AU8211698A - Fluoroalkenecarboxylic acid derivatives, processes for their preparation and insecticidal compositions comprising them - Google Patents

Fluoroalkenecarboxylic acid derivatives, processes for their preparation and insecticidal compositions comprising them Download PDF

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AU8211698A
AU8211698A AU82116/98A AU8211698A AU8211698A AU 8211698 A AU8211698 A AU 8211698A AU 82116/98 A AU82116/98 A AU 82116/98A AU 8211698 A AU8211698 A AU 8211698A AU 8211698 A AU8211698 A AU 8211698A
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hydrogen
alkyl
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AU734489B2 (en
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Manfred Boger
Tibor Gogh
Peter Maienfisch
Thomas Pitterna
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Novartis AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
    • C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
    • C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)

Description

PI/5-30022/A FLUOROALKENECARBOXYLIC ACID DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND INSECTICIDAL COMPOSITIONS COMPRISING THEM The present invention relates to novel fluoroalkenecarboxylic acid derivatives, to processes for their preparation, to insecticidal compositions comprising the novel fluoroalkenecarboxylic acid derivatives as active compounds, and to use of the novel fluoroalkenecarboxylic acid derivatives for controlling harmful insects and acarides. The present invention provides compounds of the formula
R
3 O R F C H2"C H2 'lx C() C CHC CH 0 C N C 2 1 11 F - - _ iOn in which
R
1 and R 2 independently of one another are hydrogen; or alkyl, a group N , aryl, cycloalkyl, alkenyl or alkynyl, which are substituted or unsubstituted; R3 is hydrogen, fluorine or methyl; m is 0, 1, 2, 3, 4 or 5; n is0or1; X is oxygen or NR 4 , and R4 is hydrogen or C-C 6 -alkyl or benzyl, which are substituted or unsubstituted, and, if appropriate, its possible E/Z isomers, E/Z isomer mixtures and/or tautomers, in each case in free form or in salt form, with the proviso that a) R 3 is not hydrogen or fluorine and m and n are not both 0 if X is oxygen and R 1 and R 2 independently of one another are hydrogen or unsubstituted or substituted alkyl, alkenyl, cyo'oalkyl, aryl or heteroaryl; b) R 3 is not hydrogen or fluorine and m and n are not both 0 if R 4 is hydrogen and R 1 and R 2 independently of one another are hydrogen or unsubstituted or substituted alkyl, aryl or heteroaryl; c) m is not 0, 1 or 2 and R 4 is hydrogen, alkyl or haloalkyl if one of the radicals R 1 or R 2 is 4-alkylsulphonyloxyphenyl, 4 haloalkylsulphonyloxyphenyl or 4-haloalkoxysulphonyloxyphenyl which may or may not carry -2 further substituents, and the other radical is substituted or unsubstituted phenyl; and d) m is not 0, 1 or 2 and R 4 is not hydrogen, alkyl or haloalkyl and n is not 0 if one of the radicals R 1 und R 2 is 4-perhaloalkoxyphenyl which may or may not carry further substituents and the other is substituted or unsubstituted phenyl, a process for the preparation and the use of these compounds, E/Z isomers and tautomers; pesticides whose active compound is selected from these compounds, E/Z isomers and tautomers; and a process for the preparation and the use of these compositions; intermediates, and, if appropriate, their possible E/Z isomers, E/Z isomer mixtures and/or tautomers, in free form or in salt form, for preparing these compounds, if appropriate tautomers, in free form or in salt form, these intermediates; and a process for the preparation and the use of these intermediates and their tautomers. Preferred groups of compounds of the formula (1) are - taking into account the provisos listed above - those in which
R
1 and R 2 independently of one another are hydrogen or alkyl, cycloalkyl, alkenyl or alkynyl, which are substituted or unsubstituted,
R
3 is hydrogen, fluorine or methyl, m is 0, 1, 2, 3, 4 or 5; n is 0 or 1, X is oxygen or NR 4 , and
R
4 is hydrogen or unsubstituted or substituted C 1
-C
6 -alkyl or benzyl; in which
R
1 is hydrogen or unsubstituted or substituted alkyl, alkenyl, alkynyl or cycloalkyl,
R
2 is hydrogen or unsubstituted or substituted aryl or heteroaryl,
R
3 is hydrogen, fluorine or methyl, m is 0, 1, 2, 3, 4 or 5; n is 0 or 1, X is oxygen or NR 4 , and
R
4 is hydrogen or unsubstituted or substituted C 1
-C
6 -alkyl or benzyl; and in which -3
R
1 and R 2 independently of one another are H or aryl, which are substituted or unsubstituted,
R
3 is hydrogen, fluorine or methyl, m is 0, 1, 2, 3, 4 or 5; n is 0 or 1, X is oxygen or NR 4 , and
R
4 is hydrogen or unsubstituted or substituted C 1
-C
6 -alkyl or benzyl. The general terms used in the above definitions of the substituents of R 1 , R 2 , R 3 and R 4 are defined below as follows: Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine, especially fluorine or chlorine and in particular chlorine. Alkyl is a straight-chain or branched alkyl radical having 1 to 20 carbon atoms, which may be unsubstituted or mono- or polysubstituted. R 1 and R 2 as alkyl groups are preferably straight chain or branched alkyl radicals having 1 to 8 carbon atoms and particularly preferably alkyl radicals having 1 to 4 carbon atoms. Suitable substituents of R 1 and R 2 as alkyl groups are hydroxyl, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morpholino, alkoxycarbonyl, alkylcarbonyloxy, cycloalkyl, aryl, aryloxy, arylthio, arylsulphonyl, arylsulphonyloxy, arylcarbonyl or heteroaryl, where aryl or heteroaryl groups for their part may be mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro, cyano, phenoxy, halophenoxy, phenylthio or halophenylthio. The alkyl radicals which are present as alkyl groups in the substituents of R 1 and R 2 preferably have 1 to 4 carbon atoms. These alkyl radicals are particularly preferably methyl or ethyl radicals. Examples of
R
1 and R 2 as alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2,2-dimethylpropyl, isopentyl, n-hexyl, 2-methylpentyl, 3 methylpentyl, 1,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, n-octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, hexadecyl and octadecyl. Preferred substituents of R 1 and R 2 as alkyl groups are hydroxyl, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morpholino, alkoxycarbonyl, alkylcarbonyloxy, cycloalkyl, where phenyl, phenoxy, phenylthio, phenylsulphonyl, phenylsulphonyloxy, benzoyl and pyridyl may be substituted by halogen, yl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro or cyano. 4' -4 Mono- or polysubstitution of a radical R 1 or R 2 is in particular mono- to tetrasubstitution, preferably mono- to disubstitution and particularly preferably monosubstitution, where R 1 and
R
2 in particular as lower alkyl radicals, such as methyl or ethyl, may be perhalogenated, in particular perfluorinated, in the case of a substitution by halogen. In the case of polysubstitution, the respective substituents may be identical or different. Aryl is phenyl or naphthyl, preferably phenyl. Heteroaryl means aromatic radicals having 5 or 6 ring members and 1 or 2 heteroatoms, selected from the group consisting of nitrogen, oxygen and sulphur. Examples of heteroaryl radicals are pyrrolyl, furyl, thienyl, imidazolyl, pyrrazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl, where the radicals R 1 and R 2 as heteroaryl radicals are in each case attached by a carbon atom and, if appropriate, a benzene ring may be fused to the radicals. Preferred heteroaryl radicals are pyridyl, pyrimidinyl, quinolyl, furyl and thienyl. Aryl radicals and heteroaryl radicals may be unsubstituted or mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulphonyloxy, haloalkylsulphonyloxy, haloalkoxysulphonyloxy, nitro, cyano, benzoyl, phenyl, phenoxy, phenylthio, trialkylsilyl, benzyloxy, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, anilino, cycloalkylalkoxy or halocycloalkylalkoxy, heteroaryl or heteroaryloxy, where benzoyl, phenyl, phenoxy, phenylthio, benzyloxy, anilino, heteroaryl and heteroaryloxy radicals as substituents for their part may be mono- or polysubstituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro, cyano, phenoxy, halophenoxy, phenylthio, halophenylthio, cycloalkylalkoxy or halocycloalkylalkoxy. The alkyl groups which are present as or in the substituents of R 1 and R 2 as aryl or heteroaryl groups preferably have 1 to 4 carbon atoms. These alkyl groups are particularly preferably methyl or ethyl groups. Alkenyl means straight-chain or branched alkenyl radicals having 3 to 20, preferably 3 to 8, carbon atoms and particularly preferably alkenyl radicals having 3 to 5 carbon atoms, which may be unsubstituted or mono- or polysubstituted by halogen. Alkenyl preferably refers to those alkenyl radicals which are attached via a saturated carbon atom, i.e. alkenyl radicals having an intermittent or terminal double bond. Examples of alkenyl radicals are allyl, methallyl, but-2-en-1-yl, but-3-en -1-yl, pent-2-en-1-yl, pent-3-en-1-yl, pent-4-en-1-yl, 2 methylbut-2-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1yl, hept-2-en-1-yl, oct-2-en-1-yl and dec-2-en-1-yl. Particularly preferred alkenyl radicals are allyl and methallyl. Alkynyl means straight-chain or branched alkynyl radicals having 3 to 20, preferably 3 to 8 carbon atoms and particularly preferably alkynyl radicals having 3 to 5 carbon atoms, which -5 may be unsubstituted or mono- or polysubstituted by halogen. Alkynyl preferably refers to those alkynyl radicals which are attached via a saturated carbon atom, i.e. alkynyl radicals having an intermittent or terminal triple bond. Examples of alkynyl radicals are propargyl, but 2-yn-1-yl, but-3-yn-1-yl, pent-2-,- 3- or -4-yn-1-yl, hex-2-, -3-,- 4- or 5-yn-1-yl, hept-2-, -3-, -4 , -5- or -6-yn-1-yl and oct-2-,-3-,-4-,-5-,-6- or -7-yn-1-yl. A particularly preferred alkynyl radical is the propargyl radical. Cycloalkyl means cycloalkyl radicals having 3 to 7 carbon atoms which may be unsubstituted or mono- or polysubstituted by halogen, alkyl or haloalkyl, where the alkyl and haloalkyl radicals preferably contain 1 to 4 carbon atoms and particularly preferably 1 to 2 carbon atoms. Examples of cycloalkyl radicals are cyclopropyl, 2-melthylcyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3,4-dimethylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 4 methylcyclohexyl, 3,4-dimethylcyclohexyl, 2,4-dimethylcyclohexyl and cycloheptyl. The meaning illustrated above of the general terms used in the definition applies, unless expressly stated otherwise, to the entire present description. The present invention relates in particular to compounds of the formula (1) in which, taking into account the provisos listed above,
R
1 and R 2 independently of one another are hydrogen; C-C 2 0 -alkyl, which may be straight chain or branched and and may be mono- to tetrasubstituted by hydroxyl, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morpholino, alkoxycarbonyl, alkylcarbonyloxy, cycloalkyl, phenyl, naphthyl, phenoxy, naphthoxy, phenylthio, naphthylthio, phenylsulphonyl, naphthylsulphonyl, phenylsulphonyloxy, naphthylsulphonyloxy, benzoyl, naphthoyl, heteroaryl or heteroaryloxy having 5 to 6 ring members and 1 to 2 hetero atoms N, 0 or S, where the aryl or heteroaryl groups mentioned for their part may be mono- or disubstituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro, cyano, phenoxy, halophenoxy, phenylthio or halophenylthio;
C
3
-C
20 -alkenyl, which may be straight-chain or branched and may be mono- to tetrasubstituted by halogen;
C
3
-C
20 -alkynyl, which may be straight-chain or branched and may be mono- to tetrasubstituted by halogen;
C
3
-C
7 cycloalkyl, which may be mono- or tetra-substituted by halogen, alkyl or haloalkyl;
ZIN
-6 Phenyl or naphthyl, which may be mono- to tetra-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkylthio, haloalkylthio, alkylsulphonyloxy, haloalkylsulphonyloxy, haloalkoxysulphonyloxy, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkylsilyl, phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl or heteroaryloxy having 5 to 6 ring members and 1 to 2 heteroatoms N, 0 or S, where phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl and heteroaryloxyradicals as substituents may for their part be mono- or disubstituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro, cyano, phenoxy, phenylthio, halophenylthio, cycloalkylalkoxy or halocycloalkylalkoxy; heteroaryl having 5 bis 6 ring members and 1 to 2 heteroatoms N, 0 or S, which may be mono- to tetra-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkylsilyl, phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl or heteroaryloxy having 5 to 6 ring members and 1 to 2 heteroatoms N, 0 or S, where phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl and heteroaryloxy radicals as substituents for their part may be mono or disubstituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro, cyano, phenoxy, phenylthio, halophenylthio, cycloalkylalkoxy, halocycloalkylalkoxy;
R
3 is hydrogen, fluorine or methyl; m is 0, 1, 2, 3, 4 or 5; n is 0 or 1; and X is oxygen or NR 4 , where
R
4 is hydrogen, C-C 4 -alkyl which may be mono- or polysubstituted by halogen, C-C 4 alkoxy or di-C-C 4 -alkylamino, or is benzyl which may be mono- or polysubstituted by halogen, C-C 4 -alkyl, halo-C-C 4 -alkyl, C-C 4 -alkoxy, nitro or cyano. Preference is given to compounds of the formula (1) in which, taking into account the provisos listed above, R 1 and R 2 independently of one another are hydrogen, C-C 8 -alkyl, which may be straight-chain or branched and may be mono- or disubstituted by hydroxyl, halogen, C-C 4 -alkoxy, halo-C-C 4 -alkoxy, C-C 4 -alkoxyalkoxy,
C-C
4 -alkythio, halo-C-C 4 -alkylthio, C-C 4 -alkylsulphinyl, C-C 4 -alkylsulphonyl, C-C 4 alkylsulfonyloxy, C-C 4 -alkylcarbonyl, di-C-C 4 -alkylamino, pyrrolidino, piperidino, morpholino,
C-C
4 -alkoxycarbonyl, C-C 4 -alkylcarbonyloxy, C 3
-C
6 -cycloalkyl, phenyl, naphthyl, phenoxy, ,14 -7 naphthoxy, phenylthio, naphthylthio, phenylsulphonyl, naphthylsulphonyl, phenyl sulphonyloxy, naphthylsulphonyloxy, benzoyl, naphthoyl, heteroaryl or heteroaryloxy having 5 to 6 ring members and I to 2 hetero atoms N, 0 or S, where the aryl or heteroaryl groups mentioned for their part may be mono- or disubstituted by halogen,
C-C
4 -alkyl, halo-C-C 4 alkyl, C-C 4 -alkoxy, halo-C-C 4 -alkoxy, C-C 4 -alkylthio, nitro, cyano, phenoxy, halophenoxy, phenylthio or halophenylthio;
C
3 -CB-alkenyl which may be straight-chain or branched and may be mono- or disubstituted by halogen;
C
3
-C
8 -alkynyl which may be straight-chain or branched and may be mono- or disubstituted by halogen;
C
3
-C
7 -cycloalkyl which may be mono- or disubstituted by halogen, Cr-C 4 -alkyl or halo-C-C 4 alkyl; phenyl or naphthyl which may be mono- or disubstituted by halogen,
C-C
4 -alkyl, halo-C-C 4 alkyl, C-C 4 -alkoxy, halo-C-C 4 -alkoxy, C3-C6-cycloalkyl-CrC4-alkoxy, halo-C-C 4 -cycloalkyl
C-C
4 -alkoxy, C-C 4 -alkylthio, halo-C-C 4 -alkylthio, C-C4-alkylsulphonyloxy, halo-C-C 4 alkylsulphonyloxy, halo-C-C4-alkoxysulphonyloxy,
C-C
4 -alkylamino, di-C-C 4 -alkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, tri-C-C 4 -alkylsilyl, phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl or heteroaryloxy having 5 to 6 ring members and 1 to 2 hetero atoms N, 0 or S, where phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl and heteroaryloxy radicals as substituents for their part may be mono- or disubstituted by halogen,
C-C
4 -alkyl, halo-C-C 4 -alkyl, C-C 4 alkoxy, halo-C-C 4 -alkoxy, C-C 4 -alkylthio, nitro, cyano, phenoxy, phenylthio, halophenylthio,
C
3
-C
6 -cycloalkyl-C-C 4 -alkoxy or halo-C3-C6-cycloalkyl-CrC4-alkoxy, heteroaryl having 5 to 6 ring members and 1 to 2 hetero atoms N, 0 or S which may be mono- or disubstituted by halogen,
C-C
4 -alkyl, halo-C-C 4 -alkyl, C-C 4 -alkoxy, halo-C-C 4 alkoxy, C3-C6-cycloalkyl-CrC4-alkoxy, halo-C 3
-C
6 -cycloalkyl-C-C 4 -alkoxy, C-C 4 -alkylthio, halo-C-C 4 -alkylthio,
C-C
4 -alkylamino, di-C-C 4 -alkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, tri-C-C 4 -alkylsilyl, phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl or heteroaryloxy having 5 to 6 ring members and 1 to 2 hetero atoms N, 0 or S, where phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl and heteroaryloxy radicals as substituents for their part may be mono- or disubstituted by halogen,
C-C
4 -alkyl, halo-C-C 4 -alkyl, C-C 4 -alkoxy, halo-C-C 4 -alkoxy, -8
C-C
4 -alkylthio, nitro, cyano, phenoxy, phenylthio, halophenylthio, C 3
-C
6 -cycloalkyl-C-C 4 alkoxy or halo-C 3
-C
6 -cycloalkyl-C-C 4 -alkoxy, R3 is hydrogen, fluorine or methyl, m is 0, 1, 2, 3 or 4, n is 0 or 1 and X is oxygen or NR 4 , where R4 is hydrogen, C-C 4 -alkyl which may be mono- to disubstituted by halogen C-C 4 alkoxy or di-C-C 4 -alkylamino, or is benzyl which may be mono- to disubstituted by halogen, C-C 4 -alkyl, halo-C-C 4 -alkyl, C 1
-C
4 alkoxy, nitro or cyano. The preferred meanings defined above of the radicals R 1 , R 2 , R 3 and R 4 apply analogously to the subgroups of compounds of the formula (I) defined above. Among the compounds of the formula (1), preference is furthermore given to those in which a) R 3 is hydrogen; b) m is 0, 1, 2, 3 or 4, particularly preferably 1 or 4; c) n is 0; d) R 4 is hydrogen; e) R 1 and R 2 are as defined above, R 3 is hydrogen, m is 0, 1, 2, 3 or 4, n is 0 or 1, and X is oxygen or NH; f) R 1 and R 2 are as defined above, R 3 is hydrogen, m is 1 or 4, n is 0, and X is oxygen or NH; g) R 1 is as defined above, R 3 is hydrogen and R 2 is a group Alk-0 N in which alk is methyl or ethyl and the phenyl ring is substituted or unsubstituted. Particularly preferred individual compounds are compounds of the formula (1) in which R 3 is hydrogen and
R
1 is hydrogen, R 2 is hydrogen, X is oxygen, m is 1 and n is 0; -9 b) R 1 is methyl, R 2 is methyl, X is oxygen, m is 1 and n is 0; c) R 1 is methyl, R 2 is phenyl, X is oxygen, m is 1 and n is 0; d) R 1 is methyl, R 2 is 4-trifluoromethylphenyl, X is oxygen, m is 1 and n is 0; e) R 1 is methyl, R 2 is 4-nitrophenyl, X is oxygen, m is 1 and n is 0; f) R 1 is methyl, R 2 is 4-tert-butylphenyl, X is oxygen, m is 1 and n is 0; g) R 1 is phenyl, R 2 is phenyl, X is oxygen, m is 1 and n is 0; h) R 1 is hydrogen, R 2 is phenyl, X is oxygen, m is 1 and n is 0; i) R 1 is phenyl, R 2 is benzyl, X is oxygen, m is 1 and n is 0; j) R 1 is ethyl, R 2 is 4-chlorophenyl, X is oxygen, m is 1 and n is 0; k) R 1 is hydrogen, R 2 is methyl, X is NH, m is 1 and n is 0; I) R 1 is methyl, R 2 is methyl, X is NH, m is 1 and n is 0; m) R 1 is methyl, R 2 is phenyl, X is NH, m is 1 and n is 0; n) R 1 is methyl, R 2 is 3-trifluoromethylphenyl, X is NH, m is 1 and n is 0; o) R 1 is methyl, R 2 is 4-tert-butylphenyl, X is NH, m is 1 and n is 0; p) R 1 is phenyl, R 2 is phenyl, X is NH, m is 1 and n is 0; q) R 1 is hydrogen, R 2 is phenyl, X is oxygen, m is 1 and n is 0; r) R 1 is phenyl, R 2 is benzyl, X is NH, m is 1 and n is 0; s) R 1 is ethyl, R 2 is 4-chlorophenyl, X is NH, m is 1 and n is 0; t) R 1 is hydrogen, R 2 is hydrogen, X is NH, m is 1 and n is 1; u) R 1 is methyl, R 2 is methyl, X is NH, m is 1 and n is 1; v) R 1 is methyl, R 2 is phenyl, X is NH, m is 1 and n is 1; w) R 1 is methyl, R 2 is 3-trifluoromethylphenyl, X is NH, m is 1 and n is 1; x) R 1 is methyl, R 2 is 4-tert-butylphenyl, X is NH, m is 1 and n is 1; y) R 1 is phenyl, R 2 is phenyl, X is NH, m is 1 and n is 1; z) R 1 is hydrogen, R 2 is phenyl, X is oxygen, m is 1 and n is 1; aa) R 1 is phenyl, R 2 is benzyl, X is NH, m is 1 and n is 1; or -10 bb) R 1 is ethyl, R 2 is 4-chlorophenyl, X is NH, m is 1 and n is 1. The present invention furthermore provides a process for preparing a compound of the formula (1) which comprises a) preparing a compound of the formula (1) in which n is 0 and R 1 , R 2 , R 3 , X and m are as defined above under formula (1) by reacting a compound of the formula Ra 0 F C C ccH2 C 1- m F in which R 3 and m are as defined under formula (I) and Y 2 is Cl, Br or OS0 2 -alkyl with a compound of the formula /R, HX--N-C R2 in which R 1 , R 2 and X are as defined under formula (1); b) preparing compounds of formula (1) in which n is 0 and X is NR 4 and R 1 , R 2 , R 3 and m are as defined under formula (I) by reacting a compound of the formula R3 0 F C C C CH2 C ,C N NH 2 F R4 in which R 3 , R 4 and m are as defined under formula (1) with a compound of the formula o-c (V)
R
2 in which R 1 and R 2 are as defined under formula (1); and c) preparing compounds of the formula (1) in which n is 1 and R 1 , R 2 , R 3 , R 4 , X and m are as defined under formula (1) by reacting a compound of the formula 4zi Ra 0 13 11 F 73I i- N H I -I C CHfH CH21M OH (VI) in which R 3 and m are as defined above under formula (1) with a compound of the formula R,
~CH
2 x N .(VI Y, C N R2( Vil) in which Y 1 is Cl, Br or OS0 2 -alkyl and X, R 1 and R 2 are as defined above under formula (I). The starting materials of the formulae (11) and (VI) are known or can be prepared analogously to known processes. The starting materials of the formula (ll) can be prepared in a manner known per se by reacting a ketone of the above formula (V) with hydrazine, with a hydrazine which is monosubstituted by R 4 according to the above definition or with hydroxylamine, where the ketones of the formula (V) for their part are obtainable by customarry processes known for preparing ketones. The starting materials of the formula (II) can be obtained by reacting an acyl halide of the formula R3 0 F C C NICH2 C C~ m2 I CHf2 C IM Hal F in which Hal is chlorine or bromine with a hydrazine which is monosubstituted by R 4 according to the definition given above. The starting materials of the formula (VII) can be obtained by reacting a chloroacetyl halide, for example chloroacetyl chloride, with a compound of the formula (1ll) according to the above definition. The reaction of the process a) is preferably carried out in an inert solvent which is free of hydroxyl groups, in the presence of an organic base, for example pyridine, RPA4 imethylaminopyridine, 4-pyrrolidinopyridine, lutidine, collidine, trialkylamine, -12 N,N-dialkylaniline, or a bicyclic non-nucleophilic base, such as 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0] non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (1,5-5) (DBU). The reaction is generally carried out at temperatures from -30 0 C to +70 0 C, preferably from -10*C to +50 0 C. It is advantageously carried out in the presence of a solvent or solvent mixture which is inert to the reaction. Suitable for this purpose are, for example, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylenes, petroleum ether, hexane; halogenated hydrocarbons, such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, tetrachloroethylene; ethers and ether-like compounds, such as dialkyl ethers (diethyl ether, diisopropyl ether, tert-butyl methyl ether, etc.), anisole, dioxane, tetrahydrofuran; nitriles, such as acetonitrile, propionitrile; esters, such as ethyl acetate, propyl acetate or butyl acetate; ketones, such as acetone, diethyl ketone, methyl ethyl ketone; and mixtures of such solvents with one another. However, the reaction can also be carried out in an excess of one of the abovementioned bases, or, instead of the base, it is also possible to employ a second equivalent or else an even greater excess of the compound of the formula 1. The reaction is carried out under atmospheric pressure; however, it is also possible to carry out the reaction under elevated or reduced pressure. The reaction of process b) is advantageously carried out in an inert solvent at a temperature of from 20 0 C to 150*C, preferably from 40*C to 120 0 C, if appropriate in the presence of a catalytic amount of an acid, such as acetic acid or p-toluenesulphonic acid. Preferred inert solvents are lower alkanols, in particular methanol and ethanol. The reaction of the process c) is advantageously carried out in an inert solvent in the presence of a base and, if appropriate, in the presence of a catalyst, for example Nal or CsF, preferred inert solvents being polar aprotic solvents, such as N,N-dimethylformamide, dimethyl sulphoxide, dioxane and tetrahydrofuran. Suitable bases are, in particular, pyridine, 4-dimethylaminopyridine, 4-pyrrolidinopyridine, lutidine, collidine, trialkylamine, N,N-dialkylaniline, or a bicyclic non-nucleophilic base, such as 1 ,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (1,5-5) (DBU). The reactions described above and below are carried out in a manner known per se, for example in the absence or, if appropriate, presence of a suitable solvent or diluent or a mixture thereof, as required with cooling, at room temperature or with heating, for example in a temperature range of approximately -80 0 C to the boiling point of the reaction mixture, -13 preferably from approximately -20 0 C to approximately +1 50*C and, if required, in a closed vessel, under superatmospheric pressure, in an atmosphere of inert gas and/or under anhydrous conditions. Particularly advantageous reaction conditions are shown in the examples. The compounds of the formula (1) according to the invention are tolerated favourably by homoiotherms, fish and plants, and they are useful active compounds in the field of pest control. The active compounds according to the invention are active, in particular, against insects and arachnids, as encountered on useful and ornamental plants in agriculture and horticulture, in particular in rice, cotton, vegetable and fruit plantings, and in forests. The compounds of the formula (1) are particularly suitable for controlling insects in crops of rice, fruit and vegetables, in particular plant-damaging insects, such as Aphis craccivora, Nila parvata lugens and Nephotettix cincticeps. Other areas of use of the active compounds according to the invention are the protection of stored products and materials and the hygiene sector, in particular the protection of pets and useful animals. The compounds of the formula (1) are active against all or individual developmental stages of normally-sensitive, but also resistant, pest species. Their effect may become apparent for example in the destruction of pests, either immediately or only after some time has elapsed, for example during ecdysis, or as a reduced oviposition and/or hatching rate. The animal pests mentioned include, for example, those mentioned in the European Patent Application EP-A-736'252. (CASE 20400) EP-A-736'252 is therefore included by reference in the present subject-matter of the invention. The compounds of the formula (1) are suitable, in particular, for use as active compounds for controlling pests from the order Homoptera and from the order Akarina. The compounds of the formula (1) are particularly suitable for controlling pests in crops of cotton, vegetable, fruit and rice, such as spider mites, aphids, caterpillars of butterflies and moths, and rice leaf hoppers. Control is directed mainly against spider mites, such as Panonychus ulmi, aphids, such as Aphis craccivora, caterpillars of moths and butterflies, such as those of Heliothis virescens, and rice leafhoppers, such as Nilaparvata lugens or Nephotettix cincticeps. The good pesticidal action of the compounds of the formula (1) according to the invention corresponds to a destruction rate (mortality) of at least 50-60% of the pests mentioned. TO T R7 4 4e- -14 The activity of the compounds of the formula (I) according to the invention and of the compositions comprising them can be substantially widened and adapted to specific circumstances by addition of other insecticides and/or acaricides. Suitable additives are, for example, representatives of the following classes of active compounds: organic phosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, pyrethroides, chlorinated hydrocarbons and Bacillus thuringiensis preparations. The compounds of the formula (I) are employed as such or, preferably, together with auxiliaries which are customary in the art of formulation, and accordingly, they can be processed, for example, to emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or encapsulations in polymeric substances, in a known manner. The application methods, such as spraying, atomizing, dusting, broadcasting or watering, are, like the compositions, chosen according to the intended aims and the prevailing conditions. The formulation, i.e. the agents, preparations or compositions comprising an active compound (I), or combinations of these active compounds with other insecticides or acaricides, and, if appropriate, a solid or liquid additive are prepared in a known manner, for example by intimate mixing and/or grinding of the active compounds with extenders, for example solvents, solid carriers and, if appropriate, surface-active compounds (surfactants). Suitable auxiliaries, such as solvents, solid carriers, surface-active compounds, nonionic surfactants, cationic surfactants, anionic surfactants and other auxiliaries in the compositions used according to the invention are, for example, the same as those described in EP-A-736'252. The pesticidal preparations generally comprise from 0.1 to 99%, in particular from 0.1 to 95%, of active compound I or of the combination of this active compound with other insecticides and/or acaricides and from 1 to 99.9%, in particular from 5 to 99.9%, of a solid or liquid auxiliary, where generally from 0 to 25%, in particular from 0.1 to 20%, of the preparations may be surfactants (per cent means in each case per cent by weight). Whereas concentrated compositions are usually preferred as commercial products, the end user generally employs dilute preparations which have a substantially lower concentration of active compound. Typical use concentrations are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm. The application rates per hectare are generally from 1 to 1000 g of active compound per hectare, preferably from 25 to 500 g/ha.
-15 Preferred formulations have, in particular, the following composition (% = per cent by weight): Emulsifiable concentrates: Active compound: from 1 to 90%, preferably from 5 to 20% Surfactant: from 1 to 30%, preferably from 10 to 20% Liquid carrier: from 5 to 94%, preferably from 70 to 85% Dusts: Active compound: from 0.1 to 10%, preferably from 0.1 to 1% Solid carrier: from 99.9 to 90%, preferably from 99.9 to 99% Suspension concentrates: Active compound: from 5 to 75%, preferably from 10 to 50% Water: from 94 to 24%, preferably from 88 to 30% Surfactant: from 1 to 40%, preferably from 2 to 30% Wettable powders: Active compound: from 0.5 to 90%, preferably from 1 to 80% Surfactant: from 0.5 to 20%, preferably from 1 to 15% Solid carrier: from 5 to 95%, preferably from 15 to 90% Granules: Active compound: from 0.5 to 30%, preferably from 3 to 15% Solid carrier: from 99.5 to 70%, preferably from 97 to 85% The preparations may also comprise other auxiliaries, such as stabilizers, for example non epoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, and also fertilizers or other active compounds for obtaining special effects. The examples below serve to illustrate the invention. They do not limit the invention. Temperatures are stated in degrees Celsius. ,-\-.RA/ 0-k -16 Example HI: 0 CH 3
F
2 C=CH-fCH2 C-0-N=C
CH
3 0.73 g (10 mmol) of acetone oxime and 1.01 g (10 mmol) of triethylamine are dissolved in 30 ml of anhydrous benzene. At 5-10 0 C, the solution is admixed over a period of 30 minutes and with vigorous stirring with 1.68 g (10 mmol) of 6,6-difluorohex-5-enoic acid chloride (DAHSCI), and the mixture is stirred at room temperature for another 10 hours and then filtered through a glass suction filter, and the filtrate is concentrated using a rotary evaporator. The resulting crude product is separated by silica gel column chromatography (ethyl acetate:isohexane = 20:80). This gives the title compound of nD 20 = 1.6893. Example H2: 0l
C
6
H
5
F
2 C=CH-ECH] C -NH-N= C CH 1.5 g (7.6 mmol) of benzophenone hydrazone and 0.77 g (7.6 mmol) of triethylamine are dissolved in 30 ml of anhydrous benzene, and at 5-1 0*C the solution is admixed with 1.29 g (7.6 mmol) of 6,6-difluoro-hex-5-enoic acid chloride (DAHSCI) over a period of 30 minutes. The mixture is then stirred at room temperature for another 10 hours and filtered through a glass suction filter, and the filtrate is concentrated using a rotary evaporator. The resulting crude product is separated by silica gel column chromatography (ethyl acetate:isohexane = 20:80). This gives the title compound of m.p. 70-71*C. Example H3: 0
CH
3
F
2 C=CH-ECH2NH-NC' H 0.5 g (10 mmol) of hydrazine hydrate is added to 1.64 g (10 mmol) of methyl 6,6-difluorohex 5-enoate in 10 ml of methanol. The solution is heated under reflux on a water bath for 10 minutes and then concentrated using a rotary evaporator. The residue is suspended in 20 ml of methylene chloride and, at 0*C, admixed with 0.445 g (10 mmol) of acetaldehyde, and the mixture is then stirred at room temperature for another 10 hours. The methylene chloride is evaporated and the crude product is separated by silica gel column chromatography (methyl acetate:isohexane = 20:80). This gives the title compound of m.p. 78-79*C. VIAR4 441.
-17 Example H4: 0 0 ICGHS
F
2 C=CH-CH]c-O--CH2-C-NH-N=C\ 3.6 g (18.4 mmol) of benzophenone hydrazone and 1.85 g (18.3 mmol) of triethylamine are dissolved in 50 ml of benzene, and the mixture is cooled to 5 0 C. With efficient stirring, 2.06 g (18.2 mmol) of chloroacetyl chloride are slowly added dropwise such that the temperature can be kept at from 5 to 10*C at all times. After the addition of the chloroacetyl chloride, stirring is continued at room temperature for 14 hours. The mixture is filtered and the filtrate is concentrated. The residue is washed with a small amount of isohexane:acetic acid = 80:20, filtered and dried. This gives the title compound of m.p. 92-93*C. A mixture of 1.7 g (6.2 mmol) of chloroacetylbenzophenone hydrazide, 0.93 g (6.2 mmol) of 6,6-difluorohex-5-enoic acid, 0.63 g (6.2 mmol) of triethylamine and 0.2 g of Nal in 10 ml of dimethylformamide is stirred at room temperature for 14 hours. The reaction mixture is poured onto ice, the mixture is extracted with chloroform and the extract is dried over Na 2
SO
4 . The solvent is distilled off and the crude product is separated on silica gel (isohexane:ethyl acetate = 80:20). This gives the title compound no 20 = 1.5678. Example H5: S0CH F2C=C{CH2C-O-CH2-C-NH-N=C
CH
3 0.5 g (10 mmol) of hydrazine hydrate is added to a solution of 0.9 g (10 mmol) of methyl glycolate in 10 ml of methanol. For 10 minutes, the solution is heated under reflux on a water bath, and it is then concentrated using a rotary evaporator. The residue is suspended in 10 ml of methanol and admixed with 0.58 g (10 mmol) of acetone, and the mixture is then stirred at room temperature for 10 hours. The methanol is evaporated and the residue is then suspended in 20 ml of dichloromethane/tetrahydrofuran. 1.5 g (10 mmol) of 6,6 difluorohex-5-enoic acid, 406 g (10 mmol) of DCC and 0.1 g of 4-dimethylaminopyridine are added to this mixture, which is then stirred for 14 hours and filtered through a glass suction filter, and the filtrate is concentrated using a rotary evaporator. The resulting crude product is purified by silica gel column chromatography (ethyl acetate: isohexane = 20:80). This gives the title compound of no 2 0 = 1.6768. In a manner similar to that described in Examples H1 to H5, it is possible to prepare the compounds of the formula (1) listed in Tables 1 to 20.
-18 Table 1: Compounds of the formula H 0 I || FCC C 0 C F R Comp. No. R 1 R2 phys. Data 1.01 H H 1.02 H
CH
3 1.03 H
C
2
H
5 1.04 H
C
3 Hz-n 1.05 H
C
3
H
7 -i 1.06 H C 4 Hg-n 1.07 H C 4
H
9 -t 1.08 H C 6
H
1 3 -n 1.09 H
C
1 oH 21 -n 1.10 H
CH
2
C(CH
3
)
3 1.11
CH
3 H 1.12
CH
3 CH 3 1.13 CH 3
C
2
H
5 1.14
CH
3
C
3
H
7 -n 1.15
CH
3 C 3
H
7 -i 1.16
CH
3
C
4
H
9 -n 1.17 CH 3
C
4
H
9 -t 1.18
CH
3 C 6 H1 3 -n 1.19 CH 3
C
10
H
21 -n 1.20
CH
3 CH 2
C(CH
3
)
3 4) -19 Comp. No. R 1 R2 phys. Data 1.21 CH 3
C
6
H
5 1.22 CH 3
C
6
H
4 -2-Cl 1.23 CH 3
C
6
H
4 -3-Cl 1.24 CH 3 C6H 4 -4-CI 1.25 CH 3 C6H 4 -2-CF 3 1.26 CH 3 C6H 4 -3-CF 3 1.27 CH 3
C
6
H
4 -4-CF 3 1.28 CH 3 C6H 4 -2-CN 1.29 CH 3
C
6
H
4 -3-CN 1.30 CH 3
C
6
H
4 -4-CN 1.31 CH 3
C
6
H
4 -2-NO2 1.32 CH 3 C6H 4 -3-NO2 1.33 CH 3
C
6
H
4 -4-NO2 1.34 CH 3
C
6
H
4 -4-C 6
H
5 1.35 CH 3
C
6
H
4 -4-OC6H 5 1.36 CH 3
C
6
H
4 -4-C(CH 3
)
3 1.37 CH 3 C6H 4 -4-OCF 3 1.38 CH 3 C6H 4 -4-COOC 2
H
5 1.39 CH 3
C
6
F
5 1.40 CH 3
-C
6
H
2 -3,4,5-(OCH 3
)
3 1.41
CH
3 N 0 N) -0 41 -20 Comp. No. R 1 R2 phys. Data 1.42 CH 3 N-N 1.43 CH 3 \ / OH 1.44 C6H 5
CF
3 1.45 C 6 Hs C 2
H
5 1.46 C 6
H
5
C
3
H
7 -n 1.47 C 6
H
5
C
3
H
7 -i 1.48 C6H 5
C
4
H
9 -t 1.49 C6H 5
C
4
H
9 -n 1.50 C 6
H
5 cyclopropyl 1.51 C 6
H
5 cyclopentyl 1.52 C 6
H
5 cyclohexyl 1.53 C6H 5
C
6
H
5 1.54 C 6
H
5 C6H 4 -4-Cl 1.55 C 6
H
5
C
6
H
4 -4-CF 3 1.56 C 6
H
5
C
6
H
4 -4-CN 1.57 C 8
H
5
C
6
H
4 -4-NO2 1.58 C 6
H
5
C
6
H
4 -4-C 6
H
5 1.59 C 6
H
5
C
6
H
4 -4-OC 6
H
5 1.60 C 6
H
5
C
6
H
4 -4-C(CH 3
)
3 1.61 C 8
H
5
C
6
H
4 -4-OCF 3 )"4 -21 Comp. No. R, R phys. Data 1.62
C
8
H
4 -4-CI
CF
3 1.63
C
6
H
4 -4-Ci
C
2
H
5 1.64
C
8
H
4 -4-Ci
C
3
H
7 -n 1.65 C6H 4 -4-CI C3Hri 1.66
C
6
H
4 -4-Ci
C
4
H
9 -t 1.67
C
8
H
4 -4-CI
C
4
H
9 -n 1.68 C6H 4 -4-Ci
CH
2
C
6
H
5 1.69
C
6
H
4 -4-CI
CH
2
C
6
H
4 -4-CH 3 1.70
C
6
H
4 -4-CI
C
6
H
4 -4-CI 1.71
C
6
H
4 -4-Cl
C
6
H
4 -4-OH 1.72
C
6
H
4 -4-CI C6H 4 -2-CH 3 1.73
C
6
H
4 -4-Ci C6H 4 -2-CI 1.74
C
6
H
4 -4-CI
C
6
H
4 -4-Br 1.75
C
6
H
4 -4-Cl 4-pyridyl 1.76 C6H 4 -4-CI COH4-4-OCH 2
..C
6
H
4 .. 3.CF 3 1.77
C
6
H
4 -4-Ci CBH 4
-O-CH
2 F F 1.78 H
C
6
H
5 1.79
C
6
H
5 CH 2
C
6
H
5 1.80
C
2
H
5 -C6H 4 -4-CI D D .1 -22 Table 2: Compounds of the formula H 0 C CH 2 N C I I I F H R, Comp. No. R 1 R2 phys. Data 2.01 H H 2.02 H CH 3 2.03 H C 2
H
5 2.04 H C 3
H
7 -n 2.05 H C 3
H
7 -i 2.06 H C 4
H
9 -n 2.07 H C 4
H
9 -t 2.08 H C 8
H
13 -n 2.09 H CjOH21-n 2.10 H CH 2
C(CH
3
)
3 2.11 CH 3 H 2.12 CH 3
CH
3 2.13 CH 3
C
2
H
5 2.14 CH 3
C
3
H
7 -n 2.15 CH 3
C
3
H
7 -i 2.16 CH 3
C
4
H
9 -n 2.17 CH 3
C
4
H
9 -t 2.18 CH 3
C
6
H
13 -n 2.19 CH 3 C10H21-n 2.20 CH 3
CH
2
C(CH
3
)
3 1v -23 Comp. No. R, R phys. Data 2.21
CH
3 C 6
H
5 2.22
CH
3 C 8
H
4 -2-CI 2.23
CH
3 C 6
H
4 -3-CI 2.24
CH
3 C 6
H
4 -4-CI 2.25
CH
3 C6H 4 -2-CF 3 2.26
CH
3 C 6
H
4 -3-CF 3 2.27
CH
3 C 6
H
4 -4-CF 3 2.28
CH
3 C 6
H
4 -2-CN 2.29
CH
3 C 8
H
4 -3-CN 2.30
CH
3 C 8
H
4 -4-CN 2.31
CH
3 C 6
H
4 -2-N0 2 2.32
CH
3 C 6
H
4 -3-N0 2 2.33
CH
3 C 6
H
4 -4-N0 2 2.34
CH
3 C 8
H
4 -4-C 6
H
5 2.35
CH
3 C 6
H
4 -4-0C 6 Hs 2.36
CH
3 C6H 4 -4-C(CH 3
)
3 2.37
CH
3 C 8
H
4 -4-OCF 3 2.38
CH
3 C 6
H
4 -4-COOC 2
H
5 2.39
CH
3 C6F 5 2.40
CH
3 C6H 2 -3,4,5-(OCH 3
)
3 2.41
CH
3 / N " -24 Comp. No. R 1 R2 phys. Data 2.42
CH
3 2.43
CH
3 S/ OH 2.44 C6H 5 CF 3 2.45 C6H 5
C
2 Hs 2.46 C 6
H
5
C
3
H
7 -n 2.47 C 6 Hs C 3
H
7 -i 2.48 C 6
H
5
C
4
H
9 -t 2.49 C 6
H
5
C
4
H
9 -n 2.50 C 6
H
5 cyclopropyl 2.51 C 6
H
5 cyclopentyl 2.52 C6H 5 cyclohexyl 2.53
C
6
H
5 C 6
H
5 2.54 C 6
H
5
C
6
H
4 -4-CI 2.55 C 6
H
5
C
6
H
4 -4-CF 3 2.56 C 6
H
5 C6H 4 -4-CN 2.57 C 6
H
5 C 6
H
4 -4-NO2 2.58 CH 5 C6H 4 -4-C 6
H
5 2.59 C 6
H
5
C
6
H
4 -4-OC 6
H
5 2.60 C6H 5 C6H 4 -4-C(CH 3
)
3 2.61 C 6
H
5
C
6
H
4 -4-OCF 3 4'j - 25 Comp. No. R, R phys. Data 2.62 C 6
H
4 -4-CI CF 3 2.63 C 6
H
4 -4-CI C 2
H
5 2.64 C6H 4 .. 4-CI C 3 Hrfl 2.65 C 6
H
4 -4-CI C 3 Hri 2.66 C6H 4 -4-CI C 4 Hg-t 2.67 C 8
H
4 -4-CI C 4
H
9 -n 2.68 C 6
H
4 -4-CI CH 2
CBH
5 2.69 C6H 4 -4-CI CH 2
C
6
H
4 -4-CH 3 2.70 C 6
H
4 -4-Cl C 6
H
4 -4-CI 2.71 C6H 4 -4-CI C6H 4 -4-OH 2.72 C 6
H
4 -4-CI C 6
H
4 -2-CH 3 2.73 C6H 4 -4-CI C 6
H
4 -2-CI 2.74 C6H 4 -4-CI C 6
H
4 -4-Br 2.75 C 8
H
4 -4-CI 4-pyridyl 2.76 C 6
H
4 -4-CI -C 6
H
4 -4-QCH 2
-C
8
H
4 -3-CF 3 2.77 C6H 4 -4-CI C 6
H
4 2O- -1 - F F 2.78 H -C 8
H
5 2.79 C 6
H
5
CH
2
C
6
H
5 2.80 C 2
H
5
-C
6
H
4 -4-CI -26 Table 3: Compounds of the formula H 0 H RI I I F C C CH C
,CH
2 'C N N C C 2 0 11 F 0 Comp. No. R1 R2 phys. Data 3.01 H H 3.02 H
CH
3 3.03 H
C
2
H
5 3.04 H
C
3
H
7 -n 3.05 H
C
3
H
7 -i 3.06 H
C
4
H
9 -n 3.07 H
C
4
H
9 -t 3.08 H
C
8
H
13 -n 3.09 H
C
10
H
21 -n 3.10 H
CH
2
C(CH
3
)
3 3.11
CH
3 H 3.12
CH
3 CH 3 3.13
CH
3 C 2
H
5 3.14
CH
3 C 3
H
7 -n 3.15
CH
3 C 3
H
7 -i 3.16
CH
3 C 4 H-n 3.17
CH
3 C 4
H
9 -t 3.18
CH
3 C 8
H
13 -n 3.19
CH
3 C 10
H
21 -n 3.20
CH
3 CH 2
C(CH
3
)
3 C) '-7 -27 Comp. No. RR2phys. Data 3.21 CH 3
C
8
H
5 3.22 CH 3 C6H 4 -2-CI 3.23 CH 3 C6H 4 -3-CI 3.24 CH 3 C6H 4 -4-Cl 3.25
CH
3 C6H 4 -2-CF 3 3.26
CH
3 C6H 4 -3-CF 3 3.27 CH 3
C
6
H
4 -4-CF 3 3.28 CH 3
C
6
H
4 -2-CN 3.29 CH 3 C6H 4 -3-CN 3.30 CH 3 C6H 4 -4-CN 3.31 CH 3
C
6
H
4 -2-N0 2 3.32 CH 3
C
6
H
4 -3-N0 2 3.33 CH 3 C6H 4 -4-N0 2 3.34 CH 3
C
6
H
4 -4-C 6
H
5 3.35
CH
3 C6H 4 -4-0C 6
H
5 3.36
CH
3
C
6
H
4 -4-C(CH 3
)
3 3.37
CH
3
C
6
H
4 -4-OCF 3 3.38 CH 3
C
6
H
4 -4-COOC 2
H
5 3.39
CH
3
C
6
F
5 3.40
CH
3
C
6
H
2 -3,4,5-(OCH 3
)
3 3.41 CH 3 N /-\0 F 1-', -28 Comp. No. R1 R2 phys. Data 3.42 CHa N/ N \=I ~N 3.43
CH
3 \ / OH 3.44 C6Hs CF 3 3.45 C 6
H
5
C
2 H 3.46 C 6
H
5
C
3
H
7 -n 3.47 C 6
H
5
C
3 Hz-i 3.48 C6H 5
C
4
H
9 -t 3.49 C 6
H
5
C
4
H
9 -n 3.50 C6H 5 cyclopropyl 3.51 C 6
H
5 cyclopentyl 3.52 C 6
H
5 cyclohexyl 3.53 C 6
H
5 C6H 5 3.54 C 6 Hs C6H 4 -4-CI 3.55 C 6
H
5
C
6
H
4 -4-CF 3 3.56 C 6
H
5
C
6
H
4 -4-CN 3.57 C6H 5
C
6
H
4 -4-NO2 3.58 C 6
H
5
C
6
H
4 -4-C 6
H
5 3.59 C6H 5
C
6
H
4 -4-OC 6
H
5 3.60 C 6
H
5
C
6
H
4 -4-C(CH 3
)
3 3.61 C 6
H
5
C
6
H
4 -4-OCF 3 -29 Comp. No. RR2phys. Data 3.62
C
6
H
4 -4-Ci
CF
3 3.63
C
6
H
4 -4-CI CAH 3.64
C
6
H
4 -4-CI
C
3
H
7 -n 3.65
C
6
H
4 -4-CI
C
3
H
7 -i 3.66
C
6
H
4 -4-CI
C
4
H
9 -t 3.67
C
8
H
4 -4-CI
C
4
H
9 -n 3.68
C
6
H
4 -4-Cl
CH
2
C
6
H
5 3.69
C
6
H
4 -4-CI
CH
2
C
6
H
4 -4-CH 3 3.70 C6H 4 -4-CI C6H 4 -4-CI 3.71
C
8
H
4 -4-CI
C
6
H
4 -4-OH 3.72
C
6
H
4 -4-Cl C6H 4 -2-CH 3 3.73
C
6
H
4 -4-Ci
C
6
H
4 -2-CI 3.74
C
6
H
4 -4-CI
C
6
H
4 -4-Br 3.75 C6H 4 -4-CI 4-pyridyl 3.76
C
6
H
4 -4-Ci C6H4-4-OCH 2
-C
6
H
4 .. 3.CF 3 3.77 C6H 4 -4-CI
C
6
H
4
-O-CH
2 F F 3.78 H
C
6
H
5 3.79
C
6
H
5 CH 2
C
6
H
5 3.80 CAH
-C
6
H
4 -4-Cl D)4z -30 Table 4: Compounds of the formula H 0 FC- C CH .- CH2 CH .C 01- N - C R, F R2 Comp. No. R 1
R
2 phys. Data 4.1 H H 4.2 H CH 3 n20 = 1.6869 4.3 H C 2
H
5 4.4 H C 3 Hr-n 4.5 H C 3
H
7 -i 4.6 H C 4
H
9 -n 4.7 H C 4
H
9 -t 4.8 H C 6
H
1 3 -n 4.9 H C 1 aH 21 -n 4.10 H CH 2
C(CH
3
)
3 4.11 CH 3 H 4.12 CH 3
CH
3 n20 = 1.6893 4.13 CH 3
C
2
H
5 4.14 CH 3
C
3
H
7 -n 4.15 CH 3
C
3
H
7 -i 4.16 CH 3
C
4
H
9 -n 4.17 CH 3
C
4 Hg-t 4.18 CH 3
C
6
H
1 3 -n 4.19 CH 3 C10H21-n 44/
I-,-'
-31 Comp. No. R 1 R2 phys. Data 4.20
CH
3 CH 2
C(CH
3
)
3 4.21
CH
3 C 6
H
5 nD2 0 = 1.50731 4.22
CH
3 C 6
H
4 -2-Cl Oil 4.23
CH
3 C 6
H
4 -3-Cl nD 20 = 1.6883 4.24
CH
3 C 8
H
4 -4-Cl Oil 4.25
CH
3 C 8
H
4 -2-CF 3 nD 2 0 = 1.4667 4.26
CH
3 C 8
H
4 -3-CF 3 nD 20 = 1.6765 4.27
CH
3 C 6
H
4 -4-CF 3 4.28
CH
3 C6H 4 -2-CN 4.29
CH
3 C 6
H
4 -3-CN amorphous 4.30
CH
3 C6H 4 -4-CN
M.P.
121-128*C 4.31
CH
3 C 6
H
4 -2-NO 2 nD 20 = 1.6888 4.32
CH
3 C 6
H
4 -3-NO 2 nD 20 = 1.6897 4.33
CH
3 C 6
H
4 -4-NO 2 nD20 = 1.6853 4.34
CH
3 CH 4 -4-C 6 Hs m.p.: 51-52*C 4.35
CH
3 C 6
H
4 -4-OC 6
H
5 Oil 4.36
CH
3 C 6
H
4 -4-C(CH 3
)
3 nD2 0 = 1.6754 4.37
CH
3 C6H 4 -4-OCF 3 nD20 = 1.6843 4.38
CH
3 C6H 4 -4-COOC2H 5 amorphous 4.39
CH
3 C 6
F
5 Oil 4.40
CH
3 C6H 2 -3,4,5-(OCH 3
)
3 nD 20 = 1.5207 4.41
CH
3 N amorphous - 32 Comp. No. R 1 R2 phys. Data 4.42 CH 3 N \ \: N 4.43
CH
3 m.p.: 79-81 0 C \ / OH 4.44 C6H 5 CF 3 4.45 C6H 5 C 2
H
5 4.46 C6H 5
C
3
H
7 -n 4.47
C
6
H
5 C 3 H-i Oil 4.48
C
6
H
5
C
4
H
9 -t no20 = 1.4850 4.49 C6H 5
C
4
H
9 -n 4.50
C
6
H
5 cyclopropyl no20 = 1.5132 4.51 C6H 5 cyclopentyl 4.52
C
6
H
5 cyclohexyl 4.53
C
6
H
5 C 6
H
5 nD20 = 1.5503 4.54
C
6
H
5 C 6
H
4 -4-Cl Oil 4.55
C
6
H
5 C 6
H
4 -4-CF 3 no22 = 1.5130 4.56
C
6
H
5 C 8
H
4 -4-CN 4.57
C
6
H
5 C6H 4 -4-NO 2 amorphous 4.58
C
6
H
5 C 6
H
4 -4-C6H 5 4.59
C
6
H
5 C 6
H
4 -4-OC 6
H
5 4.60 C6H 5 C 6
H
4 -4-C(CH 3
)
3 4.61
C
6
H
5 C 6
H
4 -4-OCF 3 ' T RA O/ -TNj -33 Comp. No. R, R phys. Data 4.62 C 6
H
4 -4-CI CF 3 n20= 1.4709 4.63 C 6
H
4 -4-CI C 2 Hs 4.64 C 8
H
4 -4-CI C 3 Hr-n 4.65 C 6
H
4 -4-CI C 3
H
7 -i 4.66 C6H 4 -4-CI C 4 Hq-t 4.67 C 6
H
4 -4-CI C 4
H
9 -n 4.68 C 6
H
4 -4-CI CH 2 C6H 5 4.69 C 6
H
4 -4-CI CH 2
C
6
H
4 -4-CH 3 4.70 C6H 4 -4-CI C6H 4 -4-CI m.p.: 66-67 0 C 4.71 C6H 4 -4-Cl C6H 4 -4-OH 4.72 C 6
H
4 -4-CI C 6
H
4 -2-CH 3 4.73 C6H 4 -4-CI C6H 4 -2-CI 4.74 C 8
H
4 -4-CI C 6
H
4 -4-Br 4.75 C 6
H
4 -4-CI 4-pyridyl nD 20 = 1.5575 4.76 C 6
H
4 -4-CI C 6
H
4 -4-OCH 2
-C
6
H
4 -3-CF 3 4.77
C
6
H
4 -4-CI CH- - I-- F F 4.78 H CA H 5 2 = 1.5131 4.79 CAH CH 2
C
6
H
5 n20= 1.6744 4.80 CAH -C 6
H
4 -4-CI D2 = 1.6768 4.81 CH 3 C6H 3 -3,5-(CF 3
)
2 n20= 1.4509 4.82 cyclopropyl -C 6
H
3 -4-CI D2 = 1.6820 )T J~ -34 Comp. No. R, R2 phys. Data 4 .8 3 C H 3 C -~ N 138-140 0 C
-
CF
3 4.84
CH
3 N' 23 = 1.5350 cl 4 8O2C l 4.85 CH3 n D20 = 1.5568 r O 4.86 CHa 23 = 1.4770 I- ,a O-CF 2
-CHF
2 4.87
C
2
H
5 Cl nD20 4.88 C2Hn N 23 = 1.5113 -aO aCFa 4.89 CH3 nD23 1.5510 0 C
O
4.90
CH
3 N nD23= 1.5282 O F - 35 Comp. No. R 1 R2 phys. Data 4.91 CH 3 N 0-Me nD23 = 1.5110 O CFa 4.92 CH 3 m.p.: 36-37*C
O-CFCHF
2 4.93 CH 3 nD23 = 1.5175 0 4.94 -C 8
H
5
C
8
H
4 -2-F nD26 = 1.5390 4.95 -C 6
H
5 C6H 3 -2,4-F 2 nD26 = 1.5267 4.96 -C 6
H
5
C
8
H
4 -4-F nD = 1.5343 4.97 -C6H 4 -4-F C 6
H
4 -4-F m.p.: 55-57*C 4.98 -C 6
H
5 C6H 4 -3-CF 3 nD 22 = 1.5143 4.99 -C 6
H
4 -3-CF 3 C6H 4 -3-CF 3 nD= 1.4831 4.100 -C 6
H
5 C6H 4 -2-Cl nD2 = 1.5523 4.101 m.p.: 52-54*C 4.102 02N NO2 'P 136-138*C 4.103 -C6H 5
-C
6
H
3 -4-CI-3-NO 2 m.p.: 72-75*C 4.104 -C6H 5
-C
6
H
4 -3-NO 2 nD = 1.5615 4.105 -CHs -C6H 3 -2,4-Cl 2 nD2 = 1.5490 -36 Comp. No. R 1 R2 phys. Data 4.106 -C6H 5 -CsH 4 -4-S-C6H 4 -4-CI nD 23 = 1.5757 4.107 -C6H 5 nD 23 = 1.5058 0 0 F 0 4.108 -C6H 4 -4- -CrH 4 -4-O-CH 3 nD 24 = 1.5578
OCH
3 4.109 -C 6
H
5 /mp.: 44-46 0 C 0 F 4.110 -CeH5 nD 23 = 1.5045 0 F 4.111
-C
6 H4-4-F 0 nD 23 = 1.5000 0 F F 4.1112CH-- no 23 4 1.50600 0 - 37 Table 5: Compounds of the formula H 0 C C CH CH 2 CH C N N C R l I FI F H R2 Comp. No. R 1 R2 phys. data 5.1 H H 5.2 H CH 3 m.p.: 78-79 0 C 5.3 H
C
2
H
5 5.4 H C 3
H
7 -n 5.5 H
C
3
H
7 -i 5.6 H C 4
H
9 -n 5.7 H
C
4
H
9 -t 5.8 H
C
6
H
13 -n 5.9 H C10H21-n 5.10 H
CH
2
C(CH
3
)
3 5.11 CH 3 H 5.12 CH 3
CH
3 nD20 = 1.7589 5.13 CH 3
C
2
H
5 5.14 CH 3
C
3
H
7 -n 5.15
CH
3 C 3
H
7 -i 5.16 CH 3
C
4
H
9 -n 5.17 CH 3
C
4
H
9 -t 5.18 CH 3
C
6
H
13 -n -38 Comp. No. R, R phys. data 5.19 CH 3
C
10
H
21 -n 5.20
CH
3
CH
2
C(CH
3
)
3 5.21 CH 3
C
6
H
5 m.p.: 64-66 0 C 5.22 CH 3
C
8
H
4 -2-CI m.p.: 79-82 0 C 5.23 CH 3
C
8
H
4 -3-CI m.p.: 75-78 0 C 5.24 CH 3
C
6
H
4 -4-CI m.p.: 104-106 0 C 5.25 CH 3
C
6
H
4 -2-CF 3 n20= 1.4941 5.26 CH 3
C
6
H
4 -3-CF 3 m.p.: 82-83 0 C 5.27 CH 3 C6H 4 -4-CF 3 m.p.: 68-69*C 5.28 CH 3
C
6
H
4 -2-CN 5.29 CH 3 C6H 4 -3-CN m.p.: 123-124 0 C 5.30 CH 3
C
6
H
4 -4-CN 5.31 CH 3 C6H 4 -2-N0 2 m.p.: 80-84 0 C 5.32 CH 3
C
6
H
4 -3-N0 2 m.p.: 129-130 0 C 5.33 CH 3
C
6
H
4 -4-N0 2 m.p.: 159-161 0 C 5.34 CH 3
C
6
H
4 -4-C 6
H
5 m.p.: 193-195 0 C 5.35 CH 3
C
6
H
4 -4-0C 6
H
5 m.p.: 108-109 0 C 5.36 CH 3
C
6
H
4 -4-C(CH 3
)
3 m.p.: 106-108 0 C 5.37 CH 3
C
6
H
4 -4-OCF 3 m.p.: 93-94 0 C 5.38 CH 3
C
6
H
4 -4-COOC 2
H
5 m. p.: 98-101 0 C 5.39 CH 3
C
6
F
5 m.p.: 119-124 0 C 5.40 CH 3
C
6
H
2 -3,4,5-(OCH 3
)
3 m.p.: 106-108 0 C 5.41 CH 3 N m.p.: 145-146 0
C
-39 Comp. No. R,
R
2 phys. data 5.42
CH
3 ~N ~m.p.: 138-140 0 C 5.43
CH
3 m.p.: 132-133 0 C 5.44
-C
6
H
5 CF 3 5.45
-C
8
H
5 C 2
H
5 5.46
-C
6
H
5 C 3
H
7 -n 5.47
-C
6
H
5 C 3
H
7 -i 5.48 -C6H 5 C 4
H
9 -t m.p.: 38-39*C 5.49 -C6H 5 C 4
H
9 -n 5.50
-C
6
H
5 cyclopropyl nD 2 0 =1.5962 5.51
-C
6
H
5 cyclopentyl 5.52
-C
6 Hs cyclohexyl 5.53
-C
8
H
5 C 6
H
5 m. p.: 70-71 0 C 5.54
-C
6
H
5 C 6
H
4 -4-CI m.p.: 129-131 0 C 5.55 -C6H 5 C 6
H
4 -4-CF 3 m.p.: 1 19-120 0 C 5.56
-C
8
H
5 C 6
H
4 -4-CN 5.57
-C
8
H
5 C 6
H
4 -4-N0 2 M.P.: 88-90 0 C 5.58 -C6H 5 C 6
H
4 -4-C 6
H
5 m.p.: 130-132 0 C 5.59
-C
6
H
5 C 6
H
4 -4-0C6H 5 5.60
-C
6
H
5 C 6
H
4 -4-C(CH 3
)
3 5.61 -C6H 5 C6H 4 -4-OCF 3 RAj -40 Comp. No. R, R phys. data 5.62
-C
6
H
4 -4-CI
CF
3 5.63
-C
8
H
4 -4-CI
C
2
H
5 5.64
-C
6
H
4 -4-Cl
C
3
H
7 -n 5.65
-C
6
H
4 -4-CI C 3
H
7 -i 5.66 -C6H 4 -4-CI C 4
H
9 -t 5.67 -C 8
H
4 -4-CI C 4
H
9 -n 5.68
-C
6
H
4 -4-CI
CH
2 C6H 5 5.69 -C6H 4 -4-CI
CH
2 CrH 4 -4-CH 3 5.70
-C
6
H
4 -4-CI -C 6
H
4 -4-CI m.p.: 114-1 16 0 C 5.71 -C6H 4 -4-CI -C 8
H
4 -4-OH 5.72
-C
6
H
4 -4-CI -C 6
H
4 -2-CH 3 5.73 -C 6
H
4 -4-CI -C 6
H
4 -2-CI 5.74 -C 6
H
4 -4-CI -C 6
H
4 -4-Br 5.75
-C
6
H
4 -4-CI 4-pyridyl m-p.: 144-148 0 C 5.76 -C6H 4 -4-CI -C 6
H
4 -4-OCH 2 -C6H 4 -3-CF 3 Resin 5.77
-C
6
H
4 -4-CI CSH 4 -O-0H 2 - -FResin F 5.78 H
-C
6
H
5 m.p.: 60-63 0 C 5.79 -C6H 5 -CH 2
C
6
H
5 m.p.: 95-96*C 5.80
-C
2 Hs
-C
6
H
4 -4-CI m.p.: 106-107 0 C 5.81 -C 6
H
4 -4-CI -C 6
H
4 -4-OSO 2
N(CH
3
)
2 m.p.: 105-115 0 C 5.82 m.p.: 151-155 0 C Cl CI -41 Comp. No. R, R phys. data 5.83
-C
8
H
5 cyclopropyl m.p.: 80-82 0 C 5.84
-CH
3 -C6H 3 -3,5-(CF 3
)
2 m.p.: 103-105*C 5.85
-C
6
H
5 -C 6
H
4 -4-F m.p.: 77-78*C 5.86 -CeH 5 -C 8
H
3 -2,4-F 2 M.P.: 109-1 10*C 5.87 CH5-C 6
H
4 -4-F M.P.: 99-101 T 5.88
-C
6
H
4 -4-F -C6H 4 -4-F m.p.: 76-77*C 5.89 m.p.: 130-132 0 C 5.90 -C 6
H
5 -C 6
H
4 -3-N0 2 m.p.: 102-106'C 5.91 -C 6
H
5
-C
6
H
4 -3-CF 3 m.p.: 49-50*C 0-Et 5.92 -C 6
H
5 - cm.p.: 81-820C 5.93
-C
6
H
4 -3-CF 3
-C
6
H
4 -3-CF 3 m.p.: 62-63 0 C 5.94
-C
6
H
4 -4-OCH 3 -C6H 4 -4-OCH 3 m.p.: 82-830C 5.95 -C6H 4 -4-OCH 3
-CH
2
-C
6
H
4 -4-OCH 3 m.p.: 123-124*C 5.96
-C
6
H
5 -C 6
H
4 -2-CI m.p.: 69-70 0 C 5.97
-C
6
H
5
-C
6
H
3 -2,4-CI 2 m.p.: 117-1 18 0 C 5.98 -C6H 4 -4-N(CH 3
)
2
-C
6
H
4 -4-N(CH 3
)
2 m.p.: 93-94 0 C 5.99
-C
6 Hs
-C
8
H
4 -4-S-C6H 4 -4-CH 3 m.p.: 112-11 3 0 C 0-me 5.100 -. *6F5 n20= 1.5510 -42 Comp. No. R 1 R2 phys. data 5.101 -C 6
H
5 0 Asobutyl 20 1.5355 Thble 6: Compounds of the formula H 0 H RI F C C CH C H2
C
H C 0CH C N N C R 2 F 0 Comp. No. R1 R2 phys. data 6.1 H H 6.2 H CH 3 nD 20 = 1,6815 6.3 H C 2
H
5 6.4 H C 3
H
7 -n 6.5 H
C
3
H
7 -i 6.6 H C 4
H
9 -n 6.7 H C 4
H
9 -t 6.8 H C 6
H
13 -n 6.9 H C 10
H
21 -n 6.10 H
CH
2
C(CH
3
)
3 6.11 CH 3 H 6.12 CH 3
CH
3 amorphous 6.13
CH
3 C 2
H
5 6.14 CH 3
C
3
H
7 -n R A>/ -43 Comp. No. R, R phys. data 6.15 CH 3 C3Hr-i 6.16 CH 3
C
4
H
9 -n 6.17 OH 3
C
4 Hq-t 6.18 CH 3 C6H 13 -n 6.19 OH 3 Co2 6.20
CH
3
CH
2
C(CH
3
)
3 6.21 OH 3
C
6
H
5 m.p.: 92-94*C 6.22 OH 3
C
8
H
4 -2-CI m.p.: 58-60"C 6.23 CH 3
C
6
H
4 -3-CI m.p.: 126-127*C 6.24 CH 3
C
8
H
4 -4-CI m.p.: 125-127 0 C 6.25 OH 3
C
8
H
4 -2-CF 3 m.p.: 62-64*C 6.26 CH 3
C
6
H
4 -3-CF 3 m.p.: 148-149 0 C 6.27 CH 3
C
6
H
4 -4-CF 3 m.p.: 103-1040C 6.28 OH 3
C
6
H
4 -2-CN 6.29 OH 3
C
8
H
4 -3-CN m.p.: 130-131*C 6.30 OH 3
C
6
H
4 -4-CN m.p.: 141-1420C 6.31 OH 3
C
6
H
4 -2-N0 2 m.p.: 81-84*C 6.32 OH 3
C
6
H
4 -3-N0 2 m.p.: 150-152*C 6.33 OH 3
C
6
H
4 -4-N0 2 m.p.: 147-1490C 6.34 OH 3 C6H 4 -4-C 8
H
5 m.p.: 166-167*C 6.35 OH 3
C
8
H
4 -4-0O 6
H
5 M.P.: 10O-1100O 6.36 OH 3
O
6
H
4 -4-O(0H 3
)
3 m.p.:157-158 0 C 6.37 OH 3 C6 H 4 -4-00F 3 m.p.: 114-116*C 6.38 OH 3
C
6
H
4 -4-0000 2
H
5 m.p.: 127-1290C -44 Comp. No. R 1 R2 phys. data 6.39 CH 3
C
6
F
5 m.p.: 73-76 0 C 6.40 CH 3 C6H 2 -3,4,5-(OCH 3
)
3 m.p.: 139-141*C 6.41 CH 3 / \ m.p.: 142-144 0 C 6.42
CH
3 NAN m.p.: 146-148 0 C ~N 6.43 CH 3 m.p.: 168-170 0 C 4OH 6.44
C
6
H
5 CF 3 6.45
C
8
H
5
C
2
H
5 6.46
C
6
H
5
C
3
H
7 -n 6.47 C6H 5
C
3
H
7 -i n 0 2 0 = 1.6978 6.48
C
6
H
5
C
4
H
9 -t no20 = 1.6988 6.49 C6Hs
C
4
H
9 -n 6.50
C
6
H
5 cyclopropyl m.p.: 60-62 0 C 6.51 C 8
H
5 cyclopentyl 6.52
C
6
H
5 cyclohexyl 6.53 C6H 5
C
6
H
5 m.p.:. 50-53 0 C 6.54
C
6
H
5
C
6
H
4 -4-Cl m.p.: 102-102 0 C 6.55
C
6
H
5 C 6
H
4 -4-CF 3 6.56 C6H 5
C
6
H
4 -4-CN 6.57
C
6
H
5 C 6
H
4 -4-NO2 rN)41 -45 Comp. No. R, R phys. data 6.58
C
6
H
5 C6H 4 -4-C6H 5 6.59
C
6
H
5
C
8
H
4 -4-0C6H 5 6.60
C
8
H
5 C6H 4 -4-C(CH 3
)
3 6.61
C
8
H
5 C6H 4 -4-OCF 3 6.62
C
8
H
4 -4-CI
CF
3 6.63
C
6
H
4 -4-CI C 2 Hs 6.64
C
6
H
4 -4-CI C 3 Hr-n 6.65 Cr 8
H
4 -4-CI C 3
H
7 -i 6.66 C6H 4 -4-CI C 4
H
9 -t 6.67 C6H 4 -4-CI C 4
H
9 -n 6.68
C
6
H
4 -4-CI CH 2 C6H 5 6.69 C6H 4 -4-CI CH 2
C
6
H
4 -4-CH 3 6.70
C
6
H
4 -4-CI C 6
H
4 -4-CI m.p.: 73-75 0 C 6.71
C
6
H
4 -4-CI C6H 4 -4-OH 6.72 C6H 4 -4-CI C6H 4 -2-CH 3 6.73
C
6
H
4 -4-CI C 6
H
4 -2-CI 6.74
C
6
H
4 -4-CI C 6
H
4 -4-Br 6.75 C6H 4 -4-CI 4-pyridyl 6.76 C6H 4 -4-CI CrH 4 -4-OCH 2
-C
8
H
4 -3
CF
3 6.77
C
6
H
4 -4-CI CH- - .I - F F 6.78 H
-C
6
H
5 m.p.: 72-75 0 C 6.79
C
8
H
5
-CH
2
C
6
H
5 m-p.: 104-106 0 C 7') 04 -46 Comp. No. R 1
R
2 phys. data 6.80
C
2
H
5
-C
6
H
4 -4-Cl m.p.: 79-80*C 6.81
CH
3 -C 6
H
3 -3,5-(CF 3
)
2 m.p.: 148-150 0 C 6.82
C
2
H
5
-C
6
H
4 -4-Cl m.p.: 79-80 0 C Table 7: Compounds of the formula H F c CH. C,_ "N "R, C CH 2 L CH 2C C I 1 F
R
2 Comp. No. R 1 R2 phys. data 7.01 H H 7.02 H
CH
3 7.03 H
C
2
H
5 7.04 H
C
3
H
7 -n 7.05 H
C
3
H
7 -i 7.06 H
C
4
H
9 -n 7.07 H
C
4
H
9 -t 7.08 H
C
6 H1 3 -n 7.09 H C10H21-n 7.10 H
CH
2
C(CH
3
)
3 7.11
CH
3 H 7.12
CH
3 CH 3 7.13
CH
3 C 2
H
5 7.14
CH
3 C 3
H
7 -n
A
-47 Comp. No. R, R phys. data 7.15 CH 3
C
3 Hr-i 7.16 CH 3
C
4 H.-n 7.17 CH 3
C
4
H
9 -t 7.18 CH 3
C
6
H
13 -n 7.19 CH 3
C
10
H
21 -n 7.20 CH 3
CH
2
C(CH
3
)
3 7.21 CH 3
C
6
H
5 7.22 CH 3 C6H 4 -2-CI 7.23 CH 3
C
6
H
4 -3-CI 7.24 CH 3
C
6
H
4 -4-Cl 7.25 CH 3
C
6
H
4 -2-CF 3 7.26 CH 3
C
8
H
4 -3-CF 3 7.27
CH
3
C
6
H
4 -4-CF 3 7.28 CH 3
C
6
H
4 -2-CN 7.29 CH 3 C6H 4 -3-CN 7.30 CH 3 C6H 4 -4-CN 7.31 CH 3
C
6
H
4 -2-N0 2 7.32 CH 3
C
6
H
4 -3-N0 2 7.33 CH 3 C6H 4 -4-N0 2 7.34 CH 3
C
6
H
4 -4-C6H 5 7.35 CH 3
C
6
H
4 -4-0C 6
H
5 7.36
CH
3
C
6
H
4 -4-C(CH 3
)
3 7.37
CH
3 C 6
H
4 -4-OCF 3 7.38 CH 3
C
6
H
4 -4-COOC 2
H
5 -48 Comp. No. R 1 R2 phys. data 7.39 CH 3 C6F 5 7.40
CH
3 C 6
H
2 -3,4,5-(OCH 3
)
3 7.41
CH
3 N -- \ O 7.42
CH
3 N 7.43
CH
3 \ / OH 7.44
C
6
H
5 CF 3 7.45 C 6
H
5
C
2
H
5 7.46 C 6
H
5
C
3
H
7 -n 7.47
C
6
H
5 C 3
H
7 -i 7.48 C 6
H
5
C
4
H
9 -t 7.49 C 8
H
5
C
4
H
9 -n 7.50 C 6
H
5 cyclopropyl 7.51 C 6
H
5 cyclopentyl 7.52 C 6
H
5 cyclohexyl 7.53
C
6
H
5 C6H 5 7.54
C
6 Hs
C
6
H
4 -4-Cl 7.55
C
6
H
5 C 6
H
4 -4-CF 3 7.56
C
6
H
5
C
6
H
4 -4-CN 7.57
C
6
H
5 C6H 4 -4-NO2 -49 Comp. No. R, R phys. data 7.58
C
6
H
5 C 6
H
4 -4-C 6
H
5 7.59
C
6
H
5 C 8
H
4 -4-0C 6
H
5 7.60
C
6
H
5 C 6
H
4 -4-C(CH 3
)
3 7.61
C
6
H
5 C 6
H
4 -4-OCF 3 7.62
C
6
H
4 -4-CI
CF
3 7.63
C
6
H
4 -4-CI
C
2
H
5 7.64
C
6
H
4 -4-CI
C
3
H
7 -n 7.65
C
6
H
4 -4-CI
C
3 H7-i 7.66
C
6
H
4 -4-CI
C
4
H
9 -t 7.67
C
6
H
4 -4-CI
C
4
H
9 -n 7.68
C
6
H
4 -4-CI
CH
2 C6H 5 7.69
C
6
H
4 -4-CI
CH
2
C
6
H
4 -4-CH 3 7.70
C
6
H
4 -4-Ci
C
6
H
4 -4-Cl 7.71
C
6
H
4 -4-CI C6H 4 -4-OH 7.72
C
6
H
4 -4-CI
C
6
H
4 -2-CH 3 7.73
C
6
H
4 -4-CI C6H 4 -2-CI 7.74
C
6
H
4 -4-CI
C
8
H
4 -4-Br 7.75
C
6
H
4 -4-CI 4-pyridyl 7.76 C6H 4 -4-CI
C
6
H
4 -4-OCH 2 -C6H 4 -3-.
CF
3 7.77
C
6
H
4 -4-CI
C
6 H 4
-O-CH
2 F F 7.78 H C6 H 5 7.79 C6H 5 CH 2 C6H5 - 50 Comp. No. R 1 R2 phys. data 7.80
C
2
H
5 -C 6
H
4 -4-CI Table 8: Compounds of the formula H 0 F '*I '5 C H 2 , C , 1 N RI C C 2 J 2c2 N I I I F H R 2 Comp. No. R 1 R 2 phys. data 8.01 H H 8.02 H
CH
3 8.03 H
C
2
H
5 8.04 H
C
3
H
7 -n 8.05 H
C
3
H
7 -i 8.06 H
C
4
H
9 -n 8.07 H
C
4
H
9 -t 8.08 H C6H 13 -n 8.09 H
C
10
H
21 -n 8.10 H
CH
2
C(CH
3
)
3 8.11
CH
3 H 8.12
CH
3 CH 3 8.13
CH
3 C 2
H
5 8.14
CH
3 C 3
H
7 -n 8.15
CH
3 C 3
H
7 -i 8.16
CH
3 C 4
H
9 -n 414 - 51 Comp. No. R, R phys. data 8.17
CH
3 C 4
H
9 -t 8.18
CH
3 C 6 Hl 3 -n 8.19
CH
3 C 10
H
21 -n 8.20
CH
3 CH 2
C(CH
3
)
3 8.21
CH
3 C 6
H
6 8.22
CH
3 C 6
H
4 -2-CI 8.23
CH
3 C6H 4 -3-CI 8.24
CH
3 C6H 4 -4-CI 8.25
CH
3 C 6
H
4 -2-CF 3 8.26
CH
3 C 6
H
4 -3-CF 3 8.27
CH
3 C 6
H
4 -4-CF 3 8.28
CH
3 C 6
H
4 -2-CN 8.29
CH
3 C6H 4 -3-CN 8.30
CH
3 C 6
H
4 -4-CN 8.31
CH
3 C 6
H
4 -2-N0 2 8.32
CH
3 C6H 4 -3-N0 2 8.33
CH
3 C 6
H
4 -4-N0 2 8.34
CH
3 C6H 4 -4-C 6
H
5 8.35
CH
3 C 6
H
4 -4-0C 6
H
5 8.36
CH
3 C 8
H
4 -4-C(CH 3
)
3 8.37
CH
3 C 6
H
4 -4-OCF 3 8.38
CH
3 C 6
H
4 -4-COOC 2
H
5 8.39
CH
3 C 6
F
5 8.40
CH
3 C6H 2 -3,4,5-(OCH 3
)
3 - 52 Comp. No. R 1 R2 phys. data 8.41 CH 3 N \ 8.42
CH
3 N -N 8.43
CH
3 \ / OH 8.44
C
6 Hs
CF
3 8.45
C
6
H
5 C 2
H
5 8.46 C 6
H
5
C
3
H
7 -n 8.47
C
6
H
5 C 3
H
7 -i 8.48 C6H 5
C
4
H
9 -t 8.49 C 6
H
5
C
4
H
9 -n 8.50 C 6
H
5 cyclopropyl 8.51 C 8
H
5 cyclopentyl 8.52 C 6
H
5 cyclohexyl 8.53
C
6
H
5
C
6
H
5 8.54 CHs C 6
H
4 -4-CI 8.55 CHs C6H 4 -4-CF 3 8.56 CHs
C
8
H
4 -4-CN 8.57
C
8 Hs
C
6
H
4 -4-NO2 8.58 CHs
C
8
H
4 -4-C6H 5 8.59 CHs C6H 4 -4-OC6H 5 - 53 Comp. No. R, R 2 phys. data 8.60 C 8
H
5
C
6
H
4 -4-C(CH 3
)
3 8.61 CrH 5
C
6
H
4 -4-OCF 3 8.62 C 6
H
4 -4-CI CF 3 8.63 C 6
H
4 -4-CI CAH 8.64 C 8
H
4 -4-CI C 3 Hr-n 8.65 C 6
H
4 -4-CI C 3
H
7 -i 8.66 C 6
H
4 -4-CI C 4
H
9 -t 8.67 C 6
H
4 -4-CI C 4
H
9 -n 8.68 C 6
H
4 -4-Cl CH 2
C
6
H
5 8.69 C 6
H
4 -4-CI CH 2
C
6
H
4 -4-CH 3 8.70 C 6
H
4 -4-CI C6H 4 -4-CI 8.71 C 6
H
4 -4-Cl C 6
H
4 -4-OH 8.72 C 6
H
4 -4-CI C 6
H
4 -2-CH 3 8.73 C 6
H
4 -4-CI C 6
H
4 -2-CI 8.74 C 6
H
4 -4-CI C 8
H
4 -4-Br 8.75 C 6
H
4 -4-CI 4-pyridyl 8.76 CrH 4 -4-CI C 8
H
4 -4-OCH 2
-C
8
H
4 -3-CF 3 8.77
C
6
H
4 -4-CI C 6
H
4
-O-CH
2 -q F F 8.78 H -C6Hs 8.79 C 6
H
5
-CH
2
C
6
H
5 8.80 C 2
H
5
-C
6
H
4 -4-CI
NT
-54 Table 9: Compounds of the formula H 0 H RI F C CHf H C2,CH ,O "CH2 N C N F O1 Comp. No. R 1 R2 phys. data 9.01 H H 9.02 H
CH
3 9.03 H
C
2
H
5 9.04 H
C
3
H
7 -n 9.05 H
C
3
H
7 -i 9.06 H C 4
H
9 -n 9.07 H
C
4
H
9 -t 9.08 H
C
6
H
13 -n 9.09 H C1H21-n 9.10 H
CH
2
C(CH
3
)
3 9.11
CH
3 H 9.12
CH
3 CH 3 9.13
CH
3
C
2
H
5 9.14
CH
3
C
3
H
7 -n 9.15
CH
3 C 3
H
7 -i 9.16
CH
3
C
4
H
9 -n 9.17
CH
3
C
4
H
9 -t 9.18
CH
3
C
6
H
13 -n 9.19
CH
3
C
10
H
21 -n 9.20
CH
3 CH 2
C(CH
3
)
3 -55 Comp. No. R, R 2 phys. data 9.21
CH
3
C
8
H
5 9.22
CH
3
C
8
H
4 -2-CI 9.23
CH
3
C
6
H
4 -3-CI 9.24
CH
3 C6H 4 -4-CI 9.25
CH
3 C 6
H
4 -2-CF 3 9.26
CH
3
C
6
H
4 -3-CF 3 9.27
CH
3 C 6
H
4 -4-CF 3 9.28
CH
3
C
6
H
4 -2-CN 9.29
CH
3
C
6
H
4 -3-CN 9.30
CH
3
C
6
H
4 -4-CN 9.31
CH
3
C
8
H
4 -2-N0 2 9.32
CH
3 C6H 4 -3-N0 2 9.33
CH
3 C6H 4 -4-N0 2 9.34
CH
3 C6H 4 -4-C 6
H
5 9.35
CH
3
C
6
H
4 -4-0C 6
H
5 9.36
CH
3
C
6
H
4 -4-C(CH 3
)
3 9.37
CH
3 C 6
H
4 -4-OCF 3 9.38
CH
3
C
6
H
4 -4-COOC 2
H
5 9.39
CH
3
C
6
F
5 9.40
CH
3 C6H 2 -3,4,5-(OCH 3
)
3 9.41
CH
3 N O 57, -56 Comp. No. R, R phys. data 9.42
CH
3 -&~j N/:jZl 9.43
CH
3 -0 9.44 C6H 5
CF
3 9.45 CAH C 2
H
5 9.46 CAH C 3
H
7 -n 9.47
C
6 Hs C 3
H
7 -i 9.48 CAH C 4
H
9 -t 9.49 CAH C 4
H
9 -n 9.50 CAH cyclopropyl 9.51 CAH cyclopentyl 9.52 CAH cyclohexyl 9.53 C6H 5
C
6
H
5 9.54 CAH C6H 4 -4-CI 9.55
C
6
H
5
C
6
H
4 -4-CF 3 9.56 CAH C 6
H
4 -4-CN 9.57 CAH C 6
H
4 -4-N0 2 9.58 CAH C 6
H
4 -4-C 6
H
5 9.59
C
6
H
5 C6H 4 -4-0C 6
H
5 9.60 CAH C 6
H
4 -4-C(CH 3
)
3 9.61 C6H 5
C
6
H
4 -4-OCF 3 Q -1 - 57 Comp. No. R, R phys. data 9.62
C
6
H
4 -4-CI CF 3 9.63
C
6
H
4 -4-CI C 2
H
5 9.64
C
6
H
4 -4-CI C 3
H
7 -n 9.65 C6H 4 -4-CI C 3
H
7 -i 9.66
C
6
H
4 -4-CI C 4 Hq-t 9.67
C
6
H
4 -4-CI C 4
H
9 -n 9.68
C
6
H
4 -4-CI CH 2
C
6
H
5 9.69
C
6
H
4 -4-CI CH 2 C6H 4 -4-CH 3 9.70
C
8
H
4 -4-CI C 6
H
4 -4-CI 9.71 C 6
H
4 -4-CI C6H 4 -4-OH 9.72
C
6
H
4 -4-CI C 6
H
4 -2-CH 3 9.73
C
6
H
4 -4-CI C 6
H
4 -2-CI 9.74
C
8
H
4 -4-CI C 6
H
4 -4-Br 9.75
C
6
H
4 -4-CI 4-pyridyl 9.76
C
6
H
4 -4-CI -C6H 4 -4-OCH 2 -C6H 4 -3
CF
3 CH-O- CH 2 9.77 C 6
H
4 -4-CI 6 -1 F F 9.78 H C 6
H
5 9.79 C6H 5
CH
2 C6H 5 9.80
C
2
H
5
-C
6
H
4 -4-CI RAI4, - 58 Table 10: Compounds of the formula H 0 F C CH 2 CH O N R F Comp. No. R 1 R2 phys. data 10.01 H H 10.02 H
CH
3 10.03 H
C
2
H
5 10.04 H C 3
H
7 -n 10.05 H
C
3
H
7 -i 10.06 H C 4
H
9 -n 10.07 H C 4
H
9 -t 10.08 H C 6
H
13 -n 10.09 H C10H21-n 10.10 H
CH
2
C(CH
3
)
3 10.11
CH
3 H 10.12
CH
3 CH 3 10.13 CH 3
C
2
H
5 10.14
CH
3 C 3
H
7 -n 10.15
CH
3 C 3
H
7 -i 10.16 CH 3
C
4
H
9 -n 10.17
CH
3
C
4
H
9 -t 10.18 CH 3
C
6
H
13 -n 10.19
CH
3
C
10
H
21 -n LU I -fT -59 Comp. No. R 1 R2 phys. data 10.20
CH
3
CH
2
C(CH
3
)
3 10.21
CH
3 C 6
H
5 10.22 CH 3
C
6
H
4 -2-CI 10.23 CH 3 C6H 4 -3-Cl 10.24 CH 3 C6H 4 -4-Cl 10.25
CH
3 C 6
H
4 -2-CF 3 10.26
CH
3 C 6
H
4 -3-CF 3 10.27
CH
3 C 6
H
4 -4-CF 3 10.28 CH 3
C
6
H
4 -2-CN 10.29 CH 3
C
8
H
4 -3-CN 10.30 CH 3
C
6
H
4 -4-CN 10.31 CH 3
C
6
H
4 -2-NO2 10.32
CH
3 C 6
H
4 -3-NO2 10.33
CH
3 C6H 4 -4-NO2 10.34
CH
3 C6H 4 -4-C 6
H
5 10.35
CH
3 C6H 4 -4-OC 6
H
5 10.36
CH
3 C 6
H
4 -4-C(CH 3
)
3 10.37
CH
3 C 6
H
4 -4-OCF 3 10.38
CH
3 C 6
H
4 -4-COOC 2
H
5 10.39
CH
3 C6F 5 10.40
CH
3 C 6
H
2 -3,4,5-(OCH 3
)
3 10.41 CH 3 N 0 INN 4' 041
VT-
-60 Comp. No. R 1 R2 phys. data 10.42
CH
3 N \N 10.43
CH
3 \ / OH 10.44 C6H 5 CF 3 10.45
C
6
H
5 C 2
H
5 10.46
C
6
H
5 C 3
H
7 -n 10.47
C
6
H
5 C 3
H
7 -i 10.48 C 6
H
5
C
4
H
9 -t 10.49 C6H 5
C
4
H
9 -n 10.50
C
6
H
5 cyclopropyl 10.51
C
6
H
5 cyclopentyl 10.52
C
6
H
5 cyclohexyl 10.53
C
6
H
5 C6H 5 10.54
C
6
H
5 C 6
H
4 -4-Cl 10.55
C
6
H
5 C 6
H
4 -4-CF 3 10.56
C
6
H
5 C 6
H
4 -4-CN 10.57
C
6
H
5 C6H 4 -4-NO2 10.58
C
6
H
5 C 6
H
4 -4-C6H 5 10.59
C
6
H
5 C 6
H
4 -4-OC 6 Hs 10.60 C6H 5 C 6
H
4 -4-C(CH 3
)
3 10.61
C
6
H
5 C 6
H
4 -4-OCF 3 -T/ )b)J -61 Comp. No. R, R phys. data 10.62
C
6
H
4 -4-CI
CF
3 10.63 C6H 4 -4-CI C 2
H
5 10.64 C6H 4 -4-CI C 3 Hr-n 10.65 C6H 4 -4-CI C 3 Hr-i 10.66 C 6
H
4 -4-CI C 4
H
9 -t 10.67 C 6
H
4 -4-CI C 4 Hg..n 10.68
C
6
H
4 -4-CI CH 2
C
6
H
5 10.69
C
6
H
4 -4-CI CH 2
C
6
H
4 -4-CH 3 10.70
C
6
H
4 -4-CI C 6
H
4 -4-CI 10.71 C6H 4 -4-CI C 6
H
4 -4-OH 10.72
C
6
H
4 -4-CI C6H 4 -2-CH 3 10.73
C
6
H
4 -4-CI C 6
H
4 -2-CI 10.74 C6H 4 -4-CI C 6
H
4 -4-Br 10.75
C
6
H
4 -4-CI 4-pyridyl 10.76
C
6
H
4 -4-Cl C6H 4 -4-OCH 2
-C
6
H
4 -3-CF 3 10.77
C
6
H
4 -4-CI
C
6
H
4
-O-CH
2 - -F F 10.78 H
C
6
H
5 10.79
C
6
H
5 CH 2
C
6
H
5 10.80
C
2
H
5 -CsH 4 -4-CI
C),
-62 Table 11: Compounds of the formula H 0 F c FH 2 14,zzzN RI C CH 2 C 3 N c F H Comp. No. R 1 R2 phys. data 11.01 H H 11.02 H
-CH
3 11.03 H
-C
2
H
5 11.04 H -C 3 Hrn 11.05 H
-C
3
H
7 -i 11.06 H -C 4
H
9 -n 11.07 H -C 4
H
9 -t 11.08 H -C 6
H
13 -n 11.09 H -CoH21-n 11.10 H
-CH
2
C(CH
3
)
3 11.11
CH
3 H 11.12
CH
3 -CH 3 11.13 CH 3
-C
2
H
5 11.14
CH
3
-C
3
H
7 -n 11.15
CH
3 -C 3
H
7 -i 11.16 CH 3
-C
4
H
9 -n 11.17 CH 3
-C
4
H
9 -t 11.18
CH
3 -C6H 13 -n 11.19
CH
3
-C
10
H
21 -n V0/ -63 Comp. No. R 1 R2 phys. data 11.20
CH
3
-CH
2
C(CH
3
)
3 11.21 CH 3
-C
6
H
5 11.22 CH 3 -C6H 4 -2-CI 11.23 CH 3
-C
6
H
4 -3-Cl 11.24 CH 3
-C
6
H
4 -4-Cl 11.25
CH
3
-C
8
H
4 -2-CF 3 11.26
CH
3
-C
6
H
4 -3-CF 3 11.27
CH
3
-C
6
H
4 -4-CF 3 11.28 CH 3
-C
6
H
4 -2-CN 11.29 CH 3
-C
8
H
4 -3-CN 11.30 CH 3
-C
6
H
4 -4-CN 11.31
CH
3
-C
6
H
4 -2-NO2 11.32
CH
3 -C6H 4 -3-NO2 11.33
CH
3
-C
8
H
4 -4-NO2 11.34
CH
3 -C6H 4 -4-CH 5 11.35 CH 3
-C
6
H
4 -4-OC 6
H
5 11.36
CH
3
-C
6
H
4 -4-C(CH 3
)
3 11.37
CH
3
-C
6
H
4 -4-OCF 3 11.38
CH
3 -C6H 4 -4-COOC 2
H
5 11.39
CH
3
C
8
F
5 11.40
CH
3
-C
6
H
2 -3,4,5-(OCH 3
)
3 11.41 CH 3 N 0 LLN O 7\-- -64 Comp. No. R 1 R2 phys. data 11.42
CH
3 a /\ -N 11.43
CH
3 \ / OH 11.44 C6H 5 -CF 3 11.45
C
6
H
5 -C2H5 11.46
C
6
H
5
-C
3 Hrn 11.47
C
6
H
5
-C
3
H
7 -i 11.48 C 6
H
5
-C
4
H
9 -t 11.49
C
6
H
5
-C
4
H
9 -n 11.50
C
6
H
5 cyclopropyl 11.51 C6H 5 cyclopentyl 11.52
C
6
H
5 cyclohexyl 11.53
C
6
H
5 -C 6
H
5 11.54
C
6
H
5
-C
6
H
4 -4-CI 11.55
C
6
H
5 -C 8
H
4 -4-CF 3 11.56
C
6
H
5 -C6H 4 -4-CN 11.57
C
6
H
5 -C 6
H
4 -4-NO2 11.58
C
6
H
5 -C 6
H
4 -4-C 6
H
5 11.59
C
6
H
5
-C
6
H
4 -4-OC6Hs 11.60
C
6
H
5 -C 6
H
4 -4-C(CH 3
)
3 11.61
C
6
H
5 -C 6
H
4 -4-OCF 3 0 -65 Comp. No. R 1 R2 phys. data 11.62
C
6
H
4 -4-Cl -CF 3 11.63
C
6
H
4 -4-Cl -C 2
H
5 11.64 C 6
H
4 -4-Cl -C 3 Hrn 11.65 C 6
H
4 -4-Cl -C 3 Hri 11.66 C6H 4 -4-Cl -C 4
H
9 -t 11.67
C
6
H
4 -4-Cl -C 4
H
9 -n 11.68 C6H 4 -4-Cl -CH 2
C
6
H
5 11.69
C
8
H
4 -4-Cl -CH 2
C
6
H
4 -4-CH 3 11.70
C
6
H
4 -4-CI -C6H 4 -4-Cl 11.71 C 6
H
4 -4-CI -C 6
H
4 -4-OH 11.72 C6H 4 -4-Cl -C 6
H
4 -2-CH 3 11.73 C6H 4 -4-Cl -C6H 4 -2-Cl 11.74 C 6
H
4 -4-Cl -C6H 4 -4-Br 11.75 C 6
H
4 -4-Cl 4-pyridyl 11.76 C6H 4 -4-Cl -C 6
H
4 -4-OCH 2
-C
6
H
4 -3
CF
3 11.77
C
6
H
4 -4-Cl
C
6
H
4
-O-CH
2 F F 11.78 H -C6H5 11.79 C6H 5 -CH 2 C6H 5 11.80
C
2
H
5
-C
6
H
4 -4-Cl -66 Table 12: Compounds of the formula H 0 R F jJ H F C CHf HCH CN O CH 2 NN C N
CH
2 CH c N R FO 1- 0 Comp. No. R 1 R2 phys. data 12.01 H H 12.02 H
CH
3 12.03 H
C
2
H
5 12.04 H C 3
H
7 -n 12.05 H
C
3
H
7 -i 12.06 H C 4
H
9 -n 12.07 H C 4
H
9 -t 12.08 H C 6
H
13 -n 12.09 H C1H21-n 12.10 H
CH
2
C(CH
3
)
3 12.11 CH 3 H 12.12
CH
3 CH 3 12.13 CH 3
C
2
H
5 12.14 CH 3 C3Hrn 12.15
CH
3
C
3
H
7 -i 12.16 CH 3
C
4
H
9 -n 12.17 CH 3
C
4 Hq-t 12.18 CH 3
C
6
H
1 3 -n 12.19 CH 3 C10H21-n 12.20
CH
3
CH
2
C(CH
3
)
3 -67 Comp. No. R 1 R2 phys. data 12.21
CH
3 CeH 5 12.22 CH 3
C
8
H
4 -2-Cl 12.23 CH 3
C
6
H
4 -3-CI 12.24 CH 3
C
8
H
4 -4-Cl 12.25
CH
3
C
6
H
4 -2-CF 3 12.26
CH
3
C
6
H
4 -3-CF 3 12.27
CH
3
C
6
H
4 -4-CF 3 12.28 CH 3
C
6
H
4 -2-CN 12.29 CH 3
C
6
H
4 -3-CN 12.30 CH 3 C6H 4 -4-CN 12.31 CH 3
C
6
H
4 -2-NO2 12.32
CH
3
C
6
H
4 -3-NO2 12.33
CH
3
C
6
H
4 -4-NO2 12.34 CH 3
C
6
H
4 -4-C 6
H
5 12.35
CH
3 CeH 4 -4-OC 6
H
5 12.36
CH
3
C
6
H
4 -4-C(CH 3
)
3 12.37
CH
3
C
6
H
4 -4-OCF 3 12.38 CH 3 C6H 4 -4-COOC 2
H
5 12.39 CH 3
C
8
F
5 12.40
CH
3
C
8
H
2 -3,4,5-(OCH 3
)
3 12.41
CH
3 N 0 -68 Comp. No. R 1 R2 phys. data 12.42
CH
3 N N ~N 12.43
CH
3 \ / OH 12.44
C
6
H
5
CF
3 12.45
CH
5 C 2
H
5 12.46 C6H 5
C
3
H
7 -n 12.47 CHs C 3
H
7 -i 12.48 C 6
H
5
C
4
H
9 -t 12.49 C 6
H
5
C
4
H
9 -n 12.50 C 6
H
5 cyclopropyl 12.51 C 6
H
5 cyclopentyl 12.52 C 6
H
5 cyclohexyl 12.53
C
6
H
5 C6H 5 12.54 CHs C 6
H
4 -4-Cl 12.55 C6H 5
C
6
H
4 -4-CF 3 12.56 C 6
H
5
C
6
H
4 -4-CN 12.57 C6H 5 C 6
H
4 -4-NO2 12.58
C
6
H
5
C
6
H
4 -4-C6Hs 12.59 C 8
H
5
C
8
H
4 -4-OC 6
H
5 12.60 CHs
C
6
H
4 -4-C(CH 3
)
3 12.61
C
6
H
5 C 6
H
4 -4-OCF 3 -69 Comp. No. R 1 R2 phys. data 12.62
C
8
H
4 -4-Cl
CF
3 12.63
C
6
H
4 -4-Cl C 2
H
5 12.64
C
6
H
4 -4-Cl C 3
H
7 -n 12.65 C6H 4 -4-Cl
C
3
H
7 -i 12.66
C
6
H
4 -4-Cl C 4
H
9 -t 12.67
C
6
H
4 -4-Cl C 4
H
9 -n 12.68
C
6
H
4 -4-Cl CH 2
C
6
H
5 12.69
C
6
H
4 -4-Cl
CH
2 C6H 4 -4-CH 3 12.70 C6H 4 -4-Cl C 8
H
4 -4-Cl 12.71
C
6
H
4 -4-Cl C 6
H
4 -4-OH 12.72
C
6
H
4 -4-Cl C 6
H
4 -2-CH 3 12.73
C
6
H
4 -4-Cl C 6
H
4 -2-Cl 12.74
C
6
H
4 -4-Cl C 6
H
4 -4-Br 12.75
C
6
H
4 -4-Cl 4-pyridyl 12.76 C6H 4 -4-CI C 6
H
4 -4-OCH 2 -C6H 4 -3
CF
3 12.77 C6H 4 -4-Cl cH 4
-O-CH
2 F F 12.78 H
C
6
H
5 12.79
C
6
H
5
CH
2 C6H 5 12.80
C
2
H
5
-C
6
H
4 -4-Cl -70 Table 13: Compounds of the formula H 0 F cN- [CH 21 1c1 N I-,R C CH 2 LCH J0 C R2 Comp. No. R 1 R2 phys. data 13.01 H H 13.02 H
CH
3 13.03 H
C
2
H
5 13.04 H
C
3
H
7 -n 13.05 H
C
3 Hri 13.06 H C 4
H
9 -n 13.07 H C 4
H
9 -t 13.08 H
C
8
H
1 3 -n 13.09 H C10H21-n 13.10 H
CH
2
C(CH
3
)
3 13.11
CH
3 H 13.12
CH
3 CH 3 13.13
CH
3
C
2
H
5 13.14
CH
3
C
3
H
7 -n 13.15
CH
3 C 3
H
7 -i 13.16
CH
3
C
4
H
9 -n 13.17
CH
3
C
4 Hq-t 13.18
CH
3 C6H 1 3 -n 13.19
CH
3 Co 10
H
21 -n 41 -71 Comp. No. R 1 R2 phys. data 13.20
CH
3 CH 2
C(CH
3
)
3 13.21
CH
3 C 6
H
5 13.22
CH
3
C
6
H
4 -2-Cl 13.23
CH
3 C6H 4 -3-Cl 13.24
CH
3
C
8
H
4 -4-Cl 13.25
CH
3 C 6
H
4 -2-CF 3 13.26
CH
3
C
6
H
4 -3-CF 3 13.27
CH
3 C 6
H
4 -4-CF 3 13.28
CH
3 C 6
H
4 -2-CN 13.29
CH
3 C6H 4 -3-CN 13.30
CH
3 C6H 4 -4-CN 13.31
CH
3 C 8
H
4 -2-NO2 13.32
CH
3 C 6
H
4 -3-NO2 13.33
CH
3 C 6
H
4 -4-NO2 13.34
CH
3 CH 4 -4-C 6
H
5 13.35
CH
3 C 6
H
4 -4-OC 6
H
5 13.36
CH
3 C 6
H
4 -4-C(CH 3
)
3 13.37
CH
3 CH 4 -4-OCF 3 13.38
CH
3 CeH 4 -4-COOC 2
H
5 13.39
CH
3 C 6
F
5 13.40
CH
3 C 6
H
2 -3,4,5-(OCH 3
)
3 13.41
CH
3 N O R4) -72 Comp. No. R, R2 phys. data 13.42
CH
3 N 13.43 CH 3 \ / OH 13.44
C
6
H
5 CF 3 13.45
C
8
H
5 C 2
H
5 13.46
C
6
H
5
C
3
H
7 -n 13.47
C
6
H
5
C
3
H
7 -i 13.48 C 8
H
5
C
4 Hq-t 13.49 C6H 5
C
4 Hg-n 13.50 C6H 5 cyclopropyl 13.51
C
6
H
5 cyclopentyl 13.52 C6H 5 cyclohexyl 13.53
C
6
H
5 C 6
H
5 13.54
C
6
H
5
C
8
H
4 -4-Cl 13.55 C6H 5 C 6
H
4 -4-CF 3 13.56
C
6
H
5
C
8
H
4 -4-CN 13.57
C
6
H
5 C 8
H
4 -4-NO2 13.58
C
6
H
5 C 6
H
4 -4-C 6
H
5 13.59
C
6
H
5 C 6
H
4 -4-OC 6
H
5 13.60 C6H 5 C 6
H
4 -4-C(CH 3
)
3 13.61
C
6 Hs CeH 4 -4-OCF 3 -73 Comp. No. R 1 R2 phys. data 13.62
C
6
H
4 -4-Cl CF 3 13.63 C6H 4 -4-Cl
C
2 H 13.64
C
6
H
4 -4-Cl C 3
H
7 -n 13.65 C6H 4 -4-Cl C 3 Hy-i 13.66
C
6
H
4 -4-Cl C 4
H
9 -t 13.67
C
8
H
4 -4-Cl C 4
H
9 -n 13.68
C
6
H
4 -4-Cl CH 2
C
6 Hs 13.69
C
6
H
4 -4-Cl
CH
2 C6H 4 -4-CH 3 13.70
C
6
H
4 -4-Cl C 6
H
4 -4-Cl 13.71
C
6
H
4 -4-Cl C 6
H
4 -4-OH 13.72
C
6
H
4 -4-Cl C 6
H
4 -2-CH 3 13.73 C6H 4 -4-Cl C6H 4 -2-Cl 13.74
C
6
H
4 -4-Cl CeH 4 -4-Br 13.75
C
6
H
4 -4-Cl 4-pyridyl 13.76
C
6
H
4 -4-Cl COH 4 -4-OCH 2 -C6H 4 -3
CF
3 13.77
C
6
H
4 -4-Cl
C
6
H
4
-O-CH
2 F F 13.78 H
C
6
H
5 13.79
C
6 Hs
CH
2 C6H 5 13.80
C
2
H
5
-C
6
H
4 -4-Cl
'NT
-74 Table 14: Compounds of the formula H 0 F c C 2, 2 I 1* R C CH H CH C N C F H R Comp. No. R 1 R2 phys. data 14.01 H H 14.02 H
CH
3 14.03 H
C
2
H
5 14.04 H
C
3
H
7 -n 14.05 H
C
3
H
7 -i 14.06 H C 4
H
9 -n 14.07 H
C
4
H
9 -t 14.08 H
C
6
H
13 -n 14.09 H C1-H21-n 14.10 H
CH
2
C(CH
3
)
3 14.11
CH
3 H 14.12
CH
3 CH 3 14.13
CH
3 C 2
H
5 14.14
CH
3 C 3
H
7 -n 14.15
CH
3 C 3
H
7 -i 14.16
CH
3 C 4
H
9 -n 14.17
CH
3 C 4
H
9 -t 14.18
CH
3 C 6
H
1 3 -n 14.19
CH
3 C 1 oH 21 -n )4(1 -75 Comp. No. R, R2 phys. data 14.20
CH
3 CH 2
C(CH
3
)
3 14.21
CH
3 C 6
H
5 14.22
CH
3
C
6
H
4 -2-Cl 14.23
CH
3
C
6
H
4 -3-CI 14.24
CH
3
C
6
H
4 -4-CI 14.25
CH
3 C 6
H
4 -2-CF 3 14.26
CH
3 CrH 4 -3-CF 3 14.27
CH
3 C 6
H
4 -4-CF 3 14.28
CH
3 C6H 4 -2-CN 14.29
CH
3
C
8
H
4 -3-CN 14.30
CH
3
C
6
H
4 -4-CN 14.31
CH
3 CH 4 -2-NO2 14.32
CH
3 C 6
H
4 -3-NO2 14.33
CH
3 C 6
H
4 -4-NO2 14.34
CH
3
C
6
H
4 -4-CeH 5 14.35
CH
3
C
6
H
4 -4-OCH 5 14.36
CH
3 C 6
H
4 -4-C(CH 3
)
3 14.37
CH
3 C 6
H
4 -4-OCF 3 14.38
CH
3 C6H 4 -4-COOC 2
H
5 14.39
CH
3 C 6
F
5 14.40
CH
3 C 6
H
2 -3,4,5-(OCH 3
)
3 14.41
CH
3 N O "\6 -76 Comp. No. R 1 R2 phys. data 14.42
CH
3 - WN 14.43 CH 3 \ / OH 14.44 C6H 5
CF
3 14.45
CH
5 C 2
H
5 14.46 C 6
H
5
C
3
H
7 -n 14.47
CH
5
C
3
H
7 -i 14.48 C6H 5
C
4 Hq-t 14.49 CH 5
C
4
H
9 -n 14.50 C 6
H
5 cyclopropyl 14.51 C 6
H
5 cyclopentyl 14.52 C6H 5 cyclohexyl 14.53
C
6
H
5 C6H 5 14.54
C
6
H
5
C
8
H
4 -4-CI 14.55
C
6
H
5 C 6
H
4 -4-CF 3 14.56
C
6
H
5 C6H 4 -4-CN 14.57 CHs
C
6
H
4 -4-NO2 14.58
C
6
H
5 C6H 4 -4-C 6
H
5 14.59
C
6
H
5 C 6
H
4 -4-OC 6
H
5 14.60
CH
5 C 6
H
4 -4-C(CH 3
)
3 14.61
C
8
H
5 C 6
H
4 -4-OCF 3 -77 Comp. No. R 1 R2 phys. data 14.62 C 6
H
4 -4-CI CF 3 14.63
C
8
H
4 -4-Cl C 2
H
5 14.64
C
6
H
4 -4-Cl C 3
H
7 -n 14.65
C
8
H
4 -4-Cl C 3 H-i 14.66
C
6
H
4 -4-Cl C 4
H
9 -t 14.67
C
8
H
4 -4-Cl C 4
H
9 -n 14.68
C
6
H
4 -4-Cl
CH
2 C6H 5 14.69
C
6
H
4 -4-Cl CH 2
C
6
H
4 -4-CH 3 14.70
C
6
H
4 -4-Cl C 6
H
4 -4-CI 14.71 C 6
H
4 -4-Cl C 8
H
4 -4-OH 14.72
C
8
H
4 -4-Cl C6H 4 -2-CH 3 14.73
C
6
H
4 -4-Cl C 6
H
4 -2-Cl 14.74
C
6
H
4 -4-Cl C 6
H
4 -4-Br 14.75
C
6
H
4 -4-Cl 4-pyridyl 14.76
C
6
H
4 -4-Cl C 6
H
4 -4-OCH 2
-C
6
H
4 -3
CF
3 14.77 C6H 4 -4-Cl
C
8
H
4
-O-CH
2 F F 14.78 H
C
6
H
5 14.79
C
6
H
5 CH 2
CH
5 14.80
C
2
H
5
-C
8
H
4 -4-Cl -78 Table 15: Compounds of the formula H 0 R F II H F
~CH
2 ]..C2 'l N c C CH _ HCH 2 C 0 C N
R
2 Comp. No. R, R2 phys. data 15.01 H H 15.02 H
CH
3 15.03 H
C
2
H
5 15.04 H
C
3 H-n 15.05 H
C
3
H
7 -i 15.06 H C 4
H
9 -n 15.07 H C 4
H
9 -t 15.08 H
C
6
H
13 -n 15.09 H C10H2rn 15.10 H
CH
2
C(CH
3
)
3 15.11
CH
3 H 15.12
CH
3 CH 3 15.13
CH
3
C
2
H
5 15.14
CH
3
C
3
H
7 -n 15.15
CH
3 C 3
H
7 -i 15.16
CH
3
C
4
H
9 -n 15.17
CH
3
C
4
H
9 -t 15.18
CH
3 C 6
H
13 -n 15.19
CH
3
C
10
H
21 -n 15.20
CH
3 CH 2
C(CH
3
)
3 1V -79 Comp. No. R 1
R
2 phys. data 15.21
CH
3
C
6 Hs 15.22
CH
3
C
6
H
4 -2-Cl 15.23
CH
3
C
6
H
4 -3-CI 15.24
CH
3
C
6
H
4 -4-Cl 15.25
CH
3 C 6
H
4 -2-CF 3 15.26
CH
3 C 6
H
4 -3-CF 3 15.27
CH
3 C 8
H
4 -4-CF 3 15.28
CH
3
C
6
H
4 -2-CN 15.29
CH
3
C
6
H
4 -3-CN 15.30
CH
3 C6H 4 -4-CN 15.31
CH
3 C6H 4 -2-NO2 15.32
CH
3 C6H 4 -3-NO2 15.33
CH
3 C 6
H
4 -4-NO2 15.34
CH
3
C
6
H
4 -4-C 6
H
5 15.35
CH
3
C
6
H
4 -4-OCHs 15.36
CH
3 C6H 4 -4-C(CH 3
)
3 15.37
CH
3 CH 4 -4-OCF 3 15.38
CH
3 C 6
H
4 -4-COOC 2
H
5 15.39
CH
3 C 6
F
5 15.40
CH
3 CeH 2 -3,4,5-(OCH 3
)
3 15.41
CH
3 N O 4' - 80 Comp. No. R 1 R2 phys. data 15.42 CH 3 15.43 CH 3 \ / OH 15.44 CH 5
CF
3 15.45 C 6
H
5
C
2 H 15.46 CH 5
C
3 H-n 15.47 CH 5
C
3
H
7 -i 15.48
CH
5
C
4
H
9 -t 15.49 CH 5
C
4
H
9 -n 15.50 CH 5 cyclopropyl 15.51 CH 5 cyclopentyl 15.52 CH 5 cyclohexyl 15.53 CH 5
CH
5 15.54 CH 5
C
6
H
4 -4-CI 15.55 CH 5
C
6
H
4 -4-CF 3 15.56 CrH 5
C
6
H
4 -4-CN 15.57 C 6
H
5 C6H 4 -4-NO2 15.58 CH 5
C
6
H
4 -4-C 6
H
5 15.59 CH 5
C
6
H
4 -4-OC 6
H
5 15.60 CH 5 C6H 4 -4-C(CH 3
)
3 15.61 CH 5
C
6
H
4 -4-OCF 3 4J) -81 Comp. No. R 1
R
2 phys. data 15.62 C 6
H
4 -4-CI CF 3 15.63 C 6
H
4 -4-Cl C 2
H
5 15.64 C 6
H
4 -4-Cl C 3 Hrn 15.65 C 6
H
4 -4-Cl C 3 Hri 15.66 C 6
H
4 -4-Cl C 4
H
9 -t 15.67 C 6
H
4 -4-Cl C 4
H
9 -n 15.68 C 6
H
4 -4-Cl CH 2 C6H 5 15.69 C 6
H
4 -4-CI CH 2
C
6
H
4 -4-CH 3 15.70 C 6
H
4 -4-Cl C6H 4 -4-CI 15.71 C 6
H
4 -4-Cl C6H 4 -4-OH 15.72 C 6
H
4 -4-CI C 6
H
4 -2-CH 3 15.73 C 6
H
4 -4-Cl C 6
H
4 -2-CI 15.74 C6H 4 -4-Cl C6H 4 -4-Br 15.75 C 6
H
4 -4-Cl 4-pyridyl 15.76 C 6
H
4 -4-Cl C 6
H
4 -4-OCH 2 -C6H 4 -3
CF
3 15.77
C
6
H
4 -4-Cl C 6
H
4 -0-CH 2 F F 15.78 H -C6H5 15.79 C 6 Hs CH 2
C
6 Hs 15.80 C 2 H -C 6
H
4 4-CI -82 Table 16: Compounds of the formula H 0 F c NI H 2 c N RI C CHL H CHJ 5 O Comp. No. R 1
R
2 phys. data 16.01 H H 16.02 H
CH
3 16.03 H
C
2
H
5 16.04 H C 3
H
7 -n 16.05 H C3Hz-i 16.06 H C 4
H
9 -n 16.07 H C 4
H
9 -t 16.08 H C 8
H
1 3 -n 16.09 H C 10
H
21 -n 16.10 H
CH
2
C(CH
3
)
3 16.11
CH
3 H 16.12
CH
3 CH 3 16.13
CH
3 C 2
H
5 16.14 CH 3
C
3
H
7 -n 16.15
CH
3 C 3
H
7 -i 16.16 CH 3
C
4
H
9 -n 16.17
CH
3
C
4
H
9 -t 16.18
CH
3
C
6
H
1 3 -n 16.19
CH
3
C
10
H
21 -n -83 Comp. No. R 1
R
2 phys. data 16.20 CH 3
CH
2
C(CH
3
)
3 16.21 CH 3
C
6
H
5 16.22 CH 3
C
6
H
4 -2-CI 16.23 CH 3 C6H 4 -3-Cl 16.24 CH 3
C
6
H
4 -4-Cl 16.25 CH 3
C
6
H
4 -2-CF 3 16.26 CH 3
C
8
H
4 -3-CF 3 16.27 CH 3
C
6
H
4 -4-CF 3 16.28 CH 3 C6H 4 -2-CN 16.29 CH 3 CrH 4 -3-CN 16.30 CH 3
C
6
H
4 -4-CN 16.31 CH 3 C6H 4 -2-NO2 16.32 CH 3
C
6
H
4 -3-NO2 16.33 CH 3 CrH 4 -4-NO2 16.34 CH 3
C
6
H
4 -4-C 6
H
5 16.35 CH 3
C
6
H
4 -4-OC6H 5 16.36 CH 3
C
6
H
4 -4-C(CH 3
)
3 16.37 CH 3
C
6
H
4 -4-OCF 3 16.38 CH 3
C
6
H
4 -4-COOC 2
H
5 16.39 CH 3
C
6
F
5 16.40 CH 3
C
6
H
2 -3,4,5-(OCH 3
)
3 16.41 CH 3 N 0
?VT
-84 Comp. No.
R
1 R2 phys. data 16.42
CH
3 N \ N 16.43
CH
3 OH 16.44
C
6
H
5 CF 3 16.45
C
6
H
5 C 2
H
5 16.46
C
6
H
5 C 3
H
7 -n 16.47
C
6
H
5 C 3
H
7 -i 16.48
C
6
H
5 C 4 Hq-t 16.49 C6H 5 C 4
H
9 -n 16.50
C
6
H
5 cyclopropyl 16.51 C6H 5 cyclopentyl 16.52 C6H 5 cyclohexyl 16.53 C6H 5 C6H 5 16.54
C
6
H
5 C6H 4 -4-Cl 16.55
C
6
H
5 C 8
H
4 -4-CF 3 16.56
C
6
H
5 CrH 4 -4-CN 16.57
C
6
H
5 C6H 4 -4-NO2 16.58
C
6
H
5 C6H 4 -4-C6H 5 16.59
C
6
H
5 C6H 4 -4-OC 6
H
5 16.60
C
6
H
5 C6H 4 -4-C(CH 3
)
3 16.61 C6H 5 C 6
H
4 -4-OCF 3 -85 Comp. No. R 1 R2 phys. data 16.62
C
6
H
4 -4-CI CF 3 16.63 C 6
H
4 -4-CI C 2
H
5 16.64 C6H 4 -4-Cl C 3
H
7 -n 16.65 C6H 4 -4-Cl C 3
H
7 -i 16.66 CsH 4 -4-CI C 4
H
9 -t 16.67 C 6
H
4 -4-Cl C 4 Hg-n 16.68 C6H 4 -4-Cl CH 2
C
6 Hs 16.69 C 6
H
4 -4-Cl CH 2
C
6
H
4 -4-CH 3 16.70 C6H 4 -4-Cl C 6
H
4 -4-Cl 16.71 C 6
H
4 -4-CI C6H 4 -4-OH 16.72 C 6
H
4 -4-Cl C 6
H
4 -2-CH 3 16.73 C 6
H
4 -4-CI C 6
H
4 -2-CI 16.74 C 6
H
4 -4-Cl C 6
H
4 -4-Br 16.75 C 6
H
4 -4-Cl 4-pyridyl 16.76 C6H 4 -4-Cl C 6
H
4 -4-OCH 2
-C
6
H
4 -3
CF
3 16.77 C6H 4 -4-Cl C 6
H
4
-O-CH
2 F F 16.78 H C 6
H
5 16.79
C
6
H
5
CH
2
C
6
H
5 16.80 C 2
H
5 -C6H 4 -4-Cl RA4, -86 Table 17: Compounds of the formula H O F C CH 2 HCH5 N R N 1 H Comp. No. R 1 R2 phys. data 17.01 H H 17.02 H CH 3 17.03 H C 2
H
5 17.04 H C 3
H
7 -n 17.05 H C 3
H
7 -i 17.06 H C 4
H
9 -n 17.07 H C 4
H
9 -t 17.08 H C 6
H
13 -n 17.09 H C 1
H
21 -n 17.10 H CH 2
C(CH
3
)
3 17.11 CH 3 H 17.12 CH 3
CH
3 17.13 CH 3
C
2 H 17.14 CH 3
C
3
H
7 -n 17.15 CH 3
C
3
H
7 -i 17.16 CH 3
C
4 Hf-n 17.17 CH 3
C
4 Hq-t 17.18 CH 3 CrH 1 3 -n 17.19 CH 3 C10H21-n RA 9 j -87 Comp. No. R 1 R2 phys. data 17.20 CH 3
CH
2
C(CH
3
)
3 17.21 CH 3
C
6
H
5 17.22 CH 3 C6H 4 -2-CI 17.23 CH 3
C
6
H
4 -3-Cl 17.24 CH 3
C
6
H
4 -4-Cl 17.25 CH 3
C
6
H
4 -2-CF 3 17.26 CH 3
C
6
H
4 -3-CF 3 17.27 CH 3
C
6
H
4 -4-CF 3 17.28 CH 3
C
6
H
4 -2-CN 17.29 CH 3 C6H 4 -3-CN 17.30 CH 3 C6H 4 -4-CN 17.31 CH 3
C
6
H
4 -2-NO2 17.32 CH 3 C6H 4 -3-NO2 17.33 CH 3 C6H 4 -4-NO2 17.34 CH 3 C6H 4 -4-C 6
H
5 17.35 CH 3 C6H 4 -4-OC 6
H
5 17.36 CH 3
C
6
H
4 -4-C(CH 3
)
3 17.37 CH 3
C
6
H
4 -4-OCF 3 17.38 CH 3
C
6
H
4 -4-COOC 2
H
5 17.39 CH 3 C6F 5 17.40 CH 3
-C
6
H
2 -3,4,5-(OCH 3
)
3 17.41 CH 3 N 0
C)~
- 88 Comp. No. R 1 R2 phys. data 17.42
CH
3 N 17.43 CH 3 \ / OH 17.44 CHs
CF
3 17.45
CH
5 C 2 Hs 17.46 C6H 5 C 3
H
7 -n 17.47
C
6
H
5 C 3
H
7 -i 17.48 CHs
C
4
H
9 -t 17.49
C
8
H
5 C 4
H
9 -n 17.50 CHs cyclopropyl 17.51
CH
5 cyclopentyl 17.52
CH
5 cyclohexyl 17.53
C
6
H
5 CH 5 17.54
CH
5 C 6
H
4 -4-Cl 17.55
CH
5 C 6
H
4 -4-CF 3 17.56 CHs
C
6
H
4 -4-CN 17.57 CHs
C
6
H
4 -4-NO2 17.58 CHs C6H 4 -4-C6H 5 17.59 CHs C6H 4 -4-OC6H 5 17.60
C
6
H
5 C6H 4 -4-C(CH 3
)
3 17.61 CHs C6H 4 -4-OCF 3
RA/
-89 Comp. No. R, R2phys. data 17.62
C
6
H
4 -4-CI CF 3 17.63 C6H 4 -4-CI C 2
H
5 17.64 C 6
H
4 -4-CI C 3 Hr-n 17.65 C6H 4 -4-CI C 3 H-i 17.66 C 6
H
4 -4-CI C 4
H
9 -t 17.67 C 6
H
4 -4-CI C 4
H
9 -n 17.68 C 6
H
4 -4-CI CH 2
C
6
H
5 17.69
C
6
H
4 -4-CI CH 2
C
6
H
4 -4-CH 3 17.70
C
6
H
4 -4-CI C 6
H
4 -4-CI 17.71 C 6
H
4 -4-CI C6H 4 -4-OH 17.72 C6H 4 -4-CI C 6
H
4 -2-CH 3 17.73 C6H 4 -4-CI C 6
H
4 -2-CI 17.74 C 6
H
4 -4-CI C 6
H
4 -4-Br 17.75 C 6
H
4 -4-Cl 4-pyridyl 17.76
C
6
H
4 -4-CI C 6
H
4 -4-OCH 2
-C
6
H
4 -3-CF 3 17.77 C6H 4 -4-CI CH- -CH 2 q F F 17.78 H
C
8
H
5 17.79 C6H 5
CH
2 C6H 5 17.80 CAH
-C
8
H
4 -4-CI
C-)
- 90 Table 18: Compounds of the formula H 0 H R, F C CH 2 CC OCH 0 NNC Comp. No. R 1 R2 phys. data 18.01 H H 18.02 H CH 3 18.03 H C 2 H 18.04 H C 3
H
7 -n 18.05 H C 3
H
7 -i 18.06 H C 4
H
9 -n 18.07 H C 4
H
9 -t 18.08 H C 8
H
13 -n 18.09 H CoH21-n 18.10 H CH 2
C(CH
3
)
3 18.11 CH 3 H 18.12 CH 3
CH
3 18.13 CH 3
C
2 H 18.14 CH 3
C
3
H
7 -n 18.15 CH 3
C
3
H
7 -i 18.16 CH 3
C
4
H
9 -n 18.17 CH 3
C
4 H9-t 18.18 CH 3 CrH 13 -n 18.19 CH 3
C
10
H
21 -n ':I ,< 7)) - 91 Comp. No. R 1 R2 phys. data 18.20 CH 3
CH
2
C(CH
3
)
3 18.21 CH 3
C
6 Hs 18.22 CH 3
C
6
H
4 -2-Cl 18.23 CH 3
C
6
H
4 -3-Cl 18.24 CH 3
C
6
H
4 -4-Cl 18.25 CH 3
C
6
H
4 -2-CF 3 18.26 CH 3
C
6
H
4 -3-CF 3 18.27 CH 3
C
6
H
4 -4-CF 3 18.28
CH
3
C
6
H
4 -2-CN 18.29
CH
3 C6H 4 -3-CN 18.30
CH
3
C
6
H
4 -4-CN 18.31 CH 3
C
6
H
4 -2-NO2 18.32 CH 3 C6H 4 -3-NO2 18.33 CH 3
C
6
H
4 -4-NO2 18.34 CH 3
C
8
H
4 -4-C6H 5 18.35 CH 3 C6H 4 -4-OC 6
H
5 18.36 CH 3 CrH 4 -4-C(CH 3
)
3 18.37 CH 3 C6H 4 -4-OCF 3 18.38 CH 3
C
6
H
4 -4-COOC 2
H
5 18.39 CH 3
C
8
F
5 18.40 CH 3
C
6
H
2 -3,4,5-(OCH 3
)
3 18.41 CH 3 N 0 \ ../ -92 Comp. No. R 1 R2 phys. data 18.42 CH 3 N-N 18.43 CH 3 \ / OH 18.44 C6H 5
CF
3 18.45 C 6
H
5
C
2
H
5 18.46 C 6
H
5
C
3
H
7 -n 18.47 C6H 5
C
3
H
7 -i 18.48 C 6
H
5
C
4 Hg-t 18.49 C 6
H
5
C
4
H
9 -n 18.50 C 8
H
5 cyclopropyl 18.51 C 6
H
5 cyclopentyl 18.52 C 6
H
5 cyclohexyl 18.53 C6H 5
C
6
H
5 18.54 C 6
H
5
C
6
H
4 -4-Cl 18.55 C 6
H
5 C6H 4 -4-CF 3 18.56 C6H 5
C
6
H
4 -4-CN 18.57 C 6
H
5 C6H 4 -4-NO2 18.58 CH 5 C6H 4 -4-C 6
H
5 18.59 CH 5
C
6
H
4 -4-OC 6
H
5 18.60 C 6
H
5
C
6
H
4 -4-C(CH 3
)
3 44.
- 93 Comp. No. R 1 R2 phys. data 18.61
C
6
H
5
C
6
H
4 -4-OCF 3 18.62
C
6
H
4 -4-Cl CF 3 18.63 C6H 4 -4-Cl C 2
H
5 18.64
C
8
H
4 -4-Cl C 3
H
7 -n 18.65 C6H 4 -4-C C 3
H
7 -i 18.66 C 6
H
4 -4-Cl C 4 Hq-t 18.67 C6H 4 -4-Cl C 4
H
9 -n 18.68
C
8
H
4 -4-Cl CH 2
C
6
H
5 18.69
C
8
H
4 -4-CI CH 2 C6H 4 -4-CH 3 18.70 C 6
H
4 -4-CI C 6
H
4 -4-Cl 18.71 C 6
H
4 -4-Cl C 6
H
4 -4-OH 18.72
C
6
H
4 -4-CI C 8
H
4 -2-CH 3 18.73 C6H 4 -4-Cl C6H 4 -2-CI 18.74 C6H 4 -4-Cl C 6
H
4 -4-Br 18.75 C 6
H
4 -4-CI 4-pyridyl 18.76 C6H 4 -4-CI C 6
H
4 -4-OCH 2 -C6H 4 -3
CF
3 18.77
C
6
H
4 -4-CI
C
8
H
4
-O-CH
2 F F 18.78 H
C
6
H
5 18.79
CH
5 CH 2
C
8
H
5 18.80
C
2
H
5 -C6H 4 -4-CI -94 Table 19: Compounds of the formula F 0 H2{ H,'L 5 F R2 Comp. No. R, R2 X n phys. data 19.1 -C 6
H
5 -C6H 5 NH 0 19.2 -C 6
H
5
-C
6
H
5 NH I m.p.: 92-93 0 C 19.3 -C 6
H
5 -C6H 5 NH 2 19.4 -C 6
H
5
-C
6
H
5 NH 3 19.5 -C 6
H
5
-C
6
H
5 NH 4 19.6 -C6H 5
-C
6
H
5 NH 5 19.7 -C 6
H
5 -C6H 5 0 0 19.8 -C 6
H
5
-C
6
H
5 0 1 amorphous 19.9 -C 6
H
5
-C
6
H
5 0 2 19.10 -C 6
H
5
-C
6
H
5 0 3 19.11 -C6H 5
-C
6
H
5 0 4 19.12 -C 6
H
5
-C
6
H
4 -4-Cl 0 5 19.13 CH 3
-C
6
H
4 -4-Cl NH 0 19.14 CH 3
-C
8
H
4 -4-CI NH 1 19.15 CH 3
-C
6
H
4 -4-Cl NH 2 19.16 CH 3
-CH
4 -4-Cl NH 3 19.17 CH 3
-C
6
H
4 -4-Cl NH 4 19.18 CH 3
-C
6
H
4 -4-CI NH 5 19.19 CH 3
-CH
4 -4-Cl 0 0 - 95 Comp. No. R 1 R2 X n phys. data 19.20 CH 3
-C
6
H
4 -4-Cl 0 1 19.21 CH 3
-C
6
H
4 -4-Cl 0 2 19.22 CH 3
-C
6
H
4 -4-Cl 0 3 19.23 CH 3 -C6H 4 -4-Cl 0 4 19.24 CH 3
-C
6
H
4 -4-CI 0 5 19.25 -C 6
H
4 -4-Cl -CH 4 -4-CI NH 1 19.26 -C 6
H
4 -4-Cl -C 6
H
4 -4-CI 0 1 Table 20: Compounds of the formula
CH
3 0 2 F NR1 F R2 Comp. No. R 1 R2 X n phys. data 20.1 -C 6
H
5
-C
6
H
5 NH 0 20.2 -C 6
H
5
-C
6
H
5 NH 1 m.p.: 89-100C 20.3 -C 6
H
5 -C6H 5 NH 2 20.4 -C 6
H
5
-C
6
H
5 NH 3 20.5 -C 6
H
5
-C
6
H
5 NH 4 20.6 -CeH 5
-C
6
H
5 NH 5 20.7 -C6H 5
-CH
5 0 0 20.8 -C 6
H
5
-C
6
H
5 0 1 nD20 = 1.5530 20.9 -C 6
H
5
-C
6
H
5 0 2 20.10 -C 6
H
5 -C6H 5 0 3 -96 Comp. No. R 1 R 2 X n phys. data 20.11
-C
6
H
5 -C 8
H
5 0 4 20.12
-C
8
H
5 -C 6
H
4 -4-CI 0 5 20.13
CH
3 -C 8
H
4 -4-Cl NH 0 20.14
CH
3 -C 6
H
4 -4-CI NH 1 20.15
CH
3 -CrH 4 -4-Cl NH 2 20.16
CH
3 -C6H 4 -4-CI NH 3 20.17
CH
3 -C 6
H
4 -4-CI NH 4 20.18
CH
3 -C 6
H
4 -4-CI NH 5 20.19
CH
3 -C6H 4 -4-Cl 0 0 20.20
CH
3 -C 6
H
4 -4-Cl 0 1 20.21
CH
3 -C 6
H
4 -4-CI 0 2 20.22
CH
3 -C 6
H
4 -4-Cl 0 3 20.23
CH
3 -C 6
H
4 -4-Cl 0 4 20.24
CH
3 -C 6
H
4 -4-CI 0 5 20.25
-C
6
H
4 -4-CI
-C
8
H
4 -4-Cl NH 1 20.26
-C
8
H
4 -4-Cl
-C
6
H
4 -4-Cl 0 1 Biological Examples Example B1: Ovicidal action on Heliothis virescens Heliothis virescens eggs which have been deposited on filter paper are briefly immersed into an acetonic/aqueous test solution comprising 400 ppm of the active compound to be tested. After the test solution has dried on, the eggs are incubated in Petri dishes. After 6 days, the percentage hatching rate of the eggs is evaluated in comparison with untreated control batches (% reduction in hatching). In this test, compounds according to Tables 1 - 20 are very effective against Heliothis virescens. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4,79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, -97 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.79, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of over 80%. Example B2: Action against Nilaparvata lugens Rice plants are treated with an aqueous emulsion spray liquor comprising 400 ppm of the active compound. After the spray coating has dried on, the rice plants are populated with 2nd and 3rd instar larvae of Nilaparvata lugens. 21 days later, the test is evaluated. The percentage reduction in population (% activity) is determined by comparing the number of surviving leaf hoppers on the treated plants with that on the untreated plants. In this test, the compounds of Tables 1 - 20 are very effective against Nilaparvata lugens. The compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4,79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.79, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of over 80%. Example B3: Activity against Diabrotica balteata larvae Maize seedlings are sprayed with an aqueous emulsion spray liquor which comprises 400 ppm of the active compound. After the spray coating has dried on, the maize seedlings are populated with 10 second instar larvae of Diabrotica balteata and introduced into a plastic container. 6 days later, the test is evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead larvae on the treated plants with that on the untreated plants. In this test, the compounds of Tables 1 - 20 are very effective against Diabrotica balteata. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4,79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 6.53, 6.21, 6.78, 6.79, 6.12, 6.02, 6.26 and 6.80, in particular, exhibit an activity of over 80%. Example B4: Activity against Tetranychus urticae Young bean plants are populated with a mixed population of Tetranychus urticae and, 1 day later, sprayed with an aqueous emulsion spray liquor which comprises 400 ppm of the active compound. The plants are subsequently incubated for 6 days at 25 0 C and then evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead eggs, larvae and adults on the treated plants with that on the untreated plants. In this test, the compounds of Tables 1 - 20 are very effective against Tetranychus urticae. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4,79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, I-i C-)
TL
-98 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of over 80%. Example B5: Activity against Spodoptera littoralis caterpillars Young soya plants are sprayed with an aqueous emulsion spray liquor which comprises 400 ppm of the active compound. After the spray coating has dried on, the soya plants are populated with 10 third instar caterpillars of Spodoptera littoralis and introduced into a plastic container. Three days later, the test is evaluated. The percentage reduction in population and the percentage reduction in feeding damage (% activity) is determined by comparing the number of dead caterpillars and the feeding damage, respectively, on the treated plants with those on the untreated plants. In this test, the compounds of Tables 1- 20 are very effective against Spodoptera littoralis. Compounds 4.80, 4.53, 4.12, 4.21, 4.36, 5.77, 5.53, 5.21, 5.78, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of over'80%. Example B6: Activity against Plutella xylostella caterpillars Young cabbage plants are sprayed with an aqueous emulsion spray liquor which comprises 400 ppm of the active compound. After the spray coating has dried on, the cabbage plants are populated with 10 third instar caterpillars of Plutella xylostella and introduced into a plastic container. 3 days later, the test is evaluated. The percentage reduction in population and the percentage reduction in feeding damage (% activity) is determined by comparing the number of dead caterpillars and the feeding damage, respectively, on the treated plants with those on the untreated plants. In this test, the compounds of Tables 1 - 20 are very effective against Plutella xylostella. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4,79, 4.02, 4.36, 4.26, 5.77, 5.53, 5.78, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02 and 6.80, in particular, exhibit an activity of over 80%. Example B7: Activity aainst Aphis craccivora Pea seedlings are infected with Aphis craccivora and subsequently sprayed with a spray liquor which comprises 400 ppm of the active ingredient and incubated at 20*C. 3 and 6 days later, respectively, the test is evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead leaf spars on the treated plants with that on the untreated plants. 21~, - 99 In this test, the compounds of Tables 1 - 20 are very effective against Aphis craccivora. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4,79, 4.36, 4.26, 5.77, 5.53, 5.21, 5.78, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02 and 6.80, in particular, exhibit an activity of over 80%. Example B8: Activity against Myzus Dersicae Pea seedlings are infected with Myzus persicae and subsequently sprayed with a spray liquor which comprises 400 ppm of the active compound and incubated at 20*C. 3 and 6 days later, respectively, the test is evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead aphids on the treated plants with that on the untreated plants. In this test, the compounds of Tables 1 - 20 are very effective against Myzus persicae. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4,79, 4.36, 4.26, 5.21, 5.78, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02 and 6.80, in particular, exhibit an activity of over 80%. Example 9: Systemic action against Myzus persicae Pea seedlings are infected with Myzus persicae, the roots are then placed in a spray liquor which comprises 400 ppm of the active compound, and the seedlings are incubated at 20*C. 3 and 6 days later, respectively, the test is evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead aphids on the treated plants with that on the untreated plants. In this test, the compounds of Tables 1 - 20 are very effective against Myzus persicae. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4,79, 4.02, 4.36, 5.21, 5.78, 5.02, 5.12, 6.21, 6.78, 6.79 and 6.80, in particular, exhibit an activity of over 80%. Example B10: _Ovo/larvicidal action on Heliothis virescens Heliothis virescens eggs which have been deposited on cotton are sprayed with an aqueous emulsion spray liquor which comprises 400 ppm of the active compound. After 8 days, the percentage hatching rate of the eggs and the survival rate of the caterpillars is evaluated in comparison with untreated control batches (% reduction in population). In this test, compounds of Tables 1 - 20 are very effective against Heliothis virescens. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4,79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.79, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of over 80%.
-100 Example B11: Ovicidal activity against Tetranychus urticae Young bean plants are populated with female Tetranychus urticae which are removed again after 24 hours. The plants which are populated with eggs are sprayed with an aqueous emulsion spray liquor which comprises 400 ppm of the active compound. The plants are subsequently incubated at 25 0 C for 6 days and then evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead eggs, larvae and adults on the treated plants with that on the untreated plants. In this test, the compounds of Tables 1 - 20 are very effective against Tetranychus urticae. Compounds 4.53, 4.78, 4.12, 4.21, 4,79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of over 80%. Example B12: Activity against Panonychus ulmi (OP and Carb. resistent) Apple seedlings are populated with adult females of Panonychus ulmi. After seven days, the infected plants are sprayed to run off point with an aqueous emulsion spray liquor comprising 400 ppm of the compound to be tested, and cultivated in a greenhouse. After 14 days, the test is evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead spider mites on the treated plants with that on the untreated plants. In the above test, the compounds of Tables 1 - 20 are very effective. Compounds 4.53, 4.78, 4.12, 4.21, 4,79, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of over 80%.

Claims (19)

1. A compound of the formula R R C CH 2 C C O C N R 2 F - - m-- - n in which R 1 and R 2 independently of one another are hydrogen; or alkyl, a group N , aryl, cycloalkyl, alkenyl or alkynyl, which are substituted or unsubstituted; R 3 is hydrogen, fluorine or methyl; m is 0, 1, 2, 3, 4 or 5; n is 0 or 1; X is oxygen or NR 4 ; and R 4 is hydrogen or C 1 -C6-alkyl or benzyl, which are substituted or unsubstituted, and, if appropriate, its possible E/Z isomers, E/Z isomer mixtures and/or tautomers, in each case in free form or in salt form, with the proviso that a) R 3 is not hydrogen or fluorine and m and n are not both 0 if X is oxygen and R 1 and R 2 independently of one another are hydrogen or unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aryl or heteroaryl; b) R 3 is not hydrogen or fluorine and m and n are not both 0 if R 4 is hydrogen and R 1 and R 2 independently of one another are hydrogen or unsubstituted or substituted alkyl, aryl or heteroaryl; c) m is not 0, 1 or 2 and R4 is hydrogen, alkyl or haloalkyl if one of the radicals R 1 or R 2 is 4-alkylsulphonyloxyphenyl, 4 haloalkylsulphonyloxyphenyl or 4-haloalkoxysulphonyloxyphenyl which may or may not carry further substituents, and the other radical is substituted or unsubstituted phenyl; and d) m is not 0, 1 or 2 and R 4 is not hydrogen, alkyl or haloalkyl and n is not 0 if one of the radicals R 1 und R 2 is 4-perhaloalkoxyphenyl which may or may not carry further substituents and the other is substituted or unsubstituted phenyl. -102
2. A compound of the formula (I) according to Claim 1 in free form.
3. A compound of the formula (1) according to Claim 1 in which R 1 and R 2 independently of one another are hydrogen; C 1 -C 20 -alkyl, which may be straight chain or branched and and may be mono- to tetrasubstituted by hydroxyl, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morpholino, alkoxycarbonyl, alkylcarbonyloxy, cycloalkyl, phenyl, naphthyl, phenoxy, naphthoxy, phenylthio, naphthylthio, phenylsulphonyl, naphthylsulphonyl, phenylsulphonyloxy, naphthylsulphonyloxy, benzoyl, naphthoyl, heteroaryl or heteroaryloxy having 5 to 6 ring members and 1 to 2 hetero atoms N, 0 or S, where the aryl or heteroaryl groups mentioned for their part may be mono- or disubstituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro, cyano, phenoxy, halophenoxy, phenylthio or halophenylthio; C 3 -C 20 -alkenyl, which may be straight-chain or branched and may be mono- to tetrasubstituted by halogen; C 3 -C 20 -alkynyl, which may be straight-chain or branched and may be mono- to tetrasubstituted by halogen; C 3 -C 7 -cycloalkyl, which may be mono- or tetra-substituted by halogen, alkyl or haloalkyl; Phenyl or naphthyl, which may be mono- to tetra-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkylthio, haloalkylthio, alkylsulphonyloxy, haloalkylsulphonyloxy, haloalkoxysulphonyloxy, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkylsilyl, phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl or heteroaryloxy having 5 to 6 ring members and 1 to 2 heteroatoms N, 0 or S, where phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl and heteroaryloxyradicals as substituents may for their part be mono- or disubstituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro, cyano, phenoxy, phenylthio, halophenylthio, cycloalkylalkoxy or halocycloalkylalkoxy; heteroaryl having 5 to 6 ring members and 1 to 2 heteroatoms N, 0 or S, which may be mono- to tetra-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkylsilyl, phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl or heteroaryloxy having 5 to 6 ring members and 1 to 2 -103 heteroatoms N, 0 or S, where phenyl, phenoxy, phenylthio, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl and heteroaryloxy radicals as substituents for their part may be mono or disubstituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro, cyano, phenoxy, phenylthio, halophenylthio, cycloalkylalkoxy, halocycloalkylalkoxy; R 3 is hydrogen, fluorine or methyl; m is 0, 1, 2, 3, 4 or 5; n is 0 or 1; and X is oxygen or NR 4 , where R 4 is hydrogen, C-C 4 -alkyl which may be mono- or polysubstituted by halogen, C-C 4 alkoxy or di-C-C 4 -alkylamino, or is benzyl which may be mono- or polysubstituted by halogen, C-C 4 -alkyl, halo-Cl-C 4 -alkyl, C-C 4 -alkoxy, nitro or cyano.
4. A compound of the formula (1) according to any one of Claims 1 or 2 in which R 1 and R 2 independently of one another are hydrogen or unsubstituted or substituted alkyl, cycloalkyl, alkenyl or alkynyl, R 3 is hydrogen, fluorine or methyl, m is 0, 1, 2, 3, 4 or 5; n is 0 or 1, X is oxygen or NR 4 , and R 4 is hydrogen or unsubstituted or substituted C-C 6 -alkyl or benzyl.
5. A compound of the formula (1), according to Claim 1 or 2 in which R 1 is hydrogen or unsubstituted or substituted alkyl, alkenyl, alkynyl or cycloalkyl, R 2 is hydrogen or unsubstituted or substituted aryl or heteroaryl, R 3 is hydrogen, fluorine or methyl, m is 0, 1, 2, 3, 4 or 5 and n is 0 or 1, -104 X is oxygen or NR 4 , and R 4 is hydrogen or unsubstituted or substituted C 1 -C6-alkyl or benzyl.
6. A compound of the formula (1) according to Claim 1 or 2 in which R 1 and R 2 independently of one another are hydrogen or unsubstituted or substituted aryl, R 3 is hydrogen, fluorine or methyl, m is 0, 1, 2, 3, 4 or 5 and n is 0 or 1, X is oxygen or NR 4 , and R 4 is hydrogen or unsubstituted or substituted C-C-alkyl or benzyl.
7. A compound of the formula (1) according to any one of Claims 1-5 in which R 3 is hydrogen and R 1 , R 2 , R 4 , m, n and X are as defined.
8. A compound of the formula (I) according to any one of Claims 1-5 in which m is 0, 1, 2, 3 or 4 and R 1 , R 2 , R 3 , R 4 , n and X are as defined.
9. A compound of the formula (1) according to any one of Claims 1-5 in which m is 1 or 4 and R 1 , R 2 , R 3 , R 4 , n and X are as defined.
10. A compound of the formula (1) according to any one of Claims 1-5 in which n is 0 and R 1 , R 2 , R 3 , R 4 , m and X are as defined.
11. A compound of the formula (I) according to any one of Claims 1-5 in which n is 0 and m is 1 or 4 and R 1 , R 2 , R 3 , R 4 and X are as defined.
12. A compound of the formula (I) according to any one of Claims 1-5 in which R 3 is hydrogen, n is 0 and m is1 or 4, X is NH or oxygen and R 1 and R 2 are as defined. -105
13. A process for preparing a compound as defined in Claim 1, formula (1), which comprises a) preparing compounds of the formula (I) in which n is 0 and R 1 , R 2 , R 3 , X and m are as defined above under formula (I) by reacting a compound of the formula R O F c C CCH2 C F in which R 3 and m are as defined under formula (1) and Y 2 is Cl, Br or OS0 2 -alkyl with a compound of the formula HX-N C R2 in which R 1 , R 2 and X are as defined under formula (1); b) preparing compounds of formula (I) in which n is 0 and X is NR 4 and R 1 , R 2 , R 3 and m are as defined under formula (I) by reacting a compound of the formula R30 1 _ | F C C 2 CH2 C N NH 2 c CHf CHjN.N ~ IV) F R 4 in which R 3 , R 4 and m are as defined under [lacuna] with a compound of the formula /R, o= c (V) R2 in which R 1 and R 2 are as defined under formula (I); and c) preparing compounds of the formula (1) in which n is 1 and R 1 , R 2 , R 3 , R 4 , X and m are as defined under formula (1) by reacting a compound of the formula C_ .. T -106 R, 13 0 F NI NII CH 2 N-1 C CHJ HcI OH (VI) in which R 3 and m are as defined above under [lacuna] with a compound of the formula RI CH C N c 11 in which Y1 is Cl, Br or OS0 2 -alkyl and X, R 1 and R 2 are as defined above under formula (I).
14. A pesticide which contains, in addition to inert auxiliaries and carriers, at least one compound of the formula (1) according to Claim 1 as active substance.
15. A process for preparing a pesticide according to Claim 14 which comprises mixing a compound of the formula (1) according to Claim 1 with inert auxiliaries and carriers.
16. A method for controlling pests, which comprises applying a compound of the formula (1) as described in Claim 1 or a composition as described in Claim 14 to the pests or their habitat.
17. The use of a compound of formula (1) as described in Claim 1 or, if appropriate, an E/Z isomer or tautomer thereof, in free form or in agrochemically useable salt form for preparing a composition as described in Claim 14.
18. A method according to Claim 14 for protecting plant propagation stock, which comprises treating the propagation stock or the location where the propagation stock is planted. Lj -107
19. The use of a compound of the formula (1) as described in Claim 1 or of a composition as described in Claim 14 for controlling pests.
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