Derivatives of beta-picoline and crop protection agents containing them

The present invention relates to .beta.-picoline derivatives and fungicides containing them.
The compound 1-phenyl-3-(3-pyridinyl)-propan-1-one is disclosed in J. Org. Chem. 43 (1978), 3396 and in Arch. Pharm. 307 (1974), 550, but a fungicidal action is not reported.
We have found that .beta.-picoline derivatives of the formula ##STR2## where A is CR.sup.1 R.sup.2,
R.sup.1 and R.sup.2 independently of one another are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynylor R.sup.1 and R.sup.2 together form a methylene chain having from 2 to 6 methylene groups,
B is one of the groups CH.sub.2, CHOR.sup.3, CHR.sup.4, C.dbd.O or C.dbd.N-O-R.sup.5,
R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -acyl, phenyl, benzyl or benzoyl, where the phenyl ring may be unsubstituted or substituted by from one to three substituents from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, cyano and nitro,
R.sup.4 is hydrogen, fluorine, chlorine, bromine or iodine,
R.sup.5 is hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl or aralkyl where the alkyl radical is of 1 to 4 carbon atoms and the aryl radical may be unsubstituted or substituted by from one to three substituents from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, halogen, cyano and nitro, and Ar is a mononuclear or dinuclear aryl radical which is unsubstituted or monosubstituted to trisubstituted by halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, phenyl, phenoxy, halophenyl, halophenoxy or benzyloxy,
and their N-oxides and plant-tolerated acid addition salts, except for the compound in which A is CH.sub.2, B is C.dbd.O and Ar is phenyl, have a good fungicidal action, which is better than the action of known active ingredients.
R.sup.1 and R.sup.2 independently of one another are each, for example, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, allyl, 2-methylallyl, 3-methylallyl, 3,3-dimethylallyl or propargyl. The radicals CR.sup.1 R.sup.2 in which R.sup.1 is not hydrogen, in particular the radicals in which R.sup.1 and R.sup.2 are not hydrogen, are preferred.
R.sup.1 and R.sup.2 together may furthermore, together with the carbon atom of which they are substituents, form a cycloalkyl ring of 3 to 7 carbon atoms which contains from 2 to 6 methylene groups.
R.sup.3 is, for example, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, allyl, 2-methylallyl, 3-methylallyl, 3,3-dimethylallyl, propargyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, 2-bromoethyl, 2-chloroethyl, 3-bromopropyl, 4-bromobutyl, phenyl, mono-, di- or trimethylphenyl, 4-tert-butylphenyl, mono-, di- or trimethoxyphenyl, trifluoromethylphenyl, fluorophenyl, mono-, di- or trichlorophenyl, mono- or dinitrophenyl, cyanophenyl, mono-, di- or tribenzyl, 4-tert-butylphenyl, mono-, di- or trimethoxyb-enzyl, trifluoromethylbenzyl, fluorobenzyl, mono-, di- or trichlorobenzyl, mono- or dinitrobenzyl, cyanobenzyl, mono-, di- or trimethylbenzoyl, 4-tert-butylbenzoyl, mono-, di- or trimethoxybenzoyl, trifluoromethylbenzoyl, fluorobenzoyl, mono-, di- or trichlorobenzoyl, mono- or dinitrobenzoyl, cyanobenzoyl, acetyl, propionyl, butyryl, pentanoyl or hexanoyl
R.sup.5 is, for example, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, allyl, 2-methylallyl, 3-methylallyl, 3,3-dimethylally, propargyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, 2-bromcethyl, 2-chloroethyl, 3-bromopropyl, 4-bromobutyl, phenyl, mono-, di- or trimethylphenyl, 4-tert-butylphenyl, mono-, di- or trimethoxyphenyl, trifluoromethylphenyl, fluorophenyl, mono-, di- or trichlorophenyl, mono- or dinitrophenyl, cyanophenyl, mono-, di- or trimethylbenzyl, 4-tert-butylbenzyl, mono-, di- or trimethoxybenzyl, trifluoromethylbenzyl, fluorobenzyl, mono-, di- or trichlorobenzyl, mono- or dinitrobenzyl or cyanobenzyl and Ar is, for example, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 4-isopropyl-phenyl, 4-tert-butylphenyl, 1-naphthyl, 2-naphthyl, 4-biphenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,4,6-trichloropheny-1,2-chloro-4-fluoropheny1,2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-, 3- or 4-methoxyphenyl, 3,4-dimethoxyphenyl, 4-trifluoromethoxyphenyl, 4-tetrafluoroethoxyphenyl- 2-chloro-1,4-phenoxypheny1,4-(4,-chlorophenoxy)-phenyl or 4 -benzyloxyphenyl.
The compounds of the formula I may have two or more centers of asymmetry and can therefore occur in two or more diastereomeric forms, which can be separated by known methods, for example by chromatography or crystallization. The present invention relates both to the pure diastereomers and to mixtures thereof and to their use as fungicides.
The .beta.-picoline derivatives can be prepared by a method in which an aldehyde of the formula II ##STR3## where A has the abovementioned meanings, is reacted with an organometallic compound of the formula III
Ar-M (III)
where M is lithium or one of the radicals MgCl, MgBr or MgI and Ar has the abovementioned meanings. It is advantageous initially to take the organometallic compound of the formula III in an inert solvent, preferably an ether, such as diethyl ether or tetrahydrofuran, at from 0 to 80.degree. C., preferably from 0 to 20.degree. C., and to add the aldehyde of the formula II, if necessary dissolved in a diluent.
The organometallic compounds of the formula III are generally known. The aldehydes of the formula II where A is CH.sub.2 or CH(CH.sub.3) are disclosed in J. Org. Chem. 43 (1978), 3396 and 2947. The other aldehydes of the formula II where A has the abovementioned meanings are novel. They can be prepared, for example, by alkylating an aldehyde of the formula IV
H--A--CHO (IV)
where A has the abovementioned meanings with the exception of CH.sub.2 and CH(CH.sub.3), with 3-chloromethylpyridine produced in situ, in the presence of a base. 3-Chloromethylpyridine is unstable and tends to form a resin at as low as room temperature (cf. for example CA 47, 8068e). A 3-chloromethylpyridine liberated in situ from the hydrochloride is a suitable reagent for the alkylation of aldehydes.
The direct alpha-alkylation of aldehydes takes place, as a rule, with only poor yields, and the same applies to the enamines derived from the aldehydes (cf. for example G. Opitz et al., Liebigs Ann. Chem. 649 (1961), 36). A simple preparative method is the alphaalkylation of aldehydes under phase transfer catalysis. This process can be carried out as a solid/liquid variant in a two-phase system consisting of solid sodium hydroxide and a lipophilic organic solvent (cf. H. K. Dietl and K. C. Brannock, Tetrahedron Lett. 1273 (1973); E. Buschmann and B. Zeeh, Liebigs Ann. Chem. 1585 (1979)). Particularly advantageous here is a liquid/liquid variant in which the sodium hydroxide solution and an organic, water immiscible solvent and a suitable phase transfer catalyst are initially taken and the aldehyde IV, if necessary dissolved in a diluent, and the 3-chloromethylpyridine hydrochloride, if necessary in the form of an aqueous solution, are metered in. Examples of suitable organic phases are hydrocarbons, such as petroleum ether, cyclohexane, benzene, toluene, xylene or chlorohydrocarbons, such as dichloromethane or 1,2-dichloroethane. For example, crown ethers or quaternary ammonium salts, preferably tetra-n-butylammonium salts, benzyltriethylammonium salts or methyltrioctylammonium salts, can be used as phase transfer catalysts. The reaction is preferably carried out at from 0 to 100.degree. C., in particular from 20 to 80.degree. C. In another process for the preparation of aldehydes of the formula II, an .alpha.,.beta.-unsaturated aldehyde of the formula ##STR4## where A is C-(C.sub.1 -C.sub.6 -alkyl), is hydrogenated with hydrogen in the presence of a suitable catalyst. The aldehydes of the formula V are novel. They can be prepared by a method in which the aldehyde ##STR5## is reacted with an aldehyde ##STR6## (similarly to European Patent 298, 380).
The processes for carrying out the oxidation of the alcohols of the general formula I (B.dbd.CHOH) are known from the literature (cf. for example Houben-Weyl, Methoden der organischen Chemie, Volume VII/2a, Ketone Part 1, page 699 et seq.). A preferred process is the oxidation with dimethyl sulfoxide in the presence of suitable reagents, for example oxalyl chloride/triethylamine. Suitable diluents are inert organic solvents, for example hydrocarbons, such as petroleum ether, cyclohexane, benzene or chlorohydrocarbons, such as dichloromethane, 1,2-dichloroethane or chloroform, or ethers, eg. diethyl ether, tetrahydrofuran or dioxane. The reaction is carried out at from -80 to 50.degree. C., preferably from -70 to -10.degree. C.
The chlorides of the general formula I where B is H--C--Cl are obtainable from the corresponding hydroxy compounds by methods known from the literature (cf. for example Houben-Weyl, Methoden der organischen Chemie, Volume V/3, Halogenverbindungen).
The reaction of thionyl chloride with the alcohols is a preferably used process. Suitable diluents are inert solvents, for example hydrocarbons, such as petroleum ether, cyclohexane, benzene, toluene or xylene. The reaction is carried out at from 40 to 150.degree. C., preferably 80.degree. C., in the presence or absence of a catalyst. Examples of suitable catalysts are dimethylformamide and tertiary amines, such as triethylamine, N,N-dimethylaniline or piperidine.
The oxime ethers of the general formula I where B is C.dbd.R.sup.5 and R.sup.5 has the meanings stated in the claim are obtainable by conventional processes (cf. Houben-Weyl, Methoden der organischen Chemie, X, 4/55).
A preferably used process is the reaction of the ketones of the general formula I where B is C.dbd.O and a hydroxylamine in a suitable diluent and suitable reagents. Suitable diluents are inert organic solvents, for example hydrocarbons, such as petroleum ether, cyclohexane or benzene, or chlorohydrocarbons, such as dichloromethane, 1,2-dichloroethane or chloroform, ethers, eg. diethyl ether, tetrahydrofuran or dioxane, nitriles, such as acetonitrile or propionitrile, and alcohols, such as methanol, ethanol or n-butanol.
Suitable reaction assistants are all conventional inorganic and organic bases, for example alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, alkali metal alcoholates, such as sodium methylate, sodium ethylate or potassium tert-butylate, alkali metal carbonates, such as sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate, and tertiary amines, such as triethylamine, N,N-dimethylaniline or piperidine.
The reaction is carried out at from 20 to 150.degree. C., preferably from 50 to 130.degree. C.
The N-oxides can be prepared by oxidizing the .beta.-picoline derivatives of the formula I.
Plant-tolerated acid addition salts are salts of the .beta.-picoline derivatives of the formula I with inorganic or organic acids, for example sulfuric acid, phosphoric acid, acetic acid, propionic acid, oxalic acid, phenylsulfonic acid or dodecylbenzenesulfonic acid.
The methods and Examples which follow illustrate the preparation of the intermediates and of the novel compounds.
Method 1
2-(Pyrid-3-ylmethyl)-hexanol
A mixture of 21 g (0.11 mol) of 2-butyl-3-pyridylpropenal, 120 ml of methanol, 10 g of N-methylmorpholine and 6 g of a hydrogenation catalyst (10% of Pd and 5% of Pr.sub.2 O.sub.3 on Al.sub.2 O.sub.3) is hydrogenated at 75.degree. C. and 75 bar hydrogen pressure in a 0.3 1 stirred autoclave until the pressure remains constant. The solution is filtered under suction over silica gel, the filtrate is evaporated down under reduced pressure and the residue is purified by distillation.
Yield: 24.1 g (56.8%) ##STR7##
Method 2
2-(Pyrid-3-ylmethyl)-hexanal
23 g (0.132 mol) of dimethy sulfoxide in 120 ml of CH.sub.2 Cl.sub.2 are added dropwise in the course of one hour to 17 g (0.132 mol) of oxalyl chloride in 280 ml of CH.sub.2 Cl.sub.2 at -60.degree. C. Thereafter, 23 g (0.12 mol) of 2-(pyrid-3-yl-methyl)-hexanol in 240 ml of CH.sub.2 Cl.sub.2 are slowly added, followed by 62 g of triethylamine after 30 minutes.
The mixture is allowed to reach room temperature (RT, 20.degree. C.) slowly and 350 ml of H.sub.2 O are added. The aqueous phase is extracted with 3.times.300 ml of CH.sub.2 Cl.sub.2 and the combined methylene chloride phases are washed with NaHCO.sub.3 solution. Drying is carried out over Na.sub.2 SO.sub.4, the solvent is evaporated off and the residue is then subjected to distillation. 8.2 g (36%) of the title compound (118-120.degree. C., 0.7 mmHg) are obtained. ##STR8##
Method 3
2-Ethyl-2-(pyrid-3-ylmethyl)-butanal
A solution of 98.4 g (0.6 mol) of .beta.-picoline chloride hydrochloride and 66 g (0.66 mol) of 2-ethylbutanal in 600 ml of toluene is added dropwise in the course of 3 hours to a mixture of 450 ml of toluene, 600 ml of 30% strength by weight NaOH (4.5 mol) and 7.5 g of tetrabutylammonium iodide at 80.degree. C.
Stirring is then carried out for a further 3 hours at this temperature, the mixture is cooled and 1,000 ml of toluene are then added. The organic phase is separated off, washed three times with water, dried and evaporated down.
Distillation (128-132.degree. C./2 mmHg) gives 56 g (49%) of the title compound.

EXAMPLE 1
2-Ethyl-1-(4-fluorophenyl)-2-(pyrid-3-ylmethyl)-butan-1-ol
20.4 g (0.116 mol) of 4-fluorobromobenzene in 250 ml of tetrahydrofuran are added dropwise to 2.8 g of magnesium turnings (0.166 mol) and stirring is carried out for half an hour at RT. 11 g (0.058 mol) of 2-ethyl-2-(pyrid-3-ylmethyl)-butanal in 100 ml of tetrahydrofuran are then slowly added dropwise. After 2 hours, the mixture is poured onto ice water and brought to pH 8 with saturated NH.sub.4 Cl solution. It is extracted with ether, the organic phase is washed with water and dried over Na.sub.2 SO.sub.4 and the solvent is then evaporated off. 8 g (48%) of the title compound are obtained as a viscous oil (compound No. 70 in the Table).
EXAMPLE 2
2Ethyl-1-(4-fluorophenyl)-2-(pyrid-30-0ylmethyl)-butan-1-one
22.5 g (0.288 mol) of dimethyl sulfoxide in 50 ml of methylene chloride are added dropwise to 18.6 g (0.144 mol) of oxalyl chloride in 200 ml of CH.sub.2 Cl.sub.2 at -60.degree. C. The reaction is allowed to continue for 5 minutes at -60.degree. C.
33 g (0.115 mol) of 2-ethyl-1-(4-fluorophenyl)-2-(pyrid-3-ylmethyl)-butanol in 100 ml of CH.sub.2 Cl.sub.2 are then slowly added and, after 15 minutes, 58.2 g (0.576 mol) of triethylamine are introduced. The mixture is allowed to reach RT slowly, 350 ml of water are added, the aqueous phase is extracted with 3.times.200 ml of CH.sub.2 Cl.sub.2 and the combined organic phases are dried over Na.sub.2 SO.sub.4. After the solvent has been evaporated off, the title compound is obtained in a yield of 49% (compound No. 331).
EXAMPLE 3
1-Chloro-2-ethyl-1-phenyl-2-(pyrid-3-ylmethyl)-butane
13.3 g (0.11 mol) of SOCl.sub.2 are added dropwise, at 80.degree. C., to 5 g (0.018 mol) of 2-ethyl-1-phenyl-2-(pyrid-3-ylmethyl)-butanol in 100 ml of toluene and a catalytic amount (0.1 g) of dimethylformamide, and the mixture is left for 5 hours at this temperature. The mixture is cooled, poured onto ice water and then rendered alkaline with 30% strength NaOH solution. The aqueous phase is extracted with three times 50 ml of tert-butyl methyl ether and the combined organic phases are dried over MgSO.sub.4. After the solvent has been evaporated off, the residue is chromatographed over silica gel (1 : 1 toluene/ethyl acetate). 2.07 g (yield 40%) of the title compound are obtained as a viscous yellow oil (compound No. 581).
The compounds listed in the Table below can be prepared in a similar manner.
TABLE__________________________________________________________________________No. A B Ar Phys. data IR, cm.sup.-1__________________________________________________________________________ 1 C(CH.sub.3).sub.2 CHOH Phenyl oil 2963, 1449, 1424, 1361, 1059, 1045 2 C(CH.sub.3).sub.2 CHOH 2-Methylphenyl 107-110.degree. C. 3 C(CH.sub.3).sub.2 CHOH 4-Methylphenyl oil 3146, 1474, 1426, 1069, 1045, 824 4 C(CH.sub.3).sub.2 CHOH 2,4-Dimethylphenyl 5 C(CH.sub.3).sub.2 CHOH 2,6-Diemthylphenyl 6 C(CH.sub.3).sub.2 CHOH 2,4,6-Trimethylphenyl 155-157.degree. C. 7 C(CH.sub.3).sub.2 CHOH 4-tert. Butylphenyl 144-146.degree. C. 8 C(CH.sub.3).sub.2 CHOH 1-Naphtyl 9 C(CH.sub.3).sub.2 CHOH 2-Napthyl 10 C(CH.sub.3).sub.2 CHOH 4-Biphenyl 11 C(CH.sub.3).sub.2 CHOH 2-Fluorophenyl 12 C(CH.sub.3).sub.2 CHOH 4-Fluorophenyl oil 3200, 2966, 2871, 1602, 1508, 1424 13 C(CH.sub.3).sub.2 CHOH 2,4-Difluorophenyl 14 C(CH.sub.3).sub.2 CHOH 2-Chlorophenyl 15 C(CH.sub.3).sub.2 CHOH 3-Chlorophenyl 16 C(CH.sub.3).sub.2 CHOH 4-Chlorophenyl oil 3200, 2966, 2934, 2870, 1486, 1424 17 C(CH.sub.3).sub.2 CHOH 2,4-Dichlorophenyl oil 3300, 2967, 1587, 1467, 717 18 C(CH.sub.3).sub.2 CHOH 3,4-Dichlorophenyl 19 C(CH.sub.3).sub.2 CHOH 2-Chloro-4-fluorophenyl 20 C(CH.sub.3).sub.2 CHOH 2-Trifluoromethylphenyl 21 C(CH.sub.3).sub.2 CHOH 4-Trifluoromethylphenyl 22 C(CH.sub.3).sub.2 CHOH 4-Methoxyphenyl oil 3250, 2961, 1610, 1511, 1247 23 C(CH.sub.3).sub.2 CHOH 3,4-Dimethoxyphenyl 24 C(CH.sub.3).sub.2 CHOH 4-Tetrafluoroethoxyphenyl 25 C(CH.sub.3).sub.2 CHOH 4-Trifluoromethoxyphenyl 26 C(CH.sub.3).sub.2 CHOH 2-Chloro-4-(4'-chlorophenoxy)phenyl 27 C(CH.sub.3).sub.2 CHOH 4-Phenoxyphenyl 28 C(CH.sub.3).sub.2 CHOH 4-(4'-Chlorophenoxy)phenyl 29 C(CH.sub.3).sub.2 CHOH 4-Benzyloxyphenyl 30 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH Phenyl oil 3200, 2964, 2936, 2877, 1463, 1452 31 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2-Methylphenyl 32 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-Methylphenyl oil 3200, 2964, 2936, 2877, 1478, 1463, 1424 33 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2,4-Dimethylphenyl 34 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2,6-Dimethylphenyl 35 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2,4,6-Trimethylphenyl 36 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-tert. Butylphenyl 37 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 1-Naphthyl 38 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2-Naphthyl 39 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-Biphenyl 40 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2-Fluorophenyl 41 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-Fluorophenyl oil 3200, 2965, 2937, 1602, 1508, 1424 42 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2,4-Difluorophenyl 43 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2-Chlorophenyl 44 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 3-Chlorophenyl 45 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-Chlorophenyl oil 3190, 2965, 2936, 2877, 1486, 1464 46 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2,4-Dichlorophenyl 47 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 3,4-Dichlorophenyl 48 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2-Chloro-4-fluorophenyl 49 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2-Trifluoromethylphenyl 50 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-Trifluoromethylphenyl 51 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-Methoxyphenyl 52 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 3,4-Dimethoxyphenyl 53 C(CH.sub.3)(CH.sub.2 CH.sub. 3) CHOH 4-Tetrafluoroethoxyphenyl 54 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-Trifluoromethoxyphenyl 55 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 2-Chloro-4-(4'-chlorophenoxy)phenyl 56 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-Phenoxyphenyl 57 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-(4'-Chlorophenoxy)phenyl 58 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHOH 4-Benzyloxyphenyl 59 C(CH.sub.2 CH.sub.3).sub.2 CHOH Phenyl oil 3203, 2963, 2935, 2879, 1452, 1424 60 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2-Methylphenyl oil 3320, 2963, 1425, 1030, 758, 718 61 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Methylphenyl oil 2965, 2936, 2879, 1478, 1455, 1424 62 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2,4-Dimethylphenyl 63 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2,6-Dimethylphenyl 64 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2,4,6-Trimethylphenyl 161-164.degree. C. 65 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-tert. Butylphenyl 66 C(CH.sub.2 CH.sub.3).sub.2 CHOH 1-Naphthyl 67 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2-Naphthyl 68 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Biphenyl 69 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2-Fluorophenyl 70 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Fluorophenyl oil 3200, 2966, 2937, 2879, 1602, 1507 71 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2,4-Difluorophenyl 72 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2-Chlorophenyl 73 C(CH.sub.2 CH.sub.3).sub.2 CHOH 3-Chlorophenyl 74 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Chlorophenyl oil 3200, 2966, 2937, 2878, 1487, 1424 75 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2,4-Dichlorophenyl mp. 142-144.degree. C. 76 C(CH.sub.2 CH.sub.3).sub.2 CHOH 3,4-Dichlorophenyl 77 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2-Chloro-4-fluorophenyl 78 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2-Trifluoromethylphenyl 79 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Trifluoromethylphenyl 80 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Methoxyphenyl oil 3200, 2963, 1510, 1246, 1031, 717 81 C(CH.sub.2 CH.sub.3).sub.2 CHOH 3,4-Dimethoxyphenyl 82 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Tetrafluoroethoxyphenyl 83 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Trifluoromethoxyphenyl 84 C(CH.sub.2 CH.sub.3).sub.2 CHOH 2-Chloro-4-(4'-chlorophenoxy)phenyl 85 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Phenoxyphenyl 86 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-(4'-Chlorophenoxy)phenyl 87 C(CH.sub.2 CH.sub.3).sub.2 CHOH 4-Benzyloxyphenyl 88 Cyclopropylene CHOH Phenyl oil 3231, 3027, 1424, 1028, 715, 702 89 Cyclopropylene CHOH 2-Methylphenyl 90 Cyclopropylene CHOH 4-Methylphenyl oil 3238, 2921, 1424, 1044, 820, 716 91 Cyclopropylene CHOH 2,4-Dimethylphenyl 92 Cyclopropylene CHOH 2,6-Dimethylphenyl 93 Cyclopropylene CHOH 2,4,6-Trimethylphenyl 94 Cyclopropylene CHOH 4-tert. Butylphenyl 95 Cyclopropylene CHOH 1-Naphthyl 96 Cyclopropylene CHOH 2-Naphthyl 97 Cyclopropylene CHOH 4-Biphenyl 98 Cyclopropylene CHOH 4-Fluorophenyl 99 Cyclopropylene CHOH 4-Fluorophenyl oil 3200, 2940, 1508, 1221, 838100 Cyclopropylene CHOH 2,4-Difluorophenyl101 Cyclopropylene CHOH 2-Chlorophenyl102 Cyclopropylene CHOH 3-Chlorophenyl103 Cyclopropylene CHOH 4-Chlorophenyl oil 3200, 2924, 1425, 1014, 717104 Cyclopropylene CHOH 2,4-Dichlorophenyl105 Cyclopropylene CHOH 3,4-Dichlorophenyl106 Cyclopropylene CHOH 2-Chloro-4-fluorophenyl107 Cyclopropylene CHOH 2-Trifluoromethylphenyl108 Cyclopropylene CHOH 4-Trifluoromethylphenyl109 Cyclopropylene CHOH 4-Methoxyphenyl110 Cyclopropylene CHOH 3,4-Dimethoxyphenyl111 Cyclopropylene CHOH 4-Tetrafluoroethoxyphenyl112 Cyclopropylene CHOH 4-Trifluoromethoxyphenyl113 Cyclopropylene CHOH 2-Chloro-4-(4'-chlorophenoxy)phenyl114 Cyclopropylene CHOH 4-Phenoxyphenyl115 Cyclopropylene CHOH 4-(4'-Chlorophenoxy)phenyl116 Cyclopropylene CHOH 4-Benzyloxyphenyl117 Cyclopentylene CHOH Phenyl oil 3211, 2953, 2869, 1478, 1451, 1424118 Cyclopentylene CHOH 2-Methylphenyl oil 3225, 2954, 1442, 1031, 740, 719119 Cyclopentylene CHOH 4-Methylphenyl oil 3225, 2952, 2869, 1478, 1451, 1424120 Cyclopentylene CHOH 2,4-Dimethylphenyl121 Cyclopentylene CHOH 2,6-Dimethylphenyl122 Cyclopentylene CHOH 2,4,6-Trimethylphenyl 141-142.degree. C.123 Cyclopentylene CHOH 4-tert. Butylphenyl124 Cyclopentylene CHOH 1-Naphthyl125 cyclopentylene CHOH 2-Naphthyl126 Cyclopentylene CHOH 4-Biphenyl127 Cyclopentylene CHOH 2-Fluorophenyl128 Cyclopentylene CHOH 4-Fluorophenyl oil 3200, 2954, 2871, 1603, 1507, 1425129 Cyclopentylene CHOH 2,4-Difluorophenyl130 Cyclopentylene CHOH 2-Chlorophenyl131 Cyclopentylene CHOH 3-Chlorophenyl132 Cyclopentylene CHOH 4-Chlorophenyl oil 2954, 2870, 1484, 1090, 1046, 1030133 Cyclopentylene CHOH 2,4-Dichlorophenyl mp. 150-151.degree. C. 3270, 2952, 2872, 2706, 2625, 1541134 Cyclopentylene CHOH 3,4-Dichlorophenyl135 Cyclopentylene CHOH 2-Chloro-4-fluorophenyl136 Cyclopentylene CHOH 2-Trifluoromethylphenyl137 Cyclopentylene CHOH 4-Trifluoromethylphenyl138 Cyclopentylene CHOH 4-Methoxyphenyl 91-93.degree. C.139 Cyclopentylene CHOH 3,4-Dimethoxyphenyl140 Cyclopentylene CHOH 4-Tetrafluoroethoxyphenyl141 Cyclopentylene CHOH 4-Trifluoromethoxyphenyl142 Cyclopentylene CHOH 2-Chloro-4-(4'-chlorophenoxy)phenyl143 Cyclopentylene CHOH 4-Phenoxyphenyl144 Cyclopentylene CHOH 4-(4'-Chlorophenoxy)phenyl145 Cyclopentylene CHOH 4-Benzyloxyphenyl146 Cyclohexylene CHOH Phenyl oil 2933, 2860, 1454, 1424, 1067, 1042147 Cyclohexylene CHOH 2-Methylphenyl oil 3200, 2934, 1458, 1069, 737, 719148 Cyclohexylene CHOH 4-Methylphenyl oil 2933, 2860, 1456, 1423, 1069, 1042149 Cyclohexylene CHOH 2,4-Dimethylphenyl150 Cyclohexylene CHOH 2,6-Dimethylphenyl151 Cyclohexylene CHOH 2,4,6-Trimethylphenyl 164.degree. C.152 Cyclohexylene CHOH 4-tert. Butylphenyl 167-169.degree. C.153 Cyclohexylene CHOH 1-Naphthyl154 Cyclohexylene CHOH 2-Naphthyl155 Cyclohexylene CHOH 4-Biphenyl156 Cyclohexylene CHOH 2-Fluorophenyl157 Cyclohexylene CHOH 4-Fluorophenyl mp. 133-135.degree. C. 3264, 2928, 2862, 1507, 1453, 1428, 1222158 Cyclohexylene CHOH 2,4-Difluorophenyl159 Cyclohexylene CHOH 2-Chlorophenyl160 Cyclohexylene CHOH 3-Chlorophenyl161 Cyclohexylene CHOH 4-Chlorophenyl oil 3152, 2931, 1480, 1427, 1076, 717162 Cyclohexylene CHOH 2,4-Dichlorophenyl 140-141.degree. C.163 Cyclohexylene CHOH 3,4-Dichlorophenyl164 Cyclohexylene CHOH 2-Chloro-4-fluorophenyl165 Cyclohexylene CHOH 2-Trifluoromethylphenyl166 Cyclohexylene CHOH 4-Trifluoromethylphenyl167 Cyclohexylene CHOH 4-Methoxyphenyl 126-129.degree. C.168 Cyclohexylene CHOH 3,4-Dimethoxyphenyl169 Cyclohexylene CHOH 4-Tetrafluoroethoxyphenyl170 Cyclohexylene CHOH 4-Trifluoromethoxyphenyl171 Cyclohexylene CHOH 2-Chloro-4-(4'-chlorophenoxy)phenyl172 Cyclohexylene CHOH 4-Phenoxyphenyl173 Cyclohexylene CHOH 4-(4'-Chlorophenoxy)phenyl174 Cyclohexylene CHOH 4-Benzyloxyphenyl175 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH Phenyl oil 2958, 2933, 2871, 1452, 1424, 1068176 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2-Methylphenyl177 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-Methylphenyl oil 2958, 2933, 2870, 1467, 1456, 1424178 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2,4-Dimethylphenyl179 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2,6-Dimethylphenyl180 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2,4,6-Trimethylphenyl181 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-tert. Butylphenyl182 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 1-Naphthyl183 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2-Naphthyl184 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-Biphenyl185 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2-Fluorophenyl186 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-Fluorophenyl oil 2959, 2934, 2871, 1508, 1425, 1223187 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2,4-Difluorophenyl188 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2-Chlorophenyl189 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 3-Chlorophenyl190 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-Chlorophenyl oil 2958, 2933, 2871, 1486, 1424, 1090191 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2,4-Dichlorophenyl192 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 3,4-Dichlorophenyl193 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2-Chloro-4-fluorophenyl194 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2-Trifluoromethylphenyl195 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-Trifluoromethylphenyl196 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-Methoxyphenyl197 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 3,4-Dimethoxyphenyl198 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-Tetrafluoroethoxyphenyl199 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-Trifluoromethoxyphenyl200 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 2-Chloro-4-(4'-chlorophenoxy)phenyl201 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-Phenoxyphenyl202 C(CH.sub.3)(C.sub.3 H.sub.7) CHOH 4-(4'-Chlorophenoxy)phenyl203 C(CH.sub.3)(C.sub. 3 H.sub.7) CHOH 4-Benzyloxyphenyl204 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH Phenyl oil 3196, 2956, 2934, 2869, 1452, 1424205 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2-Methylphenyl206 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Methylphenyl oil 3200, 2956, 2933, 2870, 1478, 1457207 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2,4-Dimethylphenyl208 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2,6-Dimethylphenyl209 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2,4,6-Trimethylphenyl210 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-tert. Butylphenyl211 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 1-Naphthyl212 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2-Naphthyl213 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Biphenyl214 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2-Fluorophenyl215 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Fluorophenyl oil 3198, 2957, 2935, 2870, 1603, 1507216 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2,4-Difluorophenyl217 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2-Chlorophenyl218 C(C.sub.2 H.sub. 5)(n-C.sub.4 H.sub.9) CHOH 3-Chlorophenyl219 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Chlorophenyl oil 2957, 2934, 2870, 1487, 1458, 1424220 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2,4-Dichlorophenyl221 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 3,4-Dichlorophenyl222 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2-Chloro-4-fluorophenyl223 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2-Trifluoromethylphenyl224 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Trifluoromethylphenyl225 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Methoxyphenyl226 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 3,4-Dimethoxyphenyl227 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Tetrafluoroethoxyphenyl228 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Trifluoromethoxyphenyl229 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 2-Chloro-4-(4'-chlorophenoxy)-phenyl230 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Phenoxyphenyl231 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-(4'-Chlorophenoxy)phenyl232 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHOH 4-Benzyloxyphenyl233 CH(tert.C.sub.4 H.sub.9) CHOH Phenyl234 CH(tert.C.sub.4 H.sub.9) CHOH 2-Methylphenyl235 CH(tert.C.sub.4 H.sub.9) CHOH 4-Methylphenyl236 CH(tert.C.sub.4 H.sub.9) CHOH 2,4-Dimethylphenyl237 CH(tert.C.sub.4 H.sub.9) CHOH 2,6-Dimethylphenyl238 CH(tert.C.sub.4 H.sub.9) CHOH 2,4,6-Trimethylphenyl239 CH(tert.C.sub.4 H.sub.9) CHOH 4-tert. Butylphenyl240 CH(tert.C.sub.4 H.sub.9) CHOH 1-Naphthyl241 CH(tert.C.sub.4 H.sub.9) CHOH 2-Naphthyl242 CH(tert.C.sub.4 H.sub.9) CHOH 4-Biphenyl243 CH(tert.C.sub.4 H.sub.9) CHOH 2-Fluorophenyl244 CH(tert.C.sub.4 H.sub.9) CHOH 4-Fluorophenyl oil 2.90, 2.75 (dd, 2H, --CH.sub.2 -Py)245 CH(tert.C.sub.4 H.sub.9) CHOH 2,4-Difluorophenyl246 CH(tert.C.sub.4 H.sub.9) CHOH 2-Chlorophenyl247 CH(tert.C.sub.4 H.sub.9) CHOH 3-Chlorophenyl248 CH(tert.C.sub.4 H.sub.9) CHOH 4-Chlorophenyl249 CH(tert.C.sub.4 H.sub.9) CHOH 2,4-Dichlorophenyl250 CH(tert.C.sub.4 H.sub.9) CHOH 3,4-Dichlorophenyl251 CH(tert.C.sub.4 H.sub.9) CHOH 2-Chloro-4-fluorophenyl252 CH(tert.C.sub.4 H.sub.9) CHOH 2-Trifluoromethylphenyl253 CH(tert.C.sub.4 H.sub.9) CHOH 4-Trifluoromethylphenyl254 CH(tert.C.sub.4 H.sub.9) CHOH 4-Methoxyphenyl255 CH(tert.C.sub.4 H.sub.9) CHOH 3,4-Dimethoxyphenyl256 CH(tert.C.sub.4 H.sub.9) CHOH 4-Tetrafluoroethoxyphenyl257 CH(tert.C.sub.4 H.sub.9) CHOH 4-Trifluoromethoxyphenyl258 CH(tert.C.sub.4 H.sub.9 ) CHOH 2-Chloro-4-(4'-chlorophenoxy)phenyl259 CH(tert.C.sub.4 H.sub.9) CHOH 4-Phenoxyphenyl260 CH(tert.C.sub.4 H.sub.9) CHOH 4-(4'-Chlorophenoxy)phenyl261 CH(tert.C.sub.4 H.sub.9) CHOH 4-Benzyloxyphenyl262 C(CH.sub.3).sub.2 C.dbd.O Phenyl263 C(CH.sub.3).sub.2 C.dbd.O 2-Methylphenyl264 C(CH.sub.3).sub.2 C.dbd.O 4-Methylphenyl oil 3.05 (s, 2H, --CH.sub.2 -Py)265 C(CH.sub.3).sub.2 C.dbd.O 2,4-Dimethylphenyl266 C(CH.sub.3).sub.2 C.dbd.O 2,6-Dimethylphenyl267 C(CH.sub.3).sub.2 C.dbd.O 2,4,6-Trimethylphenyl268 C(CH.sub.3).sub.2 C.dbd.O 4-tert. Butylphenyl269 C(CH.sub.3).sub.2 C.dbd.O 1-Naphthyl270 C(CH.sub.3).sub.2 C.dbd.O 2-Naphthyl271 C(CH.sub.3).sub.2 C.dbd.O 4-Biphenyl272 C(CH.sub.3).sub.2 C.dbd.O 2-Fluorophenyl273 C(CH.sub.3).sub.2 C.dbd.O 4-Fluorophenyl oil 2932, 1670, 1588, 1479, 1453, 1423274 C(CH.sub.3).sub.2 C.dbd.O 2,4-Difluorophenyl275 C(CH.sub.3).sub.2 C.dbd.O 2-Chlorophenyl276 C(CH.sub.3).sub.2 C.dbd.O 3-Chlorophenyl277 C(CH.sub.3).sub.2 C.dbd.O 4-Chlorophenyl oil 3.05 (s, 2H, --CH.sub.2 -Py)278 C(CH.sub.3).sub.2 C.dbd.O 2,4-Dichlorophenyl279 C(CH.sub.3).sub.2 C.dbd.O 3,4-Dichlorophenyl280 C(CH.sub.3 ).sub.2 C.dbd.O 2-Chloro-4-fluorophenyl281 C(CH.sub.3).sub.2 C.dbd.O 2-Trifluoromethylphenyl282 C(CH.sub.3).sub.2 C.dbd.O 4-Trifluoromethylphenyl283 C(CH.sub.3).sub.2 C.dbd.O 4-Methoxyphenyl284 C(CH.sub.3).sub.2 C.dbd.O 3,4-Dimethoxyphenyl285 C(CH.sub.3).sub.2 C.dbd.O 4-Tetrafluoroethoxyphenyl286 C(CH.sub.3).sub.2 C.dbd.O 4-Trifluoromethoxyphenyl287 C(CH.sub.3).sub.2 C.dbd.O 2-Chloro-4-(4'-chlorophenoxy)phenyl288 C(CH.sub.3).sub.2 C.dbd.O 4-Phenoxyphenyl289 C(CH.sub.3).sub.2 C.dbd.O 4-(4'-Chlorophenoxy)phenyl290 C(CH.sub.3).sub.2 C.dbd.O 4-Benzyloxyphenyl291 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O Phenyl292 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2-Methylphenyl293 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Methylphenyl294 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2,4-Dimethylphenyl295 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2,6-Dimethylphenyl296 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2,4,6-Trimethylphenyl297 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-tert. Butylphenyl298 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 1-Naphthyl299 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2-Naphthyl300 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Biphenyl301 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2-Fluorophenyl302 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Fluorophenyl303 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2,4-Difluorophenyl304 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2-Chlorophenyl305 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 3-Chlorophenyl306 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Chlorophenyl307 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2,4-Dichlorophenyl308 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 3,4-Dichlorophenyl309 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2-Chloro-4-fluorophenyl310 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2-Trifluoromethylphenyl311 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Trifluoromethylphenyl312 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Methoxyphenyl313 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 3,4-Dimethoxyphenyl314 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Tetrafluoroethoxyphenyl315 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Trifluoromethoxyphenyl316 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 2-Chloro-4-(4'-chlorophenoxy)phenyl317 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Phenoxyphenyl318 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-(4'-Chlorophenoxy)phenyl319 C(CH.sub.3)(CH.sub.2 CH.sub.3) C.dbd.O 4-Benzyloxyphenyl320 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O Phenyl321 C(CH.sub.2 CH.sub.3).sub.2 C.dbd. O 2-Methylphenyl322 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Methylphenyl323 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2,4-Dimethylphenyl324 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2,6-Dimethylphenyl325 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2,4,6-Trimethylphenyl326 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-tert. Butylphenyl327 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 1-Naphthyl328 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2-Naphthyl329 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Biphenyl330 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2-Fluorophenyl331 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Fluorophenyl oil 3.08 (s, 2H, --CH.sub.2 -Py)332 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2,4-Difluorophenyl333 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2-Chlorophenyl334 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 3-Chlorophenyl335 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Chlorophenyl336 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2,4-Dichlorophenyl337 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 3,4-Dichlorophenyl338 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2-Chloro-4-fluorophenyl339 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2-Trifluoromethylphenyl340 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Trifluoromethylphenyl341 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Methoxyphenyl342 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 3,4-Dimethoxyphenyl343 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Tetrafluoroethoxyphenyl344 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Trifluoromethoxyphenyl345 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 2-Chloro-4-(4'-chlorophenoxy)phenyl346 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Phenoxyphenyl347 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-(4'-Chlorophenoxy)phenyl348 C(CH.sub.2 CH.sub.3).sub.2 C.dbd.O 4-Benzyloxyphenyl349 Cyclopropylene C.dbd.O Phenyl350 Cyclopropylene C.dbd.O 2-Methylphenyl351 Cyclopropylene C.dbd.O 4-Methylphenyl oil 1671, 1808, 1423, 1177, 831, 715352 Cyclopropylene C.dbd.O 2,4-Dimethylphenyl353 Cyclopropylene C.dbd.O 2,6-Dimethylphenyl354 Cyclopropylene C.dbd.O 2,4,6-Trimethylphenyl355 Cyclopropylene C.dbd.O 4-tert. Butylphenyl356 Cyclopropylene C.dbd.O 1-Naphthyl357 Cyclopropylene C.dbd.O 2-Naphthyl358 Cyclopropylene C.dbd.O 4-Biphenyl359 Cyclopropylene C.dbd.O 2-Fluorophenyl360 Cyclopropylene C.dbd.O 4-Fluorophenyl oil 1676, 1600, 1505, 1229, 848, 715361 Cyclopropylene C.dbd.O 2,4-Difluorophenyl362 Cyclopropylene C.dbd.O 2-Chlorophenyl363 Cyclopropylene C.dbd.O 3-Chlorophenyl364 Cyclopropylene C.dbd.O 4-Chlorophenyl oil 1675, 1589, 1424, 1051, 841, 715365 Cyclopropylene C.dbd.O 2,4-Dichlorophenyl366 Cyclopropylene C.dbd.O 3,4-Dichlorophenyl367 Cyclopropylene C.dbd.O 2-Chloro-4-fluorophenyl368 Cyclopropylene C.dbd.O 2-Trifluoromethylphenyl369 Cyclopropylene C.dbd.O 4-Trifluoromethylphenyl370 Cyclopropylene C.dbd.O 4-Methoxyphenyl371 Cyclopropylene C.dbd.O 3,4-Dimethyloxyphenyl372 Cyclopropylene C.dbd.O 4-Tetrafluoroethoxyphenyl373 Cyclopropylene C.dbd.O 4-Trifluoromethoxyphenyl374 Cyclopropylene C.dbd.O 2-Chloro-4-(4'-chlorophenoxy)phenyl375 Cyclopropylene C.dbd.O 4-Phenoxyphenyl376 Cyclopropylene C.dbd.O 4-(4'-Chlorophenoxy)phenyl377 Cyclopropylene C.dbd.O 4-Benzyloxyphenyl378 Cyclopentylene C.dbd.O Phenyl379 Cyclopentylene C.dbd.O 2-Methylphenyl380 Cyclopentylene C.dbd.O 4-Methylphenyl381 Cyclopentylene C.dbd.O 2,4-Dimethylphenyl382 Cyclopentylene C.dbd.O 2,6-Dimethylphenyl383 Cyclopentylene C.dbd.O 2,4,6-Trimethylphenyl384 Cyclopentylene C.dbd.O 4-tert. Butylphenyl385 Cyclopentylene C.dbd.O 1-Naphthyl386 Cyclopentylene C.dbd.O 2-Naphthyl387 Cyclopentylene C.dbd.O 4-Biphenyl388 Cyclopentylene C.dbd.O 2-Fluorophenyl389 Cyclopentylene C.dbd.O 4-Fluorophenyl oil 3.15 (s, 2H, --CH.sub.2 -Py)390 Cyclopentylene C.dbd.O 2,4-Difluorophenyl391 Cyclopentylene C.dbd.O 2-Chlorophenyl392 Cyclopentylene C.dbd.O 3-Chlorophenyl393 Cyclopentylene C.dbd.O 4-Chlorophenyl oil 3.15 (s, 2H, --CH.sub.2 -Py)394 Cyclopentylene C.dbd.O 2,4-Dichlorophenyl oil 1691, 1583, 1423, 1105, 825, 717395 Cyclopentylene C.dbd.O 3,4-Dichlorophenyl396 Cyclopentylene C.dbd.O 2-Chloro-4-fluorophenyl397 Cyclopentylene C.dbd.O 2-Trifluoromethylphenyl398 Cyclopentylene C.dbd.O 4-Trifluoromethylphenyl399 Cyclopentylene C.dbd.O 4-Methoxyphenyl400 Cyclopentylene C.dbd.O 3,4-Dimethoxyphenyl401 Cyclopentylene C.dbd.O 4-Tetrafluoroethoxyphenyl402 Cyclopentylene C.dbd.O 4-Trifluoromethoxyphenyl403 Cyclopentylene C.dbd.O 2-Chloro-4-(4'-chlorophenoxy)phenyl404 Cyclopentylene C.dbd.O 4-Phenoxyphenyl405 Cyclopentylene C.dbd.O 4-(4'-Chlorophenoxy)phenyl406 Cyclopentylene C.dbd.O 4-Benzyloxyphenyl407 Cyclohexylene C.dbd.O Phenyl408 Cyclohexylene C.dbd.O 2-Methylphenyl409 Cyclohexylene C.dbd.O 4-Methylphenyl410 Cyclohexylene C.dbd.O 2,4-Dimethylphenyl411 Cyclohexylene C.dbd.O 2,6-Dimethylphenyl412 Cyclohexylene C.dbd.O 2,4,6-Trimethylphenyl413 Cyclohexylene C.dbd.O 4-tert. Butylphenyl414 Cyclohexylene C.dbd.O 1-Naphthyl415 Cyclohexylene C.dbd.O 2-Naphthyl416 Cyclohexylene C.dbd.O 4-Biphenyl417 Cyclohexylene C.dbd.O 2-Fluorophenyl418 Cyclohexylene C.dbd.O 4-Fluorophenyl419 Cyclohexylene C.dbd.O 2,4-Difluorophenyl420 Cyclohexylene C.dbd.O 2-Chlorophenyl421 Cyclohexylene C.dbd.O 3-Chlorophenyl422 Cyclohexylene C.dbd.O 4-Chlorophenyl oil 3.1 (s, 2H, --CH.sub.2 -Py)423 Cyclohexylene C.dbd.O 2,4-Dichlorophenyl424 Cyclohexylene C.dbd.O 3,4-Dichlorophenyl425 Cyclohexylene C.dbd.O 2-Chloro-4-fluorophenyl426 Cyclohexylene C.dbd.O 2-Trifluoromethylphenyl427 Cyclohexylene C.dbd.O 4-Trifluoromethylphenyl428 Cyclohexylene C.dbd.O 4-Methoxyphenyl429 Cyclohexylene C.dbd.O 3,4-Dimethoxyphenyl430 Cyclohexylene C.dbd.O 4-Tetrafluoroethoxyphenyl431 Cyclohexylene C.dbd.O 4-Trifluoromethoxyphenyl432 Cyclohexylene C.dbd.O 2-Chloro-4-(4'-chlorophenoxy)phenyl433 Cyclohexylene C.dbd.O 4-Phenoxyphenyl434 Cyclohexylene C.dbd.O 4-(4'-Chlorophenoxy)phenyl435 Cyclohexylene C.dbd.O 4-Benzyloxyphenyl436 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O Phenyl437 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2-Methylphenyl438 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Methylphenyl439 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2,4-Dimethylphenyl440 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2,6-Dimethylphenyl441 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2,4,6-Trimethylphenyl442 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-tert. Butylphenyl443 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 1-Naphthyl444 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2-Naphthyl445 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Biphenyl446 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2-Fluorophenyl447 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Fluorophenyl448 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2,4-Difluorophenyl449 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2-Chlorophenyl450 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 3-Chlorophenyl451 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Chlorophenyl452 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2,4-Dichlorophenyl453 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 3,4-Dichlorophenyl454 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2-Chloro-4-fluorophenyl455 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2-Trifluoromethylphenyl456 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Trifluoromethylphenyl457 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Methoxyphenyl458 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 3,4-Dimethoxyphenyl459 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Tetrafluoroethoxyphenyl460 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Trifluoromethoxyphenyl461 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 2-Chloro-4-(4'-chlorophenoxy)phenyl462 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Phenoxyphenyl463 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-(4'-Chlorophenoxy)phenyl464 C(CH.sub.3)(C.sub.3 H.sub.7) C.dbd.O 4-Benzyloxyphenyl465 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O Phenyl466 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2-Methylphenyl467 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Methylphenyl468 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2,4-Dimethylphenyl469 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2,6-Dimethylphenyl470 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2,4,6-Trimethylphenyl471 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-tert. Butylphenyl472 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 1-Naphthyl473 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2-Naphthyl474 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Biphenyl475 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2-Fluorophenyl476 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Fluorophenyl477 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2,4-Difluorophenyl478 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2-Chlorophenyl479 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 3-Chlorophenyl480 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Chlorophenyl481 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2,4-Dichlorophenyl482 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 3,4-Dichlorophenyl483 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2-Chloro-4-fluorophenyl484 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2-Trifluoromethylphenyl485 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Trifluoromethylphenyl486 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Methoxyphenyl487 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 3,4-Dimethoxyphenyl488 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Tetrafluoroethoxyphenyl489 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Trifluoromethoxyphenyl490 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 2-Chloro-4-(4'-chlorophenoxy)-phenyl491 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Phenoxyphenyl492 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-(4'-Chlorophenoxy)phenyl493 C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) C.dbd.O 4-Benzyloxyphenyl494 CH(tert.C.sub.4 H.sub.9) C.dbd.O Phenyl495 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2-Methylphenyl496 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Methylphenyl497 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2,4-Dimethylphenyl498 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2,6-Dimethylphenyl499 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2,4,6-Trimethylphenyl500 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-tert. Butylphenyl501 CH(tert.C.sub.4 H.sub.9) C.dbd.O 1-Naphthyl502 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2-Naphthyl503 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Biphenyl504 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2-Fluorophenyl505 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Fluorophenyl506 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2,4-Difluorophenyl507 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2-Chlorophenyl508 CH(tert.C.sub.4 H.sub.9) C.dbd.O 3-Chlorophenyl509 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Chlorophenyl510 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2,4-Dichlorophenyl511 CH(tert.C.sub.4 H.sub.9) C.dbd.O 3,4-Dichlorophenyl512 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2-Chloro-4-fluorophenyl513 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2-Trifluoromethylphenyl514 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Trifluoromethylphenyl515 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Methoxyphenyl516 CH(tert.C.sub.4 H.sub.9) C.dbd.O 3,4-Dimethoxyphenyl517 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Tetrafluoroethoxyphenyl518 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Trifluoromethoxyphenyl519 CH(tert.C.sub.4 H.sub.9) C.dbd.O 2-Chloro-4-(4'-chlorophenoxy)phenyl520 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Phenoxyphenyl521 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-(4'-Chlorophenoxy)phenyl522 CH(tert.C.sub.4 H.sub.9) C.dbd.O 4-Benzyloxyphenyl523 C(CH.sub.3).sub.2 CHCl Phenyl 75-80.degree. C.524 C(CH.sub.3).sub.2 CHCl 2-Methylphenyl 212-215.degree. C.525 C(CH.sub.3).sub.2 CHCl 4-Methylphenyl 108-109.degree. C.526 C(CH.sub.3).sub.2 CHCl 2,4-Dimethylphenyl527 C(CH.sub.3).sub.2 CHCl 2,6-Dimethylphenyl528 C(CH.sub.3).sub.2 CHCl 2,4,6-Trimethylphenyl 215- 218.degree. C.529 C(CH.sub.3).sub.2 CHCl 4-tert. Butylphenyl 143-147.degree. C.530 C(CH.sub.3).sub.2 CHCl 1-Naphthyl531 C(CH.sub.3).sub.2 CHCl 2-Naphthyl532 C(CH.sub.3).sub.2 CHCl 4-Biphenyl533 C(CH.sub.3).sub.2 CHCl 2-Fluorophenyl534 C(CH.sub.3).sub.2 CHCl 4-Fluorophenyl535 C(CH.sub.3).sub.2 CHCl 2,4-Difluorophenyl536 C(CH.sub.3).sub.2 CHCl 2-Chlorophenyl537 C(CH.sub.3).sub.2 CHCl 3-Chlorophenyl538 C(CH.sub.3).sub.2 CHCl 4-Chlorophenyl 155-158.degree. C.539 C(CH.sub.3).sub.2 CHCl 2,4-Dichlorophenyl540 C(CH.sub.3).sub.2 CHCl 3,4-Dichlorophenyl541 C(CH.sub.3).sub.2 CHCl 2-Chloro-4-fluorophenyl542 C(CH.sub.3).sub.2 CHCl 2-Trifluoromethylphenyl543 C(CH.sub.3).sub.2 CHCl 4-Trifluoromethylphenyl544 C(CH.sub.3).sub.2 CHCl 4-Methoxyphenyl545 C(CH.sub.3).sub.2 CHCl 3,4-Dimethoxyphenyl546 C(CH.sub.3).sub.2 CHCl 4-Tetrafluoroethoxyphenyl547 C(CH.sub.3).sub.2 CHCl 4-Trifluoromethoxyphenyl548 C(CH.sub.3).sub.2 CHCl 2-Chloro-4-(4'-chlorophenoxy)phenyl549 C(CH.sub.3).sub.2 CHCl 4-Phenoxyphenyl550 C(CH.sub.3).sub.2 CHCl 4-(4'-Chlorophenoxy)phenyl551 C(CH.sub.3).sub.2 CHCl 4-Benzyloxyphenyl552 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl Phenyl553 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2-Methylphenyl554 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Methylphenyl555 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2,4-Dimethylphenyl556 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2,6-Dimethylphenyl557 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2,4,6-Trimethylphenyl558 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-tert. Butylphenyl559 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 1-Naphthyl560 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2-Naphthyl561 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Biphenyl562 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2-Fluorophenyl563 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Fluorophenyl564 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2,4-Difluorophenyl565 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2-Chlorophenyl566 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 3-Chlorophenyl567 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Chlorophenyl568 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2,4-Dichlorophenyl569 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 3,4-Dichlorophenyl570 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2-Chloro-4-fluorophenyl571 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2-Trifluoromethylphenyl572 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Trifluoromethylphenyl573 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Methoxyphenyl574 C(CH.sub.3)(CH.sub. 2 CH.sub.3) CHCl 3,4-Dimethoxyphenyl575 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Tetrafluoroethoxyphenyl576 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Trifluoromethoxyphenyl577 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 2-Chloro-4-(4'-chlorophenoxy)phenyl578 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Phenoxyphenyl579 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-(4'-Chlorophenoxy)phenyl580 C(CH.sub.3)(CH.sub.2 CH.sub.3) CHCl 4-Benzyloxyphenyl581 C(CH.sub.2 CH.sub.3).sub.2 CHCl Phenyl oil 2967, 2939, 1478, 1452, 1423, 1027582 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2-Methylphenyl 153-155.degree. C.583 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Methylphenyl584 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2,4-Dimethylphenyl585 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2,6-Dimethylphenyl586 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2,4,6-Trimethylphenyl 142-146.degree. C.587 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-tert. Butylphenyl588 C(CH.sub.2 CH.sub.3).sub.2 CHCl 1-Naphthyl589 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2-Naphthyl590 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Biphenyl591 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2-Fluorophenyl592 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Fluorophenyl593 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2,4-Difluorophenyl594 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2-Chlorophenyl595 C(CH.sub.2 CH.sub.3).sub.2 CHCl 3-Chlorophenyl596 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Chlorophenyl597 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2,4-Dichlorophenyl598 C(CH.sub.2 CH.sub.3).sub.2 CHCl 3,4-Dichlorophenyl599 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2-Chloro-4-fluorophenyl600 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2-Trifluoromethylphenyl601 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Trifluoromethylphenyl602 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Methoxyphenyl 87.degree. C.603 C(CH.sub.2 CH.sub.3).sub.2 CHCl 3,4-Dimethoxyphenyl604 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Tetrafluoroethoxyphenyl605 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Trifluoromethoxyphenyl606 C(CH.sub.2 CH.sub.3).sub.2 CHCl 2-Chloro-4-(4'-chlorophenoxy)phenyl607 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Phenoxyphenyl608 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-(4'-Chlorophenoxy)phenyl609 C(CH.sub.2 CH.sub.3).sub.2 CHCl 4-Benzyloxyphenyl610 Cyclopropylene CHCl Phenyl611 Cyclopropylene CHCl 2-Methylphenyl612 Cyclopropylene CHCl 4-Methylphenyl613 Cyclopropylene CHCl 2,4-Dimethylphenyl614 Cyclopropylene CHCl 2,6-Dimethylphenyl615 Cyclopropylene CHCl 2,4,6-Trimethylphenyl616 Cyclopropylene CHCl 4-tert. Butylphenyl617 Cyclopropylene CHCl 1-Naphthyl618 Cyclopropylene CHCl 2-Naphthyl619 Cyclopropylene CHCl 4-Biphenyl620 Cyclopropylene CHCl 2-Fluorophenyl621 Cyclopropylene CHCl 4-Fluorophenyl622 Cyclopropylene CHCl 2,4-Difluorophenyl623 Cyclopropylene CHCl 2-Chlorophenyl624 Cyclopropylene CHCl 3-Chlorophenyl625 Cyclopropylene CHCl 4-Chlorophenyl626 Cyclopropylene CHCl 2,4-Dichlorophenyl627 Cyclopropylene CHCl 3,4-Dichlorophenyl628 Cyclopropylene CHCl 2-Chloro-4-fluorophenyl629 Cyclopropylene CHCl 2-Trifluoromethylphenyl630 Cyclopropylene CHCl 4-Trifluoromethylphenyl631 Cyclopropylene CHCl 4-Methoxyphenyl632 Cyclopropylene CHCl 3,4-Dimethoxyphenyl633 Cyclopropylene CHCl 4-Tetrafluoroethoxyphenyl634 Cyclopropylene CHCl 4-Trifluoromethoxyphenyl635 Cyclopropylene CHCl 2-Chloro-4-(4'-chlorophenoxy)phenyl636 Cyclopropylene CHCl 4-Phenoxyphenyl637 Cyclopropylene CHCl 4-(4'-Chlorophenoxy)phenyl638 Cyclopropylene CHCl 4-Benzyloxyphenyl639 Cyclopentylene CHCl Phenyl640 Cyclopentylene CHCl 2-Methylphenyl641 Cyclopentylene CHCl 4-Methylphenyl642 Cyclopentylene CHCl 2,4-Dimethylphenyl643 Cyclopentylene CHCl 2,6-Dimethylphenyl644 Cyclopentylene CHCl 2,4,6-Trimethylphenyl645 Cyclopentylene CHCl 4-tert. Butylphenyl646 Cyclopentylene CHCl 1-Naphthyl647 Cyclopentylene CHCl 2-Naphthyl648 Cyclopentylene CHCl 4-Biphenyl649 Cyclopentylene CHCl 2-Fluorophenyl650 Cyclopentylene CHCl 4-Fluorophenyl oil 2959, 1606, 1510, 1478, 1423, 1228651 Cyclopentylene CHCl 2,4-Difluorophenyl652 Cyclopentylene CHCl 2-Chlorophenyl653 Cyclopentylene CHCl 3-Chlorophenyl654 Cyclopentylene CHCl 4-Chlorophenyl oil 2959, 2873, 1492, 1478, 1423, 1408655 Cyclopentylene CHCl 2,4-Dichlorophenyl656 Cyclopentylene CHCl 3,4-Dichlorophenyl657 Cyclopentylene CHCl 2-Chloro-4-fluorophenyl658 Cyclopentylene CHCl 2-Trifluoromethylphenyl659 Cyclopentylene CHCl 4-Trifluoromethylphenyl660 Cyclopentylene CHCl 4-Methoxyphenyl661 Cyclopentylene CHCl 3,4-Dimethoxyphenyl662 Cyclopentylene CHCl 4-Tetrafluoroethoxyphenyl663 Cyclopentylene CHCl 4-Trifluoromethoxyphenyl664 Cyclopentylene CHCl 2-Chloro-4-(4'-chlorophenoxy)phenyl665 Cyclopentylene CHCl 4-Phenoxyphenyl666 Cyclopentylene CHCl 4-(4'-Chlorophenoxy)phenyl667 Cyclopentylene CHCl 4-Benzyloxyphenyl668 Cyclohexylene CHCl Phenyl 230.degree. C.669 Cyclohexylene CHCl 2-Methylphenyl670 Cyclohexylene CHCl 4-Methylphenyl 213-216.degree. C.671 Cyclohexylene CHCl 2,4-Dimethylphenyl672 Cyclohexylene CHCl 2,6-Dimethylphenyl673 Cyclohexylene CHCl 2,4,6-Trimethylphenyl674 Cyclohexylene CHCl 4-tert. Butylphenyl675 Cyclohexylene CHCl 1-Naphthyl676 Cyclohexylene CHCl 2-Naphthyl677 Cyclohexylene CHCl 4-Biphenyl678 Cyclohexylene CHCl 2-Fluorophenyl679 Cyclohexylene CHCl 4-Fluorophenyl 170-173.degree. C.680 Cyclohexylene CHCl 2,4-Difluorophenyl681 Cyclohexylene CHCl 2-Chlorophenyl682 Cyclohexylene CHCl 3-Chlorophenyl683 Cyclohexylene CHCl 4-Chlorophenyl 163.degree. C.684 Cyclohexylene CHCl 2,4-Dichlorophenyl685 Cyclohexylene CHCl 3,4-Dichlorophenyl686 Cyclohexylene CHCl 2-Chloro-4-fluorophenyl687 Cyclohexylene CHCl 2-Trifluoromethylphenyl688 Cyclohexylene CHCl 4-Trifluoromethylphenyl689 Cyclohexylene CHCl 4-Methoxyphenyl690 Cyclohexylene CHCl 3,4-Dimethoxyphenyl691 Cyclohexylene CHCl 4-Tetrafluoroethoxyphenyl692 Cyclohexylene CHCl 4-Trifluoromethoxyphenyl693 Cyclohexylene CHCl 2-Chloro-4-(4'-chlorophenoxy)phenyl694 Cyclohexylene CHCl 4-Phenoxyphenyl695 Cyclohexylene CHCl 4-(4'-Chlorophenoxy)phenyl696 Cyclohexylene CHCl 4-Benzyloxyphenyl697 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl Phenyl698 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2-Methylphenyl699 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-Methylphenyl700 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2,4-Dimethylphenyl701 C(CH.sub.3)(C.sub. 3 H.sub.7) CHCl 2,6-Dimethylphenyl702 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2,4,6-Trimethylphenyl703 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-tert. Butylphenyl704 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 1-Naphthyl705 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2-Naphthyl706 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-Biphenyl707 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2-Fluorophenyl708 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-Fluorophenyl709 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2,4-Difluorophenyl710 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2-Chlorophenyl711 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 3-Chlorophenyl712 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-Chlorophenyl713 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2,4-Dichlorophenyl714 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 3,4-Dichlorophenyl715 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2-Chloro-4-fluorophenyl716 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2-Trifluoromethylphenyl717 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-Trifluoromethylphenyl718 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-Methoxyphenyl719 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 3,4-Dimethoxyphenyl720 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-Tetrafluoroethoxyphenyl721 C(CH.sub.3 )(C.sub.3 H.sub.7) CHCl 4-Trifluoromethoxyphenyl722 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 2-Chloro-4-(4'-chlorophenoxy)phenyl723 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-Phenoxyphenyl724 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-(4'-Chlorophenoxy)phenyl725 C(CH.sub.3)(C.sub.3 H.sub.7) CHCl 4-Benzyloxyphenyl726 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl Phenyl727 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2-Methylphenyl728 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Methylphenyl729 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2,4-Dimethylphenyl730 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2,6-Dimethylphenyl731 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2,4,6-Trimethylphenyl732 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-tert. Butylphenyl733 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 1-Naphthyl734 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2-Naphthyl735 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Biphenyl736 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2-Fluorophenyl737 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Fluorophenyl738 C(C.sub.2 H.sub.5)(n-C.sub. 4 H.sub.9) CHCl 2,4-Difluorophenyl739 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2-Chlorophenyl740 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 3-Chlorophenyl741 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Chlorophenyl742 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2,4-Dichlorophenyl743 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 3,4-Dichlorophenyl744 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2-Chloro-4-fluorophenyl745 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2-Trifluoromethylphenyl746 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Trifluoromethylphenyl747 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Methoxyphenyl748 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 3,4-Dimethoxyphenyl749 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Tetrafluoroethoxyphenyl750 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Trifluoromethoxyphenyl751 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 2-Chloro-4-(4'-chlorophenoxy)-phenyl752 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Phenoxyphenyl753 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-(4'-Chlorophenoxy)phenyl754 C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9) CHCl 4-Benzyloxyphenyl755 CH(tert.C.sub.4 H.sub.9) CHCl Phenyl756 CH(tert.C.sub.4 H.sub.9) CHCl 2-Methylphenyl757 CH(tert.C.sub.4 H.sub.9) CHCl 4-Methylphenyl758 CH(tert.C.sub.4 H.sub.9) CHCl 2,4-Dimethylphenyl759 CH(tert.C.sub.4 H.sub.9) CHCl 2,6-Dimethylphenyl760 CH(tert.C.sub.4 H.sub.9) CHCl 2,4,6-Trimethylphenyl761 CH(tert.C.sub.4 H.sub.9) CHCl 4-tert. Butylphenyl762 CH(tert.C.sub.4 H.sub.9) CHCl 1-Naphthyl763 CH(tert.C.sub.4 H.sub.9) CHCl 2-Naphthyl764 CH(tert.C.sub.4 H.sub.9) CHCl 4-Biphenyl765 CH(tert.C.sub.4 H.sub.9) CHCl 2-Fluorophenyl766 CH(tert.C.sub.4 H.sub.9) CHCl 4-Fluorophenyl767 CH(tert.C.sub.4 H.sub.9) CHCl 2,4-Difluorophenyl768 CH(tert.C.sub.4 H.sub.9) CHCl 2-Chlorophenyl769 CH(tert.C.sub.4 H.sub.9) CHCl 3-Chlorophenyl770 CH(tert.C.sub.4 H.sub.9) CHCl 4-Chlorophenyl771 CH(tert.C.sub.4 H.sub.9) CHCl 2,4-Dichlorophenyl772 CH(tert.C.sub.4 H.sub.9) CHCl 3,4-Dichlorophenyl773 CH(tert.C.sub.4 H.sub.9) CHCl 2-Chloro-4-fluorophenyl774 CH(tert.C.sub.4 H.sub.9) CHCl 2-Trifluoromethylphenyl775 CH(tert.C.sub.4 H.sub.9) CHCl 4-Trifluoromethylphenyl776 CH(tert.C.sub.4 H.sub.9) CHCl 4-Methoxyphenyl777 CH(tert.C.sub.4 H.sub.9) CHCl 3,4-Dimethoxyphenyl778 CH(tert.C.sub.4 H.sub.9) CHCl 4-Tetrafluoroethoxyphenyl779 CH(tert.C.sub.4 H.sub.9) CHCl 4-Trifluoromethoxyphenyl780 CH(tert.C.sub.4 H.sub.9) CHCl 2-Chloro-4-(4'-chlorophenoxy)phenyl781 CH(tert.C.sub.4 H.sub.9) CHCl 4-Phenoxyphenyl782 CH(tert.C.sub.4 H.sub.9) CHCl 4-(4'-Chlorophenoxy)phenyl783 CH(tert.C.sub.4 H.sub.9) CHCl 4-Benzyloxyphenyl784 C(CH.sub.3).sub.2 CHOH 3-Methylphenyl 86-88.degree. C.785 C(CH.sub.3).sub.2 CHOH 2-Methoxyphenyl 128-130.degree. C.786 C(CH.sub.3).sub.2 CHOH 3-Fluorophenyl 3200, 2965, 1589, 1480, 1046787 C(CH.sub.3).sub.2 CHOH 4-Isopropylphenyl 97-98.degree. C.788 C(C.sub.2 H.sub.5).sub.2 CHOH 3-Methylphenyl 3200, 2963, 1424, 1030, 716789 C(C.sub.2 H.sub.5).sub.2 CHOH 3-Trifluoromethylphenyl 117-119.degree. C.790 C(C.sub.2 H.sub.5).sub.2 CHOH 2-Methoxyphenyl 3200, 2962, 1488, 1238, 1030, 755791 C(C.sub.2 H.sub.5).sub.2 CHOH 3-Fluorophenyl 3200, 2966, 1589, 1480, 1258792 Cyclopentylene CHOH 3-Trifluoromethylphenyl 3200, 2956, 1329, 1163, 708793 Cyclopentylene CHOH 3-Methylphenyl 3236, 2952, 1425, 1030, 717794 Cyclopentylene CHOH 2-Methoxyphenyl 94-98.degree. C.795 Cyclopentylene CHOH 4-tert.-Butylphenyl 106-108.degree. C.796 Cyclopentylene CHOH 3-Fluorophenyl 3200, 2954, 1588, 1030, 717797 Cyclopentylene CHOH 4-Isopropylphenyl 3227, 2957, 1424, 1030, 717798 Cyclohexylene CHOH 3-Methylphenyl 137-139.degree. C.799 Cyclohexylene CHOH 4-Isopropylphenyl 98-100.degree. C.800 Cyclohexylene CHOH 3-Trifluoromethylphenyl 3180, 2931, 1510, 1244, 1038, 713801 Cyclohexylene CHOH 2-Methoxyphenyl 141-142.degree. C.802 Cyclohexylene CHOH 3-Fluorophenyl 146-148.degree. C.803 C(CH.sub.3).sub.2 CHCl 3-Methylphenyl 144-146.degree. C.804 C(CH.sub.3).sub.2 CHCl 3-Fluorophenyl 165-167.degree. C.805 C(CH.sub.3).sub.2 CHCl 4-Isopropylphenyl 104-108.degree. C.806 C(C.sub.2 H.sub.5).sub.2 CHCl 3-Trifluoromethylphenyl 66-69.degree. C.807 C(C.sub.2 H.sub.5).sub.2 CHCl 3-Fluorophenyl 205-207.degree. C.808 C(C.sub.2 H.sub.5).sub.2 CHCl 3-Methylphenyl 107-110.degree. C.809 C(C.sub.2 H.sub.5).sub.2 CHCl 2-Methoxyphenyl 83.degree. C.810 Cyclopentylene CHCl 2-Methoxyphenyl 142-143.degree. C.811 C(CH.sub.3).sub.2 C.dbd.NOCH.sub.3 4-Chlorophenyl 47-49.degree. C.812 C(CH.sub.3).sub.2 C.dbd.NOCH.sub.3 4-Methylphenyl 159-161.degree. C.813 C(CH.sub.3).sub.2 C.dbd.NOCH.sub.3 4-Fluorophenyl 2970, 1507, 1423, 1224, 1067814 Cyclopentylene C.dbd.NOCH.sub.3 4-Fluorophenyl 138-140.degree. C.__________________________________________________________________________
In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and can be used as foliar and soil fungicides.
The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, cots, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.
The novel compounds are particularly useful for controlling the following plant diseases:
Erysiphe graminis in cereals,
Erysiphe cichoracearum and Sphgaerotheca fuliginea in cucurbits,
Podosphaera leucotricha in applies,
Uncinula necator in vines,
Puccinia species in cereals,
Rhizoctonia solani in cotton and lawns,
Ustilago species in ceraisland suga cane,
Venturia inaequalis (scab) in applies,
Helminthosporium species in cereals,
Septoria nodorum in wheat,
Botrytis cinerea (gray mold) in strawberries and grapes,
Cersospora arachidicola in ground nuts,
Pseudocercosporella herpotrichoides in wheat and barley,
Pyricularia oryzae in rice,
Phytophthora infestans in potatoes and tomatoes,
Fusarium and Verticillium species in various plants,
Fusarium and Verticillium species in various plants,
Plasmopara viticola in grapes,
Alternaria species in fruit and vegetables.
The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi, or the plants, seed or materials to be protected against fungus attack, or the soil, are treated with a fungicidally effective amount of the active ingredient.
The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and aryl sulfonates); and dispersants such as ligninsulfite waste liquors and methylcellulose.
The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt. % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials, e.g., against Paecilomyces variotii. When the active ingredients are used for treating seed, generally amounts of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are required.
The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.
Examples of formulations are given below.
I. A solution of 90 parts by weight of compound no. 1 and 10 parts by weight of N-methyl-.alpha.-pyrrolidone, which is suitable for application in the form of very fine drops.
II. A mixture of 20 parts by weight of compound no. 3, 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 the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
III. An aqueous dispersion of 20 parts by weight of compound no. 12, 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. By finely dispersing the mixture of water, an aqueous dispersion is obtained.
IV. An aqueous dispersion of 20 parts by weight of compound no. 16, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280.degree. C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained.
V. A hammer-milled mixture of 80 parts by weight of compound no. 30, 3 parts by weight of the sodium salt of diisobutylnaphthalene-.alpha.-sulfonic acid, 10 pats by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.
VI. An intimate mixture of 3 parts by weight of compound no. 32 and 97 parts by weight of particulate kaolin. The dust contains 3 wt. % of the active ingredient.
VII. An intimate mixture of 30 parts by weight of compound no. 41, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.
VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 45, 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water, which dispersion can be further diluted.
IX. A stable oily dispersion of 20 parts by weight of compound no. 61, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.
USE EXAMPLES
The active ingredient used for comparison purposes was 1-phenyl-3-(3-pyridinyl)-propan-1-one (A) disclosed in J. Org. Chem., Vol. 43 (1978), p. 3396.
Use Example 1
Action on Alternaria solani
Potted tomato plants of the "Gro.beta.e Fleischtomat" variety grown in the greenhouse were sprayed to runoff at the 4-leaf stage with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the leaves were inoculated with an aqueous spore suspension of the fungus Alternaria solani. These plants were then placed in a water vapor-saturated chamber at from 22 to 24.degree. C. After 4 days, the disease had spread on the untreated but inoculated plants to such a great extent that the fungicidal action of the compounds was able to be assessed.
The results show that active ingredients 1, 3, 12, 16, 30, 32, 41, 45, 61, 74, 117, 119, 128, 132, 133, 161, 175, 177, 186, 204, 206, 215 and 219, applied as 0.05 wt. % spray liquors, have a better fungicidal action (95%) than prior art comparative active ingredient A (10%).
Use Example 2
Action on Botrytis cinerea in paprika
Paprika seedlings of the "Neusideler Ideal Elite" variety were sprayed, after 4 to 5 leaves were well developed, to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient ad 20% of emulsifier. After the sprayed-on layer had dried, the plants were sprinkled with a conidial suspension of the fungus Botrytis cinerea, and placed at 22 to 24.degree..degree. C. in a chamber of high humidity. After 5 days, the disease had spread to such a great extent on the untreated plants that the necroses covered the major portion of the leaves.
The results show that active ingredients 3, 16, 32, 45, 59, 61, 70, 132, 133, 177, 190, 206, 215 and 219, applied as 0.05 wt. % spray liquors, have a better fungicidal action (95%) than prior art comparative agent A (30%).
Use Example 3
Action on Pyrenophora teres
Leaves of pot-grown barley seedlings of the "Igri" variety were sprayed to runoff at the two-leaf stage with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres, and set up in high-humidity climatic cabinet at 18.degree. C. The plants were then cultivated for a further 5 days at 20 to 22.degree. C. and a relative humidity of 70%. The extent of leaf attack was then assessed.
The results show that active ingredients 1, 3, 12, 16, 32, 45, 61, 70, 74, 117, 119, 128, 132, 133, 157, 161, 177, 186, 204, 206, 215, 219, 650 and 683, applied as 0.05 wt % spray liquors, have a better fungicidal action (95%) than prior art comparative agent A (30%).

Number	Name	Date
4753947	Dorn et al.	Jun 1988
4766132	Kay	Aug 1988
4933339	Sharma	Jun 1990
4999357	Gadras et al.	Mar 1991

Derivatives of beta-picoline and crop protection agents containing them

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