IE53378B1 - Fungicidal 1,2,4-triazole and imidazole derivatives - Google Patents

Description

Background of the Invention The present invention relates to silylmethyltriazoles and imidazoles such as, for example, dimethyl(phenyl)(1H-1,2,4-triazol-l-ylmethyDsilane and (1,1'-biphenyl-4-yl)dimethy1(lH-imidazol-l-ylmethy1)silane, and to the use of these new compounds, in controlling fungus diseases, particularly diseases of living plants.

U.S. Patent 3,692,798 discloses compounds of the formula: wherein Rp R2 and R-j can be lower alkyl and phenyl. It is stated that these compounds are useful as antimicrobial agents.

European Patent 29,993 discloses compounds of the formula: wherein R can be C^-C^ alkyl and Y and Z can be H or SiR1R2R3, wherein Rp R2, and can be alkyl, haloalkyl, alkenyl, alkynyl, or substituted phenyl. It is taught that the compounds are useful as agricultural fungicides. a U.S. Patents 3,256,308 and 3,337,598 disclose compounds of the formula: R -Si— 0 CH, wherein R^ can be methyl, ethyl, vinyl, or phenyl. Their use to control fungi is also taught.

Belgian Patent 785,127 discloses quaternary ammonium salts such as: ch3© (CH30)3SiCH2CH2N-n-C18H37 ch3 and their use as fungicides.

Research Disclosure 17,652 discloses silyl ethers of the formula: 0SiR3 Ar-CH2-CH-CH-C(CH3)3 z'N w wherein Ar can be substituted phenyl, X can be CH or N, and R can be alkyl. It is taught that the com25 pounds are useful as agricultural fungicides.

West German Patent OE 3,000,140 discloses silyl ethers of the formula: 0SiR3 Ar-O-CH-CH-C(CH-), 1 ? J N wherein Ar can be substituted phenyl, X can be CH or N, and R can be phenyl or lower alkyl. It is taught that these compounds are useful as agricultural fungicides.

U.S. Patent 4,248,992 discloses a class of or ganosilicon compounds having In a molecule at least one monovalent guanidine group represented by the general formula: NR. '2 NR in which R is a hydrocarbon atom or a monovalent hy 10 drocarbon group. These guanidine-containing organo silicon compounds are described as useful as antifungal agents for molded plastics and rubbers, particularly silicone rubbers.

U.S.S.R. Patent 346,306 discloses silylmethyl 15 azoles of the formula: (R wherein R^ and R2 are alkyl groups, n is 0-3, and Az is a pyrazole, imidazole, or benzimidazole ring, optionally substituted.

U.S.S.R. Patent 271,552 discloses silylethylazoles of the formula: (R1)n(R2°)3-nSiCH2CH2Az wherein Rj, R2, n, and Az are as described in the previous reference. 3 3 7 8 Summary of the Invention This invention relates to silylmethyltriazoles of Formula I and to silylmethylimidazoles of Formula Il and to agriculturally useful compositions of these compounds.

I II wherein βρ Q2and are independently H or CH3; n is 1; R1 is c2c18 naphthyl, alkyl, C3-Cg eycloalkyl, or R'l is Cfi-C18 alkyl, C3~Cfi eycloalkyl, naphthyl or where R4 and R5 are independently -H; halogen; -0CH3; -0CF3; -SCH3; -S02CH3; phenyl; phenyl substituted with halogen and/or C^-C^ alkyl and/or -CF3; phenoxy; phenoxy substituted with halogen and/or Cj-C^ alkyl and/or -CF3; -CF3; C1“C4 alky1’ or cyclohexyl; with the proviso that for compounds of Formula II, both R^ and R3 may not simultaneously be H; and R2 and Rj are independently C^-Cg alkyl, CyCg cycloalkyl, ORg, or where Rg is H or Cj-C^ alkyl, with the proviso that both R2 and Rj may not be OH; and R2 and Rj together may be a 1,2- or 1,3- or 1,4-glycol bridge or a 1,4 unsaturated glycol bridge substituted by up to four alkyl groups R7-R^0 that have a total of up to four carbon atoms. _L7_Rl° rr\ z°R7-R10 01 Π z°R7-R10 oR7R10 01 0. ,0 This invention also relates to a method trolling fungus diseases, particularly fungus for condiseases of living plants which comprises applying to the locus 25 to be protected an effective amount of a compound of Formula I or Formula IX R2-Si(CH2)„Nv I ii wherein Qy, Qg and Q3 are independently H or CH^; n is 1; 3 3 7 8 5a R| and R'j are C2-C18 alkyl, C3-C6 cycloalkyl, naphthyl, or R where and R5 are independently -H; halogen; -0CH3; -OCF3; -SCH3; -S02CH3; phenyl; phenyl substituted with halogen and/or C3-c4 alkyl and/or -CF3; phenoxy; phenoxy substituted with halogen and/or alkyl and/or -CF3; -CF3; Cj-C4 alkyl; or cyelohexyl; R2 and R3 are independently Cj-C6 alkyl, C3C6 cycloalkyl, ORg, or where Rfi is H or CpC^ alkyl, with the proviso that both R2 and R3 may not be OH; and R2 and R3 together may be a 1,2- or 1,3- or 1,4-glycol bridge or a 1,4 unsaturated glycol bridge substituted by up to four alkyl groups r7-R^q that have a total of up to four carbon atoms. or or or 378 5b When Rj or R-j is OH, Formula I and Formula II are understood to include the disiloxane: ?2 *2 *2 ?2 RySi-0. ——Si-R^ or Rj-Si-0- -Si-R CH, °2 CH, V'N °2 CK2 yy* CH_ y/ This invention also relates to salts of compounds of Formula I and Formula II with protic acids and complexes with metal ions. 3 3 /8 Preferred for their high activity and/or favorable ease of synthesis are compounds of the generic scope wherein Qj « 02 H.

More preferred for their higher activity and/or more favorable ease of synthesis are compounds of the preferred scope wherein - .A., RJ RJ R2 is Cj-C4 alkyl or and Rj is Cj-C^ alkyl.

Most preferred for their highest activity and/or most favorable ease of synthesis are compounds of the more preferred scope wherein Rj and Rj are where R6 and Rj are at the para position of r or R’j, and are H, F, Cl, Br, or phenyl, and Rg is H, F, Cl, or Br; and » Rj is F, Cl, Br or may be H if Rj is not H; and R2 is »5 °r Ci-C4 alkyl; and Rj is Cj-C4 alkyl.

Specifically preferred for their excellent activity and/or most favorable ease of synthesis are the following compounds of Formula I: (Dimethyl)pheny1(1H-1,2,4-triazol-l-ylmethyllsilane; Dimethyl(4-methylphenyl)(1H-1,2,4-triazol-l-ylmethyl)silane; (4-Bromophenyl)dimethyΗ1H-1,2,4-triazol-l-ylmethy1)silane; (l,l'-Biphenyl-4-yl)dimethyl(lH-l,2,4-triazol-l-yl10 methyl)silane; (4-Chlorophenyl)dimethyl(lH-l,2,4-triazol-l-ylmethyllsilane; (2,4-Dichlorophenyl)dimethyl(lH-l,2,4-triazol-l-ylmethyDsilane; Butyl(4-chlorophenyl)methyl(1H-1,2,4-triazol-l-ylmethyl)silane; bis(4-Chlorophenyl)methyl(lH-l,2,4-triazol-l-ylmethyl)silane; Methylidiphenyl)(1H-1,2,4-triazol-l-ylmethy1)silane; [bis(4-Fluorophenyl)lmethyl(lH-l,2,4-triazol-l-ylmethyl)silane; (4-Fluorophenyl)dimethyl(lH-l,2,4-triazol-l-ylmethyl)silane; Butyl(2,4-dichlorophenyl)methyl(lH-l,2,4-triazol-l-yl25 methyl)silane; [bis(2,4-Dichlorophenyl)]methyl(lH-l,2,4-triazol-l-ylmethy1)silane; 2,4-Dichlorophenyl(methyl)phenyl(lH-l,2,4-triazol-l-ylmethyl)silane; 4-Chlorophenyl(methyl)phenyl(lH-l,2,4-triazol-l-ylmethyl)silane; 4-Fluorophenyl(methyl)phenyl(lH-l,2,4-triazol-l-ylmethyl)silane; ButyHmethyl)pheny1(1H-1,2,4-triazol-l-ylmethy1)silane; 35 Butyl(4-fluorophenyl)methy1(1H-1,2,4-triazol-l-ylmethyllsilane; β [bis(1,l'-Biphenyl-4-yl)]methy1(1Η-1,2,4-triazol-l-ylmethyDsilane; (1,1'-Biphenyl-4-yl)buty1( methyl) (1H-1,2,4-triazol-lylmethyl)silane; and (1,l'-Biphenyl-4-yl)methyl(phenyl)(lH-l,2,4-triazol-lylmethyDsilane.

Especially preferred compounds, methods, and compositions of Formula II are those compounds wherein at least one group Rj, Rj or R-j is other than lower alkyl (Cj-C4) or phenyl. In particular, the following compounds of Formula II are specifically preferred for their excellent activity and/or most favorable ease of synthesis: (1,1'-Biphenyl-4-yl)dimethyl(lH-imidazol-l-yln)ethyl)15 silane; (2,4-Dichlorophenyl)dimethyl(lH-imidazol-l-ylmethyl)silane; Butyl(2,4-dichlorophenyl)(lH-imidazol-l-ylmethyl)methylsilane; [bis(4-Fluorophenyl)](ΙΗ-imidazol-l-ylmethy1)methylsilane; [bis(2,4-Dichlorophenyl)](ΙΗ-imidazol-l-ylmethy1)methylsilane; (2,4-Dichloropheny1)(ΙΗ-imidazol-l-ylmethy1)methyl25 (phenyl)silane; (4-Chlorophenyl)(ΙΗ-imidazol-l-ylmethyDmethy1(phenyl)silane; (4-Fluorophenyl)(ΙΗ-imidazol-l-ylmethyDmethy1(phenyl)silane; (1,l'-Biphenyl-4-yl)buty1(ΙΗ-imidazol-l-ylmethy1)methylsilane; (1,1'-Biphenyl-4-yl)(ΙΗ-imidazol-l-ylmethy1)methy1(phenyl)silane; [bis(l,l-Biphenyl-4-yl)](lH-imidazol-l-ylmethyl)methyl35 silane; 3 3 Τ' 8 Butyl(4-chlorophenyl)(lH-imidazol-l-ylmethyl)methylsilane; (4-Chloropheny1)dimethy1(lH-imidazol-l-ylmethy1)silane; Dimethyl(4-fluorophenyl)(lH-lmidazol-l-ylmethyl)silane; and Butyl(4-fluorophenyl)(ΙΗ-imidazol-l-ylmethyl)methylsilane.

When and Q2are both H or both CH-j, the pro10 cess for preparing the triazole derivatives of Formula I will ordinarily produce a mixture of two triazole isomers: Formula IB Formula IA Three isomers are possible when one triazole substituent is H and the other is CHj! CH Formula IC Formula ID and Formula IE 3 3 7 8 The mixture will contain predominately the isomers of Formula IA or Formula IC; however, the isomers of Formulae IB, 10, and IE also have fungicidal activity, and separation of the isomers is not required.

For the imidazole derivatives of Formula II, isomers are produced when Q? and Qj are not the same: Formula IIA Formula IIB The isomers of Formula IIA will generally predominate; however, the isomer of Formula IIB also has fungitoxic activity and separation of the isomers is not required Detailed Description of the Invention In the following discussion, Rj is understood to represent both R^ and Rj', since all values of Rj’ are included in the definition of Rj. Further, the term azole will be used to refer to appropriately substituted 1,2,4-triazoles and imidazoles where Qp Q2 and Q3 may be H or CHj. In drawing structural formulas, the part-structure where X is N or CQj will be used to denote both triazole and imidazole ring systems.

Synthesis The compounds of this invention can be prepared from chloromethylsilanes and 1,2,4-triazole or imi5 dazole sodium salt or their methylated homologs: *2 Rj-Si-CH^l + *2 R1Si-CH,N R, Lithium and potassium azole salts may also be used. Bromomethylsilanes, iodomethylsilanes, or arylsulfonyl oxymethylsilanes may be used instead of chloromethyl15 silanes. Roughly equimolar amounts of the reagents are used (except when Rj = OR^; see below), with the azole salt often taken in 5-10% excess of theory. In addition, 1,2,4-triazole or imidazole themselves can be used if an acid acceptor is added. Suitable accep20 tors include excess azole, alkali metal alkoxides such as sodium methoxide or potassium tert-butoxide, inorganic bases such as potassium carbonate, or sodium hydride, and tertiary amines such as triethylamine. When the acid acceptor is a good nucleophile, such as sodium methoxide, an excess should be avoided to prevent undesired side reactions. Suitable solvents include polar aprotic solvents such as dimethylformamide, dimethyl sulfoxide, or acetonitrile; ethers such as tetrahydrofuran or 1,2-dimethoxyethane; and ketones such as 2-butanone. The reaction temperature can vary between 0° and 200°C, preferably between 25° and 100°C. The reaction can be conducted under elevated pressure, but it is generally preferable to operate at atmospheric pressure. The optimum temper35 ature and reaction time will vary with the concentra53378 tion and choice of reagents, and especiaily with the choice of solvent. For example, 1,2,4-triazole and sodium methoxide at roughly 2 molar concentration in dimethylformamide gives good conversion in approxi5 mately 2 hours at 80-90’C, whereas 1,2,4-triazole and potassium carbonate at roughly 1 molar concentration in 2-butanone requires 8-12 hours at reflux. The imidazole reactions are generally more rapid. In general, reaction times of 1 to 24 hours are required.

Progress of the reaction can be followed by working up aliquots for nmr analysis and following the intensities of the starting material SiCHjCl singlet near 2.9 and the product SiCH^N singlets, which are near 3.8 for compounds of Formula I and near 3.7 for compounds of Formula II.

With respect to the triazole derivatives of Formula I, the lH-l,2,4-triazol-l-ylmethyl compound as prepared above is accompanied by a minor amount of the isomeric 4H-l,2,4-triazol-4-ylmethyl compound: The ratio of isomers varies with values of R and reac25 tion conditions, with a l-substituted to 4-substituted ratio of roughly 10:1 often observed. The mono- and dimethyitriazoles give similar 4H-isomers as minor products: RpSi-CHj ch3 or When the unsubstituted silylmethyltriazole is available, metalation-methylation provides an alternate synthesis of the methylated homologs: ?2 Rj-Si-CHjH 1.

C4H9Li 2.

CHjI •2 /^N -Si-CH,N , A 2 Ά CH With respect to the imidazole derivatives of Formula II, isomers are possible only when Q2 and Qj are not the same. Two isomers result: *2 Rj-Si-CH^ CH, and Formula IIA Formula IIB The product of Formula IIA will generally predominate. If desired, the isomers may be separated by 2Q standard techniques such as crystallization, distil lation, or chromatography.

For the case where Rj = ORg In the triazole or imidazole product, the chlorines of a chloro(chloromethyl)silane can be replaced in one of two ways. In one method, at least two equivalents of the azole sodium salt can be used. An intermediate containing a very reactive silicon-azole bond forms, and reaction with water or an alcohol gives the desired oxygenated compounds: 2Q Suitable solvents and reaction conditions are the same as those outlined on pages 11, 12 and 13 for azole displacements. The temperature of alcoholysis is not critical, and warming to 50-100°C can be used to ensure complete reaction when Rg = CpC^ alkyl. For 25 Rg = H, however, hydrolysis is best conducted near room temperature to minimize disiloxane formation, recognizing that silanol-disiloxane equilibrium is possible whenever Rg = H: 3 378 The position of equilibrium and the rate at which it is established will vary with the values of R^ and R2, solvent, temperature, and the presence or absence of acidic or basic catalysts.

In the second method, the silicon-oxygen bond is formed first, followed by azole displacement as described earlier: ?2 ^2 R.-Si-CH-Cl -> R.-Si-CH,C1 n ·*· ·. i or6 Reaction of the chlorosilane with Rg0H may be conducted in almost any non-hydroxylic solvent, with ethers such as diethyl ether, 1,2-dimethoxyethane, and tetrahydrofuran or dipolar aprotic solvents such as dimethylformamide and acetonitrile being preferred. Although an acid acceptor is not required, it is preferred to add a tertiary amine such as triethylamine or pyridine. The reaction temperature may vary from 0° to 100°C, and RgOH is often taken in excess of theory. The combination of 2 equivalents of RgOH, 1.1 equivalents of triethylamine, and 0.1 equivalents of imidazole in dimethylformamide at 80° for two hours has been broadly applicable.

Extending these methods to (chloromethyl)dichlorosilanes provides dioxygenated silanes: Cl R^-Si-CHjCl Cl 0Rg Rj-Si-CHjN ORg Glycol derivatives are formed similarly, using a diol instead of two molecules of R^OH.

An alternative synthesis for alkoxy(chloromethyl)silanes involves selective replacement of one alkoxy group of a dialkoxysilane with an organometallic reagent: ?2 ?2 (R,0),5i-CH,Cl RjMgX, R,-Si-CH,C1 Ζ Ζ a | j 1 , 2 RlLi’ OR, or RjNa 6 Conditions for this displacement are as described in the next paragraph, with the added stipulation that the organometallic should be added to the dialkoxy15 silane.

The required chloromethylsilane starting materials are made from commercially available chloro(chloromethyl)dimethylsilane, chloromethyl(dichloro)methylsilane, or chloromethyltrichlorosilane: ch3 ch3 Cl-Si-CH-Cl , Cl-Si-CH,C1, '4 ι 4 n CH, Cl ?2 3 _Rj-Si-CHjCl or Cl-SiCH,Cl R3 The Si-Cl bonds in these compounds react with organolithium, organosodium, or Grignard reagents to introduce alkyl and/or aryl groups according to literature procedures, leaving the C-Cl bond intact. For the 30 silanes containing two or three Si-Cl bonds, stepwise replacements are possible, giving considerable flexibility to the values of Rj^-Rj. Bromosilanes, iodosilanes, or alkoxysilanes may be substituted for chlorosilanes in these reactions. Preferred solvents 35 for these reactions include ethers such as tetrahydro17 furan, 1,2-dimethoxyethane, and diethyl ether, or hydrocarbons such as hexane and toluene. The preferred temperature will vary between -80° and 40° depending on the nature of the organometallic reagent, how it was generated, and the solvent. For example, when aryllithium reagents are generated in tetrahydrofuran from aryl bromides using butyllithium, the mixture should be held below roughly -40° to avoid side reactions involving the bromobutane produced. If the organometallic solution is stable at higher temperatures, however, reactions may be run at -20° to 25° without competing reaction of the CHgCl group. The reaction is rapid at all temperatures, and only a short period, for example 30 to 60 minutes, is required after the reagents are combined to ensure complete reaction.

Reactions of ClSi(CH3)2CH2Cl with Grignard reagents are described by C. Eaborn and 0. C. Jeffrey, J. Chem. Soc., 1954, 4266; and a recent review on synthesis of aryltrimethylsilanes from ClSi(CH3)j, which contains experimental procedures useful for ClSKCHjIgCHgCl reactions, is that of D. Habich and F. Effenberger, Synthesis, 1979, 841. Selective introduction of one new alkyl group into Cl2Si(CHj)CH2Cl is described by V. P. Kuznetsova and R. M. Sokolovaskaya, Zh. Obshch. Khim., 1969, 1977; Chem. flbstr.. 72, 31897 p; and one aryl group may be introduced selectively as well: CHj CHj ClgSi-CHgCl + ftrLi . Cl-Si-CHgCl Ar In both cases the organometallic reagent should be added to the dichlorosllane at low temperature with good mixing for best yields.

Reactions of CljSiCHjCl with Grignard reagents are described by A. A. Zhdanov, V. I. Pakhomov, and T. Bazhanova, Zh. Obshch. Khlm., 1973, 1280; Chem. Abstr., 79, 66452 m. Adding organometallic reagents to the trichlorosilane is recommended even when three identical groups are being introduced, because adding CljSiCHjCl to an organometallic reagent is not usually successful. A single aryl group may also be introduced: CljSiCHjCl + ArLi Cl Ar-Si-CH,C1 I L.

Cl A useful modification of literature procedures applicable when R^ or R'| is an aryl group, has been developed in the present work. Instead of preforming an organolithium reagent and then combining it with a chlorosilane, it has been found that an aryl bromide and a chlorosilane such as ClSKCHjJjCHjCl may be combined in an inert solvent such as tetrahydrofuran and treated at -80 to -40° with butyllithium. Bromine-lithium exchange proceeds selectively, and the resulting aryllithium reacts with the Si-Ci bond as it is formed: CH, ArLi + Cl-Si-CH2C1 CH, LiCT Ar-Si-CH.Cl ι * S3 37 8 This reaction works equally well for aryl-substituted chlorosilanes such as ClSi(CH3)(CgH5)CH2Cl, and it can be used to introduce two aryl groups into Cl2Si(CHj)CH2Cl. In a further extension, an aryl and an n-butyl group may be introduced in one step: CHj CH3 ArBr + Cl2Si-CH2Cl 2n~C4H9L1 Ar-Si-CH2C1 Substitution of other alkyllithiums RLi for n-butyllithium provides a general route to Ar(CH3)Si(R)CH2Cl.

In the following examples, temperatures are reported in degrees Celsius. Abbreviations for nuclear magnetic resonance (nmr) spectra are s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet; peak positions are reported as parts per million downfield from internal tetramethylsilane. Infrared (ir) peak positions are given in reciprocal centimeters (cm-1). Hexanes refers to the mixture of isomers boiling 68-69°, and ether refers to diethyl ether.

Example 1 Preparation of (l,l'-Biphenyl-4-yl)(chloromethyl)dlmethylsllane_ A solution of 9.9 g (0.042 mol) of 4-bromobi5 phenyl in 50 ml of dry tetrahydrofuran was cooled to -78° under nitrogen and stirred while 26.5 ml (0.042 mol) of 1.6 molar n-butyllithium in hexane was added dropwise over 15 minutes. A thick slurry formed, and 35 ml of tetrahydrofuran was added to facilitate stir10 ring. With continued cooling, 5.9 ml (6.7 g, 0.046 mol) of chloro(chloromethyl)dimethylsilane was added over 10 minutes, giving a clear solution that was allowed to warm to room temperature. Addition of 300 ml of ether, filtration to remove precipitated lithium chloride, and evaporation of the filtrate left 13.2 g of semisolid. Redissolution in ether, filtration, and evaporation of the filtrate left 11.0 g (100X crude) of the title compound as a colorless solid, m.p. 30-40°, suitable for further reaction. Trace impuri20 ties could be removed by sublimation at 30°/0.1 mm, leaving the title compound unsublimed in 83X recovery: m.p. 37-40°; ir (NujolR) 1585, 1240, 1110, 830, 810, 750, 690 cm1; nmr (CDClj) 0.4 (6H, s), 2.9 (2H, s), 7.3-7.7 (9H, m).

Example 2 Preparation of (4-Bromophenyl)(chloromethyl)dimethylsilane 4-Bromophenylmagnesium bromide was prepared from 11.8 g (0.050 mol) of 1,4-dibromobenzene and 1.2 g (0.050 g-atom) of magnesium turnings in 75 ml of ether according to G. P. Schiemenz, Org. Syn.. Coll. Vol. 5, 496 (1973). The resulting mixture was chilled in ice under a nitrogen atmosphere while a solution of 6.6 ml (7.2 g, 0.050 mol) of chloro(chloromethyl)dimethylsllane in 10 ml of ether was added dropwise. The reaction mixture was then stirred overnight at room temperature, quenched carefully with saturated aqueous ammonium chloride, and filtered. The ether phase of the filtrate was washed with brine, dried over magnesium sulfate, and evaporated to leave 9.8 g of an oil. Distillation gave 3.8 g (29%) of the title compound as a colorless liquid: bp 97° (1 mm); ir (neat) 2950, 1575, 1475, 1370, 1250, 1065, 1010, 840, 805, 720 cm1; nmr (CDClj) 0.4 (6H, s), 2.9 (2H, s), 7.3-7.7 (4H, m).

Example 3 Preparation of Chloromethyl(4-chlorophenyl)dimethylsilane A solution of 9.6 g (0.050 mol) of 4-bromo5 chlorobenzene and 6.6 ml (7.2 g, 0.050 mol) of chloro(chloromethyl)dimethylsilane in 75 ml of tetrahydrofuran was stirred at -78° under nitrogen while 31 ml (0.050 mol) of 1.6 molar n-butyllithium in hexane was added dropwise. The resulting clear solution was allowed to warm to room temperature, diluted with ether until no more lithium chloride precipitated, and filtered. Evaporation of the filtrate left 10.6 g of a light yellow liquid, which was distilled to give 6.0 g (55%) of the title compound as a colorless liquid: bp 54-58°C (0.05 mm); ir (neat) 2910, 1560, 1470, 1370, 1250, 1080, 1010, 840, 805, 790, 740 cm-1; nmr (CDClj) 0.4 (6H, s), 2.9 (2H, $), 7.1-7.6 (4H, q).

The in situ aryllithium generation described in this example is also useful for preparing the product of Example 1. If the reaction is run at 0.5-0.7 molar in 4-bromobiphenyl and the temperature is held at -65 to -55°C during butyllithium addition, little or no solid precipitates.

Example 4 Preparation of Chloromethyl(2,4-dichlorophenyl)dlmethy1silane A solution of 17.0 g (0.075 mol) of 2,4-dichlorobromobenzene and 10.6 ml (11.6 g, 0.082 mol) of chloro(chloromethyl)dimethylsilane in 100 ml of dry tetrahydrofuran was chilled to -70° under nitrogen and stirred while 49 ml (0.079 mol) of 1.6 molar n-butyllithium in hexane was added dropwise at a rate that held the mixture below -70°. The resulting cloudy reaction mixture was allowed to warm to room temperature, poured into 400 ml of hexanes, filtered, and evaporated to leave 20.5gof yellow liquid. Distillation gave 12.6 g (66X) of the title compound as a colorless liquid: bp 83° (0.02 mm); ng4 1.5522; ir (neat) 1565, 1455, 1360, 1255, 1120, 1100, 1040, 825 cm-1; nmr (CDClj) 0.5 (6H, s), 3.1 (2H, s), 7.0-7.5 (3H, m).

Example 5 Preparation of Chloromethyl(2,6-dimethoxyphenyl)dlmethylsllane_ A solution of 25.0 g (0.181 mol) of 1,3-dime5 thoxybenzene in 250 ml of tetrahydrofuran was stirred at room temperature under nitrogen while 125 ml (0.200 mol) of 1.6 molar n-butyllithium in hexane was added dropwise over 30 minutes. The resulting mixture was refluxed 1.5 hour, giving an orange-brown solution that was cooled to 5° and stirred while 27 ml (29.4 g, 0.205 mol) of chloro(chloromethyl)dimethylsilane was added dropwise over 15 minutes. The resulting white suspension was allowed to warm to room temperature, stirred there 1 hour, diluted with ethyl acetate, poured into water, and extracted with ether. The organic layers were washed with brine, dried over magnesium sulfate, and distilled to give 37.0 g (84%) of the title compound as a colorless liquid: bp 98-110° (0.1 mm); nmr (CDClj) 0.4 (6H, s), 3.1 (2H, s), 3.7 (6H, s), 6.3 (2H, d), 7.1 (IH, m).

By varying the organolithium or Grignard reagent, the procedures of Examples 1-5 can be used to prepare the compounds of Table I. Closely related procedures are also known in the literature, for example the use of arylmagnesium chlorides by C.

Eaborn and J. C. Jeffrey, J. Chem. Soc., 1954, 4266. For compounds where R^ is a phenyl ring bearing a 2-halo substituent, an alternative to the in situ procedure of Example 4 is the special arylmagnesium iodide method of C. Eaborn, K. L. Jaura, and 0. R. M. Walton, J. Chem. Soc., 1964, 1198.

Table I CH3 x-si-ch2ci CH, X = or RJ c2h5 bp 127-128’ 10 --C4H9 bp 172° -~c12h25 n23 1.4510 —~C18H37 cyclopropyl cyclopentyl 22 1.4556 15 cyclohexyl bp 120-130° (10 mm) 1- naphthyl 2- naphthyl bp 112° (0.08 mm) phenyl bp 85-86° (3 mm) 4-fluorophenyl bp 59-60° (0.1 mm) 20 4-methoxyphenyl bp 80° (0.05 mm) 4-phenoxyphenyl bp 122° (0.03 mm) 4-(4-chlorophenoxy)phenyl ηθ 1.5773 4-(4-fluorophenoxy) phenyl 4-(4-trifluoromethylphenoxy)phenyl 25 4-(4-methylphenoxy)phenyl 4-thiomethylphenyl 4-trifluoromethylphenyl 4-methylphenyl 4-i.-propy lphenyl 30 4-t-butylphenyl 4-methylsulfonylphenyl 4-cyclohexylphenyl 4-trifluoromethoxyphenyl 4-(4-chlorophenyl)phenyl 4-(4-bromophenyl)phenyl bp 92-93° (0.05 mm) n23 1.4686 bp 96° (7 mm) n23 1.5056 m.p. 64-68° n21 1.5424 bp 55-57° (0.15 mm) Table I (continued) X = Rj or Rj 4-(4-methylpheny Ophenyl 4-(4-trifluoromethylphenyl)phenyl 4-(4-fluorophenyl)phenyl 3-phenylphenyl 3-trifluoromethylphenyl 3-chlorophenyl 2-trifluoromethylphenyl 2-phenylphenyl 2-chlorophenyl 2-methoxyphenyl 2.3- dimethylphenyl 2.3- dimethoxyphenyl 2.4- difluorophenyl 2-fluoro-4-chlorophenyl 2-chloro-4-phenylphenyl 2-fluoro-4-phenylphenyl 2- methyl-5-chlorophenyl 2,6-dimethylphenyl 3.4- dichlorophenyl 3- methyl-4-fluorophenyl 3.5- dichlorophenyl ηθ 1.5862 bp 59-62° (0.3 mm) bp 73° (0.15 mm) n^3 1.4826 n20 1.5772 bp 78-80“ (0.3 mm) n21 1.5164 n22 1.5254 bp 98“ (0.6 mm) bp 94-95° (0.25 mm) Example 6 Preparation of (l,l'-Biphenyl-4-yl)butyl(chloromethyl)methylsiiane__ The title compound can be prepared by the proce5 dure of Example 1 by substituting (butyl)chloro(chloromethyl)methylsilane for chloro(chloromethyl)dimethylsilane.

Related compounds can be prepared by the procedures of Examples 1-5, using the appropriate organoli10 thium or Grignard reagent and Cl(R2)Si(CH3)CH2Cl. The required chloromethylsilane starting materials are made from RjMgCl or R2H and Cl2Si(CH3)CH2Cl according to Examples 14 and 15, and literature procedures such as V. P. Kuznetsova and R. M. Sokolovaskaya, Zh.

Obshch. Khim., 1969, 1997.

Alternatively, both the biphenyl and butyl groups can be introduced simultaneously as follows: A solution of 23.3 g (0.10 mol) of 4-bromobiphenyl and 12.7 ml (16.4 g, 0.10 mol) of chloromethyl(dichloro)20 methylsilane in 150 ml of dry tetrahydrofuran was chilled under nitrogen to -70° and stirred while 125 ml (0.20 mol) of 1.6 molar n-butyllithium in hexane was added at a rate that held the mixture below -60°C. The resulting thin slurry was allowed to warm to room temperature, treated cautiously with 10 ml of ethyl acetate, and poured into 300 ml of water. The organic layer was separated, the aqueous phase was washed with another 100 ml of hexanes, and the combined organic phases were washed three times with water, once with brine, dried over magnesium sulfate, and evaporated to leave 33.9 g of a viscous yellow oil. Distillation gave 9.5 g (31%) of the title compound: bp 135-158° (0.1 mm); n22 1.5743; ir (neat) 3060, 3015, 2960, 2920, 2870, 1600, 1485, 1390, 1380, 1250, 1120, 1075, 1005, 875, 810, 800, 760, 700 cm-1; nmr (CDClj): 0.4 (3H, s), 0.6-1.8 (9H, m), 2.9 (2H, s) and 7.0-7.7 (9H, m).

Example 7 Preparation of Butyl(chloromethyl)(4-chlorophenyl)methylsilane_ A solution of 14.4 g (0.075 mol) of 4-bromo5 chlorobenzene and 9.5 ml (12.3 g, 0.075 mol) of chloromethyl(dichloro)methylsilane in 150 ml of tetrahydrofuran was cooled to -60° under nitrogen and stirred while 94 ml (0.15 mol) of 1.6 molar n-butyllithium in hexane was added dropwise at a rate that held the mixture between -65 and -55°. The resulting slurry was allowed to warm to room temperature, giving a solution that was diluted with hexanes until no more lithium chloride precipitated. Filtration, evaporation of the filtrate, dissolution of the residue in hexanes, refiltration, and evaporation left 19.8 g of a pale orange liquid. Distillation gave first 1.8 g (12%) of chloromethyKdibutyDmethylsilane, bp 45°C (0.05 mm), followed by 6.8 g (35%) of the title compound as a colorless liquid: bp 90°C (0.05 mm); n21 1.5246; ir (neat) 2925, 1580, 1380, 1260, 1090, 1015, 820, 740 cm1; nmr (CDClj) 0.4 (3H, s), 0.6-1.5 (9H, m), 2.9 (2H, s), 7.0-7.4 (4H, q). 5337 8 Example 8 Preparation of Chloromethyl(2,4-dichloropbenyl)methyl(phenyl)silane_ A solution of 13.6 g (0.060 mol) of 2,4-dichloro5 bromobenzene and 12.3 g (0.060 mol) of chloroCchloromethyl)methyl(phenyl)silane (prepared as in Example 14) in 85 ml of dry tetrahydrofuran was chilled to -60° under nitrogen and stirred while 38 ml (0.060 mol) of 1.6 molar n-butyllithium in hexane was added dropwise at a rate that held the mixture below -55°.

The resulting red solution was allowed to warm to room temperature, treated with 5 ml of ethyl acetate to quench any unreacted organolithium reagent, and poured into 170 ml of water. The organic layer was sepa15 rated, the aqueous phase was washed with 50 ml of hexanes, and the combined organic phases were washed three times with water and once with brine, dried over magnesium sulfate, and evaporated to leave 19.0 g of bright yellow oil. Distillation gave 8.6 g (45%) of the title compound as a colorless liquid: b.p. 125-130° (0.05 mm); n21 1.5978; ir (neat) 3030, 3060, 2960, 2930, 1570, 1540, 1460, 1430, 1365, 1260, 1120, 1100, 1040, 820, 745, 735, 705 cm1; nmr (CDClj) 0.8 (3H, s), 3.4 (2H, s), 7.2-7.9 (8H, m).

INSERT K Example 9 Preparation of Chloromethyl[bis(4-chlorophenyl)]methylsllane A solution of 19.1 g (0.10 mol) of 4-chloro5 bromobenzene in 200 ml of dry tetrahydrofuran was chilled to -60° under nitrogen and stirred while 63 ml (0.10 mol) of 1.6 molar n-butyllithium in hexane was added dropwise at a rate that held the mixture below -55°. Stirring and cooling were continued while 6.3 ml (8.2 g, 0.05 mol) of chloromethyl(dichloro)methylsilane was added dropwise at a rate that held the mixture below -50°. The resulting orange solution was allowed to warm to room temperature, and workup as in Example 8 provided 16.5 g of a pale yellow oil.

Kugelrohr distillation at 0.05 mm and an airbath temperature of 130-150°C gave 9.5 g (60%) of the title ΟΛ compound as a colorless liquid: n£ 1.5913; ir (neat) 3080, 3040, 3.020, 2960, 2930, 1580, 1490, 1380, 1260, 1085, 1015, 805, 790, 775, 740 cm1; nmr (CDClj) 0.7 (3H, s), 3.1 (2H, s), 7.2-7.7 (8H, m); analysis for C|4H^3CljSi (mw 315.70): Calculated: C, 53.26; H, 4.15; Cl, 33.69.

Found: C, 53.4; H, 4.4; Cl, 34.2. 53.5; 4.4; 34.1.

Example 10 Preparation of (Chloromethyl)bis(4-fluorophenyl)methylsllane A solution of 35 g (0.20 mol) of 4-fluorobromo5 benzene in 300 ml of dry tetrahydrofuran was chilled to -60° under nitrogen and stirred while 126 ml (0.20 mol) of 1.6 molar ri-butyllithium in hexane was added dropwise at a rate that held the mixture below -55°. Stirring and cooling were continued while 12.6 ml (16.4 g, 0.10 mol) of chloromethyl(dichloro)methylsilane was added dropwise at a rate that held the mixture below -50°. The resulting solution was allowed to warm to room temperature, and workup as in Example 8 provided 26.4 g of a clear yellow liquid. Distil15 lation gave 20.6 g (73%) of the title compound as a colorless liquid: bp 107-127° (0.1 mm); ηθ2 1.5481; nmr (COC13): 0.7 (3H, s), 3.2 (2H, s), 7.1 (4H, t, J = 9) and 7.6 (4H, d of d, J = 6 and 9).

Repeating this reaction using chloromethyKdi20 ethoxy)methylsilane instead of the dichlorosilane gave the title compound in 58% yield after distillation: bp 115-138° (0.2 mm); ηθ^ 1.5464; nmr as above.

INSERT H Example 11 Preparation of Chloromethyl(2-chlorophenyl)(4-chlorophenyDmethylsilane_ A solution of 6.3 ml (8.2 g, 0.05 mol) of chloromethyl(dichloro)methylsilane and 8.1 g (0.05 mol) of 2-bromochlorobenzene in 75 ml of dry tetra30 hydrofuran was chilled to -60° under N2 and stirred while 31 ml (0.05 mol) of 1.6 molar n-butyllithiumhexane solution was added at a rate that held the mixture below -55°. With continued cooling and stirring, 8.1 g (0.05 mol) of 4-bromochlorobenzene was added as a solid, followed by another 31 ml portion of the 1.6 3 3 7 8 molar n-butyllithium solution at a rate that held the mixture below -55°C. The resulting thin slurry was allowed to warm to room temperature, treated cautiously with 10 ml of ethyl acetate, and worked up as in Example 8 to give 15.0 g of a clear yellow oil. Distillation provided 5.9 g (37%) of the title compound: bp 150-165° (0.7 mm); n20 1.5916; ir (neat) 3060, 3020, 2960, 2920, 2870, 1580, 1560, 1490, 1420, 1380, 1255, 1125, 1115, 1085, 1035, 1015, 805, 750 cm-1; nmr (CDClj) 0.8 (3H, s), 3.3 (2H, s), 7.2-7.7 (8H, m).

The compounds of Table II are made by stepwise replacement of the Si-Ci bonds of Cl2Si(CHj)CH2Cl, according to the procedures of Examples 6-11.

Table II ch3 x-si-ch2ci *2 X = Rp RJ ^5C2»5 ΐ-εΛ cyclohexyl nrC4H9 bp 45° (0.05 mm) —C1O^21 cyclopropyl -^18^7 3-methylbutyl cyclopropyl ^C6H13 cyclohexyl cyclohexyl 1-naphthyl t-C4H? 2-naphthyl n^u phenyl phenyl U“C4h9 bp 82-90°(0.1 mm) phenyl 1,1-dimethylpropy1 4-phenylphenylC2H5 4-bromophenyl i-CjH? 4-fluorophenyl £-C4H9 bp 90-92°(0.1 mm) 4-phenoxyphenyl t-C4H9 4-t-butylphenyl cyclopentyl 3-trifluoromethylphenyl —”^4^9 3-chlorophenyl ^C5HU 2-thiomethylphenyl cyclobutyl 2-phenylphenyl i-C^ 2,4-dichloropheny1 n-C4H9 bp 109-112°(0.1 mm) 2,4-dichloropheny1 cyclopropyl 2,3-dimethy lphenyl n-CjH? 2-methy1-5-fluorophenyl cyclopentyl 2,5-dimethoxyphenyl 4-methylpentyl Table II (continued) X = Rj, Rj r2 2,6-dimethylphenyl l-mettylbutyl 5 3,5-dichlorophenyl 3,5-dichloropheny1 cyclohexyl 3-methyl-4-chlorophenyl cyclopropyl phenyl phenyl bp 104-110°(0.2 mm) 4-fluorophenyl phenyl n^2 1.5624 10 4-chlorophenyl phenyl bp 140-148°(0.1 mm) 4-bromophenyl phenyl bp 145-155°(0.1 mm) 4-phenylphenyl phenyl bp 173-178°(0.1 mm) 4-t-butylphenyl phenyl 15 4-thiomethylphenyl phenyl 4-phenoxyphenyl phenyl 4-trifluoromethoxyphenyl phenyl 4-methylsulfonylphenyl phenyl 4-cyclohexylphenyl phenyl 4-(4-fluorophenyl)phenyl phenyl 20 3-trifluoromethylphenyl phenyl 2-chlorophenyl phenyl bp 132-135°(0.1 mm) 2-methoxyphenyl phenyl 2-chloro-4-phenylphenyl phenyl ' 2-fluoro-4-phenylphenyl phenyl 25 3,5-dichlorophenyl phenyl 2,5-dimethoxypheny1 phenyl 2,6-dimethoxyphenyl phenyl 4-bromophenyl 4-bromophenyl bp 160-170°(0.1 mm) 4-phenylphenyl 4-phenylphenyl m.p. 115-117° 30 4-methoxyphenyl 4-methoxyphenyl bp 166-171°(0.1 mm) 3-tri fluoromethylphenyl 3-tri fluoromethylpheny1 2-methoxyphenyl 2-methoxyphenyl 2-chlorophenyl 2-chlorophenyl bp 135-140°(0.1 mm) 2,4-dichlorophenyl 2,4-dichlorophenyl n^1 1.5956 35 3,5-dichlorophenyl 3,5-dichlorophenyl Table II (continued) X = Rp Rj r2 2-chlarophenyl 4-fluorophenyl 4-phenylphenyl 4-chlorophenyl 4-phenylphenyl 4-fluorophenyl 4-phenylphenyl 2,4-dichlorophenyl 4-fluorophenyl 2,4-dichlorophenyl 4-chlorophenyl 2,4-dichlorophenyl 1-naphthyl 2,6-dinte thoxyphenyl 4-phenoxyphenyl 3,4-dichlorophenyl INSERT A Example 12 Preparation of (l,l’-Biphenyl-l-yl)(chloromethyl)dlethylsilane___ The title compound can be prepared by the proce5 dure of Example 1, using chlorochloromethyldiethylsilane instead of chlorochloromethyldlmethylsilane.

Similar compounds can be prepared by applying the procedures of Examples 1-5 to the appropriate organolithium or Grignard reagent and Cl(R2)Si(Rj)CH2Cl.

The required chlorochloromethyldialkylsilanes are made from CljSiCHjCl, using two equivalents of R2MgCl or R2Li when R2 * Rj (see, for example, A. A. Zhdanov, V. X. Pakhomov, and T. Bazhanova, Zh. Obshch, Khlm., 1973, 1280), or using one equivalent of RgMgCl or RjLi followed by one equivalent of RjMgCl or RjLi when R2 is not equal to Rj. 3 7 8 Example 13 Preparation of (Chloromethyl)triphenylsilane A solution of 12.6 ml (18.4 g, 0.10 mol) of (chloromethyl)trichlorosilane in 150 ml of dry ether was stirred under nitrogen and chilled in ice while 162 ml (0.30 mol) of 1.85 molar phenyllithium in cyclohexane-ether 70:30 was added dropwise at a rate that held the mixture below 15°C. The resulting slurry was stirred overnight at room temperature, treated carefully with 10 ml of ethyl acetate to quench any remaining phenyllithium, washed with water and brine, dried over magnesium sulfate, and evaporated to leave 33 g of sticky solid. Recrystallization from 30 ml of cyclohexane provided 15.8 g (51%) of the title compound as an off white solid: m.p. 112-115°C; ir (NujolR) 1420, 1110, 735, 730, 705, 695 cm-1; nmr (CDC13) 3.5 (2H, s), 7.0-7.8 (15H, m).

The compounds of Table III are made by stepwise replacement of the Si-Cl bonds of Cl3SiCH2Cl, accord20 ing to the procedures of Examples 12-13.

INSERT L 533 78 Table III *2 X-Si-CH-Cl I £ X = Rp Rj R,C2*5C2*5C2H5 10 i-C3H? i-C/*7 i-C^ £-C4H9 n-c4H9 2*8*17C2*5 cyclopentyl 2*14*29 cyclopropyl 1-methylbutyl 2“C18*37 BrC6H13 2*6*13 15 cyclopropylC2H5 s-c4h9 cyclohexyl JHC-jHy n-CjHy 1-naphthyl n-C4H9 tC4h9 2-naphthyl cyclobutyl phenyl cyclopropyl 2% 20 4-phenylphenyl n-C4H9 B-C4H9 4-phenylphenyl 2-% 2% 4-phenylphenyl cyclohexyl cyclohexyl 4-chlorophenyl n-C^ n-C4H9 4-fluorophenyl n-C^ n-CjHy 25 4-phenoxyphenyl .2*4*9 cyclohexyl 4-(4-chlorophenoxy)phenyl n-c4H9 S^4*9 4-t-butylphenyl s-C4h9 i-C4H9 3-methoxyphenylC2*5 I-C4H9 3-tri fluoromethylpheny1 S-C4H9 s-c4h9 30 2-thiomethylphenyl 3-methylbutyl 2-phenylphenyl cyclohexyl cyclohexyl 2,4-dichlorophenyl 5-c4h9 n-c4H9 2,6-dimethylpheny1 —”C4*9 1-C4H9 3,5-dichloropheny1 cyclopentyl cyclopentyl 35 3-methyl-4-chlorophenyl 2*4*9 *-C4H9 Table III (continued) X = Rr Rj r2R3C2H5 phenyl phenyl cyclohexyl phenyl phenyl •^18H37 phenyl phenyl n-C4Hg 4-chlorophenyl 4-chlorophenyl 2¾¾ 4-chlorophenyl 4-chlorophenyl 1-naphthyl 4-fluorophenyl 4-fluorophenyl cyclopropyl phenyl 4-b-butylphenyl 2rC4H9 phenyl 4-phenylphenyl t-c^ phenyl 2,4-dichlorophenyl η-Ο,Η, phenyl 3-trifluoromethylphenyl i-c^ phenyl 3,5-dichloropheny1 cyclopentyl phenyl 2,6-dimethoxypheny1 2-c14H29 4-chlorophenyl 2-fluorophenyl 2-C4H9 4-fluorophenyl 4-phenylphenyl 4-chlorophenyl 4-chlorophenyl 4-chlorophenyl 4-fluorophenyl 4-fluorophenyl 4-fluorophenyl 4-phenylphenyl 4-phenylphenyl 4-phenylphenyl 2,4-dichlorophenyl 2,4-dichlorophenyl 2,4-dichlorophenyl phenyl 4-fluorophenyl 4-fluorophenyl phenyl 4-chlorophenyl 4-chlorophenyl phenyl 4-phenylphenyl 4-phenylphenyl phenyl 2,4-dichlorophenyl 2,4-dichlorophenyl 2-naphthyl 4-methyIthiophenyl 4-methyIthiophenyl 4-chlorophenyl 2-methoxyphenyl 2-methoxyphenyl 4-chlorophenyl 3-chlorophenyl 3-chlorophenyl phenyl 2-chlorophenyl 4-fluorophenyl phenyl 4-chlorophenyl 4-phenylphenyl 1-naphthyl 4-bromophenyl 3-methylphenyl 4-phenoxyphenyl 3,5-dimethylphenyl 3,4-dichlorophenyl INSERT B Example 14 Preparation of Chloro(chloromethyl)inethyl(phenyl)sllane A solution of 12.7 ml (16.4 g, 0.10 mol) of chloromethyl(dichloro)methylsilane in 200 ml of ether was chilled to -70° under nitrogen and stirred vigorously while a mixture of 55 ml (0.10 mol) of 1.8 molar phenyllithium in 30:70 ether-cyclohexane and 55 ml of ether was added dropwise at a rate that kept the mixture below -70°. The resulting slurry was stirred and warmed to room temperature, then allowed to stand overnight. Filtration and evaporation of the filtrate left 20.4 g of a golden oil, which was distilled to give 14.6 g (71%) of the title compound as a colorless liquid: bp 71-74° (0.6 mm); ηθ3 1.5337; ir (neat) 3080, 3060, 2980, 2930, 1590, 1430, 1260, 1120, 820, 790, 740, 700 cm-1; nmr (CDClj) 0.8 (3H, s), 3.1 (2H, s), 7.3-7.6 (3H, m), 7.6-7.8 (2H, m).

INSERT M Example 15 Preparation of (l,l'-Biphenyl-4-yl)chloro(chloromethyDmethylsllane The title compound can be prepared by reaction of equimolar quantities of 4-bromobiphenyl, chloromethyldichloro(methyl)silane, and n-butyllithium according to the procedure of Example 3.

The compounds of Table IV can be prepared using the procedures of Examples 14 and 15.

Table IV X-Si-CH-Cl I * Cl X = Rp R· r2C2H5 CHj I-C4H9 CHj CHj --C12H25C2H5 —-C18^37 —-C6H13 cyclopropyl CHj cyclohexyl ch3 1-naphthyl i-C3H7 2-naphthyl cyclobutyl phenyl 4-phenylphenyl H“^4R9 4-phenylphenyl -~C6H13 4-chlorophenyl n-C4H9 4-chlorophenyl CHj 4-fluorophenyl -_C6H13 4-phenoxyphenyl cyclohexyl 4-t-butylphenyl n-CjH? 4-trifluoromethoxyphenyl CH3 4-(4-fluorophenyl)phenyl CHj 3-trifluoromethylphenyl £~C4H9 2-thiomethylphenyl cyclopentyl 2,4-dichlorophenyl CHj 2,4-dichlorophenyl £_C4H9 2-chloro-4-phenylphenyl CHj 2,3-dimethylphenyl cyclopropyl 2-methyl-5-fluorophenyl s-C4H9 2,6-dimethoxyphenyl 1,1-dimethylpropy1 Table IV (continued) X = R1, RJ 3-methyl-4-chlorophenylC2H5 3,5-dichlorophenyl n-C5H11 -~C12H25 2,4-dichlorophenyl —-C18H37 phenyl 1-naphthyl phenyl phenyl phenyl 4-fluorophenyl phenyl 4-chlorophenyl phenyl 4-phenylphenyl phenyl 4-t-butylphenyl phenyl 3-fluorophenyl phenyl 2-methoxyphenyl phenyl 2-chlorophenyl phenyl 2,4-dichlorophenyl phenyl 3,5-dichlorophenyl phenyl 4-fluorophenyl 4-fluorophenyl 4-chlorophenyl 4-chlorophenyl 4-phenylphenyl 4-phenylphenyl 2,4-dichlorophenyl 2,4-dichlorophenyl 3-trifluoromethylphenyl 3-trifluromethylphenyl 2-methoxyphenyl 2-methoxyphenyl 2-chlorophenyl 4-fluorophenyl 3-trifluoromethylphenyl 4-t-butylphenyl 2-fluoro-4-chlorophenyl 4-bromophenyl 2,3-dimethylpheny1 4-methylthiophenyl 2,6-dimethoxyphenyl 4-methoxyphenyl 3,4-dichlorophenyl 4-methylphenyl INSERT C Example 16 Preparation of ChloromethyKmethoxy)methyl(phenyl)sllane___ A solution of 1.6 ml (1.3 g, 0.040 mol) of methanol and 3.0 ml (2.2 g, 0.022 mol) of triethylamine in 100 ml of ether was stirred while a solution of 4.1 g (0.020 mol) of chloro(chloromethyl)methyl(phenyl)silane in 10 ml of ether was added dropwise.

The resulting slurry was refluxed for 2 hours, cooled, washed with water, 0.1 N aqueous HCl, saturated aqueous NaHC03, water, and brine, dried over magnesium sulfate, and evaporated to leave 3.2 g of a pale yellow liquid. Distillation provided 1.7 g (42%) of the title compound as a colorless liquid: bp 46-49° (0.05 mm); n22 1.5207; nmr (CDClj): 0.5 (3H, s), 3.0 (2H, s), 3.5 (3H, s) and 7.3-7.8 (5H, m).

Example 17 Preparation of Chloromethyl(l,l-dimethylethoxy)methyl20 (phenyl)silane____________ A mixture of 15.4 g (0.075 mol) of chloro(chloro methyl)methyl(phenyl)silane, 14 ml (11.1 g, 0.15 mol) of t-butanol, 11.5 ml (8.3 g, 0.082 g) of triethylamine, and 0.5 g (0.008 mol) of imidazole in 60 ml of dimethylformamide was stirred at 80° for 2 hours. The resulting slurry was cooled, poured into 200 ml of water, and extracted with ether. The ether extracts were washed three times with water, followed by 0.1 N aqueous HCl, saturated aqueous NaHCOj, and brine, dried over magnesium sulfate, and evaporated to leave 14.0 g of a pale orange oil. Distillation provided 11.9 g (65%) of the title compound: bp 78-82“ (0.2 mm); n21 1.5010; ir (neat) 3080, 3060, 2990, 2940, 1600, 1435, 1395, 1370, 1260, 1245, 1195, 1125, 1060, 1030, 815, 790, 740, 725, 705, 650 cm-1; nmr (CDClj): 0.5 (3H, s), 1.3 (9H, s), 2.9 (2H, s) and 7.3-7.8 (5H, m).

INSERT N Example 18 Preparation of Chloromethyl(ethoxy)methyl(phenyl)silane A solution of 18.2 ml (18.2 g, 0.10 mol) of chloromethyl(diethoxy)methylsilane in 200 ml of dry ether was stirred vigorously under N2 and chilled while 56 ml (0.10 mol) of 1.8 molar phenyllithium in 70:30 cyclohexane-ether was added at a rate that held the mixture below -50°. The resulting slurry was allowed to warm to room temperature, treated cau10 tiously with 10 ml of ethyl acetate, washed with water and brine, dried over magnesium sulfate, and evaporated to leave 16.8 g of a golden yellow liquid. Distillation provided 9.5 g (44%) of the title compound as a colorless liquid: bp 80-84° (0.1 mm); ηθ° 1.5144; nmr (CDClj) 0.5 (3H, s), 1.2 (3H, t, J = 7), 3.0 (2H, s), 3.8 (2H, q, J = 7), 7.2-7.8 (5H, m).

The compounds of Table V can be prepared using the procedures of Examples 16-18.

Table V X-S1-CH-C1 5 0„6 X = Rj, Rj r2R6 CHj CHj W9 CHj i-C4H9 ch3C2H5 £^12^25 ^5 CHj £^18^7 £-¾ CHj cyclopropyl CHj s-c4h9 cyclohexyl CHj CHj 1-naphthyl 1-^7 1-^7 2-naphthyl cyclobutyl £-CjH7 phenyl CH3 H phenyl ch3 i-CjH? bp 72-76°(0.1 mm) phenyl 1“C4H9 H 4-phenylphenyl n^C^H^ CHj 4-phenylphenyl iC4H9 H 4-phenylphenyl CHj c2h5 4-phenylphenyl CHj £C4H9 4-chlorophenyl nrC4H9 £“C4H9 4-chlorophenyl CH3 CHj 4-chlorophenyl CH3 c2h5 4-fluorophenyl £-% n-CjH, 4-fluOrophenyl CHj ^5 4-phenoxyphenyl cyclohexyl iC4H9 4-t-butylphenyl £-^7 £-C4H9 3-trlfluoromethylphenyl i”^4R9 H 2-methylthiophenyl cyclopentylC2h5 2,4-dichlorophenyl CH3 CHj 2,4-dichlorophenyl CH3 c2h5 2,4-dichloropheny1 ch3 t-C4H9 Table V (continued) X = Rp RJ % 2,4-dichlorophenyl b-c4h9C2H5 2,3-dimethylphenyl cyclopropyl i-C3H7 2-methy1-5-fluoropheny1 —C4H9 n-C^7 2,6-dimethoxyphenyl 1,1-dimethylpropyl H 3-methyl-4-chlorophenylC2H5 ch3 3,5-dichlorophenyl £^11C2H5 f>c12H25 2,4-dichlorophenyl t-C4H9 £~C18H37 phenyl ch3 1-naphthyl phenyl ^5 phenyl phenyl 1-C4H9 4-fluorophenyl phenyl ch3 4-chlorophenyl phenyl n-C.jH7 4-phenylphenyl phenyl c^5 4-phenylphenyl phenyl S-C4H9 4-t>butylphenyl phenyl --^4^9 3-fluorophenyl phenyl ^5 2-methoxyphenyl phenyl H 2-chlorophenyl phenyl ch3 2,4-dichlorophenyl phenyl --C3H7 3,5-dichlorophenyl phenyl Π—C^Hy 4-fluorophenyl 4-fluorophenyl t-C4H9 4-fluorophenyl 4-fluorophenylC2*5 4-chlorophenyl 4-chlorophenyl CHj 4-chlorophenyl 4-chlorophenyl ^5 4-phenylphenyl 4-phenylphenyl ch3 2,4-dichloropheny1 2,4-dichlorophenylC2h5 3-trifluoromethylphenyl 3-trifluoromethylphenyl i-C4H9 2-methoxyphenyl 2-methoxyphenyl H 2-chlorophenyl 4-fluorophenyl H 3-tri fluoromethylpheny1 4-t-butylphenyl H-CaH9 2-fluoro-4-chlorophenyl 4-bromophenyl iC3H7 2,3-dimethylphenyl 4-methy 1thiophenyl ^5 Table V (continued) 2,6-dimethoxypheny1 4-methoxyphenyl H 5 3,4-dichlorophenyl 4-methylphenyl i-C^Hg INSERT D Example 19 Preparation of (l,l'-Biphenyl-4-yl)dimethyl(lH-l,2,4triazol-l-y lmethy Dsilane_ A mixture of 2.6 g (0.010 mol) of (l,l’-biphenyl5 4-yl)chloromethyldimethylsilane and 1.1 g (0.012 mol) of 1,2,4-triazole sodium salt in 5 ml of dimethylformamide was warmed to 80-90° for 2 hours, cooled, diluted with water, and extracted with ether. The ether solution was washed with water and brine, dried over magnesium sulfate, and evaporated to leave 2.3 g of colorless solid, m.p. 79-86°. Recrystallization from a mixture of 25 ml of hexanes and 2 ml of ethyl acetate gave 1.1 g (38%) of the title compound: m.p. 92-93°; ir (NujolR) 1255, 1130, 1000, 825, 760, 695 cm1; nmr (CDC13) 0.4 (6H, s), 3.9 (2H, s), 7.2-7.7 (9H, m), 7.8 (IH, s), 7.9 (IH, s); analysis for C17H19N3Si (mw 293-43): Calculated C, 69.58; H, 6.53; N, 14.32; Found C, 70.0; H, 6.6; N, 13.9; 69.8; 6.7; 13.8.

An equimolar mixture of 1,2,4-triazole and sodium methoxide can be used instead of preformed triazole sodium salt. Note that these reagents must be combined before the silane is added, since chloro25 methylsilanes react very vigorously with sodium methoxide in dimethylformamide, giving undesired products.

Example 20 Isolation of (l,l'-Biphenyl-4-yl)dimethyl(4H-l,2,4triazol-4-ylmethyl)silane_ A 5 g sample of once-crystallized 1, l*-(biphenyl· 4-yl)dimethyl(lH-l,2,4-triazol-l-ylmethyl)silane, prepared as in Example 14 using sodium methoxide-1,2,4triazole, was subjected to high pressure liquid chroma tography (Waters Prep PAK-500 silica gel cartridge, 250 ml per minute flow rate). Elution with ethyl ace10 tate-hexane 50:50 removed first some minor impurities and then provided the pure lH-l,2,4-triazol-l-ylmethyl compound, m.p. 99-100°. Continued elution with ethyl acetate-acetonitrile 80:20 provided a small amount of the title compound as a colorless solid: m.p. 130-133°C; nmr (CDClj) 0.4 (6H, s), 3.7 (2H, s), 7.2-7.7 (9H, m), 7.9 (2H, s); microanalysis for C17H19N3Si 293·43)*· Calculated: C, 69.58; H, 6.53; N, 14.32.

Found: C, 69.0; H, 6.7; N, 13.9. 69.3; 6.7; 14.2.

Example 21 Preparation of Dlmethyl(phenyl)(lH-l,2,4-triazol-l-ylmethyDsilane_ A mixture of 9.0 ml (9.2 g, 0.050 mol) of chloro5 methyldimethylphenylsilane and 5.5 g (0.060 mol) of 1,2,4-triazole sodium salt in 25 ml of dimethylformamide was stirred and warmed to 90-95°C for 2 hours, coaled, diluted with water, and extracted with ether. The ether solution was washed with water and brine, dried over magnesium sulfate, and evaporated to leave 8.1 g (75%) of a pale brown oil, n22 1.5350, containing the title compound and minor impurities as judged by nmr. A purer sample was obtained by distillation: bp 99° (0.02 mm); n20 1.5403; nmr (COClj) 0.4 (6H, s), 3.8 (2H, s), 7.2-7.7 (5H, m), 7.7 (IH, s), 7.8 (IH, s); analysis for C11H15N3Si (mw 217.34): Calculated C, 60.78; H, 6.96; N, 19.33; Found C, 60.7; H, 7.0; N, 16.9; 60.2; H, 7.0; N, 16.8.

Example 22 Preparation of (4-Chlorophenyl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane_ A mixture of 2.2 g (0.010 mol) of chloromethyl(45 chlorophenyDdimethylsilane and 1.1 g (0.012 mol) of 1,2,4-triazole sodium salt in 5 ml of dimethylformamide was warmed to 80-90° for 2 hours, diluted with water, and extracted with ether. The ether solution was washed with water and brine, dried over magnesium sulfate, and evaporated to leave 2.1 g (83%) of the 91 title compound as a yellow liquid: n£j 1.5428; ir (neat) 1555, 1470, 1245, 1130, 1080, 1010, 835, 805, 795, 735 cm1; nmr (CDClj) 0.4 (6H, s), 3.8 (2H, s), 7.4 (4H, broad s), 7.8 (IH, s), 7.9 (IH, s).

Example 23 Preparation of (2,4-Dichlorophenyl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane_ A mixture of 5.1 g (0.020 mol) of chloromethyl20 (2,4-dichlorophenyl)dimethylsilane and 2.0 g (0.022 mol) of 1,2,4-triazole sodium salt in 10 ml of dry dimethylformamide was stirred at 80-90° for 2 hours. The resulting slurry was cooled, diluted with water, and washed with ether. The ether extracts were washed with several portions of water and once with brine, dried over magnesium sulfate, and evaporated to leave 4.6 g (81%) of the title compound as a pale yellow liquid: n23 1.5580; ir (neat) 1550, 1485, 1440, 1345, 1260, 1240, 1130, 1085, 1025, 1005, 835 cm-1; nmr (CDClj) 0.5 (6H, s), 4.1 (2H, s), 7.2-7.5 (3H, m), 7.8 (IH, s), 7.9 (IH, s). 83378 < Example 24 Preparation of bis(4-Chlorophenyl)methyl(lH-l,2,4triazol-l-ylmethyl)silane_ A mixture of 6.3 g (0.020 mol) of chloromethyl5 bis(4-chlorophenyl)methylsilane and 2.0 g (0.022 mol) of 1,2,4-triazole sodium salt in 10 ml of dry dimethylformamide was stirred at 80°C for 4 hours. The resulting slurry was cooled, diluted with water, and washed with ether. The ether extracts were washed with several portions of water and once with brine, dried over magnesium sulfate, and evaporated to leave 5.4 g of yellow oil. Kugelrohr distillation at 120-150° (airbath)/0.05 mm gave 4.0 g (58%) of the title compound as a pale yellow oil: n^ 1.5966; nmr (CDClj) 0.7 (3H, s), 4.1 (2H, s), 7.2-7.5 (8H, m), 7.8 (IH, s), 7.9 (IH, s).

INSERT I Example 25 Preparation of bis(4-Fluorophenyl)methyl(lH-l,2,4triazol-l-ylmethyDsilane _ A mixture of 4.2 g (0.015 mol) of (chloromethyl)bis(4-fluorophenyl)methylsilane and 1.4 g (0.015 mol) of 1,2,4-triazole sodium salt in 8 ml of dimethylformamide was stirred at 80° for 2 hours. The resulting slurry was cooled, diluted with water, and worked up as in Example 24 to give 4.0 g of a pale yellow oil. Impurities were removed by Kugelrohr distillation at 120-125° (0.05 mm), leaving behind 2.3 g (49%) of the title compound as a yellow oil: n^ 1.5538; ir (neat) 3065, 3030, 2960, 2925, 1590, 1500, 1270, 1235, 1165, 1110, 1010, 830, 790 cm-1; nmr (CDClj): 0.7 (3H, s), 4.2 (2H, s), 7.1 (4H, t, J = 9), 7.5 (4H, d of d, = 6 and 9), 7.8 (IH, s) and 7.9 (IH, s).

By applying the procedures of Examples 19 and 21-25 to appropriate chloromethylsilanes, the compounds of Table VI in which Q1=Q2=H can be prepared.

INSERT J Table VI R2 Rj-Si-CHoN c2»5 R^ ch3 CHj ηθ2 1.4713 —”^3H7 ch3 CHj IO n-c4H9 CHj CHj njy 1.4687 iC4H9 ch3 CHj ^12H25 CHj CHj r^3 1.4626 £-C14H29 CHj CHj 2-C18H37 CHj CHj r^1 1.4597 cyclopropyl CHj CHj cyclobutyl CHj CHj cyclopentyl CHj CHj cyclohexyl CHj CHj n22 1.4906 1-naphthyl CHj CHj n^3 1.6051 2-naphthyl CHj CHj 4-bromophenyl CHj CHj n20 1.5647 4-fluorophenyl CHj CHj bp 108° (0.2 mm) 4-methoxyphenyl CHj CHj r%6 1.5401 4-phenoxyphenyl CHj CHj n22 1.5754 4-(4-chlorophenoxy)phenyl CHj CHj n^2 1.5703 4-(4-fluorophenoxy)phenyl CHj CHj 4-(4-trlfluoromethylphenoxy)pheny1 'CHj CHj 4-(4-methylphenoxy)phenyl CHj CHj 4-thiomethylphenyl CHj CHj n23 1.5790 4-trifluoromethylphenyl CHj CHj n^2 1.4909 4-methylphenyl CHj CHj r^1 1.5350 Table VI (continued) ^1 «2 5 4-methylsulfonylphenyl CHj 0*3 „21 no 4-i-propylphenylc*3 CH3 4-t-butylphenylC*3 CHj „23 d 4-cyclohexylphenyl ch3 CHj „21 ηθ 10 4-tri fluoromethoxyphenyl CHj oh3 „22 % 4-(4-chlorophenyl)phenyl ch3 ch3 4-(4-bromopheny1)phenyl “3 C*3 „22 % 4-(4-methylphenyl)phenyl ch3 CH, 4-(4-trifluoromethylphenyl)phenyl ch3 OH3 15 4-(4-fluorophenyl)phenyl «3 CH3 3-phenylphenyl °*3 *3 „21 % 3-trifluoromethylphenyl CHj c*3 „20 no 3-chlorophenyl ch3 0*3 m.p. 20 2-trifluoromethylphenylCH3 CH3 „23 n0 ' 2-phenylphenyl CHj ch3 22 nD 2-chlorophenyl CH3 C*3 22 nD 2-methoxyphenyl 0*3 CH3 „21 n0 25 2,3-dimethylpheny1 c*3 CHj 2,3-dimethoxyphenyl 0*3c*3 „22 no 2,4-di fluorophenyl ch3 CHj 2-fluoro-4-chlorophenyl % CHj 2-chloro-4~fluorophenyl ch3 CHj 30 2-chloro-4-phenylphenyl ch3 CHj 2-fluoro-4-phenylphenyl ch, CHj 2-methyl-5-chlorophenyl c*3 CHj 2,6-dimethoxyphenyl CH3 CHj „23 % 35 2,6-dimethylphenyl ch3 CHj .5538 ..5125 .5235 ..4768 L.5802 ..5939 ..4845 37-43° L.4964 1.5900 1.5442 1.5216 1.5322 1.5404 Table VI (continued) r2R3 3,4-dichlorophenyl CH3 CH3 n^2 1.5602 3-methy1-4-fluorophenyl ch3 CHj 3,5-dichlorophenyl ch3 ch3 m.p. 63-69° ^5 ^5 ch3 —_C3H7 cyclohexyl ch3 2-C4H9 ch3 n22 1.4672 2-c10H21 cyclopropyl CHj JQ-c12H25 n-C-jH? ch3 •2C14H29 T-C3H7 CHj £-C18H37 3-methylbutyl CHj cyclopropyl £-^13 ch3 cyclopentyl cylopentyl ch3 cyclohexyl cyclohexyl % 1-naphthyl 2-C4H9 CHj 1-naphthyl t-c4H9 CHj 2-naphthyl 2-6^11 CHj phenyl n-CjHy ch3 phenyl 2-CaH9 ch. n21 1.5297 phenyl 1,1-dimethylpropyl CHj phenyl ^13 CH3 4-phenylphenyl ^5 CHj 4-phenylphenyl 2-caH9 CHj ηθ2 1.5838 4-bromophenyl i-C3H7 CHj 4-chlorophenyl 2-C4H9 ch3 21 ng 1.5344 4-fluorophenyl 2^6489 ch3 n22 1.5120 4-phenoxyphenyl A-C4H9 CHj 4-i-propylphenyl cyclopropyl CHj 4-t-butylphenyl i-C4H9 CHj 3-phenylphenyl i-c4H9 CHj 3-tri fluoromethylpheny1 s-C4H9 CH3 53373 Table VI (continued) 1 «2 3-chlorophenyl ΰ^ΙΙ ch3 2-methoxyphenyl t-C4H9 CH3 2-thiomethylphenyl cyclobutyl CH3 2-phenylphenyl 1-C4H9 CH3 2,4-dichlorophenyl 2-cAH9 CH, n23 1.5411 2,4-dichlorophenyl cyclopropyl CH, 2,3-dimethylphenyl CH, 2-methyl-5-fluorophsnyl cyclopentyl CH3 2,5-dimethoxyphenyl 4-methylpentyl CH3 2,6-dimethylphenyl 1-methylbutyl 3 3,4-dichlorophenyl *3 3,5-dichlorophenyl CH3 3,5-dichlorophenyl cyclohexyl “3 3-methy1-4-chlorophenyl cyclopropyl 0,3 phenyl phenyl CH, tl£2 1.5852 4-fluorophenyl phenyl CH, n20 1.5718 4-chlorophenyl phenyl CH, 22 Πρ 1.5926 4-bromophenyl phenyl CH, 22 ηθ 1.6076 4-phenylphenyl phenyl CH, η21 1.6328 4-t-butylphenyl phenyl CH, 4-thiomethylphenyl phenyl *3 4-phenoxyphenyl phenyl CH3 4-trifluoromethoxyphenyl phenyl CH3 4-methylsulfonylphenyl phenyl “3 4-cyclohexylphenyl phenyl CH, 4-(4-fluoropheriyl)phenyl phenyl 3-trifluoromethylphenyl phenyl 2-chlorophenyl phenyl CH, 20 ηθ 1.5742 2-methoxyphenyl phenyl CH, Table VI (continued) 2.4- dichlorophenyl 2-chloro-4-phenylphenyl 2- fluoro-4-phenylphenyl 3.5- dichlorophenyl 2.5- dimethoxyphenyl 2.6- dimethoxyphenyl 4-bromophenyl 4-phenylphenyl 4-methoxyphenyl 3- trifluoromethylphenyl 2-chlorophenyl 2-methoxyphenyl 2.4- dichlorophenyl 3.5- dichlorophenyl 2-chlorophenyl 2-chlorophenyl 4- phenylphenyl 4-phenylphenyl 4-phenylphenyl 4-fluorophenyl 4-chlorophenyl 1-naphthyl 4-phenoxyphenyl ^5 i-C3H7 η-ΟθΗι? -'C14H29 ^18^7 cyclopropyl phenyl phenyl phenyl phenyl phenyl phenyl 4-bromophenyl 4-phenylphenyl 4-methoxyphenyl 3- trifluoromethylphenyl 2-chlorophenyl 2-methoxyphenyl 2.4- dichlorophenyl 3.5- dichlorophenyl 4- chlorophenyl 4-fluorophenyl 4-chlorophenyl 4-fluorophenyl 2,4-dichlorophenyl 2,4-dichlorophenyl 2.4- dichlorophenyl 2.6- dimethoxyphenyl 3.4- dichlorophenyl ^5 1-^7 ^5 cyclopropyl C2H5 CHj n23 1.5941 CH3 CHj ch3 CHj CHj n^1 1.6245 CHj m.p. 42-46° CHj n^1 1.5890 CHj CHj n21 1.5965 CHj CHj n^2 1.6009 CHj CHj n20 1.5918 CH, % CH3 ch3 CH3 CHj CH3 CH3C2H5 1-^7 D-C4H9 cyclopentyl 1-methylbutyl *-C6H13 £“C4H9 Table VI (continued) ii R, cyclohexyl £-C3H7 I1-C3H7 1-naphthyl £C4H9 2-naphthyl £-CaH9 cyclobutyl phenyl cyclopropyl £-¾ 4-phenylphenyl ^5 C2H5 4-phenylphenyl £-C4H9 £-C4H9 4-phenylphenyl £“C6H13 £•^13 4-phenylphenyl cyclohexyl cyclohexyl 4-chlorophenyl £-C4H9 £-C4H9 4-fluorophenyl £<^7 n-CjHy 4-phenoxyphenyl £7^9 cyclohexyl 4-(4-chlorophenoxy)phenyl £**4^9 DrC4H9 4-t-butylphenyl £C4H9 I-C4H9 3-tnethoxyphenylC2»5 1-C4H9 3-trifluoromethylphenyl ®-c4h9 £~C4H9 2-thiomethylphenyl i-cA 3-methylbutyl 2-phenylphenyl cyclohexyl cyclohexyl 2,4-dichlorophenyl £SH9 J>c4h9 2,6-dimethylphenyl t-C4H9 3,5-dichlorophenyl cyclopentyl cyclopentyl 3-methyl-4-chlorophenyl S-C4H9 2-methy1-5-fluorophenyl 2-c4h9C2»5 phenyl phenyl cyclohexyl phenyl phenyl £^18^7 phenyl phenyl £~^4R9 4-chlorophenyl 4-chlorophenyl £'C12H25 4-chlorophenyl 4-chlorophenyl 1-naphthyl 4-fluorophenyl 4-fluorophenyl cyclopropyl phenyl 4-t-butylphenyl £“C4H9 phenyl 4-phenylphenyl t-C4H9 phenyl 2,4-dichlorophenyl n-CsH? phenyl 3-trifluoromethylphenyl eo Table VI (continued) ^2 R^ i-C4H9 phenyl 3,5-dichlorophenyl cyclopentyl phenyl 2,6-dimethoxy phenyl BC14H29 4-chlorophenyl 2-fluorophenyl n-C4H9 4-fluorophenyl 4-phenylphenyl phenyl phenyl phenyl m.p. 118 4-chlorophenyl 4-chlorophenyl 4-chlorophenyl 4-fluorophenyl 4-fluorophenyl 4-fluorophenyl 4-phenylphenyl 4-phenylphenyl 4-phenylphenyl 2,4-dichlorophenyl 2,4-dichlorophenyl 2,4-dichloropheny1 phenyl 4-fluorophenyl 4-fluorophenyl phenyl 4-chlorophenyl 4-chlorophenyl phenyl 4-phenylphenyl 4-phenylphenyl phenyl 2,4-dichlorophenyl 2,4-d ichlorophenyl 2-naphthyl 4-methylthiophenyl 4-methylthiophenyl 4-chlorophenyl 2-methoxyphenyl 2-methoxyphenyl 4-chlorophenyl 3-chlorophenyl 3-chlorophenyl phenyl 2-chlorophenyl 4-fluorophenyl phenyl 4-chlorophenyl 4-phenylphenyl 1-naphthyl 4-bromophenyl 3-methylphenyl 4-phenoxyphenyl 3,5-dimethylphenyl 3,4-dichlorophenyl INSERT E Example 26 Preparation of (3,5-Dimethyl-lH-l,2,4-triazol-l-ylmethyl)[bis(4-fluorophenyl)]methylsilane_ The title compound is prepared by applying the procedure of Example 25 to equimolar quantities of chloromethyl[bis(4-fluorophenyl)]methylsilane and 3,5-dimethyl-l,2,4-triazole sodium salt.

Related compounds may be made by substituting salts of 3-methyl-l,2,4-triazole for the 3,5-dimethyl10 triazole salt.

Example 27 Preparation of (l,l'-Biphenyl-4-yl)dimethyl(3-methyl1H-1,2,4-triazol-l-ylmethyl)silane_ A solution of 5.9 g (0.020 mol) of (l.l'-biphenyl-4-yl)dimethyl(lH-l,2,4-triazol-l-ylmethyl)silane in 40 ml of dry tetrahydrofuran was chilled to -40° under N2 and stirred while 12.5 ml (0.020 mol) of 1.6 molar n-butyllithium in hexane was added dropwise.

The resulting yellow solution was stirred another 15 minutes at -40°, treated with 1.9 ml (4.2 g, 0.030 mol) of methyl iodide, and allowed to warm to room temperature. The resulting solution was diluted with water and extracted with hexanes. Washing the organic extracts with water and brine, drying over magnesium sulfate, and evaporation gave 5.7 g of solid, which was purified by dry-column chromatography over silica gel (ethyl acetate elution) to give 1.1 g of crude product. Recrystallization from 12 ml of 3:1 hexanes30 ethyl acetate then gave 0.97 g (16%) of the title compound as an off white solid: m.p. 95-98°; ir (NujolR) 1590, 1270, 1250, 1180, 1120, 830, 765, 700 cm1; nmr (CDClj) 0.5 (6H, s), 2.2 (3H, s), 3.7 (2H, s), 7.2-7.7 (9H, m), 7.8 (IH, s).

Although the indicated structure is preferred for steric reasons, the position of the methyl group on the triazole ring has not been proven, and it is possible that the product is (l,l'-biphenyl-4-yl)5 dimethy1(5-methyl-lH-l,2,4-triazol-l-ylmethyl)silane.

The procedures of Examples 26 and 27 may be used to prepare the compounds of Table VII.

Table VII RpSl· Q1 λΝc' CH-N | Rl h 5C2H5 % CHj CHj CH ^18^7CH3CH3 H ch3 cyclohexylCH3CH3 CH, CH 1-naphthyl CHj CH, CHj CH phenyl CHj CHj H ch’ phenyl CHj CH, CHj Η 4-phenylphenylCH3 CHj CHj 4-(4-fluorophenyl)phenyl CHj CH, CH, CH 4-phenoxyphenyl <*3 CHjCH3 % 3-trifluoromethylphenylCH3 CH CHj CH, 2-methoxyphenyl CHj % CH, 3 CH, 2,4-dichlorophenyl CHjCH3 CH, 2-chloro-4-phenylphenylCH3 * CHjCH3 CH phenyl ^-C4H9 CHjCH3 % 4-phenylphenyl S-C4H9 CHj H % 2,4-dichlorophenyl I!-C6Hi3 CHj CH, CH, 4-(4-chlorophenoxy)phenyl cyclohexyl CHj chJCH3 phenyl phenyl ch3 Η CH, 4-fluorophenyl phenyl CH, CH, CH 4-fluorophenyl phenyl CH . H CH 4-chlorophenyl phenyl CH H 3 CH 4-fluorophenyl 4-fluorophenyl CH H CH 4-fluorophenyl 4-fluorophenyl CH CH, J H 4-chlorophenyl 4-chlorophenyl CH H CH, 4-chlorophenyl 4-chlorophenyl CH CH, CH 2-chlorophenyl 4-chlorophenyl CH j H % Table VII (continued) ?i ih ih 2,4-dichlorophenyl 2,4-dichlorophenyl CHj 0*3 CHj 2c18H37 £•6^13 n-C^u CHj CHj 1-naphthyl n-C4H9 2C4H9 H CHj phenyl phenyl phenyl H CHj phenyl phenyl phenyl CHj H phenyl phenyl phenyl CHj CHj Example 28 Preparation of the 1:1 complex of (l,l'-Biphenyl-4-yl)dimethyl(lH-l,2,4-triazol-l-ylmethyl)silane and Cuprous Chloride_ A mixture of 5.0 g (0.017 mol) of (l,l‘-biphenyl4-yl)dimethyl(lH-l,2,4-triazol-l-ylmethyl)silane and 1.7 g (0.017 mol) of cuprous chloride in 170 ml of tetrahydrofuran was refluxed under N2 for 30 minutes, and the resulting deep green solution was evaporated to leave the title compound as a dark greenish-brown solid: m.p. 85-90°; ir (NujolR) 3110, 1590, 1280, 1250, 1120, 1010, 990, 840, 825, 760, 700 cm-1.

The following metal complexes of (l,l'-biphenyl4-yl)dimethyK1H-1,2,4-triazol-4-ylmethyl)silane were prepared similarly: 1:1 Complex with cupric chloride: m.p. 83-87’ 2:1 Complex with cupric chloride: m.p. 85-92° 1:1 Complex with zinc chloride: n2^ 1.5737 1:1 Complex with manganous sulfate: m.p. 244-250° (decomp.) Example 29 Preparation of the 4-Dodecylbenzenesulfonate Salt of (1,1'-Bipheny1-4-y1)dimethy1(1H-1,2,4-tr iazol-1-y125 methyDsilane A solution of 1.0 g (0.0034 mol) of (l,l'-biphenyl-4-yl)dimethyl(lH-l,2,4-triazol-l-ylmethyl)silane in 10 ml of dichloromethane was combined with a solution of 1.1 g (0.0034 mol) of 4-dodecylbenzenesul30 fonic acid in 10 ml of dichloromethane. The resulting solution was evaporated to leave the title salt as a viscous yellow oil: ηθθ 1.5645; ir (neat) 3110, 3050, 3020, 2960, 2920, 2850, 2570, 1920, 1600, 1545, 1485, 1455, 1405, 1250, 1225, 1165, 1120, 1030, 1010, 990, 845, 825, 755, 735, 700, 670, 635 cm”1.

Example 30 Preparation of the 2:1 complex of [bis(4-Fluorophenyl)]methyl(lH-l,2,4-triazol-l-ylmethyl)silane and Cupric Chloride_ A mixture of 1.0 g (0.0032 mol) of [bis(4-fluoro phenyl)]methyi(lH-l,2,4-triazol-l-ylmethyl)silane and 0.2 g (0.0016 mol) of cupric chloride in 30 ml of tetrahydrofuran was refluxed under N? for 30 minutes and evaporated to leave the title complex as a blue10 green glass: no distinct m.p.; ir (NujolR) 1580, 1490, 1230, 1160, 1110, 830, 785 cm-1.

The 1:1 complex with cuprous chloride was prepared similarly to give a dark green glass: no distinct m.p.; ir as above.

By applying the procedures of Examples 26-28, any of the compounds of Tables VI, VII, VIII, IX, XII and XIII can be converted to salts or metal complexes.

Example 31 Preparation of (l,l-'Biphenyl-4-yl)(lH-l,2,4-triazol1-ylmethy1)(methoxy)methylsilane_ A mixture of (l,l'-biphenyl-4-yl)ohlorochloromethylmethylsilane and two equivalents of 1,2,4-triazole sodium salt in dimethylformamide is warmed to 80-90°C for 2 hours. Ten equivalents of methanol is then added, and the mixture is held at 70°C for 1 hour, cooled, diluted with water, and quickly extracted with ether. Washing the ether solution with water and brine, drying over magnesium sulfate, and evaporation leaves the title compound.

Related compounds can be made in the same way, using the appropriate chlorosilane and alcohol; for Rg = OH, water is used instead of an alcohol, and hydrolysis is conducted at 20-25°C instead of 70°.

Example 32 Preparation of (l,l-dimethylethoxy)methyl(phenyl)(IH— 1,2,4-trlazol-l-ylmethyl)silane_ A mixture of 3.6 g (0.015 mol) of chloromethyl(l,l-dimethylethoxy)methyl(phenyl)silane and 1.3 g (0.015 mol) of 1,2,4-triazole sodium salt in 8 ml of dimethylformamide was stirred at 80° for 2 hours, cooled, and poured onto water. The resulting mixture was extracted with ether, and the ether extracts were washed with water and brine, dried over magnesium sulfate, and evaporated to leave 2.7 g of a yellow oil. Chromatography on silica gel, eluting with 50:50 ethyl acetate-hexanes, provided 1.5 g (36%) of the title compound as a pale yellow oil: ηθ 1.5134; ir (neat) 3120, 3070, 3045, 2975, 2925, 1500, 1425, 1380, 1365, 1270, 1255, 1240, 1190, 1140, 1115, 1050, 1020, 1010, 830, 810, 790, 740, 700, 680 cm-1; nmr (CDClj): 0.6 (3.H, s), 1.3 (9H, s), 3.9 (2H, s), 7.3-7.7 (5H, m), 7.9 (IH, s) and 8.0 (IH, s).

The compounds of Table VIII and IX in which Ql=Q2=H can be made using the procedures of Examples 31 and 32.

INSERT 0 Table VIII ?2 R,-Si* I OR. »1 C2«5 CHj CHj 1-C4H9 CHj £-C4H9 CHj ^5 £C12H25C2h5 CHj £^18H37 CHj cyclopropyl CHj cyclohexyl CHjm3 1-naphthyl 1^7 i-C/*7 2-naphthyl cyclobutyl rwCjH7 phenyl CHj H phenyl CHj CHj phenyl CHj ^5 phenyl CHj 1-^7 phenyl 1“C4H9 H 4-phenylphenyl £-C4H9 CHj 4-phenylphenyl t-C4H9 H 4-phenylphenyl CHj CjHj 4-phenylphenyl CHj £^•489 4-chlorophenyl 57^489 4-chlorophenyl CHj ch3 4-chlorophenyl CHjε2»5 4-fluorophenyl £C6H!3 4-fluorophenyl CHj 4-phenoxyphenyl cyclohexyl i-C4H9 4-t-butylphenyl rwCjH? s-c4h9 3-trifluoromethylphenyl t-C4H9 H 2-methylthlophenyl cyclopentyl .5367 Table VIII (continued) ^6 2,4-dichlorophenyl CHj CHj 2,4-dichlorophenyl CHjC2*5 2,4-dichlorophenyl CHj t-C4H9 2,4-dichlorophenyl 2-C4H9 c^5 2,3-dimethylphenyl cyclopropyl 2-methyl-5-fluorophenyl -”C4H9 n-CjHy 2,6-dimethoxyphenyl 1,1-dimethylpropyl H 3-methyl-4-chlorophenylC2»5 CHj 3,5-dichloropheny1 ^c/'n c2h5 I>C12H25 2,4-dichlorophenyl kc4H9 £C18H37 phenyl CHj 1-naphthyl phenylC2«5 phenyl phenyl i‘C4H9 4-fluorophenyl phenyl CHj 4-chlorophenyl phenyl n-CjH? 4-phenylphenyl phenyl c^5 4-phenylphenyl phenyl ^^489 4-t-butylphenyl phenyl StC4H9 3-fluorophenyl phenylC2»5 2-methoxyphenyl phenyl H 2-chlorophenyl phenyl CHj 2,4-dichlorophenyl phenyl I-C3H7 3,5-dichlorophenyl phenyl n-CjH? 4-fluorophenyl 4-fluorophenyl t-C4H9 4-fluorophenyl 4-fluorophenyl 4-chlorophenyl 4-chlorophenyl CHj 4-chlorophenyl 4-chlorophenylC2»5 4-phenylphenyl 4-phenylphenyl CHj 2,4-dichlorophenyl 2,4-dichlorophenyl ^5 3-trifluoromethylphenyl 3-trifluoromethylphenyl iC4H9 2-methoxyphenyl 2-methoxyphenyl H 2-chlorophenyl 4-fluorophenyl H Table VIII (continued) 3-tri fluoromethylphenyl 4-t-butylphenyl 2-fluoro-4-chlorophenyl 4-bromophenyl 1-^7 2,3-dimethylphenyl 4-methylthiophenylC2»5 2,6-dimethoxyphenyl 4-methoxyphenyl - H 3,4-dichloropheny1 4-methylphenyl 1¼ Table IX ?2 RrSi-CH2N 0Rg N ?i ^6 jl 10C2*5C*3 C*j C*3 <*3 cyclohexyl CHj 1*3*7 H C*3 —*18*37 £*6*13 i-C4*9 C*3 % 1-naphthyl CHj ±*3*7 % CHj phenyl c*j 1-C4*9 H % 15 phenyl C*3 t-c^ CHj H phenyl C*3 t-C4H9% % phenyl CHj H C*3 phenyl CHj H CHj 4-phenylphenyl 1-C4H9 H CH, 20 4-phenylphenyl C*3 H % 4-phenylphenyl C*j 1*4*9 C*3 % 4-chlorophenyl CH3 £.-C4H9 H CM3 4-chlorophenyl 0*3 tc4*9C*3 c7j 4-fluorophenyl C*j t-C4*9 H CH 25 4-fluorophenyl CH3 •1*4*9 CH- C* phenyl phenylC2*5 C*3 % phenyl phenyl rnCJ-LC*3 CH 4-fluorophenyl phenyl 1*3*7 H CHj 4-fluorophenyl phenyl iC4*9 CH CH, 30 4-chlorophenyl phenyl iC3*7 J H 2,4-dichlorophenyl phenyl H CH - CH, 4-fluorophenyl 4-fluorophenyl t-C4H9 J H CH 4-fluorophenyl 4-fluorophenyl 1-C4H9 CH, j H 4-fluorophenyl 4-fluorophenyl t-CM c*; CH, 35 2-methoxyphenyl 2-methoxyphenylC2*5 CHj 3-methylphenyl 3-methylphenyl 1*4*9 H Example 33 Preparation of Chloromethyl(dlchloro)phenylsllane A solution of 25.1 ml (36.β g, 0.200 mol) of chloromethyltrlchlorosllane In 400 ml dry tetrahydro3 furan was cooled to -78’ under nitrogen and stirred vigorously while 48.0 ml (0.100 mol) of 2.1 molar phenyllithium was slowly dripped in over 1 hour.

After stirring another 30 minutes at -78° the solution was allowed to warm to room temperature and evaporated to about 200 ml. Addition of 500 ml ether, filtration to remove precipitated lithium chloride, and evaporation of the filtrate left 25.0 g of liquid. Distillation gave 6.5 g (29%) of the title compound as a colorless liquid: bp 62-82° (0.15 mm); nmr (CDClj): Example 34 Preparation of ChloromethvKdlethoxy)phenylsllane A solution of 1.0 g (0.0044 mol) of chloromethyl20 (dichloro)phenylsilane in 8 ml of absolute ethanol was cooled to 0° under nitrogen and stirred while 0.61 ml (0.445 g, 0.0044 mol) of triethylamine was slowly added, giving a slurry that was allowed to warm to room temperature. Addition of 50 ml of ether, filtra25 tion to remove precipitated triethylamine/hydrochloride, and evaporation of the filtrate left a residue which was filtered through a short silica gel column (95% petroleum ether:ethyl acetate as the eluent) to give 0.80g(73%) of the title compound as a colorless oil: nmr (CDClj): 1.25 (t, 6, J = 6Hz), 3.0 (s, 2), 3.9 (q, 4, 3 = 6Hz) and 7.2-7.9 (m, 5).

Example 35 Preparation of Chloromethyl(phenyl)bis(2-propoxy)silane A solution of 2.0 g (0.009 mol) of chloromethyl(dichloro)phenylsilane and 5 ml of 2-propanol in i5 ml of dimethylformamide was stirred under N2 while 2.5 ml (1.9 g, 0.018 mol) of triethylamine was added dropwise. The resulting slurry was warmed to 80° for 2 hours, cooled, diluted with water, and extracted with ether. The ether extracts were washed with water and brine, dried over magnesium sulfate, and evaporated to leave 2.2 g of liquid. Column chromatography over silica gel, eluting with petroleum ether, provided 1.4 g (58%) of the title compound as a colorless liquid: n22 1.4741; nmr (CDCl-j) 1.2 (12H, d, J = 6), 3.0 (2H, s), 4.3 (2H, septet, J = 6), 7.3-7.8 (5H, m).

The compounds of Tables X and XI can be made using the procedures of Examples 33-35.

Table X R1-Si-CH2C1 or6R6C2H5 1-¾ 10 2”^4R9 c2h5 —”C18H37 CHj cyclohexyl n-CjHy 1-naphthyl 1-¾ phenyl CHj 15 phenyl n-CjH? phenyl 1-¾ 4-phenylphenyl c2h5 4-phenylphenyl n-C4H9 4-fluorophenyl CHj 20 4-fluorophenylC2H5 4-chlorophenylC2H5 4-chlorophenyl i-CjH7 3-trifluoromethylphenyl 1-¾ 2-methoxyphenyl n-CjH? 25 2,3-dimethylphenyl 1-¾ 2,4-dichlorophenyl CHj 2,4-dichlorophenylC2H5 2-methoxy-5-fluorophenyl 1-CjH7 2,6-dimethoxyphenyl CHj 30 3,4-dichlorophenyl c2h5 3,5-dichlorophenyl n-C4H9 75 Table XIR1 0 0 \ / Rj-Si-CHjCl R6C2»5 -ch^h2- n-C4H9 -CH^H- £C18H37 -ch^h2ch2- cyclohexyl ?2»5 -CH2CH- 1-naphthyl -ch^:h2- phenyl -ch2ch2- phenyl ?2H5 -ch2ch- phenyl £?3H7 -CH-CH- phenyl -C(CH3)2C(CH3)2- bp 142-162°(10mm) 4-phenylphenyl -CH.^- ^5 4-phenylphenyl -CHjCH- CH, CH, | * | * 4-phenylphenyl -CH—CH- 4-fluorophenyl -CHjCHj- CHj -CH^H- ?2H5 4-fluorophenyl 4-chlorophenyl -CH2CH- 4-chlorophenyl -C(CH,)2C(CH3)2- CH, » 3 3-trifluoromethylphenyl -CHCH9C(CH,)9- S' I b !i i Table XI (continued) 2-methoxyphenyl 2.3- dimethylphenyl 2.4- dichlorophenyl 2.4- dichlorophenyl 2-methoxy-5-fluorophenyl 2,6-dimethoxypheny1 3.4- dichlorophenyl 3.5- dichlorophenyl ΰ^18Η37 phenyl phenyl phenyl phenyl 4-phenylphenyl 4-phenylphenyl 4-fluorophenyl 4-chlorophenyl 4-phenoxyphenyl 3-tri fluoromethylphenyl 2-methoxyphenyl — ,4 9 -CH^CH-CHgCHg?2H5 -CHjCHrt-C,H, — ,3 7 -CHjCHCHj CHj -CHC(CHj)2CH-ch^ch2CHj CHj -CHCHjpHCH, CH, « 3 < 3 -CH—CH-CHgCHsCHCHjCHj CHj -CHCH^CHjCH-ch2ch=chch2-C(CHj)2CH=CHC(CHj)2CHj CHj -CHCHjCHjCH-CiCHjJjCHjC^CiCHjJg-ch^ch=chch2CH, CH, I z I -CHjOsCCHj-ch2-ch=chch2-CH^CHgCHjCHjΒ-θ4Η9 -CH^CHjCHjCHCHj CHj -CHCH=CHCHCHj CHj -CHjCH—CHCH2bp 57-60° (0.15 mm) Example 36 Preparation of Phenylbis(2-propoxy)(lH-l,2,4-triazoll-ylmethyl)sllane__ The title compound can be made by applying the 5 procedure of Example 32 to chloromethyl(phenyl)bis(2-propoxy)silane: n^2 1.4962; nmr (CDClj) 1.1 (12H, d, J = 6), 4.0 (2H, s), 4.3 (2H, septet, J = 6), 7.2-8.0 (7H, m).

The compounds of Tables XXI and XIII can be made similarly.

Table ΧΠ ϊ Ql ^2 ^5 «4Η9 H H 2-C4H9 c^s H H ΰ·Ε18Η37 CHj H H cyclohexyl n-CjH, H H 1-naphthyl iC4H9 H H phenyl CHj CHj CHj phenyl n-CjH? H CHj phenyl 1-^7 CHj CHj phenyl 1-C4H9 H H 4-phenylphenyl ^5 CHj CHj 4-phenylphenyl £-^4^9 H H 4-fluorophenyl CHj H H 4-fluorophenyl ^5 H H 4-chlorophenylC2»5 H H 4-chlorophenyl i-CjH, H H 3-tri fluoromethylpheny1 s,“C4H9 CHj CHj 2-methoxyphenyl n-CjH7 H CHj 2,3-dimethylphenyl i-C4H9 CHj CHj 2,4-dichlorophenyl CHj H H 2,4-dichlorophenyl C2H5 H H 2-methoxy-5-fluorophenyl i-CjH, H H 2,6-dimethoxypheny1 CHj H H 3,4-dichlorophenyl ^5 H H 3,5-dichlorophenyl 2^^489 H H Table XIII Roz '0 Qv/°aX Rj-Si· 1 ^1 -CH2CH2- ch3 ch3 ch3 -CH^CH- Η ch3 •2C18H37 H Η 15 cyclohexylG2H5 -CHjCH- H Cl·^ 1-naphthyl -ch2ch2- ch3 Η phenyl -ch^ch2- ch3 ch3 20 phenyl ?2H5 -CH2CH- H Η phenyl η-Ο,Η? -CHjCH- Η Η phenyl -c(ch3)2c(ch3)2- Η Η 4-phenylphenyl -CH^- Η Η 25 4-phenylphenyl ?2H5 -CHjCH- Η Η 4-phenylphenyl CH, CH, -CH-CH- Η Η 4-fluorophenyl -CH2CH2- Η Η 30 4-fluorophenyl CH3 -CHjCH- Η Η 4-chlorophenyl ^5 -ch2ch- Η Η 4-chlorophenyl -C(CH3)2C(CH3)2- Η Η 35 3-trifluoromethylphenyl CH, 1 ’ -CHCH2C(CH3)2- ch3 ch3 80 Table XIII (continued)R1R6Q1 °2 2-C4H9 -CHjCH- 5 2-methoxyphenyl H ch3 2,3-dimethylphenyl -CHjCHg- ^5 ch3 ch3 10 2,4-dichlorophenyl -CHjCH- ΰ-?3Η7 -CH^CHch3 ch3 -CHCiCHjJjCH- H H 2,4-dichlorophenyl H H 2-methoxy-5-fluorophenyl H H 15 2,6-dimethoxypheny1 -CHjCRj- CH, CH, • 3 1 * -CHCHjCH- CH, CH, 1 - 1 3 H H 3,4-dichlorophenyl H H 3,5-dichlorophenyl -CH—CH- H H 20C2»5 -ch^ch«chch2ch3 ch3 ch3 ch3 --C18H37 -CHCH^CH- H ch3 phenyl -CHjCHsCHCHj,- H H phenyl -C(CH3)2CH=CHC(CH3)2ch3 ch3 -CHCHjCHgCH- H H 25 phenyl H H phenyl -CCCH-jJ^HjCH^CHjJj- H H 4-phenylphenyl -ch2ch=chch2- CH, CH, , 3 1 3 H H 4-phenylphenyl -CH2C=»CCH2- H H 4-fluorophenyl -CHj-QfcCHCHj- H H 30 4-chlorophenyl -CH^CH^CHjCHj- n-C4H9 H H 4-phenoxyphenyl -CH2CH2CH2CHch3 ch3 CH3 ch3 35 3-trifluoromethylphenyl -CHCH=CHCHch3 ch3 -ch2ch—chch2- H ch3 2-methoxyphenyl H H Example 37 Preparation of (l,l'-Biphenyl-4-yl)dimethyl(lH-imidazol-l-ylmethyOsllane _ A mixture of 2.6 g (0.010 mol) of (1,l'-blphenyl 4-yl)chloromethyldimethylsilane and 1.1 g (0.012 mol) of imidazole sodium salt in 5 ml of dimethylformamide was warmed to 80-90° for 2 hours, cooled, diluted with water, and extracted with ether. The ether solution was washed with water and brine, dried over magnesium sulfate, and evaporated to leave 2.0 g of a viscous, pale yellow oil. Trituration of a small sample with hexanes gave a solid. The bulk of the crude product was then taken up in a hot mixture of 20 ml of hexanes and 3 ml of ethyl acetate, the solution was cooled slowly, and seed crystals were added when cloudiness was observed. The resulting crystals were collected and dried to give 0.84 g (29%) of the title compound as colorless flakes: m.p. 51-53°; ir (NujolR) 1235, 1215, 1105, 1065, 900, 830, 785, 750, 730, 685 cm-1; nmr (CDClj) 0.4 (6H, s), 3.7 (2H, s), 6.7 (IH, broad s), 7.0 (IH, broad s), 7.1-7.8 (10H, m); analysis for C18H20N2Si (mw 292-45>: Calculated C, 73.92; H, 6.89; N, 9.58; Found C, 73.4; H, 7.0; N, 9.4; 73.7; 7.0; 9.4.

Example 38 Preparation of (4-Chlorophenyl)dimethyl(lH-imidazol-l-ylmethyl)sllane·_ A mixture of 2.2 g (0.010 mol) of chloromethyl(45 chlorophenyDdimethylsilane and 1.1 g (0.012 mol) of imidazole sodium salt in 5 ml of dimethylformamide was stirred at 80-90° for 2 hours, cooled, diluted with water, and extracted with ether. The ether solution was washed with water and brine, dried over magnesium sulfate, and evaporated to leave 2.0 g (81%) of the 20 title compound as a yellow liquid: n£ 1.5472; ir (neat) 1560, 1495, 1480, 1375, 1250, 1105, 1080, 905, 830, 810, 740 cm-1; nmr (CDClj) 0.3 (6H, s), 3.6 (2H, s), 6.6 (IH, broad s), 6.9 (IH, broad s), 7.1 (IH, broad s), 7.3 (4H, s).

Example 39 Preparation of (2,4-Dichlorophenyl)dimethyl(lHimldazol-l-ylmethyl)silane_ A mixture of 5.1 g (0.020 mol) of chloromethyl(2,4-dichlorophenyl)dimethylsilane and 2.0 g (0.022 mol) of imidazole sodium salt in 10 ml of dry dimethylformamide was stirred at 80-90’ for 2 hours and worked up as in Example 18 to give 3.9 g (69%) of the 23 title compound as a brown oil: n& 1.5637; ir (neat) 1560, 1500, 1450, 1355, 1250, 1105, 1095, 1075, 1025, 840, 780, 735 cm-1; nmr (CDClj) 0.4 (6H, s), 3.9 (2H, s), 6.7 (IH, broad $), 7.0 (IH, broad s) 7.2-7.5 (4H, m).

Example 40 Preparation of Diphenyl(lH-imidazol-l-ylmethyl)methylsllane_ A mixture of 4.9 g (0.020 mol) of chloromethyl5 (diphenyl)methylsilane and 2.0 g (0.022 mol) of imidazole sodium salt in 10 ml of dry dimethylformamide was stirred at 80°C for 3.5 hours and worked up as in Example 18 to give 4.8 g of a yellow oil. Kugelrohr distillation at 125°/0.05 mm removed volatile impur10 ities, leaving behind 2.9 g (52%) of the title compound as an oil: njj2 1.5995; ir (neat) 3375, 3250, 1500, 1430, 1255, 1230, 1110, 1075, 1025, 810, 790, 735, 700, 660 cm1; nmr (CDClj) 0.6 (3H, s), 3.9 (2H, s), 6.6 (IH, broad s), 6.9 (IH, broad s), 7.2-7.5 (11H, m).

By applying the procedures of Example 37-40 to appropriate chloromethylsilanes, the compounds of Table XIV can be prepared.

S3378 Table XIV ,2 Rj-Si-OM J R, 4 ^2 ^3 % CHj CHj n22 1.4805 ^5 CH3 CHj n^2 1.4848 i-CjH, CHj CHj £-c4H9 CHj CHj n19 1.4811 «489 CHj CHj £C12H25 CHj CHj ng3 1.4585 2-c14H29 ch3 ch3 £C18H37 CHj CHj n^1 1.4639 cyclopropyl CHj CHj cyclobutyl ch3 ch3 cyclopentyl CHj CHj cyclohexylCH3 CHj n^2 1.4999 1-naphthyl CHj CHj r^3 1.6188 2-naphthyl CHj CHj phenyl CHj CHj bp 120-125' 4-bromophenyl CHj CHj n20 1.5741 4-fluorophenyl CHj CHj r^3 1.5314 4-methoxyphenyl CHj CHj n^5 1.5485 4-phenoxyphenyl CHj CHj n^2 1.5833 4-(4-chlorophenoxy)phenyl CHj CHj r^2 1.5564 4-(4-fluorophenoxy)phenyl CHj CHj 4-(4-trifluoromethylphenoxy)phenyl CHj % 4-(4-methylphenoxy)phenyl CHj ch3 Table XIV (continued). 4 4-thiomethylphenyl °S CHj n^3 1.5855 4-methylsulfonylphenyl ch3 CHj 21 1.5552 4-trifluoromethylphenyl CHj ch3 flp2 1.4867 4-methylphenyl cn3 CHj n21 1.5482 4-i-propylphenyl CHj CHj 4-t-butylphenyl CHj CHj n23 1.5229 4-cyclohexylphenyl ch3 ch3 ηξ2 1.5085 4-trifluoromethoxyphenyl CHj ch3 ιγ2 1.4888 4-(4-chlorophenyl)phenyl CHj CHj 4-(4-methylphenyl)phenyl CHj CHj 4-(4-trifluoromethylphenyl)phenyl CHj CHj 4-(4-fluorophenyl)phenyl CHj CHj 4-(4-bromophenyl)pheny1 ch3 CHj n22 1.5745 3-phenylphenyl CHj CHj n^1 1.6002 3-trifluoromethylphenyl CHj ^3 n20 1.4927 3-chlorophenyl CHj CHj η£2 1.5560 2-trifluoromethylphenyl CHj CHj n23 1.5056 2-phenylphenyl ch3 CHj n£2 1.5996 2-chlorophenyl CHj CHj 22 r£z 1.5382 2-methoxyphenyl CHj CHj Hq2 1.5344 2,3-dimethylphenyl CHj CHj 2,3-dimethoxyphenyl CHj CHj n^2 1.5350 2,4-difluoropheny1 CHj CHj 2-fluoro-4-chlorophenyl CHj CHj 2-chloro-4-fluorophenyl CHj CHj 2-chloro-4-phenylphenyl CHj CHj 2-fluoro-4-phenylphenyl CHj CHj 2-methy1-5-chlorophenyl CHj Table XIV (continued) 2,6-dimethoxypheny1 CHj ch3 n23 1.5348 2,6-dimethylpheny1 CHj CHj 3,4-dichlorophenyl CHj CHj n23 1.5673 3-methy1-4-fluorophenyl CHj CHj 3,5-dichlorophenyl CHj CHj n22 1.5461C2H5C285 CHj iC3H7 cyclohexyl CHj 2-C4H9 CH3 n^2 1.4710 B-Cl()821 cyclopropyl CHj 2^12^5 n-CjH? ch3 2-ci4H29 i-OjHy CHj •2tC18H37 3-methyIbutyl CH3 cyclopropyl £-C^13 CHj cyclopentyl cylopentyl CHj cyclohexyl cyclohexyl ch3 1-naphthyl •^^489 CHj 1-naphthyl t-CAH9 CHj 2-naphthyl n-CsHll ch3 phenyl n-CjH? ch3 phenyl 2-O4H9 ch3 ηβ 1.5449 phenyl 1,1-dimethylpropyl CHj phenyl •2C^13 CHj 4-phenylphenylC2h5 ch. 22 4-phenylphenyl 2-04^ CH3 rtf 1.5880 4-bromophenyl i-CjH? CHj 4-chlorophenyl 2-C4H9 CHj rtf 1.5415 4-fluorophenyl 2-C4H9 CH3 rtf 1.5161 4-phenoxyphenyl ί-04Η9 CHj 4-i-propylphenyl cyclopropyl 4-t-butylphenyl CHj Table XIV (continued) 3-phenylphenyl i-C4H9 CHj 3-trifluoromethylphenyl StC4H9 CHj 3-chlorophenyl 2-%ffl3 2-methoxyphenyl t-c4H9 2-thiomethylphenyl cyclobutyl ch3 2-phenylphenyl i-C4H9 ch3 ΟΊ 2,4-dichlorophenyl IfC4H9 ch3 rtf 1.5588 2,4-dichlorophenyl cyclopropyl ch. 2,3-dimethylphenyl rv-C^ CMj 2-methyl-5-fluorophenyl cyclopentyl CH, 2,5-dimethoxyphenyl 4-methylpentyl CH, 2,6-dimethylphenyl 1-methylbutyl CHj 3,4-dichlorophenyl 3,5-dichloropheny1 2-C4H9 CH3 3,5-dichlorophenyl cyclohexyl% 3-methy1-4-chlorophenyl cyclopropyl CHj 4-fluorophenyl phenyl 3 ηθ9 1.5810 4-chlorophenyl phenyl CHj n^1 1.6000 4-bromophenyl phenyl CHj n22 1.6115 4-phenylphenyl phenyl CHj n21 1.6378 4-t-butylphenyl phenyl CHj 4-thiomethylphenyl phenyl ch3 4-phenoxyphenyl phenyl ch3 4-trifluoromethoxyphenyl phenyl CHj 4-methylsulfonylphenyl phenyl % 4-cyclohexylphenyl phenyl ch3 4-(4-fluorophenyl)phenyl phenyl % 3-trifluoromethylphenyl phenyl CH, 2-chlorophenyl phenyl CHj r£2 1.6058 2-methoxyphenyl phenyl CHj Table XIV (continued) 2,4-dichlorophenyl phenyl 2-chloro-4-phenylphenyl phenyl 2-fluoro-4-phenylphenyl phenyl _2 CH, CHj CH, n22 1.6150 3,5-dichlorophenyl phenyl CHj 2,5-dimethoxyphenyl phenyl CHj 2,6-dimethoxyphenyl phenyl % 4-fluorophenyl 4-fluorophenyl CHj n22 1.5569 4-chlorophenyl 4-chlorophenyl CHj rip 1.5820 4-bromophenyl 4-bromophenyl CHj n^1 1.6305 4-phenylphenyl 4-phenylphenyl CHj m.p. 44-53° 4-methoxyphenyl 4-methoxyphenyl CHj n21 1.5947 3-trifluoromethylphenyl 3-trifluoromethylphenyl CHj 2-chlorophenyl 2-methoxyphenyl 2.4- dichlorophenyl 3.5- dichlorophenyl 2-chlorophenyl 2-methoxyphenyl 2.4- dichlorophenyl 3.5- dichlorophenyl CHj n20 1.5999 CHj CHj n22 1.6019 CHj 2-chlorophenyl 4-chlorophenyl CHj n20 1.6044 2-chlorophenyl 4-fluorophenyl CHj 4-phenylphenyl 4-chlorophenyl CHj 4-phenylphenyl 4-fluorophenyl CHj 4-phenylphenyl 2,4-dichlorophenyl CHj 4-fluorophenyl 2,4-dichlorophenyl CHj 4-chlorophenyl 2,4-dichlorophenyl CHj 1-naphthyl 2,6-dimethoxypheny1 CHj 4-phenoxyphenyl 3,4-dichloropheny1 ch3 ^5 ^5C2H5 i-C3H7 i-CjH? i-CjH, 2?C4H9 n-C^Hj n-C4H9 £-C8H17 ^5 cyclopentyl —-C14H29 cyclopropyl 1-methylbutyl 3 378 Table XIV (continued) 1 ^2 n-C^y n-C6Hi3 £-c6h13 cyclopropylC2H5 *-c4h9 cyclohexyl η-Ο,Η? n-CjH? 1-naphthyl ITC4H9 2-naphthyl DrcaH9 cyclobutyl phenyl cyclopropyl S“C6H13 4-phenylphenyl C^5C2»5 4-phenylphenyl •^G4R9 4-phenylphenyl H-C<*13 4-phenylphenyl cyclohexyl cyclohexyl 4-chlorophenyl £-C4H9 4-fluorophenyl rv-CjH? 4-phenoxyphenyl n-C4H9 cyclohexyl 4-(4-chlorophenoxy)phenyl DtC4H9 2-C4H9 4-t-butylphenyl stC4h9 iC4H9 3-methoxyphenyl ^5 t-C4H9 3-trifluoromethylphenyl &-C4H9 s^Hj, 2-thiomethylphenyl 3-methylbutyl 2-phenylphenyl cyclohexyl cyclohexyl 2,4-dichlorophenyl D-C4H9 2-C4H9 2,6-dimethylphenyl t-C4H9 3,5-dichlorophenyl cyclopentyl cyclopentyl 3-methyl-4-chlorophenyl s-C^H? 2-methyl-5-fluorophenyl n-c4»9 iW % phenyl phenyl cyclohexyl phenyl phenyl ΰ^18Η37 phenyl phenyl £-^4^9 4-chlorophenyl 4-chlorophenyl -C12H25 4-chlorophenyl 4-chlorophenyl 1-naphthyl 4-fluorophenyl 4-fluorophenyl cyclopropyl phenyl 4-t-butylphenyl —“G4R9 phenyl 4-phenylphenyl Table XIV (continued) R! ^2 ^3 t-C4H9 phenyl 2,4-dichlorophenyl η-Ο,Η, phenyl 3-trifluoromethylphenyl i-C4H9 phenyl 3,5-dichlorophenyl cyclopentyl phenyl 2,6-dimethoxyphenyl B-C14H29 4-chlorophenyl 2-fluorophenyl 4-fluorophenyl 4-phenylphenyl phenyl phenyl phenyl m.p. 175-178° 4-chlorophenyl 4-chlorophenyl 4-chlorophenyl 4-fluorophenyl 4-fluorophenyl 4-fluorophenyl 4-phenylphenyl 4-phenylphenyl 4-phenylphenyl 2,4-dichlorophenyl 2,4-dichlorophenyl 2,4-dichlorophenyl phenyl 4-fluorophenyl 4-fluorophenyl phenyl 4-chlorophenyl 4-chlorophenyl phenyl 4-phenylphenyl 4-phenylphenyl phenyl 2,4-dichlorophenyl 2,4-dichlorophenyl 2-naphthyl 4-methylthiophenyl 4-methylthiophenyl 4-chlorophenyl 2-methoxyphenyl 2-methoxyphenyl 4-chlorophenyl 3-chlorophenyl 3-chlorophenyl phenyl 2-chlorophenyl 4-fluorophenyl phenyl 4-chlorophenyl 4-phenylphenyl 1-naphthyl 4-bromophenyl 3-methylphenyl 4-phenoxyphenyl 3,5-dimethylphenyl 3,4-dichlorophenyl INSERT F Example 41 Preparation of {l,l'-Biphenyl-4-yl)dimethyl(2-methyllH-lmidazol-l-ylmethyl)silane_ The title compound is prepared by applying the 5 procedure of Example 37 to (l,l'-biphenyl-4-yl)chloromethyldimethylsilane and the sodium salt of 2-methylimidazole.

Related compounds may be made in this way using salts of 2,4-dimethylimidazole, 4,5-dimethylimidazole, and 2,4,5-trimethylimidazole.

The procedure of Example 41 may be used to prepare the compounds of Table XV.

Table XV S 1 23C2H5 CHj CHj CHj CHj CHj 1^18^7 CHj % H CHj CHj cyclohexyl CHj CHj H CHj CHj 1-naphthyl CHj CHj CHj Η H 15 phenyl CHj CHj H CHj H phenyl CHj CHj H Η CHj 4-phenylphenyl CHj CHj CH3 H H 4-(4-fluorophenyl)phenyl CHj CHj CHj H H 4-phenoxyphenyl CHj CHj CHj CHj CHj 20 3-trifluoromethylphenyl CHj CHj H CHj CHj 2-methoxyphenyl CH3 CHj CHj H H 2,4-dichlorophenyl CHj CHj CHj CHj CHj 2-chloro-4-phenylphenyl CHj CHj H CHj CHj phenyl 2-C4H9 CHj CHj H Η 25 4-phenylphenyl n-C4H9 CHj H CHj CHj 2,4-dichlorophenyl 12-^13 CHj CHj H Η 4-(4-chlorophenoxy)phenyl cyclohexyl CHj CH3 H Η phenyl phenyl CHj CHj CHj CHj 4-fluorophenyl phenyl CHj CHj H Η 30 4-fluorophenyl phenyl CHj CHj CHj CHj 4-chlorophenyl phenyl CHj H CHj ch3 4-fluorophenyl 4-fluorophenyl CHj CH3 H Η 4-fluorophenyl 4-fluorophenyl CHj H CHj CHj 4-chlorophenyl 4-chlorophenyl CHj CHj CHj CHj 35 4-chlorophenyl 4-chlorophenyl CHj CHj H Η Table XY (continued) !ΐ Qj 02 2-chlorophenyl 4-chlorophenyl CHj CHj CHj CHj 2,4-dichlorophenyl 2,4-dichlorophenyl *3 CHj Η H £·°18η37 £C^13 H ch3 CHj 1-naphthyl £-C4H9 £-C4H9 CH ch3 CHj phenyl phenyl phenyl CHj H H phenyl phenyl phenyl ch3 H CHj phenyl phenyl phenyl CHj CHj H 3 3 7 8 Example 42 Preparation of the 1:1 complex of (1,1’-Biphenyl-4-yl) dimethyl(lH-imidazol-l-ylmethyl)silane and Cuprous Chloride_ A mixture of 0.50 g (0.0017 mol) of (l,l'-biphenyl-4-yl)dimethyl(lH-imidazol-l-ylmethyDsilane and 0.22 g (0.0017 mol) of cuprous chloride in 15 ml of tetrahydrofuran was refluxed under N2 for 15 minutes, and the resulting deep green solution was evaporated to leave the title complex as a dark green solid: m.p. 72-80° (decomp.),· ir (NujolR) 1590, 1515, 1250, 1110, 840, 820, 750, 695, 650 cm-1.

By applying the procedure of Example 24, any of the compounds of Tables XIV, XV, XVI, XVII, XVIII or XIX can be converted to metal complexes or salts.

Example 43 Preparation of (l,l-'Biphenyl-4-yl)(lH-imidazoi1-ylmethy1)(methoxy)methylsilane_ A mixture of (l,l'-biphenyl-4-yl)chloro(ehloromethyUmethylsilane and two equivalents of imidazole sodium salt in dimethylformamide is warmed to 80-90’C for 2 hours. Ten equivalents of methanol is then added, and the mixture is held at 70° for 1 hour, cooled, diluted with water, and quickly extracted with ether. Washing the ether solution with water and brine, drying over magnesium sulfate, and evaporation leaves the title compound.

Related compounds can be made in the same way, using the appropriate chlorosilane and alcohol; for Rg = OH, water is used instead of an alcohol, and hydrolysis is conducted at 20-25° instead of 70°.

Example 44 Preparation of l,l-(Oimethylethoxy)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane__ A mixture of 3.6 g (0.015 mol) of chloromethyl5 (l,l-dimethylethoxy)methyl(phenyl)silane and 1.3 g (0.015 mol) of imidazole sodium salt in 10 ml of dimethylformamide was stirred at 50° for 3 hours, allowed to stand at room temperature for 72 hours, poured into water, and extracted with ether. The ether extracts were washed three times with water and once with brine, dried over magnesium sulfate, and evaporated to leave 3.8 g of an oil. Impurities were removed by Kugelrohr distillation at 90° (airbath)/ 0.05 mm to leave 2.9 g (71%) of the title compound as a pale yellow oil: n20 1.5291; ir (neat) 3105, 3070, 3045, 2970, 1590, 1500, 1425, 1360, 1250, 1235, 1185, 1110, 1055, 1020, 900, 805, 740, 700, 660 cm’1; nmr (CDClj): 0.6 (3H, s), 1.3 (9H, s), 3.6 (2H, s), 6.8 (IH, s), 7.0 (IH, s) and 7.3-7.7 (6H, m).

INSERT P The compounds of Tables XVI and XVII can be made using the procedures of Examples 43 and 44.

Table XVI 4 «2C2*5 (M3 CHj t-C4H9 CHj 1*4*9 2-C4H9 CHjC2*5 £C12H25C2*5 CHj £*18*37 ch. cyclopropyl CHj stC4h9 cyclohexyl CHj CHj 1-naphthyl —”^3*7 i-CjHy 2-naphthyl cyclobutyl 2C3H7 phenyl CHj Η phenyl CHj CHj phenyl CHjC2*5 phenyl CHj A-^7 phenyl ^.“^485 H 4-phenylphenyl 2*4*9 CHj 4-phenylphenyl t-C^ H 4-phenylphenyl CHj c2h5 4-phenylphenyl CHj 2-C4H9 4-chlorophenyl 2*^489 2-C4H9 4-chlorophenyl CHj CHj 4-chlorophenyl CHjC2*5 4-fluorophenyl 2tc^I3 n-CjH? 4-fluorophenyl CHj 4-phenoxyphenyl cyclohexyl 1*4*9 4-t-butylphenyl £*3*7 · s-C4H9 3-trifluoromethylphenyl t-C4H9 H 2-methylthiophenyl cyclopentylC2*5 .5352 Table XVI (continued) ^6 ' 2,4-dichlorophenyl CHj CHj 2,4-dichlorophenyl CHjC2H5 2,4-dichlorophenyl CHj i-c4H9 2,4-dichlorophenyl 2-CaH9C2»5 2,3-dimethylphenyl cyclopropyl i-C3^7 2-methyl-5-fluorophenyl tt-CjHy 2,6-dimethoxyphenyl 1,1-dimethylpropyl H 3-methy1-4-chlorophenylC2H5 CHj 3,5-dichlorophenyl 2-c5H11 c2h5 ^C12H25 2,4-dichlorophenyl 1-C4H9 £C1BH37 phenyl CHj 1-naphthyl phenyl ^5 phenyl phenyl 4-fluorophenyl phenyl CHj 4-chlorophenyl phenyl 2’C3H7 4-phenylphenyl phenyl C^5 4-phenylphenyl phenyl s-c4h9 4-t-butylphenyl phenyl ^C4H9 3-fluorophenyl phenyl ^5 2-methoxyphenyl phenyl H 2-chlorophenyl phenyl CHj 2,4-dichlorophenyl phenyl i-CjH7 3,5-dichlorophenyl phenyl nrCjH? 4-fluorophenyl 4-fluorophenyl t-C4H9 4-fluorophenyl 4-fluorophenyl 4-chlorophenyl 4-chlorophenyl CHj 4-chlorophenyl 4-chlorophenylC2*5 4-phenylphenyl 4-phenylphenyl CHj 2,4-dichlorophenyl 2,4-dichlorophenyl ^5 3-trifluoromethylphenyl 3-tri fluoromethylpheny1 iC4H9 2-methoxyphenyl 2-methoxyphenyl H 2-chlorophenyl 4-fluorophenyl H Table XVI (continued) *2 3-trifluoromethylphenyl 4-t-butylphenyl £-C4H9 2-fluoro-4-chlorophenyl 4-bromophenyl i-C3H7 2,3-dimethylphenyl 4-methylthiophenylC^5 2,6-dimethoxyphenyl 4-methoxyphenyl H 3,4-dichlorophenyl 4-methylphenyl i-C4H9 INSERT G Table XVII R2 RJ-Si-CHjN OR, Q, 4 R^ % Qg C^5 CHj CHj CHj CHj CH, cyclohexyl CHj i-CjH7 H CHj % £-c18H37 t-C4H9 CHj H H 1-naphthyl CHj i-CjH? CHj H H phenyl CHj £“C4H9 Η ch3 H phenyl CHj «Λ Η Η CHj phenyl CHj t-C4H9 CHj CHj CHj phenyl CHj I-C4H9 H CHj *3 phenyl CHj CHj H H 4-phenylphenyl r>-C4H9 £-^4^9 CHj CHj CHj 4-phenylphenyl CHj £.-c4h9 CHj H H 4-phenylphenyl CHj £‘C4H9 ch3 CHj CHj 4-chlorophenyl CHj t-C4H9 CHj H H 4-chlorophenyl CHj t-c4H9 Η CH CH, 4-fluorophenyl CHj £-6469 H H 4-fluorophenyl CHj £-*-4% H H CH, phenyl phenyl ^5 CHj CHj CH phenyl phenyl nrC3H7 CHj CHj CH 4-fluorophenyl phenyl H CHj CHj 4-fluorophenyl phenyl £-6489 CHj H H 4-chlorophenyl phenyl i“C3^7 CHj H H 2,4-dichlorophenyl phenyl Η CH, H H 4-fluorophenyl 4-fluorophenyl —~C4R9 % H H 4-fluorophenyl 4-fluorophenyl £-c4h9 HCH3CH3 4-fluorophenyl 4-fluorophenyl '£6489 CH CHj chJ 2-methoxyphenyl 2-methoxyphenyl ^5 CH H H 3-methylphenyl 3-methylphenyl £-C4H9 CH, H H 100 Example 45 Preparation of (lH-Imidazol-l-ylmethyl)phenylbis(2propoxy)sllane The title compound can be made by applying the 5 procedure of Example 26 to chloromethyl(phenyl)bis(2-propoxy)silane: n^2 1.4971; nmr (CDClj) 1.2 (12H, d, 3 = 6), 3.6 (2H, s), 4.2 (2H, septet, 0 = 6), 6.8-7.6 (8H, m).

The compounds of Tables XVIII and XIX can be made similarly. 101 Table XVIII OR RJ-51' ·*· 1 OR mJ 6 A/ 2RiR6 q2 Qj c2h5 t-C4H9 H H H n-C4H9C2H5 H H H £~C18H37 CHj H H H cyclohexyl n-CjH7 H H H 1-naphthyl i-C4H9 H H H phenyl CHj CHj CHj CH, phenyl n-CjH? ch3 H H phenyl i“C3H7 H CHj CH, phenyl t-C4H9 H H H 4-phenylphenylC2H5 H H H 4-phenylphenyl £“£489 CHj CHj CH- 4-fluorophenyl CHj CHj H H 4-fluorophenylC2H5 H H H 4-chlorophenyl c2h5 H H H 4-chlorophenyl i-C3H7 H H H 3-trifluoromethylphenyl £“C4H9 CHj CHj CH 2-methoxyphenyl n-CjHy CHj H H 2,3-dimethylpheny1 ^”^489 H H H 2,4-dichlorophenyl CHj H H H 2,4-dichlorophenyl c2h5 H H H 2-methoxy-5-fluorophenyl i-C3H7 H H H 2,6-dimethoxyphenyl CHj H H H 3,4-dichlorophenylC2H5 H H H 3,5-dichlorophenyl £“C4H9 H H H 3 3 7 8 102 Table XIX 4 «1 f2 0Λ -CHjCHj- H H H £-C4H9 -CH2CH- CH3 H H ^C18H37 -CH2CH2CH2- ?2H5 H ch3 ch3 cyelohexyl -ch2ch- CH3 ch3 CHj 1-naphthyl -ch2ch2- CHj H Η phenyl -ch2ch2- ?2H5 H H Η phenyl -CHjCH- n-C3H7 H H Η phenyl -ch2ch- H H Η phenyl -C(CH3)2C(CH3)2- h H Η 4-phenylphenyl -CH2CH2- ?2H5 H H Η 4-phenylphenyl -CH^CH- ^3^3 H H Η 4-phenylphenyl —CH—CH— H H Η 4-fluorophenyl ch3 -CHjCH- ?2H5 H H Η 4-fluorophenyl H H Η 4-chlorophenyl -ch2ch- H H Η 4-chlorophenyl -C(CH3)2C(CH3)2- h CH, | H Η 3-trifluoromethylphenyl -CHCHjCCCHjJj- ch3 CHj CHj 3 3 7 8 103 Table XIX (continued) 0, 2-methoxyphenyl -CHjCH- CH, H H 2,3-dimethylphenyl H ch3 CH, 2,4-dichlorophenyl ?2H5 -CH^H- H H H 2,4-dichlorophenyl n-C3H7 -CHjCH- H H H 2-methoxy-5-fluorophenyl CH, CH, -chc(ch,)2ch- CH, H H 2,6-dimethoxyphenyl -ch2ch2- H H H 3,4-dichlorophenyl CH, CH, -CHCHjCH- CH, CH, CH, 3,5-dichlorophenyl CH, CH, 1 3 I -5 -CH—CH- ch3 CH3 CH, ^5 -CHjCHxCHCH^ H CH,CH3 CH, CH, ι ’ ι 3 -CHCHgCHjCH- H ch3 CH, phenyl -CHgCHsCHCHj- H H H phenyl -c(ch,)2ch=chc(ch,)2- H H H phenyl CH, CH, -CHC^CHgCH- H H H phenyl -c(ch,)2ch2ch2c(ch,)2- H H H 4-phenylphenyl -ch2ch=chch2- H H H 4-phenylphenyl CH, CH, I j I j -CH2C=CCH2- H H H 4-fluorophenyl -CH2-CH=CHCH2- H H H 4-chlorophenyl -CH2CH2CH2CH2- H H H 4-phenoxyphenyl -CH2CH2CH2CH- CH, H H 3-trifluoromethylphenyl CH, CH, -CHCH=CHCH- H CHj CH, 2-methoxyphenyl . CH, CH, -ch2ch—chch2- CH, CH, CH, 104 Formulations Useful formulations of the compounds within the scope of this invention can be prepared in conventional ways. They include dusts, granules, pellets, solutions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended In suitable media and used at spray volumes of from a few pints to several hundred gallons per acre. High strength compositions are primarily used as intermediates for further formulations. The formulations, broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of a) about 0.1% to 20% surfactant(s) and b) about 5% to 99% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: Percent by Weight Active Ingredient Dlluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, Emulsions, Solutions, (including Emulsifiable Concentrates) 5-50 40-95 0-15 Aqueous Suspensions 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 1-95 5-99 0-15 High Strength 90-99 0-10 0-2 Compositions Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing. 105 Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. The more absorptive diluents are preferred for the wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. McCutcheon’s Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, Agglomeration, Chemical Engineering, December 4, 1967, pp. 147ff. and Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp. 8-59ff. 106 Example 46 Wettable Powder (1,l-Biphenyl-4-yl)dimethy1(1H-1,2,4-triazol-l-y1methyDsilane 40% dioctyl sodium sulfosuccinate 1.5% sodium ligninsulfonate 3% low viscosity methyl cellulose 1.5% attapulgite 54% The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

All compounds of the invention may be formulated in the same manner.

Example 47 Wettable Powder (4-Bromophenyl)dimethyl(lH-l,2,4-triazol-l-ylmethyl)silane 20% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 76% The ingredients are blended, coarsely hammermilled and then air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.

Example 48 High Strength Concentrate (4-Chlorophenyl)dimethyl(lH-l,2,4-triazol-l-y1methyDsllane 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0% The ingredients are blended and ground in a hammer-mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways. 107 Example 49 Dust high strength concentrate from ' Example 48 25.456 pyrophyllite, powdered 74.6% The ingredients are thoroughly blended and packaged for use.

Example 50 Aqueous Suspension (1,1’-Biphenyl-4-yl)dimethyΗ1H-1,2,4-triazol-l-y1methyl)silane 50.0% polyacrylic acid thickener 0.3% dodecylphenyl polyethylene glycol ether 0.5% disodium phosphate 1.0% monosodium phosphate 0.5% polyvinyl alcohol 1.0% pentachlorophenyl 0.4% water 46.3% The ingredients are ground together in a sand mill to produce particles substantially all under five microns in size.

Example 51 Emulsifiable Concentrate Dimethyl(phenyl)(lH-l,2,4-triazol-l-ylmethyl)silane 20% chlorobenzene 74% sorbitan monostearate and polyoxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. 108 Example 52 Emulsifiable Concentrate Dimethyl(4-methylpheny1)(1H-1,2,4-triazol-l-ylmethyl) silane 30% blend of oil soluble sulfonates and polyoxyethylene ethers 4% xylene 66% The ingredients are combined and stirred with gentle warming to speed solution. A fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product.

Example 53 Granule wettable powder of example 46 15% gypsum 69% potassium sulfate 16% The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 mm. (U.S.S. # 18 to 40 sieves), the granules are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain active ingredient.

Example 54 Emulsifiable Concentrate (2,4-Dichlorophenyl)dimethy1(1H-1,2,4-triazol-l-ylmethyDsilane 30% blend of oil soluble sulfonates and polyoxyethylene ethers 4% xylene 66% The ingredients are combined and stirred with gentle warming to speed solution. A fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product. 109 Example 55 Emulsifiable Concentrate Butyl(4-chlorophenyl)methy1(1H-1,2,4-triazol-l-y1methyDsilane 30% blend of oil soluble sulfonates and polyoxyethylene ethers 4% xylene 66% The ingredients are combined and stirred with gentle warming to speed solution. A fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product.

Example 56 Emulsifiable Concentrate bis(4-Chlorophenyl)methyl(lH-l,2,4-triazol-l-ylmethy1)silane 30% blend of oil soluble sulfonates and dolyoxyethylene ethers 4% xylene 66% The ingredients are combined and stirred with gentle warming to speed solution. A fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product.

Example 57 Emulsifiable Concentrate bis(4-FluorophenyDmethy1(1H-1,2,4-triazol-l-ylmethyl)silane 20% chlorobenzene 74% sorbitan monostearate and polyoxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. 110 Example 56 Emulsifiable Concentrate 4-Fluoropheny1(methy1)pheny1(1H-1,2,4-triazol-l-y1methyl)silane 30% blend of oil soluble sulfonates and polyoxyethylene ethers 4% xylene 66% The ingredients are combined and stirred with gentle warming to speed solution. A fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product.

Example 59 Wettable Powder (1,l'-Bipheny1-4-yl)dimethy1(lH-imidazol-l-ylmethyl )silane 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely hammermilled and then air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.

Example 60 Wettable Powder (1,1-Bipheny1-4-yl)dimethy1(ΙΗ-imidazol-l-ylmethy1) silane 40% dioctyl sodium sulfosuccinate 1.5% sodium ligninsulfonate 3% low viscosity methyl cellulose 1.5% attapulgite 54% The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

All compounds of the invention may be formulated in the same manner. 111 Example 61 Emulsifiable Concentrate (1,l'-Blphenyl-4-yl)dimethyl(lH-imidazol-l-ylmethyl)silane 30% blend of oil soluble sulfonates and polyoxyethylene ethers 4% xylene 66% The ingredients are combined and stirred with gentle warming to speed solution. A fine screen 10 filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product.

Example 62 Emulsifiable Concentrate (1,l'-Biphenyl-4-yl)dimethyl(lH-imidazol-l-ylmethyl)- silane 20% chlorobenzene sorbitan monostearate and poly- 74% oxyethylene condensates thereof 6% 20 The ingredients are combined and stirred to produce a solution which can be emulsified for application. Example 63 Aqueous Suspension in water 25 (1,1'-Bipheny1-4-yl)dimethy1(ΙΗ-imidazol-l-ylmethyl)- silane 25% hydrated attapulgite 3% crude calcium ligninsulfonate 10% sodium dihydrogen phosphate 0.5% 30 water 61.5% The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns. 112 Example 64 High Strength Concentrate (ljl'-Siphenyl-A-yDdimethyKlH-imidazol-l-ylmethyl)silane 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0% The ingredients are blended and ground in a hammer-mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways.

Example 65 Granule wettable powder of example 60 15% gypsum 69% potassium sulfate 16% The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 mm. (U.S.S. # 18 to 40 sieves), the granules are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain active ingredient.

Example 66 Dust high strength concentrate from Example 64 25.4% pyrophyllite, powdered 74.6% The ingredients are thoroughly blended and packaged for use. 113 Example 67 Emulsifiable Concentrate 4-Chlorophenyl(methyl)phenyl(lH-imidazol-l-ylmethyl)silane 20% chlorobenzene 74% sorbitan monostearate and polyoxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. 114 Utility The compounds of this invention are useful as plant disease control agents. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal and fruit crops, such as, Puccinia recondita, Erysiphe clchoracearum, Erysiphe graminis, Venturia inaequalls, Heltninthosporium maydis. Cercospora arachidicola, Uroinyces phaseoll and Monllinla fructlcola, Rhizoctonla solani, Pyrlcularla oryzae, Phytophthora infestans and other Phytophthora species. They also control seed pathogens such as Pythlum aphanadermatum.

Disease control is ordinarily accomplished by applying an effective amount of the compound either pre- or post-infection to the portion of the plant to be protected, such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing. The compound may also be applied to the seed from which the plants to be protected are to be grown.

Rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions. Foliage can normally be protected when treated at a rate of from less than 1 to 500 ppm of active ingredient. Plants growing in soil treated at a concentration from 0.1 to about 20 kg/ha can be protected from disease. Seed and seedlings can normally be protected when seed is treated at a rate of from 0.06 to about 3 grams per kilogram of seed. 115 The compounds of this invention can be mixed with fungicides, bactericides, acaricides, nematicides, insecticides, or other biologically active compounds in order to achieve desired results with a minimum expenditure of time, effort and material. Amounts of these biologically active materials added for each part by weight of the composition of this invention may vary from 0.05 to 25 parts by weight. Suitable agents of this type ere well-known to those skilled in the art. Some are listed below: Fungicides: methyl 2-benzimidazolecarbamate (carbendazim) tetramethylthiuram disulfide (thluram) n-dodecylguanidine acetate (dodine) manganese ethyleneblsdithiocarbamate (maneb) 1,4-dichloro-2,5-dimethoxybenzene (chloroneb) methyl l-(butylcarbamoyl)-2-benzimidazolecarbamate (benomyl) 2-cyano-N-ethylcarbamoyl-2-methoxyiminoacetamide (cymoxanil) N-trichloromethylthiotetrahydrophthalimide (captan) N-trichloromethylthiophthalimide (folpet) dimethyl 4,4’-(o-phenylene)bis(3-thioallophanate) tthiophanate-methyl) 2-(thiazol-4-yl)benzimidazole (thiabendazole) aluminum tris(O-ethyl phosphonate) (Aliette) tetrachloroisophthalonitrile (chlorothalonil) 2,6-dichloro-4-nitroaniline (dichioran) N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine methyl ester (metalaxyl) cis-N-[(l,l,2,2-tetrachloroethyl)thio]cyclohex-4-ene1,2-dicarboximide (captafol) 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,A-dioxo-1imidazolidine carboxamide (iprodione) 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione (vinclozolin) 116 kasugamycin 0-ethyl-S,S-diphenylphosphorodithioate (edifenphos) Bactericides; tribasic copper sulfate streptomycin sulfate oxytetracycline Acaricides: senecioic acid, ester with 2-sec-butyl-4,6-dinitrophenol (binapacryl) 6-methyl-l,3-dithiolo[2,3-B]quinonolin-2-one (oxythioquinox) 2,2,2-trichloro-l,l-bis(4-chlorophenyl)ethanol (dicofol) bis(pentachloro-2,4-cyclopentadien-l-yl) (dienochlor) tricyclohexyltln hydroxide (cyhexatin) hexakis(2-methyl-2-phenylpropyl)distannoxane (fenbutin oxide) Nematicides: 2- [diethoxyphosphinylimino]-l,3-dithletane (fosthietan) 20 S-methy1-1-(dimethylcarbamoyl)-N-(methylcarbamoyloxy)thioformimidate (oxamyl) S-methy1-1-carbamoyl-N-(methylcarbamoyloxy)thioformimidate N-isopropylphosphoramidic acid, 0-ethyl-0'-[4-(methyl25 thio)-m-tolyl]diester (fenamiphos) Insecticides: 3- hydroxy-N-methylcrotonamide(dimethylphosphate)ester (mcnocrotophos) methylcarbamic acid, ester with 2,3-dihydro-2,2-di30 methyl-7-benzofuranol (carbofuran) 0-[2,4,5-trichloro-a-(chloromethyl)benzyl]phosphoric acid, 0',Ο'-dimethyl ester (tetrachlorvinphos) 2-mercaptosuccinic acid, diethyl ester, S-ester with thionophosphoric acid, dimethyl ester (malathion) phosphorothioic acid, 0,0-dimethyl, O-ja-nitrophenyl ester (methyl parathion) 3 378 117 methylcarbamlc acid, ester with o-naphthol (carbaryl) methyl N-t[(methylBmino)carbonyl]oxy)ethanimidothioate (methomyl) N*-(4-chloro-o-tolyl)-N,N-dimethylformamidine 5 (chlordimeform) 0,0-diethy1-0-(2-isopropyl-ft-methyl-6-pyrimldyDphosphorothioate (diazinon) octachlorocamphene (toxaphene) O-ethyl 0-£-nitrophenyl phenylphosphonothioate (EPN) cyano(3-phenoxyphenyl)-methyl 4-chloro-a-(l-methylethyl)benzeneacetate (fenvalerate) (3-phenoxyphenyl)methyl (♦)-cis,trans-3-(2,2-dlchloroethenyl)-2,2-dimethylcyclopropanecarboxylate (permethrin) dimethyl N,N'-[thiobis](N-methylimino)carbonyloxy]]bistethanlmidothioate] (thlodicarb) phosphorothiolothionic acid, 0-ethyl-0-[4-(methylthio)phenyl]-S-n-propyl ester (sulprofos) a-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,220 dimethylcyclopropane carboxylate (cypermethrin) cyano(3-phenoxyphenyl)methyl 4-(difluoromethoxy)-a(methylethyl)benzeneacetate (Payoff) 0,0-diethy1-0-(3,5,6-trichloro-2-pyridyl)phosphorothioate (chlorpyrifos) 0,0-dimethyl-S-[(4-oxo-l,2,3-benzotriazin-3-(4H)-yl)methyl]phosphorodithioate (azinphos-methyl) ,6-dimethyl-2-dimethylamino-4-pyrimidinyl dimethyl carbamate (Pirimoi) S-(N-formyl-N-methylcarbamoylmethyl)-0,O-dimethyl 30 phosphorodithioate (formothion) S-2-(ethylthioethyl)-0,0-dimethyl phosphorothioate (demeton-S-methyl) a-cyano-3-phenoxybenzyl cis-3-(2,2-dibromovinyl)-2,2dimethylcyclopropane carboxylate (deltamethrin) cyano(3-pbenoxyphenyl)methyl ester of N-(2-chloro-4trifluoromethylphenyl)alanine (Mavrik) 118 This invention is further illustrated by the following examples.

Example 68 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). These suspensions were sprayed to the point of run-off on wheat seedlings. The following day, the plants were inoculated with a spore suspension of Puccinia recondita var. trltlcl, causal agent of wheat leaf rust, and incubated in a saturated humidity chamber at 20° for 24 hours and then in a growth room for an additional 7 days, when disease ratings were made. Percent disease control is shown in the following table. Treated plants had few or no rust pustules while the untreated plants had numerous rust pustules on each leaf.

Table 1 Compound % Control Wheat Rust (Dimethy1)pheny1(1,2,4-triazol-1ylmethyl)silane 90 (4-Bromopheny1) dimethyl(1H-1,2,4tr iazol-l-y ImethyDsilane 80 (l,l'-8iphenyl-4-yl)dimethyl(lH1,2,4-tr iazol-l-y ImethyDsilane 100 (4-Chlorophenyl)dimethyl(1H-1,2,4triazol-l-ylmethyl)silane 100 Butyl(4-chlorophenyl)methyl(lH1,2,4-tr iazol-l-y ImethyDsilane 80 (3,4-Dichlorophenyl)dimethy1(1H1,2,4-tr iazol-l-y ImethyDsilane 60 Compound % Control Wheat Rust 119 Table 1 (continued) (2,4-Dichlorophenyl)dimethyl(lH1.2.4- triazol-l-ylmethyl)silane 90 bis(4-Chlorophenyl)(methyl)(1H1.2.4- triazol-l-ylmethy1)silane 90 Dimethy1(4-fluoropheny1)(1H-1,2,4triazol-l-ylmethyl)silane 100 [4-(1,1-Dimethylethy1)phenyl]dimethyl (1H-1 ,2,4-triazol-l-ylmethyl)silane 80A Buty1(2,4-dichloropheny1)methy1(1H1.2.4- triazol-l-ylmethyl)silane 100 bis(2,4-Dichlorophenyl)(methyl)(1H1.2.4- triazol-l-ylmethyDsilane 100 (2,4-0ichloTophenyl)methyl(phenyl)(1H-1,2,4-triazol-l-ylmethyDsilane 100 (4-Chlorophenyl)methy1(pheny1)(1H1,2,4-triazol-l-ylmethyDsilane 100 (4-Fluoropheny1)methy1(pheny1)(1H1,2,4-triazol-l-ylmethyDsilane 90 Dodecyl(dimethyl)(1H-1,2,4-triazoll-y lmethyl)silane looA [4-(4-Chlorophenoxy)phenyl]dimethyl(1H-1,2,4-triazol-l-ylmethyDsilane 90 (3,5-0ichlorophenyl)dimethyl(lH1.2.4- triazol-l-ylmethyDsilane 80 (1,1'-Bipheny 1-4-yl) buty 1 (me thyl)(1H-1,2,4-triazol-l-yImethyDsilane 90 bis (1,1'-Bipheny 1-4-yl) (methyl)(1H1.2.4- triazol-l-yImethyDsilane 80 (l,l'-Biphenyl-4-yl)methyl(phenyD(1H-1,2,4-triazol-l-ylmethyDsilane 100 (1,1'-Bipheny1-3-yl)dimethy1(1H-1,2,4triazol-l-ylmethyDsilane 80 Compound X Control Wheat Rust 120 Table 1 (continued) 2-Chlorophenyl(methyl)phenyl(lH-l,2,4triazol-l-ylmethyl)silane 80 [bis(2-Chlorophenyl)lmethyl(1H-1,2,4triazol-l-ylmethyl)silane 100 (1,1'-Biphenyl-4-yl)dimethyl(lH-l,2,410 triazol-l-ylmethyl)silane, 4-dodeoylbenzenesulfonic acid salt 100 (1,1'-Biphenyl-4-yl)dimethyl(lH-l,2,4triazol-l-ylmethyl)sllane, 1:1 complex with zinc (II) chloride 100 (1,1'-Bipheny1-4-y1)dimethyl(1H-1,2,415 triazol-l-ylmethyl)silane, 1:1 complex with manganous sulfate 90 2-Chlorophenyl(4-chlorophenyl)methyl(1H-1,2,4-triazol-l-ylmethyl)silane 100 [bis(2-Fluorophenyl)]methyl(lH20 1,2,4-triazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 90 [bis(2-Fluorophenyl)]methyl(lH1,2,4-triazol-l-ylmethyl)silane, 2:1 complex with cupric chloride 100 (1,1'-Bipheny1-4-yl)dimethyl(lH25 imidazol-l-ylmethyl)silane 100 (4-Chlorophenyl)(lH-imidazol-1ylmethyDdimethyisilane 50 Butyl(4-chlorophenyl)(lH-imidazoll-ylmethyl)methylsilane 90 (lH-Imidazoi-l-ylmethyl)dimethyl(4-phenoxyphenyl)silane 60 Dimethyl(lH-imidazol-l-ylmethyl)(4-methoxyphenyl)silane 60 (2,4-Dichlorophenyl)dimethyl(lH55 imldazol-l-ylmethyl)silane 90 121 Table 1 (continued) Compound % Control Wheat Rust bis(4-Fluorophenyl)(lH-imidazol-1- ylmethyDmethylsilane 100 Dimethyl(4-fluorophenyl)(lH-imidazol-l-ylmethyl)silane 80 Oimethyl(lH-imidazol-l-ylmethyl)(4-trifluoromethylphenyl)silane 100A Buty1(2,4-dichlorophenyl)(lH-imldazol-l-ylmethyl)methylsiiane 100 bis(2,4-0ichlorophenyl)(lH-imidazol1-ylmethyl)methylsilane 100 2,4-Dichlorophenyl(lH-imidazol-lylmethyl)methyl(phenyl)silane 90 4-Chlorophenyl(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 OodecyKdimethyl)(lH-imidazol-1ylmethyl)silane 80ft [4-(4-Chlorophenoxy)phenyl]dimethy1(lH-imidazol-l-ylmethyl)silane 90 Butyl(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 90 (1,1'-Biphenyl-4-yl)butyl(lH-imidazol-l-ylmethyl)methylsilane 100 (1,1'-Bipheny1-4-yl)(lH-imidazol1-ylmethyl)methyl(phenyl)silane 100 (l,l'-Biphenyl-3-yl)dimethyl(lHimidazol-l-ylmethy1)silane 90 (4-Bromopheny1)(lH-imidazol-l-y1methyl)methyl(phenyl)silane 90 (1,1*-Biphenyl-4-yl)dimethyK1Himidazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 (2-Chlorophenyl)(4-chlorophenyl)(1Himidazol-l-ylmethyl)methylsilane 100 122 Table 1 (continued) Compound % Control Wheat Rust (2-Chlorophenyl)(dimethyl)(lH-imidazol-l-ylmethyl)silane 80 A Compound applied at a concentration of 200 ppm.

INSERT Q 123 Example 69 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). These suspensions were sprayed to the point of run-off on cucumber seedlings. The following day, the plants were inoculated with a spore suspension of the fungus Eryslphe cichoracearum, causal agent of cucumber powdery mildew, and incubated in a growth room for 7 days.

Oisease ratings were then made. Percent disease control is shown in the following table. Treated plants had little or no powdery mildew in contrast to untreated plants which were covered with powdery mildew. Phytotoxicity in the form of growth reduction or hormonal effects was observed on some of the plants in association with disease control.

Table 2 Compound % Control Cucumber Powdery Mildew (Oimethyl)pheny1(1,2,4-triazol-1ylmethyDsilane Ethyldimethyl(lH-l,2,4-triazol-lylmethyl)silane Butyldimethyl(lH-l,2,4-triazol-lylmethyl)silane 100 100 100 Dimethy1(4-methylphenyl)(1H-1,2,4tr iazol-l-y ImethyDsilane iooga (4-Bromophenyl)dimethy1(1H-1,2,4tr iazol-l-y ImethyDsilane 100G 124 Table 2 (continued) % Control Cucumber Compound Powdery Mildew (1,1'-Bipheny 1-4-y DdimethyHlH1,2,4-triazol-l-ylmethyl)silane 100 (4-Chloropheny1)dimethyKlH-1,2,4triazol-l-ylmethyl)silane 100 10 Buty 1 (4-chlor opheny Dmethy 1(1H1,2,4-triazol-l-ylmethyl)silane 100G Dimethy1(1-naphthalenyl)(1H-1,2,4triazoi-l-ylmethyl)silane 100 (3,4-Dichlorophenyl)dimethy1(1Hl,2,4-triazol-l-ylmethyl)silane 100 15 Dimethyl(4-phenoxyphenyl)(lH-l,2,4- triazol-l-ylmethyl)silane 70 Dimethyl(4-methoxyphenyl)(lH-1,2,4triazol-l-ylmethyl)silane 100 20 (2,4-Dlchlorophenyl)dimethy1(1H1,2,4-triazol-l-ylmethyl)silane lOOHB bis(4-Chlorophenyl)(methyl)(1H1,2,4-triazol-l-yImethyl)silane 100 (lH-l,2,4-Triazol-l-ylmethyl)tri- phenylsilane 100 25 Methyldiphenyl(1H-1,2,4-triazol-lylmethyl)silane 100G (1,1'-Bipheny 1-4-y Ddime thyl(4H1,2,4-triazol-4-ylmethyl)silane 90 30 bis(4-Fluorophenyl)(methyl)(lH1,2,4-triazol-l-ylmethyl)silane 100G Dimethyl(4-fluorophenyl)(1H-1,2,4triazol-l-ylmethyl)silane 100G DimethyK4-methylthiophenyl)(1H1,2,4-triazol-l-yImethyl)silane 100 125 Table 2 (continued) % Control Cucumber Compound Powdery Mildew DimethyK1H-1,2,4-triazol-l-y1methyl)(4-trifluoromethylphenyl)silane 100G Dime thy KlH-1,2,4-triazol-l-y 1methyl)(3-trifluoromethylpheny1)silane 100 Dimethy1(1H-1,2,4-triazol-l-ylmethyl)(2-trifluoromethylphenyl)silane 100 (2-Methoxyphenyl)dimethy1(1H-1,2,4triazol-l-ylmethyl)silane 100G Buty1(2,4-dichlorophenyl)methy1(1H1.2.4- trlazol-l-ylmethyl)silane 100G bis(2,4-Dichlorophenyl)(methyl)(1H1.2.4- triazol-l-ylmethy1)s ilane 100G (2,4-0ichlorophenyl)methyl(phenyl)(1H-1,2,4-triazol-l-ylmethyl)silane 100G (4-Chlorophenyl)methy1(phenyl)(1H— 1.2.4- triazol-l-ylmethyl)silane 100G (4-Fluoropheny1)methyl(phenyl)(1H1,2,4-triazol-l-ylmethyl)silane 100 Butyl(methyl)phenyl(1H-1,2,4-triazoll-y lmethyl)silane 100 (2,3-Dimethoxyphenyl)dimethy1(1H1,2,4-triazol-l-ylmethyl)silane 100G (2,6-Dimethoxypheny1)dimethy1(1H1,2,4-triazol-l-ylmethyl)silane 100G Dodecyl(dimethyl)(lH-l,2,4-triazoll-ylmethyl)silane 60^ (2-Chlorophenyl)dimethyl(1H-1,2,4triazol-l-ylmethyl)silane 100G [4-(4-Chlorophenoxy)phenyl)dimethyl(1H-1,2,4-triazol-l-ylmethy1)silane 80 126 Table 2 (continued) % Control Cucumber Powdery Mildew Compound (1,1 ’-Biphenyl-4-yl)butyl(methyl)(1H-1,2,4-triazol-l-ylmethyl) silane 100 Buty1(4-fluorophenyl)methyi(lH-1,2,4triazol-l-ylmethyl)silane 100 bis(l,1·-Bipheny1-4-yl)(methyl)(IH— 1,2,4-triazol-l-ylmethyl)silane 100 (l,l'-Biphenyl-4-yl)methyl(phenyl)(1H-1,2,4-triazol-l-ylmethyl)silane 100 (1,1-Dimethylethoxy)methy1(phenyl)(1H-1,2,4-triazol-l-ylmethyl) silane 100 Methy1(phenyl)(2-propoxy)(1H-1,2,4triazol-l-ylmethyl)silane 100 (1,1,-Biphenyl-2-yl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane 90 2-Chloropheny1(methy1)phenyK1H-1,2,420 triazol-l-ylmethyl)silane 100 4-Bromophenyl(methyl)phenyl(1H-1,2,4triazol-l-ylmethyDsilane 100 [bis(2-Chloropheny1)lmethyl(1H-1,2,4triazol-l-ylmethyl)silane 100 Cyclohexyl(dimethyl)(1H-1,2,4-triazoll-ylmethyl)silane 100G [bis(4-Bromophenyl)]methyl(lH-l,2,4triazol-l-ylmethyl)silane BOG (1,1'-Bipheny 1-4-y Ddimethy K1H-1,2,4triazol-l-ylmethyl)silane, 4-dodecyl30 benzenesulfonic acid salt 100 (1,1*-Bipheny1-4-y1) dimethyl(1H-1,2,4triazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 (1,11 -Bipheny 1-4-y Ddimethy 1( 1H-1,2,4· triazol-l-ylmethyl)silane, 1:1 complex with zinc (IX) chloride 5337 8 127 Table 2 (continued) % Control Cucumber Powdery Mildew Compound (1,1'-Biphenyl-4-yl)dimethyl(lH-l,2,4txiazol-l-y ImethyDsilane, 1:1 complex with manganous sulfate 90 2-Chlarophenyl(4-chlorophenyl)methyl(1H-1,2,4-triazol-l-yImethyDsilane 100 Phenyl[bis(2-propoxy)](lH-l,2,4tr iazol-l-y ImethyDsilane 100 [bis(2-Fluorophenyl)]methyl(lH1,2,4-tr iazol-l-y ImethyDsilane, 1:1 complex with cuprous chloride 100 [bis(2-Fluorophenyl)]methyl(lH1,2,4-triazol-l-ylmethyl)silane, 2:1 complex with cupric chloride 100 Dimethy1(ΙΗ-imidazol-l-ylmethy1)phenylsilane 100 EthyKIH-imidazol-l-ylmethy1)dimethylsilane 100 Butyl(lH-imidazol-l-ylmethyl)- dimethylsilane 100 (lH-Imidazol-l-ylmethyl)dimethyl(4-methylphenyl)silane 100GA (4-Bromophenyl)(ΙΗ-imidazol-l-y1methyl)dimethylsilane 100 (1,1'-Biphenyl-4-yl)dimethyl(lHimidazol-l-ylmethyl)silane 100 (4-ChlorophenyD(lH-imidazol-1ylmethy1)dimethylsilane 100 Buty1(4-chlorophenyl)(lH-imidazol1-y lmethy Dmethy lsilane 100G (ΙΗ-Imidazol-l-ylmethyl)dimethy1(1-naphthalenyl)silane 100 128 Table 2 (continued) X Compound Control Cucumber Powdery Mildew (3,4-Dichlorophenyl)(lH-imidazoll-ylmethyl) dimethylsilane 100 (lH-Imidazol-I-ylmethyl)diniethyl(4-phenoxyphenyl)silane 100 Dimethy1(lH-imidazol-l-ylmethyl)(4-methoxyphenyl)silane 100 (2,4-Dichlorophenyl)dimethyl(lH- imidazol-l-ylmethyl)silane ioohb bis(4-Chlorophenyl)(lH-imidazol-l- ylmethyl)methylsilane 100 (lH-Imidazol-l-ylmethy1)triphenylsilane 100 Diphenyl(lH-imidazol-l-ylmethyl)methylsilane 100 bis(4-Fluorophenyl)(lH-imidazol-1ylmethyUmethylsilane 100 OimethyK4-fluorophenyl)(iH-imidazol-l-ylmethy1)silane 100G Dimethyl(lH-imidazol-l-ylmethyl)(4-methylthiophenyl)silane 100 Dimethyl(lH-imidazol-l-ylmethyl)(4-trifluoromethylphenyl)silane 100 Dimethyl(ΙΗ-imidazol-l-ylmethyl)(3-trifluoromethylphenyl)silane 80 [4-(1,l-Oimethylethyl)phenyl](lHimidazol-l-ylmethyl)dimethylsilane 80 (lH-Imidazol-l-ylmethy1)dimethy1(2-trifluoromethylphenyl)silane 100G Butyl(2,4-dichlorophenyl)(lH-imidazol-l-ylmethyl)methylsilane 100G 129 Table 2 (continued) % Control Cucumber Powdery Mildew 5337 8 Compound bis(2,4-Dichlorophenyl)(lH-imidazoll-ylmethyl)methylsilane 100 (2,4-Dichlorophenyl)(lH-imidazol-ly lmethyl) methy 1( pheny Dsilane 100 (4-Chlorophenyl)(ΙΗ-imidazol-l-y1methyl)methyl(phenyl)silane 100 (4-Fluoropheny1)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 (ΙΗ-Imidazol-l-ylmethyl)(2-methoxyphenyDdimethylsilane 100G (2,3-Dimethoxyphenyl)(lH-imidazoll-ylmethyl)dimethylsilane 100 Dodecy1( dimethyl)(lH-imidazol-1ylmethyl)silane 55 (2-Chlorophenyl)(IH-imidazol-l-ylmethyDdimethylsilane 100 [4-(4-Chlorophenoxy)phenyl]dimethyl(IH-imidazol-l-ylmethyDsilane 100 Butyl(ΙΗ-imidazol-l-ylmethyl)methyl(phenyl)silane 100 (1,1’-Bipheny1-4-yl)butyl(lH-imidazol-l-ylmethyDmethylsilane 100 Buty1(4-fluoropheny1)(lH-imidazoll-ylmethyl)methylsilane 100 Oibuty1(ΙΗ-imidazol-l-ylmethy1)methylsilane 100 (1,1'-Bipheny1-4-yl)(lH-imidazol1-ylmethyl)methyl(phenyl)silane 100 (1,l-Dimethylethoxy)(lH-imidazol-lylmethyl)methyl(phenyl)silane 100 130 Table 2 (continued) X Control Cucumber Compound Powdery Mildew 3 7 0 (ΙΗ-Imidazol-l-ylmethyDmethyl(phenyl)(2-propoxy)silane 90 (ΙΗ-Imidazol-l-ylmethyl)[bis(4methoxyphenyl)]methylsilane 50 1Q (l,l'-Biphenyl-2-yl)dimethyl(lH1U imidazol-l-ylmethyl)silane 50 (2-Chlorophenyl)(IH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 (4-Bromophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 [bis(2-Chlorophenyl)](lH-imidazoll-ylmethyl)methylsilane 100 Cyclohexyl(dimethyl(lH-imIdazol-lylmethyDsilane 100G ?n [bis(4-Bromophenyl)](lH-imidazol-lylmethyDmethylsilane 100 (1,1'-Bipheny1-4-y1)dimethy1(1Himidazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 (2-Chlorophenyl)(4-chlorophenyl)(1H25 imidazol-l-ylmethyl)methylsilane 100 (2-Chlorophenyl)(dimethyl)(lH-imidazol-l-ylmethyllsilane 80 *G = growth reduction; and θΗ = hormonal effects. INSERT R 131 Example 70 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). These suspensions were sprayed to the point of run-off on barley seedlings. The following day, the plants were inoculated with a spore suspension of the fungus Erysiphe graminis, causal agent of barley powdery mildew, and incubated in a growth room for 7 days. Disease ratings were then made. Percent disease control is shown in the following table. Treated plants had little or no powdery mildew in contrast to untreated plants which were covered with powdery mildew.

Table 3 Compound Butyl(4-chlorophenyl)methyl(lH1,2,4-triazol-l-ylmethyl)silane (3,4-Dichlorophenyl)dimethy1(1H1,2,4-triazol-l-ylmethyl)silane Dimethy1(4-methoxyphenyl)(lH-1,2,4 triazol-l-ylmethyl)silane (2,4-Dichlorophenyl)dimethyl(lH1,2,4-triazol-l-ylmethyl)silane bis(4-Chlorophenyl)(methyl)(1H1,2,4-triazol-l-ylmethyl)silane (1H-1,2,4-Trlazol-l-ylmethyl)triphenylsilane Methyldiphenyl(lH-l,2,4-triazol-lylmethyl)silane Dimethyl(lH-l,2,4-triazol-l-ylmethyl)(2-trifluoromethylphenyl) silane X Control Barley Powdery Mildew 100 100 100 100 100 100 100 3 3 7 8 132 Table 3 (continued) % Control Barley Powdery Mildew Compound Dodecyl(dimethyl)(lH-l,2,4-triazol 1-y ImethyDsilane Butyl(4-chlorophenyl)(IH-imldazol1-y lmethy Dmethy lsilane (3,4-Dichloropheny1)(lH-imidazoll-ylmethyl)dimethylsilane Oimethy1(lH-imidazol-l-ylmethyl)(4-methoxyphenyl)silane (2,4-Dichlorophenyl)dimethyl(1Himidazol-l-y ImethyDsilane bis(4-Chlorophenyl)(lH-imidazol-1ylmethyDmethylsilane Diphenyl(lH-imidazol-l-ylmethyl)methylsilane Dimethyl(lH-imidazol-l-ylmethyl)2θ (4-trifluoromethylphenyl)silane Dodecyl(dimethyl)(lH-imidazol-1ylmethyDsilane 100A 100 100 100 100 100 100 100AA Compound applied at a concentration of 200 ppm. 133 Example 71 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). These suspensions were sprayed to the point of run-off on apple seedlings. The following day, the plants were inoculated with a spore suspension of the fungus Venturia inaequalis, causal agent of apple scab, and Incubated in a saturated humidity chamber at 20° for 24 hours and then in a growth room for an additional 10-12 days. Disease ratings were then made and recorded as shown in the following table. Treated plants had fewer apple scab lesions when compared to untreated plants which were covered with scab lesions. Phytotoxicity expressed as growth reduction was observed on some of the plants in association with disease control.

% Control Apple Scab Table 4 Compound Dimethyl(4-methylphenyl)(1H-1,2,4triazol-l-ylmethyl)silane 50Ga (4-Bromophenyl)dimethyl(1H-1,2,4triazol-l-ylmethyl)silane 90G (l,l'-Biphenyl-4-yl)dimethyl(lH1,2,4-triazol-l-ylmethyl)silane 100 (4-Chloropheny1)dimethy1(1H-1,2,4triazol-l-ylmethyl)silane 100 Buty1(4-chlorophenyl)methy1(1H1,2,4-triazol-l-ylmethyl)silane 100G Dimethyl(1-naphthalenyl)(1H-1,2,4triazol-l-ylmethyl)silane 50 3 3 7 8 134 Table 4 (continued) Compound % Control Apple Scab - (3,4-Dichloropheny1)dimethy1(1H3 l,2,4-triazol-l-ylmethyl)silane 80 Dimethy1(4-phenoxyphenyl)(1H-1,2,4triazol-l-ylmethyl)silane 100 Dimethyl(4-methoxyphenyl)(1H-1,2,4triazol-l-ylmethyl)silane 100 (2,4-Dichloropheny1)dimethy1(1H1,2,4-triazol-l-ylmethyl)silane 100 bis(4-Chlorophenyl)(methyl)(1H1.2.4- triazol-l-ylmethyl)silane 100 MethyIdiphenyl(1H-1,2,4-triazol-l15 ylmethyl)silane 100 (1,1'-8iphenyl-4-yl)dimethyl(4H1.2.4- triazol-4-ylmethyl)silane 80 bis(4-Fluoropheny1)(methy1)(1H1.2.4- triazol-l-ylmethyl)silane 100 Dimethy1(4-fluoropheny1)(1H-1,2,4triazol-l-ylmethyl)silane 80C° Dimethyl(4-methylthiophenyl)(lH1,2,4-triazol-l-ylmethyl)silane 60 ,, Dimethyl(lH-l,2,4-triazol-l-ylmethyl)(2-trifluoromethylphenyl)silane 65GA»C (2-Methoxyphenyl)dimethyKlH-1,2,4triazol-l-ylmethyl)silane 80 Butyl(2,4-dichlorophenyl)methyl(lH1,2,4-triazol-l-ylmethyl)silane 100G bis(2,4-0ichlorophenyl)(methyl)(1H1.2.4- triazol-l-ylmethyl)silane 100 (2,4-0ichlorophenyl)methyl(phenyl)(1H-1,2,4-triazol-l-ylmethyl)silane 100G ,, (4-Chlorophenyl)methyl(phenyl)(1H1.2.4- triazol-l-ylmethyl)silane 100 135 Table 4 (continued) Compound % Control Apple Scab (4-Fluorophenyl)methyl(phenyl)(1H1,2,4-triazol-l-ylmethyl)silane Butyl(methyl)phenyKlH-1,2,4-triazoll-y ImethyDsilane Dodecyl(dimethyl)(lH-l,2,4-triazoll-ylmethyl)silane (2-Chlorophenyl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane [4-(4-Chlorophenoxy)pheny1Jdimethy1(1H-1,2,4-triazol-l-ylmethyl)silane (l,l'-Biphenyl-4-yl)butyl(methyl)(1H-1,2,4-triazol-l-y ImethyDsilane Buty 1 (4-f luor opheny 1) methy KlH-1,2,4triazol-l-ylmethyl)silane (1,1'-Bipheny1-4-yl)methy1(phenyl)(1H-1,2,4-triazol-l-y ImethyDsilane (1,1'-Biphenyl-2-yl)dimethyl(1H-1,2,4triazol-l-ylmethyl)silane (l,l'-Biphenyl-3-yl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane 2-Chlorophenyl(methyl)phenyl(lH-l,2,4triazol-l-ylmethyl)silane 4-Bromopheny1(methy1)phenyl(1H-1,2,4triazol-l-y ImethyDsilane [bis(2-Chlorophenyl)]methyl(lH-l,2,4triazol-l-ylmethyl)silane [bis(4-Bromophenyl)]methyl(lH-l,2,4triazol-l-ylmethyl)silane (l,l'-Biphenyl-4-yDdimethyl(lH-l,’2,4triazol-l-ylmethyl)silane, 4-dodecylbenzenesulfonic acid salt 100 40BC.0 100 100 100 100 100 100 136 Table 4 (continued) Compound % Control (1,1'-Bipheny1-4-yl)dimethy1(1H-1,2,4triazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride (1,1'-Bipheny1-4-yl)dimethyXlH-l,2,4triazol-l-ylmethyl)silane, 1:1 complex with zinc (II) chloride (l,l'-Biphenyl-4-yl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane, 1:1 complex with manganous sulfate 2-Chloropheny1(4-chlorophenyl)methyl(1H-1,2,4-triazol-l-ylmethyDsilane 2-ChlorophenyXdimethy1)(1H-1,2,4triazol-l-y lmethy Dsilane (1,1'-Bipheny1-4-yl)dimethyi(lHimidazol-l-y lmethy Dsilane Butyl(4-chlorophenyl)(lH-imidazol1-ylmethyl)methyls!lane (ΙΗ-Imidazol-l-ylmethyl)dimethy1(1-naphthalenyl)silane (3,4-Dichlorophenyl)(lH-imidazol1-ylmethyl)dimethylsilane (ΙΗ-Imidazol-l-ylmethy1)dimethy1(4-phenoxyphenyl)silane (2,4-Dichlorophenyl)dimethyl(lHimidazol-l-y lmethy Dsilane Diphenyl(ΙΗ-imidazol-l-ylmethy1)methylsilane bis(4-Fluorophenyl)(lH-imidazol-1ylmethyl)methylsilane DimethyXlH-imidazol-l-ylmethyD(4-tri fluoromethy lpheny Dsilane [4-(1,1-Dimethylethy1)phenyl](1Himidazol-l-ylmethyDdimethylsilane 137 Table 4 (continued) Compound % Control Apple Scab Buty1(2,4-dichlorophenyl)(lH-imidazol-l-ylmethyl)methylsilane 100B bis(2,4-Dichlorophenyl)(lH-imidazol1-y lmethyDmethylsilane 40 (2,4-Dichlorophenyl)(lH-imidazol-1ylmethyl)methyl(phenyl)silane 80 (4-Chloropheny1)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 (4-Fluorophenyl)(lH-imldazol-l-ylmethyl)methyl(phenyl)silane 100 (lH-Xmidazol-l-ylmethyl)(2-methoxyphenyl)dimethylsilane 60 (2-Chlorophenyl)(lH-imidazol-l-ylmethyl)dimethylsilane 90 ButyKlH-imidazol-l-ylmethy1)methyl(phenyl)silane 80 (1,1'-Bipheny1-4-yl)butyKlH-imidazol-l-y lmethyDmethylsilane 100 Buty1(4-fluorophenyl)(IH-imidazo11-y lmethyDmethylsilane 80 Dibutyl(lH-imidazol-l-ylmethy1)methylsilane 30 bis(l,1'-Bipheny1-4-yl)(lH-imidazol-l-ylmethyl)methylsilane 50 (lH-lmidazol-l-ylmethyl)[bis(4methoxyphenyl)Imethylsilane 50 (1,1 '-Bipheny 1-2-y Ddimethy 1( 1Himidazol-l-ylmethyl)silane 90 (1,1' -Bipheny 1-3-y Ddimethy KlHimidazol-l-y lmethyDsilane 90 (2-Chlorophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 138 Table 4 (continued) Compound % Control Apple 5 (4-Bromophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 30 [bis(2-Chlorophenyl)](lH-imidazoil-ylmethyl)methylsilane 60 Dimethyl(ΙΗ-imidazol-l-ylmethy1)10 (4-methylsulfonylphenyl)silane 80 Cyclohexy1(dimethy1(lH-imidazol-1ylmethyl)silane 100B [bis(4-Bromophenyl)](lH-imidazol-lylmethyDmethylsilane 50 15 (1,l'-Biphenyl-4-yl)dimethyl(lHimidazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 (2-Chlorophenyl)(4-chlorophenyl)(1Himidazol-1-ylmethyDmethylsilane 80 (ΙΗ-Imidazol-l-ylmethy1)pheny1[bis(2-propoxy)]silane 70 (2-Chlorophenyl)(dimethyl)(lH-imidazol-l-ylmethyl)silane 60 9AG = growth reduction. 3 BC = chlorosis. ^compound applied at a concentration of 400 ppm. °B = burn.

INSERT S 139 Example 72 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). These suspensions were sprayed to the point of run-off on corn seedlings. The following day, the plants were inoculated with a spore suspension of Helminthosporium maydis, causal agent of southern corn leaf blight, and incubated in a saturated humidity chamber at 20° for 24 hours and then in a growth room for an additional 7 days, when disease ratings were made.

Percent disease control is shown in the following table. Treated plants had few or no lesions while the untreated plants had numerous lesions on each leaf. Phytotoxicity expressed as growth reduction was observed on some of the plants in association with disease control.

Table 5 % Control of Southern Compound Corn Leaf Blight (4-Bromophenyl)dimethyKlH-1,2,4triazol-l-ylmethyl)silane 90 (1,1'-Biphenyl-4-yl)dimethyK1H1,2,4-triazol-l-ylmethyl)silane 90 (3,4-Dichlorophenyl)dimethy1(1H1,2,4-triazol-l-ylmethyl)silane 90 Dimethyl(4-methoxyphenyl)(1H-1,2,4triazol-l-ylmethyl)silane 90 (2,4-0ichlorophenyl)dimethyl(lH1,2,4-triazol-l-ylmethyl)silane 90 bis(4-Chlorophenyl)(methyl)(lH1,2,4-triazol-l-ylmethyl)silane 80 140 Table 5 (continued) 333 73 % Control of Southern Compound Methyldiphenyl(lH-l,2,4-triazol-l- ylmethyDsllane 80 (1,1 ‘-Bipheny1-4-yl)dimethy1(4H1,2,4-triazol-4-ylmethyl)silane 100 10 bis(4-Fluorophenyl)(methyl)(lH1,2,4-triazol-l-ylmethyl)silane 100 Dimethy1(4-fluorophenyl)(1H-1,2,4triazol-l-ylmethyl)silane 90 OimethyK4-methylthiophenyl)(1H1,2,4-triazol-l-ylmethyl)silane 80 15 0imethyl(lH-l,2,4-triazol-l-ylmethyl)(4-trifluoromethylpheny1)silane 50 20 [4-(1,1-Dimethylethyl)phenyl]dimethyl(lH-l,2,4-triazol-l-ylmethyl)silane 60 (2-Methoxyphenyl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane 70 Butyl(2,4-dichlorophenyl)methyl(lH1,2,4-triazol-l-ylmethyl) silane 100 25 bis(2,4-0ichlorophenyl)(methyl)(IH— 1,2,4-triazol-l-ylmethyl)silane 80 (4-Chlorophenyl)methy1(phenyl)(IH— 1,2,4-triazol-l-ylmethyl)silane 90 30 (4-Fluorophenyl)methyl(phenyl)(1H1,2,4-triazol-l-ylmethyl) silane 90 (2-Chlorophenyl)dimethyl(lH-l,2,4triazol-l-ylmethy1)silane 100 [4-(4-Chlorophenoxy)phenyl]dimethy1(1H-1,2,4-triazol-l-ylmethyl)silane 50 35 (3,5-Dichlorophenyl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane 40 141 Table 5 (continued) % Control of Southern Compound Corn Leaf Blight (1,11-Biphenyl-4-yDbutyl(methyl)(1H-1,2,4-triazol-l-ylmethyljsilane (l,l’-Biphenyl-4-yl)methyl(phenyD(1H-1,2,4-triazol-l-ylmethyl)silane [bis(4-Methoxyphenyl)3methyl(lH-l,2,4triazol-l-ylmethyl)silane (1,l'-Bipheny1-2-yl)dimethyKlH-1,2,4triazol-l-ylmethyl)silane (1,1'-Bipheny1-3-y1)dimethy1(1H-1,2,4triazol-l-ylmethyl)silane 2-Chlprophenyl(methyl)phenyl(lH-l,2,4triazol-l-ylmethylJsilane 4-Bromophenyl(methyl)phenyl(lH-l,2,4triazol-l-ylmethyl)silane [bis(2-Chlorophenyl)]methyl(lH-l,2,420 triazol-l-ylmethyl)silane Cyelohexyl(dimethyl)(1H-1,2,4-triazoll-y ImethyDsilane (l,l'-Biphenyl-4-yl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane, 4-dodecy 125 benzenesulfonic acid salt (1,1'-Bipheny1-4-yl)dimethy1(1H-1,2,4triazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride (1,1'-Biphenyl-4-yl)dimethyl(lH-l,2,4triazol-l-y ImethyDsilane, 1:1 complex with zinc (II) chloride (1,1'-Bipheny1-4-yl)dimethy1(1H-1,2,4triazol-1-y ImethyDsilane, 1:1 complex with manganous sulfate 2-Chloropheny1(4-chlorophenyl)methyl35 (1H-1,2,4-triazol-l-ylmethyl)silane 100 100 100 100 100 142 Table 5 (continued) % Control of Southern Compound Corn Leaf Blight (1,1'-Biphenyl-4-yl)dimethy1(1Himidazol-l-ylmethyl)silane 90 Butyl(4-chlorophenyl)(lH-imidazoll-ylmethyl)methylsilane 50 1n (3,4-Dichlorophenyl)(lH-imidazolu l-ylmethyl)dimethylsilane 70 (2,4-Dichlorophenyl)dimethyl(lHimidazol-l-ylmethyl)silane 70 bis(4-Chlorophenyl)(lH-imidazol-lylmethyDmethylsilane 60 (lH-Imidazol-l-ylmethyl)triphenylsilane 50 Dipheny1(ΙΗ-imidazol-l-ylmethy1)methylsilane 60 __ bis(4-Fluorophenyl)(lH-imidazol-1ylmethyDmethylsilane 60 [4-(1,1-Oimethylethyl)phenyl](1H. imidazol-l-ylmethyDdimethylsilane 70 (lH-Imidazol-l-ylmethyl)dimethyl(2-trifluoromethylphenyl)silane 90 Buty1(2,4-dichlorophenyl)(lH-imidazol-l-ylmethyl)methylsilane 80 bis(2,4-Dichloropheny1)(lH-imidazoll-ylmethyl)methylsilane 80 ,n (4-Fluorophenyl)(ΙΗ-imidazol-l-y1methyl)methyl(phenyl)silane 80 (2,6-Dimethoxyphenyl)(dimethyl){1Himidazol-l-ylmethyl)silane 50 Dibutyl(lH-imidazol-l-ylmethyl)methylsilane 90 143 Table 5 (continued) % Control of Southern Compound Corn Leaf Blight (1,1'-Biphenyl-4-y1)(IH-imidazol1-ylmethyl)methyl(phenyl)silane 80 (1,1'-Bipheny1-3-yl)dimethy1(1Himidazol-l-ylmethyl)silane 90 [bis(2-Chlorophenyl)](lH-imidazoll-ylmethyl)methylsilane 90 Cyclohexyl(dimethyl(lH-imidazol-1ylmethyl)silane 50 INSERT T 53373 144 Example 73 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). These suspensions were sprayed to the point of run-off on peanut seedlings. The following day, the plants were inoculated with a spore suspension of Cercospora arachl10 dlcola, causal agent of peanut early leafspot, and incubated in a saturated humidity chamber at 27° for 24 hours and then in a growth room for an additional 14 days, when disease ratings were made. The results are shown In the following table. Treated plants had few or no leafspots while the untreated plants had numerous leafspots. Phytotoxicity expressed as burn was observed in association with disease control for some treated plants.

Table 6 % Control Peanut Compound Early Leafspot bis(4-Chlorophenyl)(methyl)(1H1.2.4- triazol-l-ylmethyl)silane 100 Methyldiphenyl(lH-l,2,4-triazol-lylmethyDsilane 100 (1,1'-Bipheny1-4-yDdimethy1(1H1.2.4- triazol-l-ylmethy1)silane 100 (4-Chlorophenyl)dlmethyl(lH-l,2,4triazol-l-y lmethyDsilane 90 Dimethyl(1-naphthaleny1)(1H-1,2,4triazol-l-ylmethyl)silane 90 ,, (2,4-Dichlorophenyl)dimethyl(lH’’ l,2,4-triazol-l-ylmethyl)silane 100 145 Table 6 (continued) % Control Peanut Early Leafspot Compound bis(4-Fluorophenyl)(methyl)(1H1,2,4-triazol-l-ylmethyl)silane 100 Dimethyl(4-fluorophenyl)(1H-1,2,4triazol-l-ylmethyDsilane 50 ln [4-(1, 1-Dimethylethyl)phenyl]dimethyl(lH-l,2,4-triazol-l-ylmethyDsilane 35 Dimethy1(1H-1,2,4-triazol-l-y1methyl)(2-trifluoromethylpheny1)silane 25B Butyl(2,4-dichlorophenyl)methyl(lH1.2.4- triazol-l-ylmethyl)silane 100 bis(2,4-0ichlorophenyl)(methyl)(1H1.2.4- triazol-l-ylmethy1)silane 100 (2,4-Dichlorophenyl)methy1(phenyD20 (lH-l,2,4-triazol-l-ylmethyl)silane 100 (4-ChlorophenylJmethyl(phenyl)(1H1.2.4- triazol-l-ylmethyDsilane 100 (4-Fluorophenyl)methyl(phenyl)(1H1,2,4-triazol-l-ylmethyDsilane 100 (2-Chlorophenyl)dimethyl(lH-l,2,4triazol-l-ylmethyDsilane 30 (1,1'-Bipheny1-4-yl)butyl(methy1)(1H-1,2,4-triazol-l-ylmethyl)silane 100 bis(1,1*-Bipheny1-4-yl)(methyl)(1H3Q 1,2,4-triazol-l-y ImethyDsilane 80 (1,1'-Bipheny1-4-yl)methyl(pheny1)(1H-1,2,4-triazol-l-ylmethyl)silane 100 [bis(4-Methoxyphenyl)]methyX1H-1,2,4triazol-l-y ImethyDsilane 30 (1,1'-Bipheny1-2-y1)dimethy1(1H-1,2,4triazol-l-ylmethyl)silane 100 03378 146 Table 6 (continued) % Control Peanut Early teafspot Compound (l,l'-Biphenyl-3-yl)dimethyl(lH-l,2,4triazol-l-ylmethyDsilane 90 2-Chloropheny1(methy1)phenyKlH-1,2,4trlazol-l-ylmethyl)sllane 100 ,n 4-Bromophenyl(methy1)phenyl(lH-l,2,4triazol-l-ylmethyl)silane 100 [bis(2-Chlorophenyl)]methyl(lH-l,2,4triazol-l-ylmethyl)silane 100 [bis(4-Bromophenyl)]methyKlH-1,2,4triazol-l-ylmethyl)sllane 100 (l,l'-Biphenyl-4-yl)dImethyl(lH-l,2,4triazol-l-ylmethyl)silane, 4-dodecylbenzenesulfonic acid salt 100 (l,l'-Biphenyl-4-yl)dimethyl(lH-l,2,4triazol-l-ylmethyl)sllane, 1:1 com2Q plex with cuprous chloride 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4triazol-l-yimethyl)silane, 1:1 complex with zinc (II) chloride 100 (1,1'-Biphenyl-4-yl)dimethyKlH-1,2,4triazol-l-ylmethyDsilane, 1:1 com25 plex with manganous sulfate 100 2-Chlorophenyi(4-chlorophenyl)methyl(1H-1,2,4-triazol-l-ylmethyl)silane 90 [bis(2-Fluorophenyl)]methyl(lH1,2,4-triazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 [bis(2-Fluorophenyl)]methyl(1H1,2,4-triazol-l-ylmethyl)silane, 2:1 complex with cupric chloride 100 (1,1'-Biphenyl-4-yl)dimethy1(1Himidazol-l-ylmethyl)silane 100 147 Table 6 (continued) X Control Peanut Compound Early Leafspot (2,4-Dichlorophenyl)dimethyl(lHimidazol-l-ylmethyl)silane 100 Dipheny1(ΙΗ-imidazol-l-ylmethyl)methylsilane 50 bis(4-Fluoropheny1)(lH-imidazol-1y lmethy Dmethylsilane 100 Dimethyl(4-fluorophenyl)(lH-imidazol-l-y ImethyDsilane 60B* DimethyKΙΗ-imidazol-l-ylmethyl)(4-trifluoromethylphenyDsilane 36θ Dimethy1(ΙΗ-imidazol-l-ylmethyl)(3-trifluoromethylphenyl)silane 50 Buty1(2,4-dichloropheny1)(lH-Imldazol-l-ylmethyDmethylsilane . 100 bis(2,4-Dichlorophenyl)(lH-imidazol1-ylmethyl)methylsilane 90 (2,4-Dichlorophenyl)(lH-imldazol-ly lmethy Dmethy 1( phenyl) silane 100 (4-Chlorophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 (4-Fluorophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 (2-Chlarophenyl)(ΙΗ-imidazol-l-y1methyDdimethylsilane 80 (1,11 -Biphenyl-4-yl)butyl(lH-imidazol-l-ylmethyDmethylsilane 90 bis (1,1’-Bipheny1-4-y1)(lH-imidazol-l-ylmethyDmethylsilane 60 (l,l'-8iphenyl-4-yl)(lH-imidazol-l-ylmethyDmethyl(phenyl)silane 80 148 Table 6 (continued) -Λ Compound % Control Peanut Early Leafspot (1,l'-Biphenyl-2-yl)dimethyl(lHimidazol-l-ylmethyl)silane 30 (1,1'-Biphenyl-3-yl)dimethyl(lHimidazol-l-ylmethyl)silane 80 (2-Chlorophenyl)(lH-imidazol-l-ylmethyl)methy1( phenyl)silane 100 (4-Bromophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 90 [bis(2-Chlorophenyl)j(lH-imidazol1-y lmethyDmethylsilane 100 [bis(4-Bromophenyl)](lH-imidazol-ly lmethyDmethylsilane 50 (1,1'-Biphenyl-4-yDdimethy1(1Himidazol-l-ylmethyUsllane, 1:1 complex with cuprous chloride 100 (2-Chlorophenyl)(4-chlorophenyl)(1Himidazol-l-y lmethyDmethylsilane 80AB = Phytotoxic burn. ^Compound applied at a concentration of 400 ppm.

INSERT U 533 78 149 Example 74 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume* and then suspended at a concentration of 80 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on bean seedlings. The following day, the plants were inoculated with a spore suspension of the fungus Uromyces phase10 oli, causal agent of bean rust, and incubated in a saturated humidity chamber at 20° for 24 hours and then in a greenhouse for 7 days. Disease ratings were then made. Percent disease control is shown in the following table. Treated plants had few or no rust pustules in contrast to untreated plants which were covered with rust pustules. Phytotoxicity in the form of growth reduction was observed in association with disease control for some treated plants. . f Table 7 % Control Compound Bean Rust (1,1'-Bipheny1-4-yl)dimethy1(1H1.2.4- triazol-l-ylmethyl)silane 100 (2,4-Dichlorophenyl)dimethyl(lH1.2.4- triazol-l-ylmethyl)silane 30GA bis(4-Chlorophenyl)(methyl)(1H1,2,4-triazol-l-ylmethyl)silane 100G (4-ChlorophenyOmethyl(phenyl)(1H3Q l,2,4-triazol-l-ylmethyl)silane 98B (4-Fluorophenyl)methy1(phenyl)(1H1,2,4-triazol-l-ylmethyl)silane 100B bis(4-Fluorophenyl)(methyl)(1H1,2,4-triazol-l-ylmethyl)silane 98B (1,1'-Bipheny1-4-yl)dimethyl(1Himidazol-l-ylmethy1)silane 100 148 Table 6 (continued) % Control Peanut Compound Early Leafspot (1,1'-Biphenyl-2-yl)dimethyl(lHImidazol-l-ylmethyl) silane 30 (l,l'-Biphenyl-3-yl)dimethyl(lHimidazol-l-ylmethyl)silane 80 1n (2-Chlorophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 (4-Bromophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 90 [bis(2-Chlorophenyl)](lH-imidazol1-y lmethy Dmethy lsilane 100 [bis(4-Bromophenyl)](lH-imidazol-lylmethyDmethylsilane 50 (1,1'-Bipheny1-4-yl)dimethyl(1Himidazol-l-ylmethyDsilane, 1:1 complex with cuprous chloride 100 20 (2-Chlorophenyl)(4-chlorophenyl)(ΙΗimidazol-l-y lmethy Dmethy lsilane 80 Λθ = Phytotoxic burn.

^Compound applied at a concentration of 400 ppm.

INSERT U 149 Example 74 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume* and then suspended at a concentration of 80 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on bean seedlings. The following day, the plants were inoculated with a spore suspension of the fungus Uromyces phaseoil, causal agent of bean rust, and incubated in a saturated humidity chamber at 20° for 24 hours and then in a greenhouse for 7 days. Disease ratings were then made. Percent disease control is shown in the following table. Treated plants had few or no rust pustules in contrast to untreated plants which were covered with rust pustules. Phytotoxicity in the form of growth reduction was observed in association with disease control for some treated plants.

Table 7 5S Control Compound Bean Rust (1,1'-Bipheny1-4-y1)d imethy1(1H1.2.4- triazol-l-ylmethyl)silane 100 (2,4-Dichlorophenyl)dimethyl(lH1.2.4- triazol-l-ylmethyl)silane 30GA bis(4-Chlorophenyl)(methyl)(1H1.2.4- triazol-l-ylmethyl)silane 100G (4-Chlorophenyl)methyl(phenyl)(1H1,2,4-triazol-l-ylmethyl)silane 98° (4-Fluorophenyl)methyl(phenyl)(1H1.2.4- triazol-l-ylmethyl)silane 1008 bis(4-Fluorophenyl)(methyl)(lH1.2.4- triazol-l-ylmethyDsilane 988 (1,1'-Bipheny1-4-y1)dimethy1(1Himidazol-l-ylmethyl)silane 100 5337 8 150 Table 7 (continued) % Control Compound Bean Rust (2,4-0ichlorophenyl)dlmethyl(lH$ imidazol-l-ylmethyl)sllane 83 ftG = growth reduction. ^compound applied at a concentration of 16 ppm 151 Example 75 Compounds of this invention were dissolved in acetone in an amount equal to 5% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 700 ppm of the surfactant TREM 014 (polyhydric alcohol esters). Canned peach halves were dipped in this suspension for three minutes and then placed to air dry in sterile containers. Upon drying, the peach halves were inoculated with two pieces of Monlllnia fructicola mycelium, causal agent of stone fruit brown rot, and incubated in the sterile containers for five days.

At that time the radii of the colonies* growth were measured on each peach. Colonies on treated peaches did not grow or grew only a few milliliters in diameter while those growing on untreated peaches covered the entire surface of the peach. Percent disease contol (percent growth inhibition of colonies on treated peaches as compared to that of colonies on untreated peaches) is expressed in the table below.

Table 8 Compound % Control Brown Rot (Dimethyl)pheny1(1,2,4-triazol-1 ylmethyl)silane (Buty1)dimethyl(lH-l,2,4-triazol-lylmethyl)silane (1,1'-Biphenyl-4-yDdimethy1(1H1,2,4-triazol-l-ylmethy1)silane Dimethyl(4-methoxyphenyl)(1H-1,2,4triazol-l-ylmethyl)silane 100 Butyl(4-chlorophenyl)methyl(lH1,2,4-triazol-l-ylmethyl)silane 152 Table 8 (continued) Compound (2,4-Dichlorophenyl)dimethyl(lH1.2.4- triazol-l-ylmethyl)silane bis(4-Chlorophenyl)(methyl)(lH1.2.4- triazol-l-ylmethyl)silane . n (1,1' -Bipheny 1-4-y DdimethyK 4H1U 1,2,4-triazol-4-ylmethyl)silane bis(4-Fluorophenyl)(methyl)(lH1.2.4- triazol-l-ylmethyl)silane Butyl(2,4-dichlorophenyl)methyl(lH1.2.4- triazol-l-ylmethyl) silane 15 (4-Chlorophenyl)methyl(phenyl)(lH1.2.4- triazol-l-ylmethyl)silane (4-Fluorophenyl)methyl(phenyl)(lH1,2,4-triazol-l-ylmethyl)silane Butyl (4-f luoropheny Dmethy KlH-1,2,4 20 triazol-l-ylmethyl)silane Dibutyl(methyl)(lH-l,2,4-triazol-lylmethyDsilane (1,1' -Biphenyl-4-y DdimethyK 1Himidazol-l-ylmethyl)silane Butyl(4-chlorophenyl)(lH-imidazoll-ylmethyl)methylsilane (ΙΗ-Imidazol-l-ylmethyDdimethyl(4-phenoxyphenyl)silane ,n (2,4-DichlorophenyDdimethy1(1Himidazol-l-ylmethyl)silane DiphenyKlH-imidazol-1-ylmethyl)methylsilane (4-Chlorophenyl)(lH-imidazol-l-ylmethyDmethyl (phenyl) silane % Control Brown Rot 100 100 100 100 (4-Fluoropheny1)(lH-imidazol-l-ylmethyDmethyl (phenyl) silane 153 Example 76 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on rice seedlings. The following day, the plants were inoculated with a mixture of bran and the mycelium of Rhlzoctonla solani, causal agent of sheath blight of rice, and incubated in a growth room for 7 days. Disease ratings were then made. Percent disease control is shown in the following table. Treated plants had little sheath blight in contrast to untreated plants which were covered with sheath blight.

Compound Table 9 % Control of Rice Sheath Blight (1,1’ -Bipheny 1-4-y Ddimethyl(1H-1,2,4-triazol-l-ylmethyl)silane (3,4-Dichlorophenyl)dimethyl(lH1,2,4-triazol-l-ylmethyl)silane bis(4-Fluorophenyl)(methyl)(1H1,2,4-triazol-l-ylmethyl)silane [4-(1,1-Dimethylethyl)phenyl]dimethyKlH-l, 2,4-triazol-l-y 1methyl)silane Buty1(2,4-dichlorophenyl)methyl(lH1,2,4-triazol-l-ylmethyl)silane (4-FluorophenyDmethyl(phenyl)(1H1,2,4-triazol-l-ylmethyl)silane (4-Chlorophenyl)methyl(phenyl)(lH1,2,4-triazol-l-ylmethyl) silane 154 Table 9 (continued) % Control of Compound Rice Sheath Blight Buty1(methyl)phenyl(lH-l,2,4-triazoll-y lmethyDsilane 90 (l,l'-Blphenyl-4-yl)butyl(methyl)(1H-1,2,4-triazol-l-ylmethyl)silane 80 , Butyl(4-fluorophenyl)methyH1H-1,2,4iU triazol-l-ylmethyl)silane 80 bis(l,1'-Blphenyl-4-yl)(methyl)(1H1.2.4- triazol-l-ylmethyl)silane 90 [bis(4-Methoxyphenyl)]methyl(lH-l,2,4triazol-l-ylmethyl)silane 80 2-Chloropheny1(methyl)phenyl(lH-l,2,4trlazol-l-ylmethyl)silane 90 4-Bromophenyl(methyl)phenyl(1H-1,2,4triazol-l-ylmethyDsilane 90 [bis(2-Chlorophenyl)]methyl(1H-1,2,420 triazol-l-ylmethyl)silane 60 (1,1'-Biphenyl-4-yl)dimethyl(lH-l,2,4triazol-l-y lmethyDsilane, 1:1 complex with cuprous chloride 90 (1,1'-Bipheny1-4-y1)dimethyl(1H-1,2,425 triazol-l-ylmethyl)sllane, 1:1 complex with zinc (II) chloride 90 2-Chlorophenyl(4-chlorophenyl)methyl(1H-1,2,4-triazol-l-y lmethyDsilane 70 [bis(2-Fluorophenyl)]methyl(lH1.2.4- triazol-l-ylmethyl)silane, 3 1:1 complex with cuprous chloride 90 (ΙΗ-Imidazol-l-ylmethyl)dimethy1(4-phenoxyphenyl)silane 70 bis(4-Fluorophenyl)(lH-imidazol-1ylmethyDmethylsilane 90 155 Table 9 (continued) X Control of Compound Rice Sheath Blight 3 378 (lH-Imidazol-l-ylmethyl)dimethyl(2-trifluoromethylphenyl)sllane 80 Butyl(2,4-dichlorophenyl)(lH-imidazol-l-ylmethyl)methylsilane 90 bis(2,4-Dichlorophenyl)(IH-imidazoll-ylmethyl)methylsilane 80 (4-Fluorophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 90 (ΙΗ-Imidazol-l-ylmethyl)(2-methoxyphenyl) dimethy lsilane 90 [4-(4-Chlorophenoxy)phenyl]dimethyl(lH-imidazol-l-y ImethyDsilane 70 Buty1(ΙΗ-imidazol-l-ylmethy1)methyl(phenyl)silane 80 (1,1'-Biphenyl-4-yl)butyl(lH-imidazol-l-ylmethyl)methylsilane 90 Butyl(4-fluorophenyl)(lH-imidazoll-ylmethyl)methylsilane 80 (1,11 -Biphenyl-2-y DdimethyHlHimidazol-l-ylmethyl)silane 90 (l,l'-8iphenyl-3-yl)dimethyl(lHimidazol-l-ylmethyl)silane 90 [bis (2-Chlorophenyl)](lH-imidazoll-ylmethyl)methylsilane 40 (1,1'-Bipheny1-4-yl)dimethy1(1Himidazol-l-ylmethyDsllane, 1:1 complex with cuprous chloride 50 (2-Chlorophenyl)(dimethyl)(lH-lmidazol-l-y ImethyDsilane 90 INSERT V 156 Example 77 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). These suspensions were sprayed to the point of run-off on rice seedlings. The following day, the plants were inoculated with a spore suspension of Pyrlcularla oryzae, causal agent of rice blast, and incubated in a saturated humidity chamber at 28°C for 24 hours and then in a growth room for an additional 7 days, when disease ratings were made. Percent disease control is shown in the following table. Treated plants had no or few lesions while the untreated plants had numerous lesions on each leaf.

Table 10 Compound % Control of Rice Blast Dimethy1(1-naphthalenyl)(1H-1,2,4triazol-l-ylmethyl)silane 70 bis(4-Chlorophenyl)(methyl)(1H25 l,2,4-triazol-l-ylmethyl)silane 90 bis(4-Fluorophenyl)(methyl)(lH1.2.4- triazol-l-ylmethyl)silane 100 [4-(1,1-Dlmethylethyl)pheny1]dimethy1(1H-1,2,4-triazol-l-y130 methyDsilane 90 (4-ChlorophenyDmethyl(pheny1)(1H1.2.4- triazol-l-ylmethyl) silane 100 Buty1(methy1)phenyl(1H-1,2,4-triazoll-ylmethyl)silane 90 35 (2-Chloropheny Ddimethy XlH-l, 2,4triazol-l-ylmethyl)silane 100 157 Table 10 (continued) % Control of Rice Blast Compound (l,l'-Biphenyl-4-yl)butyl(methyl)(1H-1,2,4-triazol-l-ylmethylJsilane 100 Butyl(4-fluorophenyl)methyl(lH-l,2,4triazol-l-ylmethyl)silane 100 Dibutyl(methyl)(lH-l,2,4-triazol-lylmethyDsilane 80 bis(l,l’-Biphenyl-4-yl)(methyl)(lH1.2.4- triazol-l-ylmethyDsilane 100 (1,l'-Biphenyl-2-yl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane 90 2-Chlorophenyl(methyl)phenyl(lH-l,2,4triazol-l-ylmethyl)silane 100 4-Bromophenyl(methyl)phenyl(1H-1,2,4triazol-l-ylmethyl)silane 80 [bis(2-Chlorophenyl)]methyl(lH-l,2,4triazol-l-ylmethyl)silane 90 Dimethyl(4-methylsulfonylphenyl)(1H1.2.4- triazol-l-ylmethyl)silane 70 [bis(4-Bromophenyl)lmethy1(1H-1,2,4triazol-l-ylmethyl)silane 90 (1,1'-Bipheny1-4-yDdimethyl(1H-1,2,4tr iazo1-1-ylmethy Ϊ)silane, 4-dodecy1benzenesulfonic acid salt 80 (1,1'-Bipheny1-4-y1)dimethy1(1H-1,2,4triazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 (1,l'-Biphenyl-4-yDdimethyl(1H-1,2,4triazol-l-ylmethyDsilane, 1:1 complex with zinc (II) chloride 100 [bis(2-Fluorophenyl)]methyl(lH1,2,4-triazol-l-yimethyDsilane, 1:1 complex with cuprous chloride S3378 158 Table 10 (continued) % Control of Compound Rice Blast [bis(2-Fluorophenyl)]methy1(1H1,2,4-triazol-l-ylmethyl)silane, 2:1 complex with cupric chloride 100 (ΙΗ-Imidazol-l-ylmethyl)dimethy1(4-phenoxyphenyl)silane 70 10 [4-(l,l-0imethylethyl)phenyl](lHlmidazol-l-ylmethyDdimethylsilane 80 (4-Fluorophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 100 [4-(4-Chlorophenoxy)phenyl]dimethyl15 (ΙΗ-imidazol-l-y ImethyDsilane 100 Buty1(ΙΗ-imidazol-l-ylmethy1)methyl(phenyl)silane 90 (l,l'-Biphenyl-4-yl)butyl(lH-imidazol-l-ylmethyl)methylsilane 90 20 Butyl(4-fluorophenyl)(lH-imidazoll-ylmethyl)methylsilane 100 (1,1’-Bipheny1-2-yl)dimethyl(1Himidazol-l-ylmethyl)sllane 90 (1,1'-Bipheny1-3-y1)dimethy1(1H25 imidazol-l-ylmethyl)silane 80 [bis(2-Chloropheny1)](lH-imidazoll-ylmethyl)methylsilane 90 Dimethyl(ΙΗ-imidazol-l-ylmethy1)(4-methylsulfonylphenyl)silane 100 30 [bis(4-Bromophenyl)](lH-imidazol-lylmethyDmethylsilane 80 INSERT W 159 Example 78 Compounds of this invention were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). These suspensions were sprayed to the point of run-off on tomato seedlings. The following day, the plants were inoculated with a spore suspension of Phytophthora infestans, causal agent of tomato late blight, and incubated in a saturated humidity chamber at 20°C for 24 hours and then in a growth room for an additional 7 days, when disease ratings were made. Percent disease control is shown in the following table. Treated plants had no or few lesions while the untreated plants had numerous lesions on each leaf.

Table 11 % Control of Compound Tomato Late Blight Dimethy1(4-phenoxyphenyl)(1H-1,2,4triazol-l-ylmethyl)silane 50 [4-(4-Chlorophenoxy)phenyl]dimethyl(1H-1,2,4-triazol-l-ylmethy1)silane 50 (1,1'-Biphenyl-2-yDdimethyl(1H-1,2,4triazol-l-ylmethyl)silane 50 (l,l'-Biphenyl-4-yl)d imethy1(1H-1,2,4triazol-l-ylmethyl)silane, 4-dodecylbenzenesulfonlc acid salt 60 (1,1'-Bipheny1-4-y1)dimethy1(1H-1,2,4triazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 (1,1'-Bipheny1-4-y1)dimethy1(1H-1,2,4 triazol-l-ylmethyl)silane, 1:1 complex with zinc (IX) chloride 160 Table 11 (continued) % Control of Tomato Late Blight Compound [bis(2-Fluorophenyl)]methyl(lH1,2,4-triazol-l-ylmethyl)silane, 2:1 complex with cupric chloride 40 (4-Bromophenyl)(lH-imidazol-l-ylmethyl)dimethylsilane 30 10 (1,1'-Bipheny1-4-y1)dimethy1(1Himidazol-l-ylmethyl)silane 50 (lH-Imidazol-l-ylmethyl)dimethyl(4-phenoxyphenyl)silane 80 15 Oimethyl(lH-imidazol-l-ylmethyl)- (3-trlfluoromethylphenyl)silane 70 (2,6-Dimethoxypheny1)(dimethyl)(1Himidazol-l-y ImethyDsilane 50 [bis (2-Chlorophenyl)](lH-imidazol1-y lmethy Dmethy lsilane 60 20 INSERT X S3378 161 Example 79 Compounds of this invention were incorporated into 45°C standard strength V-8 agar at a concentration of 200.0 ppm. The amended media were then dispensed into petri dishes and allowed to solidify.

Plugs approximately 4 mm from agar cultures of 5 Phytophthora species: Phytophthora clnnamomi, P. cactorum, P. infestans, P. palmivora, and P. parasitica var. nicotianae were placed on the media and incubated at 22°C for 6 days. Colonies whose radial growth extended 1 mm or less were considered to be controlled by a compound when compared to colonies whose radial growth extended 15 mm or more when growing on unamended media. The number of Phytophthora species controlled by certain compounds of this invention are listed in the table below.

Table 12 ί of 5 Phytophthora species Compound _controlled in vitro (Butyl)dimethyKlH-1,2,4-triazol-1ylmethyUsilane 1 (3,4-Dichlorophenyl)dimethyl(1H1,2,4-triazol-l-ylmethyl)silane 2 (l,l'-Biphenyl-4-yl)dimethyl(lHimidazol-l-ylmethyl)silane 3 (lH-Imidazol-1-ylmethyl)dimethy1(4-phenoxyphenyl)silane 4 (2,4-Dichlorophenyl)dimethyl(lHimidazol-l-ylmethyl)silane 5 Diphenyl(lH-imidazol-l-ylmethyl)methylsilane 2 (4-Fluorophenyl)(lH-imidazol-l-ylmethyl)methyl(phenyl)silane 2 3 37*; 162 Example 80 Compounds of this Invention were Incorporated Into a proprietary formulation and used to coat cotton seeds at a rate of 2 gm/kg seed. After being thor5 oughiy coated, the seeds were allowed to air dry at room temperature. The cotton seeds were then planted into soil amended with the fungus Pythlum aphanadermatum, sand, and corn meal at a rate sufficient to kill most untreated seeds. The seeds were held at room temperature for 1 week, after which time disease ratings were made. Percent disease control is shown in the following table. Most or all seeds from treatments germinated and produced vigorous seedlings in contrast to untreated seeds which either did not germinate or produced damped off or weak seedlings.

Table 13 % Control of Compound Pythlum on Cotton Ethyldimethyl(lH-l,2,4-triazol-ly ImethyDsilane 48 (l,l,-Biphenyl-4-yl)dimethyl(lH1,2,4-triazol-l-ylmethyl)silane 12 (4-Chlorophenyl)dimethyl(lH-l,2,4triazol-l-ylmethyl)silane 53A Dimethyl(4-phenoxypheny1)(1H-1,2,4triazol-l-ylmethyDsilane 18A (1,1'-Bipheny1-4-yl) dimethyl(1Himidazol-l-y ImethyDsilane 18 (4-Chlorophenyl)(lH-imidazol-1ylmethyDdimethylsilane 18A (3,4-Oichlorophenyl)(lH-imidazoll-ylmethyl)dimethylsilane 15A a control at a rate of 0.5 gm/kg seed. 163 Example 81 Compounds of this Invention were incorporated into a proprietary formulation and used to coat corn seeds at a rate of 2 gm/kg seed. After being thor5 oughly coated, the seeds were allowed to air dry at room temperature. The seeds were then planted into soil amended with a mixture of the fungus Pythlum aphanadermatum. sand, and corn meal at a rate sufficient to kill most untreated seeds. The seeds were held at 49°F for 2 weeks and then at 70°F for 1 additional week. After this time disease ratings were made. Percent disease control is shown in the following table. Most or all seeds from treatments germinated and produced vigorous seedlings in contrast to untreated seeds which either did not germinate or produced damped off or weak seedlings.

Table 14 X Control of Compound Pythlum on Corn Ethyldimethyl(lH-l,2,4-triazol-lylmethyUsllane 13 -- (1,l’-Bipheny1-4-yl)dimethyl(lHl,2,4-triazol-l-ylmethyl)silane 30 (4-Chlorophenyl)dimethyKlH-1,2,4triazol-l-ylmethyl)silane 8 Dimethyl(l-naphthalenyl)(lH-l,2,4triazol-l-ylmethyl)silane 30 (3,4-0iohlorophenyl)dimethyl(lHl,2,4-triazol-l-ylmethyl)silane 43 EthyKlH-imidazol-l-ylmethy1)dimethylsilane 70 ,5 (ΙΗ-Imidazol-l-ylmethyl)dimethy13 (4-methylphenyl)silane 164 Table 14 (continued) % Control of Compound Pythlum on Corn (1,11-Biphenyl-4-yl)dimethyl(lHimidazol-l-ylmethyl)silane 32 (4-Chlorophenyl)(lH-imldazol-1ylmethyDdlmethylsilane 25 (lH-Imidazol-l-ylmethyDdimethy1(1-naphthalenyl)silane 27 (3,4-Dichlorophenyl)(lH-imidazol1-ylmethyl)dimethylsilane 30 (ΙΗ-Imidazol-l-ylmethyDdimethyl(4-phenoxyphenyl)silane 5 01methyl(4-fluorophenyl)(lH-imidazol-l-ylmethyl)silane 15

Claims (7)

1. CIAIMS

1. A compound of the formula: wherein and Q 2 are independently H or CH3; R 1 i s c 2 -c 18 alkyl, C^-Cg cycloalkyl, naphthyl, or where R4 and R5 are independently -H; halogen; -0CH3; -OCF3; -SCH3; -SO2CH3; phenyl; phenyl substituted with halogen and/or 0^-04 alkyl and/or -CF3; phenoxy, phenoxy substituted with halogen and/or 0^-04 alkyl and/or -CF3;CF 3 ; C1-C4 alkyl; or cyclohexyl; R 2 and R 3 are independently C 3 -Cg alkyl, C3-C6 cycloalkyl and ORg, or R where Rg is 0^-04 alkyl, or one Rg group may be H and/or one Rg group may be -166-Si-R, « I and Rj and R3 bridge or a optionally be R^q that have together may be a 1,2- or 1,3- or 1,4-glycol 1,4 unsaturated glycol bridge which may substituted by up to four alkyl groups R7a total of up to four carbon atoms, or R_-R 7 10 or R 7- R 10 or and salts thereof with protic acids and complexes with metal ions. A compound of the formula: 2. wherein Ql, Qj and Qg are independently H or CH3; R'l is Cg-Cjg alkyl, Cg-Cg cycloalkyl, naphthyl or -167where R'4 and R's are independently halogen; -OCH3; -OCF3;SCH3; -SO2 c H3J phenyl; phenyl substituted with halogen and/or C1-C4 alkyl and/or -CF3; phenoxy; phenoxy substituted with halogen and/or C1-C4 alkyl and/or -CF3;CF3-;Cq-C4 alkyl; or cyclohexyl; or one of R'4 and R's may additionally be B; and R2 and R3 are independently C^-Cg alkyl, C3~Cg cycloalkyl, ORg, or where R4, R5 and Rg are as defined in Claim 1, and R2 and R3 together may be a 1,2- or 1,3- or 1,4-glycol bridge or a 15 1,4 unsaturated glycol bridge which may optionally be substituted by up to four alkyl groups R7-R10 that have a total of up to four carbon atoms, viz. or or R 7~ R l0 and salts thereof with protic acids and complexes with metal ions. -1683. A compound of claim 1 or 2 wherein Oj and Q 2 are H. 4. A compound of claim 3 wherein R^ or R'j is 5 R2 is C1-C4 alkyl or and R3 is Cj-C^ alkyl. 5. A compound of claim 4 wherein Rj and R'j are ” i_ »5 where 3 R4 and R'4 are H, F, Cl, Br or phenyl; R5 is H, F, Cl or Br; R'g is F, Cl or Br or may be H if R'4 is not H; and R 2 is -169ρ or Cj-C4 alkyl; and 5 R3 is C1-C4 alkyl. 6. The compound of Claim 1 which is (1,1'-bi-phenyl5 4-yl) dimethyl(1H-1,2,4-triazol-l-ylmethyl) silane. 7- The compound of Claim 1 which is bis(4chlorophenyl)methyl{1H-1,2,4-triazol-l-ylmethyl) silane. 8. The compound of Claim 1 which is Ebis(4fluorophenyl)]methyl(lH-l,2,4-triazol-l-ylmethyl)silane. lO 9. The compound of Claim 1 which is 4fluorophenyl(methyl)phenyl(lH-l,2,4-triazol-lylmethyl)silane. 10. The compound of claim 2 which is (2,4dichlorophenyl) dimethyl(ΙΗ-imidazol-l-ylmethyl) silane. 15 11. A compound of claim 1 wherein: and Q 2 are H; R3 is C 2 -Cjg alkyl, C3-C6 cycloalkyl, naphthyl, or where 4 R 4 and Rg are independently -H, halogen, phenyl,20 OCH3, -SCH 3 , phenoxy, -CF3 or Cy-C4 alkyl; -170and R 2 and R 3 are independently Cj-Cg alkyl, C 3 -Cg cycloalkyl, or ORg, where Rg is H or C1-C4 alkyl. 12. A compound of claim 2 wherein 5 Qi, 0 2 and Q 3 are H; R'l is R 2 and R 3 are independently C1-C4 alkyl or ORg, where Rg is H or C1-C4 alkyl. 10 13. A composition for controlling fungus diseases comprising an effective amount of a fungicidal compound and at least one of the following: surfactant, solid or liquid inert diluent, characterised in that said fungicidal compound comprises a compound of any of claims 15 1 to 12. 14. A method for controlling fungus diseases by applying to the locus to be protected an effective amount of a fungicidal compound, characterised in that said fungicidal compound comprises a compound of any of claims 20 1 to 12. 15. A process for preparing a compound of claim 1 or 2 which comprises reacting a silane derivative of formula -171RpSi-CH^ Si-CH-Y I 2 wherein Rl, R'i, R2 and R3 are as defined in claims 1 and 2 and Y is chlorine, bromine, iodine or arylsulfonyloxy, with a 1,2,4-triazole or imidazole of formula Qi Hd wherein Οχ and Q 2 are independently H or CH3 and X is N, CH or CCH3, or with an alkali metal salt thereof. 10 16. A process for preparing a compound of claims 1 or

2 wherein R2 and/or R3 is ORg which comprises reacting a corresponding compound of formula Rx - Si - CH 2 Y R'3 wherein R 2 i s halogen or R- 2 am R^ is halogen or at least one of R'2 and R'3 being halogen, and Y is as defined in claim 15, with a triazole or imidazole sodium salt of formula 52378 -172Q NaN wherein X is N, CH or CCH3, and reacting the intermediate so obtained with RgOH. 5 17. A process for preparing a compound of claim 1 which comprises reacting 1) an intermediate selected from the group R3 I I Cl3SiCH2Cl, CljSiCHjCl and Cl-Si-CHjCl in a suitable solvent with R|M where M is Na, Li or MgX lO where X is Br, Cl, I, at a temperature of from -80° to 40°C to form a chloromethylsilane; and 2) reacting the chloromethylsilane with 1,2,4-triazole, its 3-methyl or

3. ,5-dimethyl derivative, or their alkali, metal salts in polar aprotic solvents, ethers or ketones at 0° to 200°C. 15 18. A process for preparing a compound of Claim 1 which comprises 1) reacting ¢1 R2 I Rl-SiCHjCl or Rj-Si-CHjCl Cl Cl -173with RgOH in a suitable solvent with a suitable base at a temperature of 0°-100Oc to form an alkoxy or dialkoxy ch1oromethy1si 1 ane ; and 2) reacting the chloromethylsilanes with 1,2,

4. -triazole, its 3-methyl or

5. 3,5-dimethyl derivative, or their alkali metal salts in polar aprotic solvents, ethers or ketones at 0® to 200°C. 19. A process for preparing a compound of claim 2 which comprises reacting 1) an intermediate selected from the group R 3 r 2 I I

6. 10 Cl 3 SiCH 2 Cl, Cl 2 SiCH 2 Cl and Cl-Si-CH 2 C1 I *3 in a suitable solvent with R'iM where M is Na, Li or MgX where X is Br, Cl, I, at a temperature of from -80° to 40°C to form a chloromethylsilane; and 2) reacting the chloromethyl silane with imidazole, its 2-methyl, 2,415 dimethyl, 4,5-dimethyl, and 2,4,5-trimethyl derivatives, or their alkali metal salts in polar aprotic solvents, ethers or ketones at 0° to 200°c. 20. A process for preparing a compound of claim 2 which comprises 1) reacting , I 1 Rj-SiCHjCl Cl and r 2 I R'l-Si-CH 2 C1 L, -174with RgOH in a suitable solvent with a suitable base at a temperature of 0° to 100°C to form an alkoxy or dialkoxy chloromethylsilane; and 2) reacting the chloromethylsilane with imidazole, its 2-methyl, 2,4-methyl, 4,5-methyl, and 5 2,4,5-trimethyl derivatives, or their alkali metal salts in polar aprotic solvents, ethers or ketones at 0° to 200°C. 21. A compound substantially as hereinbefore described with reference to the examples. 10 22. A composition substantially as hereinbefore described with reference to the examples. 23. A method substantially as hereinbefore described with reference to the examples. 24. A process substantially as hereinbefore described

7. 15 with reference to the examples.