Pyridine compounds which are useful as fungicides

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 ;
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 ##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;
R.sup.5 is (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, CH.sub.2 CH.sub.2 S(O).sub.m where
n is an integer from 1 to 5 and
m is an integer from 0 to 2;
Ar is aryl which carries 0-5 substituents from the group comprising 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 -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-butyphenyl, 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, biphenylyl, 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
R.sup.1 is hydrogen, methyl, ethyl, tert-butyl, allyl, propargyl or COR.sup.2,
R.sup.2 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl or substituted or unsubstituted phenyl,
A is ##STR5## R.sup.3 and R.sup.4 are, independently of one another, methyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl,
R.sup.5 is ethylene or 1,3-propylene, and Ar has the meanings specified in 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
Ar--CH.sub.2 --A--CHO 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, eg. 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, eg. 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.

EXAMPLE 1
2-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)butyl acetate (compound no. 611)
10.2 g (0.10 mol) of acetic anhydride are added dropwise to a solution of 12.1 g (0.04 mol) of 2-(4chlorobenzyl)-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).
EXAMPLE 2
2-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol (compound no. 113)
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.
Preparation of the starting compound 2-(4-Chlorobenzyl)-2-ethylbutanal
300 ml of toluene, 400 ml of 30 percent (by weight) sodium hydroxide solution and 5.0 g of tetra-n-butylammonium 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:
TABLE 1______________________________________ ##STR11## PhysicalEx. no. A Ar data______________________________________1 C(CH.sub.3)C.sub.2 H.sub.5 phenyl2 C(CH.sub.3)C.sub.2 H.sub.5 2-methylphenyl3 C(CH.sub.3)C.sub.2 H.sub.5 3-methylphenyl4 C(CH.sub.3)C.sub.2 H.sub.5 4-methylphenyl5 C(CH.sub.3)C.sub.2 H.sub.5 2,3-dimethylphenyl6 C(CH.sub.3)C.sub.2 H.sub.5 2,4-dimethylphenyl7 C(CH.sub.3)C.sub.2 H.sub.5 2,5-dimethylphenyl8 C(CH.sub.3)C.sub.2 H.sub.5 2,6-dimethylphenyl9 C(CH.sub.3)C.sub.2 H.sub.5 3,4-dimethylphenyl10 C(CH.sub.3)C.sub.2 H.sub.5 3,5-dimethylphenyl11 C(CH.sub.3)C.sub.2 H.sub.5 2,4,5-trimethylphenyl12 C(CH.sub.3)C.sub.2 H.sub.5 2,4,6-trimethylphenyl13 C(CH.sub.3)C.sub.2 H.sub.5 2,3,5,6-tetramethylphenyl14 C(CH.sub.3)C.sub.2 H.sub.5 4-ethylphenyl15 C(CH.sub.3)C.sub.2 H.sub.5 4-isopropylphenyl16 C(CH.sub.3)C.sub.2 H.sub.5 4-tert.butylphenyl17 C(CH.sub.3)C.sub.2 H.sub.5 5-indanyl18 C(CH.sub.3)C.sub.2 H.sub.5 1-naphthyl19 C(CH.sub.3)C.sub.2 H.sub.5 2-naphthyl20 C(CH.sub.3)C.sub.2 H.sub.5 2-methyl-1-naphthyl21 C(CH.sub.3)C.sub.2 H.sub.5 4-biphenyl22 C(CH.sub.3)C.sub.2 H.sub.5 2-fluorophenyl23 C(CH.sub.3)C.sub.2 H.sub.5 3-fluorophenyl24 C(CH.sub.3)C.sub.2 H.sub.5 4-fluorophenyl25 C(CH.sub.3)C.sub.2 H.sub.5 2,3-difluorophenyl26 C(CH.sub.3)C.sub.2 H.sub.5 2,4-difluorophenyl27 C(CH.sub.3)C.sub.2 H.sub.5 2,5-difluorophenyl28 C(CH.sub.3)C.sub.2 H.sub.5 2,6-difluorophenyl29 C(CH.sub.3)C.sub.2 H.sub.5 3,4-difluorophenyl30 C(CH.sub.3)C.sub.2 H.sub.5 3,5-difluorophenyl31 C(CH.sub.3)C.sub.2 H.sub.5 2-fluoro-3-methylphenyl32 C(CH.sub.3)C.sub.2 H.sub.5 2,3,5,6-tetrafluorophenyl33 C(CH.sub.3)C.sub.2 H.sub.5 pentafluorophenyl34 C(CH.sub.3)C.sub.2 H.sub.5 2-chlorophenyl35 C(CH.sub.3)C.sub.2 H.sub.5 3-chlorophenyl36 C(CH.sub.3)C.sub.2 H.sub.5 4-chlorophenyl37 C(CH.sub.3)C.sub.2 H.sub.5 2,3-dichlorophenyl38 C(CH.sub.3)C.sub.2 H.sub.5 2,4-dichlorophenyl39 C(CH.sub.3)C.sub.2 H.sub.5 2,5-dichlorophenyl40 C(CH.sub.3)C.sub.2 H.sub.5 2,6-dichlorophenyl41 C(CH.sub.3)C.sub.2 H.sub.5 3,4-dichlorophenyl42 C(CH.sub.3)C.sub.2 H.sub.5 3,5-dichlorophenyl43 C(CH.sub.3)C.sub.2 H.sub.5 2,4,5-trichlorophenyl44 C(CH.sub.3)C.sub.2 H.sub.5 2,4,6-trichlorophenyl45 C(CH.sub.3)C.sub.2 H.sub.5 2,3,6-trichlorophenyl46 C(CH.sub.3)C.sub.2 H.sub.5 2-chloro-5-methylphenyl47 C(CH.sub.3)C.sub.2 H.sub.5 3-chloro-4-methylphenyl48 C(CH.sub.3)C.sub.2 H.sub.5 2-chloro-4-fluorophenyl49 C(CH.sub.3)C.sub.2 H.sub.5 2-chloro-6-fluorophenyl50 C(CH.sub.3)C.sub.2 H.sub.5 3-chloro-2-fluorophenyl51 C(CH.sub.3)C.sub.2 H.sub.5 pentachlorophenyl52 C(CH.sub.3)C.sub.2 H.sub.5 2-bromophenyl53 C(CH.sub.3)C.sub.2 H.sub.5 3-bromophenyl54 C(CH.sub.3)C.sub.2 H.sub.5 4-bromophenyl55 C(CH.sub.3)C.sub.2 H.sub.5 2-fluoro-4-bromophenyl56 C(CH.sub.3)C.sub.2 H.sub.5 2-trifluoromethylphenyl57 C(CH.sub.3)C.sub.2 H.sub.5 3-trifluoromethylphenyl58 C(CH.sub.3)C.sub.2 H.sub.5 4-trifluoromethylphenyl59 C(CH.sub.3)C.sub.2 H.sub.5 2,4-bis(trifluoromethyl)- phenyl60 C(CH.sub.3)C.sub.2 H.sub.5 3,5-bis(trifluoromethyl)- phenyl61 C(CH.sub.3)C.sub.2 H.sub.5 2-methoxyphenyl62 C(CH.sub.3)C.sub.2 H.sub.5 3-methoxyphenyl63 C(CH.sub.3)C.sub.2 H.sub.5 4-methoxyphenyl64 C(CH.sub.3)C.sub.2 H.sub.5 3,4-dimethoxyphenyl65 C(CH.sub.3)C.sub.2 H.sub.5 3,4,5-trimethoxyphenyl66 C(CH.sub.3)C.sub.2 H.sub.5 4-ethoxyphenyl67 C(CH.sub.3)C.sub.2 H.sub.5 4-tetrafluoroethoxyphenyl68 C(CH.sub.3)C.sub.2 H.sub.5 4-trifluoromethoxyphenyl69 C(CH.sub.3)C.sub.2 H.sub.5 4-methoxyiminocarbyl-phenyl70 C(CH.sub.3)C.sub.2 H.sub.5 4-ethoxyiminocarbyl-phenyl71 C(CH.sub.3)C.sub.2 H.sub.5 4-methoxy-3-methylphenyl72 C(CH.sub.3)C.sub.2 H.sub.5 3-phenoxyphenyl73 C(CH.sub.3)C.sub.2 H.sub.5 4-phenoxyphenyl74 C(CH.sub.3)C.sub.2 H.sub.5 2-chloro-4-(4'-chloro- phenoxy)phenyl75 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)- phenyl77 C(CH.sub.3)C.sub.2 H.sub.5 4-benzyloxyphenyl78 C(C.sub.2 H.sub.5).sub.2 phenyl mp. 130- 13279 C(C.sub.2 H.sub.5).sub.2 2-methylphenyl mp. 92- 9480 C(C.sub.2 H.sub.5).sub.2 3-methylphenyl81 C(C.sub.2 H.sub.5).sub.2 4-methylphenyl mp. 87- 8882 C(C.sub.2 H.sub.5).sub.2 2,3-dimethylphenyl83 C(C.sub.2 H.sub.5).sub.2 2,4-dimethylphenyl84 C(C.sub.2 H.sub.5).sub.2 2,5-dimethylphenyl85 C(C.sub.2 H.sub.5).sub.2 2,6-dimethylphenyl86 C(C.sub.2 H.sub.5).sub.2 3,4-dimethylphenyl87 C(C.sub.2 H.sub.5).sub.2 3,5-dimethylphenyl88 C(C.sub.2 H.sub.5).sub.2 2,4,5-trimethylphenyl89 C(C.sub.2 H.sub.5).sub.2 2,4,6-trimethylphenyl90 C(C.sub.2 H.sub.5).sub. 2 2,3,5,6-tetramethylphenyl91 C(C.sub.2 H.sub.5).sub.2 4-ethylphenyl92 C(C.sub.2 H.sub.5).sub.2 4-isopropylphenyl93 C(C.sub.2 H.sub.5).sub.2 4-tert.butylphenyl mp. 122- 12494 C(C.sub.2 H.sub.5).sub.2 5-indanyl95 C(C.sub.2 H.sub.5).sub.2 1-naphthyl mp. 112- 11396 C(C.sub.2 H.sub.5).sub.2 2-naphthyl97 C(C.sub.2 H.sub.5).sub.2 2-methyl-1-naphthyl98 C(C.sub.2 H.sub.5).sub.2 4-biphenyl99 C(C.sub.2 H.sub.5).sub.2 2-fluorophenyl100 C(C.sub.2 H.sub.5).sub.2 3-fluorophenyl mp. 120- 122101 C(C.sub.2 H.sub.5).sub.2 4-fluorophenyl mp. 148- 150102 C(C.sub.2 H.sub.5).sub.2 2,3-difluorophenyl103 C(C.sub.2 H.sub.5).sub.2 2,4-difluorophenyl104 C(C.sub.2 H.sub.5).sub.2 2,5-difluorophenyl105 C(C.sub.2 H.sub.5).sub.2 2,6-difluorophenyl106 C(C.sub.2 H.sub.5).sub.2 3,4-difluorophenyl107 C(C.sub.2 H.sub.5).sub.2 3,5-difluorophenyl108 C(C.sub.2 H.sub.5).sub.2 2-fluoro-3-methylphenyl109 C(C.sub.2 H.sub.5).sub.2 2,3,5,6-tetrafluorophenyl110 C(C.sub.2 H.sub.5).sub.2 pentafluorophenyl111 C(C.sub.2 H.sub.5).sub.2 2-chlorophenyl mp. 96- 98112 C(C.sub.2 H.sub.5).sub.2 3-chlorophenyl113 C(C.sub.2 H.sub.5).sub.2 4-chlorophenyl mp. 128- 129114 C(C.sub.2 H.sub.5).sub.2 2,3-dichlorophenyl115 C(C.sub.2 H.sub.5).sub.2 2,4-dichlorophenyl mp. 139- 140116 C(C.sub.2 H.sub.5).sub.2 2,5-dichlorophenyl117 C(C.sub.2 H.sub.5).sub.2 2,6-dichlorophenyl118 C(C.sub.2 H.sub.5).sub.2 3,4-dichlorophenyl119 C(C.sub.2 H.sub.5).sub.2 3,5-dichlorophenyl120 C(C.sub.2 H.sub.5).sub.2 2,4,5-trichlorophenyl121 C(C.sub.2 H.sub.5).sub.2 2,4,6-trichlorophenyl122 C(C.sub.2 H.sub.5).sub.2 2,3,6-trichlorophenyl123 C(C.sub.2 H.sub.5).sub.2 2-chloro-5-methylphenyl124 C(C.sub.2 H.sub.5).sub.2 3-chloro-4-methylphenyl125 C(C.sub.2 H.sub.5).sub.2 2-chloro-4-fluorophenyl126 C(C.sub.2 H.sub.5).sub.2 2-chloro-6-fluorophenyl127 C(C.sub.2 H.sub.5).sub.2 3-chloro-2-fluorophenyl128 C(C.sub.2 H.sub.5).sub.2 pentachlorophenyl129 C(C.sub.2 H.sub.5).sub.2 2-bromophenyl130 C(C.sub.2 H.sub.5).sub.2 3-bromophenyl131 C(C.sub.2 H.sub.5).sub.2 4-bromophenyl132 C(C.sub.2 H.sub.5).sub.2 2-fluoro-4-bromophenyl133 C(C.sub.2 H.sub.5).sub.2 2-trifluoromethylphenyl134 C(C.sub.2 H.sub.5 ).sub.2 3-trifluoromethylphenyl135 C(C.sub.2 H.sub.5).sub.2 4-trifluoromethylphenyl136 C(C.sub.2 H.sub.5).sub.2 2,4-bis(trifluoromethyl)- phenyl137 C(C.sub.2 H.sub.5).sub.2 3,5-bis(trifluoromethyl)- phenyl138 C(C.sub.2 H.sub.5).sub.2 2-methoxyphenyl139 C(C.sub.2 H.sub.5).sub.2 3-methoxyphenyl140 C(C.sub.2 H.sub.5).sub.2 4-methoxyphenyl141 C(C.sub.2 H.sub.5).sub.2 3,4-dimethoxyphenyl142 C(C.sub.2 H.sub.5).sub.2 3,4,5-trimethoxyphenyl143 C(C.sub.2 H.sub.5).sub.2 4-ethoxyphenyl144 C(C.sub.2 H.sub.5).sub.2 4-tetrafluoroethoxyphenyl145 C(C.sub.2 H.sub.5).sub.2 4-trifluoromethoxyphenyl146 C(C.sub.2 H.sub.5).sub.2 4-methoxyiminocarbyl-phenyl147 C(C.sub.2 H.sub.5).sub.2 4-ethoxyiminocarbyl-phenyl148 C(C.sub.2 H.sub.5).sub.2 4-methoxy-3-methylphenyl149 C(C.sub.2 H.sub.5).sub.2 3-phenoxyphenyl150 C(C.sub.2 H.sub.5).sub.2 4-phenoxyphenyl151 C(C.sub.2 H.sub.5).sub.2 2-chloro-4-(4'-chloro- phenoxy)phenyl152 C(C.sub.2 H.sub.5).sub.2 4-(4'-chlorophenoxy)- phenyl)153 C(C.sub.2 H.sub.5).sub.2 4-benzyloxyphenyl154 C(CH.sub.2).sub.4 phenyl155 C(CH.sub.2).sub.4 2-methylphenyl156 C(CH.sub.2).sub.4 3-methylphenyl157 C(CH.sub.2).sub.4 4-methylphenyl158 C(CH.sub.2).sub.4 2,3-dimethylphenyl159 C(CH.sub.2).sub.4 2,4-dimethylphenyl160 C(CH.sub.2).sub.4 2,5-dimethylphenyl161 C(CH.sub.2).sub.4 2,6-dimethylphenyl162 C(CH.sub.2).sub.4 3,4-dimethylphenyl163 C(CH.sub.2).sub.4 3,5-dimethylphenyl164 C(CH.sub.2).sub.4 2,4,5-trimethylphenyl165 C(CH.sub.2).sub.4 2,4,6-trimethylphenyl166 C(CH.sub.2).sub.4 2,3,5,6-tetramethylphenyl167 C(CH.sub.2).sub.4 4-ethylphenyl168 C(CH.sub.2).sub.4 4-isopropylphenyl169 C(CH.sub.2).sub.4 4-tert.butylphenyl170 C(CH.sub.2).sub.4 5-indanyl171 C(CH.sub.2).sub.4 1-naphthyl172 C(CH.sub.2).sub.4 2-naphthyl173 C(CH.sub.2).sub.4 2-methyl-1-naphthyl174 C(CH.sub.2).sub.4 4-biphenyl175 C(CH.sub.2).sub.4 2-fluorophenyl mp. 75- 76176 C(CH.sub.2).sub.4 3-fluorophenyl177 C(CH.sub.2).sub.4 4-fluorophenyl mp. 166- 168178 C(CH.sub.2).sub.4 2,3-difluorophenyl179 C(CH.sub.2).sub.4 2,4-difluorophenyl180 C(CH.sub.2).sub.4 2,5-difluorophenyl181 C(CH.sub.2).sub.4 2,6-difluorophenyl182 C(CH.sub.2).sub.4 3,4-difluorophenyl183 C(CH.sub.2).sub.4 3,5-difluorophenyl184 C(CH.sub.2).sub.4 2-fluoro-3-methylphenyl185 C(CH.sub.2).sub.4 2,3,5,6-tetrafluorophenyl186 C(CH.sub.2).sub.4 pentafluorophenyl187 C(CH.sub.2).sub.4 2-chlorophenyl mp. 114- 116188 C(CH.sub.2).sub.4 3-chlorophenyl189 C(CH.sub.2).sub.4 4-chlorophenyl mp. 162- 164190 C(CH.sub.2).sub.4 2,3-dichlorophenyl191 C(CH.sub.2).sub.4 2,4-dichlorophenyl mp. 110- 112192 C(CH.sub.2).sub.4 2,5-dichlorophenyl193 C(CH.sub.2).sub.4 2,6-dichlorophenyl194 C(CH.sub.2).sub.4 3,4-dichlorophenyl195 C(CH.sub.2).sub.4 3,5-dichlorophenyl196 C(CH.sub.2).sub.4 2,4,5-trichlorophenyl197 C(CH.sub.2).sub.4 2,4,6-trichlorophenyl198 C(CH.sub.2).sub.4 2,3,6-trichlorophenyl199 C(CH.sub.2).sub.4 2-chloro-5-methylphenyl200 C(CH.sub.2).sub.4 3-chloro-4-methylphenyl201 C(CH.sub.2).sub.4 2-chloro-4-fluorophenyl202 C(CH.sub.2).sub.4 2-chloro-6-fluorophenyl203 C(CH.sub.2).sub.4 3-chloro-2-fluorophenyl204 C(CH.sub.2).sub.4 pentachlorophenyl205 C(CH.sub.2).sub.4 2-bromophenyl206 C(CH.sub.2).sub.4 3-bromophenyl207 C(CH.sub.2).sub.4 4-bromophenyl208 C(CH.sub.2).sub.4 2-fluoro-4-bromophenyl209 C(CH.sub.2).sub.4 2-trifluoromethylphenyl210 C(CH.sub.2).sub.4 3-trifluoromethylphenyl211 C(CH.sub.2).sub.4 4-trifluoromethylphenyl212 C(CH.sub.2).sub.4 2,4-bis(trifluoromethyl)- phenyl213 C(CH.sub.2).sub.4 3,5-bis(trifluoromethyl)- phenyl214 C(CH.sub.2).sub.4 2-methoxyphenyl215 C(CH.sub.2).sub.4 3-methoxyphenyl216 C(CH.sub.2).sub.4 4-methoxyphenyl217 C(CH.sub.2).sub.4 3,4-dimethoxyphenyl218 C(CH.sub.2).sub.4 3,4,5-trimethoxyphenyl219 C(CH.sub.2).sub.4 4-ethoxyphenyl220 C(CH.sub. 2).sub.4 4-tetrafluoroethoxyphenyl221 C(CH.sub.2).sub.4 4-trifluoromethoxyphenyl222 C(CH.sub.2).sub.4 4-methoxyiminocarbyl-phenyl223 C(CH.sub.2).sub.4 4-ethoxyiminocarbyl-phenyl224 C(CH.sub.2).sub.4 4-methoxy-3-methylphenyl225 C(CH.sub.2).sub.4 3-phenoxyphenyl226 C(CH.sub.2).sub.4 4-phenoxyphenyl227 C(CH.sub.2).sub.4 2-chloro-4-(4'-chloro- phenoxy)phenyl228 C(CH.sub.2).sub.4 3-(4'-fluorophenoxy)- phenyl229 C(CH.sub.2).sub.4 4-benzyloxyphenyl230 C(CH.sub.2).sub.5 phenyl mp. 117- 119231 C(CH.sub.2).sub.5 2-methylphenyl232 C(CH.sub.2).sub.5 3-methylphenyl233 C(CH.sub.2).sub.5 4-methylphenyl234 C(CH.sub.2).sub.5 2,3-dimethylphenyl235 C(CH.sub.2).sub.5 2,4-dimethylphenyl236 C(CH.sub.2).sub.5 2,5-dimethylphenyl237 C(CH.sub.2).sub.5 2,6-dimethylphenyl238 C(CH.sub.2).sub.5 3,4-dimethylphenyl239 C(CH.sub.2).sub.5 3,5-dimethylphenyl240 C(CH.sub.2).sub.5 2,4,5-trimethylphenyl241 C(CH.sub.2).sub.5 2,4,6-trimethylphenyl242 C(CH.sub.2).sub.5 2,3,5,6-tetramethylphenyl243 C(CH.sub.2).sub.5 4-ethylphenyl244 C(CH.sub.2).sub.5 4-isopropylphenyl245 C(CH.sub.2).sub.5 4-tert-butylphenyl246 C(CH.sub.2).sub.5 5-indanyl247 C(CH.sub.2).sub.5 1-naphthyl248 C(CH.sub.2).sub.5 2-naphthyl249 C(CH.sub.2).sub.5 2-methyl-1-naphthyl250 C(CH.sub.2).sub.5 4-biphenyl251 C(CH.sub.2).sub.5 2-fluorophenyl mp. 146- 148252 C(CH.sub.2).sub.5 3-fluorophenyl mp. 132- 134253 C(CH.sub.2).sub.5 4-fluorophenyl mp. 126- 127254 C(CH.sub.2).sub.5 2,3-difluorophenyl255 C(CH.sub.2).sub.5 2,4-difluorophenyl256 C(CH.sub.2).sub.5 2,5-difluorophenyl257 C(CH.sub.2).sub.5 2,6-difluorophenyl258 C(CH.sub.2).sub.5 3,4-difluorophenyl259 C(CH.sub.2).sub.5 3,5-difluorophenyl260 C(CH.sub.2).sub.5 2-fluoro-3-methylphenyl261 C(CH.sub.2).sub.5 2,3,5,6-tetrafluorophenyl262 C(CH.sub.2).sub.5 pentafluorphenyl263 C(CH.sub.2).sub.5 2-chlorophenyl mp. 162- 164264 C(CH.sub.2).sub.5 3-chlorophenyl265 C(CH.sub.2).sub.5 4-chlorophenyl mp. 155- 156266 C(CH.sub.2).sub.5 2,3-dichlorophenyl267 C(CH.sub.2).sub.5 2,4-dichlorophenyl oil; N-oxide mp. 205- 207268 C(CH.sub.2).sub.5 2,5-dichlorophenyl269 C(CH.sub.2).sub.5 2,6-dichlorophenyl270 C(CH.sub.2).sub.5 3,4-dichlorophenyl mp. 181- 183271 C(CH.sub.2).sub.5 3,5-dichlorophenyl272 C(CH.sub.2).sub.5 2,4,5-trichlorophenyl273 C(CH.sub.2).sub.5 2,4,6-trichlorophenyl274 C(CH.sub.2).sub.5 2,3,6-trichlorophenyl275 C(CH.sub.2).sub.5 2-chloro-5-methylphenyl276 C(CH.sub.2).sub.5 3-chloro-4-methylphenyl277 C(CH.sub.2).sub.5 2-chloro-4-fluorophenyl278 C(CH.sub.2).sub.5 2-chloro-6-fluorophenyl279 C(CH.sub.2).sub.5 3-chloro-2-fluorophenyl280 C(CH.sub.2).sub.5 pentachlorophenyl281 C(CH.sub.2).sub.5 2-bromophenyl282 C(CH.sub.2).sub.5 3-bromophenyl283 C(CH.sub.2).sub.5 4-bromophenyl mp. 190- 191284 C(CH.sub.2).sub.5 2-fluoro-4-bromophenyl285 C(CH.sub.2).sub.5 2-trifluoromethylphenyl286 C(CH.sub.2).sub.5 3-trifluoromethylphenyl287 C(CH.sub.2).sub.5 4-trifluoromethylphenyl288 C(CH.sub.2).sub.5 2,4-bis(trifluoromethyl)- phenyl289 C(CH.sub.2).sub.5 3,5-bis(trifluoromethyl)- phenyl290 C(CH.sub.2).sub.5 2-methoxyphenyl291 C(CH.sub.2).sub.5 3-methoxyphenyl292 C(CH.sub.2).sub.5 4-methoxyphenyl293 C(CH.sub.2).sub.5 3,4-dimethoxyphenyl294 C(CH.sub.2).sub.5 3,4,5-trimethoxyphenyl295 C(CH.sub.2).sub.5 4-ethoxyphenyl296 C(CH.sub.2).sub.5 4-tetrafluoroethoxyphenyl297 C(CH.sub.2).sub.5 4-trifluoromethoxyphenyl298 C(CH.sub.2).sub.5 4-methoxyiminocarbyl-phenyl299 C(CH.sub.2).sub.5 4-ethoxyiminocarbyl-phenyl300 C(CH.sub.2).sub.5 4-methoxy-3-methylphenyl301 C(CH.sub.2).sub.5 3-phenoxyphenyl302 C(CH.sub.2).sub.5 4-phenoxyphenyl303 C(CH.sub.2).sub.5 2-chloro-4-(4'-chloro- phenoxy)phenyl304 C(CH.sub.2).sub.5 3-(4'-fluorophenoxy)- phenyl305 C(CH.sub.2).sub.5 4-benzyloxyphenyl306 C(CH.sub.3)nC.sub.3 H.sub.7 phenyl oil; N-oxide mp. 154- 156307 C(CH.sub.3)nC.sub.3 H.sub.7 2-methylphenyl308 C(CH.sub.3)nC.sub.3 H.sub.7 3-methylphenyl309 C(CH.sub.3)nC.sub.3 H.sub.7 4-methylphenyl310 C(CH.sub.3)nC.sub.3 H.sub.7 2,3-dimethylphenyl311 C(CH.sub.3)nC.sub.3 H.sub.7 2,4-dimethylphenyl312 C(CH.sub.3)nC.sub.3 H.sub.7 2,5-dimethylphenyl313 C(CH.sub.3)nC.sub.3 H.sub.7 2,6-dimethylphenyl314 C(CH.sub.3)nC.sub.3 H.sub.7 3,4-dimethylphenyl315 C(CH.sub.3)nC.sub.3 H.sub.7 3,5-dimethylphenyl316 C(CH.sub.3)nC.sub.3 H.sub.7 2,4,5-trimethylphenyl317 C(CH.sub.3)nC.sub.3 H.sub.7 2,4,6-trimethylphenyl318 C(CH.sub.3)nC.sub.3 H.sub.7 2,3,5,6-tetramethylphenyl319 C(CH.sub.3)nC.sub.3 H.sub.7 4-ethylphenyl320 C(CH.sub.3)nC.sub.3 H.sub.7 4-isopropylphenyl321 C(CH.sub.3)nC.sub.3 H.sub.7 4-tert.butylphenyl322 C(CH.sub.3)nC.sub.3 H.sub.7 5-indanyl323 C(CH.sub.3)nC.sub.3 H.sub.7 1-naphthyl324 C(CH.sub.3)nC.sub.3 H.sub.7 2-naphthyl325 C(CH.sub.3)nC.sub.3 H.sub.7 2-methyl-1-naphthyl326 C(CH.sub.3)nC.sub.3 H.sub.7 4-biphenyl327 C(CH.sub.3)nC.sub.3 H.sub.7 2-fluorophenyl328 C(CH.sub.3)nC.sub.3 H.sub.7 3-fluorophenyl329 C(CH.sub.3)nC.sub.3 H.sub.7 4-fluorophenyl330 C(CH.sub.3)nC.sub.3 H.sub.7 2,3-difluorophenyl331 C(CH.sub.3)nC.sub.3 H.sub.7 2,4-difluorophenyl332 C(CH.sub.3)nC.sub.3 H.sub.7 2,5-difluorophenyl333 C(CH.sub.3)nC.sub.3 H.sub.7 2,6-difluorophenyl334 C(CH.sub.3)nC.sub.3 H.sub.7 3,4-difluorophenyl335 C(CH.sub.3)nC.sub.3 H.sub.7 3,5-difluorophenyl336 C(CH.sub.3)nC.sub.3 H.sub.7 2-fluoro-3-methylphenyl337 C(CH.sub.3)nC.sub.3 H.sub.7 2,3,5,6-tetrafluorophenyl338 C(CH.sub.3)nC.sub.3 H.sub.7 pentafluorophenyl339 C(CH.sub.3)nC.sub.3 H.sub.7 2-chlorophenyl340 C(CH.sub.3)nC.sub.3 H.sub.7 3-chlorophenyl341 C(CH.sub.3)nC.sub.3 H.sub.7 4-chlorophenyl oil; N-oxide: mp. 159- 160342 C(CH.sub.3)nC.sub.3 H.sub.7 2,3-dichlorophenyl343 C(CH.sub.3)nC.sub.3 H.sub.7 2,4-dichlorophenyl344 C(CH.sub.3)nC.sub.3 H.sub.7 2,5-dichlorophenyl345 C(CH.sub.3)nC.sub.3 H.sub.7 2,6-dichlorophenyl346 C(CH.sub.3)nC.sub.3 H.sub.7 3,4-dichlorophenyl347 C(CH.sub.3)nC.sub.3 H.sub.7 3,5-dichlorophenyl348 C(CH.sub.3)nC.sub.3 H.sub.7 2,4,5-trichlorophenyl349 C(CH.sub.3)nC.sub.3 H.sub.7 2,4,6-trichlorophenyl350 C(CH.sub.3)nC.sub.3 H.sub.7 2,3,6-trichlorophenyl351 C(CH.sub.3)nC.sub.3 H.sub.7 2-chloro-5-methylphenyl352 C(CH.sub. 3)nC.sub.3 H.sub.7 3-chloro-4-methylphenyl353 C(CH.sub.3)nC.sub.3 H.sub.7 2-chloro-4-fluorophenyl354 C(CH.sub.3)nC.sub.3 H.sub.7 2-chloro-6-fluorophenyl355 C(CH.sub.3)nC.sub.3 H.sub.7 3-chloro-2-fluorophenyl356 C(CH.sub.3)nC.sub.3 H.sub.7 pentachlorophenyl357 C(CH.sub.3)nC.sub.3 H.sub.7 2-bromophenyl358 C(CH.sub.3)nC.sub.3 H.sub.7 3-bromophenyl359 C(CH.sub.3)nC.sub.3 H.sub.7 4-bromophenyl360 C(CH.sub.3)nC.sub.3 H.sub.7 2-fluoro-4-bromophenyl361 C(CH.sub.3)nC.sub.3 H.sub.7 2-trifluoromethylphenyl362 C(CH.sub.3)nC.sub.3 H.sub.7 3-trifluoromethylphenyl363 C(CH.sub.3)nC.sub.3 H.sub.7 4-trifluoromethylphenyl364 C(CH.sub.3)nC.sub.3 H.sub.7 2,4-bis(trifluoromethyl)- phenyl365 C(CH.sub.3)nC.sub.3 H.sub.7 3,5-bis(trifluoromethyl)- phenyl366 C(CH.sub.3)nC.sub.3 H.sub.7 2-methoxyphenyl367 C(CH.sub.3)nC.sub.3 H.sub.7 3-methoxyphenyl368 C(CH.sub.3)nC.sub.3 H.sub.7 4-methoxyphenyl369 C(CH.sub.3)nC.sub.3 H.sub.7 3,4-dimethoxyphenyl370 C(CH.sub.3)nC.sub.3 H.sub.7 3,4,5-trimethoxyphenyl371 C(CH.sub.3)nC.sub.3 H.sub.7 4-ethoxyphenyl372 C(CH.sub.3)nC.sub.3 H.sub.7 4-tetrafluoroethoxyphenyl373 C(CH.sub.3)nC.sub.3 H.sub.7 4-trifluoromethoxyphenyl374 C(CH.sub.3)nC.sub.3 H.sub.7 4-methoxyiminocarbyl-phenyl375 C(CH.sub.3)nC.sub.3 H.sub.7 4-ethoxyiminocarbyl-phenyl376 C(CH.sub.3)nC.sub. 3 H.sub.7 4-methoxy-3-methylphenyl377 C(CH.sub.3)nC.sub.3 H.sub.7 3-phenoxyphenyl378 C(CH.sub.3)nC.sub.3 H.sub.7 4-phenoxyphenyl379 C(CH.sub.3)nC.sub.3 H.sub.7 2-chloro-4-(4'-chloro- phenoxy)phenyl380 C(CH.sub.3)nC.sub.3 H.sub.7 3-(4'-fluorophenoxy)- phenyl381 C(CH.sub.3)nC.sub.3 H.sub.7 4-benzyloxyphenyl382 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 phenyl oil383 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-methylphenyl384 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-methylphenyl385 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-methylphenyl386 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3-dimethylphenyl387 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4-dimethylphenyl388 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,5-dimethylphenyl389 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,6-dimethylphenyl390 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4-dimethylphenyl391 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,5-dimethylphenyl392 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4,5-trimethylphenyl393 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4,6-trimethylphenyl394 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3,5,6-tetramethylphenyl395 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-ethylphenyl396 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-isopropylphenyl397 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-tert.butylphenyl398 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 5-indanyl399 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 1-naphthyl400 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-naphthyl401 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-methyl-1-napthyl402 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-biphenyl403 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-fluorophenyl404 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-fluorophenyl405 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-fluorophenyl406 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3-difluorophenyl407 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4-difluorophenyl408 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,5-difluorophenyl409 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,6-difluorophenyl410 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4-difluorophenyl411 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,5-difluorophenyl412 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-fluoro-3-methylphenyl413 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3,5,6-tetrafluorophenyl414 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 pentafluorophenyl415 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-chlorophenyl416 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-chlorophenyl417 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-chlorophenyl418 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3-dichlorophenyl419 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4-dichlorophenyl420 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,5-dichlorophenyl421 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,6-dichlorophenyl422 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4-dichlorophenyl423 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,5-dichlorophenyl424 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4,5-trichlorophenyl425 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4,6-trichlorophenyl426 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,3,6-trichlorophenyl427 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-chloro-5-methylphenyl428 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-chloro-4-methylphenyl429 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-chloro-4-fluorophenyl430 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-chloro-6-fluorophenyl431 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-chloro-2-fluorophenyl432 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 pentachlorophenyl433 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-bromophenyl434 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-bromophenyl435 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-bromophenyl436 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-fluoro-4-bromophenyl437 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-trifluoromethylphenyl438 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-trifluoromethylphenyl439 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-trifluormethylphenyl440 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2,4-bis(trifluoromethyl)- phenyl441 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,5-bis(trifluoromethyl)- phenyl442 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-methoxyphenyl443 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-methoxyphenyl444 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-methoxyphenyl445 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4-dimethoxyphenyl446 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3,4,5-trimethoxyphenyl447 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-ethoxyphenyl448 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-tetrafluoroethoxyphenyl449 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-trifluoromethoxyphenyl450 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-methoxyiminocarbyl-phenyl451 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-ethoxyiminocarbyl-phenyl452 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-methoxy-3-methylphenyl453 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-phenoxyphenyl454 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-phenoxyphenyl455 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 2-chloro-4-(4'-chloro- phenoxy)phenyl456 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 3-(4'-fluorophenoxy)- phenyl457 C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9 4-benzyloxyphenyl458 C(CH.sub.2).sub.3 OCH.sub.2 phenyl459 C(CH.sub.2).sub.3 OCH.sub.2 2-methylphenyl460 C(CH.sub.2).sub.3 OCH.sub.2 3-methylphenyl461 C(CH.sub.2).sub.3 OCH.sub.2 4-methylphenyl462 C(CH.sub.2).sub.3 OCH.sub.2 2,3-dimethylphenyl463 C(CH.sub.2).sub.3 OCH.sub.2 2,4-dimethylphenyl464 C(CH.sub.2).sub.3 OCH.sub.2 2,5-dimethylphenyl465 C(CH.sub.2).sub.3 OCH.sub.2 2,6-dimethylphenyl466 C(CH.sub.2).sub.3 OCH.sub.2 3,4-dimethylphenyl467 C(CH.sub.2).sub.3 OCH.sub.2 3,5-dimethylphenyl468 C(CH.sub.2).sub.3 OCH.sub.2 2,4,5-trimethylphenyl469 C(CH.sub.2).sub.3 OCH.sub.2 2,4,6-trimethylphenyl470 C(CH.sub.2).sub.3 OCH.sub.2 2,3,5,6-tetramethylphenyl471 C(CH.sub.2).sub.3 OCH.sub.2 4-ethylphenyl472 C(CH.sub.2).sub.3 OCH.sub.2 4-isopropylphenyl473 C(CH.sub.2).sub.3 OCH.sub.2 4-tert.butylphenyl474 C(CH.sub.2).sub.3 OCH.sub.2 5-indanyl475 C(CH.sub.2).sub.3 OCH.sub.2 1-naphthyl476 C(CH.sub.2).sub.3 OCH.sub.2 2-naphthyl477 C(CH.sub.2).sub.3 OCH.sub.2 2-methyl-1-napthyl478 C(CH.sub.2).sub.3 OCH.sub.2 4-biphenyl479 C(CH.sub.2).sub.3 OCH.sub.2 2-fluorophenyl480 C(CH.sub.2).sub.3 OCH.sub.2 3-fluorophenyl481 C(CH.sub.2).sub.3 OCH.sub.2 4-fluorophenyl482 C(CH.sub.2).sub.3 OCH.sub.2 2,3-difluorophenyl483 C(CH.sub.2).sub.3 OCH.sub.2 2,4-difluorophenyl484 C(CH.sub.2).sub.3 OCH.sub.2 2,5-difluorophenyl485 C(CH.sub.2).sub.3 OCH.sub.2 2,6-difluorophenyl486 C(CH.sub.2).sub.3 OCH.sub.2 3,4-difluorophenyl487 C(CH.sub.2).sub.3 OCH.sub.2 3,5-difluorophenyl488 C(CH.sub.2).sub.3 OCH.sub.2 2-fluoro-3-methylphenyl489 C(CH.sub.2).sub.3 OCH.sub.2 2,3,5,6-tetrafluorophenyl490 C(CH.sub.2).sub.3 OCH.sub.2 pentafluorophenyl491 C(CH.sub.2).sub.3 OCH.sub.2 2-chlorophenyl492 C(CH.sub.2).sub.3 OCH.sub.2 3-chlorophenyl493 C(CH.sub.2).sub.3 OCH.sub.2 4-chlorophenyl494 C(CH.sub.2).sub.3 OCH.sub.2 2,3-dichlorophenyl495 C(CH.sub.2).sub.3 OCH.sub.2 2,4-dichlorophenyl496 C(CH.sub.2).sub.3 OCH.sub.2 2,5-dichlorophenyl497 C(CH.sub.2).sub.3 OCH.sub.2 2,6-dichlorophenyl498 C(CH.sub.2).sub.3 OCH.sub.2 3,4-dichlorophenyl499 C(CH.sub.2).sub.3 OCH.sub.2 3,5-dichlorophenyl500 C(CH.sub.2).sub.3 OCH.sub.2 2,4,5-trichlorophenyl501 C(CH.sub.2).sub.3 OCH.sub.2 2,4,6-trichlorophenyl502 C(CH.sub.2).sub.3 OCH.sub.2 2,3,6-trichlorophenyl503 C(CH.sub.2).sub.3 OCH.sub.2 2-chloro-5-methylphenyl504 C(CH.sub.2).sub.3 OCH.sub.2 3-chloro-4-methylphenyl505 C(CH.sub.2).sub.3 OCH.sub.2 2-chloro-4-fluorophenyl506 C(CH.sub.2).sub.3 OCH.sub.2 2-chloro-6-fluorophenyl507 C(CH.sub.2).sub.3 OCH.sub.2 3-chloro-2-fluorophenyl508 C(CH.sub.2).sub.3 OCH.sub.2 pentachlorophenyl509 C(CH.sub.2).sub.3 OCH.sub.2 2-bromophenyl510 C(CH.sub.2).sub.3 OCH.sub.2 3-bromophenyl511 C(CH.sub.2).sub.3 OCH.sub.2 4-bromophenyl512 C(CH.sub.2).sub.3 OCH.sub.2 2-fluoro-4-bromophenyl513 C(CH.sub.2).sub.3 OCH.sub.2 2-trifluoromethylphenyl514 C(CH.sub.2).sub.3 OCH.sub.2 3-trifluoromethylphenyl515 C(CH.sub.2).sub.3 OCH.sub.2 4-trifluoromethylphenyl516 C(CH.sub.2).sub.3 OCH.sub.2 2,4-bis(trifluoromethyl)- phenyl517 C(CH.sub.2).sub.3 OCH.sub.2 3,5-bis(trifluoromethyl)- phenyl518 C(CH.sub.2).sub.3 OCH.sub.2 2-methoxyphenyl519 C(CH.sub.2).sub.3 OCH.sub.2 3-methoxyphenyl520 C(CH.sub.2).sub.3 OCH.sub.2 4-methoxyphenyl521 C(CH.sub.2).sub.3 OCH.sub.2 3,4-dimethoxyphenyl522 C(CH.sub.2).sub.3 OCH.sub.2 3,4,5-trimethoxyphenyl523 C(CH.sub.2).sub.3 OCH.sub.2 4-ethoxyphenyl524 C(CH.sub.2).sub.3 OCH.sub.2 4-tetrafluoroethoxyphenyl525 C(CH.sub.2).sub.3 OCH.sub.2 4-trifluoromethoxyphenyl526 C(CH.sub.2).sub.3 OCH.sub.2 4-methoxyiminocarbyl-phenyl527 C(CH.sub.2).sub.3 OCH.sub.2 4-ethoxyiminocarbyl-phenyl528 C(CH.sub.2).sub.3 OCH.sub.2 4-methoxy-3-methylphenyl529 C(CH.sub.2).sub.3 OCH.sub.2 3-phenoxyphenyl530 C(CH.sub.2).sub.3 OCH.sub.2 4-phenoxyphenyl531 C(CH.sub.2).sub.3 OCH.sub.2 2-chloro-4-(4'-chloro- phenoxy)phenyl532 C(CH.sub.2).sub.3 OCH.sub.2 3-(4'-fluorophenoxy)- phenyl533 C(CH.sub.2).sub.3 OCH.sub.2 4-benzyloxyphenyl534 C(CH.sub.2).sub.2 phenyl535 C(CH.sub.2).sub.2 2-methylphenyl536 C(CH.sub.2).sub.2 3-methylphenyl537 C(CH.sub.2).sub.2 4-methylphenyl538 C(CH.sub.2).sub.2 2,3-dimethylphenyl539 C(CH.sub.2).sub.2 2,4-dimethylphenyl540 C(CH.sub.2).sub.2 2,5-dimethylphenyl541 C(CH.sub.2).sub.2 2,6-dimethylphenyl542 C(CH.sub.2).sub.2 3,4-dimethylphenyl543 C(CH.sub.2).sub.2 3,5-dimethylphenyl544 C(CH.sub.2).sub.2 2,4,5-trimethylphenyl545 C(CH.sub.2).sub.2 2,4,6-trimethylphenyl546 C(CH.sub.2).sub.2 2,3,5,6-tetramethylphenyl547 C(CH.sub.2).sub.2 4-ethylphenyl548 C(CH.sub.2).sub.2 4-isopropylphenyl549 C(CH.sub.2).sub.2 4-tert.butylphenyl550 C(CH.sub.2).sub.2 5-indanyl551 C(CH.sub.2).sub.2 1-naphthyl552 C(CH.sub.2).sub.2 2-naphthyl553 C(CH.sub.2).sub.2 2-methyl-1-napthyl554 C(CH.sub.2).sub.2 4-biphenyl555 C(CH.sub.2).sub.2 2-fluorophenyl556 C(CH.sub.2).sub.2 3-fluorophenyl557 C(CH.sub.2).sub.2 4-fluorophenyl558 C(CH.sub.2).sub.2 2,3-difluorophenyl559 C(CH.sub.2).sub.2 2,4-difluorophenyl560 C(CH.sub.2).sub.2 2,5-difluorophenyl561 C(CH.sub.2).sub.2 2,6-difluorophenyl562 C(CH.sub.2).sub.2 3,4-difluorophenyl563 C(CH.sub.2).sub.2 3,5-difluorophenyl564 C(CH.sub.2).sub.2 2-fluoro-3-methylphenyl565 C(CH.sub.2).sub.2 2,3,5,6-tetrafluorophenyl566 C(CH.sub.2).sub.2 pentafluorophenyl567 C(CH.sub.2).sub.2 2-chlorophenyl568 C(CH.sub.2).sub.2 3-chlorophenyl569 C(CH.sub.2).sub.2 4-chlorophenyl570 C(CH.sub.2).sub.2 2,3-dichlorophenyl571 C(CH.sub.2).sub.2 2,4-dichlorophenyl572 C(CH.sub.2).sub.2 2,5-dichlorophenyl573 C(CH.sub.2).sub.2 2,6-dichlorophenyl574 C(CH.sub.2).sub.2 3,4-dichlorophenyl575 C(CH.sub.2).sub.2 3,5-dichlorophenyl576 C(CH.sub.2).sub.2 2,4,5-trichlorophenyl577 C(CH.sub.2).sub.2 2,4,6-trichlorophenyl578 C(CH.sub.2).sub.2 2,3,6-trichlorophenyl579 C(CH.sub.2).sub.2 2-chloro-5-methylphenyl580 C(CH.sub.2).sub.2 3-chloro-4-methylphenyl581 C(CH.sub.2).sub.2 2-chloro-4-fluorophenyl582 C(CH.sub.2).sub.2 2-chloro-6-fluorophenyl583 C(CH.sub.2).sub.2 3-chloro-2-fluorophenyl584 C(CH.sub.2).sub.2 pentachlorophenyl585 C(CH.sub.2).sub.2 2-bromophenyl586 C(CH.sub.2).sub.2 3-bromophenyl587 C(CH.sub.2).sub.2 4-bromophenyl588 C(CH.sub.2).sub.2 2-fluoro-4-bromophenyl589 C(CH.sub.2).sub.2 2-trifluoromethylphenyl590 C(CH.sub.2).sub.2 3-trifluoromethylphenyl591 C(CH.sub.2).sub.2 4-trifluoromethylphenyl592 C(CH.sub.2 ).sub.2 2,4-bis(trifluoromethyl)- phenyl593 C(CH.sub.2).sub.2 3,5-bis(trifluoromethyl)- phenyl594 C(CH.sub.2).sub.2 2-methoxyphenyl595 C(CH.sub.2).sub.2 3-methoxyphenyl596 C(CH.sub.2).sub.2 4-methoxyphenyl597 C(CH.sub.2).sub.2 3,4-dimethoxyphenyl598 C(CH.sub.2).sub.2 3,4,5-trimethoxyphenyl599 C(CH.sub.2).sub.2 4-ethoxyphenyl600 C(CH.sub.2).sub.2 4-tetrafluoroethoxyphenyl601 C(CH.sub.2).sub.2 4-trifluoromethoxyphenyl602 C(CH.sub.2).sub.2 4-methoxyiminocarbyl-phenyl603 C(CH.sub.2).sub.2 4-ethoxyiminocarbyl-phenyl604 C(CH.sub.2).sub.2 4-methoxy-3-methylphenyl605 C(CH.sub.2).sub.2 3-phenoxyphenyl606 C(CH.sub.2).sub.2 4-phenoxyphenyl607 C(CH.sub.2).sub.2 2-chloro-4-(4'-chloro- phenoxy)phenyl608 C(CH.sub.2).sub.2 3-(4'-fluorophenoxy)- phenyl609 C(CH.sub.2).sub.2 4-benzyloxyphenyl______________________________________
TABLE 2______________________________________ ##STR12##Ex.no. R.sup.2 A Ar Physical data______________________________________610 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 phenyl oil611 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-chlorophenyl oil612 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-fluorophenyl oil613 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 2,4-dichlorophenyl oil614 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 2-methylphenyl615 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-methylphenyl616 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-tert.-butylphenyl617 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 2-naphthyl618 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 2-fluorophenyl619 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 4-bromophenyl620 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 3-fluorophenyl621 CH.sub.3 C(C.sub.2 H.sub.5).sub.2 3,4-dichlorophenyl622 CH.sub.3 C(CH.sub.2).sub.5 phenyl623 CH.sub.3 C(CH.sub.2).sub.5 2-methylphenyl624 CH.sub.3 C(CH.sub.2).sub.5 4-methylphenyl625 CH.sub.3 C(CH.sub.2).sub.5 4-tert.-butylphenyl626 CH.sub.3 C(CH.sub.2).sub.5 2-naphthyl627 CH.sub.3 C(CH.sub.2).sub.5 2-fluorophenyl628 CH.sub.3 C(CH.sub.2).sub.5 3-fluorophenyl629 CH.sub.3 C(CH.sub.2).sub.5 4-fluorophenyl630 CH.sub.3 C(CH.sub.2).sub.5 4-bromophenyl631 CH.sub.3 C(CH.sub.2).sub.5 4-chlorophenyl632 CH.sub.3 C(CH.sub.2).sub.5 2-chlorophenyl633 CH.sub.3 C(CH.sub.2).sub.5 2,4-dichlorophenyl634 CH.sub.3 C(CH.sub.2).sub.5 3,4-dichlorophenyl635 CH.sub.3 C(CH.sub.2).sub.4 phenyl636 CH.sub.3 C(CH.sub.2).sub.4 2-methylphenyl637 CH.sub.3 C(CH.sub.2).sub.4 4-methylphenyl638 CH.sub.3 C(CH.sub.2).sub.4 4-tert.-butylphenyl639 CH.sub.3 C(CH.sub.2).sub.4 2-naphthyl640 CH.sub.3 C(CH.sub.2).sub.4 2-fluorophenyl641 CH.sub.3 C(CH.sub.2).sub.4 3-fluorophenyl642 CH.sub.3 C(CH.sub.2).sub.4 4-fluorophenyl643 CH.sub.3 C(CH.sub.2).sub.4 4-bromophenyl644 CH.sub.3 C(CH.sub.2).sub.4 4-chlorophenyl645 CH.sub.3 C(CH.sub.2).sub.4 2-chlorophenyl646 CH.sub.3 C(CH.sub.2).sub.4 2,4-dichlorophenyl647 CH.sub.3 C(CH.sub.2).sub.4 3,4-dichlorophenyl648 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 phenyl649 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 2-methylphenyl650 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-methylphenyl651 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-tert.-butylphenyl652 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 2-naphthyl653 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 2-fluorophenyl654 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 3-fluorophenyl655 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-fluorophenyl656 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-bromophenyl657 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 4-chlorophenyl658 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 2,4-dichlorophenyl659 CH.sub.3 C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9 3,4-dichlorophenyl660 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.
USE EXAMPLES
For comparison purposes, the compound 3-phenyl-2,2-dimethyl-1-(3-pyridyl)propan-1-ol (A) disclosed in EP 302,365 was used.
USE EXAMPLE 1
Action on Botrytis cinerea in pimientos
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%).
USE EXAMPLE 2
Action on Pyrenophora teres
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%).

Number	Date	Country
0302366	Jul 1988	EPX
0302365	Feb 1989	EPX
0311907	Apr 1989	EPX

Pyridine compounds which are useful as fungicides

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