Ortho-substituted phenylacetamides

The present invention relates to novel ortho-substituted phenylacetamides of the formula I ##STR2## where R.sup.1 is hydrogen, C.sub.1 -C.sub.18 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl which can have from one to three substituents selected from a group of 3 halogen atoms, 3 C.sub.1 -C.sub.4 -alkyl groups, a partially or completely halogenated C.sub.1 -C.sub.4 -alkenyl group and a phenyl group which can carry one or two halogen atoms and/or one C.sub.1 -C.sub.4 -alkyl group and/or one C.sub.1 -C.sub.4 -alkoxy group, or is C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.4 -alkynyl which can carry a phenyl radical, or is C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl or phenyl-C.sub.2 -C.sub.4 -alkenyl or phenoxy-C.sub.1 -C.sub.4 -alkyl where each aromatic ring can have from one to five substituents selected from a group of 2 nitro radicals, 2 cyano radicals, 5 halogen atoms and in each case three of the following: C.sub.1 -C.sub.4 -alkyl, partially or completely halogenated C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, partially or completely halogenated C.sub.2 -C.sub.4 -alkenyl and C.sub.1 -C.sub.4 -alkoxy, and of one phenyl, benzyl, phenoxy, benzyloxy or phenylthio radical, where the last two radicals in turn can have one or two of the following substituents cyano, halogen or C.sub.1 -C.sub.4 -alkyl;
a 5- or 6-membered heterocycle with from one to three hetero atoms selected from a group of two oxygen, two sulfur and three nitrogen atoms, excepting compounds with two adjacent oxygen and/or sulfur atoms, it being possible for a benzene ring or a 5- or 6-membered heteroaromatic ring with one nitrogen, oxygen or sulfur atom to be fused on to the heterocycle, and it being possible for the heterocycle to carry one halogen atom, one or two C.sub.1 -C.sub.4 -alkyl radicals or one phenyl radical;
R.sup.2 and R.sup.3 are each, independently of one another, hydrogen, cyano, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
R.sup.4 and R.sup.5 are each, independently of one another, hydrogen or C.sub.1 -C.sub.4 -alkyl or one of the two is C.sub.1 -C.sub.4 -alkoxy;
Y is oxygen, sulfur, --SO--, --SO.sub.2 --, --CH.sub.2 --O--SO.sub.2 --, --N.dbd.N--, --O--CO--, --CO--O-- or --CO--O--CH.sub.2 --, C.sub.1 -C.sub.4 -alkylene which can be partially or completely halogenated and can carry one of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, partially or completely halogenated C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, partially or completely halogenated C.sub.2 -C.sub.4 -alkenyl, C.sub.1 -C.sub.4 -alkoxy, phenyl or phenoxy, it being possible for the last two radicals in turn to have one or two of the following substituents: cyano, halogen or C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenylene or C.sub.2 -C.sub.4 -alkynylene, oxy-(C.sub.1 -C.sub.4)-alkylene, thio-(C.sub.1 -C.sub.4)-alkylene or C.sub.1 -C.sub.4 -alkyleneoxy or carbonyl-(C.sub.1 -C.sub.4)-alkylene or C.sub.1 -C.sub.4 -alkylenecarbonyl;
W is C.sub.1 -C.sub.4 -alkoxyimino, C.sub.1 -C.sub.4 -alkoxymethylene or C.sub.1 -C.sub.4 -alkylthiomethylene,
excepting compounds where R.sup.1 is hydrogen, phenyl or 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropyl, R.sup.2 to R.sup.5 are each hydrogen, Y is carbonyloxymethylene and W is methoxymethylene or methylthiomethylene.
The present invention also relates to processes for preparing these compounds, to their use as fungicides and to their use as insecticides, nematicides and acaricides and to fungicidal agents and agents for controlling pests which contain these compounds as active substances.
EP-A 310 954 discloses, inter alia, fungicidal ortho-substituted phenylacetamides of the type of compounds I, and their phenylacetonitrile precursors, where R.sup.1 is hydrogen, phenyl or 2,2-dimethyl- 3- ( 2,2--dichlorovinyl)cyclopropyl, R.sup.2 to R.sup.5 are each hydrogen, Y is carboxymethylene and W is methoxymethylene or methylthiomethylene. European patent 398 692 discloses similar compounds.
It is an object of the present invention to find novel fungicidal ortho-substituted phenylacetic acid derivatives and novel insecticidal, acaricidal and nematicidal active ingredients.
We have found that this object is achieved by the ortho-substituted phenylacetamides of the formula I defined above.
The specific meanings of the substituents in the novel compounds I are as follows:
R.sup.1
hydrogen;
branched or unbranched C.sub.1 -C.sub.18 -alkyl such as methyl, ethyl, n-propyl, isopropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 3-methylbutyl, n-pentyl, n-hexyl, n-heptyl, 2,6-dimethylheptyl, n-octyl, n-nonyl, n-decyl, n-pentadecyl, n-heptadecyl and n-octadecyl, preferably C.sub.1 -C.sub.10 -alkyl;
C.sub.3 -C.sub.8 -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, each of which can have from one to three substituents selected from a group of 3 halogen atoms such as fluorine, chlorine, bromine and iodine, especially fluorine and chlorine, 3 C.sub.1 -C.sub.4 -alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl, partially or completely halogenated C.sub.1 -C.sub.4 -alkenyl such as 2,2-dichloroethenyl, and phenyl which can carry one or two halogen atoms as mentioned above, especially fluorine and chlorine, and/or one C.sub.1 -C.sub.4 -alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl and/or one C.sub.1 -C.sub.4 -alkoxy group such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy and tert-butoxy; cyclopropyl, 1-methylcyclopropyl, 2,2-dichlorocyclopropyl, 1-( 2,2-dichlorovinyl )cyclopropyl, 1-phenylcyclopropyl, 1-(p-fluorophenyl )cyclopropyl, cyclohexyl and 1-methylcyclohexyl are preferred;
C.sub.2 -C.sub.10 -alkenyl such as vinyl, allyl, 1-propenyl, 2-propenyl, 2-methylpropenyl, 2-butenyl, 1-methylpropenyl, 3-methyl-2-butenyl, 1,3-pentadienyl, 2,6-dimethyl-5-heptenyl and 2,6-dimethyl-1,5-heptadienyl;
C.sub.2 -C.sub.4 -alkynyl such as ethynyl and 2-propynyl, which can carry a phenyl radical, eg. 2-phenylethynyl;
C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl such as methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, n-butoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl and 2-n-propoxyethyl;
C.sub.1 -C.sub.4 -alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl and tert-butoxycarbonyl, preferably methoxycarbonyl;
phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl such as benzyl, phenethyl, 3-phenyl-n-propyl and 4-phenyl-n-butyl, phenyl-C.sub.2 -C.sub.4 -alkenyl such styryl and 2-phenyl-2-propenyl or phenoxy-C.sub.1 -C.sub.4 -alkyl such as phenoxymethyl, 2-phenoxyethyl, 3-phenoxypropyl and 4-phenoxybutyl, it being possible for each of the said groups to carry on the phenyl ring a total of from one to five radicals, in particular:
one or two nitro groups,
one or two cyano groups,
up to 5 halogen atoms as mentioned above, especially fluorine and chlorine,
up to 3 C.sub.1 -C.sub.4 -alkyl groups as mentioned above,
up to 3 partially or completely halogenated C.sub.1 -C.sub.4 -alkyl groups such as fluoromethyl, chloromethyl, trifluoromethyl, trichloromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, especially trifluoromethyl,
up to 3 C.sub.2 -C.sub.4 -alkenyl groups such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl and 2-methyl-2-propenyl, especially ethenyl and 2-propenyl,
up to 3 partially or completely halogenated C.sub.2 -C.sub.4 -alkenyl groups such as 2-fluoroethenyl, 2-chloroethenyl, trifluoroethenyl, trichloroethenyl and 2-chloro-2-propenyl and
up to 3 C.sub.1 -C.sub.4 -alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy and tert-butoxy,
phenyl, benzyl, phenoxy, benzyloxy or phenylthio, each of which in turn can have one or two of the following substituents: cyano, halogen as mentioned above, especially fluorine and chlorine, or C.sub.1 -C.sub.4 -alkyl as mentioned above;
phenyl, 2-nitrophenyl, 4-nitrophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3,4-trichlorophenyl, 2,3,5-trichlorophenyl, 2,3,6-trichlorophenyl, 3,4,5-trichlorophenyl, pentafluorophenyl, pentachlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 3-tert-butylphenyl, 4-tert-butylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-tert-butyl-2-methylphenyl, 3,5-diethylphenyl, 2,3,5-trimethylphenyl, 2,4,6-trimethylphenyl, 4-cyclohexylphenyl, 3-phenoxyphenyl, 4-phenoxyphenyl, 4-phenylthiophenyl, 3-benzyloxyphenyl, 4-benzyloxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-chloromethylphenyl, 3-chloromethylphenyl, 4-chloromethylphenyl, benzyl, 4-chlorobenzyl, phenethyl, 4-chlorophenethyl, styryl, 4-chlorostyryl, phenoxy, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2-methylphenoxy, 3-methylphenoxy, 4-methylphenoxy, 2-trifluoromethylphenoxy, 3-trifluoromethylphenoxy, 4-trifluoromethylphenoxy, phenoxymethyl and 2-phenoxyethyl are preferred;
a 5- or 6-membered heterocycle with from one to three hereto atoms selected from a group of two oxygen, two sulfur and three nitrogen atoms, excepting compounds with two adjacent oxygen and/or sulfur atoms, it being possible for a benzene ring or a 5- or 6-membered heteroaromatic ring with a nitrogen, oxygen or sulfur atom to be fused on to the heterocycle, for example 2-pyrrolyl, 3-pyrrolyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-benzoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, benzothiazol-2-yl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-triazol-3-yl, 1,3,4-triazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, it being possible for the heterocycles to carry a halogen atom as mentioned above, especially fluorine and chlorine, one or two C.sub.1 -C.sub.4 -alkyl groups as mentioned above, especially methyl, or a phenyl radical, for example 5-chlorobenzothiazol-2-yl, 6-chloro-2-pyridyl, 6-methyl-2-pyridyl, 6-ethyl-2-pyridyl, 6-n-propyl-2-pyridyl, 6-isopropyl-2-pyridyl, 6-n-butyl-2-pyridyl, 6-sec-butyl-2-pyridyl and 6-tert-butyl-2-pyridyl, 6-phenyl-2-pyridyl and 4,8-dimethyl-2-quinolyl; halophenyl, C.sub.1 -C.sub.4 -alkylphenyl, di-(C.sub.1 -C.sub.4)-alkylphenyl and benzothiazol-2-yl are particularly preferred;
R.sup.2, R.sup.3
hydrogen, cyano, halogen as mentioned above, especially fluorine and chlorine,
branched or unbranched C.sub.1 -C.sub.4 -alkyl as mentioned above, especially methyl, ethyl and isopropyl;
C.sub.1 -C.sub.4 -alkoxy as mentioned above, especially methoxy; hydrogen is particularly preferred;
R.sup.4, R.sup.5
hydrogen,
branched or unbranched C.sub.1 -C.sub.4 -alkyl as mentioned above, especially methyl, ethyl, n-propyl and n-butyl;
one of the two substituents is C.sub.1 -C.sub.4 -alkoxy as mentioned above, especially methoxy;
Y
oxygen or sulfur;
--SO--, --SO.sub.2 --, --CH.sub.2 --O--SO.sub.2 --, --N.dbd.N--, --O--CO--, --CO--O-- or --CO--O--CH.sub.2 --, preferably --O--CO--, --CO--O--, --CO--O--CH.sub.2 --;
C.sub.1 -C.sub.4 -alkylene which can be partially or completely halogenated, especially fluorinated or chlorinated, and which can also carry one of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl as mentioned above, partially or completely halogenated C.sub.1 -C.sub.4 -alkyl as mentioned above, C.sub.2 -C.sub.4 -alkenyl as mentioned above, partially or completely halogenated C.sub.2 -C.sub.4 -alkenyl as mentioned above, C.sub.1 -C.sub.4 -alkoxy as mentioned above, phenyl or phenoxy, it being possible for the latter two radicals in turn to have one or two of the following substituents: cyano, halogen as mentioned above, especially fluorine and chlorine, or C.sub.1 -C.sub.4 -alkyl as mentioned above, especially methyl; methylene or ethylene is preferred;
C.sub.2 -C.sub.4 -alkenylene such as ethenylene, 2-propenylene and 2-butenylene, preferably ethenylene;
C.sub.2 -C.sub.4 -akynylene such as ethynylene, 2-propynylene and 2-butynylene, preferably ethynylene;
oxy-(C.sub.1 -C.sub.4)-alkylene such as oxymethylene, oxyethylene, oxy-n-propylene and oxy-n-butylene, preferably oxymethylene;
thio-(C.sub.1 -C.sub.4) -alkylene such as thiomethylene, thioethylene, thio-n-propylene and thio-n-butylene, preferably thiomethylene;
C.sub.1 -C.sub.4 -alkyleneoxy such as methyleneoxy, ethyleneoxy, n-propyleneoxy and n-butyleneoxy, preferably methyleneoxy;
carbonyl-(C.sub.1 -C.sub.4) -alkylene such as carbonylmethylene, carbonylethylene, carbonyl-n-propylene and carbonyl-n-butylene, preferably carbonylmethylene;
C.sub.1 -C.sub.4 -alkylenecarbonyl such as methylenecarbonyl, ethylenecarbonyl, n-propylenecarbonyl and n-butylenecarbonyl, preferably methylenecarbonyl;
carbonyloxy-(C.sub.1 -C.sub.4)-alkylene such as carbonyloxymethylene, carbonyloxyethylene, carbonyloxy-n-propylene and carbonyloxy-n-butylene, preferably carbonyloxymethylene;
W
C.sub.1 -C.sub.4 -alkoxyimino such as methoxyimino, ethoxyimino, n-propoxyimino, isopropoxyimino, n-butoxyimino, sec-butoxyimino and tert-butoxyimino, preferably methoxyimino;
C.sub.1 -C.sub.4 -alkoxymethylene such as methoxymethylene, ethoxymethylene, n-propoxymethylene, isopropoxymethylene, n-butoxymethylene, sec-butoxymethylene and tert-butoxymethylene, preferably methoxymethylene;
C.sub.1 -C.sub.4 -alkylthiomethylene such as methylthiomethylene, ethylthiomethylene, n-propylthiomethylene, isopropylthiomethylene, n-butylthiomethylene, sec-butylthiomethylene and tert-butylthiomethylene, preferably methylthiomethylene;
C.sub.1 -C.sub.4 -alkoxyimino is preferred.
Particularly suitable ortho-substituted phenylacetamides I are shown in Table 1, with compounds with R.sup.2 and R.sup.3 each being hydrogen, R.sup.4 being methyl, R.sup.5 being hydrogen and W being methoxyimino or methoxymethylene being particularly preferred. Very particularly suitable are 2-methoxyimino-2-[2-(o-methylphenoxymethyl)phenyl] acetic acid N-methylamide and 2-methoxyimino-2-[2-(o-methylphenoxymethyl)phenyl]-acetic acid N-methoxyamide.
Preparation of compounds I may result in E/Z isomer mixtures where the two isomers differ by the alkoxy or alkylthio of the substituent W being cis or trans to the amide moiety. If required, the isomers can be separated by conventional methods, eg. by crystallization or chromatography. Compounds with the E configuration (alkoxy or alkylthio of the substituent W trans to the amide moiety) are particularly preferred.
The ortho-substituted phenylacetamides I can be obtained in a variety of ways, preferably by one of the following methods:
a) reaction of phenylacetic acid derivatives II with amines III ##STR3## L is halogen, especially chlorine and bromine, or C.sub.1 -C.sub.4 -alkoxy, especially methoxy.
Preparation of ortho-substituted phenylacetamides I where R.sup.4 or R.sup.5 is C.sub.1 -C.sub.4 -alkoxy preferably starts from a phenylacetyl chloride II (L.dbd.Cl).
The reaction is normally carried out by conventional methods (eg. Organikum, 16th edition 1985, pages 409-412) in an inert solvent or diluent, advantageously in the presence of a base.
Particularly suitable solvents or diluents are chlorohydrocarbons such as dichloromethane, ethers such as dioxane, and alcohols such as methanol and ethanol.
Examples of suitable bases are alkali metal hydroxides such as sodium and potassium hydroxide, alkali metal carbonates such as sodium and potassium carbonate, alkali metal alcoholates such as sodium methylate and sodium ethylate, especially tertiary amines such as triethylamine and heteroaromatic amines such as pyridine and 4-dimethylaminopyridine. However, it is also possible to use the amine III itself as base, for complete reaction in not less than the stoichiometric amount based on II.
All the starting compounds are expediently employed in approximately the stoichiometric ratio, but in some cases an excess of one component, of up to about 10 mol %, may be advisable.
If the amine III is used as base, it is present in a larger excess.
The reaction is generally carried out at from 0.degree. to 120.degree. C., in particular at the boiling point of the solvent.
If L is halogen, the reaction can also be carried out in a 2-phase system with phase-transfer catalysis. It is possible and advantageous to use for this mixture of a chlorohydrocarbon such as methylene chloride, aqueous alkali, eg. sodium hydroxide solution, and a phase-transfer catalyst such as tetra-n-butylammonium hydroxide. In this case, the reaction is carried out at, for example, from 10.degree. C. to the boiling point of one of the components of the solvent mixture.
The reaction is normally carried out under atmospheric pressure. An increase or reduction in the pressure is possible but generally has no advantages.
Phenylacetic acid derivatives II where L is halogen are known or can be prepared by known processes (eg. Organikum, 16th edition 1985, pages 415, 622 and 423).
The phenylacetic acid derivatives II where L is C.sub.1 -C.sub.4 -alkoxy are disclosed in EP-A 178 826 and EP-A 226 917 (X.dbd..dbd.CH--O--alkyl), EP-A 244 077 (X.dbd..dbd.CH--S--alkyl) and EP-A 253 213 and EP-A 254 426 (X.dbd..dbd.N--O--alkyl) or can be prepared by similar processes.
For example, the phenylacetic acid derivatives II with Y=oxymethylene, thiomethylene or --CO--O--CH.sub.2 -- are obtained by nucleophilic substitution on benzyl halides VI ##STR4## b) Hydrolysis of phenylacetonitriles IV ##STR5##
The hydrolysis of the phenylacetonitriles IV is normally catalyzed by acid or base by conventional methods [cf., for example, Beckwith in: Zabicky The Chemistry of Amides, pages 119 to 125 ( 1970 ) and Synthesis, 243 (1980)] in an inert solvent or diluent.
Particularly suitable solvents are alcohols such as tert-butanol and ethylene glycol.
Particularly suitable acids are concentrated mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid, and preferred bases are alkali metal hydroxides such as sodium and potassium hydroxide.
The reaction is normally carried out at from 0.degree. to 200.degree. C., in particular from 20.degree. C. to the boiling point of the solvent.
The statements made for method (a) apply to the ratios of amounts and the pressure.
Phenylacetonitriles of the formula IV are disclosed, for example, in EP-A 310 954 or can be prepared by the methods described therein.
The ortho-substituted phenylacetamides I where R.sup.4 and R.sup.5 are each hydrogen can be alkylated on the amide nitrogen by conventional processes [eg. Challis in: Zabicky The Chemistry of Amides, pages 731-857 (1970)]: ##STR6## Alk is C.sub.1 -C.sub.4 -alkyl, X is halogen, especially bromine and iodine.
This normally entails conversion of the phenylacetamides I where R.sup.4 and R.sup.5 are each hydrogen, in an inert solvent or diluent, with a base into the anions and reaction of the latter with an alkyl halide, preferably an alkyl iodide.
Particularly suitable solvents or diluents are ethers such as tetrahydrofuran and dioxane.
Particularly suitable bases are alkali metal hydroxides such as sodium and potassium hydroxide and alkali metal hydrides such as sodium and potassium hydride.
The reaction is generally carried out at from 0.degree. to 100.degree. C., in particular at the boiling point of the solvent.
The statements made for method (a) apply to the ratio of amounts and the pressure.
The ortho-substituted phenylacetamides I are suitable as fungicides and for controlling pests such as insects, nematodes and acarids.
The ortho-substituted phenylacetamides I have excellent activity against a wide spectrum of fungi which are pathogenic for plants, especially from the classes of Ascomycetes and Basidiomycetes. Some of them have systemic activity and can be employed as leaf and soil fungicides.
They are particularly important for controlling a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybean, coffee, sugarcane, grapevines, fruit and ornamental plants and vegetables such as cucumbers, beans and pumpkins, and on the seeds of these plants.
They are particularly suitable for controlling the following plant diseases:
Erysiphe graminis (powdery mildew) in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkins,
Podosphaera leucotricha on apples,
Uncinula necator on grapevines,
puccinia species on cereals,
rhizoctonia species on cotton and lawns,
ustilago species on cereals and sugarcane,
Venturia inaequalis (scab) on apples,
helminthosporium species on cereals,
Septoria nodorum on wheat,
Botrytis cinerea (gray mold) on strawberries, grapevines,
Cercospora arachidicola on peanuts,
Pseudocercosporella herpotrichoides on wheat, barley,
Pyricularia oryzae on rice,
Phytophthora infestans on potatoes and tomatoes,
fusarium and verticillium species on various plants,
Plasmopara viticola on grapevines,
alternaria species on vegetables and fruit.
The compounds are applied by treating the fungi or the plants, seeds, materials or soil to be protected from fungal attack with a fungicidal amount of the active ingredients. The application is carried out before or after infection of the materials, plants or seeds by the fungi.
The ortho-substituted phenylacetamides I are also suitable for controlling pests from the classes of insects, arachnids and nematodes. They can be employed as pesticides in crop protection and in the hygiene, store protection and veterinary sectors.
The insect pests include:
from the order of Lepidoptera, for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Heliothis armigera, Hellothis virescens, Hellothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusia includens, Phyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis;
from the order of Coleoptera, for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria;
from the order of Diptera, for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineate, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa;
from the order of Thysanoptera, for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci;
from the order of Hymenoptera, for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minute, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta;
from the order of Heteroptera, for example Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor;
from the order of Homoptera, for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dyasphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum and Viteus vitifolii;
from the order of Isoptera, for example Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis;
from the order of Orthoptera, for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus birittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus;
from the class of Arachnoidea, for example arachnids (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobins megnini, Paratetranychus pilosus, Permanyssus gallinae, Phyllocaptrata oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae;
from the class of nematodes, for example root knot nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycinae, Heterodera schatii, Heterodera triflolii, stem and leaf eelworms, eg. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.
The active ingredients can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend on the purposes for which they are used; they ought in every case to ensure fine and uniform distribution of the ortho-substituted phenylacetamide. The formulations are prepared in a conventional manner, eg. by extending the active ingredient with solvents and/or carriers, if required using emulsifiers and dispersants, it being possible to use other organic solvents as auxiliary solvents when water is used as diluent.
Suitable for preparing directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, also coaltar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, tetrachloromethane, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, highly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.
Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized, as such or dissolved in an oil or solvent, using wetting agents, adhesion promoters, dispersants or emulsifiers in water. However, concentrates suitable for dilution with water can also be prepared from active substance, wetting agent, adhesion promoter, dispersant or emulsifier and, possibly, solvent or oil.
Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ethers, products of the condensation of sulfonated naphthalene and naphthalene derivatives with formaldehyde, products of the condensation of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol ester, lignin sulfite waste liquors and methylcellulose.
Powders and dusting and broadcasting agents can be prepared by mixing or grinding together the active substances with a solid carrier.
The concentrations of active ingredient in the formulations ready for use can vary within wide limits.
The agents very generally contain from 0.0001 to 95, preferably from 0.01 to 90, % by weight of active ingredient.
Formulations containing more than 95% by weight of active ingredient can be applied very successfully by the ultra low volume (ULV) method, in which case even the active ingredient without additives can be used.
Examples of such formulations are:
I. a solution of 90 parts by weight of compound No. 87 and 10 parts by weight of N-methyl-.alpha.-pyrrolidone, which is suitable for application in the form of very small drops;
II. a mixture of 20 parts by weight of compound No. 93, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate, 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil; a fine dispersion of the solution in water is used;
III. An aqueous dispersion of 20 parts by weight of compound No. 133, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil;
IV. an aqueous dispersion of 20 parts by weight of compound No. 242, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction of boiling point 210.degree. to 280.degree. C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil;
V. a mixture, ground in a hammer mill, of 80 parts by weight of compound No. 252, 3 parts by weight of sodium diisobutylnaphthalene-.alpha.-sulfonate, 10 parts by weight of the sodium salt of a ligninsulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel; a fine dispersion of the mixture in water can be sprayed;
VI. an intimate mixture of 3 parts by weight of compound No. 449 and 97 parts by weight of finely divided kaolin; this dusting agent contains 3% by weight of active ingredient;
VII. an intimate mixture of 30 parts by weight of compound No. 494, 92 parts by weight of powdered silica gel and 8 parts by weight of liquid paraffin which has been sprayed on to the surface of this silica gel; this formulation makes the active ingredient adhere well;
VIII. a stable aqueous dispersion of 40 parts by weight of compound No. 585, 10 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted;
IX. a stable oily dispersion of 20 parts by weight of compound No. 587, 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate and 68 parts by weight of a liquid paraffin.
Granules, eg. coated, impregnated or homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, attapulgite, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, bark meal, wood meal and nutshell meal, celluloso powders and other solid carriers.
The application rates in fungicidal agents depend on the nature of the desired effect and range from 0.02 to 3 kg of active ingredient per ha. The novel compounds can also be used to protect materials (wood), eg. against Paecilomyces variotii.
For treating seeds, in general from 0.001 to 50 g, preferably 0.01 to 10 g, of active ingredient are required per kilogram of seeds.
The application rate for controlling insects in the open is from 0.02 to 10, preferably 0.1 to 2.0 kg/ha active ingredient.
In these application forms, the novel agents can also be mixed with other active ingredients, eg. with herbicides, insecticides, growth regulators, fungicides or fertilizers. These agents can be added to the novel agents in the ratio of from 1:10 to 10:1 by weight, where appropriate just before application (tank mix). Mixing with fungicides or insecticides in many cases results in an extension of the spectrum of action.
The agents and the formulations prepared therefrom ready for use, such as solutions, emulsions, suspensions, powders, dusts, pastes or granules, are applied in a conventional manner, for example by spraying, atomizing, dusting, broadcasting, treating seeds or watering.

PREPARATION EXAMPLES
Example 1
2-Methoxyimino-2-[2-(m-chlorophenoxymethyl)phenyl]acetamide ##STR7##
7.0 g (23 mmol) of 2-methoxyimino-2-[2-(m-chlorophenoxymethyl)phenyl]acetonitrile were added to a mixture of 50 ml of glycol and 10 ml of a 25% by weight aqueous solution of potassium hydroxide, and the reaction mixture was then heated at 80.degree. C. for 2 hours. The solid was then separated off, washed with methyl tert-butyl ether and dried. Yield: 58%; .sup.1 H-NMR (in CDCl.sub.3, TMS as standard): d=4.00(s,3H); 5.18(s,2H); 6.10(sbr, 1H); 6.75(sbr, 1H); 6.78(d, 1H); 6.92(m,2H); 7.10-7.50(m,5H).
Example 2
2-Methoxyimino-2-[2-(o,p-dimethylphenoxymethyl)phenyl]acetic acid N-methylamide ##STR8##
0.465 g (15 mmol) of monomethylamine dried over potassium hydroxide was passed at about 25.degree. C. into a solution of 5.0 g (15 mmol) of 2-methoxyimino-2-[2-(o,p-dimethylphenoxymethyl)phenyl]acetyl chloride in 30 ml of dichloromethane. This mixture was stirred for one hour and then diluted with 70 ml of dichloromethane. By-products were extracted with 100 ml of water and then the organic phase was worked up in a conventional manner to give the product. Yield: 88% (oil);
.sup.1 H-NMR (in CDCl.sub.3, TMS as standard): d=2.20(s,3H); 2.25(s,3H); 2.90(d,3H); 3.94(s,3H); 4.93(s,2H); 6.70-7.60(m,7H).
Example 3
2-Methoxyimino-2-(2-benzyloxyphenyl)acetic acid N,N-dimethylamide ##STR9##
A solution of 4.9 g (16.4 mmol) of methyl 2-methoxyimino-2-(2-benzyloxyphenyl)acetate and 0.9 g (20 mmol) of dimethylamine in 20 ml of methanol was stirred at about 25.degree. C. for 60 hours. After removal of the solvent, the crude product was purified by chromatography on silica gel (methyl tert-butyl ether/n-hexane mixture as eluent). Yield: 66%;
.sup.1 H-NMR (in CDCl.sub.3, TMS as standard): d=3.38(s,3H); 3.49(s,3H); 4.01(s,3H); 5.03(s,2H); 6.90-7.10(m,2H); 7.30-7.40(m,6H); 8.75(d, 1H).
Example 4
2-Methoxyimino-2-[2-(o,p-dimethylphenoxymethyl)phenyl]-acetic acid N,N-dimethylamide ##STR10##
0.675 g (15 mmol) of dried dimethylamine was reacted with 5.0 g (15 mmol) of 2-methoxyimino-2-[2-(o,p-dimethylphenoxymethyl)phenyl]acetyl chloride in a similar manner to Example 2. Yields 78% (oil);
.sup.1 H-NMR (in CDCl.sub.3, TMS as standard): d=2.20(s,3H); 2.23(s,3H); 3.02(s,3H); 3.18(s,3H); 3.95(s,3H); 5.02(s,2H); 6.60-7.60(m,7H).
Further final products I which were or can be prepared in the same way are listed in Table 1.
TABLE__________________________________________________________________________ ##STR11## I (R.sup.2, R.sup.3 H)No. Y R.sup.1 R.sup.4 R.sup.5 W Physical data__________________________________________________________________________ 1 CH.sub.2 H H H NOCH.sub.3 2 CHCl H H H NOCH.sub.3 3 CHBr H H H NOCH.sub.3 4 CHI H H H NOCH.sub.3 5 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H H NOCH.sub.3 6 CH.sub.2 CH.sub.2 2-FC.sub.6 H.sub.4 H H NOCH.sub.3 7 CH.sub.2 CH.sub.2 3-FC.sub.6 H.sub.4 H H NOCH.sub.3 8 CH.sub.2 CH.sub.2 4-FC.sub.6 H.sub.4 H H NOCH.sub.3 9 CH.sub.2 CH.sub.2 2-ClC.sub.6 H.sub.4 H H NOCH.sub.3 10 CH.sub.2 CH.sub.2 3-ClC.sub.6 H.sub.4 H H NOCH.sub.3 11 CH.sub.2 CH.sub.2 4-ClC.sub.6 H.sub.4 H H NOCH.sub.3 12 CH.sub.2 CH.sub.2 2-BrC.sub.6 H.sub.4 H H NOCH.sub.3 13 CH.sub.2 CH.sub.2 4-BrC.sub.6 H.sub.4 H H NOCH.sub.3 14 CH.sub.2 CH.sub.2 2-IC.sub.6 H.sub.4 H H NOCH.sub.3 15 CH.sub.2 CH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 16 CH.sub.2 CH.sub.2 3-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 17 CH.sub.2 CH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 18 CH.sub.2 CH.sub.2 2-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 19 CH.sub.2 CH.sub.2 3-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 20 CH.sub.2 CH.sub.2 4-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 21 CH.sub.2 CH.sub.2 2-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 22 CH.sub.2 CH.sub.2 3-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 23 CH.sub.2 CH.sub.2 4-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 24 CH.sub.2 CH.sub.2 2,4-Cl.sub.2 C.sub.6 H.sub.3 H H NOCH.sub.3 25 CH.sub.2 CH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 H H NOCH.sub.3 26 CH.sub.2 CH.sub.2 2,4,6-(CH.sub.3).sub.3 lC.sub.6 H.sub.2 H H NOCH.sub.3 27 CH.sub.2 CH.sub.2 Pyridin-3-yl H H NOCH.sub.3 28 CH.sub.2 CH.sub.2 Furan-2-yl H H NOCH.sub.3 29 CH.sub.2 CH.sub.2 6-CH.sub.3 -Pyridin-2-yl H H NOCH.sub.3 30 CH.sub.2 CH.sub.2 Benzothiazol-2-yl H H NOCH.sub.3 31 CHCH C.sub.6 H.sub.5 H H NOCH.sub.3 32 CHCH 2-FC.sub.6 H.sub.4 H H NOCH.sub.3 33 CHCH 3-FC.sub.6 H.sub.4 H H NOCH.sub.3 34 CHCH 4-FC.sub.6 H.sub.4 H H NOCH.sub.3 35 CHCH 2-ClC.sub.6 H.sub.4 H H NOCH.sub.3 36 CHCH 3-ClC.sub.6 H.sub.4 H H NOCH.sub.3 37 CHCH 4-ClC.sub.6 H.sub.4 H H NOCH.sub.3 38 CHCH 2-BrC.sub.6 H.sub.4 H H NOCH.sub.3 39 CHCH 4-BrC.sub.6 H.sub.4 H H NOCH.sub.3 40 CHCH 2-IC.sub.6 H.sub.4 H H NOCH.sub.3 41 CHCH 2-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 42 CHCH 3-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 43 CHCH 4-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 44 CHCH 2-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 45 CHCH 3-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 46 CHCH 4-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 47 CHCH 2-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 48 CHCH 3-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 49 CHCH 4-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 50 CHCH 2,4-Cl.sub.2 C.sub.6 H.sub.3 H H NOCH.sub.3 51 CHCH 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 H H NOCH.sub.3 52 CHCH Pyridin-3-yl H H NOCH.sub.3 54 CHCH Furan-2-yl H H NOCH.sub.3 55 CHCH 6-CH.sub.3 -Pyridin-2-yl H H NOCH.sub.3 56 CHCH Benzothiazol-2-yl H H NOCH.sub.3 57 CH.sub.2 O C.sub.6 H.sub.5 H H NOCH.sub.3 58 CH.sub.2 O 2-FC.sub.6 H.sub.4 H H NOCH.sub.3 59 CH.sub.2 O 3-FC.sub.6 H.sub.4 H H NOCH.sub.3 60 CH.sub.2 O 4-FC.sub.6 H.sub.4 H H NOCH.sub.3 61 CH.sub.2 O 2-ClC.sub.6 H.sub.4 H H NOCH.sub.3 62 CH.sub.2 O 3-ClC.sub.6 H.sub. 4 H H NOCH.sub.3 63 CH.sub.2 O 4-ClC.sub.6 H.sub.4 H H NOCH.sub.3 64 CH.sub.2 O 2-BrC.sub.6 H.sub.4 H H NOCH.sub.3 65 CH.sub.2 O 4-BrC.sub.6 H.sub.4 H H NOCH.sub.3 66 CH.sub.2 O 2-IC.sub.6 H.sub.4 H H NOCH.sub.3 67 CH.sub.2 O 2-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 68 CH.sub.2 O 3-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 69 CH.sub.2 O 4-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 70 CH.sub.2 O 2-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 71 CH.sub.2 O 3-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 72 CH.sub.2 O 4-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 73 CH.sub.2 O 2-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 74 CH.sub.2 O 3-CF.sub.3 C.sub.6 H.sub.4 H H N OCH.sub.3 75 CH.sub.2 O 4-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 76 CH.sub.2 O 2,4-Cl.sub.2 C.sub.6 H.sub.3 H H NOCH.sub.3 77 CH.sub.2 O 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 H H NOCH.sub.3 78 CH.sub.2 O 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 H H NOCH.sub.3 79 CH.sub.2 O Pyridin-3-yl H H NOCH.sub.3 80 CH.sub.2 O Furan-2-yl H H NOCH.sub.3 81 CH.sub.2 O 6-CH.sub.3 -Pyridin-2-yl H H NOCH.sub.3 82 CH.sub.2 O Benzothiazol-2-yl H H NOCH.sub.3 83 O-CH.sub.2 H H H NOCH.sub.3 84 O-CH.sub.2 C.sub.6 H.sub.5 H H NOCH.sub.3 85 O-CH.sub.2 2-FC.sub.6 H.sub.4 H H NOCH.sub.3 86 O-CH.sub.2 3-FC.sub.6 H.sub.4 H H NOCH.sub.3 87 O-CH.sub.2 4-FC.sub.6 H.sub.4 H H NOCH.sub.3 M.p. 127-9.degree. C.; 1R (Kbr; 3371, 3184, 1652, 1507, 1249, 1050, 824 cm.sup.-1 88 OCH.sub.2 2-ClC.sub.6 H.sub.4 H H NOCH.sub.3 89 OCH.sub.2 3-ClC.sub.6 H.sub.4 H H NOCH.sub.3 M.p. 104-5.degree. C.; IR (KBr); 3416, 1663, 1559, 1482, 1249, 1045, 904, 775 cm.sup.-1 90 OCH.sub.2 4-ClC.sub.6 H.sub.4 H H NOCH.sub.3 M.p. 105-10.degree. C. 91 OCH.sub.2 2-BrC.sub.6 H.sub.4 H H NOCH.sub.3 M.p. 88-90.degree. C.; 1H- NMR(CDCl.sub.3); .delta.- 4.13(s, 3H), 5.35 (s, 2H), 6.85(m, 2H), 7.25(m, 1H), 7.58 (m, 3H), 7.78(d, 1H), 7.86(d, 1H) 92 OCH.sub.2 4-BrC.sub.6 H.sub.4 H H NOCH.sub.3 93 OCH.sub.2 2-IC.sub.6 H.sub.4 H H NOCH.sub.3 M.p. 148- 50.degree. C.; IR(KBr); 3373, 1652, 1474, 1249, 1055, 749 94 OCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 95 OCH.sub.2 3-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 96 OCH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 M.p. 100-2.degree. C.; IR(KBr); 1674, 1510, 1239, 1042, 814 97 OCH.sub.2 2-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 98 OCH.sub.2 3-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3 99 OCH.sub.2 4-OCH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3100 OCH.sub.2 2-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3101 OCH.sub.2 3-CF.sub.3 C.sub.6 H.sub.4 H H N OCH.sub.3102 OCH.sub.2 4-CF.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3103 OCH.sub.2 2,4-Cl.sub.2 C.sub.6 H.sub.3 H H NOCH.sub.3104 OCH.sub.2 2,4-(CH.sub.3)C.sub.6 H.sub.3 H H NOCH.sub.3105 OCH.sub.2 2,4,6-(CH.sub.3)C.sub.6 H.sub.2 H H NOCH.sub.3106 OCH.sub.2 2-CH.sub.3 -4-ClC.sub.6 H.sub.3 H H NOCH.sub.3107 OCH.sub.2 3-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 H H NOCH.sub.3108 OCH.sub.2 4-C.sub.6 H.sub.5 C.sub.6 H.sub.4 H H NOCH.sub.3109 OCH.sub.2 2-Cl, 4-CH.sub.3 C.sub.6 H.sub.3 H H NOCH.sub.3110 OCH.sub.2 Pyridin-2-yl N H NOCH.sub.3111 OCH.sub.2 6-CH.sub.3 -Pyridin-2-yl H H NOCH.sub.3112 OCH.sub.2 2-Cl-Pyridin-2-yl H H NOCH.sub.3113 OCH.sub.2 Benzathiazol-2-yl H H NOCH.sub.3114 O H H H NOCH.sub.3115 O C.sub.6 H.sub.5 H H NOCH.sub.3116 O 3-C.sub.6 H.sub.5 C.sub.6 H.sub.4 H H NOCH.sub.3117 O 3-OC.sub.3 H.sub.4 C.sub.6 H.sub.4 H H NOCH.sub.3118 O Pyridin-2-yl H H N-OCH.sub.3119 O 6-C.sub.6 H.sub.5 -Pyridin-2-yl H H NOCH.sub.3120 O CH.sub.2 CHCH.sub.2 H H NOCH.sub.3121 O 3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 H H NOCH.sub.3122 O 3-C.sub.6 H.sub.5 SC.sub.6 H.sub.4 H H NOCH.sub.3123 O 3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4 H H NOCH.sub.3124 CC CH.sub.3 H H NOCH.sub.3125 CC C.sub.6 H.sub.5 H H NOCH.sub.3126 S C.sub.6 H.sub.5 H H NOCH.sub.3127 S 2-ClC.sub.6 H.sub.4 H H NOCH.sub.3128 SCH.sub.2 C.sub.6 H.sub.5 H H NOCH.sub.3129 SCH.sub.2 4-ClC.sub.6 H.sub.4 H H NOCH.sub.3130 SCH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 H H NOCH.sub.3131 S CH.sub.2 6-CH.sub.3 -Pyridin-2-yl H H NOCH.sub.3132 S-CH.sub.2 6-Cl-Pyridin-2-yl H H NOCH.sub.3133 S-CH.sub.2 Benzothiazol-2-yl H H NOCH.sub.3 M.p. 171-8.degree. C.; IR(KBr); 3388, 3155, 1672, 1650, 1429, 1037, 989, 748 cm.sup.-1134 SCH.sub.2 5-Cl-Benzothiazol-2-yl H H N-OCH.sub.3135 SCH.sub.2 6-Cl-Benzothiazol-2-yl H H N-OCH.sub.3136 COO CH.sub.3 H H NOCH.sub.3137 COO C.sub.6 H.sub.5 H H N-OCH.sub.3138 OOC CH.sub.3 H H N-OCH.sub.3139 OOC C.sub.6 H.sub.5 H H NOCH.sub.3140 OOC H H H N-OCH.sub.3141 COCH.sub.2 H H H N-OCH.sub.3142 COCH.sub.2 CH.sub.3 H H N-OCH.sub.3143 COCH.sub.2 C.sub.6 H.sub.5 H H N-OCH.sub.3144 COCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 H H N-OCH.sub.3145 COCH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 H H N-OCH.sub.3146 COCH.sub.2 2-ClC.sub.6 H.sub.4 H H N-OCH.sub.3147 CH.sub.2 CO H H H N-OCH.sub.3148 CH.sub.2 CO C.sub.6 H.sub.5 H H N-OCH.sub.3149 NN C.sub.6 H.sub.5 H H N-OCH.sub.3150 CH.sub.2 H CH.sub.3 CH.sub.3 N-OCH.sub.3150 CH.sub.2 H CH.sub.3 CH.sub.3 N-OCH.sub.3151 CHCl H CH.sub.3 CH.sub.3 N-OCH.sub.3152 CHBr H CH.sub.3 CH.sub.3 N-OCH.sub.3153 CHI H CH.sub.3 CH.sub.3 N-OCH.sub.3154 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 N-OCH.sub.3155 CH.sub.2 CH.sub.2 2-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3156 CH.sub.2 CH.sub.2 3-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3157 CH.sub.2 CH.sub.2 4-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3158 CH.sub.2 CH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3159 CH.sub.2 CH.sub.2 3-Cl C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3160 CH.sub.2 CH.sub.2 4-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3161 CH.sub.2 CH.sub.2 2-BrC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3162 CH.sub.2 CH.sub.2 4-BrC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3163 CH.sub.2 CH.sub.2 2-IC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3164 CH.sub.2 CH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3165 CH.sub.2 CH.sub.2 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3166 CH.sub.2 CH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3167 CH.sub.2 CH.sub.2 2-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3168 CH.sub.2 CH.sub.2 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3169 CH.sub.2 CH.sub.2 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3170 CH.sub.2 CH.sub.2 2-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3171 CH.sub.2 CH.sub.2 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3172 CH.sub.2 CH.sub.2 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 N-OCH.sub.3173 CH.sub.2 CH.sub.2 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 CH.sub.3 N-OCH.sub.3174 CH.sub.2 CH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 CH.sub.3 N-OCH.sub.3175 CH.sub.2 CH.sub.2 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 CH.sub.3 N-OCH.sub.3176 CH.sub.2 CH.sub.2 Pyridin-3-yl CH.sub.3 CH.sub.3 NOCH.sub.3177 CH.sub.2 CH.sub.2 Furan-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3178 CH.sub.2 CH.sub.2 6-CH.sub.3 Pyridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3179 CH.sub.2 CH.sub.2 Benzothiazol-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3180 CHCH C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3181 CHCH 2-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3182 CH CH 3-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3183 CHCH 4-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3184 CHCH 2-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3185 CHCH 3-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3186 CHCH 4-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3187 CHCH 2-BrC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3188 CHCH 4-BrC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3189 CHCH 2-IC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3190 CHCH 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3191 CHCH 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3192 CHCH 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3193 CHCH 2-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3194 CHCH 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3195 CHCH 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3196 CHCH 2-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3197 CHCH 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3198 CHCH 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3199 CHCH 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3200 CHCH 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3201 CHCH 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 CH.sub.3 NOCH.sub.3202 CHCH Pyridin-3-yl CH.sub.3 CH.sub.3 NOCH.sub.3203 CHCH Furan-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3204 CHCH 6-CH.sub.3 -Pyridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3205 CHCH Benzathiazol-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3206 CH.sub.2 O C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3207 CH.sub.2 O 2-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3208 CH.sub.2 O 3-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3209 CH.sub.2 O 4-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3210 CH.sub.2 O 2-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3211 CH.sub.2 O 3-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3212 CH.sub.2 O 4-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3213 CH.sub.2 O 2-BrC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3214 CH.sub.2 O 4-BrC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3215 CH.sub.2 O 2-IC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3216 CH.sub.2 O 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3217 CH.sub.2 O 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3218 CH.sub.2 O 4-Cl.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3219 CH.sub.2 O 2-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3220 CH.sub.2 O 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3221 CH.sub.2 O 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3222 CH.sub.2 O 2-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3223 CH.sub.2 O 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3224 CH.sub.2 O 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3225 CH.sub.2 O 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3226 CH.sub.2 O 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3227 CH.sub.2 O 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 CH.sub.3 NOCH.sub.3228 CH.sub.2 O Pyridin-3-yl CH.sub.3 CH.sub.3 NOCH.sub.3229 CH.sub.2 O Furan-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3230 CH.sub.2 O 6-CH.sub.3 -PYridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3231 CH.sub.2 O Benzothiazol-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3232 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3233 OCH.sub.2 2-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3234 OCH.sub.2 3-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3235 OCH.sub.2 4-FC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3236 OCH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3237 OCH.sub.2 3-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3238 OCH.sub.2 4-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3239 OCH.sub.2 2-BrC.sub.4 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3240 OCH.sub.2 4-BrC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3241 OCH.sub.2 2-IC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3242 OCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3 M.p. 75.degree. C., 1H NMR (CDCl.sub.3) .delta.2.26(s, 3H); 3.02, 3.17(2s, 6H); 3.9 7(s, 3H); 5.17(s, 2H); 6.85(m, 2H); 7.15 (m, 2H); 7.40(m, 3H); 7.60(d, 1H)243 OCH.sub.2 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3244 OCH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3245 OCH.sub.2 2-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3246 OCH.sub.2 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3247 OCH.sub.2 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3248 OCH.sub.2 2-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3249 OCH.sub.2 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3250 OCH.sub.2 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3251 OCH.sub.2 2,4-Cl.sub.2 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3252 OCH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3 oil; 1H-NMR(CDCl.sub.3); .delta. 2.23(s, 3H); 2.27(s, 3H); 3.03, 3.18(2s, 6H); 3.93(s, 3H); 5.02 (s, 2H); 6.75(d, 1H); 6.9(m, 2H); 7.35 (m, 3H); 7.57(d, 1H)253 OCH.sub.2 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 CH.sub.3 NOCH.sub.3254 OCH.sub.2 2-CH.sub.3, 4-ClC.sub.6 H.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3255 OCH.sub.2 3-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3256 OCH.sub.2 2-Cl, 4-CH.sub.3 C.sub.6 H.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3257 OCH.sub.2 4-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3258 OCH.sub.2 Pyridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3259 OCH.sub.2 6-CH.sub.3 -Pyridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3260 OCH.sub.2 6-Cl-Pyridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3261 OCH.sub.2 Benzothiazol-2-yl CH.sub.3 CH.sub.3 N OCH.sub.3262 O H CH.sub.3 CH.sub.3 NOCH.sub.3263 O C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3264 O 3-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3265 O 3-n-C.sub.3 H.sub.7 OC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3266 O Pyridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3267 O 6-C.sub.6 H.sub.5 -Pyridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3268 O CH.sub.2 CHCH.sub.2 CH.sub.3 CH.sub.3 NOCH.sub.3269 O 3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3270 O 3-C.sub.6 H.sub.5 SC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3271 O 3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3272 CC CH.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3273 CC C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3274 S C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3275 S 2-ClC.sub. 6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3276 SCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3277 SCH.sub.2 4-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3278 SCH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3279 SCH.sub.2 2-CH.sub.3 -Pyridian-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3280 SCH.sub.2 6-Cl-Pyridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3281 SCH.sub.2 Benzothiazol-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3282 SCH.sub.2 5-Cl-Benzothiazol-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3283 SCH.sub.2 6-Cl-Benzothiazol-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3284 COO CH.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3285 COO C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3286 OCO CH.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3287 OCO C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3288 OCO H CH.sub.3 CH.sub.3 NOCH.sub.3289 COCH.sub.2 H CH.sub.3 CH.sub.3 NOCH.sub. 3290 COCH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3291 COCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3292 COCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3293 COCH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.3294 COCH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3295 COCH.sub.2 Pyridin-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3296 COCH.sub.2 Furan-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3297 COCH.sub.2 Benzathiazol-2-yl CH.sub.3 CH.sub.3 NOCH.sub.3298 CH.sub.2 CO H CH.sub.3 CH.sub.3 NOCH.sub.3299 CH.sub.2 CO C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3300 NN C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 NOCH.sub.3301 COOCH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 NOCH.sub.2302 COOCH.sub.2 tert.-C.sub.4 H.sub.9 CH.sub.3 CH.sub.3 NOCH.sub.2303 COOCH.sub.2 3-Heptyl CH.sub.3 CH.sub.3 N OCH.sub.2304 COOCH.sub.2 Cyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2305 COOCH.sub.2 1-Methylcyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2306 COOCH.sub.2 2-Methylcyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2307 COOCH.sub.2 2,2-Dimethylcyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2308 COOCH.sub.2 2,2-Dichlorocyctopropyl CH.sub.3 CH.sub.3 NOCH.sub.2309 COOCH.sub.2 2,2-methyl-3-(2,2-Dichloro- CH.sub.3 CH.sub.3 NOCH.sub.2 vinyl)cyclopropyl310 COOCH.sub.2 2-Phenylcyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2311 COOCH.sub.2 1-(2-Fluorophenyl)cycloproply CH.sub.3 CH.sub.3 NOCH.sub.2312 COOCH.sub.2 1-(2-Chlorophenyl)cyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2313 COOCH.sub.2 1-(2,6-Difluorophenyl)- CH.sub.3 CH.sub.3 NOCH.sub.2 cyclopropyl314 COOCH.sub.2 1-(2,4-Dichlorophenyl)- CH.sub.3 CH.sub.3 NOCH.sub.2 cyclopropyl315 COOCH.sub.2 1-(4-Chlorphenyl)cyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2316 COOCH.sub.2 1-(4-Methoxyphenyl)-cyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2317 COOCH.sub.2 1-(2-Methylphenyl)cyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2318 COOCH.sub.2 1-(4-Methylphenyl)cyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2319 COOCH.sub.2 1-Benzylcyclopropyl CH.sub.3 CH.sub.3 NOCH.sub.2320 COOCH.sub.2 Phenyl CH.sub.3 CH.sub.3 NOCH.sub.2321 COOCH.sub.2 4-Methylphenyl CH.sub.3 CH.sub.3 NOCH.sub.2322 COOCH.sub.2 4-Chlorophenyl CH.sub.3 CH.sub.3 NOCH.sub.2323 COOCH.sub.2 4-Fluorophenyl CH.sub.3 CH.sub.3 NOCH.sub.2324 COOCH.sub.2 2-Heptyl CH.sub.3 CH.sub.3 NOCH.sub.3325 COOCH.sub.2 Propargyl CH.sub.3 CH.sub.3 NOCH.sub.3326 COOCH.sub.2 1-Methylcyclohexyl CH.sub.3 CH.sub.3 NOCH.sub.3327 COOCH.sub.2 Cyclohexyl CH.sub.3 CH.sub.3 NOCH.sub.3328 OCH.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 CH.sub.3 NOCH.sub.3329 OCH.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5 NOCH.sub.3330 OCH.sub.2 C.sub.6 H.sub.5 n-C.sub.3 H.sub.7 CH.sub.3 NOCH.sub.3331 CH.sub.2 H CH.sub.3 H NOCH.sub.3332 CHCl H CH.sub.3 H NOCH.sub.3333 CHBr H CH.sub.3 H NOCH.sub.3334 CHO H CH.sub.3 H NOCH.sub.3335 CH.sub.2 O H CH.sub.3 H NOCH.sub.3336 CH.sub.2 OSO.sub.2 CH.sub.3 CH.sub.3 H NOCH.sub.3337 CH.sub.2 OSO.sub.2 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 H NOCH.sub.3338 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3339 CH.sub.2 CH.sub.2 2-FC.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3340 CH.sub.2 CH.sub.2 3-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3341 CH.sub.2 CH.sub.2 4-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3342 CH.sub.2 CH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3343 CH.sub.2 CH.sub.2 3-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3344 CH.sub.2 CH.sub.2 4-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3345 CH.sub.2 CH.sub.2 2-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3346 CH.sub.2 CH.sub.2 3-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3347 CH.sub.2 CH.sub.2 4-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3348 CH.sub.2 CH.sub.2 2-IC.sub.6 H.sub. 4 CH.sub.3 H NOCH.sub.3349 CH.sub.2 CH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3350 CH.sub.2 CH.sub.2 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3351 CH.sub.2 CH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3352 CH.sub.2 CH.sub.2 2-OCH.sub.3 C.sub.6.sub.4 CH.sub.3 H NOCH.sub.3353 CH.sub.2 CH.sub.2 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3354 CH.sub.2 CH.sub.2 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3355 CH.sub.2 CH.sub.2 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3356 CH.sub.2 CH.sub.2 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3357 CH.sub.2 CH.sub.2 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3358 CH.sub.2 CH.sub.2 4-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3359 CH.sub.2 CH.sub.2 4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3360 CH.sub.2 CH.sub.2 4-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3361 CH.sub.2 CH.sub.2 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3362 CH.sub.2 CH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3363 CH.sub.2 CH.sub.2 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3364 CH.sub.2 CH.sub.2 2,4,6-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3365 CH.sub.2 CH.sub.2 Pyridin-2-yl CH.sub.3 H NOCH.sub.3366 CH.sub.2 CH.sub.2 Pyridin-3-yl CH.sub.3 H NOCH.sub.3367 CH.sub.2 CH.sub.2 Furan-2-yl CH.sub.3 H NOCH.sub.3368 CH.sub.2 CH.sub.2 6-CH.sub.3 -Pyridin-2-yl CH.sub.3 H NOCH.sub.3369 CH.sub.2 CH.sub.2 6-Cl-Pyridin-2-yl CH.sub.3 H NOCH.sub.3370 CH.sub.2 CH.sub.2 Benzothiazol-2-yl CH.sub.3 H NOCH.sub.3371 CHCH C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3372 CHCH 2-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3373 CHCH 3-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3374 CHCH 4-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3375 CHCH 2-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3376 CHCH 3-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3377 CHCH 4-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3378 CHCH 2-Br-C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3379 CHCH 3-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3380 CHCH 4-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3381 CHCH 2-IC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3382 CHCH 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3383 CHCH 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3384 CHCH 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3385 CHCH 2-OCH.sub.3 C.sub.64 CH.sub.3 H NOCH.sub.3386 CHCH 3-OCH.sub.3 C.sub.6 H.sub. 4 CH.sub.3 H NOCH.sub.3387 CHCH 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3388 CHCH 2-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3389 CHCH 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3390 CHCH 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3391 CHCH 4-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3392 CHCH 4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3393 CHCH 4-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3394 CHCH 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3395 CHCH 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3396 CHCH 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3397 CHCH 2,4,6-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3398 CHCH Pyridin-2-yl CH.sub.3 H NOCH.sub.3399 CHCH Pyridin-3-yl CH.sub.3 H NOCH.sub.3400 CHCH Furan-2-yl CH.sub.3 H NOCH.sub.3401 CHCH 6-CH.sub.3 -Pyridin-2-yl CH.sub.3 H NOCH.sub.3402 CHCH 6-Cl-Pyridin-2-yl CH.sub.3 H NOCH.sub.3403 CHCH Benzothiazol-2-yl CH.sub.3 H NOCH.sub.3404 CH.sub.2 O C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3405 CH.sub.2 O 2-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3406 CH.sub.2 O 3-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3407 CH.sub.2 O 4-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3408 CH.sub.2 O 2-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3409 CH.sub.2 O 3-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3410 CH.sub.2 O 4-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3411 CH.sub.2 O 2-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3412 CH.sub.2 O 3-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3413 CH.sub.2 O 4-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3414 CH.sub.2 O 2-IC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3415 CH.sub.2 O 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3416 CH.sub.2 O 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3417 CH.sub.2 O 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3418 CH.sub.2 O 2-OCH.sub.3 C.sub.64 CH.sub.3 H NOCH.sub.3419 CH.sub.2 O 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3420 CH.sub.2 O 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3421 CH.sub.2 O 2-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3422 CH.sub.2 O 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3423 CH.sub.2 O 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3424 CH.sub.2 O 4-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3425 CH.sub.2 O 4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3426 CH.sub.2 O 4-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3427 CH.sub.2 O 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3428 CH.sub.2 O 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3429 CH.sub.2 O 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3430 CH.sub.2 O 2,4,6-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3431 CH.sub.2 O Pyridin-2-yl CH.sub.3 H NOCH.sub.3432 CH.sub.2 O Pyridin-3-yl CH.sub.3 H NOCH.sub.3433 CH.sub.2 O Furan-2-yl CH.sub.3 H NOCH.sub.3434 CH.sub.2 O 6-CH.sub.3 -Pyridin-2-yl CH.sub.3 H NOCH.sub.3435 CH.sub.2 O 6-Cl-Pyridin-2-yl CH.sub.3 H NOCH.sub.3436 CH.sub.2 O Benzothiazol-2-yl CH.sub.3 H NOCH.sub.3437 OCH.sub.2 H CH.sub.3 H NOCH.sub.3437 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3439 OCH.sub.2 2-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3440 OCH.sub.2 3-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3441 OCH.sub.2 4-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3442 OCH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3443 OCH.sub.2 3-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3444 OCH.sub.2 4-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3445 OCH.sub.2 2-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3446 OCH.sub.2 3-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3447 OCH.sub.2 3-BrC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3448 OCH.sub.2 2-IC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3449 OCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3 M.p. 105.degree. C.; 1H NMR(CDCl.sub.3); .delta.2.22 (s, 3H); 2.85(d, 3H); 3.85 (s, 3H); 4.95(s, 2H); 6.70(sbr, 1H); 6.80 (mc, 2H); 7.0-7.5 (m, 6H).450 OCH.sub.2 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3451 OCH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3452 OCH.sub.2 2-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 NOCH.sub.3453 OCH.sub.2 3-OCH.sub.3 C.sub.6 H.sub.4454 OCH.sub.2 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3455 OCH.sub.2 2-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3456 OCH.sub.2 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3457 OCH.sub.2 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3458 OCH.sub.2 2-NO.sub.2 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3459 OCH.sub.2 4-NO.sub.2 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3460 OCH.sub.2 2-CH.sub.2 ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3461 OCH.sub.2 3-CH.sub.2 ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3462 OCH.sub.2 4-CH.sub.2 ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3463 OCH.sub.2 2-C.sub.2 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3464 OCH.sub.2 3-C.sub.2 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3465 OCH.sub.2 4-C.sub.2 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3466 OCH.sub.2 3-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3467 OCH.sub.2 4-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3468 OCH.sub.2 3-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3469 OCH.sub.2 4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3470 OCH.sub.2 3-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3471 OCH.sub.2 4-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3472 OCH.sub.2 4-i-C.sub.3 H.sub.7 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3473 OCH.sub.2 4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3474 OCH.sub.2 3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3475 OCH.sub.2 4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3476 OCH.sub.2 3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3477 OCH.sub.2 4-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3478 OCH.sub.2 2,3-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3479 OCH.sub.2 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3480 OCH.sub.2 2,5-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3481 OCH.sub.2 2,6-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3482 OCH.sub.2 2,3,4-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3483 OCH.sub.2 2,3,5-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3484 OCH.sub.2 2,3,6-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3485 OCH.sub.2 3,4,5-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3486 OCH.sub.2 C.sub.6 Cl.sub.5 CH.sub.3 H NOCH.sub.3487 OCH.sub.2 C.sub.6 F.sub.5 CH.sub.3 H NOCH.sub.3488 OCH.sub.2 2-F, 4-ClC.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3489 OCH.sub.2 4-F, 2-ClC.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3490 OCH.sub.2 2-CH.sub.3.4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3491 OCH.sub.2 2-CH.sub.3, 4-c-C.sub.6 H.sub.11 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3492 OCH.sub.2 2-CH.sub.3, 4-C.sub.3 H.sub.7 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3493 OCH.sub.2 2,3-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3494 OCH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3 M.p. 88-89.degree. C.; 1R(KBr); 3411, 16 60, 1512, 1226, 1036, 98 2, 798, 766495 OCH.sub.2 2,5-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3496 OCH.sub.2 2,3,5-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3497 OCH.sub.2 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H NOCH.sub.3498 OCH.sub.2 3,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3499 OCH.sub.2 3,5(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3500 OCH.sub.2 3,5(C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3501 OCH.sub.2 4-Cyclohexyl-C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3502 OCH.sub.2 CH.sub.2 CHCH.sub.2 CH.sub.3 H NOCH.sub.3503 OCH.sub.2 CH.sub.2 CHCHCH.sub.3 CH.sub.3 H NOCH.sub.3504 OCH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 CH.sub.3 H NOCH.sub.3505 OCH.sub.2 CH.sub.2 C(CH.sub.3)CH.sub.2 CH.sub.3 H NOCH.sub.3506 OCH.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3507 OCH.sub.2 Cyclohexyl CH.sub.3 H NOCH.sub.3508 OCH.sub.2 CH.sub.2 CCH CH.sub.3 H NOCH.sub.3509 OCH.sub.2 CH.sub.2 CHCHC.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3510 OCH.sub.2 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3511 O H CH.sub.3 H NOCH.sub.3512 O C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3513 O 3-C.sub.6 H.sub.6 C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3514 O 3-n-C.sub.3 H.sub.7 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3515 O Pyridin-2-yl CH.sub.3 H NOCH.sub.3516 O 6-C.sub.6 H.sub.5 -Pyridin-2-yl CH.sub.3 H NOCH.sub.3517 O CH.sub.2 CHCH.sub.2 CH.sub.3 H NOCH.sub.3518 O 3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3519 O 3-C.sub.6 H.sub.5 SC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3520 O 3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3521 O 4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3522 O 4-C.sub.6 H.sub.5 OCH.sub.2 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3523 CC CH.sub.3 CH.sub.3 H NOCH.sub.3524 CC C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3525 S C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3526 S 2-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3527 SCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3528 SCH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3529 SCH.sub.2 4-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3530 SCH.sub.2 4-FC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3531 SCH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3532 SCH.sub.2 4-CH.sub.3 -Pyridin-2-yl CH.sub.3 H NOCH.sub.3533 SCH.sub.2 6-Cl-Pyridin-2-yl CH.sub.3 H NOCH.sub.3534 SCH.sub.2 Benzothiazol-2-yl CH.sub.3 H NOCH.sub.3535 SCH.sub.2 5-Cl-Benzothiazol-2-yl CH.sub.3 H NOCH.sub.3536 OCH.sub.2 6-Cl-Benzothiazol-2-yl CH.sub.3 H NOCH.sub.3537 OCH.sub.2 4,8-(CH.sub.3).sub.2 -Chinoyln-2-yl CH.sub.3 H NOCH.sub.3538 COO CH.sub.3 CH.sub.3 H NOCH.sub.3539 COO C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3540 OCO CH.sub.3 CH.sub.3 H NOCH.sub.3541 OCO C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3542 OCO C.sub.6 H.sub.5 CH.sub.2 CH.sub.3 H NOCH.sub.3543 OCO H CH.sub.3 H NOCH.sub.3544 COCH.sub.2 H CH.sub.3 H NOCH.sub.3545 COCH.sub.2 CH.sub.3 CH.sub.3 H NOCH.sub.3546 COCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3547 COCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3548 COCH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H NOCH.sub.3549 COCH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 H NOCH.sub.3550 CH.sub.2 CO H CH.sub.3 H NOCH.sub.3551 CH.sub.2 CO C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3552 NN C.sub.6 H.sub.5 CH.sub.3 H NOCH.sub.3553 COOCH.sub.2 CH.sub.3 CH.sub.3 H NOCH.sub.3554 COOCH.sub.2 tert.-C.sub.4 H.sub.9 CH.sub.3 H NOCH.sub.3555 COOCH.sub.2 3-Heptyl CH.sub.3 H NOCH.sub.3556 COOCH.sub.2 Cyclopropyl CH.sub.3 H NOCH.sub.3557 COOCH.sub.2 1-Methylcyclopropyl CH.sub.3 H NOCH.sub.3558 COOCH.sub.2 2-Methylcyclopropyl CH.sub.3 H NOCH.sub.3559 COOCH.sub.2 2,2-Dimethylcycylopropyl CH.sub.3 H NOCH.sub.3560 COOCH.sub.2 2,2-Dichlorocyclopropyl CH.sub.3 H NOCH.sub.3561 COOCH.sub.2 2,2-Dimethyl-3-(2,2-Dichloro- CH.sub.3 H NOCH.sub.3 vinyl)cyclopropyl562 COOCH.sub.2 1-Phenylcyclopropyl CH.sub.3 H NOCH.sub.3563 COOCH.sub.2 1-(2-Fluorophenyl)cyclopropyl CH.sub.3 H NOCH.sub.3564 COOCH.sub.2 1-(2-Chlorophenyl)cyclopropyl CH.sub.3 H NOCH.sub.3565 COOCH.sub.2 1-(2,6-Difluorophenyl)- CH.sub. 3 H NOCH.sub.3 cyclopropyl566 COOCH.sub.2 1-(2,4-Dichlorophenyl)- CH.sub.3 H NOCH.sub.3 cyclopropyl567 COOCH.sub.2 1-(4-Chlorophenyl)cyclopropyl CH.sub.3 H NOCH.sub.3568 COOCH.sub.2 1-(4-Methoxyphenyl)cyclopropyl CH.sub.3 H NOCH.sub.3569 CH.sub.2 H C.sub.2 H.sub.5 H NOCH.sub.3570 CHCl H C.sub.2 H.sub.5 H NOCH.sub.3571 CHBr H C.sub.2 H.sub.5 H NOCH.sub.3572 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 H NOCH.sub.3573 CHCH C.sub.6 H.sub.5 C.sub.2 H.sub.5 H NOCH.sub.3574 OCH.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 H NOCH.sub.3575 CH.sub.2 O C.sub.6 H.sub.5 C.sub.2 H.sub.5 H NOCH.sub.3576 O C.sub.6 H.sub.5 C.sub.2 H.sub.5 H NOCH.sub.3577 OCH.sub.2 C.sub.6 H.sub.5 OCH.sub.3 H NOCH.sub.3578 CHCH C.sub.6 H.sub.5 OCH.sub.3 H NOCH.sub.3579 CH.sub.2 H OCH.sub.3 H NOCH.sub.3580 CHCl H OCH.sub.3 H NOCH.sub.3581 CHBr H OCH.sub.3 H NOCH.sub.3582 CH.sub.2 H OCH.sub.3 CH.sub.3 NOCH.sub.3583 OCH.sub.2 C.sub.6 H.sub.5 OCH.sub.3 CH.sub.3 NOCH.sub.3584 OCH.sub.2 C.sub.6 H.sub.5 OC.sub.2 H.sub.5 H NOCH.sub.3585 OCH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 OCH.sub.3 CH.sub.3 NOCH.sub.3 oil; 1H-NMR (CDCl.sub.3); .delta.2.24, 2.28(2s, 6H); 3.21(s, 3H); 3.52(br, 3 H); 3.98(s, 3H); 5.05(s, 2H); 6.75; (d, 1H); 6.83(m, 2H); 7.40(mL, 3H); 7.64(d, 1H)586 OCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 OCH.sub.2 CH.sub.3 NOCH.sub.3 M.p. 55.degree. C.; 1H NMR (CDCl.sub.3) .delta.2.30 (s, 3H); 3.20, 3.48(2s, 6H); 3.98(s, 3H); 5.08 s, 2H); 6.85(s, 2H), 7.1 0(m, 2H); 7.40(mc, 3H); 7.65(d, 1H)587 OCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 OCH.sub.3 H NOCH.sub.3 M.p.89.degree.; 1H- NMR(CDCl.sub.3) .delta.- 2.22(s, 3H); 3.75(s, 3H); 3.94(s, 3H); 4.98(s, 2H); 6.80(m, 2H); 7.13 m, 2H); 7.25(d, 1H); 7.40 (mc, 2H); 7.55(d, 1H); 9.15(s, 1H)588 OCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 C.sub.2 H.sub.5 C.sub.2 H.sub.5 NOCH.sub.3 oil; 1H-NMR(CDCl.sub.3) .delta.- 1.18(t, 3H); 2.25(s, 3H); 3.45(d, 3H); 3.93(s, 3H); 5.09(s, 2H);6.85 (m, 2H); 7.10(mc, 2H); 7.4(m, 3H); 7.60(d, 1H)589 CH.sub.2 H CH.sub.3 H CHOCH.sub.3590 CHCl H CH.sub.3 H CHOCH.sub.3591 CHBr H CH.sub. 3 H CHOCH.sub.3592 CHI H CH.sub.3 H CHOCH.sub.3593 CH.sub.2 OH CH.sub.3 H CHOCH.sub.3594 CH.sub.2 OSO.sub.2 CH.sub.3 CH.sub.3 H CHOCH.sub.3595 CH.sub.2 OSO.sub.2 C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 H CHOCH.sub.3596 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3597 CH.sub.2 CH.sub.2 2-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3598 CH.sub.2 CH.sub.2 3-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3599 CH.sub.2 CH.sub.2 4-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3600 CH.sub.2 CH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3601 CH.sub.2 CH.sub.2 3-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3602 CH.sub.2 CH.sub.2 4-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3603 CH.sub.2 CH.sub.2 2-Br-C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3604 CH.sub.2 CH.sub.2 3-Br-C.sub. 6 H.sub.4 CH.sub.3 H CHOCH.sub.3605 CH.sub.2 CH.sub.2 4-Br-C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3606 CH.sub.2 CH.sub.2 2-IC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3607 CH.sub.2 CH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3608 CH.sub.2 CH.sub.2 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3609 CH.sub.2 CH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3610 CH.sub.2 CH.sub.2 2-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3611 CH.sub.2 CH.sub.2 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3612 CH.sub.2 CH.sub.2 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3613 CH.sub.2 CH.sub.2 2-CF.sub.3 .sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3614 CH.sub.2 CH.sub.2 3-CF.sub.3 .sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3615 CH.sub.2 CH.sub.2 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3616 CH.sub.2 CH.sub.2 4-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3617 CH.sub.2 CH.sub.2 4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3618 CH.sub.2 CH.sub.2 4-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3619 CH.sub.2 CH.sub.2 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3620 CH.sub.2 CH.sub.2 2,4-(CH.sub.3).sub.4 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3621 CH.sub.2 CH.sub.2 2.4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3622 CH.sub.2 CH.sub.2 2,4,6-C.sub.6 Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3623 CH.sub.2 CH.sub.2 Pyridin-2-yl CH.sub.3 H CHOCH.sub.3624 CH.sub.2 CH.sub.2 Pyridin-3-yl CH.sub.3 H CHOCH.sub.3625 CH.sub.2 CH.sub.2 Furan-2-yl CH.sub.3 H CHOCH.sub.3626 CH.sub.2 CH.sub.2 6-CH.sub.3 -Pyridin-2-yl CH.sub.3 H CHOCH.sub.3627 CH.sub.2 CH.sub.2 6-Cl-Pyridin-2-yl CH.sub.3 H CHOCH.sub.3628 CH.sub.2 CH.sub.2 Benzothiazol-2 yl CH.sub.3 H CHOCH.sub.3629 CHCH C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3630 CHCH 2-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3631 CHCH 3-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3632 CHCH 4-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3633 CHCH 2-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3634 CHCH 3-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3635 CHCH 4-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3636 CHCH 2-BrC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3637 CHCH 3-BrC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3638 CHCH 4-BrC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3639 CHCH 2-IC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3640 CHCH 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3641 CHCH 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3642 CHCH 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3642 CHCH 2-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3644 CHCH 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3645 CHCH 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3646 CHCH 2-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3647 CHCH 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3648 CHCH 4-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3649 CHCH 4-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3650 CHCH 4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3651 CHCH 4-C.sub.6 H.sub.6 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3652 CHCH 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3653 CHCH 2,4-(CH.sub.3).sub.4 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3654 CHCH 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3655 CHCH 2,4,6-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3656 CHCH Pyridin-2-yl CH.sub.3 H CHOCH.sub.3657 CHCH Pyridin-3-yl CH.sub.3 H CHOCH.sub.3658 CHCH Furan-2-yl CH.sub.3 H CHOCH.sub.3659 CHCH 6-CH.sub.3 -Pyridin-2-yl CH.sub.3 H CHOCH.sub.3660 CHCH 6-Cl-Pyridin-2-yl CH.sub.3 H CHOCH.sub.3661 CHCH Benzothiazol-2-yl CH.sub.3 H CHOCH.sub.3662 CH.sub.2 O C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3663 CH.sub.2 O 2-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3664 CH.sub.2 O 3-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3665 CH.sub.2 O 4-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3666 CH.sub.2 O 2-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3667 CH.sub.2 O 3-ClC.sub. 6 H.sub.4 CH.sub.3 H CHOCH.sub.3668 CH.sub.2 O 4-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3669 CH.sub.2 O 2-BrC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3670 CH.sub.2 O 3-BrC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3671 CH.sub.2 O 4-BrC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3672 CH.sub.2 O 2-IC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3673 CH.sub.2 O 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3674 CH.sub.2 O 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3675 CH.sub.2 O 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3676 CH.sub.2 O 2-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3677 CH.sub.2 O 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3678 CH.sub.2 O 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3679 CH.sub.2 O 2-CF.sub.3 .sub.6 H.sub.4 CH.sub.3 H CH OCH.sub.3680 CH.sub.2 O 3-CF.sub.3 .sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3681 CH.sub.2 O 4-CF.sub.3 .sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3682 CH.sub.2 O 4-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3683 CH.sub.2 O 4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3684 CH.sub.2 O 4-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3685 CH.sub.2 O 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3686 CH.sub.2 O 2,4-(CH.sub.3).sub.4 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3687 CH.sub.2 O 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3688 CH.sub.2 O 2,4,6-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3689 CH.sub.2 O Pyridin-2-yl CH.sub.3 H CHOCH.sub.3690 CH.sub.2 O Pyridin-3-yl CH.sub.3 H CHOCH.sub.3691 CH.sub.2 O Furan-2-yl CH.sub.3 H CHOCH.sub.3692 CH.sub. 2 O 6-CH.sub.3 -Pyridin-2-yl CH.sub.3 H CHOCH.sub.3693 CH.sub.2 O 6-Cl-Pyridin-2-yl CH.sub.3 H CHOCH.sub.3694 CH.sub.2 O Benzothiazol-2-yl CH.sub.3 H CHOCH.sub.3695 OCH.sub.2 H CH.sub.3 H CHOCH.sub.3696 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3697 OCH.sub.2 2-F-C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3698 OCH.sub.2 3-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3699 OCH.sub.2 4-F-C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3700 OCH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3701 OCH.sub.2 3-Cl-C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3702 OCH.sub.2 4-Cl-C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3703 OCH.sub.2 2-BrC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3704 OCH.sub.2 3-BrC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3705 OCH.sub.2 4-Br-C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3706 OCH.sub.2 2-IC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3707 OCH.sub.2 2-CH.sub.3 C.sub.6 H.sub. 4 CH.sub.3 H CHOCH.sub.3708 OCH.sub.2 3-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3709 OCH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3710 OCH.sub.2 2-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3711 OCH.sub.2 3-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3712 OCH.sub.2 4-OCH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3713 OCH.sub.2 2-CF.sub.3 .sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3714 OCH.sub.2 3-CF.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3715 OCH.sub.2 4-CF.sub.3 .sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3716 OCH.sub.2 2-NO.sub.2 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3717 OCH.sub.2 4-NO.sub.2 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3718 OCH.sub.2 2-CH.sub.2 ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3719 OCH.sub.2 3-CH.sub.2 ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3720 OCH.sub.2 4-CH.sub.2 ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3721 OCH.sub.2 2-C.sub.2 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3722 OCH.sub.2 3-C.sub.2 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3723 OCH.sub.2 4-C.sub.2 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3724 OCH.sub.2 3-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3725 OCH.sub.2 4-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3726 OCH.sub.2 3-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3727 OCH.sub.2 4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3728 OCH.sub.2 3-C.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3729 OCH.sub.2 4-C.sub.6 H.sub.5C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3730 OCH.sub.2 4-i-C.sub.3 H.sub.7 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3731 OCH.sub.2 4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3732 OCH.sub.2 3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3733 OCH.sub.2 4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3734 OCH.sub.2 3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3735 OCH.sub.2 4-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3736 OCH.sub.2 2,3-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3737 OCH.sub.2 2,4-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3738 OCH.sub.2 2,5-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3739 OCH.sub.2 2,6-Cl.sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3740 OCH.sub.2 2,3,4-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3741 OCH.sub.2 2,3,5-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3742 OCH.sub.2 2,3,6-Cl.sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3743 OCH.sub.2 C.sub.6 Cl.sub.5 CH.sub.3 H CHOCH.sub.3744 OCH.sub.2 C.sub.6 F.sub.5 CH.sub.3 H CHOCH.sub.3745 OCH.sub.2 2-F, 4-ClC.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3746 OCH.sub.2 4 F, 2-ClC.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3747 OCH.sub.2 2-CH.sub.3, 4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3748 OCH.sub.2 2-CH.sub.3, 4-Cyclohexyl-C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3749 OCH.sub.2 2-CH.sub.2, 4-i-C.sub.3 H.sub.7,C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3750 OCH.sub.2 2,3-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3761 OCH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3762 OCH.sub.2 2,5-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3763 OCH.sub.2 2,3,5-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3764 OCH.sub.2 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 CH.sub.3 H CHOCH.sub.3765 OCH.sub.2 3,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3766 OCH.sub.2 3,5-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3767 OCH.sub.2 3,5-(C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3768 OCH.sub.2 4-Cyclohexyl-C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3769 OCH.sub.2 CH.sub.2 CHCH.sub.2 CH.sub.3 H CHOCH.sub.3770 OCH.sub.2 CH.sub.2 CHCHCH.sub.3 CH.sub.3 H CHOCH.sub.3771 OCH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 CH.sub.3 H CHOCH.sub.3772 OCH.sub.2 CH.sub.2 C(CH.sub.3)CH.sub.2 CH.sub.3 H CHOCH.sub.3773 OCH.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3774 OCH.sub.2 Cyclohexyl CH.sub.3 H CHOCH.sub.3775 OCH.sub.2 CH.sub.2 CCH CH.sub.3 H CHOCH.sub.3716 OCH.sub.2 CH.sub.2 CHCHC.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3777 OCH.sub.2 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3778 O H CH.sub.3 H CHOCH.sub.3779 O C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3780 O 3-C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3781 O 3-n-C.sub.3 H.sub.7 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3728 O Pyridin-2-yl CH.sub.3 H CHOCH.sub.3783 O 6-C.sub.6 H.sub.5 -Pyridin-2-yl CH.sub.3 H CHOCH.sub.3784 O CH.sub.2 CHCH.sub.2 CH.sub.3 H CHOCH.sub.3785 O 3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3786 O 3-C.sub.6 H.sub.5 SC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3787 O 3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3788 O 4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3789 O 4-C.sub.6 H.sub.5 OCH.sub.2 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3790 CC CH.sub.3 CH.sub. 3 H CHOCH.sub.3791 CC C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3792 S C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3793 S 2-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3794 SCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3795 SCH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3796 SCH.sub.2 4-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3797 SCH.sub.2 4-FC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3798 SCH.sub.2 4-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3799 SCH.sub.2 6-CH.sub.3 -Pyridin-2-yl CH.sub.3 H CHOCH.sub.3800 SCH.sub.2 6-Cl-Pyridin-2-yl CH.sub.3 H CHOCH.sub.3801 SCH.sub.2 Benzothiazol-2-yl CH.sub.3 H CHOCH.sub.3802 SCH.sub.2 5-Cl-Benzothiazol-2-yl CH.sub.3 H CHOCH.sub.3803 SCH.sub.2 6-Cl-Benzothiazol-2-yl CH.sub.3 H CHOCH.sub.3804 SCH.sub.2 4,8-(CH.sub.3).sub.2 -quinoyln-2-yl CH.sub.3 H CHOCH.sub.3805 COO CH.sub.3 CH.sub.3 H CHOCH.sub.3806 COO C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3807 OCO CH.sub.3 CH.sub.3 H CHOCH.sub.3808 OCO C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3809 OCO CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3810 OCO H CH.sub.3 H CHOCH.sub.3811 COCH.sub.2 H CH.sub.3 H CHOCH.sub.3812 COCH.sub.2 CH.sub.3 CH.sub.3 H CHOCH.sub.3813 COCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3814 COCH.sub.2 2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3815 COCH.sub.2 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 CH.sub.3 H CHOCH.sub.3816 COCH.sub.2 2-ClC.sub.6 H.sub.4 CH.sub.3 H CHOCH.sub.3817 CH.sub.2 CO H CH.sub.3 H CHOCH.sub.3818 CH.sub.2 CO C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3819 NN C.sub.6 H.sub.5 CH.sub.3 H CHOCH.sub.3820 COOCH.sub.2 CH.sub.3 CH.sub.3 H CHOCH.sub.3821 COOCH.sub.2 tert.-C.sub.4 H.sub. 9 CH.sub.3 H CHOCH.sub.3822 COOCH.sub.2 1-Methyl-cyclopropyl CH.sub.3 H CHOCH.sub.3823 COOCH.sub.2 2,2-Dichtorocyctopropyl CH.sub.3 H CHOCH.sub.3824 COOCH.sub.2 2-Phenylcyclopropyl CH.sub.3 H CHOCH.sub.3825 COOCH.sub.2 1-(2-Chlorophenyl)cyclopropyl CH.sub.3 H CHOCH.sub.3826 CH.sub.2 H C.sub.2 H.sub.5 H CHOCH.sub.3827 CHCl H C.sub.2 H.sub.5 H CHOCH.sub.3828 CHBr H C.sub.2 H.sub.5 H CHOCH.sub.3829 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 C.sub.6 H.sub.5 H CHOCH.sub.3830 CHCH C.sub.6 H.sub.5 C.sub.6 H.sub.5 H CHOCH.sub.3831 OCH.sub.2 C.sub.6 H.sub.5 C.sub.6 H.sub.5 H CHOCH.sub.3832 CH.sub.2 O C.sub.6 H.sub.5 C.sub.6 H.sub.5 H CHOCH.sub.3833 O C.sub.6 H.sub.5 C.sub.6 H.sub.5 H CHOCH.sub.3834 OCH.sub.2 C.sub.6 H.sub.5 OCH.sub.3 H CHOCH.sub.3835 CHCH C.sub.6 H.sub.5 OCH.sub.3 H CHOCH.sub.3836 CH.sub.2 H OCH.sub.3 H CHOCH.sub.3837 CHCl H OCH.sub.3 H CHOCH.sub.3838 CHBr H OCH.sub.3 H CHOCH.sub.3839 CH.sub.2 H OCH.sub.3 CH.sub.3 CHOCH.sub.3840 OCH.sub.2 C.sub.6 H.sub.5 OCH.sub.3 CH.sub.3 CHOCH.sub.3841 OCH.sub.2 C.sub.6 H.sub.5 OC.sub.2 H.sub.5 H CHOCH.sub.3842 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H H CHOMe843 CHCH C.sub.6 H.sub.5 H H CHOMe844 CH.sub.2 C.sub.6 H.sub.5 H H CHOMe845 OCH.sub.2 C.sub.6 H.sub.5 H H CHOMe846 O C.sub.6 H.sub.5 H H CHOMe847 CC C.sub.6 H.sub.5 H H CHOMe848 S C.sub.6 H.sub.5 H H CHOMe849 SCH.sub.2 C.sub.6 H.sub.5 H H CHOMe850 COO C.sub.6 H.sub.5 H H CHOMe851 OCO C.sub.6 H.sub.5 H H CHOMe852 COCH.sub.2 C.sub.6 H.sub.5 H H CHOMe853 CH.sub.2 CO C.sub.6 H.sub.5 H H CHOMe854 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe855 CHCH C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe856 CH.sub.2 O C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe857 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe858 O C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe859 CC C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe860 S C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe861 SCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe862 COO C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe863 OCO C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe864 COCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe865 CH.sub.2 CO C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHOMe866 OCH.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 CH.sub.3 CHOMe867 OCH.sub.2 C.sub.6 H.sub.5 C.sub.3 H.sub.7 CH.sub.3 CHOMe868 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H H CHSCH.sub.3869 CHCH C.sub.6 H.sub.5 H H CHSCH.sub.3870 CH.sub.2 O C.sub.6 H.sub.5 H H CHSCH.sub.3871 OCH.sub.2 C.sub.6 H.sub.5 H H CHSCH.sub.3872 O C.sub.6 H.sub.5 H H CHSCH.sub.3873 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHSCH.sub.3874 CHCH C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHSCH.sub.3875 CH.sub.2 O C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHSCH.sub.3876 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHSCH.sub.3877 O C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CHSCH.sub.3878 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3879 CHCH C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3880 CH.sub.2 O C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3881 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3882 O C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3883 COOCH.sub.2 1-Methylcyclopropyl CH.sub.3 H CHSCH.sub.3884 CC C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3885 S C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3886 SCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3887 COO C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3888 OCO C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3889 COCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3890 CH.sub.2 CO C.sub.6 H.sub.5 CH.sub.3 H CHSCH.sub.3891 OCH.sub.2 C.sub.6 H.sub.5 OCH.sub.3 H CHSCH.sub.3892 OCH.sub.2 C.sub.6 H.sub.5 OCH.sub.3 CH.sub.3 CHSCH.sub.3__________________________________________________________________________
EXAMPLES OF USE
The comparison substance was ##STR12## which is disclosed in EP-A 310 954 (compound No. 312; E/Z isomer mixture )
Example 5
Activity against Plasmopara viticola .
Leaves of potted vines of the Muller-Thurgau variety were sprayed with 0. 025% by weight aqueous suspensions containing 80% by weight active ingredient (Examples 87, 89, 93, 96,242, 252, 449, 494, 585 and 586 in the table) and 20% by weight emulsifier in dry matter. To assess the duration of action after the sprayed-on layer had dried, the plants were placed in a greenhouse for 8 days. The leaves were then infected with a suspension of Plasmopara viticola spores and the plants were placed in a chamber saturated with water vapor at 24.degree. C. for 48 hours. The vines were then grown in a greenhouse at from 20.degree. to 30.degree. C. for 5 days and, to accelerate sporangiophore for discharge, again placed in the humidity chamber for 16 hours. The extent of the fungus attack was then assessed on the undersides of the leaves.
Compared with a control test (no treatment, 60% fungus attack) and the known comparison compound A (35% fungus attack) it was found that the fungus attack was only from 0 to 5% on the plants treated with active ingredients 87, 89, 93, 96, 242, 252, 449, 494, 585 and 586.
Example 6
Activity against wheat mildew
Leaves of pot-grown wheat seedlings of the Fruhgold variety were sprayed with 0.025% by weight aqueous formulations which contained 80% by weight active ingredient (Examples 449 and 587 in the table) and 20% by weight emulsifier in dry matter, and, 24 hours after the sprayed-on layer had dried, dusted with spores of wheat mildew (Erysiphe graminis var. tritici). The test plants were then placed in a greenhouse at from 20.degree. to 22.degree. C. and 75 to 80% relative humidity. The extent of mildew development was assessed after 7 days.
Compared with a control test (no treatment, 70% fungus attack) and the known comparison compound A (35% fungus attack) it was found that plants treated with active ingredients 449 and 587 had no fungus attack.
Example 7
Activity against Pyricularia oryzae (preventive treatment)
Leaves of pot-grown rice seedlings of the Bahia variety were sprayed to run off with aqueous emulsions which contained 80% active ingredient and 20% emulsifier in dry matter and, 24 hours later, infected with an aqueous suspension of Pyricularia oryzae spores. The test plants were then placed in chambers at from 20.degree.0 to 24.degree. C. and 95 to 99% relative humidity. The extent of fungus attack was determined after 6 days.
The result shows that active ingredients 242, 252, 449, 585 and 588 when used as 0.05% by weight aqueous formulation have a much better fungicidal action (93%) than the known comparison substance A (20%).

Number	Name	Date
3799757	Dixon et al.	Mar 1974
4415743	Martin	Nov 1983
4829085	Wenderoth et al.	May 1989
4952720	Schuetz et al.	Aug 1990
5051447	Wenderoth et al.	Sep 1991
5183921	Takase et al.	Feb 1993
5185342	Hayase et al.	Feb 1993

Number	Date	Country
0088325	Sep 1983	EPX
0398692	Nov 1990	EPX
2808317	Sep 1978	DEX
0636601	Jun 1983	CHX

	Number	Date	Country
Parent	354734	Dec 1994
Parent	124437	Sep 1993

Ortho-substituted phenylacetamides

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