# Patent

## Title
Treatment of low pressure glaucoma and ischemic retinal degeneration

## Abstract

This is a continuation of application Ser. No. 07/502,401, filed on Mar. 30, 1990, now U.S. Pat. No. 5,112,828.

## Background
The present invention relates to novel pyridine derivatives, the N-oxides and salts thereof, to a process for the preparation thereof and the use thereof for controlling fungi.

The novel pyridine derivatives have the formula ##STR3## where R.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or COR.sup.2 ; -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl or substituted or unsubstituted aryl; ##STR4## R.sup.3 and R.sup.4 are, independently of one another, C.sub.1 -C.sub.6 -alkyl with the proviso that R.sup.3 and R.sup.4 are not both methyl; CH.sub.2, CH.sub.2 CH.sub.2 O, CH.sub.2 CH.sub.2 S(O).sub.m where -C.sub.6 -alkyl, phenyl, halogen, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxyiminomethyl, phenoxy, halophenoxy and benzyloxy, and the N-oxides and the acid addition salts which are tolerated by plants of the pyridine compounds.

Examples of R.sup.1 are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso-pentyl, n-hexyl; allyl, 2-methylallyl, 3-methylallyl, 3,3-dimethylallyl; propargyl.

Examples of R.sup.2 are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentenyl, neo-pentyl, n-hexyl; trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, 2-bromoethyl, 2-chloroethyl, 3-bromopropyl, 4-bromobutyl; aryl which carries zero to three substituents selected from the group comprising 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, such as naphthyl, phenyl, mono-, di- or trimethylphenyl, 4-tert-butylphenyl, mono-, di- or trimethoxyphenyl, trifluoromethylphenyl, fluorophenyl, mono-, di- or trichlorophenyl, mono- or dinitrophenyl and cyanophenyl.

Examples of R.sup.3 and R.sup.4 are, independently of one another, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and n-hexyl.

Examples of R.sup.5 are methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, oxydimethylene, ethyleneoxy, thiodimethylene, sulfinyldimethylene, sulfonyldimethylene, ethylenethio, ethylenesulfinyl and ethylenesulfonyl.

Examples of Ar are phenyl, naphthyl, indanyl, mono-, di-, tri- or tetramethylphenyl, ethylphenyl, propylphenyl, isopropylphenyl, butylphenyl, tert-butylphenyl, biphenyl, methylnaphthyl, mono- or difluorophenyl, methylfluorophenyl, tri-, tetra- or pentafluorophenyl, fluorochlorophenyl, methylchlorophenyl, mono-, di-, tri-, tetra- or pentachlorophenyl, bromophenyl, fluorobromophenyl, mono- or bis-trifluoromethylphenyl, mono-, di- or trimethoxyphenyl, ethoxyphenyl, trifluoromethoxyphenyl, tetrafluoroethoxyphenyl, methoxyiminomethylphenyl, ethoxyiminomethylphenyl, phenoxyphenyl, fluorophenoxyphenyl, chlorophenoxyphenyl, chlorophenoxychlorophenyl and benzyloxyphenyl.

Preferred compounds of the formula 1 are those in which COR.sup.2, substituted or unsubstituted phenyl, ##STR5## R.sup.3 and R.sup.4 are, independently of one another, methyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl, claim 1.

The present invention also relates to the N-oxides and the acid addition salts which are tolerated by plants of the novel pyridine derivatives. Examples of salts which are tolerated by plants of the pyridines are salts with mineral acids such as hydrochlorides, hydrobromides, sulfates, nitrates and phosphates; salts with alkanecarboxylic acids such as formates, acetates, propionates, 2-ethylhexanoates and oxalates; salts with arenesulfonic acids such as benzenesulfonates, toluenesulfonates and dodecylbenzenesulfonates.

The compounds of the formula 1 can contain two centers of asymmetry and thus exist in two diastereomeric forms which can be separated by conventional processes, for example by chromatography or crystallization. The present invention embraces both the individual diastereomers and the mixtures thereof and fungicides containing these compounds.

The compounds of the formula 1 have a good fungicidal action which is better than the action of conventional fungicides.

The use of pyridylcarbinols, e.g. 3-phenyl-2,2-dimethyl-1-(3-pyridyl)-1-propanol which is disclosed in EP 302 365, as fungicides has been disclosed. Their fungicidal action is, however, not always entirely satisfactory for certain indications, especially at low application rates.

The process for the preparation of the novel compounds of the formula 1 comprises an aldehyde of the formula 2

in which Ar and A have the meanings specified in claim 1, being reacted with an organometallic compound of the formula 3 ##STR6## in which M is lithium or MgCl, MgBr or MgI, and the resulting pyridyl alcohol of the formula 1 in which A and Ar have the meanings specified in claim 1, and R.sup.1 is hydrogen, being either alkylated with a compound of the formula 4 or acylated with a compound of the formula 5 ##STR7## in which R.sup.1 and R.sup.2 have the meanings specified in claim 1 with the exception of hydrogen, and X and Y are nucleofugic groups.

Examples of X are chlorine, bromine, iodine, OSO.sub.2 CH.sub.3, OSO.sub.2 C.sub.6 H.sub.5 and OSO.sub.2 --C.sub.6 H.sub.4 --CH.sub.3 (p).

Examples of Y are chlorine, bromine, iodine, ##STR8## or 1-imidazolyl.

The procedure for this reaction is such that, for example, a mixture of pyridyl alcohol of the formula 1 in which R.sup.1 is hydrogen is introduced into at least the equimolar amount of an auxiliary base, with or without an inert organic solvent such as diethyl ether, tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide, acetonitrile, toluene or xylene, and then the alkylating or acylating agent is metered in.

The reaction is carried out at from 0.degree. to 120.degree. C., preferably 20.degree. to 80.degree. C., for example.

Auxiliary bases which can be used are inorganic and organic acid-binding agents.

Examples of inorganic bases are sodium hydride, sodamide, sodium hydroxide, sodium carbonate, potassium carbonate, potassium hydroxide etc.

Examples of organic bases are amines, especially tertiary amines such as triethylamine, ethyldiisopropylamine and pyridine, and alcoholates such as sodium methylate, sodium ethylate and potassium tert-butylate.

An occasionally advantageous variant of this process entails reacting the pyridyl alcohols of the formula 1 with alkylating agents of the formula 4 in a two-phase system composed of aqueous sodium hydroxide solution and an organic solvent, preferably toluene or dichloromethane, with the addition of a phase-transfer catalyst, e.g. tetra-n-butylammonium chloride, benzyltriethylammonium chloride or methyltrioctylammonium chloride.

The novel pyridyl alcohols of the formula 1 in which R.sup.1 is hydrogen can be prepared, for example, by reacting a metalated pyridine of the formula 3 in which M is lithium or MgCl, MgBr or MgI with an aldehyde of the formula 2 in which Ar and A have the meanings specified in claim 1, e.g. in the presence of a suitable solvent.

This advantageously entails the organometallic compound of the formula 3 being introduced into an inert solvent, preferably an ether such as diethyl ether or tetrahydrofuran, at from -100.degree. to +20.degree. C., preferably from -70.degree. to 0.degree. C., and adding the aldehyde of the formula 2, which may be dissolved in a diluent, dropwise.

The metalated pyridines of the formula 3 are known and can be prepared from the corresponding 3-halopyridines (cf. e.g. N. Furukawa et al., Tetrahedron Letters 1987, 5845 for M=MgBr; A. Fischer and M. W. Morgan, J. Organomet. Chem. 136 (1977) 323 for M=Li).

Some of the aldehydes of the formula 2 are known, and they can be prepared by known processes by alkylating aldehydes of the formula 6 in which A has the meanings specified in claim 1 with a benzyl halide of the formula 7: ##STR9##

It is known that direct .alpha.-alkylation of aldehydes usually takes place with only poor yields; the same applies to the enamines derived from the aldehydes (cf. e.g. G. Opitz et al., Liebigs Ann. Chem. 649 (1961) 36). Better results are obtained when the aldehydes of the formula 6 are first converted into N-metalated imines which are then alkylated with benzyl halides (cf. H. Normant et al., Bull. Soc. Chim. Fr. 1970, 3976). A more straightforward method is phase-transfer catalyzed .alpha.-alkylation of aldehydes. This process can be carried out as the solid/liquid variant in a two-phase system composed of solid sodium hydroxide and a lipophilic organic solvent (cf. V. G. Poruhit and R. Subramanian, Chem. Ind. (London) 1978, 731) or as the liquid/liquid variant in a two-phase system composed of concentrated sodium hydroxide solution and a lipophilic organic solvent (cf. H. K. Dietl and K. C. Brannock, Tetrahedron Lett. 1973, 1273; E. Buschmann and B. Zeeh, Liebigs Ann. Chem. 1979, 1585).

Another process for the preparation of aldehydes of the formula 2 comprises alkylating nitriles of the formula 8 with benzyl halides of the formula 7, and converting the reaction products of the formula 9 with a suitable reducing agent into the aldehydes 2: ##STR10##

The .alpha.-alkylation of nitriles and the reduction of nitriles to aldehydes are known reactions (cf. e.g. D. S. Watt et al., Org. React. 31 (1984) 1 et seq.; M. Rabinovitz in Z. Rappoport (Ed.) "The Chemistry of the Cyano Group", pp. 307 et seq., Interscience, New York 1970; J. Malek and M. Cerny, Synthesis 1972, 217; N. M. Yoon and Y. S. Gyoung, J. Org. Chem. 50 (1985) 2443).

The aldehydes 6, nitriles 8 and benzyl halides 7 used as starting materials are known, and most of them are commercially available.

The examples which follow illustrate the preparation of the novel pyridine derivatives.

10.2 g (0.10 mol) of acetic anhydride are added dropwise to a solution of 12.1 g (0.04 mol) of 2-(4-chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol in 50 ml of pyridine at room temperature, and the mixture is then heated at 80.degree. C. for 8 h. The reaction mixture is concentrated, the residue is taken up in 200 ml of dichloromethane, and the solution is washed with saturated NaHCO.sub.3 solution and then with water. The organic phase is dried and concentrated, and the remaining black oil is purified on silica gel (mobile phase: 5:1 cyclohexane/ethyl acetate). 11.2 g (81% of theory) of the title compound are obtained as a viscous yellow oil. .sup.1 H-NMR (CDCl.sub.3): .delta.=8.60(2-Hpy), 8.52(6-Hpy), 7.65(4-Hpy), 7.30(5-Hpy), 7.25(2Hm), 7.05(2Ho), 5.62(CHOAc), 2.68(CH.sub.2 Ar), 2.08(COCH.sub.3), 1.45(CH.sub.2), 1.30(CH.sub.2), 0.95(CH.sub.3), 0.83(CH.sub.3).

A solution of 15.8 g of 3-bromopyridine (0.10 mol) in 50 ml of diethyl ether is added dropwise to a mixture of 82 ml of a 1.6M n-butyllithium solution in n-hexane (0.13 mol) under a nitrogen atmosphere at -70.degree. C. The mixture is stirred at -70.degree. C. for 10 minutes and then a solution of 24.7 g of 2-(4-chlorobenzyl)-2-ethylbutanal (0.11 mol) in 50 ml of diethyl ether is added dropwise. After 1 h at -70.degree. C., the mixture is allowed to warm slowly to room temperature and is hydrolyzed with saturated aqueous ammonium chloride solution. The mixture is acidified with dilute hydrochloric acid, and the aqueous phase is separated off and washed with ether and then adjusted to pH 10 to 11 with concentrated ammonia solution while cooling. It is extracted three times with dichloromethane, and the organic phase is dried over Na.sub.2 SO.sub.4 and concentrated. The solid crude product is recrystallized from ethyl acetate/hexane (1:1). 19.2 g (63% of theory) of colorless crystals of melting point 128.degree.-129.degree. C.

300 ml of toluene, 400 ml of 30 percent (by weight) sodium hydroxide solution and 5.0 g of tetra-n-butyl-ammonium iodide are heated at 80.degree. C. while stirring. To this is slowly added dropwise a mixture of 110 g (1.10 mol) of 2-ethylbutanal and 161 g (1.00 mol) of 4-chlorobenzyl chloride. The mixture is then stirred at 80.degree. C. for 4 h and at room temperature for 14 h, 1,000 ml of toluene are added, and the phases are separated. The organic phase is washed with water, dried over Na.sub.2 SO.sub.4 and concentrated. Fractional distillation results in 123 g (54% of theory) of 2-(4-chlorobenzyl) -2-ethylbutanal as a colorless liquid of boiling point 146.degree.-148.degree. C. at 1 mbar.

The following compounds can also be prepared in a manner corresponding to that in Examples 1 and 2: ______________________________________ ##STR11## Ex.                                 Physical no.  A           Ar                 data ______________________________________ 1   C(CH.sub.3)C.sub.2 H.sub.5 phenyl 2   C(CH.sub.3)C.sub.2 H.sub.5 2-methylphenyl 3   C(CH.sub.3)C.sub.2 H.sub.5 3-methylphenyl 4   C(CH.sub.3)C.sub.2 H.sub.5 4-methylphenyl 5   C(CH.sub.3)C.sub.2 H.sub.5 2,3-dimethylphenyl 6   C(CH.sub.3)C.sub.2 H.sub.5 2,4-dimethylphenyl 7   C(CH.sub.3)C.sub.2 H.sub.5 2,5-dimethylphenyl 8   C(CH.sub.3)C.sub.2 H.sub.5 2,6-dimethylphenyl 9   C(CH.sub.3)C.sub.2 H.sub.5 3,4-dimethylphenyl 10  C(CH.sub.3)C.sub.2 H.sub.5 3,5-dimethylphenyl 11  C(CH.sub.3)C.sub.2 H.sub.5 2,4,5-trimethylphenyl 12  C(CH.sub.3)C.sub.2 H.sub.5 2,4,6-trimethylphenyl 13  C(CH.sub.3)C.sub.2 H.sub.5 2,3,5,6-tetramethylphenyl 14  C(CH.sub.3)C.sub.2 H.sub.5 4-ethylphenyl 15  C(CH.sub.3)C.sub.2 H.sub.5 4-isopropylphenyl 16  C(CH.sub.3)C.sub.2 H.sub.5 4-tert.butylphenyl 17  C(CH.sub.3)C.sub.2 H.sub.5 5-indanyl 18  C(CH.sub. 3)C.sub.2 H.sub.5 1-naphthyl 19  C(CH.sub.3)C.sub.2 H.sub.5 2-naphthyl 20  C(CH.sub.3)C.sub.2 H.sub.5 2-methyl-1-naphthyl 21  C(CH.sub.3)C.sub.2 H.sub.5 4-biphenyl 22  C(CH.sub.3)C.sub.2 H.sub.5 2-fluorophenyl 23  C(CH.sub.3)C.sub.2 H.sub.5 3-fluorophenyl 24  C(CH.sub.3)C.sub.2 H.sub.5 4-fluorophenyl 25  C(CH.sub.3)C.sub.2 H.sub.5 2,3-difluorophenyl 26  C(CH.sub.3)C.sub.2 H.sub.5 2,4-difluorophenyl 27  C(CH.sub.3)C.sub.2 H.sub.5 2,5-difluorophenyl 28  C(CH.sub.3)C.sub.2 H.sub.5 2,6-difluorophenyl 29  C(CH.sub.3)C.sub.2 H.sub.5 3,4-difluorophenyl 30  C(CH.sub.3)C.sub.2 H.sub.5 3,5-difluorophenyl 31  C(CH.sub.3)C.sub.2 H.sub.5 2-fluoro-3-methylphenyl 32  C(CH.sub.3)C.sub.2 H.sub.5 2,3,5,6-tetrafluorophenyl 33  C(CH.sub.3)C.sub.2 H.sub.5 pentafluorophenyl 34  C(CH.sub.3)C.sub.2 H.sub.5 2-chlorophenyl 35  C(CH.sub.3)C.sub.2 H.sub.5 3-chlorophenyl 36  C(CH.sub.3)C.sub.2 H.sub.5 4-chlorophenyl 37  C(CH.sub.3)C.sub.2 H.sub.5 2,3-dichlorophenyl 38  C(CH.sub.3)C.sub.2 H.sub.5 2,4-dichlorophenyl 39  C(CH.sub.3)C.sub.2 H.sub.5 2,5-dichlorophenyl 40  C(CH.sub.3)C.sub. 2 H.sub.5 2,6-dichlorophenyl 41  C(CH.sub.3)C.sub.2 H.sub.5 3,4-dichlorophenyl 42  C(CH.sub.3)C.sub.2 H.sub.5 3,5-dichlorophenyl 43  C(CH.sub.3)C.sub.2 H.sub.5 2,4,5-trichlorophenyl 44  C(CH.sub.3)C.sub.2 H.sub.5 2,4,6-trichlorophenyl 45  C(CH.sub.3)C.sub.2 H.sub.5 2,3,6-trichlorophenyl 46  C(CH.sub.3)C.sub.2 H.sub.5 2-chloro-5-methylphenyl 47  C(CH.sub.3)C.sub.2 H.sub.5 3-chloro-4-methylphenyl 48  C(CH.sub.3)C.sub.2 H.sub.5 2-chloro-4-fluorophenyl 49  C(CH.sub.3)C.sub.2 H.sub.5 2-chloro-6-fluorophenyl 50  C(CH.sub.3)C.sub.2 H.sub.5 3-chloro-2-fluorophenyl 51  C(CH.sub.3)C.sub.2 H.sub.5 pentachlorophenyl 52  C(CH.sub.3)C.sub.2 H.sub.5 2-bromophenyl 53  C(CH.sub.3)C.sub.2 H.sub.5 3-bromophenyl 54  C(CH.sub.3)C.sub.2 H.sub.5 4-bromophenyl 55  C(CH.sub.3)C.sub.2 H.sub.5 2-fluoro-4-bromophenyl 56  C(CH.sub.3)C.sub.2 H.sub.5 2-trifluoromethylphenyl 57  C(CH.sub.3)C.sub.2 H.sub.5 3-trifluoromethylphenyl 58  C(CH.sub.3)C.sub.2 H.sub.5 4-trifluoromethylphenyl 59  C(CH.sub.3)C.sub.2 H.sub.5 2,4-bis(trifluoromethyl)phenyl 60  C(CH.sub.3)C.sub.2 H.sub.5 3,5-bis(trifluoromethyl)phenyl 61  C(CH.sub.3)C.sub.2 H.sub.5 2-methoxyphenyl 62  C(CH.sub.3)C.sub.2 H.sub. 5 3-methoxyphenyl 63  C(CH.sub.3)C.sub.2 H.sub.5 4-methoxyphenyl 64  C(CH.sub.3)C.sub.2 H.sub.5 3,4-dimethoxyphenyl 65  C(CH.sub.3)C.sub.2 H.sub.5 3,4,5-trimethoxyphenyl 66  C(CH.sub.3)C.sub.2 H.sub.5 4-ethoxyphenyl 67  C(CH.sub.3)C.sub.2 H.sub.5 4-tetrafluoroethoxyphenyl 68  C(CH.sub.3)C.sub.2 H.sub.5 4-trifluoromethoxyphenyl 69  C(CH.sub.3)C.sub.2 H.sub.5 4-methoxyiminocarbyl-phenyl 70  C(CH.sub.3)C.sub.2 H.sub.5 4-ethoxyiminocarbyl-phenyl 71  C(CH.sub.3)C.sub.2 H.sub.5 4-methoxy-3-methylphenyl 72  C(CH.sub.3)C.sub.2 H.sub.5 3-phenoxyphenyl 73  C(CH.sub.3)C.sub.2 H.sub.5 4-phenoxyphenyl 74  C(CH.sub.3)C.sub.2 H.sub.5 2-chloro-4-(4'-chloro- phenoxy)phenyl 75  C(CH.sub.3)C.sub.2 H.sub.5 4-(4'-chlorophenoxy)- phenyl) 76  C(CH.sub.3)C.sub.2 H.sub.5 3-(4'-fluorophenoxy)- phenyl 77  C(CH.sub.3)C.sub.2 H.sub.5 4-benzyloxyphenyl 78  C(C.sub.2 H.sub.5).sub.2 phenyl             mp. 130- 132 79  C(C.sub.2 H.sub.5).sub.2 2-methylphenyl     mp. 92- 94 80  C(C.sub.2 H.sub.5).sub.2 3-methylphenyl 81  C(C.sub.2 H.sub.5).sub.2 4-methylphenyl     mp. 87- 88 82  C(C.sub.2 H.sub.5).sub.2 2,3-dimethylphenyl 83  C(C.sub.2 H.sub.5).sub.2 2,4-dimethylphenyl 84  C(C.sub.2 H.sub.5).sub.2 2,5-dimethylphenyl 85  C(C.sub.2 H.sub.5).sub.2 2,6-dimethylphenyl 86  C(C.sub.2 H.sub.5).sub.2 3,4-dimethylphenyl 87  C(C.sub.2 H.sub.5).sub.2 3,5-dimethylphenyl 88  C(C.sub.2 H.sub.5).sub.2 2,4,5-trimethylphenyl 89  C(C.sub.2 H.sub.5).sub.2 2,4,6-trimethylphenyl 90  C(C.sub.2 H.sub.5).sub.2 2,3,5,6-tetramethylphenyl 91  C(C.sub.2 H.sub.5).sub.2 4-ethylphenyl 92  C(C.sub.2 H.sub.5).sub.2 4-isopropylphenyl 93  C(C.sub.2 H.sub.5).sub.2 4-tert.butylphenyl mp. 122- 124 94  C(C.sub.2 H.sub.5).sub.2 5-indanyl 95  C(C.sub.2 H.sub.5).sub.2 1-naphthyl         mp. 112- 113 96  C(C.sub.2 H.sub.5).sub.2 2-naphthyl 97  C(C.sub.2 H.sub.5).sub.2 2-methyl-1-naphthyl 98  C(C.sub.2 H.sub.5).sub.2 4-biphenyl 99  C(C.sub.2 H.sub.5).sub.2 2-fluorophenyl 100  C(C.sub.2 H.sub.5).sub.2 3-fluorophenyl     mp. 120- 122 101  C(C.sub.2 H.sub.5).sub.2 4-fluorophenyl     mp. 148- 150 102  C(C.sub.2 H.sub.5).sub.2 2,3-difluorophenyl 103  C(C.sub.2 H.sub.5).sub.2 2,4-difluorophenyl 104  C(C.sub.2 H.sub.5).sub.2 2,5-difluorophenyl 105  C(C.sub.2 H.sub.5).sub.2 2,6-difluorophenyl 106  C(C.sub.2 H.sub.5).sub.2 3,4-difluorophenyl 107  C(C.sub.2 H.sub.5).sub.2 3,5-difluorophenyl 108  C(C.sub.2 H.sub.5).sub.2 2-fluoro-3-methylphenyl 109  C(C.sub.2 H.sub.5).sub.2 2,3,5,6-tetrafluorophenyl 110  C(C.sub.2 H.sub.5).sub.2 pentafluorophenyl 111  C(C.sub.2 H.sub.5).sub.2 2-chlorophenyl     mp. 96- 98 112  C(C.sub.2 H.sub.5).sub.2 3-chlorophenyl 113  C(C.sub.2 H.sub.5).sub.2 4-chlorophenyl     mp. 128- 129 114  C(C.sub.2 H.sub.5).sub.2 2,3-dichlorophenyl 115  C(C.sub.2 H.sub.5).sub.2 2,4-dichlorophenyl mp. 139- 140 116  C(C.sub.2 H.sub.5).sub.2 2,5-dichlorophenyl 117  C(C.sub.2 H.sub.5).sub.2 2,6-dichlorophenyl 118  C(C.sub.2 H.sub.5).sub.2 3,4-dichlorophenyl 119  C(C.sub.2 H.sub.5).sub.2 3,5-dichlorophenyl 120  C(C.sub.2 H.sub.5).sub.2 2,4,5-trichlorophenyl 121  C(C.sub.2 H.sub.5).sub.2 2,4,6-trichlorophenyl 122  C(C.sub.2 H.sub.5).sub.2 2,3,6-trichlorophenyl 123  C(C.sub.2 H.sub.5).sub.2 2-chloro-5-methylphenyl 124  C(C.sub.2 H.sub.5).sub.2 3-chloro-4-methylphenyl 125  C(C.sub.2 H.sub.5).sub.2 2-chloro-4-fluorophenyl 126  C(C.sub.2 H.sub.5).sub.2 2-chloro-6-fluorophenyl 127  C(C.sub.2 H.sub.5).sub.2 3-chloro-2-fluorophenyl 128  C(C.sub.2 H.sub.5).sub.2 pentachlorophenyl 129  C(C.sub.2 H.sub.5).sub.2 2-bromophenyl 130  C(C.sub.2 H.sub.5).sub.2 3-bromophenyl 131  C(C.sub.2 H.sub.5).sub.2 4-bromophenyl 132  C(C.sub.2 H.sub.5).sub.2 2-fluoro-4-bromophenyl 133  C(C.sub.2 H.sub.5).sub.2 2-trifluoromethylphenyl 134  C(C.sub.2 H.sub.5).sub.2 3-trifluoromethylphenyl 135  C(C.sub.2 H.sub.5).sub.2 4-trifluoromethylphenyl 136  C(C.sub.2 H.sub.5).sub.2 2,4-bis(trifluoromethyl)phenyl 137  C(C.sub.2 H.sub.5).sub.2 3,5-bis(trifluoromethyl)phenyl 138  C(C.sub.2 H.sub.5).sub.2 2-methoxyphenyl 139  C(C.sub.2 H.sub.5).sub.2 3-methoxyphenyl 140  C(C.sub.2 H.sub.5).sub.2 4-methoxyphenyl 141  C(C.sub.2 H.sub.5).sub.2 3,4-dimethoxyphenyl 142  C(C.sub.2 H.sub.5).sub.2 3,4,5-trimethoxyphenyl 143  C(C.sub.2 H.sub.5).sub.2 4-ethoxyphenyl 144  C(C.sub.2 H.sub.5).sub.2 4-tetrafluoroethoxyphenyl 145  C(C.sub.2 H.sub.5).sub.2 4-trifluoromethoxyphenyl 146  C(C.sub.2 H.sub.5).sub.2 4-methoxyiminocarbyl-phenyl 147  C(C.sub.2 H.sub.5).sub.2 4-ethoxyiminocarbyl-phenyl 148  C(C.sub.2 H.sub.5).sub.2 4-methoxy-3-methylphenyl 149  C(C.sub.2 H.sub.5).sub.2 3-phenoxyphenyl 150  C(C.sub.2 H.sub.5).sub.2 4-phenoxyphenyl 151  C(C.sub.2 H.sub.5).sub.2 2-chloro-4-(4'-chloro- phenoxy)phenyl 152  C(C.sub.2 H.sub.5).sub.2 4-(4'-chlorophenoxy)- phenyl) 153  C(C.sub.2 H.sub.5).sub.2 4-benzyloxyphenyl 154  C(CH.sub.2).sub.4 phenyl 155  C(CH.sub.2).sub.4 2-methylphenyl 156  C(CH.sub.2).sub.4 3-methylphenyl 157  C(CH.sub.2).sub.4 4-methylphenyl 158  C(CH.sub.2).sub.4 2,3-dimethylphenyl 159  C(CH.sub.2).sub.4 2,4-dimethylphenyl 160  C(CH.sub.2).sub.4 2,5-dimethylphenyl 161  C(CH.sub.2).sub.4 2,6-dimethylphenyl 162  C(CH.sub.2).sub.4 3,4-dimethylphenyl 163  C(CH.sub.2).sub.4 3,5-dimethylphenyl 164  C(CH.sub.2).sub.4 2,4,5-trimethylphenyl 165  C(CH.sub.2).sub.4 2,4,6-trimethylphenyl 166  C(CH.sub.2).sub.4 2,3,5,6-tetramethylphenyl 167  C(CH.sub.2).sub.4 4-ethylphenyl 168  C(CH.sub.2).sub.4 4-isopropylphenyl 169  C(CH.sub.2).sub.4 4-tert.butylphenyl 170  C(CH.sub.2).sub.4 5-indanyl 171  C(CH.sub.2).sub.4 1-naphthyl 172  C(CH.sub.2).sub.4 2-naphthyl 173  C(CH.sub.2).sub.4 2-methyl-1-napthyl 174  C(CH.sub.2).sub.4 4-biphenyl 175  C(CH.sub.2).sub.4 2-fluorophenyl     mp. 75- 76 176  C(CH.sub.2).sub.4 3-fluorophenyl 177  C(CH.sub.2).sub.4 4-fluorophenyl     mp. 166- 168 178  C(CH.sub.2).sub.4 2,3-difluorophenyl 179  C(CH.sub.2).sub.4 2,4-difluorophenyl 180  C(CH.sub.2).sub.4 2,5-difluorophenyl 181  C(CH.sub.2).sub.4 2,6-difluorophenyl 182  C(CH.sub.2).sub.4 3,4-difluorophenyl 183  C(CH.sub.2).sub.4 3,5-difluorophenyl 184  C(CH.sub.2).sub.4 2-fluoro-3-methylphenyl 185  C(CH.sub.2).sub.4 2,3,5,6-tetrafluorophenyl 186  C(CH.sub.2).sub.4 pentafluorophenyl 187  C(CH.sub.2).sub.4 2-chlorophenyl     mp. 114- 116 188  C(CH.sub.2).sub.4 3-chlorophenyl 189  C(CH.sub.2).sub.4 4-chlorophenyl     mp. 162- 164 190  C(CH.sub.2).sub.4 2,3-dichlorophenyl 191  C(CH.sub.2).sub.4 2,4-dichlorophenyl mp. 110- 112 192  C(CH.sub.2).sub.4 2,5-dichlorophenyl 193  C(CH.sub.2).sub.4 2,6-dichlorophenyl 194  C(CH.sub.2).sub.4 3,4-dichlorophenyl 195  C(CH.sub.2).sub.4 3,5-dichlorophenyl 196  C(CH.sub.2).sub.4 2,4,5-trichlorophenyl 197  C(CH.sub.2).sub.4 2,4,6-trichlorophenyl 198  C(CH.sub.2).sub.4 2,3,6-trichlorophenyl 199  C(CH.sub.2).sub.4 2-chloro-5-methylphenyl 200  C(CH.sub.2).sub.4 3-chloro-4-methylphenyl 201  C(CH.sub.2).sub.4 2-chloro-4-fluorophenyl 202  C(CH.sub.2).sub.4 2-chloro-6-fluorophenyl 203  C(CH.sub.2).sub.4 3-chloro-2-fluorophenyl 204  C(CH.sub.2).sub.4 pentachlorophenyl 205  C(CH.sub.2).sub.4 2-bromophenyl 206  C(CH.sub.2).sub.4 3-bromophenyl 207  C(CH.sub.2).sub.4 4-bromophenyl 208  C(CH.sub.2).sub.4 2-fluoro-4-bromophenyl 209  C(CH.sub.2).sub.4 2-trifluoromethylphenyl 210  C(CH.sub.2).sub.4 3-trifluoromethylphenyl 211  C(CH.sub.2).sub.4 4-trifluoromethylphenyl 212  C(CH.sub.2).sub.4 2,4-bis(trifluoromethyl)phenyl 213  C(CH.sub.2).sub.4 3,5-bis(trifluoromethyl)phenyl 214  C(CH.sub.2).sub.4 2-methoxyphenyl 215  C(CH.sub.2).sub.4 3-methoxyphenyl 216  C(CH.sub.2).sub.4 4-methoxyphenyl 217  C(CH.sub.2).sub.4 3,4-dimethoxyphenyl 218  C(CH.sub.2).sub.4 3,4,5-trimethoxyphenyl 219  C(CH.sub.2).sub.4 4-ethoxyphenyl 220  C(CH.sub.2).sub.4 4-tetrafluoroethoxyphenyl 221  C(CH.sub.2).sub.4 4-trifluoromethoxyphenyl 222  C(CH.sub.2).sub.4 4-methoxyiminocarbyl-phenyl 223  C(CH.sub.2).sub.4 4-ethoxyiminocarbyl-phenyl 224  C(CH.sub.2).sub.4 4-methoxy-3-methylphenyl 225  C(CH.sub.2).sub.4 3-phenoxyphenyl 226  C(CH.sub.2).sub.4 4-phenoxyphenyl 227  C(CH.sub.2).sub.4 2-chloro-4-(4'-chloro- phenoxy)phenyl 228  C(CH.sub.2).sub.4 3-(4'-fluorophenoxy)- phenyl 229  C(CH.sub.2).sub.4 4-benzyloxyphenyl 230  C(CH.sub.2).sub.5 phenyl             mp. 117- 119 231  C(CH.sub.2).sub.5 2-methylphenyl 232  C(CH.sub.2).sub.5 3-methylphenyl 233  C(CH.sub.2).sub.5 4-methylphenyl 234  C(CH.sub.2).sub.5 2,3-dimethylphenyl 235  C(CH.sub.2).sub.5 2,4-dimethylphenyl 236  C(CH.sub.2).sub.5 2,5-dimethylphenyl 237  C(CH.sub.2).sub.5 2,6-dimethylphenyl 238  C(CH.sub.2).sub.5 3,4-dimethylphenyl 239  C(CH.sub.2).sub.5 3,5-dimethylphenyl 240  C(CH.sub.2).sub.5 2,4,5-trimethylphenyl 241  C(CH.sub.2).sub.5 2,4,6-trimethylphenyl 242  C(CH.sub.2).sub.5 2,3,5,6-tetramethylphenyl 243  C(CH.sub.2).sub.5 4-ethylphenyl 244  C(CH.sub.2).sub.5 4-isopropylphenyl 245  C(CH.sub.2).sub.5 4-tert.butylphenyl 246  C(CH.sub.2).sub.5 5-indanyl 247  C(CH.sub.2).sub.5 1-naphthyl 248  C(CH.sub.2).sub.5 2-naphthyl 249  C(CH.sub.2).sub.5 2-methyl-1-napthyl 250  C(CH.sub.2).sub.5 4-biphenyl 251  C(CH.sub.2).sub.5 2-fluorophenyl     mp. 146- 148 252  C(CH.sub.2).sub.5 3-fluorophenyl     mp. 132- 134 253  C(CH.sub.2).sub.5 4-fluorophenyl     mp. 126- 127 254  C(CH.sub.2).sub.5 2,3-difluorophenyl 255  C(CH.sub.2).sub.5 2,4-difluorophenyl 256  C(CH.sub.2).sub.5 2,5-difluorophenyl 257  C(CH.sub.2).sub.5 2,6-difluorophenyl 258  C(CH.sub.2).sub.5 3,4-difluorophenyl 259  C(CH.sub.2).sub.5 3,5-difluorophenyl 260  C(CH.sub.2).sub.5 2-fluoro-3-methylphenyl 261  C(CH.sub.2).sub.5 2,3,5,6-tetrafluorophenyl 262  C(CH.sub.2).sub.5 pentafluorophenyl 263  C(CH.sub.2).sub.5 2-chlorophenyl     mp. 162- 164 264  C(CH.sub.2).sub.5 3-chlorophenyl 265  C(CH.sub.2).sub.5 4-chlorophenyl     mp. 155- 156 266  C(CH.sub.2).sub.5 2,3-dichlorophenyl 267  C(CH.sub.2).sub.5 2,4-dichlorophenyl oil; N-oxide mp. 205- 207 268  C(CH.sub.2).sub.5 2,5-dichlorophenyl 269  C(CH.sub.2).sub.5 2,6-dichlorophenyl 270  C(CH.sub.2).sub.5 3,4-dichlorophenyl mp. 181- 183 271  C(CH.sub.2).sub.5 3,5-dichlorophenyl 272  C(CH.sub.2).sub.5 2,4,5-trichlorophenyl 273  C(CH.sub.2).sub.5 2,4,6-trichlorophenyl 274  C(CH.sub.2).sub.5 2,3,6-trichlorophenyl 275  C(CH.sub.2).sub.5 2-chloro-5-methylphenyl 276  C(CH.sub.2).sub.5 3-chloro-4-methylphenyl 277  C(CH.sub.2).sub.5 2-chloro-4-fluorophenyl 278  C(CH.sub.2).sub.5 2-chloro-6-fluorophenyl 279  C(CH.sub.2).sub.5 3-chloro-2-fluorophenyl 280  C(CH.sub.2).sub.5 pentachlorophenyl 281  C(CH.sub.2).sub.5 2-bromophenyl 282  C(CH.sub.2).sub.5 3-bromophenyl 283  C(CH.sub.2).sub.5 4-bromophenyl      mp. 190- 191 284  C(CH.sub.2).sub.5 2-fluoro-4-bromophenyl 285  C(CH.sub.2).sub.5 2-trifluoromethylphenyl 286  C(CH.sub.2).sub.5 3-trifluoromethylphenyl 287  C(CH.sub.2).sub.5 4-trifluoromethylphenyl 288  C(CH.sub.2).sub.5 2,4-bis(trifluoromethyl)phenyl 289  C(CH.sub.2).sub.5 3,5-bis(trifluoromethyl)phenyl 290  C(CH.sub.2).sub.5 2-methoxyphenyl 291  C(CH.sub.2).sub.5 3-methoxyphenyl 292  C(CH.sub.2).sub.5 4-methoxyphenyl 293  C(CH.sub.2).sub.5 3,4-dimethoxyphenyl 294  C(CH.sub.2).sub.5 3,4,5-trimethoxyphenyl 295  C(CH.sub.2).sub.5 4-ethoxyphenyl 296  C(CH.sub.2).sub.5 4-tetrafluoroethoxyphenyl 297  C(CH.sub.2).sub.5 4-trifluoromethoxyphenyl 298  C(CH.sub.2).sub.5 4-methoxyiminocarbyl-phenyl 299  C(CH.sub.2).sub.5 4-ethoxyiminocarbyl-phenyl 300  C(CH.sub.2).sub.5 4-methoxy-3-methylphenyl 301  C(CH.sub.2).sub.5 3-phenoxyphenyl 302  C(CH.sub.2).sub.5 4-phenoxyphenyl 303  C(CH.sub.2).sub.5 2-chloro-4-(4'-chloro- phenoxy)phenyl 304  C(CH.sub.2).sub.5 3-(4'-fluorophenoxy)- phenyl 305  C(CH.sub.2).sub.5 4-benzyloxyphenyl 306  C(CH.sub.3)nC.sub.3 H.sub.7 phenyl             oil; N-oxide mp. 154- 156 307  C(CH.sub.3)nC.sub.3 H.sub.7 2-methylphenyl 308  C(CH.sub.3)nC.sub.3 H.sub.7 3-methylphenyl 309  C(CH.sub.3)nC.sub.3 H.sub.7 4-methylphenyl 310  C(CH.sub.3)nC.sub.3 H.sub.7 2,3-dimethylphenyl 311  C(CH.sub.3)nC.sub.3 H.sub.7 2,4-dimethylphenyl 312  C(CH.sub.3)nC.sub.3 H.sub.7 2,5-dimethylphenyl 313  C(CH.sub.3)nC.sub.3 H.sub.7 2,6-dimethylphenyl 314  C(CH.sub.3)nC.sub.3 H.sub.7 3,4-dimethylphenyl 315  C(CH.sub.3)nC.sub.3 H.sub.7 3,5-dimethylphenyl 316  C(CH.sub.3)nC.sub.3 H.sub. 7 2,4,5-trimethylphenyl 317  C(CH.sub.3)nC.sub.3 H.sub.7 2,4,6-trimethylphenyl 318  C(CH.sub.3)nC.sub.3 H.sub.7 2,3,5,6-tetramethylphenyl 319  C(CH.sub.3)nC.sub.3 H.sub.7 4-ethylphenyl 320  C(CH.sub.3)nC.sub.3 H.sub.7 4-isopropylphenyl 321  C(CH.sub.3)nC.sub.3 H.sub.7 4-tert.butylphenyl 322  C(CH.sub.3)nC.sub.3 H.sub.7 5-indanyl 323  C(CH.sub.3)nC.sub.3 H.sub.7 1-naphthyl 324  C(CH.sub.3)nC.sub.3 H.sub.7 2-naphthyl 325  C(CH.sub.3)nC.sub.3 H.sub.7 2-methyl-1-naphthyl 326  C(CH.sub.3)nC.sub.3 H.sub.7 4-biphenyl 327  C(CH.sub.3)nC.sub.3 H.sub.7 2-fluorophenyl 328  C(CH.sub.3)nC.sub.3 H.sub.7 3-fluorophenyl 329  C(CH.sub.3)nC.sub.3 H.sub.7 4-fluorophenyl 330  C(CH.sub.3)nC.sub.3 H.sub.7 2,3-difluorophenyl 331  C(CH.sub.3)nC.sub.3 H.sub.7 2,4-difluorophenyl 332  C(CH.sub.3)nC.sub.3 H.sub.7 2,5-difluorophenyl 333  C(CH.sub.3)nC.sub.3 H.sub.7 2,6-difluorophenyl 334  C(CH.sub.3)nC.sub.3 H.sub.7 3,4-difluorophenyl 335  C(CH.sub.3)nC.sub.3 H.sub.7 3,5-difluorophenyl 336  C(CH.sub.3)nC.sub.3 H.sub.7 2-fluoro-3-methylphenyl 337  C(CH.sub.3)nC.sub.3 H.sub.7 2,3,5,6-tetrafluorophenyl 338  C(CH.sub.3)nC.sub.3 H.sub.7 pentafluorophenyl 339  C(CH.sub.3)nC.sub.3 H.sub.7 2-chlorophenyl 340  C(CH.sub.3)nC.sub.3 H.sub.7 3-chlorophenyl 341  C(CH.sub.3)nC.sub.3 H.sub. 7 4-chlorophenyl     oil; N-oxide: mp. 159- 160 342  C(CH.sub.3)nC.sub.3 H.sub.7 2,3-dichlorophenyl 343  C(CH.sub.3)nC.sub.3 H.sub.7 2,4-dichlorophenyl 344  C(CH.sub.3)nC.sub.3 H.sub.7 2,5-dichlorophenyl 345  C(CH.sub.3)nC.sub.3 H.sub.7 2,6-dichlorophenyl 346  C(CH.sub.3)nC.sub.3 H.sub.7 3,4-dichlorophenyl 347  C(CH.sub.3)nC.sub.3 H.sub.7 3,5-dichlorophenyl 348  C(CH.sub.3)nC.sub.3 H.sub.7 2,4,5-trichlorophenyl 349  C(CH.sub.3)nC.sub.3 H.sub.7 2,4,6-trichlorophenyl 350  C(CH.sub.3)nC.sub.3 H.sub.7 2,3,6-trichlorophenyl 351  C(CH.sub.3)nC.sub.3 H.sub.7 2-chloro-5-methylphenyl 352  C(CH.sub.3)nC.sub.3 H.sub.7 3-chloro-4-methylphenyl 353  C(CH.sub.3)nC.sub.3 H.sub.7 2-chloro-4-fluorophenyl 354  C(CH.sub.3)nC.sub.3 H.sub.7 2-chloro-6-fluorophenyl 355  C(CH.sub.3)nC.sub.3 H.sub.7 3-chloro-2-fluorophenyl 356  C(CH.sub.3)nC.sub.3 H.sub.7 pentachlorophenyl 357  C(CH.sub.3)nC.sub.3 H.sub.7 2-bromophenyl 358  C(CH.sub.3)nC.sub.3 H.sub.7 3-bromophenyl 359  C(CH.sub.3)nC.sub.3 H.sub.7 4-bromophenyl 360  C(CH.sub.3)nC.sub.3 H.sub.7 2-fluoro-4-bromophenyl 361  C(CH.sub.3)nC.sub.3 H.sub.7 2-trifluoromethylphenyl 362  C(CH.sub.3)nC.sub.3 H.sub.7 3-trifluoromethylphenyl 363  C(CH.sub.3)nC.sub.3 H.sub.7 4-trifluoromethylphenyl 364  C(CH.sub.3)nC.sub.3 H.sub.7 2,4-bis(trifluoromethyl)phenyl 365  C(CH.sub.3)nC.sub.3 H.sub.7 3,5-bis(trifluoromethyl)phenyl 366  C(CH.sub.3)nC.sub.3 H.sub.7 2-methoxyphenyl 367  C(CH.sub.3)nC.sub.3 H.sub.7 3-methoxyphenyl 368  C(CH.sub.3)nC.sub.3 H.sub.7 4-methoxyphenyl 369  C(CH.sub.3)nC.sub.3 H.sub.7 3,4-dimethoxyphenyl 370  C(CH.sub.3)nC.sub.3 H.sub.7 3,4,5-trimethoxyphenyl 371  C(CH.sub.3)nC.sub.3 H.sub.7 4-ethoxyphenyl 372  C(CH.sub.3)nC.sub.3 H.sub.7 4-tetrafluoroethoxyphenyl 373  C(CH.sub.3)nC.sub.3 H.sub.7 4-trifluoromethoxyphenyl 374  C(CH.sub.3)nC.sub.3 H.sub.7 4-methoxyiminocarbyl-phenyl 375  C(CH.sub.3)nC.sub.3 H.sub.7 4-ethoxyiminocarbyl-phenyl 376  C(CH.sub.3)nC.sub.3 H.sub.7 4-methoxy-3-methylphenyl 377  C(CH.sub.3)nC.sub.3 H.sub.7 3-phenoxyphenyl 378  C(CH.sub.3)nC.sub.3 H.sub.7 4-phenoxyphenyl 379  C(CH.sub.3)nC.sub.3 H.sub.7 2-chloro-4-(4'-chloro- phenoxy)phenyl 380  C(CH.sub.3)nC.sub.3 H.sub.7 3-(4'-fluorophenoxy)- phenyl 381  C(CH.sub.3)nC.sub.3 H.sub.7 4-benzyloxyphenyl 382  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 phenyl             oil 383  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-methylphenyl 384  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-methylphenyl 385  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-methylphenyl 386  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3-dimethylphenyl 387  C(C.sub.2 H.sub. 5)nC.sub.4 H.sub.9 2,4-dimethylphenyl 388  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,5-dimethylphenyl 389  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,6-dimethylphenyl 390  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4-dimethylphenyl 391  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,5-dimethylphenyl 392  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4,5-trimethylphenyl 393  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4,6-trimethylphenyl 394  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3,5,6-tetramethylphenyl 395  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-ethylphenyl 396  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-isopropylphenyl 397  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-tert.butylphenyl 398  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 5-indanyl 399  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 1-naphthyl 400  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-naphthyl 401  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-methyl-1-napthyl 402  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-biphenyl 403  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-fluorophenyl 404  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-fluorophenyl 405  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-fluorophenyl 406  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3-difluorophenyl 407  C(C.sub.2 H.sub. 5)nC.sub.4 H.sub.9 2,4-difluorophenyl 408  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,5-difluorophenyl 409  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,6-difluorophenyl 410  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4-difluorophenyl 411  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,5-difluorophenyl 412  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-fluoro-3-methylphenyl 413  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3,5,6-tetrafluorophenyl 414  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 pentafluorophenyl 415  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-chlorophenyl 416  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-chlorophenyl 417  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-chlorophenyl 418  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3-dichlorophenyl 419  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4-dichlorophenyl 420  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,5-dichlorophenyl 421  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,6-dichlorophenyl 422  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4-dichlorophenyl 423  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,5-dichlorophenyl 424  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4,5-trichlorophenyl 425  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4,6-trichlorophenyl 426  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3,6-trichlorophenyl 427  C(C.sub.2 H.sub. 5)nC.sub.4 H.sub.9 2-chloro-5-methylphenyl 428  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-chloro-4-methylphenyl 429  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-chloro-4-fluorophenyl 430  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-chloro-6-fluorophenyl 431  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-chloro-2-fluorophenyl 432  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 pentachlorophenyl 433  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-bromophenyl 434  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-bromophenyl 435  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-bromophenyl 436  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-fluoro-4-bromophenyl 437  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-trifluoromethylphenyl 438  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-trifluoromethylphenyl 439  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-trifluoromethylphenyl 440  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4-bis(trifluoromethyl)phenyl 441  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,5-bis(trifluoromethyl)phenyl 442  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-methoxyphenyl 443  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-methoxyphenyl 444  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-methoxyphenyl 445  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4-dimethoxyphenyl 446  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4,5-trimethoxyphenyl 447  C(C.sub.2 H.sub. 5)nC.sub.4 H.sub.9 4-ethoxyphenyl 448  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-tetrafluoroethoxyphenyl 449  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-trifluoromethoxyphenyl 450  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-methoxyiminocarbyl-phenyl 451  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-ethoxyiminocarbyl-phenyl 452  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-methoxy-3-methylphenyl 453  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-phenoxyphenyl 454  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-phenoxyphenyl 455  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-chloro-4-(4'-chloro- phenoxy)phenyl 456  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-(4'-fluorophenoxy)- phenyl 457  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-benzyloxyphenyl 458  C(CH.sub.2).sub.3 OCH.sub.2 phenyl 459  C(CH.sub.2).sub.3 OCH.sub.2 2-methylphenyl 460  C(CH.sub.2).sub.3 OCH.sub.2 3-methylphenyl 461  C(CH.sub.2).sub.3 OCH.sub.2 4-methylphenyl 462  C(CH.sub.2).sub.3 OCH.sub.2 2,3-dimethylphenyl 463  C(CH.sub.2).sub.3 OCH.sub.2 2,4-dimethylphenyl 464  C(CH.sub.2).sub.3 OCH.sub.2 2,5-dimethylphenyl 465  C(CH.sub.2).sub.3 OCH.sub.2 2,6-dimethylphenyl 466  C(CH.sub.2).sub.3 OCH.sub.2 3,4-dimethylphenyl 467  C(CH.sub.2).sub.3 OCH.sub.2 3,5-dimethylphenyl 468  C(CH.sub.2).sub.3 OCH.sub. 2 2,4,5-trimethylphenyl 469  C(CH.sub.2).sub.3 OCH.sub.2 2,4,6-trimethylphenyl 470  C(CH.sub.2).sub.3 OCH.sub.2 2,3,5,6-tetramethylphenyl 471  C(CH.sub.2).sub.3 OCH.sub.2 4-ethylphenyl 472  C(CH.sub.2).sub.3 OCH.sub.2 4-isopropylphenyl 473  C(CH.sub.2).sub.3 OCH.sub.2 4-tert.butylphenyl 474  C(CH.sub.2).sub.3 OCH.sub.2 5-indanyl 475  C(CH.sub.2).sub.3 OCH.sub.2 1-naphthyl 476  C(CH.sub.2).sub.3 OCH.sub.2 2-naphthyl 477  C(CH.sub.2).sub.3 OCH.sub.2 2-methyl-1-naphthyl 478  C(CH.sub.2).sub.3 OCH.sub.2 4-biphenyl 479  C(CH.sub.2).sub.3 OCH.sub.2 2-fluorophenyl 480  C(CH.sub.2).sub.3 OCH.sub.2 3-fluorophenyl 481  C(CH.sub.2).sub.3 OCH.sub.2 4-fluorophenyl 482  C(CH.sub.2).sub.3 OCH.sub.2 2,3-difluorophenyl 483  C(CH.sub.2).sub.3 OCH.sub.2 2,4-difluorophenyl 484  C(CH.sub.2).sub.3 OCH.sub.2 2,5-difluorophenyl 485  C(CH.sub.2).sub.3 OCH.sub.2 2,6-difluorophenyl 486  C(CH.sub.2).sub.3 OCH.sub.2 3,4-difluorophenyl 487  C(CH.sub.2).sub.3 OCH.sub.2 3,5-difluorophenyl 488  C(CH.sub.2).sub.3 OCH.sub.2 2-fluoro-3-methylphenyl 489  C(CH.sub.2).sub.3 OCH.sub.2 2,3,5,6-tetrafluorophenyl 490  C(CH.sub.2).sub.3 OCH.sub.2 pentafluorophenyl 491  C(CH.sub.2).sub.3 OCH.sub.2 2-chlorophenyl 492  C(CH.sub.2).sub.3 OCH.sub.2 3-chlorophenyl 493  C(CH.sub.2).sub.3 OCH.sub. 2 4-chlorophenyl 494  C(CH.sub.2).sub.3 OCH.sub.2 2,3-dichlorophenyl 495  C(CH.sub.2).sub.3 OCH.sub.2 2,4-dichlorophenyl 496  C(CH.sub.2).sub.3 OCH.sub.2 2,5-dichlorophenyl 497  C(CH.sub.2).sub.3 OCH.sub.2 2,6-dichlorophenyl 498  C(CH.sub.2).sub.3 OCH.sub.2 3,4-dichlorophenyl 499  C(CH.sub.2).sub.3 OCH.sub.2 3,5-dichlorophenyl 500  C(CH.sub.2).sub.3 OCH.sub.2 2,4,5-trichlorophenyl 501  C(CH.sub.2).sub.3 OCH.sub.2 2,4,6-trichlorophenyl 502  C(CH.sub.2).sub.3 OCH.sub.2 2,3,6-trichlorophenyl 503  C(CH.sub.2).sub.3 OCH.sub.2 2-chloro-5-methylphenyl 504  C(CH.sub.2).sub.3 OCH.sub.2 3-chloro-4-methylphenyl 505  C(CH.sub.2).sub.3 OCH.sub.2 2-chloro-4-fluorophenyl 506  C(CH.sub.2).sub.3 OCH.sub.2 2-chloro-6-fluorophenyl 507  C(CH.sub.2).sub.3 OCH.sub.2 3-chloro-2-fluorophenyl 508  C(CH.sub.2).sub.3 OCH.sub.2 pentachlorophenyl 509  C(CH.sub.2).sub.3 OCH.sub.2 2-bromophenyl 510  C(CH.sub.2).sub.3 OCH.sub.2 3-bromophenyl 511  C(CH.sub.2).sub.3 OCH.sub.2 4-bromophenyl 512  C(CH.sub.2).sub.3 OCH.sub.2 2-fluoro-4-bromophenyl 513  C(CH.sub.2).sub.3 OCH.sub.2 2-trifluoromethylphenyl 514  C(CH.sub.2).sub.3 OCH.sub.2 3-trifluoromethylphenyl 515  C(CH.sub.2).sub.3 OCH.sub.2 4-trifluoromethylphenyl 516  C(CH.sub.2).sub.3 OCH.sub.2 2,4-bis(trifluoromethyl)phenyl 517  C(CH.sub.2).sub.3 OCH.sub.2 3,5-bis(trifluoromethyl)phenyl 518  C(CH.sub.2).sub.3 OCH.sub. 2 2-methoxyphenyl 519  C(CH.sub.2).sub.3 OCH.sub.2 3-methoxyphenyl 520  C(CH.sub.2).sub.3 OCH.sub.2 4-methoxyphenyl 521  C(CH.sub.2).sub.3 OCH.sub.2 3,4-dimethoxyphenyl 522  C(CH.sub.2).sub.3 OCH.sub.2 3,4,5-trimethoxyphenyl 523  C(CH.sub.2).sub.3 OCH.sub.2 4-ethoxyphenyl 524  C(CH.sub.2).sub.3 OCH.sub.2 4-tetrafluoroethoxyphenyl 525  C(CH.sub.2).sub.3 OCH.sub.2 4-trifluoromethoxyphenyl 526  C(CH.sub.2).sub.3 OCH.sub.2 4-methoxyiminocarbyl-phenyl 527  C(CH.sub.2).sub.3 OCH.sub.2 4-ethoxyiminocarbyl-phenyl 528  C(CH.sub.2).sub.3 OCH.sub.2 4-methoxy-3-methylphenyl 529  C(CH.sub.2).sub.3 OCH.sub.2 3-phenoxyphenyl 530  C(CH.sub.2).sub.3 OCH.sub.2 4-phenoxyphenyl 531  C(CH.sub.2).sub.3 OCH.sub.2 2-chloro-4-(4'-chloro- phenoxy)phenyl 532  C(CH.sub.2).sub.3 OCH.sub.2 3-(4'-fluorophenoxy)- phenyl 533  C(CH.sub.2).sub.3 OCH.sub.2 4-benzyloxyphenyl 534  C(CH.sub.2).sub.2 phenyl 535  C(CH.sub.2).sub.2 2-methylphenyl 536  C(CH.sub.2).sub.2 3-methylphenyl 537  C(CH.sub.2).sub.2 4-methylphenyl 538  C(CH.sub.2).sub.2 2,3-dimethylphenyl 539  C(CH.sub.2).sub.2 2,4-dimethylphenyl 540  C(CH.sub.2).sub.2 2,5-dimethylphenyl 541  C(CH.sub.2).sub.2 2,6-dimethylphenyl 542  C(CH.sub.2).sub.2 3,4-dimethylphenyl 543  C(CH.sub.2).sub.2 3,5-dimethylphenyl 544  C(CH.sub.2).sub.2 2,4,5-trimethylphenyl 545  C(CH.sub.2).sub. 2 2,4,6-trimethylphenyl 546  C(CH.sub.2).sub.2 2,3,5,6-tetramethylphenyl 547  C(CH.sub.2).sub.2 4-ethylphenyl 548  C(CH.sub.2).sub.2 4-isopropylphenyl 549  C(CH.sub.2).sub.2 4-tert.butylphenyl 550  C(CH.sub.2).sub.2 5-indanyl 551  C(CH.sub.2).sub.2 1-naphthyl 552  C(CH.sub.2).sub.2 2-naphthyl 553  C(CH.sub.2).sub.2 2-methyl-1-napthyl 554  C(CH.sub.2).sub.2 4-biphenyl 555  C(CH.sub.2).sub.2 2-fluorophenyl 556  C(CH.sub.2).sub.2 3-fluorophenyl 557  C(CH.sub.2).sub.2 4-fluorophenyl 558  C(CH.sub.2).sub.2 2,3-difluorophenyl 559  C(CH.sub.2).sub.2 2,4-difluorophenyl 560  C(CH.sub.2).sub.2 2,5-difluorophenyl 561  C(CH.sub.2).sub.2 2,6-difluorophenyl 562  C(CH.sub.2).sub.2 3,4-difluorophenyl 563  C(CH.sub.2).sub.2 3,5-difluorophenyl 564  C(CH.sub.2).sub.2 2-fluoro-3-methylphenyl 565  C(CH.sub.2).sub.2 2,3,5,6-tetrafluorophenyl 566  C(CH.sub.2).sub.2 pentafluorophenyl 567  C(CH.sub.2).sub.2 2-chlorophenyl 568  C(CH.sub.2).sub.2 3-chlorophenyl 569  C(CH.sub.2).sub.2 4-chlorophenyl 570  C(CH.sub.2).sub.2 2,3-dichlorophenyl 571  C(CH.sub.2).sub.2 2,4-dichlorophenyl 572  C(CH.sub.2).sub.2 2,5-dichlorophenyl 573  C(CH.sub.2).sub.2 2,6-dichlorophenyl 574  C(CH.sub.2).sub.2 3,4-dichlorophenyl 575  C(CH.sub.2).sub.2 3,5-dichlorophenyl 576  C(CH.sub.2).sub.2 2,4,5-trichlorophenyl 577  C(CH.sub.2).sub.2 2,4,6-trichlorophenyl 578  C(CH.sub.2).sub.2 2,3,6-trichlorophenyl 579  C(CH.sub.2).sub.2 2-chloro-5-methylphenyl 580  C(CH.sub.2).sub.2 3-chloro-4-methylphenyl 581  C(CH.sub.2).sub.2 2-chloro-4-fluorophenyl 582  C(CH.sub.2).sub.2 2-chloro-6-fluorophenyl 583  C(CH.sub.2).sub.2 3-chloro-2-fluorophenyl 584  C(CH.sub.2).sub.2 pentachlorophenyl 585  C(CH.sub.2).sub.2 2-bromophenyl 586  C(CH.sub.2).sub.2 3-bromophenyl 587  C(CH.sub.2).sub.2 4-bromophenyl 588  C(CH.sub.2).sub.2 2-fluoro-4-bromophenyl 589  C(CH.sub.2).sub.2 2-trifluoromethylphenyl 590  C(CH.sub.2).sub.2 3-trifluoromethylphenyl 591  C(CH.sub.2).sub.2 4-trifluoromethylphenyl 592  C(CH.sub.2).sub.2 2,4-bis(trifluoromethyl)phenyl 593  C(CH.sub.2).sub.2 3,5-bis(trifluoromethyl)phenyl 594  C(CH.sub.2).sub.2 2-methoxyphenyl 595  C(CH.sub.2).sub.2 3-methoxyphenyl 596  C(CH.sub.2).sub.2 4-methoxyphenyl 597  C(CH.sub.2).sub.2 3,4-dimethoxyphenyl 598  C(CH.sub.2).sub.2 3,4,5-trimethoxyphenyl 599  C(CH.sub.2).sub.2 4-ethoxyphenyl 600  C(CH.sub.2).sub.2 4-tetrafluoroethoxyphenyl 601  C(CH.sub.2).sub.2 4-trifluoromethoxyphenyl 602  C(CH.sub.2).sub.2 4-methoxyiminocarbyl-phenyl 603  C(CH.sub.2).sub.2 4-ethoxyiminocarbyl-phenyl 604  C(CH.sub.2).sub.2 4-methoxy-3-methylphenyl 605  C(CH.sub.2).sub.2 3-phenoxyphenyl 606  C(CH.sub.2).sub.2 4-phenoxyphenyl 607  C(CH.sub.2).sub.2 2-chloro-4-(4'-chloro- phenoxy)phenyl 608  C(CH.sub.2).sub.2 3-(4'-fluorophenoxy)- phenyl 609  C(CH.sub.2).sub.2 4-benzyloxyphenyl ______________________________________ ______________________________________ ##STR12## Ex. no.  R.sup.2 A           Ar          Physical data ______________________________________ 610  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 phenyl      oil 611  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-chlorophenyl oil 612  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-fluorophenyl oil 613  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 2,4-dichlorophenyl oil 614  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 2-methylphenyl 615  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-methylphenyl 616  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-tert.-butylphenyl 617  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 2-naphthyl 618  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 2-fluorophenyl 619  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-bromophenyl 620  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 3-fluorophenyl 621  CH.sub.3 C(C.sub.2 H.sub.5).sub.2 3,4-dichlorophenyl 622  CH.sub.3 C(CH.sub.2).sub.5 phenyl 623  CH.sub.3 C(CH.sub.2).sub.5 2-methylphenyl 624  CH.sub.3 C(CH.sub.2 ).sub.5 4-methylphenyl 625  CH.sub.3 C(CH.sub.2).sub.5 4-tert.-butylphenyl 626  CH.sub.3 C(CH.sub.2).sub.5 2-naphthyl 627  CH.sub.3 C(CH.sub.2).sub.5 2-fluorophenyl 628  CH.sub.3 C(CH.sub.2).sub.5 3-fluorophenyl 629  CH.sub.3 C(CH.sub.2).sub.5 4-fluorophenyl 630  CH.sub.3 C(CH.sub.2).sub.5 4-bromophenyl 631  CH.sub.3 C(CH.sub.2).sub.5 4-chlorophenyl 632  CH.sub.3 C(CH.sub.2).sub.5 2-chlorophenyl 633  CH.sub.3 C(CH.sub.2).sub.5 2,4-dichlorophenyl 634  CH.sub.3 C(CH.sub.2).sub.5 3,4-dichlorophenyl 635  CH.sub.3 C(CH.sub.2).sub.4 phenyl 636  CH.sub.3 C(CH.sub.2).sub.4 2-methylphenyl 637  CH.sub.3 C(CH.sub.2).sub.4 4-methylphenyl 638  CH.sub.3 C(CH.sub.2).sub.4 4-tert.-butylphenyl 639  CH.sub.3 C(CH.sub.2).sub.4 2-naphthyl 640  CH.sub.3 C(CH.sub.2).sub.4 2-fluorophenyl 641  CH.sub.3 C(CH.sub.2).sub.4 3-fluorophenyl 642  CH.sub.3 C(CH.sub.2).sub.4 4-fluorophenyl 643  CH.sub.3 C(CH.sub.2).sub.4 4-bromophenyl 644  CH.sub.3 C(CH.sub.2).sub.4 4-chlorophenyl 645  CH.sub.3 C(CH.sub.2).sub.4 2-chlorophenyl 646  CH.sub.3 C(CH.sub.2).sub.4 2,4-dichlorophenyl 647  CH.sub.3 C(CH.sub.2).sub.4 3,4-dichlorophenyl 648  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 phenyl 649  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 2-methylphenyl 650  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-methylphenyl 651  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-tert.-butylphenyl 652  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 2-naphthyl 653  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 2-fluorophenyl 654  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 3-fluorophenyl 655  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-fluorophenyl 656  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-bromophenyl 657  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-chlorophenyl 658  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 2,4-dichlorophenyl 659  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 3,4-dichlorophenyl 660  CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-biphenyl ______________________________________

Generally speaking, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the Ascomycetes and Basidiomycetes classes. 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, oats, 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 Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia species in cotton and lawns,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in vegetables and fruit.

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, materials or soil to be protected against fungus attack 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, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin, sulfite waste liquors and methylcellulose.

The fungicidal agents 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 (wood), for example against Paecilomyces variotii.

When the active ingredients are used for treating seed, amounts of from 0.001 to 50, and preferably from 0.01 to 10, g are generally used per kg of seed.

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. 90 parts by weight of compound no. 230 (Table 1) is mixed with 10 parts by weight of N-methyl-.alpha.-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 306 (Table 1) is dissolved in a mixture consisting of 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 pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.

III. 20 parts by weight of compound no. 341 is dissolved in a mixture consisting of 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 pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained.

IV. 20 parts by weight of compound no. 382 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210.degree. 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 uniformly distributing it therein, an aqueous dispersion is obtained.

V. 80 parts by weight of compound no. 175 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-.alpha.-sulfonic acid, 10 parts 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, and triturated in a hammer mill. By uniformly distributing the mixture in water, a spray liquor is obtained.

VI. 3 parts by weight of compound no. 187 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

VII. 30 parts by weight of compound no. 191 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 40 parts by weight of compound no. 253 is intimately mixed with 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion. Dilution in water gives an aqueous dispersion.

IX. 20 parts by weight of compound no. 267 is intimately mixed with 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. A stable oily dispersion is obtained.

For comparison purposes, the compound 3-phenyl-2,2-dimethyl-1-(3-pyridyl)propan-1-ol (A) disclosed in EP 302,365 was used.

Pimiento seedlings of the "Neusiedler Ideal Elite" variety with 4 to 5 well developed leaves were sprayed to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were sprayed with a conidial suspension of the fungus Botrytis cinerea and kept in a high-humidity chamber at 22.degree. to 24.degree. C. After 5 days, the disease had spread on the untreated control plants to such an extent that the necroses covered the major portion of the leaves. The leaf attack was assessed.

The results show that active ingredients 230, 306, 341 and 382, applied as 0.05% spray liquors, have a better fungicidal action (90%) than prior art active ingredient A (55%).

Barley seedlings of the "Igri" variety were sprayed to runoff at the two-leaf stage with aqueous suspensions consisting (dry basis) of 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 for 48 hours in a high-humidity climatic cabinet at 18.degree. C. The plants were then cultivated for a further 5 days in the greenhouse at 20.degree. to 22.degree. C. and a relative humidity of 70.degree. C. The extent of fungus spread was then assessed.

The results show that active ingredients 175, 187, 191, 253, 267, 306, 341 and 382, applied as 0.025% spray liquors, have a better fungicidal action (98%) than prior art active ingredient A (60%).

## Claims

1. A pyridine compound having the following formula: ##STR13## where R.sup.1 is hydrogen or an acyl radical --COR.sup.2 ; R.sup.2 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl or substituted or unsubstituted aryl; A is one of the groups ##STR14## where R.sup.3 and R.sup.4 are identical or differ and each is C.sub.1 -C.sub.6 -alkyl, with the proviso that R.sup.3 and R.sup.4 are not simultaneously methyl; R.sup.5 is one of the groups (CH.sub.2).sub.n, CH.sub.2 OCH.sub.2, CH.sub.2 S(O).sub.m CH.sub.2, CH.sub.2 CH.sub.2 O or CH.sub.2 CH.sub.2 S(O).sub.m, n denoting 1, 2, 3, 4 or 5, and m being 0, 1 or 2; Ar is phenyl, indanyl, 1-naphthyl, 2-naphthyl, 2-methyl-1-naphthyl or phenyl substituted by one to five substituents selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, phenyl, halogen, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, or the N-oxide or plant-tolerated acid addition salt thereof.

2. A fungicidal composition containing a carrier and a fungicidally effective amount of a pyridine compound of the formula ##STR15## where R.sup.1 is hydrogen or an acyl radical --COR.sup.2 ; R.sup.2 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl or substituted or unsubstituted aryl; A is one of the groups ##STR16## where R.sup.3 and R.sup.4 are identical or differ and each is C.sub.1 -C.sub.6 -alkyl, with the proviso that R.sup.3 and R.sup.4 are not simultaneously methyl; R.sup.5 is one of the groups (CH.sub.2).sub.n, CH.sub.2 OCH.sub.2, CH.sub.2 S(O).sub.m CH.sub.2, CH.sub.2 CH.sub.2 O or CH.sub.2 CH.sub.2 S(O).sub.m, n denoting 1, 2, 3, 4 or 5, and m being 0, 1 or 2; Ar is phenyl, indanyl, 1-naphthyl, 2-naphthyl, 2-methyl-1-naphthyl or phenyl substituted by one to five substituents selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, phenyl, halogen, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, or the N-oxide or plant-tolerated acid addition salt thereof.

3. A process for combating fungi, wherein the fungi, or the materials, plants, soils or seed threatened by fungus attack are treated with a fungicidally effective amount of a pyridine compound of the formula ##STR17## where R.sup.1 is hydrogen or an acyl radical --COR.sup.2 ; R.sup.2 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl or substituted or unsubstituted aryl; A is one of the groups ##STR18## where R.sup.3 and R.sup.4 are identical or differ and each is C.sub.1 -C.sub.6 -alkyl, with the proviso that R.sup.3 and R.sup.4 are not simultaneously methyl; R.sup.5 is one of the groups (CH.sub.2).sub.n, CH.sub.2 OCH.sub.2, CH.sub.2 S(O).sub.m CH.sub.2, CH.sub.2 CH.sub.2 O or CH.sub.2 CH.sub.2 S(O).sub.m, n denoting 1, 2, 3, 4 or 5, and m being 0, 1 or 2; Ar is phenyl, indanyl, 1-naphthyl, 2-naphthyl, 2-methyl-1-naphthyl or phenyl substituted by one to five substituents selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, phenyl, halogen, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, or the N-oxide or plant-tolerated acid addition salt thereof.