-2H-tetrazole;
5- 5-bromo- -(4-bromopheny 1)- l H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;
5- 5-bromo- -(4-fluorophenyl)-l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5- 5-bromo- -(4-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l)-2H-tetrazole;
5- 5-bromo- -(2-fluorophenyl)- l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5- 5-bromo- -(2-fluorophenyl)-l H-pyrazol-4-yl]- l-( l -methy lethy l)-2H-tetfaz01e;
5- 5-bromo- -(2,3-dimethylphenyl)-lH-pyrazol-4-yl 1 -methylethy l)-2H-tetrazoie
5- 5-bromo- -(2,3-dimethylphenyl)-lH-pyrazol-4-yl l -methylethyl)-2H-tetrazole
5- 5-bromo- -(2,4-dimethylphenyl)- 1 H-pyrazol-4-yl 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(2,4-dimethylphenyl)-l H-pyrazol-4-yl 1 -methy lethy l)-2H-tetrazole
5- 5-bromo- -(2,5-dimethylphenyl)-l H-pyrazol-4-yl 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(2,5-dimethylphenyl)- l H-pyrazol-4-yl I -methylethyl)-2H-tetrazole
5- 5-bromo- -(2,6-dimethy lphenyl)- 1 H-pyrazol-4-y Γ 1 -methy lethyl)-2H-tetrazole
5- 5-bromo- -(2,6-dimethylphenyl)-l H-pyrazol-4-yl 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(3,4-dimethylphenyl)-l H-pyrazol-4-yr 1 -methylethyl)-2H-tetrazole
5- 5-bromo- -(3,4-dimethylphenyl)-lH-pyrazol-4-yl 1 -methylethyl)-2H-tetrazoIe
5- 5-bromo- -(3,5-dimethylphenyl)-l H-pyrazol-4-yr 1 -methy lethy l)-2H-tetrazole
5- "5-bromo- -(3, 5-dimethy lphenyl)- 1 H-pyrazoI-4-y 1 1 -methy!ethyl)-2H-tetrazole
159 5- 5-bromo- 2-ethylphenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methy lethy l)-2H-tetrazole;
5- 5-bromo- 2-ethy Iphenyl)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole; .
5- 5-bromo- 4-ethylphenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methy lethy!)-2H-tetrazole;
5- 5-bromo- 4-ethylphenyl)- 1 H-pyrazol-4-yl]-l -(1 -methylethyl)-2H-tetrazole;
5- 5-bromo- 4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;
5- 5-bromo- 4-methoxypheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;
5- 5-bromo- 2-methy Iphenyl)- lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole;
5- 5-bromo- 2-methylphenyl)-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole;
5- 5-bromo- 4-methylphenyl)-l H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole;
5- 5-bromo- 4-methylphenyl)-lH-pyrazol-4-yl]-l-(l -methy lethyl)-2H-tetrazole; 5-(5-iodo- 1 -methyl- 1 H-pyrazoI-4-yl)-2-( 1 -methylethyl)-2H-tetrazole;
•5-(5-iodo-l -methyl- lH-pyrazol-4-yl)-l-(l-methylethyl)-2H-tetrazole;
5-(l-ethyl-5-iodo-lH-pyrazol-4-yl)-2-(l-methylethyl)-2H-tetrazole;
5-( 1 -ethyl-5-iodo- 1 H^pyrazol-4-yl)- 1 -( 1 -methylethyl)-2H-tetrazole;
5-[5-iodo- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2-( 1 -methy lethy l)-2H-tetrazo!e; 5-[5-iodo-l-(2-methylpropyl)-lH-pyrazol-4-yI]-l-(l-methylethyl)-2H-tetrazole; 5-(l-benzyl-5-iodo-lH-pyrazol-4-yl)-2-(l -methy lethy l)-2H-tetrazole;
5-(l-benzyl-5-iodo-lH-pyrazol-4-yl)-l-(l -methy lethy l)-2H-tetrazole;
5-(5-iodo- 1 -phenyl- 1 H-pyrazol-4-y l)-2-( 1 -methy lethy l)-2H-tetrazole;
5-(5-iodo- 1 -phenyl- 1 H-pyrazol-4-y 1)- 1 -( 1 -methy lethy l)-2H-tetrazole;
5-[ 1 -(2-chloropheny l)-5-iodo- 1 H-pyrazol-4-yl]-2-( 1 -methylethyl)-2H-tetrazole; 5-[l.-(2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole; 5-[l-(3-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methy lethy l)-2H-tetrazole; 5-[l-(3-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l -methy lethyl)-2H-tetrazole; 5-[l-(4-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole; 5-[ 1 -(4-chlorophenyl)-5-iodo-l H-pyrazoI-4-yl]- 1 -(] -methy lethy l)-2H-tetrazole; 5-[l-(2,3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole; 5-[l -(2, 3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l -methy lethy l)-2H-tetrazole; 5-[l-(2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole; 5-[l-(2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l -methy lethyl)-2H-tetrazole; 5-[l-(2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l -methy lethyl)-2H-tetrazole; 5-[l-(2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l-(l-methylethyl)-2H-tetrazole; 5-[l-(2,6-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(l-methylethyl)-2H-tetrazole;
160 2,6-dichloropheny l)-5-iodo- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethy l)-2H-tetrazole;
3.4- dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2-( 1 -methy lethyl)-2H-tetrazole; 2,6-dichloropheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole;
5- 3.5- dichlorophenyl)-5-iodo- lH-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5- 3,5-dichlorophenyl)-5-iodo- l H-pyrazol-4-yl]-l -(l -methylethyl)-2H-tetrazole;
5- 2-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2-(l -methylethyl)-2H-tetrazole;
5- 2- bromophenyl)-5-iodo-lH-pyrazol-4-yl]- l-( l -methylethy l)-2H-tetrazole;
5- 3- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2-( l -methy lethy l)-2H-tetrazole;
5- 3- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-l -( 1 -methylethyl)-2H-tetrazole;
5- 4- bromophenyl)-5-iodo- lH-pyrazol-4-yl]-2-( I -methylethy l)-2H-tetrazole;
5- 4-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-l -(l -methylethyl)-2H-tetrazole;
5- 4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2-( l -methyIethyl)-2H-tetrazole;
5-1 4-fluorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -( 1 -methylethyl)-2H-tetrazole;
5- 2-fluorophenyl)-5-iodo- l H-pyrazol-4-yl]-2-( l -methylethyl)-2H-tetrazole;
5- 2-fluorophenyl)-5-iodo- l H-pyrazol-4-yl]-l -( l -methylethyl)-2H-tetrazole;
5- 2,3-dimethylphenyl)-5- odo- 1 H-pyrazol-4-y 1 ( 1 -methylethy l)-2H-tetrazole
5· 2.3- dimethylphenyl)-5- odo-l H-pyrazol-4-yl (1 -methy lethyl)-2H-tetrazole
5- 2.4- dimethylphenyl)-5- odo- 1 H-pyrazol-4-y 1 ( 1 -methylethyl)-2H-tetrazole
■5- 2.4- dimethylphenyl)-5- odo- 1 H-pyrazol-4-y 1 (1 -methylethy l)-2H-tetrazole
5- 2.5- dimethylphenyl)-5- odo-lH-pyrazol-4-yl]-2 (1 -methy lethy l)-2H-tetrazole
5- 2.5- dimethylphenyl)-5- odo-l H-pyrazol-4-yll-l ( 1 -methylethyl)-2H-tetrazole
5- 2.6- dimethylphenyl)-5- odo- 1 H-pyrazo!-4-yIl-2-( ( 1 -methylethyl)-2H-tetrazole
5- 2,6-dimethylphenyl)-5- odo-1 H-pyrazol-4-yl ( 1 -methylethyl)-2H-tetrazole
5-[ 3,4-dimethylpheny!)-5- odo- 1 H-pyrazol-4-y Π-2-ι (1 -methy lethyl)-2H-tetrazole
5-[ 3.4- dimethylphenyl)-5- odo- 1 H-pyrazol-4-y 1 ( 1 -methy lethy l)-2H-tetrazole
5- 3.5- dimethylphenyl)-5- odo- l H-pyrazol-4-y Π-2- ( 1 -methylethyl)-2H-tetrazole
5- 3,5-dimethylphenyl)-5- odo-l H-pyrazol-4-ylJ- l ( 1 -methylethyl)-2H-tetrazole
5- 2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2-(l -me thy lethy l)-2H-tetrazole;
5- 2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-l -( l -me thy lethy l)-2H-tetrazole;
5- 4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2-(l -me thylethyl)-2H-tetrazole;
5- 4-ethyIphenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 -(1 -me thylethyl)-2H-tetrazole;
5- iodo- 1 -(4-methoxypheny 1)- 1 H-pyrazol-4-y l]-2-( 1 methylethy l)-2H-tetrazole;
5- iodo- 1 -(4-methoxypheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 methy lethy l)-2H-tetrazole;
161 5-[5-iodo- l (2-methy Iphenyl)- l H-pyrazol-4-yl]-2-( l -methy lethy l)-2H-tetrazole; 5-[5-iodo- l (2-methylphenyI)- 1 H-pyrazoI-4-yl]- 1 -( 1 -methy lethyl)-2H-tetrazole; 5-[5-iodo- l (4-methy Iphenyl)- 1 H-pyrazol-4-yl]-2-( 1 -methy lethy l)-2H-tetrazole; 5-[5-iodo-l (4-methy Ipheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 1 -methy lethy l)-2H-tetrazole; 2-benzyl-5- 1 -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5- 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5- 1 -ethyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5- 1 -ethyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
2- benzyl-5- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- l -(2-methylpropyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 1 -benzyl- l H-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5- 1 -benzyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5- 1 -phenyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
1 - benzyl-5- 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5- 2-chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 -benzyl-5- 2- chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- 3- chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 3- chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- l -(4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 4- chloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 2,3-dichlorophenyl H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 2.3- dichlorophenyl H-pyrazol-4-y 1 ]-2H-tetrazole
2- benzyl-5- 2.4- dichlorophenyl H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 2.4- dichlorophenyl H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- 2.5- dichlorophenyl H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 2.5- dichlorophenyl H-py razo 1 -4-y 1] -2 H-tetrazo le
2- benzyl-5- 2.6- dichlorophenyl H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 2,6-dichlorophenyl H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- 3,4-dichlorophenyl H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 3,4-dichlorophenyl H-pyrazol-4-yl]-2H-tetrazole
2- benzyl— [ -(3,5-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- l-(3,5-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- l-(2-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
162 1- benzyl-5- 1 -(2-bromophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- benzyl-5- 1 -(3-bromophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 2-benzyl-5- 1 -(4-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- l-(4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 1 -(4-fluoropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1- benzyl-5- l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 1- (2,3 -dimethylphenyl)- 1H -pyrazol-4-yl]-2H-tetrazole
1- benzyl-5- 1- (2,3 -dimethylphenyl)- IH -pyrazol -4-yl]-2H-tetrazole
2- benzyl-5- 1- (2,4 -dimethylphenyl)- 1H -pyrazol -4-yl]-2H-tetrazole
1- benzyl-5- 1- (2,4 -dimethylphenyl)- IH -pyrazol -4-yl]-2H-tetrazole
2- benzyl-5- 1- (2,5 -dimethylphenyl)- IH -pyrazol -4-yl]-2H-tetrazole
1- benzyl-5- 1- (2,5 -dimethylphenyl)- IH -pyrazol -4-yl]-2H-tetrazole
2- benzyl-5- 1- (2,6 -dimethylphenyl)- IH -pyrazol -4-yl]-2H-tetrazole
1- benzyl-5- 1- (2,6 -dimethylphenyl)- IH -pyrazol- -4-yl]-2H-tetrazole
2- benzyl-5- 1- (3,4 -dimethylphenyl)- IH -pyrazol- -4-yl]-2H-tetrazole
1- benzyl-5- 1- (3,4 -dimethylphenyl)- IH -pyrazol- -4-yl]-2H-tetrazole
2- benzyl-5- 1- (3,5 -dimethylphenyl)- IH -pyrazol- -4-yl]-2H-tetrazole
1- benzyl-5- 1- (3,5 -dimethylphenyl)- IH -pyrazol- -4-yl]-2H-tetrazole
2- benzyl-5- 1- 2-ethylphen.yl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- 2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- l-(4-ethylphenyl)-lH-pyrazol-4-yI]-2H-tetrazole;
1- benzyl-5- l-(4-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5-11 -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-i 1 -(2-methylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1- benzy 1-5 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 1 -(4-methylphenyl)- 1 H-pyrazoI-4-yl]-2H-tetrazole;
1- benzyl-5- 1-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-i 5-chloro-l -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
1- benzy 1-5- 5-chloro-l-methyl-lH-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5-' 5-chloro- 1 -ethyl- lH-pyrazol-4-yl)-2H-tetrazole;
163 1 - benzyl-5 5-chloro-l -ethyl- l H-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5 5-chloro-l-(2-methylprppyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5 5-chloro-l -(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5 l-benzyl-5-chloro-l H-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5 l -benzyl-5-chloro-lH-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5 5-chloro- phenyl-lH-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5 5-ehIoro- phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5- 5-chloro- 2-chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 1 -benzyl-5- 5-chloro- 2- chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 2-benzyl-5- 5-chloro- 3- chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 5-chloro- 3- chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-chloro- 4- chlorophenyl)- l H-pyrazol-4-yI]-2H-tetrazole;
1 - benzyl-5- 5-chloro- 4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-chloro- 2,3-dichlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 - benzyl-5- 5-chloro- 2.3- dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-chloro- 2.4- dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 5-chloro- 2.4- dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyI-5- 5-chloro- 2.5- dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 5-chloro- 2,5-dichlofophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-chloro- 2,6 -dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 5-chloro- 2,6 -dichlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- benzyl-5- 5-chloro- 3,4-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 5-chloro- 3.4- dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-chloro- 3.5- dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazoIe;
1 - benzyl-5- 5-chloro- 3,5-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- l -(2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 1 -(2-bromophenyl)-5-chloro- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 1 -(3-bromophenyl)-5-chloro- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- l-(3-bromophenyl)-5-chloro- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- l -(4-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 1 -(4-bromophenyl)-5-chloro- 1 H-pyrazoI-4-y l]-2H-tetrazole;
2- benzyl-5- 5-chloro-l -(4-fluorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole; l -benzyl-5- 5-chloro-l -(4-fluorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
164 2-benzyl-5- [5-chloro- l -(2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; l -benzyl-5- [5-chloro- l -(2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- [5-chloro- l -(2,3-dimethylphenyl)-l H-pyrazo!-4-yl]-2H-tetrazole; l -benzyl-5- [5-chloro- l -(2,3-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- [5-chloro- 1 -(2,4-dimethylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole; l -benzyl-5- [5-chloro- 1 -(2,4-dimethylphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2-benzyl-5- [5-chloro- 1 -(2,5-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; l -benzyl-5- 5-chloro- l -(2,5-dimethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- 5-chloro- 1 -(2,6-dimethy lphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole; l -benzyl-5- 5-chloro- l -(2,6-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- 5-chloro- l -(3,4-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; l -benzyl-5- 5-chloro- l -(3,4-dimethy lphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- 5-chloro- l -(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole; l -benzyl-5- 5-chloro- l -(3,5-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- 5-chloro- l -(2-ethy lphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; l -benzyl-5- 5-chloro- 1 -(2-ethy lphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- "5-chloro- l -(4-ethylphenyl)- l H-pVrazol-4-yl]-2H-tetrazole; l -benzyl-5- 5-chloro- l -(4-ethylphenyl)- l H-pyrazol-4-yl |-2H-tetrazole;
2-benzyl-5- 5-chloro- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole; l -benzyl-5- 5 chloro- l -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- "5-chloro- l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; l -benzyl-5- 5-chloro- l -(2-methy lphenyl)- lH-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- 5-chloro- l -(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole; l -benzyl-5- 5-chloro- l -(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole; .
2-benzyl-5- (5-bromo- 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
l -benzyl-5- 5-bromo- 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2-benzyl-5- (5-bromo- 1 -ethyl- l H-pyrazol-4-yl)-2H-tetrazole;
l -benzyl-5- 5-bromo- 1 -ethyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2-benzyl-5- 5-bromo- 1 -(2-methy lpropyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 -benzy 1-5- 5-bromo- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2-benzyl-5- ( 1 -benzy 1- 5-bromo-l H-pyrazol-4-yl)-2H-tetrazole;
1 -benzy 1-5- ( 1 -benzy 1- 5-bromo- l H-pyrazol-4-yl)-2H-tetrazole;
2-benzyl-5- (5-bromo- 1 -phenyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
165 1 - benzy I-5-I 5-bromo- phenyl- 1 H-pyrazoI-4-y l)-2H-tetrazole;
2- benzyl-5-| 5-bromo- 2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- 2- chlorophenyl)- lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-| 5-bromo- 3- chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- 3- chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-| 5-bromo- 4- chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-| 5-bromo- 4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-| 5-bromo- 2,3-dichlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole
1 - benzyl-5-| 5-bromo- 2.3- dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5-| 5-bromo- 2.4- dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole 1 -benzyl-5-| 5-bromo- 2.4- dichlorophenyl) H -py razo 1-4-y 1] -2 H -tetrazo le 2-benzyl-5-| 5-bromo- 2.5- dichlorophenyl) H-pyrazol-4-yI]-2H-tetrazole
1 - benzyl-5-| 5-bromo- 2.5- dichlorophenyl) H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5-| 5-bromo- 2.6- dichlorophenyl) H-pyrazol-4-yl]-2H-tetrazole
1- benzy 1-5-15-bromo- 2,6-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5-[ 5-bromo- 3,4-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole
1 - benzy I-5-[ 5-bromo- 3.4- dichlorophenyl)-l H-pyrazol-4-yI]-2H-tetrazole
2- benzyl-5-[ 5-bromo- 3.5- dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5-[ 5-bromo- 3,5-dichlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5-| 5-bromo- 2-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5-[ 5-bromo- 2- bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-| 5-bromo- 3- bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzy l-5-[ 5-bromo- 3- bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-( 5-bromo- 4- bromopheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 - benzy l-5-[ 5-bromo- 4-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-[ 5-bromo- 4-fluorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-[ 5-bromo- 4-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-[ 5-bromo- 2-fluoropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 - benzyl-5-[ 5-bromo- 2-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-[ 5-bromo- 2,3-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-[ 5-bromo- 2.3- dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-[ 5-bromo- 2.4- dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; l -benzyI-5-[ 5-bromo- 2,4-dichIorophenyI)- l H-pyrazoI-4-yl]-2H-tetrazole;
166 2-benzyl-5- 5-bromo- 2,5-dichlorophenyl)- H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 5-bromo- 2.5- dichlorophenyl)- H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- 5-bromo- 2.6- dichlorophenyl)- H-py razo 1-4-y l]-2H-tetrazo le
1 - benzyl-5- 5-bromo- 2,6-dichlorophenyl)- H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- 5-bromo- l -i 3,4-dichlorophenyl)- H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 5-bromo- l - 3.4- dichlorophenyl)- H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- 5-bromo-l - 3.5- dichlorophenyl)- H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 5-bromo- l- 3,5-dichlorophenyl)- H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- 5-bromo-l - 2-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 5-bromo- 2-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-bromo- 4-ethylphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 - benzyl-5- 5-bromo- 4-ethy lpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- benzyl-5- 5-bromo- 4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 5-bromo- 4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-bromo- 2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- 5-bromo- 2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-bromo- 4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 5-bromo- 4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 5-iodo-l -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5- 5-iodo-l -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5- l -ethyl-5-iodo-lH-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5- 1 -ethy 1-5-iodo- 1 H-pyrazol-4-y l)-2H-tetrazole;
2- benzyl-5- 5-iodo-l -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- 5-iodo-l -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 1 -benzyl-5-iodo- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 - benzyl-5- 1 -benzyl-5-iodo- 1 H-pyrazol-4-y l)-2H-tetrazole;
2- benzyl-5-' 5-iodo-l -phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
1- benzyl-5 5-iodo-l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
2- benzyl-5 l -(2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5 l -(2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5 1 -(3-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5 1 -(3-chloropheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- benzyl-5 1 -(4-chIoropheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
167 1 - benzyl-5- -(4-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- 1 -(2,3-dichloropheny l)-5- odo- l H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 1 -(2,3-dichloropheny l)-S- odo- lH-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- l-(2,4-dichlorophenyl)-5 odo-lH-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 1 -(2,4-dichlorophenyl)-5 odo- 1 H-pyrazol-4-y l]-2H-tetrazole
2- benzyl-5- l-(2,5-dichlorophenyl)-5 odo- 1 H-pyrazol-4-y l]-2H-tetrazole
1 - benzyl-5- l-(2,5-dichlorophenyl)-5 odo-l H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- 1 -(2,6-dichlorophenyl)-5 odo- l H-pyrazol-4-yl]-2H-tetrazoie
1 - benzyl-5- 1 -(2,6-dichlorophenyl)-5 odo-l H-pyrazol-4-yi]-2H-tetrazole
2- benzyl-5- 1 -(3,4-dichlorophenyl)-5 odo-l H-pyrazol-4-yl]-2H-tetrazole
1 - benzyl-5- 1 -(3,4-dichlorophenyl)-5 odo-l H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- 1 -(3,5-dichlorophenyl)-5 odo- 1 H-pyrazol-4-y l]-2H-tetrazole
1 - benzyl-5- 1 -(3,5-dichlorophenyl)-5 odo-l H-pyrazol-4-yl]-2H-tetrazole
2- benzyl-5- -(2-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- -(2-bromophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- benzyl-5- -(3-bromophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- -(3-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- -(4-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- -(4-bromophenyl)-5-iodo-l H-pyrazol-4-yI]-2H-tetrazole;
2- benzyl-5- -(4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1- benzyl-5- -(4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5- -(2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5- -(2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-' -(2,3-dimethylphenyl)-5- odo- 1 H -pyrazo -4 -yl]-2H -tetrazole
1 - benzyl-5- -(2,3-dimethylphenyl)-5- odo- 1 H ■pyrazo -4 -yl]-2H -tetrazole
2- benzyl-5- -(2,4-dimethylphenyl)-5- odo- ΪΗ -pyrazo -4 -yl]-2H -tetrazole
1 - benzyl-5- -(2,4-dimethylphenyl)-5- odo- 1 H ■pyrazo -4 -yl]-2H -tetrazole
2- benzyl-5- -(2,5-dimethylphenyl)-5- odo- 1 H -pyrazo -4 -yl]-2H -tetrazole
1 - benzyl-5-| -(2,5-dimethylphenyl)-5- odo- 1 H- -pyrazo -4 -yl]-2H -tetrazole
2- benzyl-5-| -(2,6-dimethylphenyl)-5- odo- 1 H -pyrazo -4 -yl]-2H -tetrazole
1- benzyl-5- -(2,6-dimethylphenyl)-5- odo- 1 H- -pyrazol -4 -yl]-2H- -tetrazole
2- benzyl-5- -(3,4-dimethylphenyl)-5- odo- 1 H- -pyrazol -4 -yl]-2H- -tetrazole l -benzyl-5- -(3,4-dimethylphenyl)-5- odo- 1 H- -pyrazoi -4 -yl]-2H -tetrazole
168 2-benzyl-5-[l -(3,5-dimethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-[l -(3,5-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-[l -(2-ethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-[l -(2-ethy]phenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- benzyl-5-[l -(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1 -benzyl-5-[ 1 -(4-ethy lpheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
2-benzyl-5-[5-iodo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-[5-iodo-l -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- benzy l-5-[5-iodo- 1 -(2-methylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole; 1 -benzyl-5-[5-iodo- 1 -(2-methy lphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole; 2-benzyl-5-[5-iodo-l -(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 - benzyl-5-[5-iodo-l -(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5-( 1 -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
1 - (4-bromobenzy l)-5-(l -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
2- (4-bromobenzyl)-5-( l-ethyl-lH-pyrazol-4-yl)-2H-tetrazole;
1 -(4-bromobenzy l)-5-( 1 -ethyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2-(4-bromobenzyl)-5-[l -(2-methy lpropyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[ l -(2-methy lpropyl)-lH-pyrazol-4'-yl]-2H-tetrazoIe; 5-(l -benzyl- l H-pyrazol-4-yl)-2-(4-bromobenzyl)-2H-tetrazole;
5-( 1 -benzyl- 1 H-pyrazol-4-yl)- 1 -(4-bromobenzyl)-2H-tetrazole;
2- (4-bromobenzyl)-5-( 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 - (4-bromobenzy l)-5-(l -phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
2- (4-bromobenzyl)-5-[ l -(2-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5-[ 1 -(2-chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 2-(4-bromobenzyl)-5-[l -(3-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[l -(3-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5-[l -(4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazoIe;
1 - (4-bromobenzy l)-5-[l -(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5-[l -(2,3-dichlorophenyl)-l H-pyrazol-3-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5-[l -(2,3-dichlorophenyl)- l H-pyrazol-3-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5-[l -(2,4-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - (4-bromobenzyl)-5-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5-[l -(2,5-dichlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
169 1- (4-bromobenzyl) -5- [i- (2,5-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyr -5- [·- (2,6-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyi -5- [i- (2,6-dichloropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- (4-bromobenzyr -5- [i- (3,4-dichloropheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzy -5- [i- (3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyr -5- [i- (3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl) -5- [i- (3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyr -5- [i- (2-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1
Figure imgf000164_0001
i- (2-bromophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- '4-bromobenzyr -5- [i- (3-bromophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1- ^4-bromobenzyr -5- [i- (3-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
Figure imgf000164_0002
1- (4-bromobenzyl) -5- [i- (4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- '4-bromobenzyl) -5- [i- (4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
Figure imgf000164_0003
Figure imgf000164_0004
i- (2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 1 H-pyrazol-4-y l]-2H-tetrazole;
Figure imgf000164_0005
2- ^4-bromobenzyr -5- [i- (2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- '4-bromobenzyl) -5- [i- (2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
Figure imgf000164_0006
H-pyrazol-4-yl]-2H-tetrazole;
Figure imgf000164_0007
2- ^4-bromobenzyl -5- ;i- ■2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- ^4-bromobenzyl -5- ;i- ^2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl) -5- ;i- ,6-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1- ^4-bromobenzyl) -5- ,6-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- ^4-bromobenzyl' -5- 1- ;3,4-dimethylphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1- ^4-bromobenzyl' -5- 1- (3,4-dimethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- ^4-bromobenzyl^ -5- 1- ;3,5-dimethylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1- ^4-bromobenzyl -5- 1- ^3,5÷dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
2- ^4-bromobenzyl^ -5- ;i- ;2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- ^4-bromobenzyl^ -5- 1- (2-ethylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- ^4-bromobenzyl -5- 1- ^4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1- ^4-bromobenzyl^ -5- 1- ^4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
170 2-(4-bromobenzyl)-5- l -(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
1 -(4-bromobenzyl)-5- 1 -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2-(4-bromobenzy l)-5- l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 -(4-bromobenzyl)-5- l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2-(4-bromobenzy l)-5 - l -(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1- (4-bromobenzyl)-5- l -(4-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5- 5-chloro- 1 -methyl- l H-pyrazol-4-yl)-2H-tetrazo!e;
1 -(4-bromobenzy l)-5- 5-chloro-l -methyl-l H-pyrazol-4-yl)-2H-tetrazole;
2-(4-bromobenzyl)-5- 5-chloro- 1 -ethyl- l H-pyrazol-4-yl)-2H-tetrazole;
1 -(4-bromobenzy l)-5- 5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
2-(4-bromobenzyl)-5- 5-chloro- 1 -(2-methylpropyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 - (4-bromobenzyl)-5- 5-chloro- l -(2-methylpropyl)- l H-pyrazol-4-yl]-2H-tetrazo.le; 5-(l -benzyl-5-chloro- H-pyrazol-4-yl)-2-(4-bromobenzyl)-2H-tetrazole;
5-(l -benzyl-5-chloro- H-pyrazol-4-yl)-l -(4-bromobenzyl)-2H-tetrazole;
2- (4-bromobenzyl)-5- 5-chloro- l-phenyl-l H-pyrazol-4-yl)-2H-tetrazole;
1 -(4-bromobenzyl)-5- 5-chloro- 1 -phenyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
2-(4-bromobenzyl)-5- 5-chloro- l -(2-chlorophenyl)- l H-pyraz01-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5- 5-chloro- l -(2-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 2-(4-bromobenzyl)-5- 5-chloro- l -(3-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5- 5-chloro- l-(3-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 2-(4-bromobenzyl)-5- 5-chloro- l-(4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; I -(4-bromobenzyl)-5- 5-chloro- l -(4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 2-(4-bromobenzyl)-5- 5-chloro- 1 -(2, 3-dichlorophenyl l H-pyrazol-4-yl -2H-tetrazole; 1 -(4-bromobenzy l)-5- 5-chloro-l -(2,3-dichlorophenyl l H-pyrazol-4-yl -2H-tetrazole; 2-(4-bromobenzyl)-5- 5-chloro- 1 -(2, 4-dichlorophenyl l H-pyrazol-4-yl -2H-tetrazole; 1 -(4-bromobenzy l)-5- 5-chloro- 1 -(2, 4-dichlorophenyl l H-pyrazol-4-yl -2H-tetrazole; 2-(4-bromobenzyl)-5- 5-chloro- l-(2,5-dichlorophenyl l H-pyrazol-4-yl -2H-tetrazole; 1 -(4-bromobenzy l)-5- 5-chloro- 1 -(2,5-dichlorophenyl 1 H-pyrazol-4-yl -2H-tetrazole; 2-(4-bromobenzy l)-5 - 5-chloro-l -(2, 6-dichlorophenyl 1 H-pyrazol-4-yl -2H-tetrazole; 1 -(4-bromobenzyl)-5- 5-chloro- l -(2,6-dichlorophenyl l H-pyrazol-4-yl -2H-tetrazole; 2-(4-bromobenzyl)-5- 5-chloro- l -(3,4-dichlorophenyl l H-pyrazol-4-yl -2H-tetrazole; 1 -(4-bromobenzyl)-5 5-chloro- 1 -(3, 4-dichlorophenyl 1 H-pyrazol-4-yl •2H-tetrazole; 2-(4-bromobenzyl)-5 5-chloro-l -(3, 5-dichlorophenyl l H-pyrazol-4-yl •2H-tetrazole;
171 1 -(4-bromobenzyl)-5- 5-chloro- l -(3,5-dichlorophenyl)-l H-pyrazoI-4-yI]-2H-tetrazole; -(4-bromobenzyl)-5- 1 -(2-bromopheny l)-5-chloro- 1 H-pyrazol-4-y l]-2H-tetrazole; 1 -(4-bromobenzy l)-5- l -(2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5- 1 -(3-bromopheny l)-5-chloro- 1 H-pyrazol-4-yl]-2H-tetrazole; l -(4-:bromobenzyl)-5- 1 -(3-bromophenyl)-5-chloro- 1 H-pyrazol-4-y l]-2H-tetrazole; -(4-bromobenzyl)-5- 1 -(4-brdmophenyl)-5-chloro- 1 H-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5- 1 -(4-bromophenyl)-5-chloro- 1 H-pyrazol-4-y l]-2H-tetrazole; -(4-bromobenzyl)-5- 5-chloro- 4-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5- 5-chloro- 4-fluorophenyl)-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5-' 5-chloro- 2-fluorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzy l)-5 5-chloro- 2-fluoropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole; -(4-bromobenzyl)-5 5-chloro- 2,3-dimethylphenyl)- H-pyrazol -4 -yl] -2H -tetrazole 1 -(4-bromobenzy l)-5 5-chloro- 2.3- dimethylphenyl)- H-pyrazol -4 -yl] -2H -tetrazole -(4-bromobenzyl)-5 5-chloro- 2.4- dimethylphenyl)- H-pyrazol -4 ■yi] -2H -tetrazole 1 -(4-bromobenzyl)-5 5-chloro- 2.4- dimethylphenyl)- H-pyrazol -4 -yl] -2H -tetrazole -(4-bromobenzyl)-5 5-chloro- 2.5- dimethylphenyl)- H-pyrazol -4 -yl] -2H -tetrazole 1 -(4-bromobenzy l)-5 5-chloro- 2.5- dimethylphenyl)- H-pyrazol -4 -yl] -2H -tetrazole -(4-bromobenzyl)-5 5-chloro- 2.6- dimethylphenyl)- H-pyrazol -4 -yl] -2H -tetrazole 1 -(4-bromobenzyl)-5 5-chIoro- 2,6-dimethylphenyl)- H-pyrazol -4 ■yi] -2H -tetrazole -(4-bromobenzyl)-5 5-chloro- 3,4-dimethylphenyl)- H-pyrazol -4 -yl] -2H -tetrazole 1 -(4-bromobenzyl)-5 5-chloro- 3.4- dimethyIphenyl)- H-pyrazol -4 ■yi] -2H -tetrazole -(4-bromobenzyl)-5 5-chloro- 3.5- dimethylphenyl)- H-pyrazol -4 -yl] -2H -tetrazole 1 -(4-bromobenzyl)-5 5-chloro- 3,5-dimethylphenyl)- H-pyrazol-4-yl]-2H-tetrazole -(4-bromobenzyl)-5 5-chloro- 2-ethylpheny 1)- 1 H-pyrazoI-4-y l]-2H-tetrazole; 1 -(4-bromobenzyl)-5 5-chloro- 2-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5 5-chloro- 4-ethylphenyI)- l H-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5 5-chloro- 4-ethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5 5-chloro- 4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5 5-chloro- 4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5 5-chloro- 2-methylphenyl)-] H-pyrazol-4-yl]-2H-tetrazoie; 1 -(4-bromobenzyl)-5 5-chloro- 2-methy lpheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazole; -(4-bromobenzyl)-5 5-chloro- 4-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole; 1 -(4-bromobenzyl)-5 5-chloro- 4-methylpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
172 2- (4-bromobenzyl)-5- ^5-bromo- -methy 1- 1 H-pyrazol-4-y l)-2 H-tetrazole;
1 - (4-bromobenzyl)-5- ^5-bromo- -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
2- (4-bromobenzyl)-5- (5-bromo- -ethyl- 1 H-pyrazol-4-y l)-2 H-tetrazole;
1 - (4-bromobenzyl)-5- (5-bromo- -ethyl- l H-pyrazol-4-yl)-2H-tetrazoIe;
2- (4-bromobenzyl)-5- 5-bromo- -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - ^4-bromobenzyl)-5- 5-bromo- -(2-methyipropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
5- ' 1 -benzyl-5-bromo- 1 H-pyrazo■4-yl)-2-(4-bromobenzyl)-2H-tetrazole;
5- -benzyl-5-bromo- 1 H-pyrazo■4-yl)-l -(4-bromobenzyl)-2H-tetrazole;
2- (4-bromobenzyl)-5- (5-bromo- -phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
1 - (4-bromobenzyl)-5- (5-bromo- -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
' 2- (4-bromobenzyi)-5- 5-bromo- -(2-chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - ^4-bromobenzyl)-5- 5-bromo- -(2-chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- ^4-bromobenzyl)-5- 5-bromo- -(3-chlorophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 - (4-bromobenzyl)-5- 5-bromo- l -(3-chlorophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- ^4-bromobenzyl)-5- 5-bromo-l -(4-chloropheny 1)- 1 H-pyrazol-4-y l -2H-tetrazole;
1 - '4-bromobenzyl)-5- 5-bromo-l -(4-chloropheny 1)- 1 H-pyrazol-4-y l]-2 H-tetrazole;
2- -bromobenzyl)-5- 5-bromo- (2,3 -dichlorophenyl)- H -pyrazol-4-yl -2H-tetrazole;
1 - 4-bromobenzyl)-5- 5-bromo- (2,3 -dichlorophenyl)- I H -pyrazol -4-yl] -2H-tetrazole;
2- (4-bromobenzyl)-5- 5-bromo- l (2,4 -dichlorophenyl)- H -pyrazol -4-yl] -2H-tetrazole;
1 - 4-bromobenzyl)-5- 5-bromo-' (2,4 -dichlorophenyl)- H -pyrazol -4-yl] -2H-tetrazole;
2- 4-bromobenzyl)-5- 5-bromo- l (2,5 -dichlorophenyl)- H -pyrazol -4-yl] -2 H-tetrazole;
1- (4-bromobenzy l)-5 - 5-bromo- l (2,5 -dichlorophenyl)- H- -pyrazol -4-yl] -2 H-tetrazole;
2- 4-bromobenzyl)-5- 5-bromo-l (2,6 -dichlorophenyl)- H -pyrazol -4-yl] -2H-tetrazole;
1 - 4-bromobenzyl)-5- 5-bromo- i (2,6 -dichlorophenyl)- H- -pyrazol -4-yl] -2H-tetrazole;
2- 4-bromobenzyl)-5- 5-bromo- l (3,4 -dichlorophenyl)- H- -pyrazol -4-yl] -2H-tetrazole;
1 - (4-bromobenzyl)-5- 5-bromo- l (3,4 -dichlorophenyl)- H- -pyrazol -4-yl] -2 H-tetrazole;
2- 4-bromobenzyl)-5- 5-bromo- l (3,5 -dichlorophenyl)- H- -pyrazol -4-yl] -2H-tetrazole;
1 - (4-bromobenzyl)-5- 5-bromo- l (3,5 -dichlorophenyl)- H- -pyrazol -4-yl] -2H-tetrazole;
2- (4-bromobenzyl)-5- 5-bromo- l (2-bromophenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - 4-bromobenzyl)-5- 5-bromo- l (2-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2- (4-bromobenzyl)-5- 5-bromo- l (3-bromophenyl)-lH-pyrazoI-4-yl]-2H-tetrazole;
1 - 4-bromobenzy l)-5 - 5-bromo- l (3-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazoIe;
2- 4-bromobenzyl)-5- 5-bromo-l (4-bromophenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
173 1 - (4 -bromobenzyl -5- 5-bromo- 4-bromopheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- (4 -bromobenzyl' -5- 5-bromo- 4-fluorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - (4 -bromobenzyl^ -5- 5-bromo- 4-fluorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- (4 -bromobenzyl' -5- 5-bromo- 2-fluorophenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - (4 43romobenzylJ -5- 5-bromo- 2-fluoropheny 1)- 1 H-pyrazol-4-yI]-2H-tetrazole;
2- (4 -bromobenzyl^ -5- 5-bromo- 2,3-dimethylphenyl)- l [ H-pyrazol-4-yl ]-2H-tetrazole;
1 - (4 -bromobenzyl^ -5- 5-bromo- 2.3- dimethylphenyl)- ] I H-pyrazol-4-yl ]-2H-tetrazole;
.2- (4 -bromobenzyl^ -5- 5-bromo- 2.4- dimethylphenyl)- l I H-pyrazol-4-yl ]-2H-tetrazole;
1 - (4 -bromobenzyl' -5- 5-bromo- 2.4- dimethylpheny 1)- 1 I H-pyrazol-4-yl ]-2H-tetrazole;
2- (4 -bromobenzyl -5- 5-bromo- 2.5- dimethylphenyl)- 1 l H-pyrazol-4-yl ]-2H-tetrazole;
1 - (4 -bromobenzyl -5- 5-bromo- 2.5- dimethylphenyl)- l I H-pyrazol-4-yl ]-2H-tetrazole;
2- (4 -bromobenzyl -5- 5-bromo- 2.6- dimethy Iphenyl)- 1 I H-pyrazol-4-yl ]-2H-tetrazole;
1 - (4 -bromobenzyl -5- 5-bromo- 2,6-dimethylphenyl)- l I H-pyrazol-4-yl ]-2H-tetrazole;
2- (4 -bromobenzyl; -5- 5-bromo- 3, 4-dimethy Iphenyl)- 1 I H-pyrazol-4-yl ]-2H-tetrazole;
1 - (4 -bromobenzyl -5- 5-bromo- 3.4- dimethylphenyl)- 11 H-pyrazol-4-yl ]-2H-tetrazole;
2- (4 -bromobenzyl -5- 5-bromo- 3.5- dimethylphenyl)- l I H-pyrazol-4-yl ]-2H-tetrazole;
1 - (4 -bromobenzy -5- 5-bromo- 3,5-dimethylphenyl)- 1 [ H-pyrazol-4-yl ]-2H-tetrazole;
2- (4 -bromobenzyl' -5- 5-bromo- 2-ethylphenyl)- 1 H-pyrazol-4-y 1]-2H tetrazole;
1 - (4 -bromobenzyl] -5- 5-bromo- 2-ethylphenyl)- 1 H-pyrazol-4-yl]-2H- tetrazole;
2- (4 -bromobenzyl -5- 5-bromo- 4-ethylphenyl)- 1 H-pyrazol-4-y 1]-2H tetrazole;
1 - (4 -bromobenzyl -5- 5-bromo- 4-ethylphenyl)- l H-pyrazol-4-yl]-2H- tetrazole;
2- (4 -bromobenzyl -5- 5-bromo- 4-methoxyphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - (4 -bromobenzyl -5- 5-bromo- 4-methoxyphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- (4- -bromobenzyr -5- 5-bromo- 2-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - (4 -bromobenzyl) -5- 5-bromo- 2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- (4 -bromobenzyl) -5- 5-bromo- 4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
1 - (4- -bromobenzyr -5- 5-bromo- 4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
2- (4 -bromobenzyF -5- ^5-iodo- l -
1 - (4- -bromobenzyl) -5- ^5-iodo-l -
2- (4- -bromobenzyr -5- ; i -ethyl-5-
1 - (4- -bromobenzyr -5-( ; i -ethyl-5-
2- (4- -bromobenzyr -5- 5-iodo- l -
1 - (4 -bromobenzyl) -5- 5-iodo- l -
174 5-( 1 ·•benzyl-5-iodo l H-pyrazol-4-yl)-2-(4-bromobenzyl)-2H-tetrazole;
5-( l - ■benzyl-5-iodo l H-pyrazol-4-yl)-2-(4-bromobenzyl)-2H-tetrazole;
2-(4- ■bromobenzyl 5-iodo-l -phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
1- (4- ■bromobenzyl 5-iodo-l -phenyl-lH-pyrazol-4-yl)-2H-tetrazole;
2- (4- ■bromobenzyl 2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
1 - (4- ■bromobenzyl 2- chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- (4- ■bromobenzyl 3- chlorophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole;
1 - (4- ■bromobenzyl 1 -(3-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- (4- ■bromobenzyl 1 -(4-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - (4- bromobenzyl 4- chloropheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- (4- bromobenzyl 2,3-dichlorophenyl)-5- odo-l H-pyrazol-4-yl]-2H-tetrazole
1 - (4- bromobenzyl 2.3- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole
2- (4- bromobenzyl 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole
1 - (4- bromobenzyl 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole
2- (4- bromobenzyl 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole
1 - (4- bromobenzyl 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole
2- (4- bromobenzyl 2.6- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole
1 - (4- bromobenzyl 2,6-dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole
2- (4- bromobenzyl 1 - 3,4-dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl]-2H-tetrazole
1 - (4- bromobenzyl 3.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y l]-2H-tetrazole
2- (4- bromobenzyl 3.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y l]-2H-tetrazo)e
1 - (4- bromobenzyl 3,5-dichlorophenyl)-5- odo- 1 H-pyrazol-4-y l]-2H-tetrazole
2- (4- bromobenzyl 2-bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
1- (4- bromobenzyl 2- bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- (4- bromobenzyl 3- bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - (4- bromobenzyl 3- bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- (4- bromobenzyl 4- bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - (4- bromobenzyl 4-bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
2- (4- bromobenzyl 4-fluoropheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
1 - (4- bromobenzyl 4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole;
2- (4- bromobenzyl 2-fluorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
1 - (4- bromobenzyl 2-fluorophenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole;
2- (4- bromobenzyl 2,3-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole;
175 4-bromobenzyl)-5- 1 -(2,3-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole 4-bromobenzyl)-5- 1 -(2,4-dimethyiphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole 4-bromobenzyl)-5- 1 -(2,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazoie 4-bromobenzyl)-5- l -(2,5-dimethylphenyl)-5-iodo- lH-pyrazol-4-yl]-2H-tetrazo!e 4-bromobenzyl)-5- l -(2,5-dimethylphenyl)-5-iodo- lH-pyrazol-4-yl]-2H-tetrazole: 4-bromobenzyl)-5- l -(2,6-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5- 1 -(2,6-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole: 4-bromobenzyl)-5- 1 -(3,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole: 4-bromobenzyl)-5- 1 -(3,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-yl]-2H-tetrazole: 4-bromobenzyl)-5- 1 -(3,5-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazole; 4-bromobenzy l)-5 - l -(3,5-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5- l -(2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5- l -(2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5- l -(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5- l -(4-ethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5- 5-iodo- 1 -(4-methoxypheny!)- 1 H-pyrazol-4-yl |-2H-tetrazole; 4-bromobenzyl)-5- 5-iodo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-yl |-2H-tetrazole; 4-bromobenzyl)-5- 5-iodo-l -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 4-brQinobenzyl)-5- 5-iodo- l -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5- 5-iodo- l -(4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole; 4-bromobenzyl)-5- 5-iodo- l -(4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
[5 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazol-2-yl Jmethyl} benzonitrile;
[5 1 -methyl- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -yljmethyl} benzonitrile;
[5 1 -ethyl- l H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzonitrile;
[5-1 1 -ethyl- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -yl]methyl } benzon itri le;
{5- l -(2-methylpropyl)- l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5- l -(2-methylpropyl)-l H-pyrazol-4-yl]-l H-tetrazol- l -yl}methyl)benzonitrile;
[5- 1 -benzyl- 1 H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
[5- 1 -benzyl- 1 H-pyrazol-4-yl)-l H-tetrazol- 1 -yljmethyl} benzonitrile;
[5- 1 -phenyl- l H-pyrazol-4-yI)-2H-tetrazol-2-yl]methyl} benzonitrile;
[5- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -yl]methy 1} benzonitrile;
{5- l -(2-chlorophenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5- 1 -(2-chlorophenyl)-l H-pyrazol-4-yl]-l H-tetrazol- l -yl} methyl)benzonitrile;
176 {5-[l-(3-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l-yl}methyl)benzonitrile; {5-[l-(4-chlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5-[l-(4-chlorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonttrile; {5-[l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5-[l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonitrile; {5-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}rnethyl)benzonitrile; {5-[l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonitrile; {5-[l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5-[l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonitrile; {5-[l-(2;6-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5-[l-(2,6-dichIorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyI)benzonitrile; { 5-[ 1 -(3,4-dich loropheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazol-2-y 1 } methy l)benzonitri le; {5-[l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonitrile; {5-[l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; { 5-[l -(3, 5-dichloropheny 1)- 1 H-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile; {5-[l-(2-bromophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5-[l -(2-bromophenyl)-l H-pyrazoI-4-yl]-l H-tetrazol-1 -yl}methyl)benzonitrile; {5-[l-(3-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile; { 5-[ 1 -(3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl} methyl)benzonitrile; {5-[l-(4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5-[l-(4-bromophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l-yl}methyl)benzonitrile; {5-[l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5-[l-(4-fluoropheny I)- lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile; {5-[l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile; {5-[l-(2-fluorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile; {5-[l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile: { 5-[l -(2, 3-dimethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile: {5-[l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; {5-[l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile: {5-[l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile: {5-[l -(2, 5-dimethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1-yl} methy l)benzonitrile: {5-[l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile:
177 4 5-[ 1 -(2,6-dimethylphenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazo -1 -yl}methyI)benzonitrile; 4- 5-[l -(3,4-dimethylphenyl)-l H-pyrazol-4-yl]-2H-tetrazo -2-yl}methyl)benzonitrile; 4- 5-[l -(3,4-dimethylphenyl)- lH-pyrazol-4-yl]- l H-tetrazo - l -yl} methyl)benzonitrile; 4- 5-[l -(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazo -2-yl}methyl)benzonitrile; 4- 5-[l -(3, 5-dimethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazo - l -yl}methyI)benzonitrile; 4- 5-[l -(2-ethylphenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2-yl methyl)benzonitrile; 4- 5-[ 1 -(2-ethy lpheny 1)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -y 1 methyl)benzonitrile; 4- 5-[ 1 -(4-ethy lpheny 1)- 1 H-pyrazol-4-yl]-2H-tetrazol-2-y 1 methyl)benzonitrile; 4- 5-[ 1 -(4-ethy lpheny 1)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -y 1} methyl)benzonitrile; 4- 5-[l -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl)benzonitrile; 4- 5-[l -(4-methoxyphenyl)-l H-pyrazol-4-yl]- lH-tetrazol-l -yl}methyl)benzonitrile; 4- 5-[l -(2-methylphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl}methyl)benzonitrile; 4-. 5-[l -(2-methylphenyl)-l H-pyrazol-4-yl]-l H-tetrazol- l -yl} methyi)benzonitrile; 4- 5-[l -(4-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazoI-2-yl} methyl)benzonitrile; 4- 5-[l -(4-methylphenyl)- l H-pyrazol-4-yl]-l H-tetrazol- l -yl} methyl)benzonitriIe; 4- 5-(5-chloro- 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazol-2-y Ijmethy 1} benzonitri le; 4- 5-(5-chloro- 1 -methyl- 1 H-pyrazol-4-y 1)- 1 H-tetrazol- 1 -y Ijmethy 1} benzonitri le; 4- 5-(5-chloro-l -ethyl- l H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzOnitrile;
4- 5-(5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -y Ijmethy 1} benzonitrile;
4- 5-[5-chloro-l -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazol-2- yi methyl)benzonitrile;
4- 5-[5-chIoro- l -(2-methylpropy I)- 1 H-pyrazol-4-yl]- l H-tetrazol- 1 - yi methyl)benzonitrile;
4- 5-(l -benzyl-5-chloro- l H-pyrazol-4-yl)-2H-tetrazol-2-y Ijmethy 1} benzonitri le 4- 5-( 1 -benzyl-5-chloro- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -y Ijmethy 1} benzonitrile 4- 5-(5-chloro- l -phenyl-lH-pyrazol-4-yl)-2H-tetrazoI-2-yl]methyl} benzonitrile 4- 5-(5-chloro- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 H-tetrazol- 1 -yljmethy 1} benzonitrile 4- 5-[5 -chloro- 1 -(2-chloropheny 1)- 1 H-pyrazol-4-y 1 ] -2 H-tetrazo 1-2- yi methy l)benzon itri le;
4- 5-[5-chloro- 1 -(2-chlorophenyl)- 1 H-pyrazol-4-ylj- 1 H-tetrazol- 1 - yi methyl)benzonitrile;
4- 5-[5-chloro-l -(3-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yi methyl)benzonitrile;
178 4- ({5-[5-chloro-l-(3-chlorophenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l- yi fmethyl)benzonitrile;
4- ^{5-[5-chloro-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yi }methyl)benzonitrile;
4- ( { 5-[5 -chloro- 1 -(4-chloropheny 1)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi rmethyl)benzonitrile;
4- ( { 5-[5-chloro-l -(2,3-dichlorophenyl)- 1 H-pyrazol-4-y -2 H-tetrazol -2 - yi ■ methy l)benzonitrile;
4- ({5-[5-chloro-l-(2,3-dichlorophenyl)-lH-pyrazol-4-y - 1 H-tetrazol- 1 - yi methy l)benzonitrile;
4- ^{5-[5-chloro-l-(2,4-dic lorophenyl)-lH-pyrazol-4-yl -2H-tetrazol-2- yi methy l)benzonitrile;
4- ^5-[5-chloro-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl - 1 H-tetrazol- 1 - yi methy l)benzonitri le ;
4- ^{5-[5-chloro-l-(2,5-dichlorophenyl)-lH-pyrazoI-4-yl -2H-tetrazol-2- yi methy l)benzonitrile;
4- ^{5-[5-chloro-l-(2,5-dichlorophenyl)-l H-pyrazol-4-yl - 1 H-tetrazol- 1- yi methy l)benzonitrile;
4-< ^{5-[5-chloro-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl -2H-tetrazol-2- yij methyl)benzonitrile;
-( '{5-[5-chloro-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl - 1 H-tetrazol- 1 - yij methyl)benzonitrile; . . '
4-( {5-[5-chloro-l-(3,4-dichlorophenyl)-l H-pyrazol-4-y -2H-tetrazol-2- yi) methyl)benzonitrile;
4-( {5-[5-chloro-l-(3,4-dichIorophenyl)-l H-pyrazo.l-4-yIj - 1 H-tetrazol- 1- yi] methyl)benzonitrile;
4-( {5-[5-chloro-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl] -2H-tetrazol-2- yi) methy l)benzonitrile;
4-( {5-[5-chloro-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl] -1 H-tetrazol- 1- yi] methy l)benzonitrile;
4-( {5-[5-chloro-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yi) methyl)benzonitrile;
179 4-({5-[5-chloro- 1 -(2-bromopheny 1)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(3-bromophenyl)-lH-pyrazol-4-yI]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(3-bromophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(4-bromophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-chloro-l -(4-fluorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yl} methyl)benzonitrile;
4-({5-[5-chloro-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}rnethyl)benzonitrile;
4-({5-[5-chloro-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- y]}methyl)benzor>itrile;
4-({5-[5-chloro-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({ 5-[5-chloro- 1 -(2, 5-dimethy [phenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
180 4-({5-[5-chloro-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazoi-2- yl}methyl)benzonitrile;
4-({ 5-[5-chloro- 1 -(3,4-dimethylphenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(3,5-dimethylph.enyl)-lH-pyrazol-4-yl]-lH-tetrazol-l- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyi)benzonitrile;
4-({5-[5-chloro-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-( { 5-[5-chloro- 1 -(4-ethy lpheny 1)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- y 1 } methy l)benzonitri le ;
4-({5-[5-chloro-l-(2-methylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yl} methy l)benzonitrile;
4-({5-[5-chloro-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-chloro-l-(4-methylphenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l- yI}methyl)benzonitrile;
4-{[5-(5-bromo-l -methyl- lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile; 4- {[5-(5-bromo-l -methyl- 1 H-pyrazol-4-yl)-l H-tetrazol- l-yl]methyl}benzonitrite; 4-{[5-(5-bromo-l -ethyl- lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl}benzonitrile;
181 4- { [5-(5-bromo- 1 -ethyl- 1 H-pyrazol-4-y 1)- 1 H-tetrazol- 1 -y ljmethy 1} benzonitrile;
4-({5-[5-bromo-l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(2-methylpropyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1 - yl}methyl)benzonitrile;
4- {[5-(l-benzyl-5-bromo-lH-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzonitrile: 4-{[5-(l-benzyl-5-bromo-lH-pyrazol-4-yl)-l H-tetrazol- l-yl]methyl} benzonitrile; 4- { [5-(5-bromo- 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazol-2-y ljmethy 1 } benzonitri le 4-{[5-(5-bromo-l -phenyl- lH-pyrazol-4-yl)-l H-tetrazol- l-yl]methyl} benzonitrile 4-({5-[5-bromo-l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazoI-2- yl}methyl)benzonitrile;
4-( { 5-[5-bromo- 1 -(2-chlorophefty 1)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(3-ehlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(3-chlorophenyl)-l H-pyrazol-4-ylJ- 1 H-tetrazol- 1- y 1 } methy l)benzonitri le;
4-({5-[5-bromo-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(4-chlorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yl}methyl)benzonitrile;
4-({5-[5-bromo- 1 -(2,3-dichlorophenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(2,3-dichlorophenyl)-lH-pyrazol-4-yl]-lH-tetrazol-l- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(2,4-dichlorophenyl)-l H-pyrazol-4-yl]-l H-tetrazol- 1- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({ 5-[5-bromo- 1 -(2,5-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
182 4-({5-[5-bromo-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-lH-tetrazo)-l- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl} methy I)benzonitrile;
4-({5-[5-bromo- 1 -(3,4-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl} methy l)benzonitrile;
4-({5-[5-bromo- 1 -(3,5-dichlorophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- y 1 } methyl)benzonitrile;
4-({5-[5-bromo-l-(2-bromophenyl)-lH-pyrazol-4-y I]- 1 H-tetrazol- 1- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(3-bromophenyI)-tH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-( {5-[5-bromo- 1 -(3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl} methy l)benzonitri le;
4-({5-[5-bromo-l-(4-bromophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1 - yl} methy l)benzonitrile;
4-({5-[5-bromo-l-(4-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl} methy l)benzonitrile;
4-( { 5-[5-bromo- 1 -(4-fluoropheny 1)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yl} methy l)benzonitrile;
4-({5-[5-bromo-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2H-tetrazol-2- yl}methyl)benzonitrile;
4-({5-[5-bromo-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-l H-tetrazol- 1- yl}methyl)benzonitrile;
183 {5-[5-bromo- l -(2,3-d methylphenyl H-pyrazol-4-yl -2H-tetrazol-2 yi methyl)benzonitrile;
4- {5-[5-bromo- l -(2,3-d methylphenyl H-pyrazol-4-yl - 1 H-tetrazol- 1 yi methyl)benzonitrile;
4- {5-[5-bromo- l-(2,4-d methylphenyl H-pyrazol-4-yl -2H-tetrazol-2 yi methyl)benzonitrile;
4- {5-[5-bromo- l -(2,4-d methylphenyl H-pyrazol-4-yl -1 H-tetrazol- 1 yi methyl)benzonitrile;
4- {5-[5-bromo-l -(2,5-d methylphenyl H-pyrazol-4-yl -2 H-tetrazol -2 yi methyl)benzonitrile;
4- {5-[5-bromo- l -(2,5-d methylphenyl H-pyrazol-4-yl - 1 H-tetrazol- 1 - yi methyl)benzonitrile;
4- {5-[5-bromo-l -(2,6-d methylphenyl H-pyrazol-4-yl -2H-tetrazol-2- yi methyl)benzonitrile;
4- {5-[5-bromo-l -(2,6-d methylphenyl H-pyrazol-4-yl - 1 H-tetrazol- 1 - yi methyl)benzonitrile;
4- {5-[5-bromo- l -(3,4-d methylphenyl H-pyrazol-4-yl -2H-tetrazol-2- yi methyl)benzonitrile;
4- {5-[5-bromo-l -(3;4-d methylphenyl H-pyrazol-4-yl - 1 H-tetrazol- 1 - yi methyl)benzonitrile;
4- {5-[5-bromo-l -(3,5-d methylphenyl H-pyrazol-4-yl -2H-tetrazol-2- yi methyl)benzonitrile;
4- {5-[5-bromo-l -(3,5-d methylphenyl H-pyrazol-4-yl - 1 H-tetrazol- 1 - yi methyl)benzonitrile;
4- {5-[5-bromo- 1 -(2-ethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2- yi methyl)benzonitrile;
4- {5-[5-bromo-l -(2-ethylphenyl)-l H-pyrazol-4-yl]-l H-tetrazol- 1 - yi methyl)benzonitrile;
4- {5-[5-bromo- l -(4-ethylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazol-2- yi methyl)benzonitrile;
4- { 5-[5-bromo- 1 -(4-ethylphenyl)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yi methyl)benzonitrile;
184 4-({5-[5-bromo-l -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2H-tetrazol-2- y 1 } methy l)benzon itri le ;
4-( { 5-[5-bromo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y ]]- 1 H-tetrazol- 1 - yl}methyl)benzonitrile;
4-({5-[5-bromo-l -(2-methylphenyl)- lH-pyrazol-4-yl]-2H-tetrazol-2- yl} methyl)benzonitrile;
4-( { 5-[5-bromo- 1 -(2-methy lpheny 1)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yl} methy l)benzonitrile;
4-({5-[5-bromo- l -(2-methy lphenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-({5-[5-bromo- 1 -(2-methy lpheny 1)- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 -yl} methyl) benzonitrile;
4- { [5-(5-iodo-l -methyl- l H-pyrazol-4-yl)-2H-tetraZol-2-yl]methyl} benzonitrile; 4- { [5-(5-iodo- 1 -methyl- 1 H-pyrazol-4-y 1)- 1 H-tetrazol- 1 -y IJmethy 1 } benzonitri le; 4-{ [5-(l -ethyl-5-iodo-l H-pyrazol-4-yl)-2H-tetrazol-2-yl]methyl} benzonitrile; 4- {[5-( l -ethyl-5-iodo-l H-pyrazol-4-yl)-l H-tetrazol- l -yl]methyl} benzonitrile; 4-({5-[5-iodo-l -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methyl) benzonitrile;
4-( {5-[5-iodo-l -(2-methy lpropyl)-l H-pyrazol-4-yl]-l H-tetrazol- 1 -y IJmethy I) benzonitrile;
4-{ [5-(l-benzyl-5-iodo-l H-pyrazol-4-yl)-2H-tetrazol-2-yI]methyl} benzonitrile; 4-{[5-(l -benzyl-5-iodo- l H-pyrazol-4-yl)- l H-tetrazol- l -yl]methyl} benzonitrile; 4- { [5-(5-iodo- 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazol-2-y IJmethy 1} benzonitri le; 4-{[5-(5-iodo-l -phenyl- 1 H-pyrazol-4-yl)-l H-tetrazol- 1 -y IJmethy l}benzonitrile; 4-({5-[l -(2-chlorophenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazol-2- yl} methy l)benzonitrile;
4-({5-[l -(2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]- l H-tetrazol-l - yl} methyl)benzonitrile;
4-({5-[l -(3-chlorophenyl)-5-iodo- l H-pyrazol-4-ylJ-2H-tetrazol-2- yl}methyl)benzonitrile;
4-( { 5-[ 1 -(3-chloropheny l)-5-iodo- 1 H-pyrazol-4-y 1]-1 H-tetrazol- 1 - yl} methyl)benzonitrile;
185 4-({5-[l -(4-chlorophenyl)-i5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2 yl}methyl)benzonitrile;
4-({ 5-[ 1 -(4-chlorophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 yl} methyl)benzonitrile;
4-( { 5-[ 1 -(2,3-dichloropheny l)-5-iodo- 1 H-pyrazo l-4-yl]-2H-tetrazol-2 yl} methyl)benzonitrile;
4-( { 5-[ 1 -(2,3-dichloropheny l)-5-iodo- 1 H-pyrazo l-4-yl]- l H-tetrazol- 1 yI}methyl)benzonitrile;
4-({5-[l -(2,4-dichlorophenyl)-5-iodo- l H-pyrazo l-4-y[]-2H-tetrazol-2 yl} methyl)benzonitrile;
4-({5-[ l -(2,4-dichlorophenyl)-5-iodo- l H-pyrazo l-4-yl]-l H-tetrazol- 1 yl} methyl)benzonitrile;
4-({5-[l -(2,5:dichlorophenyl)-5-iodo-l H-pyrazo l-4-yl]-2H-tetrazol-2 yl} methyl)benzonitrile; .
4-( { 5-[ 1 -(2,5-dichloropheny l)-5-iodo- 1 H-pyrazo l-4-yl]- l H-tetrazol- 1 yl}methyl)benzonitrile;
4-({5-[l -(2, 6-dichlorophenyl)-5-iodo- l H-pyrazo l-4-yl]-2H-tetrazoI-2- • yl}methyl)benzonitrile;
4-( { 5-[ 1 -(2,6-dichloropheny l)-5-iodo- 1 H-pyrazo Ι-4-ylJ- l H-tetrazol- 1 yl}methyl)benzonitriie;
4-({5-[l -(3,4-dichlorophenyl)-5-iodo-l H-pyrazo l-4-yl]-2H-tetrazol-2 yl}methyl)benzonitrile; .
4-( { 5-[ 1 -(3,4-dichlorophenyl)-5-iodo- 1 H-pyrazo l-4-yl]-l H-tetrazol- 1 yl}methyl)benzonitrile;
4-({5-[l -(3,5-dichlorophenyl)-5-iodo-l H-pyrazo l-4-yl]-2H-tetrazol-2 yl} methyl)benzonitrile;
4-({5-[ l -(3,5-dichlorophenyl)-5-iodo-l H-pyrazo -4-yl]- l H-tetrazol- 1 yl} methyl)benzonitrile;
4-( { 5-[ 1 -(2-bromopheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazol-2 yl}methyl)benzonitrile;
4-({5-[l -(2-bromopheny I)-5-iodo-l H-pyrazol-4-yl]- l H-tetrazol- 1 yl} methyl)benzonitrile;
186 4- {5- l -(3-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2- yi me thyl)benzonitrile;
4- {5- ' 1 -(3-bromophenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 H-tetrazol- 1 - yi me thyl)benzonitrile;
5 4- {5- l -(4-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2- yi me thyl)benzonitrile;
4- 1(5- ' ] -(4-b'romophenyl)-5-iodo- 1 H-pyrazol-4-yl]- ] H-tetrazol- 1 - yi] me thyl)benzonitrile;
4-( :{5- ' 1 -(4-fluoropheny l)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazol-2-
10 yi] me thyl)benzonitrile;
4-< :{5- l -(4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-l H-tetrazol- 1 - yi me thyl)benzonitrile;
4- :{5- l -(2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2- yi. me thyl)benzonitrile;
!5 4-( ;{5- 1 -(2-fluoropheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 -
" yi] me thyl)benzonitrile;
4-( :{5- l -(2,3-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2- yi] me thyl)benzonitrile;
4-( :{5- 1 -(2, 3-dimethylphenyl)-5.-iodo-lH-pyrazol-4-yl]- l H-tetrazol- 1 -
20 - yi] me thyl)benzonitrile;
4-( '{5- l -(2,4-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2- yi] me thyl)benzonitrile;
4-( (5- 1 -(2, 4-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-yl]- 1 H-tetrazol- Γ- y'] me thyl)benzonitrile;
25 4-( {5- 1 -(2,5-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2H-tetrazol-2- yi] me thyl)benzonitrile;
4-( {5- ' 1 -(2,5-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi] me thyl)benzonitrile;
4-( {5- l -(2,6-dimethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazol-2-
30 yi] me thyl)benzonitrile;
4-( {5- 1 -(2, 6-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-l H-tetrazol- 1 - yi) mel thyl)benzonitrile;
187 4- {5-[l -(3,4-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2- yi methyl)benzonitrile;
4- {5-[ 1 -(3,4-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi methy l)benzohitrile;
4-1 {5-[l -(3,5-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2H-tetrazol-2- yi methyl)benzonitrile;
4- {5-[ 1 -(3,5-dimethylpheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi methyl)benzonitrile;
4- {5-[l -(2-ethylphenyl)-5-iodo-l H-pyrazoI-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile; 4- { 5-[ 1 -(2-ethy lphenyl)-5-iodo- 1 H-pyrazol-4-y I]- 1 H-tetrazol- 1 -y 1 } methy l)benzonitrile; 4- {5-[l -(4-ethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2H-tetrazol-2-yl} methy l)benzonitrile; 4- {5-[l -(4-ethyiphenyl)-5-iodo-l H-pyrazol-4-yl]-l H-tetrazol- l -yl} methyl)benzonitrile; 4- { 5-[5-iodo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y l]-2H-tetrazol-2- yi methyl)benzonitrile;
4- { 5-[5 -iodo- 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y 1]- 1 H-tetrazol- 1 - yi methyl)benzonitrile;
4- {5-[5-iodo- l -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazol-2- y> methyl)benzonitrile;
4- {5-[5-iodo-l -(2-methylphenyl)-lH-pyrazol-4-yl]-l H-tetrazol- l - yi methyl)benzonitrile;
4- { 5-[5-iodo- 1 -(4-methy lpheny 1)- 1 H-pyrazol-4-y l]-2H-tetrazol-2- yi methyl)benzonitrile;
4- { 5-[5-iodo- 1 -(4-methy lpheny 1)- 1 H-pyrazol-4-y I]- 1 H-tetrazol- 1 - yi methyl)benzonitrile;
2- 4-methoxybenzyl)-5-( 1 -methyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
1 - 4-methoxybenzyl)-5-( l -methyl- l H-pyrazol-4-yl)-2H-tetrazole;
5- 1 -ethyl- l H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5- 1 -ethyl- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzyl)-2H-tetrazole;
2 4-methoxybenzyl)-5-[l -(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
2 4-methoxybenzyl)-5-[l -(2-methylpropyl)- l H-pyrazol-4-yl]-2H-tetrazole;
5 1 -benzyl- l H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5 1 -benzyl- 1 H-pyrazol-4-y 1)- 1 -(4-methoxybenzy l)-2H-tetrazole;
2 4-methoxybenzyl)-5-( l -phenyl- l H-pyrazol-4-yl)-2H-tetrazole;
188 1 - (4-methoxybenzy l)-5-( 1 -phenyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
5- [ i - (2-chlorophenyl)- 1 H-pyrazol-4-yl]-2- ;4-methoxybenzyi)-2H-tetrazole;
5- [i - (2-chloropheny 1)- 1 H-pyrazol-4-yl]- 1 - ^4-methoxybenzyl)-2H-tetrazole;
5- [i - (3-chlorophenyl)-l H-pyrazol-4-yl]-2- (4-methoxybenzy l)-2H-tetrazole;
5- [ 1 - (3-chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 - ;4-methoxybenzyl)-2H-tetrazole;
5- [i - (4-chlorophenyl)-l H-pyrazol-4-yl]-2- ^4-methoxybenzyl)-2H-tetrazole;
5- [· - (4-chloropheny 1)- 1 H-pyrazol-4-yl]- 1 - '4-methoxybenzyl)-2H-tetrazole;
5- [i - (2,3-dichlorophenyl)-l H-pyrazol-4-yl ]-2-(4-methoxybenzyl)-2H-tetrazole;
5- [ i - (2,3-dichlorophenyl)- l H-pyrazol-4-yl ]- l -(4-methoxybenzyl)-2H-tetrazole;
5- [i - (2,4-dichlorophenyl)-l H-pyrazol-4-yl ]-2-(4-methoxybenzyl)-2H-tetrazole;
5- [i - (2,4-dichlorophenyl)- 1 H-pyrazol-4-yl ]- l -(4-methoxybenzy l)-2H-tetrazole;
5- [i - (2,5-dichlorophenyl)-l H-pyrazol-4-yl ]-2-(4-methoxybenzyl)-2H-tetrazole;
5- [i - (2,5 -d ich loropheny 1)- 1 H-pyrazol-4-y 1 ]-l -(4-methoxybenzy l)-2H-tetrazole;
5- [·- (2,6-dichlorophenyl)-l H-pyrazol-4-yl |-2-(4-methoxybenzyl)-2H-tetrazole;
5- [1 - (2,6-dichlorophenyl)- l H-pyrazol-4-yl |- 1 -(4-methoxybenzy l)-2H-tetrazole;
5- 1 - (3,4-dichlorophenyl)- l H-pyrazol-4-yl |-2-(4-methoxybenzyl)-2H-tetrazole;
5- [ i - (3,4-dichloropheny!)- l H-pyrazol-4-yl |- 1 -(4-methoxybenzy l)-2H-tetrazole;
5- ;i - (3,5-dichlorophenyl)-l H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole;
5- [ 1 - (3,5-dichlorophenyl)-l H-pyrazol-4-yl |- 1 -(4-methoxybenzyl)-2H-tetrazole;
5- [i - (2-bromophenyl)-lH-pyrazol-4-yl]-2- 4-methoxybenzy l)-2H-tetrazole;
5- 1 - (2-bromophenyl)- 1 H-pyrazol-4-yl]- 1 - (4-methoxybenzy l)-2 H-tetrazo le ;
5- ;i - (3-bromophenyl)-l H-pyrazol-4-yl]-2- (4-methoxybenzyl)-2H-tetrazole;
5- 1 - ;3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 - (4-methoxybenzyl)-2H-tetrazole;
5-1 1 - ^4-bromophenyl)-l H-pyrazol-4-yl]-2- 4-methoxybenzy l)-2H-tetrazole;
5-1 1 - ^4-bromophenyl)-l H-pyrazol-4-yl]- 1 - 4-methoxybenzy l)-2H-tetrazole;
5-1 1 - (4-fluorophenyl)- 1 H-pyrazol-4-yl]-2-( 4-methoxybenzy l)-2H-tetrazole;
5-1 1 - ^4-fIuoropheny 1)- 1 H-pyrazol-4-y 1]- 1 -( 4-methoxybenzy I)-2H-tetrazole;
5-[ 1 - ^-fluorophenyl)- 1 H-pyrazol-4-yl]-2-( 4-methoxybenzyl)-2H-tetrazole;
5-1 1 - (2-fluorophenyl)-l H-pyrazol-4-yl]- 1 -( 4-methoxybenzyl)-2H-tetrazole;
5-1 1 - (2,3-dimethylphenyl)-l H-pyrazol-4-yi ]-2-(4-methoxybenzyl)-2H-tetrazole;
5-1 1 - (2,3-dimethylphenyl)-l H-pyrazol-4-y! ]- \ -(4-methoxybenzy l)-2H-tetrazole;
5-1 1 - (2,4-dimethylphenyl)- l H-pyrazol-4-y: ]- 1 -(4-methoxybenzy l)-2H-tetrazole;
5-[ 1 - '2,4-dimethy lpheny 1)- 1 H-pyrazol-4-y 1 ]- 1 -(4-methoxybenzyl)-2H-tetrazole;
189 l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; l-(2,5-dimethylphenyl)-lH-pyrazoI-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
1 -(2-ethylphenyl)- 1 H-pyrazol-4-yl]-l -(4-methoxybenzy l)-2H-tetrazole;
l-(4-ethylphenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
1 -(4-ethylpheny I)- 1 H-pyrazol-4-yl]-l -(4-methoxybenzy l)-2H-tetrazole;
4-methoxybenzyl)-5-[l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4-methoxybenzyI)-5-[l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4-methoxybenzyl)-5-[l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4-methoxybenzy l)-5-[l-(2-methylphenyl)-lH-pyrazol-4-yl]-2H-tetfazole;
4-methoxybenzyl)-5-[l-(4-methy!phenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
4- methoxybenzyl)-5-[l-(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
5- chloro- 1 -methyl- 1 H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5-chloFo-l -methyl- lH-pyrazol-4-yl)-l -(4-methoxybenzy l)-2H-tetrazole;
5-chloro- 1 -ethyl- lH-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzy l)-2H-tetrazole;
5-chloro- l-(2-methylpropyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5-chloro- l-(2-methylpropyl)-l H-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; l-benzyl-5-chloro-lH-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
1 -benzyl-5-chloro- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzy l)-2H-tetrazole;
5-chloro- 1 -phenyl- 1 H-pyrazol-4-yl)-2-(4-methoxybenzy l)-2H-tetrazole;
5-chloro- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzyl)-2H-tetrazole;
5-chloro- l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5-chloro- l-(2-chlorophenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole; 5-chloro- l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5-chloro- l-(3-chlorophenyI)-lH-pyrazol-4-yl]-l -(4-methoxybenzy l)-2H-tetrazole; 5-chloro- l-(4-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
190 5-15-chloro- 1 -(4-chloropheny 1)- 1 H-pyrazol-4-y 1]- 1 - 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro-l -(2,3-dichlorophenyl)-lH-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole;
5-1 5-chloro- l -(2,3-dichlorophenyl)-lH-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tetrazole; 5-1 5-chloro- 1 -(2, 4-dichlorophenyl)-l H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole; 5-1 5-chloro- 1 -(2,4-dichlorophenyl)- ί H-pyrazol-4-y 1 - 1 -(4-methoxybenzyl)-2H-tetrazole; 5-1 5-chloro- 1 -(2, 5-dichlorophenyl)- l H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2, 5-dichlorophenyl)- 1 H-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2,6-dichlorophenyl)- 1 H-pyrazol-4-y 1 -2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- 1 -(2, 6-dichlorophenyl)-l H-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro-l -(3,4-dichlorophenyl)-l H-pyrazol-4-yl ^^-methoxybenzy ^H-tetrazole; 5- 5-chloro- 1 -(3,4-dichlorophenyl)- 1 H-pyrazol-4-yl - 1 -(4-methoxybenzy l)-2H-tetrazole; 5-, 5-chloro- 1 -(3, 5-dichlorophenyl)- l H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole; 5-1 5-chloro- 1 -(3, 5-dichlorophenyl)- lH-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tefrazole; 5 1 -(2-bromopheny l)-5-chloro- 1 H-pyrazol-4-y l]-2- 4-methoxybenzy l)-2H-tetrazole; 5 l -(2-bromophenyl)-5-chloro-lH-pyrazol-4-yl]- l - 4-methoxybenzyl)-2H-tetrazole; 5 l -(3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2- 4-methoxybenzy l)-2H-tetrazole; 5 1 -(3-bromopheny l)-5-chloro- 1 H-pyrazol-4-y I]- 1 - 4-methoxybenzyl)-2H-tetrazole; 5' 1 -(4-bromopheny l)-5-chloro- 1 H-pyrazol-4-y l]-2-> 4-methoxybenzy l)-2H-tetrazole; 5' 1 -(4-bromopheny l)-5-chloro-l H-pyrazol-4-yl]- 1 -< 4-methoxybenzy l)-2H-tetrazole; 5- 5-chloro-l -(4-fluorophenyl)-l H-pyrazol-4-yl]-2 4-methoxybenzy l)-2H-tetrazole; 5- 5-chloro- 1 -(4-fluoropheny 1)- 1 H-pyrazol-4-y l]-2 4-methoxybenzyl)-2H-tetrazole; ·5· 5-chloro- l -(2-fluorophenyl)- l H-pyrazol-4-yl]-2 4-methoxybenzy l)-2H-tetrazole; 5· 5-chloro- l -(2-fluorophenyl)-lH-pyrazol-4-yl]- l 4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- l -(2,3-dimethylphenyl)-l H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole 5· 5-chloro- 1 -(2, 3-dimethylphenyl)-l H-pyrazol-4-y ]- 1 -(4-methoxybenzy l)-2H-tetrazole 5- 5-chloro- 1 -(2, 4-dimethylphenyl)-l H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole 5- 5-chloro- 1 -(2, 4-dimethylphenyl)-l H-pyrazol-4-y ]- 1 -(4-methoxybenzyl)-2H-tetrazole5- 5-chloro- 1 -(2, 5-dimethylphenyl)-l H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole: 5-1 5-chloro- 1 -(2, 5-dimethylphenyl)-lH-pyrazol-4-y ]- 1 -(4-methoxybenzyl)-2H-tetrazole: 5 5-chloro-l -(2,6-dimethylphenyl)-l H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole; 5 5-chloro- 1 -(2, 6-dimethylphenyl)-l H-pyrazol-4-y ]- 1 -(4-methoxybenzy l)-2H-tetrazole; 5 5-chloro- 1 -(3,4-dimethy lpheny 1)- 1 H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole: 5 5-chloro- 1 -(3,4-dimethylpheny 1)- 1 H-pyrazol-4-y i ]- 1 -(4-methoxybenzyl)-2H-tetrazole;
191 5-chloro -(3,5-dimethylphenyl)- l H-pyrazol-4-ylJ-2-(4-methoxybenzyl)-2H-tetrazole; 5-chloro -(3,5-dimethylphenyl)-l H-pyrazol-4-yl]- l -(4-methoxybenzyl)-2H-tetrazole; 5-chloro -(2-ethylphenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5-chloro- -(2-ethylphenyl)- l H-pyrazol-4-yl]- l-(4-methoxybenzyl)-2H-tetrazole;
5- 5-chloro -(4-ethylphenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro -(4-ethylphenyl)- 1 H-pyrazol-4-yl]- 1 -(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- -(4-methoxyphenyl)-l H-pyrazol-4-yl]- l -(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- -(2-methylphenyl)- l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- -(2-methylpheny 1)- 1 H-pyrazol-4-y 1]- 1 -(4-methoxybenzy l)-2H-tetrazole; 5- 5-chloro- -(4-methylphenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-chloro- -(4-methylpheny 1)- 1 H-pyrazol-4-yl]- 1 -(4-methoxybenzy l)-2H-tetrazole; 5- 5-bromo -methyl- l H-pyrazoI-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5- 5-bromo -methyl- l H-pyrazol-4-yl)- l -(4-methoxybenzyl)-2H-tetrazole;
5- 5-bromo -ethyl- l H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5- 5-bromo -ethyl- l H-pyrazol-4-yl)-l -(4-methoxybenzy l)-2H-tetrazole;
5- 5-bromo -(2-methylpropyl)- l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-bromo -(2-methylpropyl)- 1 H-pyrazol-4-y 1]- 1 -(4-methoxybenzyl)-2H-tetrazole; 5- 1 -benzyl bromo-l H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5- 1 -benzyl bromo- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzyl)-2H-tetrazole;
5- 5-bromo phenyl- 1 H-pyrazol-4-yI)-2-(4-methoxybenzyl)-2H-tetrazole;
5- 5-bromo phenyl- lH-pyrazol-4-yl)- l -(4-methoxybenzy l)-2H-tetrazole;
5- 5-bromo (2-chlorophenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-bromo (2-chlorophenyl)-l H-pyrazol-4-yl]- l -(4-methoxybenzyl)-2H-tetrazole; 5- 5-bromo (3-chlorophenyl)- l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-bromo (3-chlorophenyl)- 1 H-pyrazol-4-yl]- 1 -(4-methoxybenzyl)-2H-tetrazole; 5- 5-bromo (4-chlorophenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5- 5-bromo (4-chlorophenyl)- l H-pyrazol-4-yl]- l -(4-methoxybenzyl)-2H-tetrazole;
5-bromo (2,3-dichlorophenyl)-l H-pyrazoi-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5-bromo l (2,3-dichlorophenyl)-l H-pyrazol-4-yl]- l -(4-methoxybenzy l)-2H-tetrazole; 5-bromo -l 2,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole; 5-bromo l-i 2.4- dichlorophenyl)-l H-pyrazol-4-yl]-l -(4-methoxybenzy l)-2H-tetrazole; 5-bromo - I - 2.5- dichlorophenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
192 5-[5-bromo-l-(2,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole
5-[5-br0mo-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole
5-[5-br0mo-l-(2,6-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole
5-[5-bromo-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole:
5-[5-bromo-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole:
5-[5-bromo-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole:
5-[5-bromo-l-(3,5-dichlorophenyl)-lH-pyrazoI-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo- 1 -(2-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(3-bromophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(3-bromophenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5 -bromo- 1 -(4-bromopheny 1)- 1 H-pyrazoI-4-y 1]- 1 -(4-methoxybenzy l)-2H-tetrazole;
5-[5-bromo-l-(4-fluorophenyl)-lH-pyrazoI-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(4-fluorophenyl)-l H-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo- 1 -(2-fluoropheny I)- 1 H-pyrazol-4-y l]-2-(4-methoxybenzy l)-2H-tetrazole;
5-[5-bromo-l -(2-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole;
5-[5-bromo- 1 -(2,3-dimethy Ipheny 1)- 1 H-pyrazol-4-yl]- 1 -(4-methoxybenzyl)-2H- tetrazole;
5-[5-bromo- 1 -(2,4-dimethylphenyl)- 1 H-pyrazol-4-y l]-2-(4-methoxybenzyl)-2H- tetrazole;
5-[5-bromo-l-(2,4-dimethy Ipheny l)-lH-pyrazol-4-yl]-l -(4-methoxybenzy 1)-2H- tetrazole;
5-[5-bromo-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole;
5-[5-bromo-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H- tetrazole;
5-[5-bromo-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole;
5-[5-bromo-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H- tetrazole;
193 5-[5-bromo-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H- tetrazole;
5-[5-bromo-l -(3,4-dimethylphenyl)- 1 H-pyrazol-4-y 1]- 1 -(4-methoxybenzyl)-2H- tetrazole;
5-[5-bromo-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-. tetrazole;
5-[5-bromo-l-(3,5-dimethylphenyl)- H-pyrazol-4-yl]-l-(4-rnethoxybenzyl)-2H- tetrazole;
5-[5-bromo-l-(2rethylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(4-ethylphenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-brorno-l-(4-ethylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(4-rnethoxyphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-brorno-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(2-methylphenyl)-l H-pyrazoI-4-yl]-l -(4-methoxybenzy l)-2H-tetrazole;
5-[5-bromo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-bromo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-(5-iodo- 1 -methyl- lH-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5-(5-iodo-l -methyl- lH-pyrazol-4-yl)-l-(4-methoxybenzyl)-2H-tetrazole;
5-(l-ethyl-5-iodo-lH-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5-(l-ethyl-5-iodo-lH-pyrazol-4-yl)-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-iodo-l-(2-methylpropyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-iodo-l-(2-methylpropyl)-l H-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-(l-benzyl-5-iodo-l H-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5-(l-benzyl-5-iodo-lH-pyrazol-4-yl)-l-(4-methoxybenzyl)-2H-tetrazole;
5-(5-iodo-l -phenyl- lH-pyrazol-4-yl)-2-(4-methoxybenzyl)-2H-tetrazole;
5-(5-iodo- 1 -phenyl- 1 H-pyrazol-4-yl)- 1 -(4-methoxybenzy l)-2H-tetrazole;
5-[l-(2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[l-(2-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l -(4-methoxybenzy l)-2H-tetrazole;
5-[l-(3-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[l-(3-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l -(4-methoxybenzy l)-2H-tetrazole;
5-[l-(4-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
194 5- [i- (4-chlorophenyl)-5-iodo-lH-pyrazol-4-yl]-l- 4-methoxybenzyl)-2H-tetrazole;
5- [i- (2,3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl |-2-(4-methoxybenzyl)-2H-tetrazole
5- [i- (2,3-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl |-l-(4-methoxybenzyl)-2H-tetrazole
5- [i- (2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl |-2-(4-methoxybenzyl)-2H-tetrazole
5- [i- (2,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tetrazole
5- [1- (2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole
5- [i- (2,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl |-l-(4-methoxybenzyl)-2H-tetrazole
5- [i- (2,6-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole
5- [i- (2,6-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl - 1 -(4-methoxybenzy l)-2H-tetrazole
5- [i- (3,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole
5- [i- (3,4-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl - 1 -(4-methoxybenzyl)-2H-tetrazole
5- ;i- (3,5-dichlorophenyl)-5-iodo- 1 H-pyrazol-4-yl -2-(4-methoxybenzyl)-2H-tetrazole
5- [i- (3,5-dichlorophenyl)-5-iodo-lH-pyrazol-4-yl - 1 -(4-methoxybenzy l)-2H-tetrazole
5- [i- (2-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2- (4-methoxybenzyl)-2H-tetrazole;
5- [i- (2-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-l- ^4-methoxybenzyl)-2H-tetrazole;
5- Ί- (3-bromQphenyl)-5-iodo-lH-pyrazol-4-yl]-2- 4-methoxybenzyl)-2H-tetrazole;
5- ;i- (3-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-l- (4-methoxybenzyl)-2H-tetrazole;
5- Ί- (4-bromophenyl)-5-iodo-lH-pyrazol-4-yl]-2- 4-methoxybenzyl)-2H-tetrazole;
5- ;i- (4-bromopheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 - (4-methoxybenzyl)-2H-tetrazole;
5- 1- (4-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-( 4-methoxybenzy l)-2H-tetrazole;
5- 1- (4-fluoropheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -( 4-methoxybenzy l)-2H-tetrazole;
5- ;i- (2-fluorophenyl)-5-iodo-lH-pyrazol-4-yl]-2-( 4-methoxybenzy l)-2H-tetrazole;
5- 1- (2-fluorophenyl)-5-iodo-lH pyrazol-4-yl]-l-( 4-methoxybenzy l)-2H-tetrazole;
5- .1- (2,3-dimethylphenyl)-5-iodo- 1 H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole
5- ;i- (2,3-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-y ]- 1 -(4-methoxybenzy l)-2 H-tetrazole
5- ;i- (2,4-dimethylphenyl)-5-iodo-lH-pyrazGl-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole
5- Ί- (2,4-dimethylphenyl)-5-iodo-lH-pyrazol-4-y ]- 1 -(4-methoxybenzyl)-2H-tetrazole
5-1 1- ,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole
5- 1- '2,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-y ]-l-(4-methoxybenzyl)-2H-tetrazole
5- 1- (2,6-dimethylphenyl)-5-iodo-lH-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole
5- 1- (2,6-dimethylpheny])-5-iodo-lH-pyrazol-4-y ]- 1 -(4-methoxybenzy l)-2H-tetrazole
5-1 1- 3,4-dimethy lphenyl)-5-iodo- 1 H-pyrazol-4-y ]-2-(4-methoxybenzyl)-2H-tetrazole
5-[ 1- (3,4-dimethylpheny l)-5-iodo- 1 H-pyrazol-4-y! ]- 1 -(4-methoxybenzyl)-2H-tetrazole
195 5-[l-(3,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[l-(3,5-dimethylphenyl)-5-iodo-lH-pyrazol-4-y]]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[l-(2-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[l-(2-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[ 1 -(4-ethy lphenyl)-5-iodo- 1 H-pyrazol-4-y l]-2-(4-methoxybenzy l)-2H-tetrazole;
5-[ 1 -(4-ethylphenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -(4-methoxybenzyl)-2H-tetrazole;
5-[5-iodo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-iodo-l-(4-met oxyphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-iodo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-iodo-l-(2-methylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
5-[5-iodo-l-(4-methylphenyl)-l H-pyrazol-4-yl]-2-(4-methoxybenzyl)-2H-tetrazole;
5-[5-iodo-l-(4-methylphenyl)-lH-pyrazol-4-yl]-l-(4-methoxybenzyl)-2H-tetrazole;
2-(3-methy lbenzy l)-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole;
1 -(3-methy lbenzyl)-5-( 1 -methyl- 1 H-pyrazol-4-y l)-2H-tetrazole;
5-(l -ethyl- lH-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5-( 1 -ethyl- 1 H-pyrazol-4-y I)- 1 -(3-methylbenzy l)-2H-tetrazole;
2-(3-methylbenzyl)-5-[l-(2-methylpropyl)-l H-pyrazol-4-yl]-2H-tetrazole;
1 - (3-methy lbenzyl)-5-[l-(2-methylpropyl)-lH-pyrazol-4-yl]-2H-tetrazole;
5-( 1 -benzyl- 1 H-pyrazol-4-y l)-2-(3-methy lbenzyl)-2H-tetrazole;
5-( 1 -benzyl- 1 H-pyrazol-4-yl)- 1 -(3-methy lbenzyl)-2H-tetrazole;
2- (3-methylbenzyl)-5-(l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
1 -(3-methy lbenzyl)-5-(l -phenyl- lH-pyrazol-4-yl)-2H-tetrazole;
5-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[l-(2-chlorophenyl)-lH-pyrazol-4-yl]-l -(3-methy lbenzyl)-2H-tetrazole;
5-[l-(3-chlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[l-(3-chlorophenyl)-l H-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole;
5-[l-(4-chlorophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[ 1 -(4-chloropheny 1)- 1 H-pyrazol-4-yl]- 1 -(3-methy lbenzy l)-2H-tetrazole;
5-[]-(2,3rdichlorophenyl)-lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-[ 1 -(2,3-dichloropheny 1)- 1 H-pyrazol-4-yl]- 1 -(3-methy lbenzy l)-2H-tetrazole;
5-[l -(2, 4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(3-methy lbenzy l)-2H-tetrazole;
5-[l -(2, 4-dichlorophenyl)-lH-pyrazol-4-yl]-l -(3-methy lbenzy l)-2H-tetrazole;
5-[l-(2,5-dichlorophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
196
2.5- dichlorophenyl)-l H-pyrazol-4-yl ]- 1 -(3-methy lbenzy l)-2H-tetrazole;
2.6- dichlorophenyl)-l H-pyrazol-4-yl ]-2-(3-methylbenzyl)-2H-tetrazole; 2,6-dichlorOphenyl)- 1 H-pyrazol-4-y 1 ]- 1 -(3-methylbenzy l)-2H-tetrazole; 3,4-dichlorophenyl)-lH-pyrazol-4-yl ]-2-(3-methylbenzyl)-2H-tetrazole;
3.4- dichIorophenyI)- 1 H-pyrazol-4-y I ]- 1 -(3-methylbenzy l)-2H-tetrazole;
3.5- dichlorophenyl)-l H-pyrazol-4-yl ]-2-(3-methylbenzyl)-2H-tetrazole; 3 , 5 -d ich loropheny 1)- 1 H-py razo 1-4-y I ]-l -(3-methylbenzy l)-2H-tetrazole; 2-bromophenyl)- 1 H-pyrazol-4-yl]-2-i (3-methy lbenzy l)-2H-tetrazole;
2- bromopheny 1)- lH-pyrazol-4-y 1]- 1 -i (3-methy lbenzy l)-2H-tetrazole;
5 3- bromophenyl)-l H-pyrazol-4-yl]-2-i (3-methy lbenzyl)-2H-tetrazole; 5 3- bromophenyl)- 1 H-pyrazol-4-y 1]- 1 -i (3-methylbenzyl)-2H-tetrazole; 5 4- bromopheny 1)- 1 H-pyrazol-4-y l]-2-i (3-methylbenzy l)-2H-tetrazole;
4-bromopheny 1)- 1 H-pyrazol-4-y 1]- 1 -i (3-methy lbenzy l)-2H-tetrazole; 4-fluorophenyl)- l H-pyrazol-4-yl]-2-( 3-methy lbenzy l)-2H-tetrazole; 4-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -( 3-methy lbenzyl)-2H-tetrazole;
1 - 2-fluorophenyl)- 1 H-pyrazol-4-yl]-2-( 3-methy lbenzy l)-2H-tetrazole;
2-fluorophenyl)-l H-pyrazol-4-yl]-l -( 3-methylbenzyl)-2H-tetrazole;
5- [i - (2,3 -dimethylphenyl)- 1H ■pyrazol -4-yl]-2- (3 -methylbenzyl)-2H-tetrazole;
5- [i - (2,3 -dimethylphenyl)- 1 H -pyrazol -4-yl]- l - (3 -m ethy 1 benzy l)-2H-tetrazole ;
5- 1 - (2,4 -dimethylphenyl)- 1 H -pyrazol -4-yl]-2- (3 -methylbenzyl)-2H-tetrazole;
5- [i - (2,4 -dimethylphenyl)- 1 H -pyrazol -4-yl]-l - (3 -methy lbenzy l)-2H-tetrazole;
5- 1 - (2,5- -dimethylphenyl)- 1 H -pyrazol -4-yl]-2- (3 -methy lbenzy l)-2H-tetrazole;
5- [1 - (2,5 -dimethylphenyl)- I H -pyrazol -4-yl]-l - (3 -methy lbenzy l)-2H-tetrazole;
5- Ί - (2,6· -dimethylphenyl)- 1H- -pyrazol -4-yl]-2- (3 -methy lbenzy l)-2H-tetrazole;
5- [1 - (2,6 -dimethylphenyl)- 1 H -pyrazol -4-yl]-l - (3 -methylbenzyl)-2H-tetrazole;
5- [ i - (3,4 -dimethylphenyl)- 1 H -pyrazol -4-yl]-2- (3 -methy lbenzy l)-2H-tetrazole;
5- [i - (3,4 -dimethylphenyl)- 1 H -pyrazol -4-yl]-l - (3 -methylbenzyl)-2Hketrazole;
5- [·- (3,5 -dimethylphenyl)- 1 H -pyrazol -4-yl]-2- (3 -methy lbenzy l)-2H-tetrazole;
5- [ i - (3,5 -dimethylphenyl)- 1 H -pyrazol -4-yl]- l - (3 -methy lbenzy l)-2H-tetrazole;
5- 2-ethylphenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5- 2-ethylphenyl)- l H-pyrazol-4-yl]- l-(3-methylbenzyl)-2H-tetrazole; 5- 4-ethylphenyl)- lH-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5- 4-ethy lphenyl)- 1 H-pyrazol-4-yl]- 1 -(3-methylbenzy l)-2H-tetrazole;
197 1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y l]-2-(3-methy Ibenzy l)-2H-tetrazole;
1 -(4-methoxyphenyl)- 1 H-pyrazol-4-y I]- 1 -(3-methylbenzyl)-2H-tetrazole;
3-methylbenzyl)-5-[l -(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
3-methyIbenzyl)-5-[l-(2-methylphenyl)- l H-pyrazol-4-yl]-2H-tetrazole;
3-methylbenzyl)-5-[l -(4-methylphenyl)-lH-pyrazol-4-yl]-2H-tetrazole;
3-methy lbenzyl)-5-[l -(4-methylphenyl)- 1 H-pyrazol-4-yl]-2H-tetrazole;
5-chloro-l -methyl- l H-pyrazol-4-yl)-2-(3-methy Ibenzy l)-2H-tetrazole;
5-chloro- 1 -methyl- 1 H-pyrazol-4-yl)- 1 -(3-methylbenzy l)-2H-tetrazole;
5-chloro- 1 -ethyl- 1 H-pyrazol-4-yl)-2'-(3-methy Ibenzy l)-2H-tetrazole;
5-chloro- 1 -ethyl-l H-pyrazol-4-yl)- l -(3-methy lbenzyl)-2H-tetrazole;
5-chloro- l-(2-methylpropyl)-l H-pyrazol-4-yl]-2 -(3-methylbenzy l)-2H-tetrazole;
5-chloro-l -(2-methylpropyl)- lH-pyrazol-4-yl]-l -(3-methy Ibenzy l)-2H-tetrazoIe; l -benzyl-5-chloro- lH-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
l-benzyl-5-chloro-lH-pyrazol-4-yl)-l -(3-methylbenzyl)-2H-tetrazole;
5-chIoro- -pheny I- 1 H-pyrazol-4-y l)-2-(3-methy lbenzyl)-2H-tetrazole;
5-chloro- -phenyl-l H-pyrazol-4-yl)-l -(3-methylbenzyl)-2H-tetrazole;
5-chloro- -(2-chlorophenyI)- 1 H-pyrazol-4-yl]-2 3-methy Ibenzy l)-2H-tetrazole; 5-chloro- -(2-chlorophenyl)- 1 H-pyrazol-4-y 1]- 1 3-methy Ibenzy l)-2H-tetrazole; 5-chloro- -(3-chlorophenyl)- lH-pyrazol-4-yl]-2 3-methy Ibenzy l)-2H-tetrazole; 5-chloro- -(3-chlorophenyl)-l H-pyrazol-4-yl]-l 3-methylbenzy l)-2H-tetrazole; 5-chloro- -(4-chlorophenyl)- 1 H-pyrazol-4-y IJ-2 3-methylbenzy l)-2H-tetrazole; 5-chloro- -(4-chlorophenyl)- l H-pyrazol-4-yl]-l 3-methylbenzy l)-2H-tetrazole; 5-chloro- -(2,3-dichloropheny H -pyrazol -4-yl] -2- (3-methylbenzyl)-2H- -tetrazole 5-chloro- -(2,3-dichlorophenyP H ■pyrazol -4-yl] - 1 - (3-methylbenzyl)-2H -tetrazole 5-chloro- -(2,4-dichlorophenyP H -pyrazol -4-yl] -2- (3-methy Ibenzy 1)-2H- -tetrazole 5-chloro- -(2,4-dichloropheny H -pyrazol -4-yl] - 1 - (3-methylbenzyl)-2H -tetrazole 5-chloro- -(2,5-dichloropheny H -pyrazol -4-yl] -2- (3-methy Ibenzy 1)-2H -tetrazole 5-chloro- -(2,5-dichlorophenyl^ H -pyrazol -4-yl] - 1 - (3-methylbenzyl)-2H -tetrazole 5-chloro- -(2,6-dichloropheny H -pyrazol -4-yl] -2- (3-methy lbenzyl)-2H -tetrazole 5-chloro- -(2,6-dichlorophenyl' H -pyrazol -4-yl] - 1 - 3-methylbenzyl)-2H -tetrazole 5-chloro- -(3,4-dichlorophenyl^ H -pyrazol -4-yl] -2- 3-methy Ibenzy 1)-2H -tetrazole 5-chloro- -(3,4-dichlorophenyi; H- -pyrazol -4-yl] -1 - (3-methy lbenzyl)-2H- -tetrazole 5-chloro- -(3,5-dichlorophenyl^ H -pyrazol -4-yl] -2- 3-methylbenzyl)-2H -tetrazole
198 -chloro- l -(3,5-dichlorophenyl)-l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole;
-(2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
-(2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole;
-(3-bromophenyl)-5-chloro-l H-pyrazoI-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
•(3-bromophenyl)-5-chIoro- l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole;
■(4-bromophenyl)-5-chloro- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
■(4-bromophenyl)-5-chloro-l H-pyrazo!-4-yl]-l -(3-methylbenzyl)-2H-tetrazole;
-chloro- 4-fluorophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; -chloro- 4-fluorophenyl)-l H-pyrazol-4-yl]-l-(3-methylbenzyl)-2H-tetrazole; -chloro- 2-fluorophenyl)-l H-pyrazoI-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; -chloro- 2-fIuorophenyl)-l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole; •chloro- 2,3-dimethylphenyl)- 1 H- -pyrazol-4-y -2-(3-methylbenzyl)-2H-tetrazole -chloro- 2,3-dimethylphenyl)- 1 H ■pyrazol-4-ylj -l -(3-methylbenzyl)-2H-tetrazole -chloro- 2,4-dimethylphenyl)- 1H -pyrazol-4-yr -2-(3-methylbenzyl)-2H-tetrazole ■chloro- 2,4-dimethylphenyl)- I H -pyrazol-4-y - 1 -(3-methy Ibenzy l)-2H-tetrazole -chloro- 2,5-dimethylphenyl)- 1 H -pyrazol-4-y -2-(3-methylbenzyl)-2H-tetrazole -chloro 2,5-dimethyIphenyl)- 1 H •pyrazol-4-y - 1 -(3-methylbenzyl)-2H-tetrazole •chloro- 2,6-dimethylphenyl)- 1 H ■pyrazol-4-y -2-(3-methylbenzyl)-2H-tetrazole •chloro- 2,6-dimethylphenyl)- 1
Figure imgf000193_0001
-(3-methylbenzyl)-2H-tetrazole -chloro- 3,4-dimethylphenyl)- 1 H ■pyrazol-4-y ^2-(3-methy Ibenzy l)-2H-tetrazole -chloro- 3,4-dimethylphenyl)- LH ■pyrazol-4-yr - 1 -(3 -methy 1 benzy l)-2H-tetrazo le ■chloro- 3,5-dimethylphenyl)- 1 H -pyrazol-4-yT -2-(3-methylbenzyl)-2H-tetrazole -chloro- 3,5-dimethylphenyl)- 1H ■pyrazol-4-yl" - 1 -(3-methy lbenzyl)-2H-tetrazole -chloro- 2-ethylphenyl)-l H-pyrazol-4-y]]-2-(3-me thylbenzyl)-2H-tetrazole; -chloro- 2-ethylphenyl)-l H-pyrazol-4-yl]-l -(3-me thylbenzyl)-2H-tetrazole; -chloro- 4-ethylphenyl)-l H-pyrazol-4-yl]-2-(3-me thy Ibenzy l)-2H-tetrazole; ■chloro- 4-ethylphenyl)- 1 H-pyrazoI-4-y 1]- 1 -(3-me thy Ibenzy l)-2H-tetrazole; ■chloro- 4-methoxyphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; -chloro- 4-methoxyphenyl)- l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole; -chloro- 2-methylphenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; -chloro- 2-methylphenyl)- 1 H-pyrazol-4-y 1]- 1 -(3-methy Ibenzy l)-2H-tetrazole; •chloro- 4-methylphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; -chloro- 4-methy lphenyl)- 1 H-pyrazol-4-y I]- 1 -(3-methy Ibenzy l)-2H-tetrazole;
199 5- (5 -bromo l-methyl-lH-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5- (5 -bromo l -methyM H-pyrazol-4-yI)- l-(3-methylbenzyI)-2H-tetrazoIe;
5- (5 -bromo 1 -ethyl- 1 H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5- (5 -bromo 1 -ethyl- l H-pyrazol-4-yl)-l -(3-methylbenzyl)-2H-tetrazole;
5- [5 -bromo 1 -(2-methylpropyl)- H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H- tetrazole;
5- [5 -bromo 1 -(2-methylpropyl)- H-pyrazol-4-yl]-l -(3-methylbenzyl)-2H- tetrazole;
5- (1 -benzyl 5-bromo- 1 H-pyrazo -4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5- (1 -benzyl 5-bromd- 1 H-pyrazo -4-yl)-l -(3-methylbenzyl)-2H-tetrazole;
5- (5 -bromo phenyl- 1 H-pyrazo 4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5- (5 -bromo phenyl- 1 H-pyrazo 4-yl)-l -(3-methylbenzyl)-2H-tetrazole;
5- [5 -bromo 2-chlorophenyl)- H-pyrazol-4-yl]-2- 3-methylbenzyl)-2H- tetrazole;
5- [5 -bromo 2- chlorophenyl)- H-pyrazol-4-yl]- l - 3-methylbenzyl)-2H- tetrazole;
5- [5 -bromo 3- chlorophenyl)- H-pyrazol-4-yl]-2- 3-methylbenzyl)-2H- tetrazole;
5- [5 -bromo 3- chlorophenyl)- H-pyrazol-4-yl]-l - 3-methylbenzyl)-2H- tetrazole;
5- [5 -bromo 4- chlorophenyl)- H-pyrazol-4-yl]-2- 3-methylbenzyl)-2H- tetrazole;
5- [5 -bromo 4-chlorophenyl)- H-pyrazol-4-yl]-l - 3-methylbenzyl)-2H- tetrazole;
5- [5 -bromo 2,3-dichlorophenyl H-pyrazol-4-yl -2-(3-methylbenzyl)- 2H-tetrazole
5- [5 -bromo 2.3- dichlorophenyl H-pyrazol-4-yl -l -(3-methylbenzyl)- 2H-tetrazole
5- [5 -bromo 2.4- dichlorophenyl H-pyrazol-4-yl -2-(3-methylbenzyl)- 2H-tetrazole
5- [5 -bromo 2.4- dichlorophenyl H-pyrazol-4-yl - 1 -(3-methylbenzyl)- 2H-tetrazole
5- [5 -bromo 2.5- dichlorophenyl H-pyrazol-4-yI -2-(3-methyIbenzyI)- 2H-tetrazoIe
5- [5 -bromo- 2.5- dichlorophenyl H-pyrazol-4-yl -l'-(3-methylbenzyl)- 2H-tetrazole;
5- [5 -bromo 2.6- dichlorophenyl)-l H-pyrazol-4-yl -2 -"(3-methylbenzyl)- 2H-tetrazole;
5- [5 -bromo 2,6-dichlorophenyl)-l H-pyrazol-4-yl - 1 -(3-methy lbenzy 1)- 2H-tetrazole:
5- [5 -bromo 3,4-dichlorophenyl)- l H-pyrazol-4-yl -2-(3-methylbenzyl)- 2H-tetrazole:
5- [5. -bromo 3.4- dichlorophenyl)-l H-pyrazol-4-yl - 1 -(3-methylbenzyl)- 2H-tetrazole:
5- [5 -bromo 3.5- dichlorophenyl)-l H-pyrazol-4-yl -2-(3-methy lbenzy 1)- 2H-tetrazole:
5- [5 -bromo 3,5-dichlorophenyl)- 1 H-pyrazol-4-yl - 1 -(3-methylbenzy 1)- 2H-tetrazole:
5- [5 -bromo 2-bromophenyl)-l H-pyrazol-4-yl]-2- 3-methylbenzyl)-2H •tetrazole;
5- [5 -bromo 2- bromopheny 1)- 1 H-pyrazol-4-y 1]- 1 - 3-methylbenzyl)-2H •tetrazole;
5- [5 -bromo 3- bromophenyl)-l H-pyrazol-4-yl]-2- 3-methy lbenzyl)-2H •tetrazole;
5- [5 -bromo- 3- bromophenyl)- 1 H-pyrazol-4-yl]-l - 3-methy lbenzy 1)-2H tetrazole;
5- [5 -bromo- 4- bromophenyl)- 1 H-pyrazol-4-y l]-2 3-methylbenzy 1)-2H tetrazole;
200 5- ■bromo- 4-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -(3-methylbenzy l)-2H-tetrazole;
5-1 •bromo- 4-fluorophenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- ■bromo- 4-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -(3-methy Ibenzy l)-2H-tetrazole;
5- •bromo- 2-fluorophenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5· bromo- 2-fluoropheny 1)- 1 H-pyrazol-4-y I]- 1 -(3-methy Ibenzy l)-2H-tetrazole;
5- ■bromo- 2,3-dimethylphenyl)-l H-pyrazol-4-yl 3-methylbenzy l)-2H-tetrazole
5- ■bromo- 2.3- dimethylphenyl)-l H-pyrazol-4-yl 3-methy Ibenzy l)-2H-tetrazole
5- •bromo- 2.4- dimethylphenyl)-l H-pyrazol-4-yl 3-methylbenzyl)-2H-tetrazole
5- ■bromo- 2.4- dimethylphenyl)-l H-pyrazol-4-yl 3 -methy Ibenzy l)-2 H-tetrazo le
5-1 bromo- 2.5- dimethylphenyl)- 1 H-pyrazoI-4-y l]-2 3-methy!benzyI)-2H-tetrazoIe
5-1 bromo- 2.5- dimethylphenyl)-l H-pyrazol-4-yl 3 -methy Ibenzy l)-2H-tetrazole
5- bromo- 2.6- dimethylphenyl)-l H-pyrazol-4-yll-2→ 3-methy Ibenzy l)-2H-tetrazole
5- bromo- 2,6-dimethylphenyl)-l H-pyrazol-4-yll- l 3-methy Ibenzy l)-2H-tetrazole
5- bromo- 3,4-dimethylphenyl)-l H-pyrazol-4-yll-2 3-methy Ibenzy l)-2H-tetrazole
5- bromo- 3.4- dimethylphenyl)-l H-pyrazol-4-yll-l 3-methy Ibenzy l)-2H-tetrazole
5-1 bromo- 3.5- dimethylphenyl)-l H-pyrazol-4-yll-2 3 -methy Ibenzy l)-2H-tetrazole
5- bromo- 3,5-dimethylphenyl)- 1 H-pyrazol-4-yl 3-methy!benzyl)-2H-tetrazole
5- bromo- 2-ethylphenyl)-l H-pyrazol-4-yl]-2-(3-me hy Ibenzy l)-2H-tetrazole;
5- bromo- 2-ethylphenyl)- 1 H-pyrazol-4-yl]- 1 -(3-me hy Ibenzy l)-2H-tetrazole;
5- bromo- 4-ethylphenyl)- l H-pyrazol-4-yl]-2-(3-me hylbenzyl)-2H-tetrazole;
5- bromo- 4-ethylphenyl)- l H-pyrazol-4-yl]- l -(3-me hy Ibenzy l)-2H-tetrazole;
5- bromo- 4-methoxyphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5- bromo- 4-methoxyphenyl)-lH-pyrazol-4-yl]-l -(3-methylbenzyl)-2H-tetrazole;
5- bromo- 2-methylphenyl)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5· bromo- 2-methylphenyl)-l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole;
5-1 bromo- 4-methylphenyl)- l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
5-1 bromo- 4-methylpheny I)- l H-pyrazol-4-yl]-l -(3-methy Ibenzy l)-2H-tetrazole;
5- iodo- 1 - methyl- 1 H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5- iodo-1- methyl- l H-pyrazol-4-yl)-l -(3-methy lbenzyl)-2H-tetrazole;
5; ethyl-5- -iodo-lH-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5- ethyl-5 -iodo- l H-pyrazol-4-yl)-l -(3-methylbenzyl)-2H-tetrazole;
5- iodo-1 - (2-methylpropyl)-l H-pyrazol-4-yl].-2-(3-methy Ibenzy l)-2H-tetrazole; 5- iodo- 1 - (2-methylpropyl)- l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole;
201 5- benzyl-5-iodo- 1 H-pyrazol-4-yl)-2-(3-methy lbenzyl)-2H-tetrazole;
5- benzy 1-5-iodo- 1 H-pyrazol-4-y 1)- 1 -(3-methy lbenzy l)-2H-tetrazole;
5- iodo-l -phenyl-l H-pyrazol-4-yl)-2-(3-methylbenzyl)-2H-tetrazole;
5- iodo- 1 -phenyl- 1 H-pyrazol-4-y 1)- 1 -(3 -methylbenzyl)-2H-tetrazole;
5- 2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5- 2- chlorophenyl)-5-iodo-l H-pyrazol-4-yl]- l -(3-methylbenzyl)-2H-tetrazole; 5· 3- chlorophenyI)-5-iodo-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5- 3- chlorophenyl)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -(3-methylbenzyl)-2H-tetrazole;
5-1 4- chlorophenyl)-5-iodo- l H-pyrazoI-4-yl]-2-(3-methylbenzyI)-2H-tetrazole;
5-1 4-chlorophenyl)-5-iodo-lH-pyrazoI-4-yI]- l -(3-methylbenzyl)-2H-tetrazole;
■5- 2,3-dichlorophenyl)-5- odo- 1 H-pyrazol-4-y I -2-(3-methyIbenzyI)-2H-tetrazole
5- 2.3- dichlorophenyl)-5- odo-1 H-pyrazol-4-yl - 1 -(3-methy lbenzy l)-2H-tetrazole
5- 2.4- dichlorophenyl)-5- odo-l H-pyrazol-4-yl -2-(3 -methy lbenzy l)-2 H-tetrazole
5- 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl -1 -(3-methy lbenzyl)-2H-tetrazole
5- 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl -2-(3-methylbenzyl)-2H-tetrazoIe
5- 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl - 1 -(3-methylbenzyl)-2H-tetrazole
5- 2.6- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -2-(3-methy lbenzy l)-2 H-tetrazole
5- 2,6-dichlorophenyl)-5- odo- 1 H-pyrazol-4-yl - l -(3-methylbenzyl)-2H-tetrazole
5- 3,4-dichlorophenyl)-5- odo- 1 H -pyrazo 1-4-y I -2-(3-methy lbenzy l)-2H-tetrazole
5- 3.4- dichlorophenyl)-5- do-1 H-pyrazol-4-yl -1 -(3-methy Ibenzyl)-2H-tetrazole
5- 3.5- dichlorophenyl)-5- odo- H-pyrazol-4-y 1 -2-(3-methy lbenzy l)-2H-tetrazole
5-1 3,5-dichlorophenyl)-5- odo-1 H-pyrazol-4-yl -1 -(3-methy 1 benzy l)-2 H-tetrazole
5- 2-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2- 3-methy lbenzyl)-2H-tetrazole;
5- 2- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-l - 3-methylbenzyl)-2H-tetrazole;
5- 3- bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2- 3-methylbenzyl)-2H-tetrazole;
5- 3- bromopheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 - 3-methy lbenzy l)-2H-tetrazole;
5- 4- bromopheny l)-5-iodo- 1 H-pyrazoI-4-y l]-2- 3-methy lbenzy l)-2H-tetrazole;
5- 4-bromophenyI)-5-iodo-l H-pyrazoI-4-yl]-l - 3-methy lbenzy l)-2H-tetrazole;
5- 4-fluorophenyl)-5-iodo-l H-pyrazoI-4-yI]-2 3-methy lbenzy l)-2H-tetrazole;
5- 4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-l 3-methy lbenzy l)-2H-tetrazole;
5- 2-fluorophenyl)-5-iodo- 1 H-pyrazol-4-yl]-2 3-methylbenzyl)-2H-tetrazole;
5- 2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-l 3-methylbenzyl)-2H-tetrazole;
5- 2,3-dimethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole;
202 I -(2,3-dimethyIpheny l)-5-iodo- l H-pyrazol -4-yl] - 1 - 3-methylbenzyl)-2H-tetrazole l -(2,4-dimethylphenyl)-5-iodo-l H-pyrazol -4-yl] -2- 3-methy lbenzy l)-2 H-tetrazole l -(2,4-dimethylphenyl)-5-iodo-l H-pyrazol -4-yl] - 1 - (3-methy lbenzy l)-2 H-tetrazole l -(2,5-dimethylphenyl)-5-iodo-lH-pyrazol- -4-yl] -2- (3-methy lbenzyl)-2H-tetrazole l -(2,5-dimethylphenyl)-5-iodo-l H-pyrazol -4-yl] -1 - (3-methylbenzyl)-2H-tetrazole l -(2,6-dimethylphenyl)-5-iodo-lH-pyrazol- -4-yl] -2- (3-methy lbenzyl)-2H-tetrazoIe
1 -(2,6-dimet y lpheny l)-5-iodo- 1 H-pyrazol- -4-yl] - 1 - (3-methy lbenzyl)-2 H-tetrazole
1 -(3,4-dimethylphenyl)-5-iodo- 1 H-pyrazol- -4-yl] -2- (3-methylbenzyl)-2H-tetrazole
] -(3,4-dimethylphenyl)-5-iodo- l H-pyrazol -4-yl] - 1 - 3-ijiethy lbenzy l)-2H-tetrazole
1 -(3,5-dimethylphenyl)-5-iodo-l H-pyrazol- -4-yl] -2- (3-methy lbenzy l)-2 H-tetrazole
1 -(3,5-dimethy lphenyI)-5-iodo- 1 H-pyrazol- -4-yl] - 1 - 3-methy lbenzyl)-2 H-tetrazole l -(2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]- •2-(3- me thy 1 benzy l)-2 H -tetrazole ; l -(2-ethylphenyl)-5-iodo-lH-pyrazol-4-yl]- l -(3-me thy lbenzy l)-2H-tetrazole; l -(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]- 2-(3- me thylbenzyl)-2H-tetrazole; l -(4-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]- -l -(3- me thy lbenzy l)-2H-tetrazole;
5-iodo- l -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2-(3-methy lbenzy l)-2H-tetrazole; 5-iodo-l -(4-methoxyphenyl)- l H-pyrazol-4-yl]- l -(3-methy lbenzy l)-2H-tetrazole; 5-iodo- l-(2-methylphenyl)-l H-pyrazol-4-yl]-2-(3-methy lbenzy l)-2H-tetrazole; "5-iodo- 1 -(2-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -(3-methylbenzyl)-2H-tetrazoIe; 5-iodo- l -(4-methylphenyI)-l H-pyrazol-4-yl]-2-(3-methylbenzyl)-2H-tetrazole; 5-iodo- 1 -(4-methy lpheny 1)- 1 H-pyrazol-4-y I]- 1 -(3-methylbenzy l)-2H-tetrazole; Ί -methyl- 1 H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
[ 1 -methyl- 1 H-pyrazol-4-y 1)- 1 -(4-nitrobenzyl)-2H-tetrazole;
Ί -ethyl- l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
l -ethyl-l H-pyrazol-4-yl)-l -(4-nitrobenzyl)-2H-tetrazole;
l -(2-methylpropyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
1 -(2-methy lpropyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;
\ -benzyl- l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
1 -benzyl- 1 H-pyrazol-4-yl)- 1 -(4-nitrobenzyl)-2H-tetrazole;
(4-nitrobenzyl)-5-( 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
4-nitrobenzyl)-5-( 1 -phenyl- 1 H-pyrazol-4-yl)-2H-tetrazole;
l -(2-chlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
( 1 -(2-chIoropheny I)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;
203 5- [i- (3-chIorophenyl)-lH-pyrazol-4-yl]-2- '4-nitrobenzy l)-2H-tetrazole;
5- [i- (3-chlorophenyl)-l H-pyrazol-4-yl]- 1 - 4-nitrobenzy l)-2H-tetrazole;
5- [i- (4-chlorophenyl)-lH-pyrazol-4-yl]-2- 4-nitrobenzy l)~2H-tetrazole;
5- [i- (4-chlorophenyI)- 1 H-pyrazol-4-yl]- 1 - (4-riitrobenzyl)-2H-tetrazole;
5- [i- (2,3-dichlorophenyl)- 1 H-pyrazol-4-yl |-2-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (2,3-dichlorophenyl)-lH-pyrazol-4-yl |-l-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (2,4-dichlorophenyl)-lH-pyrazol-4-yI |-2-(4-nitrobenzyl)-2H-tetrazole;
5- i- (2,4-dichlorophenyl)- 1 H-pyrazol-4-yl |- 1 -(4-nitrobenzyl)-2H-tetrazole;
5- [i- (2,5-dichlorophenyl)-lH-pyrazol-4-yl |-2-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (2,5-dichlorophenyl)-lH-pyrazol-4-yl |- 1 -(4-nitrobenzy l)-2H-tetrazole;
5- [1- (2,6-dichlorophenyl)- 1 H-pyrazol-4-yl |-2-(4-nitrobenzyl)-2H-tetrazole;
5- [i- (2,6-dichlorophenyl)-lH-pyrazol-4-yl -1 -(4-nitrobenzy l)-2H-tetrazole;
5- ;ι- (3,4-dichlorophenyl)-lH-pyrazoi-4-yl -2-(4-nitrobenzyl)-2H-tetrazole;
5- Ί- (3,4-dichlorophenyl)-lH-pyrazol-4-yl - 1 -(4-nitrobenzy l)-2H-tetrazole;
5- Ί- (3,5-dichlorophenyl)-l H-pyrazol-4-yl -2-(4-n itrobenzy l)-2H -tetrazole;
5- ;i- (3,5-dichlorophenyl)-l H-pyrazol-4-yl - 1 -(4-nitrobenzy l)-2H-tetrazole;
5- L'- (2-bromophenyl)- 1 H-pyrazol-4-y l]-2- (4-nitrobenzyl)-2H-tetrazole;
5- [1- (2-bromophenyl)- 1 H-pyrazol-4-yl]- 1 - ^4-nitrobenzyl)-2H-tetrazole;
5- ;i- (3-bromophenyl)-lH-pyrazol-4-yl]-2- -nitrobenzyl)-2H-tetrazole;
5- ;i- (3-bromopheny I)- 1 H-pyrazol-4-y 1]- 1 - (4-nitrobenzyl)-2H-tetrazole;
5- 1- 4-bromopheny 1)- 1 H-pyrazol-4-yl]-2- (4-nitrobenzyl)-2H-tetrazole;
5- (4-bromopheny 1)- 1 H-pyrazol-4-yl]- 1 - 4-nitrobenzyl)-2H-tetrazole;
5- ^-fluorophenyl)- 1 H-pyrazoI-4-yl]-2-( 4-nitrobenzy l)-2H-tetrazole;
5- ;i- (4-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -( 4-nitrobenzyl)-2H-tetrazole;
5- 1- (2 -fluorophenyl)- 1 H-pyrazol-4-yl]-2-( 4-nitrobenzy l)-2H-tetrazole;
5- 1- ^-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -( 4-nitrobenzy l)-2H-tetrazole;
5- 1- (2,3-dimethylphenyl)-lH-pyrazol-4-y ]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 1- (2,3-dimethylphenyl)-lH-pyrazol-4-y ]-l-(4-nitrobenzyl)-2H-tetrazole;
5- (2,4-dimethylpheny 1)- 1 H-pyrazol-4-y ]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 1- ^2,4-dimethylpheny 1)- 1 H-pyrazol-4-y ]-l-(4-nitrobenzyl)-2H-tetrazole;
5- 1- (2,5-dimethylphenyl)-lH-pyrazol-4-y ]-2-(4-nitrobenzyl)-2H-tetrazole;
5- ;i- (2,5-dimethylphenyl)- 1 H-pyrazol-4-y ]^1 -(4-nitrobenzy l)-2H-tetrazole;
5- ;i- ,6-dimethylphenyl)-lH-pyrazol-4-y ]-2-(4-nitrobenzyl)-2H-tetrazole;
204 5· -(2,6-dimethylphenyl)-lH:pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5· -(3,4-dimethylphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5· -(3,4-dimethylphenyl)- l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5-1 -(3,5-dimethylphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- -(3, 5-dimethy (phenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;
5- -(2-ethylphenyl)- lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- -(2-ethylphenyl)- 1 H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5- -(4-ethylphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- -(4-ethylphenyl)- l H-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5- -(4-methoxyphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5· -(4-methoxyphenyl)- 1 H-pyrazol-4-y I]- l -(4-nitrobenzyl)-2H-tetrazole;
5· -(2-methylphenyl)- 1 H-pyrazol-4-yl]-2-(4-nitrobenzy l)-2H-tetr'azole;
5- -(2-methy lphenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzy l)-2H-tetrazole;
5- -(4-methylphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazoIe;
■5-1 -(4-methylphenyl)-l H-pyrazol-4-yl]-l -(4-nitrobenzy l)-2H-tetrazole;
5-( -chloro-1 -methyl- 1 H-pyrazol-4-y l)-2-(4-nitrobenzy l)-2H-tetrazole;
5-( -chloro- 1 -methyl- 1 H-pyrazol-4-y 1)- 1 -(4-nitrobenzy l)-2H-tetrazole;
5· -chloro- 1 -ethyl- l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5· -chloro-1 -ethyl- l H-pyrazol-4-yl)-l -(4-nitrobenzyl)-2H-tetrazole;
■5· -chloro-1 -(2-methylpropyl)- H-pyrazol-4-yl]-2 -(4-nitrobenzy l)-2H-tetrazole;
5- -chloro- 1 -(2-methylpropyl)- H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole;
5- -benzyl-5-chIoro-lH-pyrazo -4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5· -benzyl-5-chloro- 1 H-pyrazo -4-y 1)- 1 -(4-nitrobenzy l)-2H-tetrazole;
5· -chloro- 1 -phenyl- 1 H-pyrazo -4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5· -chloro-1 -phenyl- 1 H-pyrazo -4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5- -chloro-1 -(2-chlorophenyl)- H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5· -chloro-l -(2-chlorophenyl)- H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole;
5- -chloro-l -(3-chlorophenyl)- H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5· -chloro- l-(3-chlorophenyl)- H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5- -chloro- 1 -(4-chlorophenyl)- H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- -chloro- 1 -(4-chlorophenyl)- H-pyrazol-4-yl]-l -(4-nitrobenzy l)-2H-tetrazole;
5- -chloro-1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-y l]-2-(4-nitrobenzy l)-2H-tetrazole;
5- -chloro- 1 -(2,3-dichlorophenyl)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzy l)-2H-tetrazole;
205 ■chloro-l -(2,4-dichlorophenyl H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole ■chloro-l-(2,4-dichlorophenyl H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole -ch loro- 1 -(2, 5 -dich loropheny 1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole -chloro- 1 -(2,5-dichlorophenyl H-pyrazol-4-yl]-l -(4-n itrobenzy l)-2H-tetrazole -chloro- 1 -(2,6-dichloropheny 1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole •chloro- 1 -(2,6-dichloropheny I H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole -chloro- l -(3,4-dichlorophenyl H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole •chloro- 1 -(3, 4-dichlorophenyl H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole ■chloro- 1 -(3, 5-dichlorophenyl H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole -chloro-l -(3,5-dichlorophenyl H-pyrazol-4-yl]- l-(4-nitrobenzyl)-2H-tetrazole (2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; (2-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole; (3-bromophenyl)-5-chloro-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; (3-bromophenyl)-5-chloro- l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole; (4-bromophenyl)-5-chloro- lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; (4-bromophenyl)-5-chloro- l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole; chloro- 4-fluorophenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; chloro- 4-fluorophenyl)-l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole; chloro- 2-fluorophenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; chloro- 2-fluorophenyl)- 1 H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole; chloro- 2,3-d methylphenyl H-pyrazol-4-yl]-2-(4 nitrobenzyl)-2H-tetrazole chloro- 2.3- d methylphenyl H-pyrazoI-4-yl]- l-(4 nitrobenzyl)-2H-tetrazole chloro- 2.4- d methylphenyl H-pyrazol-4-yl]-2-(4 n itrobenzy l)-2H-tetrazo le chloro- 2.4- d methylphenyl H-pyrazol-4-yl]- l -(4 nitrobenzyl)-2H-tetrazole chloro- 2.5- d methylphenyl H-pyrazol-4-yl]-2-(4 nitrobenzyl)-2H-tetrazole chloro- 2.5- d methylphenyl -l H-pyrazol-4-yl]-l -(4 nitrobenzyl)-2H-tetrazole chloro- 2.6- d methylphenyl -l H-pyrazol-4-yl]-2-(4 n itrobenzy l)-2 H-tetrazole chloro- 2,6-d methylphenyl -l H-pyrazol-4-yl]-l -(4 nitrobenzyl)-2H-tetrazole chloro- 3,4-d methylphenyl -l H-pyrazol-4-yl]-2-(4 nitrobenzyl)-2H-tetrazole chloro- 3.4- d methylphenyl -lH-pyrazol-4-yl]- l -(4 nitrobenzyl)-2H-tetrazole chloro- 3.5- d methylphenyl - l H-pyrazol-4-yl]-2-(4 n itrobenzy l)-2 H-tetrazo le chloro- 3,5-d methylphenyl - l H-pyrazol-4-yl]- l -(4 nitrobenzyl)-2H-tetrazole chloro- 2-ethylphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
206 5- [5 -chloro- 1■(2-ethylpheny 1)- 1 H-pyrazol-4-y I]- 1 -(4-nitrobenzyl)-2H-tetrazole;
5- [5 -chloro- 1 ■(4-ethylphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -chloro-1 (4-ethylphenyl)-l H-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -chloro-1 (4-methoxyphenyl-)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -chloro-1 (4-methoxyphenyl).-lH-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole;
5- [5 -chloro-1 (2-methylphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -chloro- 1 (2-methylphenyl)-l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5- [5 -chloro-1 (4-methylphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -chloro- 1 (4-methylphenyl)-l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole;
5- (5 -bromo-1 ■methyl- l H-pyrazol-4-yl)-2-(4-riitrobenzyl)-2H-tetrazole;
5- (5 -bromo-1 •methyl- l H-pyrazol-4-yl)-l -(4-nitrobenzyl)-2H-tetrazole;
5- (5 -bromo-1 ■eth l- 1 H-pyrazol-4-y l)-2-(4-nitrobenzy l)-2H-tetrazole;
5- (5 -bromo-1 -ethyl-1 H-pyrazol-4-yl)-l -(4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 ■(2-methylpropyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo- 1 •(2-methy lpropyl)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzyl)-2H-tetrazole;
5- ( 1 -benzyl-5 -bromo-1 H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5- ( 1 -benzyl-5 -bromo-1 H-pyrazol-4-yl)-l -(4-nitrobenzyl)-2H-tetrazole;
5- (5 -bromo- 1 •phenyl- 1 H-pyrazol-4-y l)-2-(4-nitrobenzy l)-2H-tetrazole;
5- (5 -bromo-1 -phenyl- l H-pyrazol-4-yl)-l -(4initrobenzyl)-2H-tetrazole;
5- [5 -bromo- 1 (2-chlorophenyl)-l H-pyrazol-4-yl]-2 4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 (2-chlorophenyl)-l H-pyrazol-4-yl]- l 4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 (3-chlorophenyl)-l H-pyrazol-4-yl]-2 4-n itrobenzy l)-2 H-tetrazo le ;
5- [5 -bromo-1 (3-chlorophenyl)-l H-pyrazol-4-yl]- 1 4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 (4-chloropheny 1)- 1 H-pyrazol-4-y l]-2 4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 (4-chlorophenyl)-l H-pyrazol-4-yl]- l 4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo- 1 (2,3-dichlorophenyl)-l H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo- 1 (2,3-dichlorophenyl)- 1 H-pyrazol-4-yl - l -(4rnitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 (2,4-dichlorophenyl)- l H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 (2,4-dichlorophenyl)- 1 H-pyrazol-4-y 1 -l -(4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 (2,5-dichlorophenyl)-l H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 (2,5-dichlorophenyl)-l H-pyrazol-4-yl -l-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo-1 (2,6-dichlorophenyl)- lH-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole;
5- [5 -bromo- 1 (2,6-dichlorophenyl)-l H-pyrazol-4-yl -l -(4-nitrobenzyl)-2H-tetrazole;
207 -[5-bromo-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(3,4-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(3,5-dichlorophenyI)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(3,5-dichlorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(2-bromophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo- 1 -(2-bromopheny I)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzyl)-2H-tetrazole;-[5-bromo- 1 -(3-bromopheny 1)- 1 H-pyrazol-4-y l]-2-(4-nitrobenzy l)-2H-tetrazole;-[5-bromo- 1 -(3-bromophenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(4-bromophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(4-bromophenyI)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(4-fluorophenyl)-lH-pyrazoI-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(4-fluorophenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(2-fluorophenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo- 1 -(2-fluorophenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(2,3-dimethylphenyl)-lH-pyrazoI-4-yI]-2-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(2,3-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzy])-2H-tetrazole-[5-brorno-l-(2,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(2,5-dimethylphenyl)-lH-pyrazol-4-yl]-i-(4-nitrobenzyl)-2H-tetrazole-[5-brpmo-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(2,6-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(3,4-dimethylphenyl)-l H-pyrazol-4-yI]-2-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(3,4-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(3,5-dimethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole-[5-bromo-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-2-(4-nitrobenzyI)-2H-tetrazole;-[5-bromo-l-(2-ethylphenyl)-lH-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazoIe;-[5-bromo- 1 -(4-ethylphenyl)- 1 H-pyrazol-4-y l]-2-(4-nitrobenzy l)-2H-tetrazole;-[5-bromo- 1 -(4-ethy Ipheny 1)- 1 H-pyrazol-4-y 1]- 1 -(4-nitrobenzy l)-2H-tetrazole;-[5-bromo-l-(4-methoxyphenyI)-lH-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;-[5-bromo-l-(4-methoxyphenyl)-lH-pyrazol-4-yl]-l -(4-nitrobenzy l)-2H-tetrazole;-[5-bromo- 1 -(2-methy Iphenyl)- 1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
208 5- 5-bromo-l -(2-methylphenyl)-l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole;
5- 5-bromo- l -(4-methylphenyl)- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5· 5-bromo- 1 -(4-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazole;
5- 5-iodo- l -methyl- l H-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5- 5-iodo- 1 -methyl- 1 H-pyrazol-4-yl)- 1 -(4-nitrobenzy l)-2H-tetrazole;
5- l-ethyl-5-iodo-lH-pyrazol-4-yl)-2-(4-nitrobenzyl)-2H-tetrazole;
5- l -ethyl-5-iodo-l H-pyrazol-4-yl)-l -(4-nitrobenzy l)-2H-tetrazole;
5- 5-iodo- 1 -(2-methylpropyl)- 1 H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- ■iodo-l -(2-methylpropyl)-l H-pyrazol-4-yl]- l -(4-nitrobenzy l)-2H-tetrazole;
5- l -benzyl-5-iodo-l H-pyrazol-4-yl)-2 -(4-nitrobenzy l)-2H-tetrazole;
5- 1 -benzy 1-5-iodo- 1 H-pyrazol-4-yl)- 1 -(4-nitrobenzy l)-2H-tetrazole;
5- 5-iodo- 1 -phenyl- 1 H-pyrazol-4-yl)-2-(4-nitrobenzy l)-2H-tetrazole;
5- 5-iodo- 1 -phenyl- 1 H-pyrazol-4-y 1)- 1 -(4-nitrobenzy l)-2H-tetrazole;
5- 1 - 2-chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2 4-nitrobenzy l)-2H-tetrazole;
5- 2- chlorophenyl)-5-iodo- l H-pyrazol-4-yl]-l 4-nitrobenzy l)-2H-tetrazole;
5- 3- chlorophenyl)-5-iodo-l H-pyrazol-4-yl]-2- 4-nitrobenzyl)-2H-tetrazole;
5- 3- chloropheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 -< 4-nitrobenzy l)-2H-tetrazole;
5- 4- chlorophenyl)-5-iOdo-l H-pyrazol-4-yl]-2- 4-nitrobenzy l)-2H-tetrazole;
5- 4-chloropheny I)-5-iodo- 1 H-pyrazol-4-yl]- 1 - 4-nitrobenzyl)-2H-tetrazole;
5-1 2,3-dichlorophenyl)-5- odo-lH-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5- 2.3- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -l -(4-nitrobenzyl)-2H-tetrazole
5· 2.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -2-(4-nitrobenzyl)-2H-tetrazole
5- 2.4- dichlorophenyl)-5- odo-1 H-pyrazol-4-yl -1 -(4-nitrobenzy l)-2H-tetrazole
5-1 2.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y I -2-(4-nitrobenzyl)-2H-tetrazole
5- 2.5- dichlorophenyl)-5- odo-1 H-pyrazol-4-yl 1 -(4-nitrobenzyl)-2H-tetrazole
5- 2.6- dichlorophenyl)-5- odo-l H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5- 2,6-dichlorophenyl)-5- odo-l H-pyrazol-4-yl - 1 -(4-nitrobenzyl)-2H-tetrazole
5- 3,4-dichlorophenyl)-5- odo-1 H-pyrazol-4-yl -2-(4-nitrobenzyl)-2H-tetrazole
5- 3.4- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 - 1 -(4-nitrobenzyl)-2H-tetrazole
5- 3.5- dichlorophenyl)-5- odo- 1 H-pyrazol-4-y 1 -2-(4-nitrobenzyl)-2H-tetrazole
5- 3,5-dichlorophenyl)-5 odo- 1 H-pyrazol-4-y 1 - 1 -(4-nitrobenzyl)-2H-tetrazole
5· 2-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-2 4-nitrobenzyl)-2H-tetrazole;
5- 2-bromopheny l)-5-iodo- 1 H-pyrazol-4-y 1]- 1 4-nitrobenzy l)-2H-tetrazole;
209 5- 3-bromophenyl)-5-iodo- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 3- bromophenyl)-5-iodo- l H-pyrazol-4-yl]-l-(4-nitrobenzyl)-2H-tetrazole;
5- 4- bromophenyl)-5-iodo- l H-pyrazol-4-yl]-2-(4-nitfobenzyl)-2H-tetrazole;
5- 4-bromophenyl)-5-iodo-l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5- 4-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-1 4-fluorophenyI)-5-iodo- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzyl)-2H-tetrazoIe;
5- 2-fluorophenyl)-5-iodo-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5-! 2-fluorophenyl)-5-iodo- l H-pyrazoi-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5- 2,3-dimethylphenyl)-5- odo- 1 H -pyrazol-4- -yl] -2- (4- -nitrobenzyl) -2H -tetrazole 5- 2.3- dimethylphenyl)-5- odo- I H -pyrazol-4 -yl] -1 - (4 -nitrobenzyl) -2H -tetrazole 5- 2.4- dimethylphenyl)-5- odo- 1 H -pyrazol-4 -yl] -2- (4 -nitrobenzyl) -2H -tetrazole 5- 2.4- dimethylphenyl)-5- odo- I H ■pyrazol-4- -yl] -1 - (4- -nitrobenzyl)- -2H -tetrazole 5- 2.5- dimethylphenyl)-5- odo- I H ■pyrazol-4- -yl] -2- (4- -nitrobenzyl)- -2H -tetrazole 5·- 2.5- dimethylphenyl)-5- odo- I H -pyrazol-4 -yl] -1 - (4- -nitrobenzyl) -2H -tetrazole 5- 2.6- dimethylphenyl)-5- odo- I H ■pyrazol-4- -yl] -2- (4- -nitrobenzyl) -2H -tetrazole 5- 2,6-dimethylphenyl)-5- odo- I H -pyrazoI-4- -yl] - 1 - (4- -nitrobenzyl)- -2H -tetrazole 5- 3,4-dimethylphenyl)-5- odo- I H •pyrazol-4- -yl] -2- (4- -nitrobenzyl) -2H -tetrazole 5- 3.4- dimethylphenyl)-5- odo- I H -pyrazol-4- -yl] - 1 - (4- -nitrobenzyl) -2H -tetrazole 5- 3.5- dimethylphenyl)-5- odo- 1 H- -pyrazol-4- -yl] -2- (4- -nitrobenzyl)- -2H -tetrazole 5- 3,5-dimethylphenyl)-5- odo- 1 H -pyrazol-4- -yl] -1 - (4- -nitrobenzyl) -2H -tetrazole 5- 2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 2-ethylphenyl)-5-iodo-l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5- 4-ethylphenyl)-5-iodo- l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- 4-ethylphenyl)-5-iodo- l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole;
5- iodo- l -(4-methoxyphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- iodo- l -(4-methoxyphenyl)- l H-pyrazol-4-yl]- l -(4-nitrobenzyl)-2H-tetrazole;
5- iodo-l -(2-methylphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole;
5- iodo-l-(2-methylphenyl)- l H-pyrazol-4-yl]-l -(4-nitrobenzyl)-2H-tetrazole;
5- iodo-l -(4-methylphenyl)-l H-pyrazol-4-yl]-2-(4-nitrobenzyl)-2H-tetrazole; or 5-. iodo- 1 -(4-methylphenyl)- 1 H-pyrazol-4-yl]- 1 -(4-nitrobenzy l)-2H-tetrazole.
7. A process for preparing a compound of formula I, its derivatives, salts, stereo-isomers or regio-isomers thereof,
210
Figure imgf000205_0001
Formula 1
wherein:
R] is selected from H, CI, Br or I;
R2 is selected from hydrogen or a straight chain or a branched C| -7 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, 1, N02, CN, C1 -5 alkyl, phenyl, or a CrC4 alkoxy;
R3 is selected from a straight or a branched chain C ] _7 alkyl; or a C6-C 14 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, 1, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C1 -5 alkyl, phenyl, or a C 1 -C4 alkoxy;
said process comprising:
Figure imgf000205_0002
treating a compound of formula II with a reagent and. an organic solvent selected from N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methyl-2- pyrrolidone, acetonitri le, acetone, dichlorofnethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran, toluene, xylene, benzene or water to obtain a compound of formula I with R2 as hydrogen, its derivatives, salts, stereo-isomers, or regio-isomers thereof; wherein,
Ri is selected from H, CI, Br or 1;
R3 is selected from a straight or a branched chain C i - alkyl; or a C6-Ci4 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from
211 CI, Br, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C1.5 alkyl, phenyl, or a C1 -C4 alkoxy; and
said reagent is selected from an optionally substituted sodium azide in the presence of either an ammonium halide such as ammonium chloride, ammonium bromide or ammonium iodide or a tri-n-butyl tin halide such as tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide; and
optionally alkylating the above compound of formula I with a dialkyl sulfate or alkali halide such as methyl iodide or methyl bromide, in presence of a base selected from an alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or Ν,Ν-dimethylaniline, to obtain a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, wherein R2 is selected from a straight chain or a branched Ci-7 alkyl.
8. The process as claimed in claim 7, said process comprising:
treating a compound of formula II with an optionally substituted sodium azide in the presence of either an ammonium halide such as ammonium chloride, ammonium bromide or ammonium iodide, and a polar solvent selected from N,N- dimethylformamide, N,N-dimethylacetamide, N-rhethyl-2-pyrrolidone or water; or a tri-n-butyl tin halide such as tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri- n-butyl tin iodide in presence of a non polar solvent such as toluene, xylene or benzene, to obtain a compound of formula I, wherein R2 is hydrogen.
9. The process as claimed in claim 7, comprising:
Figure imgf000206_0001
Formula III
treating a compound of formula III with sodium nitrite and cuprous halide selected from cuprous chloride, cuprous bromide or cuprous iodide, with a mineral
212 I acid selected from hydrochloric acid, hydrobromic acid, or sulfuric acid, to obtain a compound of formula II; wherein
R3 is selected from a straight or a branched chain C|_7 alkyl; or a C6-C|4 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; >.
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, 1, C|_5 alkyl, phenyl, or a G C4 alkoxy; and
treating the compound of formula II with a. substituted sodium azide in the presence of either an ammonium halide such as ammonium chloride, ammonium bromide or ammonium iodide; and a polar solvent selected from N,N- dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, or water, or a tri-n-butyl tin halide such as tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri- n-butyl tin iodide in presence of a non polar solvent such as toluene, xylene or benzene, to obtain the compound of formula I, its derivatives, salts, stereo-isomers, regio-isomers thereof, wherein R2 is hydrogen.
The process as claimed in claim 7, comprising:
treating malononitrile with a compound of formula V in presence of acetic anh
Figure imgf000207_0001
Formula V, Formula IV wherein ¾ is independently selected from a straight or a branched C alkyl; treating the compound of formula IV with an optionally substituted N-alkyl hydrazine sulfate, or an optionally substituted N-alkyl hydrazine, or an optionally substituted N-aryl hydrazine sulfate, or an optionally substituted N-aryl hydrazine, and a base selected from an alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl
213 amine, pyridine, pyrrolidine or .N,N-dimethylaniline, in the presence of an alcohol selected from methanol, ethanol Or propanol to obtain a compound of formula HI,
Figure imgf000208_0001
Formula 111
wherein R3 is selected from a straight chain or a branched chain C 1 alkyl or a C6 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more phenyl group; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, Ci -2 alkyl, phenyl or Q -C4 alkoxy;
treating the compound of formula III with sodium nitrite and cuprous halide selected from cuprous chloride, cuprous bromide or cuprous iodide, with a mineral acid selected from hydrochloric acid, hydrobromic acid, or sulfuric acid, to obtain a compound of formula II;
treating the compound of formula I I with sodium azide in the presence of either an ammonium halide selected from ammonium chloride, ammonium brom ide or ammonium iodide; and a polar solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, or water, or a tri-n-butyl tin halide such as tri-n-butyl tin chloride, tri-n-butyl tin bromide or tri-n-butyl tin iodide in presence of a non polar solvent such as toluene, xylene or benzene, to obtain a compound of formula I, its derivatives, salts, stereo-isomers, regio-isomers thereof wherein R2 is hydrogen.
process as claimed in claim 7, said process comprising:
treating a compound of formula II with an optional ly substituted sodium azide in the presence of either an ammonium hal ide such as ammonium chloride, ammonium bromide or ammonium iodide, and a polar solvent selected from N,N- dimethylformamide, N,N-dimethylacetam ide, N-methyl-2-pyrrolidone, or water; or a tri-n-butyl tin halide such as tri-n-butyl tin chloride, tri-n-butyl tin brom ide or tri- n-butyl tin iodide in presence of a non polar solvent such as toluene, xylene or benzene, to obtain a compound of formula I wherein R2 is hydrogen; and
214 alkylating the above compound of formula I with a dialkyl sulfate, or alkyl halide such as methyl iodide or methyl bromide in presence of a base selected from an alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or Ν,Ν-dimethylaniline, in the presence of a polar solvent N,N- dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran or water, to obtain a compound of formula I wherein R2 is selected from a straight chain or a branched C alkyl.
12. The process as claimed in claim 10, further comprising:
alkylating a compound of formula I wherein R2 is hydrogen with dialkyl sulfate or alkyl halide such as methyl iodide or methyl bromide and a base selected from an alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or an organic base such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or N,N-dimethylaniline, in the presence of a polar solvent N,N- dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1,2-dichloroethane, methanol, tetrahydrofuran or water, to obtain a compound of formula I wherein R2 is a straight chain or a branched C|-7 alkyl.
13. The process as claimed in claim 7, said process comprising:
treating 5-chloro- l -methyl- l H-pyrazole-4-carbonitrile compound with sodium azide in the presence of either ammonium chloride, and N,N- dimethylformamide, or tri-n-butyl tin chloride and toluene to obtain 5-(5-chloro- l - methyl-lH-pyrazol-4-yl)-2H-tetrazole) of formula I, wherein R2 is Η.
14. The process as claimed in claim 7, said process comprising:
treating 5-chloro- l -methyl-lH-pyrazole-4-carbonitrile compound with sodium azide in the presence of either ammonium chloride, and N,N- dimethylformamide; or tri-n-butyl tin chloride and toluene to obtain 5-(5-chloro- l - methyl- l H-pyrazol-4-yl)-2H-tetrazole of formula I; wherein R2 is hydrogen; and
215 methylating 5-(5-chloro-l -methyl-lH-pyrazol-4-yl)-2H-tetrazole) of formula I; wherein R2 is hydrogen; with dimethyl sulfate and potassium carbonate in the presence of acetone, to obtain 5-(5-chloro- l -methyl- l H-pyrazol-4-y l)-2-methyl-2H- tetrazole of formula I; wherein R2 is a methyl.
15. A process for preparing a compound of formula I, its derivatives, salts, stereo-isomers or regio-isomers thereof,
Figure imgf000210_0001
Formula 1
wherein:
Ri is selected from Η, CI, Br or I;
R2 is selected from hydrogen or a straight chain or a branched C|_7 alkyl; wherein said alkyl is optionally substituted with a phenyl group; and the substituent when present in the phenyl group is one or more substituents independently selected from CI, Br, F, I, N02, CN, C i.5 alkyl, phenyl, or a C 1 -C4 alkoxy;
R3 is selected from a straight or a branched chain C |_y alkyl; or a C6-C|4 aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; said aryl group is optionally substituted with one or more substituent independently selected from CI, Br, F, I, C|.5 alkyl, phenyl, or a C 1 -C4 alkoxy;
said process comprising:
reacting a compound of formula VI I with an alkylating agent such as alkyl halide, or dialkyi sulfate in the presence of a base selected from alkali metal hydroxide base, such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; or organic bases such as triethyl amine, di-isopropyl amine, di-isopropyl ethyl amine, pyridine, pyrrolidine or Ν,Ν-dimethylaniline, to obtain a compound of formula VI;
216
Figure imgf000211_0001
Formula VII Formula VI wherein:
R.3 is selected from a straight or a branched chain C i -7 alkyl; or a Ce-C^ aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl; said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C |-5 alkyl, phenyl, or a C1 -C4 alkpxy; and
halogenating the compound of formula VI with a halogenating agent selected from -chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in the presence of a polar solvent selected from Ν,Ν-dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran, ethyl acetate, or butyl acetate, to obtain the compound of formula I.
16. The process as claimed in claim 15, wherein said compound of formula VII is prepared by a process comprising:
treating a compound of formula X with phosphoryl chloride in the presence of a polar solvent selected from Ν,Ν-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, acetonitrile, dichloromethane, 1 ,2-dichloroethane, or tetrahydrofuran, to obtain a compound of formula IX;
Figure imgf000211_0002
Formula X Formula IX
wherein:
217 R3 is selected from a straight or a branched chain Ci_ alkyl; or a C6-C 14 aryl group; said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl;
said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C 1 alkyl, phenyl, or a C 1 -C4 alkoxy;
treating the compound of formula IX with hydroxylamine hydrochloride in the presence of an alcohol selected from methanol, ethanol or propanol, to obtain a compound of formula VIII; and
Figure imgf000212_0001
treating the compound of formula VIII with sodium azide in the presence of ammonium chloride and a polar solvent selected from N,N- dimethylformamide, N,N-dimethylacetamide, N-methyl-2- pyrrolidone,tetrahydrofuran or water, to obtain the compound of formula VII.
17. The process as claimed in claim 15, wherein said compound of formula VII is prepared by a process comprising:
treating a compound of formula X with iodine and a strong oxidizing agent such as hydrogen peroxide in aqueous medium to obtain a compound of formula XII;
Figure imgf000212_0002
X Formula XII wherein:
R3 is selected from a straight or a branched chain Ci-7 alkyl; or a Cs-C^ aryl group; wherein said straight or branched chain alkyl is optionally substituted with one or more substituents independently selected from CI, Br, I, or phenyl;
218 said aryl group is optionally substituted with one or more substituents independently selected from CI, Br, F, I, C|_5 alkyl, phenyl, or a C| -C4 alkoxy;
treating the compound of formula XII with either
potassium ferrocyanide and palladium (II) acetate in the presence of a base selected from alkali metal hydroxide base such as sodium hydroxide, potassium hydroxide or lithium hydroxide; or an alkali metal carbonate base selected from sodium carbonate, sodium bicarbonate, potassium carbonate or cesium carbonate; and a polar solvent selected from Ν,Ν-dimethylformamide, N,N-dimethylacetamide, n- methyl-2-pyrrolidone, acetonitrile, acetone, dichloromethane, 1 ,2-dichloroethane, methanol, tetrahydrofuran or water; or
sodium cyanide or copper cyanide in the presence of cuprous halides such as cuprous iodide and Ν,Ν-dimethyl ethylene diamine with a non polar solvent such toluene, xylene, or benzene,
to obtain a compound of formula XI; and
Figure imgf000213_0001
Formula XI
treating the compound of formula XI with sodium azide and either tri-n-butyl tin chloride in the presence of a non polar solvent selected from toluene, xylene or benzene; or ammonium chloride and Ν,Ν-dimethylformamide, to obtain the compound of formula VII.
18. The process as claimed in claim 15 for preparing a compound of formula I, its derivatives, salts, stereoisomers or regioisomers thereof, comprising
reacting 5-( l -methy!- lH-pyrazol-4-yl)-2H-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole; and
chlorinating 2-methyl-5-( l -methyl- lH-pyrazol-4-yl)-2H-tetrazole with N- chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l -methyl- lH- pyrazol-4-yl)-2-methyl-2H-tetrazole of formula I.
219
19. The process as claimed in claim 15, for preparing a compound of formula . I, its derivatives, salts, stereoisomers or regioisomers thereof, comprising
treating 1-methyl- lH-pyrazole with phosphoryl chloride in the presence of Ν,Ν-dimethylformamide, to obtain 1 -methyl- lH-pyrazole-4-carbaldehyde;
treating 1 -methyl- lH-pyrazole-4-carbaldehyde with hydroxylamine hydrochloride in the presence of ethanol, to obtain 1- methyl -lH-pyrazole-4- carbaldehyde oxime;
treating 1 -methyl- 1 H-pyrazole-4-carbaldehyde oxime with sodium azide in the presence of ammonium chloride and Ν,Ν-dimethylformamide, to form 5-( l - methyl-l H-pyrazol-4-yl)-2H-tetrazole;
reacting 5-( l -methyl- lH-pyrazole-4-yl)-2H-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l -methyl-lH-pyrazol-4-yl)-2H-tetrazole; and
chlorinating 2-methyl-5-(l -methyl- lH-pyrazole-4-yl)-2H-tetrazole with N- chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro-l -methyl-lH- pyrazo!-4-yl)-2-methyl-2H-tetrazole of formula I.
20. The process as claimed in claim 15, for preparing a compound of formula 1, its derivatives, salts, stereoisomers or regioisomers thereof, comprising
treating .1 -methyl- lH-pyrazole with iodine and hydrogen peroxide in aqueous medium to obtain 4-iodo- l -methyl- lH-pyrazole;
treating 4-iodo- l -methyl- lH-pyrazole with potassium ferrocyanide and palladium (II) acetate in the presence of sodium carbonate, and N,N- dimethylacetamide, to obtain l -methyl- lH-pyrazole-4-carbonitrile;
treating l -methyl-l H-pyrazole-4-carbonitrile with sodium azide and either with tri-n-butyl tin chloride in the presence of toluene, or ammonium chloride in the presence of N,N-dimethylformamide to obtain 5-( l -methyl- l H-pyrazol-4-yl)-2H- tetrazole;
reacting 5-( l -methyl- lH-pyrazol-4-yl)-2H-tetrazole with methyl iodide and dimethyl sulphate, in the presence of potassium hydroxide and potassium carbonate to obtain 2-methyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole; and
chlorinating 2-methyl-5-(l -methyl- lH-pyrazol-4-yl)-2H-tetrazole with N- chlorosuccinimide, in the presence acetonitrile, to obtain 5-(5-chloro- l -methyl- 1H- pyrazol-4-yl)-2-methyl-2H-tetrazole of formula I.
220
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4650892A (en) 1985-01-14 1987-03-17 The Dow Chemical Company Process for the preparation of herbicidal sulfonamides
JPH0341007A (en) * 1986-04-11 1991-02-21 E I Du Pont De Nemours & Co Herbicide
EP0204513B1 (en) 1985-05-30 1991-07-17 E.I. Du Pont De Nemours And Company Herbicidal sulfonamides
EP2264017A1 (en) * 2008-04-04 2010-12-22 Takeda Pharmaceutical Company Limited Heterocyclic derivative and use thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4650892A (en) 1985-01-14 1987-03-17 The Dow Chemical Company Process for the preparation of herbicidal sulfonamides
EP0204513B1 (en) 1985-05-30 1991-07-17 E.I. Du Pont De Nemours And Company Herbicidal sulfonamides
JPH0341007A (en) * 1986-04-11 1991-02-21 E I Du Pont De Nemours & Co Herbicide
EP2264017A1 (en) * 2008-04-04 2010-12-22 Takeda Pharmaceutical Company Limited Heterocyclic derivative and use thereof

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