FUNGICIDAL 1,2,4-TRIAZOLE AND IMIDAZOLE DERIVATIVES

Abstract: 1,2,4-Triazole and imidazole derivatives of the general for­ mula wherein R₁, R₂ and R₃ are alkyl, naphthyl or optionally sub­ stituted phenyl; or R₂ and R₃ may be hydroxy or alkoxy; X is N, CH or CCH₃; and Q₁ and Q₂ are H or CH₃; are effective fungicides for controlling fungi in a plant locus. They may be formulated for use in conventional manner. The compounds may be made e.g. by reacting a suitable chloromethylsilane with a suitable imidazole or 1,2,4-triazole.

Description: Title FUNGICIDAL 1,2,4-TRIAZOLE AND IMIDAZOLE DERIVATIVES Background of the Invention The present invention relates to silylmethyltriazoles and imidazoles such as, for example, di methyl(phenyl) (lH-l,2,4-triazol-l-ylmethyl)silane and (l,l'-biphenyl-4-yl)dimethyl(lH-imidazol-l-ylmethyl)- 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: EMI1.1 wherein R1, R2 and R3 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: EMI1.2 wherein R can be C1-C4 alkyl and Y and Z can be H or SiRlR2R3, wherein R1, R2, and R3 can be alkyl, haloalkyl, alkyl, alkynyl, or substituted phenyl. It is taught that the compounds are useful as agricultural fungicides. U.S. Patents 3,256,308 and 3,337,598 disclose compounds of the formula: EMI2.1 wherein Rl 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: EMI2.2 and their use as fungicides. Research Disclosure 17,652 discloses silyl ethers of the formula: EMI2.3 wherein Ar can be substituted phenyl, X can be CH or N, and R can be alkyl. It is taught that the compounds are useful as agricultural fungicides. West German Patent DE 3,000,140 discloses silyl ethers of the formula: EMI2.4 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 organosilicon compounds having in a molecule at least one monovalent guanidine group represented by the general formula: EMI3.1 in which R is a hydrocarbon atom or a monovalent hydrocarbon group. These guanidine-containing organosilicon compounds are described as useful as antifungai agents for molded plastics and rubbers, particularly silicone rubbers. U.S.S.R. Patent 346,306 discloses silylmethylazoles of the formula: (Rl)n(R20)3-nsicH2Az wherein R1 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(R2O)3-nSiCH2CH2Az wherein R1, R2, n, and Az are as described in the previous reference. Summary of the Invention This invention relates to silylmethyltriazoles of Formula I and to silylmethylimidazoles of Formula II and to agriculturally useful compositions of these compounds. EMI4.1 wherein and Q2 and Q3 are independently H or CH3 n is 1; 1 is. C2-C18 alkyl, C3-C6 cycloalkyl, naphthyl, or EMI4.2 R'1 is C6-C18 alkyl, C3-C6 cycloalkyl, naphthyl or EMI4.3 where R4 and R5 are independently -H; halogen; -OCH3; -OCF3; -SCH3; -S02CH3; 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; Cl-C4 alkyl; or cyclohexyl; with the proviso that for compounds of Formula II, both R4 and R5 may not simultaneously be H; and R2 and R3 are independently C1-C6 alkyl, C3-C6 cycloalkyl, OR6, or EMI5.1 where R4 and R5 are as defined above except that said proviso does not apply, and R6 is H or C1 -C4 alkyl, with the proviso that both R and C1-C4 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-R10 that have a total of up to four carbon atoms. EMI5.2 This invention also relates to a method for controlling fungus diseases, particularly fungus diseases of living plants which comprises applying to the locus to be protected an effective amount of a compound of formula I or formula II EMI5.3 wherein Q1, Q2 and Q3 are independently H or CH3; n is 1; R1 and R'1 are C2-C18 alkyl, C3-C6 cycloalkyl, naphthyl, or EMI6.1 where R4 and R5 are independently -H; halogen;. -OCH3; -OCF3; -SCH3; -S02CH3; phenyl; phenyl substituted with halogen and/or C1-C4 alkyl and/or -CF3; phenoxy; phenoxy substituted with halogen and/or Cl-C4 alkyl and/or -CF3; -CF3; C1-C4 alkyl; or cyclohexyl; R2 and R3 are independently C1-C6 alkyl, C3-C6 cycloalkyl, OR6, or EMI6.2 where R6 is H or C1-C4 alkyl, with the proviso that both R2 and R3 may not be OH; and R2 and R-3 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-R10 that have a total of up to four carbon atoms. EMI6.3 When R2 or R3 is OH, Formula I and Formula II are understood to include the disiloxane: EMI7.1 This invention also relates to salts of compounds of Formula I and Formula II with protic acids and complexes with metal ions. Preferred for their high activity and/or favorable ease of synthesis are compounds of the generic scope wherein Q1 = Q2 = H. More preferred for their higher activity and/or more favorable ease of synthesis are compounds of the preferred scope wherein R1 and R1' are EMI8.1 R2 is C1-C4 alkyl or EMI8.2 R3 is C1-C4 alkyl. Most preferred for their highest activity and/or most favorable ease of synthesis are compounds of the more preferred scope wherein R1 and R1 are EMI8.3 where R4 is at the para position of R1 or R'l, and R4 is H, F, C1, Br, or phenyl, and R5 is H, F, Cl or Br; and R2 is EMI8.4 or C1-C4 alkyl; and R3 is C1-C4 alkyl. Specifically preferred for their excellent activity and/or most favorable ease of synthesis are the following compounds of Formula I: (Dimethyl)phenyl(lH-1,2,4-triazol-1-ylmethyl)silane; Dimethyl(4-methylphenyl)(1H-1,2,4-triazol-1-ylmethyl) silane; (4-8romophenyl)dimethyl(lH-1,2,4-triazol-l ylmethyl)- silane; (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4-triazol-1-yl methyl)silane; (4-Chlorophenyl)dimethyl(1H-1,2,4-triazol-1-yl methyl)silane; (2,4-Dichlorophenyl)dimethyl(lH-1,2,4-triazol-1-yl- methyl)silane; 8utyl(4-chlorophenyl)methyl(lH-1,2,4-triazol-1-yl- methyl)silane; bis(4-Chlorophenyl)methyl(lH-1,2,4-triazol-1-yl- methyl)silane; Methyl(diphenyl)(lH-1,2,4-triazol-1-ylmethyl)silane; ; [bis(4-Fluorophenyl)]methyl(1H-1,2,4-triazol-1-yl methyl)silane; (4-Fluorophenyl)dimethyl(lH-1,2,4-triazol-1-ylmethyl)- silane; Butyl(2,4-dichlorophenyl)methyl(lH-1,2,4-triazol-1-yl methyl)silane; [bis(2,4-Dichlorophenyl)]methyl[1H-1,2,4-triazol-1-yl methyl)silane; 2,4,Dichlorophenyl(methyl)phenyl(lH-1,2,4-triazol-1-yl- methyl)silane; 4-Chlorophenyl(methyl)phenyl(lH-1,2,4-triazol-1-yl- methyl)silane; 4-Fluorophenyl(methyl)phenyl(1H-1,2,4-triazol-1-yl methyl)silane; Butyl(methyl)phenyl(1H-1,2,4-triazol-1-ylmethyl)silane; Butyl(4-fluorophenyl)methyl(lH-1,2,4-triazol-1-yl- methyl)silane; [bis(1,1'-Biphenyl-4-yl)]methyl(1H-1,2,4-triazol-1-yl methyl)silane; (l,l'-aiphenyl-4-yl)butyl(methyl)(lH-1,2,4-triazol-1- ylmethyl)silane; and (l,l'-aiphenyl-4-yl)methyl(phenyl)(lH-1,2,4-triazol-1- ylmethyl) silane. Especially preferred compounds, methods, and compositions of Formula II are those compounds wherein at least one group R1, R2 or R3 is other than lower alkyl (C1-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: : Cl,l'-8iphenyl-4-yl)dimethyl(lH-imidazl-l-ylmethy1)- silane; (2,4-Dichlorophenyl)dimeth;l(lH-imidazol-l-ylmethyl)- silane; Butyl(2,4-dichlorophenyl)(lH-imidazol-l-ylmethyl) methylsilane; Ebis(4-Fluorophenyl)](lH-imidazol-l-ylmethyl)methyl- -silane; ±bis(2, 4-Dichlorophenyl) ](lH-imidazol-1-ylmethyl)- methylsilane; (2,4-Oichlorophenyl)(lH-imidazol-l-ylmethyl)methyl- (phenyl) silane; (4-Chlorophenyl)(lH-imidazol-l-ylmethyl)me-thyl(phenyl)- silane; (4-Fluorophenyl)(1H-imidazol-l-ylmethyl)methyl(phenyl)- silane; (1,1'-8iphenyl-4-yl)butyl(lH-imidazol-l-ylmethyl)- methylsilane; (l,l'-Biphenyl-4-yl)(lH-imidazol-l-ylmethyl)methyl (phenyl) silane; ; Dbis(1,1-8iphenyl-4-yl)](lH-imidazol-l-ylmethyl)methyl- silane; Butyl(4-chlorophenyl)(lH-imidazol-l-ylmethyl)methyl silane; (4-Chlorophenyl) dimethyl( lH-imidazol-l-ylmethyl) - silane; Dimethyl(4-fluorophenyl)(lH-imidazol-l-ylmethyl) silane; and Butyl(4-fluorophenyl)(lH-imidazol-l-ylmethyl)methyl silane. When Q1 and Q2 are both H or both CH3, the process for preparing the triazole derivatives of Formula I will ordinarily produce a mixture of two triazole isomers: EMI11.1 Formula IA Formula IB Three isomers are possible when one triazole substituent is H and the other is CH3: EMI11.2 Formula IC Formula ID EMI11.3 Formula IE The mixture will contain predominately the isomers of Formula IA or Formula IC; however, the isomers of For mulae IB, ID, 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 Q2 and Q3 are not the same: EMI12.1 Formula. IlA Formula IIB The isomers of Formula IIA will generally predominate; however, the isomer of Formula II8 also has fungitoxic activity and separ-ation of the isomers is not required. Detailed Description of the Invention In the following discussion, R1 is understood to represent both R1 and R1', since all values of R1' are included in the definition of R1. Further, the term "azole" will be used to refer to appropriately substituted 1,2,4-triazoles and imidazoles EMI12.2 where Qly Q2 and Q3 may be H or CH3. In drawing structural formulas, the part-structure EMI12.3 where X is N or 003 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 imidazole sodium salt or their methylated homologs: EMI13.1 Lithium and potassium azole salts may also be used. Bromomethylsilanes, iodomethylsilanes, or arylsulfonyloxymethylsilanes may be used instead of chloromethylsilanes. Roughly equimolar amounts of the reagents are used (except when R3 OR6; see below), with the azole salt often taken in 3-10% excess of theory. In addition, 1,2,4-triazole or imidazole themselves can be used if an acid acceptor is added. Suitable acceptors include excess azole, alkali metal alkoxides such as sddium 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 Oa and 2000C, preferably between 250 and 1000C. The reaction can be conducted under elevated pressure, but it is generally preferable to operate at atmospheric pressure. The optimum temperature and reaction time will vary with the concentra tion and choice of reagents, and especially 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 approximately 2 hours at 80-900C, 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 rap-id. 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 SiCH2Cl singlet near 2.9 and the product SiCH2N 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-1,2,4-triazol-4-ylmethyl compound: EMI14.1 The ratio of isomers varies with values of R and reaction conditions, with a l-substituted to 4-ubstituted ratio of roughly 10:1 often observed. The mono- and dimethyltriazoles give similar 4H-isomers as minor products: EMI14.2 When the unsubstituted silylmethyltriazole is available, metalation-methylation provides an alternate synthesis of the methylated homologs: EMI15.1 With respect to the imidazole derivatives or Formula II, isomers are possible only when Q2 and Q3 are not the same. Two isomers result: EMI15.2 Formula IIA Formula IIB The product of Formula IIA will generally predominate. If desired, the isomers may be separated by standard techniques such as crystallization, distillation, or chromatography. For the case where R3 = OR6 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: EMI16.1 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 R6 = C1-C4 alkyl. For R6 = H, however, hydrolysis-is best conducted near room temperature to minimize disiloxane formation, recognizing that silanol-disiloxane equilibrium is possible whenever R6 = H: EMI16.2 The position of equilibrium and the rate at which it is established will vary with the values of R1 and R2, solvent, temperature, and the presence or absence of acidic er basic catalysts. In the second method, the silicon-oxygen bond is formed first, followed by azole displacement as described earlier: EMI17.1 Reaction of the chlorosilane with R6OH 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 03 to 100cm, and R6OH is often taken in excess of theory. The combination of 2 equivalents of R6OH, 1.1 equivalents of triethylamine, and 0.1 equivalents of imidazole in dimethylformamide at 800 for two hours has been broadly applicable. Extending these methods to (chloromethyl)dichlorosilanes provides dioxygenated silanes: EMI17.2 Glycol derivatives are formed similarly, using a diol instead of two molecules of R6OH. An alternative synthesis for alkoxy(chloromethyl)silanes involves selective replacement of one alkoxy group of a dialkoxysilane with an organometallic reagent: EMI18.1 Conditions for this displacement are as described in the next paragraph, with the added stipulation that the organometallic should be added to the dialkoxysilane. The required chloromethylsilane starting materials are made from commercially available chloro (chloromethyl)dimethylsilane, chloromethyl(dichloro)methylsilane, or chloromethyltrichlorosilane: EMI18.2 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-C1 bond intact. For the silanes containing two or three Si-Cl bonds, stepwise replacements are possible, giving considerable flexibility to the values of R1-R3. Bromosilanes, iodosilanes, or alkoxysilanes may be substituted for chlorosilanes in these reactions. Preferred solvents for these reactions include ethers such as tetrahydro furan, 1,2-dimethoxyethane, and diethyl ether, or hydrocarbons such as hexane and toluene. The preferred temperature will vary between -80 and 400 depending on the nature of the organometallic reagent, how it was generated, and the solvent. For example, when arylltthium 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 250 without competing reaction of the CH2C1 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 J. C. Jeffrey, J. Chem. Soc., 1954, 4266; and a recent review on synthesis of aryltrimethylsilanes from ClSi(CH3)3, which contains experimental procedures useful for ClSi(CH3)2CH2Cl reactions, is that of D. Habich and F. Effenberger, Synthesis, 1979, 841. Selective introduction of one new alkyl group into Cl2Si(CH3)CH2Cl is described by V. P. Kuznetsova and R. M. Sokolovaskaya, Zh. Obshch. Khim., 1969, 1977; Chem. Abstr., 72, 31897 p; and one aryl group may be introduced selectively as well: EMI19.1 In both cases the organometallic reagent should be added to the dichlorosilane at low temperature with good mixing for best yields. Reactions of C13SiCH2Cl with Grignard reagents are described by A. A. Zhdanov, V. I. Pakhomov, and T. Bazhanova, Zh. Obshch. Khim., 1973, 1280; Chem. Abstr., 79, 66452 m. Adding organometallic reagents to the trichlorosjlane is recommended even when three identical groups are being introduced, because adding C13SiCH2Cl to an organometallic reagent is not usually successful. A single aryl group may also be introduced: EMI20.1 A useful modification of literature procedures, applicable when R1 or R'1 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 ClSi(CH3)2CH2Cl 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-Cl bond as it is formed: EMI20.2 This reaction works equally well for aryl-substituted chlorosilanes such as C1S(CH3)(C6H5)CH2C1, and it can be used to introduce two aryl groups into Cl2Si(CH3)CH2Cl. In a further extension, an aryl and an n-butyl group may be introduced in one step: EMI21.1 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 oentimeters (cm¯l). Hexanes refers to the mixture of isomers boiling 68-690, and ether refers to diethyl ether. Example 1 Preparation of (1,1'-Biphenyl-4-yl)(chloromethyl) dimethylsilane A solution of 9.9 g (0.042 mol) of 4-bromobiphenyl in 50 ml of dry tetrahydrofuran was cooled to -780 under nitrogen and stirred while 26.5 ml (0.042 mol) of 1.6 molar n-butyllithium in hexane was added dropwise over 15 iutes. A thick slurry formed, and 35 ml of tetrahydrofuran was added to facilitate stirring. 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 (100% crude) of the title compound.as a colorless solid, m.p. 30-400, suitable for further reaction. Trace impurities could be removed by sublimation at 30 /0.1 mm, leaving the title compound unsublimed in 83% recovery: m.p. 37-40 ; ir (NujolR) 1585, 1240, 1110, 830, 810, 750, 690 cm-1; nmr (CDC13) 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 l,4-dibromobenzene and 1.2 g (0.050 g-atom) af 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)dimethylsi- lane 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 cm 1; nmr (CDC13) 0.4 (H, s), 2.9 (2H, 5), 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-bromochlorobenzene 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 mi (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 (CDCl3) 0.4 (6H, s), 2.9 (2H, s), 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)dimethylsilane A solution of 17.0 g (0.075 mol) of 2,4-dichlorobromobenzene and 10.8 ml (11.8 g, 0.082 mol) of chloro(chloromethyl)dimethylsilane in 100 ml of dry tetrahydrofuran was chilled to -700 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 -700. The. resulting cloudy. reaction mixture was allowed to warm to room temperature, poured into 400 ml of hexanes, filtered, and evaporated to leave 20.5 of yellow liquid. Distillation gave 12.6 g (66%) of the title compound as a colorless liquid; bp 83 (0.02 mm); nD24 1.5522; ir (neat) 1565, 1455, 1360, 1255, 112d, 1100, 1040, 825 cm'l; nmr (CDCl3) 0.5 (6H, s), 3.1 (2H, s), 7.0-7.5 (3H, m). Example 5 Preparation of Chloromethyl(2, 6-dimethoxyphenyl)- dimethylsilane A solution of 25.0 g (0.181 mol) of 1,3-dimethoxybenzene 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 Soand 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 (CDCl3) 0.4 (6H, s), 3.1 (2H, s), 3.7 (6H, s), 6.3 (2H, d), 7.1 (1H, 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 chloride by C. Eaborn and J. C. Jeffrey, J. Chem. Soc., 1954, 4266. For compounds where R1 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 EMI27.1 X = R1 or R1' C2H5 bp 127-128 n-C4Hg bp 1720 n-C1225 nD23 1.4510 n-C18H37 nD22 1.4556 cyclopropyl cyclopentyl cyclohexyl. bp 120-1300 (10 mm) l-naphthyl bp 1120 (0.08 mm) 2-naphthyl phenyl bp 85-860 (3 mm) 4-fluorophenyl bp 59.600 (0.1 mm) 4-methoxyphenyl bp 800 (0.05 mm) 4-phenoxyphenyl bp 1220 (0.03 mm) 4-(4-chlorophenoxy)phenyl nD22 1.5773 4-(4-fluorophenoxy)phenyl 4-(4-trifluoromethylphenoxy)phenyl 4-(4-methylphenoxy)phenyl 4-thiomethylphenyl bp 92.930 (0.05 mm) 4-trifluoromethylphenyl nD23 1.4686 4-methylphenyl bp 96 (7 mm) 4-i-propylphenyl 4-t-butylphenyl n23 1.5056 v 0 4-methylsulfonylphenyl m.p. 64-68 21 4-cyclohexylphenyl nDl 1.5424 4-trifluoromethoxyphenyl bp 55-570 (0.15 mm) 4-(4-chlorophenyl)phenyl 4-(4-bromophenyl)phenyl Table I (continued) X = R1 or R1 4-(4-methylphenyl)phenyl 4-(4-trifluoromethylphenyl)phenyl 4-(4-fluorophenyl)phenyl 3-phenylphenyl nD20 1.5862 3-trifluoromethylphenyl bp 59-62 (0.3 mm) 3-chlorophenyl bp 73 (0.15 mm) 2-trifluoromethylphenyl nD23 1.4826 2-phenylphenyl nD20 1.5772 2-chlorophenyl bp 78-80 (0.3 mm) 2-methoxyphenyl nD21 1.5164 2,3-dimethylphenyl 22 2,3-dimethoxyphenyl . "0 1.5254 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 bp 98 (0.6 mm) 3-methyl-4-fluorophenyl 3,5-dichlorophenyl bp 94-95 (0.25 mm) Example 6 Preparation of (l,l'-Biphenyl-4-yl)butyl(chloromethyl)- methylsilane The title compound can be prepared by the procedure of Example 1 by substituting (butyl)chloro(chloro methyl) methylsilane for chloro( chloromethyl ) dimethyl- silane. Related compounds can be prepared by the procedures of Examples 1-5, using the appropriate organolithium or Grignard reagent and Cl(R2)Si(CH3)CH2Cl. The required chloromethylsilane starting materials are made from R2MgCl or R2Li and C12Si(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)methylsilane in 150 ml of dry tetrahydrofuran was chilled under nitrogen to -700 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 -600C. 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 22 (0.1 mm); nD 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 (CDC13): 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 df 14.4 g (0.075 mol) of 4-bromochlorobenzene and 9.5 ml (12.3 g, 0.075 mol) of chloromethyl(dichloro)methylsilane in 150 ml of tetrahydrofuran was cooled to -600 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 -550, 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 chloromethyl(dibutyl)methylsilane, bp 450C (0.05 mm), followed by 6.8 g (35%) of the title compound as a colorless liquid: bp 900C (0.05 mm); nD21 1.5246; ir (neat) 2925, 1580, 1380, 1260, 1090, 1015, 820, 740 cm 1; nmr (CDC13) 0.4 (3H, s), 0.6-1.5 (9H, m), 2.9 (2H, s), 7.0-7.4 (4H, q). Example 8 Preparation of Chloromethyl(2,4-dichlorophenyl)methyl (phenyl)silane A solution of 13.6 g (0.060 mol) of 2,4-dichlorobromobenzene and 12.3 g (0.060 mol) of chloro(chloro methyl)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 separated, the aqueous phase was washed with 50 ml of hexanes, and the combined organic ph-ases 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) 3080, 3060, 0 2960, 2930, 1570, 1540, 1460, 1430, 1365, 1260, 1120, 1100, 1040, 820, 745, 735, 705 cm'1; nmr (CDC13) 0.8 (3H, s), 3.4 (2H, s), 7.2-7.9 (8H, m). Example 9 Preparation of Chlormethyl(bis(4-chlorophenyl)]methylsilane A solution of 19.1 g (0.10 mol) of 4-chlorobromobenzene 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 -5g . 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 24 compound as a colorless liquid: nD24 1.5913; ir (neat) 3080, 3040, 3020, 2960, 2930, 1580, 1490, 1380, 1260, 1085, 1015, 805, 790, 775, 740 cm'1; nmr (CDC13) 0.7 (3H, s), 3.1 (2H, s), 7.2-7.7 (8H, m); analysis for C14H13C13Si (mw 315.70): Calculated: C, 53.26; H, 4.15; C1, 33.69. Found: C, 53.4; H,. 4.4; C1, 34.2. 53.5; 4.4; 34.1. Example 10 Preparation of (Chloromethyl)bis(4-fluorophenyl)methylsilane A solution of 35 g (0.20 mol) of 4-fluorobromobenzene in 300 ml of dry tetrahydrofuran was chilled to -600 under nitrogen and stirred while 126 ml (0.20 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 12.6 ml (16.4 g, 0.10 mol) of chloromethyl(dichloro)methylsilane was added dropwise at a rate that held the mixture below -500. 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. Oistillation gave 20.6 g (73%) of the title compound as a colorless liquid: bp 107-1270 (0.1 mm); 22 1.5481; n0 nmr (CDCl3): 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 chloromethyl(diethoxy)methylsilane instead of the dichlorosilane gave the title compound in 58% yield after distillation: bp 115-138 (0.2 mm); nD21 1.5464; nmr as above. Example 11 Preparation of Chloromethyl(2-chlorophenyl) (4-chloro- phenyl)methylsilane 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 tetrahydrofuran was chilled to -600 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 molar n-butyllithium solution at a rate that held the mixture below -55"0. 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); nD20 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 (ODd3) 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-Cl bonds of C12Si(CH3)CH2Cl, according to the procedures of Examples 6-11. Table II EMI35.1 X = R1, R1 R2 CH5 C2H5 i-C3H7 cyclohexyl n-C4H9 n-C4H9 bp 45 (0.05 mm) n-C10H21 cyclopropyl n-C18H37 3-methylbutyl cyclopropyl n-C6H13 cyclohexyl cyclohexyl 1-naphthyl t-C4H9 2-naphthyl n-CsHll phenyl n-C3H7 phenyl n-C4H9 bp 82-90 (0.1 mm) phenyl 1, 1-dimethylpropyl 4-phenylphenyl C2H5 4-bromophenyl i-C3H7 4-fluorophenyl n-C4H9 bp 90-92 (0.1 mm) 4-phenoxyphenyl t-C4H9 4-t-butylphenyl cyclopentyl 3-trifluoromethylphenyl s-C4H9 3-chlorophenyl n-C5H11 2-thiomethylphenyl cyclobutyl 2-phenylphenyl i-C4H9 2,4-dichlorophenyl n-C4H9 bp 109-112 (0.1 mm) 2,4-dichlorophenyl cyclopropyl 2,3-dimethylphenyl n-C3H7 2-methyl-5-fluorophenyl cyclopentyl 2,5-dimethoxyphenyl 4-methylpentyl Table II (continued) X = R1, Rf R2 2,6-dimethylphenyl l-methylbutyl 3,5-dichlorophenyl n-C4H9 3,5-dichlorophenyl cyclohexyl 3-methyl-4-chlorophenyl cyclopropyl phenyl phenyl bp 104-1100(0.2 mm) 4-fluorophenyl phenyl nD22 1.5624 4-chlorophenyl phenyl bp 140-148 (0.1 mm) 4-bromophenyl phenyl bp 145-1550(0.1 mm) 4-phenylphenyl phenyl bp 173-178 (0.1 mm) 4-t-butylphenyl phenyl 4-thiomethylphenyl phenyl 4-phenoxyphenyl phenyl 4-trifluoromethoxyphenyl phenyl 4-methylsulfony Iphenyl phenyl 4-cyclohexylphenyl phenyl 4-(4-fluorophenyl)phenyl phenyl 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 3,5-dichlorophenyl phenyl 2,5-diemthoxyphenyl phenyl 2, 6-dimethoxyphenyl phenyl 4-bromophenyl 4-bromophenyl bp 160-170 (0.1 mm) 4-phenylphenyl 4-phenylphenyl m. p. 115-117 4-methoxyphenyl 4-methoxyphenyl bp 166-1710(0.1 mm) 3-trifluoromethylphenyl 3-trifluoromethylphenyl 2-methoxyphenyl 2-methoxyphenyl 2-chlorophenyl 2-chlorophenyl bp 135-140 (0.1 mm) 2,4-dichlorophenyl 2,4-dichlorophenyl nD21 1.5956 3,5-dichlorophenyl 3, 5-dichlorophenyl Table II (continued) X=R1, Rj R2 2-chlorophenyl 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 l-naphthyl 2,6-dimethoxyphenyl 4-phenoxyphenyl 3, 4-dichlorophenyl Example 12 Preparation of (l-l'-Biphenyl-l-yl) (chloromethyl)- diethylsilane The title compound can be prepared by the procedure of Example 1, using chlorochloromethyldiethylsilane instead of chlorochloromethyldimethylsilane. Similar compounds can be prepared by applying the procedures of Examples 1-5 to the appropriate organolithium or Grignard reagent and Cl(R2)Si(R3)CH2Cl. The required chlorochloromethyldialkylsilanes are made from C13SiCH2Cl, using two equivalents of R2MgCl or R2Li when R2 = R3 (see, for example, A. A. Zhdanov, V. I. Pakhomov, and T. Bazhanova, Zh. Obshch. Khim., 1973, 1280), or using one equivalent of R2MgCl or R2Li followed by one equivalent of R3MgCl or R3Li when R2 is not equal to R3. 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. 112-1150C; 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 C13SiCH2Cl, according to the procedures of Examples 12-13. Table III EMI40.1 X = R1, R1' R2 R3 C2H5 C2H5 C2H5 i-C3H7 i-C3H7 i-C3H7 n-C4H9 n-C4H9 n-C4H9 n-C8H17 C2H5 Cyclopentyl n C14H29 cyclopropyl l-methylbutyl n-C18H37 n-C6H13 n-C6H13 cyclopropyl C2H5 s-C4H9 cyclohexyl n-C3H7 n-C3H7 1-naphthyl n-C4H9 n-C4H9 2-naphthyl n-C4H9 cyclobutyl phenyl cyclopropyl n-C6H13 4-phenylphenyl n-C4H9 n-C4H9 4-phenylphenyl n-C6H13 n-C6H13 4-phenylphenyl cyclohexyl cyclohexyl 4-chlorophenyl n-c4H9 n-c4H9 4-fluorophenyl n-C3H7 n-C3H7 4-phenoxyphenyl n-C4H9 cyclohexyl 4-(4-chlorophenoxy)phenyl n-C4H9 n-C4H9 4-t-butylphenyl s-C4H9 i-C4H9 3-methoxyphenyl C2H5 t-C4H9 3-trifluoromethylphenyl s-C4H9 s-C4H9 2-thiomethylphenyl i-C3H7 3-methylbutyl 2-phenylphenyl cyclohexyl cyclohexyl 2,4-dichlorophenyl n-C4H9 n-c4H9 2,6-dimethylphenyl t-C4H9 t-C4H 3,5-dichlorophenyl cyclopentyl cyclopentyl 3-methyl-4-chlorophenyl s-C4H9 s-C4H9 Table III (continued) X = R1, R1' R2 R3 C2H5 phenyl phenyl cyclohexyl phenyl phenyl n-C18H37 phenyl phenyl n-C4H9 4-ch loroph enyl 4-chlorophenyl n-C12H25 4-chlorophenyl 4-chlorophenyl l-naphthyl 4-fluorophenyl 4-fluorophenyl cyclopropyl phenyl 4-t-butylphenyl n-C4H9 phenyl 4-phenylphenyl t-C4H9 phenyl 2,4-dichlorophenyl n-C3H7 phenyl 3-trifluoromethylphenyl i-C4 H0 phenyl 3,5-dichlorophenyl cyclopentyl phenyl 2,6-dimethoxyphenyl n-C14H29 4-chlorophenyl 2-fluorophenyl n-C4 % 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-didhloropheny 1 2,4-dichlorophenyl 2-naphthy 1 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 l-naphthyl 4-bromophenyl 3-methylphenyl 4-phenoxyphenyl 3,5-dimethylphenyl 3,4-dichlorphenyl Example 14 Preparation of Chloro(chloromethyl)methyl(phenyl)silane 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 -700. 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); nD23 1.5337; ir (neat) 3080, 3060, 2980, 2930, 1590, 1430, 1260, 1120, 820, 79t, 740, 700 cm 1; nmr (CDC13) 0.8 (3H, s), 3.1 (2H, s), 7.3-7.6 (3H, m), 7.6-7.8 (2H, m). Example 15 Preparation of (1,1'-Biphenyl-4-yl)chloro(chloromethyl )methylsilane The title compound can be prepared by reaction of equimolar quantities of 4-bromobiphenyl, chloro methyldichloro(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 EMI43.1 X = R1, R1 R2 C2H5 CH3 t-C4H9 CH3 n-C4Hg CH3 n-C12H25 C2H5 n-C18H37 n-C6H13 cyclopropyl CH3 cyclohexyl CH3 l-naphthyl i-C3H7 2-naphthyl cyclobutyl phenyl t-C4Hg 4-phenylphenyl n-C4Hg 4-phenylphenyl n-C6H13 4-chlorophenyl n-C4Hg 4-chlorophenyl CH3 4-fluorophenyl n-C6H13 4-phenoxyphenyl cyclohexyl 4-t-butylphenyl n-C3H7 4-trifluoromethoxyphenyl CH3 4-(4-fluorophenyl)phenyl CH3 3-trifluoromethylphenyl t-C4H9 2-thiomethylphenyl cyclopentyl 2,4-dichlorophenyl CH3 2,4-dichlorophenyl n-C4H9 2-chloro-4-phenylphenyl CH3 2,3-dimethylphenyl cyclopropyl 2-methyl-5-fluorophenyl s-C4H9 2,6-dimethoxyphenyl l,l-dimethylpropyl Table IV (continued) X = R1, R1 2 3-methyl-4-chlorophenyl C2H5 3,5-dichlorophenyl n-C5H11 n-C12H25 2,4-dichlorophenyl n-C18H37 phenyl l-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-dimethylphenyl 4-methylthiophenyl 2,6-dimethoxyphenyl 4-methoxyphenyl 3,4-dichlorophenyl 4-methylphenyl Example 16 Preparation of Chloromethyl(methoxy)methyl(phenyl)silane 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 9 (OeO2Q 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 HC1, 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 (42X) of the title compound as a colorless liquid: bp 46-49 (O.o5 mm); nD22 1.5207; nmr (CDC13): 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)methyl (phenyl) silane A mixture of 15.4 g (0.075 mol) of chloro(chloromethyl)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 800 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 HC1, saturated aqueous NaSC03, 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, D 1600, 1435, 1395, 1370, 1260, 1245, 1195, 1125, 1060, 1030, 81-5, 790, 740, 725, 705, 650 cm 1; nmr (CDC13): 0.5 (3H, s), 1.3 (9H, s), 2.9 (2H, s) and 7.3-7.8 (5H, m). Examole 18 Preparation of Chloromethyl(ethoxy)methyl(ohenyl)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 70:3û cyclohexane-ether was added at a rate that held the mixture be-low -50o. The resulting slurry was allowed to warm to room temperature, treated cautiously 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); nD20 1.5144; nmr (CDCl3) 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 EMI47.1 X = R1, R1 R2 R6 C2H5 CH3 CH3 t-C4H9 CH3 t-C4Hg n-C4H9 CH3 C2H5 n-C12H25 C2H5 CH3 n-C18H37 n-C6H13 CH3 cyclopropyl CH3 s-C4H9 cyclohexyl CH3 CH3 1-naphthyl i-C3H7 i-C3H7 2-naphthyl cyclobutyl n-C3H7 phenyl CH3 H phenyl CH3 i-C3H7 bp 72-76 (0.1 mm) phenyl t-C4H9 H 4-phenylphenyl n-C4H9 CH3 4-phenylphenyl t-C4Hg H 4-phenylphenyl CH3 C2H5 4-phenylphenyl CH3 n-C4H9 4-chlorophenyl n-C4H9 n-C4H9 4-chlorophenyl CH3 CH3 4-chlorophenyl CH3 C2H5 4-fluorophenyl n-C6H13 n-C3H7 4-fluorophenyl CH3 C2H5 4-phenoxyphenyl cyclohexyl i-C4H9 4-t-butylphenyl n-C3H7 s-C4H9 3-trifluoromethylphenyl t-C4H9 H 2-methylthiophenyl cyclopentyl C2H5 2,4-dichlorophenyl CH3 CH3 2,4-dichlorophenyl CH3 C2H5 2,4-dichlorophenyl CH3 t-C4H9 Table V (continued) X = R1, R1' R2 R6 2,4-dichlorophenyl n-C4Hg C2H5 2,3-dimethylphenyl cyclopropyl i-C3H7 2-methyl-3-fluorophenyl s-C4H9 n-C3H7 2,6-dimethoxyphenyl 1,1-dimethylpropyl H 3-methyl-4-chlorophenyl C2H5 CH3 3,5-dichlorophenyl n-C5H11 C2H5 n-C12H25 2,4-dichlorophenyl t-C4H9 n-C18H37 phenyl CH3 1-naphthyl phenyl C2H5 phenyl phenyl t-C4Hg 4-fluorophenyl phenyl CH3 4-chlorophenyl phenyl n-C3H7 4-phenylphenyl phenyl C5 4-phenylphenyl phenyl s-C4Hg 4-t-butylphenyl phenyl s-C4Hg 3-fluorophenyl phenyl C2H5 2-methoxyphenyl phenyl H 2-chlorophenyl phenyl CH3 2,4-dichlorophenyl phenyl i-C3H7 3,5-dichlorophenyl phenyl n-C3H7 4-fluorophenyl 4-fluorophenyl t-C4H9 4-fluorophenyl 4-fluorophenyl C2H5 4-chlorophenyl 4-chlorophenyl CH3 4-chlorophenyl 4-chlorophenyl C2H5 <RTI ID=48.6> 4-phenylphenyl 4-phenylphenyl CH3 2, 4-dichlorophenyl 2, 4-dichlorophenyl CH5 3-trifluromethylphenyl 3-trifluoromethylphenyl i-C4H9 2-methoxyphenyl 2-methoxyphenyl H 2-chlorophenyl 4-fluorophenyl H 3-trifluoromethylphenyl 4-t-butylphenyl n-C4H9 2-fluoro-4-chlorophenyl 4-bromophenyl i-C3H7 2,3-dimethylphenyl 4-methylthiophenyl C2H5 Table V (continued) X = R1, R1' R2 R6 2,6-dimethoxyphenyl 4-methoxyphenyl H 3,4-dichlorophenyl 4-methylphenyl i-C4H9 Example 19 Preparation of (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-l-vlmethyl) silane A mixture of 2.6 g (0.010 mol) of (l,l'-biphenyl- 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 80-900 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. 79-860. 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 cm ; nmr (CDC13) 0.4 (6H, s), 3.9 (2H, s), 7.2-7.7 (9H, m), 7.8 (1H, s), 7.9 (1H, 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 chloromethylsilanes react very vigorously with sodium methoxide in dimethylformamide, giving undesired products. Example 20 Isolation of (1,1'-8iphenyl-4-yl)dimethyl(4H-1,2,4- triazol-4-ylmethyl) silane A 5 g sample of once-crystallized l,l'-(biphenyl 4-yl)dimethyl(lH-1,2,4-triazol-1-ylmethyl)silane, prepared as in Example 14 using sodium methoxide-1,2,4triazole, was sbjected to high pressure liquid chromatography (Waters Prep PAK-500 silica gel cartridge, 250 ml per minute flow rate). Elution with ethyl acetate-hexane 50:50 removed first some minor impurities and then provided the pure lH-1,2,4-triazol-1-ylmethyl compound, m.p. 99-1000. Continued elution with ethyl acetate-acetonitrile 80:20 provided a small amount of the title compound as a colorless solid: m.p. 130-1330C; nmr (CDC13) 0.4 (6H, s), 3.7 (2H, s), 7.2-7.7 (9H, m), 7.9 (2H, s); microanalysis for Cj7H19N3Si (mw 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 Dimethyl(phenyl)(lH-1,2,4-triazol-l-yl- methyl) silane A mixture of 9.0 ml (9.2 g, 0.050 mol) of chloromethyldimethylphenylsilane and 5.5 g (0.060 mol) of 1,2,4-triazole sodium salt in 25 ml of dimethylformamide was stirred and warmed to 90-950C 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 22 8.1 9 (75%) of a pale brown oil, nD 1.5350, con- taining the title compound and minor impurities as judged by nmr. A purer sample was obtained by distillation: bp 99 (0.02 mm); nD20 1.5403; nmr (CDCl3) 0.4 (6H, s), 3.8 (2H, s), 7.2-7.7 (5H, m), 7.7 (1H, s), 7.8 (1H, s); analysis for CllH15N3Si (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-1,2,4- triazo 1-1-Y imethyl) silane A mixture of 2.2 g (0.010 mol) of chloromethyl(4chlorophenyl)dimethylsilane 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 title compound as a yellow liquid: nD21 1.5428; ir (neat) 1555, 1470, 1245, 1130, 1080, 1010, 835, 805, 795, 735 cm 1; nmr (CDC13) 0.4 (6H, s), 3.8 (2H, s), 7.4 (4H, broad s), 7.8 (1H, s), 7.9 (1H, s). Example 23 Preparation of (2,4-Dichlorophenyl)dimethyl(lH-1,2,4- triazol-1-ylmethyl)silane A mixture of 5.1 9 (0.020 mol) of chloromethyl (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: nD23 1.5580; ir (neat) 1550, 1485, 1440, 1345, 1260, 1240, 1130, 1085, 1025, 1005, 835 cm¯l; nmr (CDC13) 0.5 (6H, s), 4.1 (2H, s), 7.2-7.5 (3H, m), 7.8 (1H, s), 7.9 (1H, s). Example 24 Preparation of bis (4-Chlorophenyl)methyl(1H-1,2,4triazol-1-ylmethyl)silane A mixture of 6.3 g (0.020 mol) of chloromethylbis(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 800C for 4 hours. The resulting slurry was cooled, diluted with water1 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: nD26 1.5966; nmr (CDCl3) 0.7 (3H, s), 4.1 (2H, s), 7.2-7.5 (8H, m), 7.8 (1H, s), 7.9 (1H, s). Example 25 Preparation of bis(4-Fluorophenyl)methyl(lH-1,2,4- triazol-1-ylmethyl)silane 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 800 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: nD21 1.5538; ir (neat) 3065, 3030, 2960, 2925, 1590, 1500, 1270, 1235, 1165, 1110, 1010, 630, 790 cm 1; nmr (CDC13): 0.7 (3H, s), 4.2 (2H, s), 7.1 (4H, t, J = 9), 7.5 (4H, d of d, J = 6 and. 9), 7.8 (1H, s) and 7.9 (1H, 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. Table VI EMI56.1 R1 R2 R3 C2H5 CH3 CH3 nD22 1.4713 i-C3H7 CH3 CH3 19 n-C4H9 CH3 CH3 nD19 1.4687 t-C4H9 CH3 CH3 n-C12H25 CH3 CH3 nD23 1.4626 n-C14H29 CH3 CH3 n-C18H37 CH3 CH3 nD21 1.4597 cyclopropyl CH3 CH3 cyclobutyl CH3 CH3 cyclopentyl CH3 CH3 cyclohexyl CH3 CH3 nD22 1.4906 1-naphthyl CH3 CH3 nD23 1.6051 2-naphthyl CH3 CH3 4-bromophenyl CH3 CH3 nD20 1.5467 4-fluorophenyl CH3 CH3 bp 108 (0.2 mm) 4-methoxyphenyl CH3 CH3 nD26 1.5401 4-phenoxyphenyl CH3 CH3 nD22 1.5754 4-(4-chlorophenoxy)phenyl CH3 CH3 nD22 1.5703 4-(4-fluorophenoxy)phenyl CH3 CH3 4-(4-trifluormethylhenoxy)phenyl CH3 CH3 4-(4-methylphenoxy)phenyl CH3 CH3 4-thiomethylphenyl CH3 CH3 nD23 1.5790 4-trifluoromethylphenyl CH3 CH3 nD22 1.4909 4-methylphenyl CH3 CH3 nD21 1.5350 Table VI (continued) R1 R2 R3 4-methylsulfonylphenyl CH3 CH3 nD21 1.5538 4-i-propylphenyl CH3 CH3 4-t-butylphenyl CH3 CH3 nD23 1.5125 4-cyclohexylphenyl CH3 CH3 nD21 1.5235 4-trifluoromethoxyphenyl CH3 CH3 nD22 1.4768 4-(4-chlorophenyl)phenyl CH3 CH3 4-(4-bromophenyl)phenyl CH3 CH3 nD22 1.5802 4-(4-methylphenyl)phenyl CH3 CH3 4-(4-trifluoromethylphenyl)phenyl CH3 CH3 4-(4-fluorophenyl)phenyl CH3 CH3 3-phenylphenyl CH3 CH3 nD21 1.5939 3-trifluoromethylphenyl CH3 CH3 nD20 1.4845 3-chlorophenyl CH3 CH3 m.p. 37-43 2-trifluoromethylphenyl CH3 CH3 nD23 1.4964 2-phenylphenyl CH3 CH3 nD22 1.5900 2-chlorophenyl CH3 CH3 nD22 1.5442 2-methoxyphenyl CH3 CH3 nD21 1.5216 2,3-dimethylphenyl CH3 CH3 2,3-dimethoxyphenyl CH3 CH3 nD22 1.5322 2,4-difluorophenyl CH3 CH3 2-fluoro-4-chlorophenyl CH3 CH3 2-chloro-4-fluorophenyl CH3 CH3 2-chloro-4-phenylphenyl CH3 CH3 2-fluoro-4-phenylphenyl CH3 CH3 2-methyl-5-chlorophenyl CH3 CH3 2,6-dimethoxyphenyl CH3 CH3 nD23 1.5404 2,6-dimethylphenyl CH3 CH3 Table VI (continued) R1 R2 R3 3,4-dichlorophenyl CH3 CH3 nD22 1.5602 3-methyl-4-fluorophenyl CH3 CH3 3,5-dichlorophenyl CH3 CH3 m.p. 63-690 C2H5 C2H5 CH3 i-C3H7 cyclohexyl CH3 n-C4H9 n-C4H9 CH3 nD22 1.4672 n-C10H21 cyclopropyl CH3 n-C12H25 n-C3H7 CH3 n-C14H29 i-C3H7 CH3 n-C18H37 3-methylbutyl CH3 cyclopropyl n-C6H13 CH3 cyclopentyl cylopentyl CH3 cyclohexyl cyclohexyl CH3 1-naphthyl n-C4H9 CH3 1-naphthyl t-C4H9 CH3 2-naphthyl n-C5H11 CH3 phenyl n-C3H7 CH3 phenyl n-C4H9 CH3 nD21 1.5297 phenyl 1,1-dimethylpropyl CH3 phenyl n-C6H13 CH3 4-phenylphenyl C2H5 CH3 4-phenylphenyl n-C4H9 CH3 nD22 1.5838 4-bromophenyl i-C3H7 CH3 4-chlorophenyl n-C4H9 CH3 nD21 1.5344 4-flurophenyl n-C4H9 CH3 nD22 1.5120 4-phenoxyphenyl t-C4Hg CH3 4-i-propylphenyl cyclopropyl CH3 4-t-butylphenyl i-C4H9 CH3 3-phenylphenyl i-C4H9 CH3 3-trifluoromethylphenyl s-C4Hg CH3 Table VI (continued) R1 R2 R3 3-chlorophenyl n-C5H11 CH3 2-methoxyphenyl t-C4H9 CH3 2-thiomethylphenyl cyclobutyl CH3 2-phenylphenyl i-C4H9 CH3 2,4-dichlorophenyl n-C4H9 CH3 nD23 1.5411 2,4-dichlorophenyl cyclopropyl CH3 2,3-dimethylpheynl n-C3H7 CH3 2-methyl-5-flurophenyl cyclopentyl CH3 2,5-dimethoxyphenyl 4-methylpentyl CH3 2,6-dimethylphenyl l-methylbutyl CH3 3,4-dichlorphenyl n-C5H11 CH3 3,5-dichlorophenyl n-C4H9 CH3 3,5-dichlorophenyl cyclohexyl CH3 3-methyl-4-chlorophenyl cyclopropyl CH3 phenyl phenyl CH3 nD22 1.5852 4-flurophenyl phenyl CH3 nD20 1.5718 4-chlorphenyl phenyl CH3 nD22 1.5926 4-bromophenyl phenyl CH3 nD22 1.6076 4-phenylphenyl phenyl CH3 nD21 1.6328 4-t-butylphenyl phenyl CH3 4-thiomethylphenyl phenyl . CH3 4-phenoxyphenyl phenyl CH3 4-trifluoromethoxyphenyl phenyl CH3 4-methylsulfonylphenyl phenyl CH3 4-cyclohexylphenyl phenyl CH3 4-(4-fluorophenyl)phenyl phenyl CH3 3-trifluoromethylphenyl phenyl CH3 2-chlorophenyl phenyl CH3 nD20 1.5742 2-methoxyphenyl phenyl Table VI (continued) R1 R2 R3 2,4-dichlorophenyl phenyl CH3 no 1.5941 2-chloro-4-phenylphenyl phenyl CH3 2-fluoro-4-phenylphenyl phenyl CH3 3,5-dichlorophenyl phenyl CH3 2,5-dimethoxyphenyl phenyl CH3 2,6-dimethoxyphenyl phenyl CH3 21 4-bromophenyl 4-bromophenyl CH3 nD21 1.6245 4-phenylphenyl 4-phenylphenyl CH3 m.p. 42-460 4-methoxyphenyl 4-methoxyphenyl CH3 nD21 1.5890 3-trifluoromethylphenyl 3-trifluoromethylphenyl CH3 2-chlorophenyl 2-chlorophenyl CH3 nD21 1.5965 2-methoxyphenyl 2-methoxyphenyl CH3 2,4-dichlorophenyl 2,4-dichlorophenyl CH3 nD22 1.6009 3,5-dichlorophenyl 3,5-dichlorophenyl CH3 2-chlorophenyl 4-chlorophenyl CH3 nD20 1.5918 2-chlorophenyl 4-fluorophenyl CH3 4-phenylphenyl 4-chlorophenyl CH3 4-phenylphenyl 4-fluorophenyl CH3 4-phenylphenyl 2,4-dichlorophenyl CH3 4-fluorophenyl 2, 4-dichlorophenyl CH3 4-chlorophenyl 2,4-dichlorophenyl CH3 1-naphthyl 2,6-dimethoxyphenyl CH3 4-phenoxyphenyl 3 ,4-dichlorophenyl CH3 C2H5 C2H5 C2H5 i-C3H7 i-C3H7 i-C3H7 n-C4H9 n-C4H9 n-C4H9 n-C8H17 C2H5 cyclopentyl n-C14H29 cyclopropyl 1-methylbutyl n-C18H37 n-C6H13 n-C6H13 cyclopropyl C2H5 s-C4H9 Table VI (continued) R1 R2 R3 cyclohexyl n-C3H7 n-C3H7 1-nephthyl n-C4H9 n-C4H9 2-naphthyl n-C4H9 cyclobutyl phenyl cyclopropyl n-C6H13 4-phenylphenyl C2H5 C2H5 4-phenylphenyl n-C4H9 n-C4H9 4-phenylphenyl n-C6H13 n-C6H13 4-phenylphenyl cyclohexyl - cyclohexyl 4-chlorophenyl n-C4H9 n-C4H9 4-fluorophenyl n-C3H7 n-C3H7 4-phenoxyphenyl n-C4Hg cyclohexyl 4-(4-chlorophenoxy)phenyl n-C4H9 n-C4H9 4-t-butylphenyl s-C4H9 i-C4H9 3-methoxyphenyl C2H5 t-C4H9 3-trifluoromethylphenyl s-C4H9 s-C4H9 2-thiomethylphenyl i-C3H7 3-methylbutyl 2-phenylphenyl cyclohexyl cyclohexyl 2,4-dichlorophenyl n-C4H9 n-C4H9 2,6-dimethylphenyl t-C4Hg t-C4Hg 3,5-dichlorophenyl cyclopentyl cyclopentyl 3-methyl-4-chlorophenyl s-C4H9 s-C4H9 2-methyl-5-fluorophenyl n-C4H9 i-C4H9 C2H5 phenyl phenyl cyclohexyl phenyl phenyl n-C18H37 phenyl phenyl n-C4H9 4-chlorophenyl 4-chlorophenyl n-C12H25 4-chlorophenyl 4-chlorophenyl 1-naphthyl 4-fluorophenyl 4-f luorophenyl cyclopropyl phenyl 4-t-butylphenyl n-C4H9 phenyl 4-phenylphenyl t-C4H9 phenyl 2,4-dichlorophenyl n-C3H7 phenyl 3-trifluoromethylphenyl Table VI (continued) R1 R2 R3 i-C4H9 phenyl 3, 5-dichlorophenyl cyclopentyl phenyl 2,6-dimethoxyphenyl 14H29 4-chlorophenyl 2-fluorophenyl n-C4H9 4-fluorophenyl 4-phenylphenyl phenyl phenyl phenyl m.p. 118-121 4-chlorophenyl 4-chlprophenyl 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-dichlorphenyl 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 l-naphthyl 4-bromophenyl 3-methylphenyl 4-phenoxyphenyl <RTI ID=62.6> 3,5-dimethylphenyl 3,4-dichlorophenyl Example 26 Preparation of (3,5-Dimethyl-1H-1,2,4-triazol-1-ylmethyl)[bis(4-fluorohenyl)]methylsilane The title compound is prepared by applying the procedure of Example 25 to equimolar quantities of chloromethylEbis(4-fluorophenyl) )methylsilane and 3,5-dimethyl-1,2,4-triazole sodium salt. Related compounds may be made by substitutwng salts of 3-methyl-1,2,4-triazole for the 3,5-dimethyltriazole salt. Example 27 Preparation of (1,1'-Biphenyl-4-yl)dimethyl(3-methyl1H-1,2,4-triazol-1-ylmethyl)silane A solution of 5.9 g (0.020 mol) of (l,l'-biphenyl-4-yl)dimethyl(1H-1,2,4-triazol-1-ylmethyl)silane in 40 ml of dry tetrahydrofuran was chilled to -400 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 iodine, 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 hexanesethyl 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 cm'l; nmr (CDCl3) 0.5 (6H, s), 2.2 (3H, s), 3.7 (2H, s), 7.2-7.7 (9H, m), 7.8 (1H, 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)- dimethyl(5-methyl-lH-1,2,4-triazol-1-ylmethyl)silane. The procedures of Examples 26 and 27 may be used to prepare the compounds of Table VII. Table VII EMI65.1 R1 R2 R3 Q1 Q2 C2H5 CH3 CH3 CH3 CH3 n-C18H37 CH3 CH3 H CH3 cyclohexyl CH3 CH3 CH3 OH3 l-naphthyl CH3 CH3 CH3 OH3 phenyl CH3 CH3 H CH3 phenyl CH3 CH3 CH3 H 4-phenylphenyl CH3 CH3 CH3 CH3 4-(4-fluorophenyl)phenyl CH3 CH3 CH3 CH3 4-phenoxyphenyl CH3 CH3 CH3 CH3 3-trifluoromethylphenyl CH3 CH3 CH3 CH3 2-methoxyphenyl CH3 CH3 CH3 CH3 2,4-dichlorophenyl CH3 CH3 CH3 CH3 2-chloro-4-phenylphenyl CH3 CH3 CH3 CH3 phenyl n-C4H9 CH3 CH3 CH3 4-phenylphenyl n-c4H9 CH3 H CH3 2,4-dichlorophenyl n-C6H13 CH3 CH3 CH3 4-(4-chlorophenoxy)phenyl cyclohexyl CH3 CH3 CH3 phenyl phenyl CH3 H CH3 4-fluorophenyl phenyl CH3 CH3 CH3 4-fluorophenyl phenyl CH3 H CH3 4-chlorophenyl phenyl CH3 H CH3 4-fluorophenyl 4-fluorophenyl CH3 H CH3 4-fluorophenyl 4-fluorophenyl CH3 CH3 H 4-chlorophenyl 4-chlorophenyl CH3 H CH3 4-chlorophenyl 4-chlorophenyl CH3 CH3 CH3 2-chlorophenyl 4-chlorophenyl CH3 H CH3 Table VII (continued) R1 R2 R3 Q1 Q2 2, 4-dichlorophenyl 2,4-dichlorophenyl CH3 CH3 CH3 n-C18H37 n-C6H13 n-C6H13 CH3 CH3 1-naphthyl n-C4H9 n-C4H9 H CH3 phenyl phenyl phenyl H CH3 phenyl phenyl phenyl CH3 H phenyl phenyl phenyl CH3 CH3 Example 28 Preparation of the 1:1 complex of (1,1'-8iphenyl-4-yl)- dimethyl (1H-1,2,4-triazol-1-ylmethyl)silane and Cuprous Chloride A mixture of 5.0 g (0.017 mol) of (l,l'-biphenyl4-yl)dimethyl(1H-1,2,4-triazol-1-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. 85-90o; ir (NujolR) 3110, 1590, 1280, 1250, 1120, 1010, 990, 840, 825, 760, 700 cm The following metal complexes of (l,l'-biphenyl4-yl)dimethyl(lH-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: 21 1.5737 no 1:1 Complex with manganous sulfate: m.p. 244-2500 (decomp.) Example 29 Preparation of the 4-Dodecylbenzenesulfonate Salt of (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4-triazol-1-ylmethyl)silane A solution of 1.0 g (0.0034 mol) of (l,l'-bi phenyl-4-yldimethyl(lH-1,2,4-triazol-1-ylmethyl)- silane in 10 ml of dichloromethane was combined with a solution of 1.1 g (0.0034 mol) of 4-dodecylbenzenesulfonic acid in 10 ml of dichloromethane. The resulting solution was evaporated to leave the title salt as a viscous yellow oil: n20 1.5645; ir (neat) 3110, 0 3050, 3020, 2960, 2920, 2850, 2570, 1920, 1600, 1545, 1485, 1455, 1405, 1250, 1225, 1165, 1120, 1030, 110, 990, 845, 825, 755, 735, 700, 670, 635 cm Example 30 Preparation of the 2:1 complex of Ebis(4-Fluoro- phenyl)]methyl(lH-1,2,4-triazol-1-ylmethyl)silane and Cupric Chloride A mixture of 1.0 g (0.0032 mol) of Ebis(4-fluoro- phenyl)]methyl(1H-1,2,4-triazol-1-ylmethyl)silane and 0.2 g (0s.0016 mol) of cupric chloride in 30 ml of tetrahydrofuran was refluxed under N2 fo 30 minutes and evaporated to leave the title complex as a bluegreen glass: no distinct m. p.; ir (NujolR) 1580, 1490, 1230, 1160, 1110, 830, 785 cm'l, 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-1,2,4-triazol- l-vlmethyl) (methoxy)methylsilane A mixture of (l,l'-biphenyl-4-yl)chlorochloro- methylmethylsilane and two equivalents of 1,2,4-triazole sodium salt in dimethylformamide is warmed to 80-90aC 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 R6 = OH, water is used instead of an alcohol, and hydrolysis is conducted at 20-250C instead of 700. Example 32 Preparation of (l,l-dimethylethoxy)methyl(phenyl)(lH- 1,2, 4-triazol-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 800 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: nD21 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'l; nmr (CDCl3): 0.6 (3H, s), 1.3 (9H, s), 3.9 (2H, s), 7.3-7.7 (5H, m), 7.9 (1H, s) and 8.0 (1H, s). The compounds of Table VIII and IX in which Q1=Q2=H can be made using the procedures of Examples 31 and 32. Table VIII EMI70.1 R1 R2 R6 C2H5 CH3 CH3 t-C4Hg CH3 t-C4H9 n-C4H9 CH3 C2H5 n-C12H25 C2H5 CH3 n-C18H37 n-C6H13 CH3 cyclopropyl CH3 s-C4H9 cyclohexyl C CH3 CH3 1-nephthyl i-C3H7 i-C3H7 2-naphthyl cyclobutyl n-C3H7 phenyl CH3 H phenyl CH3 CH3 phenyl CH3 C2H5 phenyl CH3 i-C3H7 nD20 1.5367 phenyl t-C4H9 H 4-phenylphenyl n-C4H9 CH3 4-phenylphenyl t-C4H9 H 4-phenylphenyl CH3 C2H5 4-phenylphenyl CH3 n-C4H9 4-chlorophenyl n-C4H9 n-C4H9 4-chlorophenyl CH3 CH3 4-chlorophenyl CH3 C2H5 4-fluorophenyl n-C6H13 n-C3H7 4-fluorophenyl CH3 C2Hs 4-phenoxyphenyl cyclohexyl i-C4H9 4-t-butylphenyl n-C3H7 s-C4H9 3-trifluoromethylphenyl t-C4H9 H 2-methylthiophenyl cyclopentyl C2H5 Table VIII (continued) R1 R2 R6 2,4-dichlorophenyl CH3 CH. 2,4-dichlorophenyl CH3 C2H5 2,4-dichlorophenyl CH3 t-C4H9 2,4-dichlorophenyl n-C4H9 C2H5 2, 3-dimethylphenyl cyclopropyl i-C3H7 2-methyl-5-flurophenyl s-C4H9 n-C3H7 2,6-dimethoxyphenyl 1,1-dimethylpropyl H 3-methyl-4-chlorophenyl C2H5 CH3 3,5-dichlorophenyl n-C5H11 C2H5 n-C12H25 2,4-dichlorophenyl t-C4H9 n-C18H37 phenyl OH3 1-naphthyl phenyl C2H5 phenyl phenyl t-C4H9 4-fluorophenyl phenyl CH3 4-chlorophenyl phenyl n-C3H7 4-phenylphenyl phenyl C2H5 4-phenyl phenyl s-C4H9 4-t-butylphenyl phenyl s-C4H9 3-fluorophenyl phenyl C2H5 2-methoxyphenyl phenyl H 2-chlorophenyl phenyl CH3 2,4-dichlorophenyl phenyl i-C3H7 3,5-dichlorophenyl phenyl n-C3H7 4-fluorophenyl 4-fluorophenyl t-C4H9 4-fluorophenyl 4-fluorophenyl C2H5 4-chlorophenyl 4-chlorophenyl CH3 4-chlorophenyl 4-chlorophenyl C2H5 4-phenylphenyl 4-phenylphenyl CH3 2,4-dichlorophenyl 2,4-dichlorophenyl C2H5 3-trifluorophenyl 3-trifluoromethylphenyl i-C4H9 2-methoxyphenyl 2-methoxyphenyl 2-chlorophenyl 4-fluorophenyl Table VII1 (continued) R1 R2 6 3-trifluoromethylphenyl 4-t-butylphenyl n-C4H9 2-fluro-4-chlorophenyl 4-bromophenyl i-C3H7 2,3-dimethylphenyl 4-methylthiophenyl C2H5 2,6-dimethylphenyl 4-methoxyphenyl H 3,4-dichlorophenyl 4-methylphenyl i-C4H9 Table IX EMI73.1 R1 R2 R6 Q1 Q2 C2H5 CH3 CH3 CH3 CH3 cyclohexyl CH3 i-C3H7 H CH3 n-C18H37 n-C6H13 t-C4H9 CH3 CH3 1-naphthyl CH3 i-C3H7 CH3 CH3 phenyl CH, t-C4H9 H CH3 phenyl CH3 t-C4Hg CH3 H phenyl CH3 t-C4H9 CH3 CH3 phenyl CH3 s-C4H9 H CH3 phenyl CH3 i-C4H9 H CH3 4-phenylphenyl n-C4H9 t-C4H9 H CH3 4-phenylphenyl CH3 t-C4Hg H CH3 4-phenylphenyl CH3 t-C4H9 CH3 CH3 4-chlorophenyl CH3 t-C4Hg H CH3 4-chlorophenyl CH3 t-C4H9 CH3 CH3 4-fluorophenyl CH3 t-C4H9 H CH3 4-fluorophenyl CH3 t-C4Hg CH3 CH3 phenyl phenyl C2H5 CH3 CH3 phenyl phenyl n-C3H7 CH3 CH3 4-fluorophenyl phenyl i-C3H7 H CH3 4-fluorophenyl phenyl t-C4Hg CH3 CH3 4-chlorophenyl phenyl i-C3H7 H CH3 2,4-dichlorophenyl phenyl H CH3 CH3 4-fluorophenyl 4-fluorophenyl t-C4H9 H CH3 4-fluorophenyl 4-fluorophenyl t-C4H9 CH3 H 4-fluorphenyl 4-fluorophenyl t-C4H9 CH3 CH3 2-methoxyphenyl 2-methoxyphenyl C3H4 CH3 CH3 3-methylphenyl 3-methylphenyl i-C4H9 H CH3 Example 33 Preparation of Ohloromethvl(dichloro)phenylsilane A solution of 25.1 ml (36.8 g, 0.200 mol) of chloromethyltrichlorosilane in 400 ml dry tetrahydrofuran 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 ether7 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 (COC13): # 3.3 (s, 2) and 7.1-7.9 (m, 5). Example 34 Preparation of-Chlbromethyl(diethoxy)phenylsilane A solution of 1.0 g (0.0044 mol) of chloromethyl (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, filtration 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 0.80 (73%) of the title compound as a colorless oil: nmr (CDC13): 1.25 (t, 6, J = 6Hz), 3.0 (s, 2), 3.9 (q, 4, J = 6Hz) and 7.2-7.9 (m, 5). Example 35 Preparation of Chloromathyl(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 15 ml of dimethylformamide was stirred under N2 while 2.5 ml (1.9 g, 0.018 mnl) of triethylamine was added dropwise. The resulting slurry was warmed to 800 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 oversilica gel, eluting with petroleum ether, provided 1.4 g (58%) of the title compound as a colorless liquid: 22 n22 1.4741; nmr (CDC13) 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 EMI76.1 R1 R6 C2H5 t-C4Hg n-C4H9 C2H5 n-C18H37 CH3 cyclohexyl n-C H 1-naphthyl i-C4H9 phenyl CH3 phenyl n-C3H7 phenyl t-C4H9 4-phenylphenyl C2H5 4-phenylphenyl n-C4Hg 4-fluorophenyl CH3 4-fluorophenyl 02H5 4-chlorophenyl C2H5 4-chlorophenyl i-C3H7 3-trifluoromethylphenyl s-C4Hg 2-methoxyphenyl n-C3H 2,3-dimethylphenyl i-C4H9 2,4-dichlorophenyl CH3 2,4-dichlorophenyl C2H5 2-methoxy-5-fluorophenyl i-C3H7 2,6-dimethoxyphenyl CH3 3,4-dichlorophenyl C2H5 3,5-dichlorophenyl n-C4Hg Table XI EMI77.1 EMI77.2 <tb> Rl <SEP> R6 <tb> C <SEP> 5 <SEP> CH <SEP> SH2 <tb> <SEP> CH3 <tb> n-C4Hg <SEP> -CH2CH <tb> n-C18H37 <SEP> CH2CH2CH2 <tb> <SEP> O,2H5 <tb> cyclohexyl <SEP> -CH2CH <tb> 1-naphthyl <SEP> CH2CH2 <tb> phenyl <SEP> -CH2CH2 <tb> <SEP> ,C2H5 <tb> phenyl <SEP> -CH2CH <tb> <SEP> n-C,3 <SEP> 7 <tb> phenyl <SEP> -CH2CH <tb> phenyl <SEP> -O(OH) <SEP> 2O(OH3)2- <SEP> bp <SEP> 142-1620(10mm) <tb> 4-phenylphenyl <SEP> -CH2CH2 <tb> <SEP> ,C2Hs <tb> 4-phenylphenyl <SEP> -CH2CH <tb> <SEP> CH3 <SEP> CH3 <tb> 4-phenylphenyl <SEP> -CH-CH <SEP> <tb> 4-fluorophenyl <SEP> -CH2CH2 <tb> <SEP> CH3 <tb> 4-fluorophenyl <SEP> -CH2CH <tb> <SEP> O,2H5 <tb> 4-chlorophenyl <SEP> -CH2CH <tb> 4-chlorophenyl <SEP> -C(CH3)2O(CH3)2 <tb> <SEP> OH <tb> 3-trifluoromethylphenyi <SEP> -CHCH2C(O;: :3;2 <tb> Table XI (continued) EMI78.1 <tb> R1 <SEP> R6 <tb> <SEP> n-O,4H9 <tb> 2-methoxyphenyl <SEP> -CH2CH <tb> 2,3-dimethylphenyl <SEP> -CHH, <tb> <SEP> C, <SEP> 2H5 <tb> 2, <SEP> 4-dichlorophenyl <SEP> -CH2CH <tb> <SEP> n-C,3H7 <tb> 2,4-dichlorophenyl <SEP> -CH2CH <tb> <SEP> CH3 <SEP> CH3 <tb> 2-methoxy-5-fluorophenyl <SEP> -CHC(CH3)2CH <tb> 2, <SEP> 6-dimethoxyphenyl <SEP> -CH2CH2 <tb> <SEP> OH <SEP> CH3 <tb> 3,4-dichlorophenyl <SEP> -CHCH2CH <tb> <SEP> C,H3 <SEP> O,H3 <tb> 3,5-dichlorophenyl <SEP> -CH--CH <tb> C2H5 <SEP> -CH2CH=CH2 <tb> <SEP> CH3 <SEP> CH3 <tb> n-C18H37 <SEP> -MCHcF=H2CH <tb> phenyl <SEP> -CH2OH=CHCH2 <tb> phenyl <SEP> -C(CH3)2CH=CHC(CH3)2 <tb> <SEP> CH3 <SEP> CH3 <SEP> bp <SEP> 57-60a. <tb> phenyl <SEP> CHCH2CH2CH <SEP> bp <SEP> (0.15 <SEP> mm) <tb> phenyl <SEP> -C(CH3)2CH2CHzC(CH3)2 <tb> 4-phenylphenyl <SEP> -CH <SEP> 2CH=CHCH2 <tb> <SEP> O,H3 <SEP> CH3 <tb> 4-phenylphenyl <SEP> -CH2C=CCH2 <tb> 4-fluorophenyl <SEP> -CH2-CH=CHCH2 <tb> 4-chlorophenyl <SEP> -CH2CH2CH2CH2 <tb> <SEP> n-C <SEP> H <tb> 4-phenoxyphenyl <SEP> H2CH2CH2CH <tb> <SEP> O,H3 <SEP> O,H3 <tb> 3-trifluoromethylphenyl <SEP> -CHCH=CHCH <tb> <SEP> O,H3 <SEP> C,H3 <tb> 2-methoxyphenyl <SEP> -CH2CH-CHCH2 Example 36 Preparation of Phenylbis (2-propoxy) (1H-1,2,4-triazol l-ylmethyl ) silane The title compound can be made by applying the procedure of Example 32 to chloromethyl(phenyl)bis (2-propoxy)silane: nD22 1.4962; nmr (CDCl3) 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 XII and XIII can be made similarly. Table XII EMI80.1 R1 R6 Q1 Q2 C2H5 t-C4Hg H H n-C4H9 C2H5 H H n-C18H37 CH3 H H cyclohexyl n-C3H7 H H l-naphthyl i-C4Hg H H phenyl CH3 CH3 CH3 phenyl n-C3H7 H CH3 phenyl i-C3H7 CH3 CH3 phenyl t-C4Hg H H 4-phenylphenyl C2H5 CH3 CH3 4-phenylphenyl n-C4H9 H H 4-fluorophenyl CH3 H H 4-fluorophenyl C2H5 H H 4-chlorophenyl C2H5 H H 4-chlorophenyl i-C3H7 H H 3-trifluoromethylphenyl s-C4H9 CH3 CH3 2-methoxyphenyl n-C3H7 H CH3 2, 3-dimethylphenyl i-C4H9 CH3 CH3 2,4-dichlorophenyl CH3 H H 2,4-dichlorophenyl C2Hs H H 2-methoxy-5-fluorophenyl i-C3H7 H H 2,6-dimethoxyphenyl CH3 H H 3,4-dichlorophenyl C2H5 H H 3,5-dichlorophenyl n-C4H9 H H Table XIII EMI81.1 EMI81.2 <tb> R1 <SEP> R6 <SEP> Ql <SEP> Q2 <tb> O2Hs <SEP> -CH2CH2- <SEP> CH3 <SEP> CH3 <tb> <SEP> CH3 <tb> n-O4H9 <SEP> CH2CH <SEP> H <SEP> CH3 <tb> n-C18H37 <SEP> CH2CH2CH2 <SEP> " <SEP> H <SEP> H <tb> <SEP> O,2H5 <tb> cyclohexyl <SEP> CH2CH <SEP> H <SEP> CH3 <tb> l-naphthyl <SEP> -CH2CH2- <SEP> CH3 <SEP> H <tb> phenyl <SEP> CH <SEP> iH2 <SEP> CH3 <SEP> CH3 <tb> <SEP> O2H <tb> phenyl <SEP> -CH2CH- <SEP> H <SEP> H <tb> <SEP> ¯ <SEP> ,3 <SEP> 7 <tb> phenyl <SEP> -CH2CH- <SEP> H <SEP> H <tb> phenyl <SEP> -C(CH3)2C(CH3)2- <SEP> H <SEP> H <tb> 4-phenylphenyl <SEP> -CH2OH2- <SEP> H <SEP> H <tb> <SEP> C12H5 <tb> 4-phenylphenyl <SEP> -CH2CH- <SEP> H <SEP> H <tb> <SEP> O1H3 <SEP> O1H3 <tb> 4-phenylphenyl <SEP> -CH <SEP> - <SEP> CH- <SEP> H <SEP> H <tb> 4-fluorophenyl <SEP> CH2OH2 <SEP> H <SEP> H <tb> <SEP> CH3 <tb> 4-fluorophenyl <SEP> -CH2CH- <SEP> H <SEP> H <tb> <SEP> ,C2H5 <tb> 4-chlorophenyl <SEP> -CH2CH- <SEP> H <SEP> H <tb> 4-chlorophenyl <SEP> -C(CH3)2C(CH3)2- <SEP> H <SEP> H <tb> <SEP> OH <tb> 3-trifluoromethylphenyl <SEP> -CHCH2C( <SEP> I3. <SEP> 2 <tb> Table XIII (continued) EMI82.1 <tb> R1 <SEP> R6 <SEP> Ol <SEP> Q2 <tb> <SEP> n-C,4H9 <tb> 2-methoxyphenyl <SEP> -CH2CH- <SEP> H <SEP> CH3 <tb> 2,3-dimethylphenyl <SEP> -CH2CH2- <SEP> CH3 <SEP> CH3 <tb> <SEP> O,2Hs <tb> 2,4-dichlorophenyl <SEP> -CH2OH- <SEP> H <SEP> H <tb> <SEP> n-C3,H7 <tb> 2,4-dichlorophenyl <SEP> -CHljl- <SEP> H <SEP> H <tb> <SEP> O,H3 <SEP> O,H3 <tb> 2-methoxy-5-fluorophenyl <SEP> -CHC(CH3)2CH- <SEP> H <SEP> H <tb> 2,6-dimethoxyphenyl <SEP> -CH2CH2- <SEP> H <SEP> H <tb> <SEP> O,H3 <SEP> OH3 <tb> 3,4-dichlorophenyl <SEP> -CHCH2CH- <SEP> H <SEP> H <tb> <SEP> CH3 <SEP> CH3 <tb> 3, <SEP> 5-dichlorophenyl <SEP> -CH--CH- <SEP> H <SEP> H <tb> C2H5 <SEP> -CH2CH=CHCH2- <SEP> CH3 <SEP> CH3 <tb> <SEP> OH3 <SEP> O1H3 <tb> n-O18H37 <SEP> CHCH2CH2CH <SEP> H <SEP> CH3 <tb> phenyl <SEP> -OH2OH=OHOH2- <SEP> H <SEP> H <tb> phenyl <SEP> -C(CH3)2CH=CHC(CH3)2- <SEP> H <SEP> H <tb> <SEP> C,H3 <SEP> CH3 <tb> phenyl <SEP> C <SEP> OH <SEP> OH- <SEP> H <SEP> H <tb> phenyl <SEP> -C(CH3)2CH2CH2C(CH3)2 <SEP> H <SEP> H <tb> 4-phenylphenyl <SEP> -CH2CH=CHCH2- <SEP> H <SEP> H <tb> <SEP> O1H3 <SEP> O1H3 <tb> 4-phenylphenyl <SEP> -CH2r <SEP> - <SEP> CCH2- <SEP> H <SEP> H <tb> 4-fluorophenyl <SEP> -CH2-CH=CHCH2- <SEP> H <SEP> H <tb> 4-chlorophenyl <SEP> -CH2CH2CH2CH2- <SEP> H <SEP> H <tb> <SEP> n-C,4H9 <tb> 4-phenoxyphenyl <SEP> CH2CH2CH2CH <SEP> CH3 <SEP> CH3 <tb> <SEP> O1H3 <SEP> O1H3 <tb> 3-trifluoromethylphenyl <SEP> -CHCH=CHCH- <SEP> H <SEP> CH3 <tb> <SEP> CH3 <SEP> CH3 <tb> 2-methoxyphenyl <SEP> -CH2OH-CHOH2- <SEP> H <SEP> H <tb> Example 37 Preparation of (1,1'-Biphenyl-4-yl)dimethyl(1H-imida zol-l-ylmethyl) silane A mixture of 2.6 g (0.010 mol) of (l,l'-biphenyl4-yl)chloromethyldimethylsilane and 1.1 g (0.012 mol) cf imidazole sodium salt in 5 ml of dimethylformamide was warmed to 80-900 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 (CDC13) 0.4 (6H, s), 3.7 (2H, s), 6.7 (1H, broad s), 7.0 (1H, broad s), 7.1-7.8 (10H, m); analysis for C18H20N25i (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-imidazol1-ylmethyl)silane A mixture of 2.2 g (0.010 mol) of chloromethyl(4chlorophenyl)dimethylsilane 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 title compound as a yellow liquid: n,20 1.5472; ir (neat) 1560, 1495, 1480, 1375, 1250, 1105, 1080, 905, 830, 810, 740 cm 1; nmr (CDCl3) 0.3 (6H, s), 3.6 (2H, s), 6.6 (1H, broad s), 6.9 (1H, broad s), 7.1 (1H, broad s), 7.3 (4H, s). Example 39 Preparation of (2,4-Dichlorophenyl)dimethyl(lH- imidazol-1-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 title compound as a brown oil: nD23 1.5637; ir (neat) 1560, 1500, 1450, 1355, 1250, 1105, 1095, 1075, 1025, 840, 780, 735 cm 1; nmr (00013) 0.4 (6H, s), 3.9 (2H, s), 6.7 (1H, broad s), 7.0 (1H, broad s) 7.2-7.5 (4H, m). Example 40 Preparation of Diphenyl(lH-imidazol-l-ylmethyl) methylsilane A mixture of 4.9 g (0.020 mol) of chloromethyl (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 1250/0.05 mm removed volatile impurities, leaving behind 2.9 g (52%) of the title compound as an oil: nD22 1.5995; ir (neat) 3375, 3250, 1500, 1430, 1255, 1230, 1110, 1075, 1025, 810, 790, 735, 700, 660 cm 1; nmr (CDC13) 0.6 (3H, s), 3.9 (2H, s), 6.6 (1H, broad s), 6.9 (1H, broad s), 7.2-7.5 (llH, m). By applying the procedures of Example 37-40 to appropriate chloromethylsilanes, the compounds of Table XIV can be prepared. Table XIV EMI86.1 R1 R2 R3 CH3 CH3 CH3 nD22 1.4805 C2H5 CH3 CH3 nD22 1.4848 i-C3H7 CH3 CH3 n-C4H9 CH3 CH3 nD19 1.4811 t-C4Hg CH3 CH3 n-C12H25 CH3 CH3 nD23 1.4585 n-C14H29 CH3 CH3 n-C18H37 CH3 CH3 nD21 1.4639 cyclopropyl CH3 CH3 cyclobutyl CH3 CH3 cyclopentyl CH3 CH3 cyclohexyl CH3 CH3 nD22 1.4999 1-naphthyl CH3 CH3 nD23 1.6188 2-naphthyl CH3 CH3 phenyl CH3 CH3 bp 120-125 (0.05 mm) 4-bromophenyl CH3 CH3 nD20 1.5741 4-fluorophenyl CH3 CH3 nD23 1.5314 4-methoxyphenyl CH3 CH3 nD25 1.5485 4-phenoxyphenyl CH3 CH3 nD22 1.5833 4-(4-chlorophenoxy)phenyl CH3 CH3 nD22 1.5564 4-(4-fluorophenoxy)phenyl CH3 CH3 4-(4-trifluoromethylphenoxy)phenyl CH3 CH3 4-(4-methylphenoxy)phenyl CH3 CH3 Table XIV (continued) R1 R2 R3 4-thiomethylphenyl CH3 CH3 nD23 1.5855 D 21 4-methylsulfonylphenyl CH3 CH3 nD22 1.5552 4-trifluoromethylphenyl CH3 CH3 nD22 1.4867 4-methylphenyl CH3 CH3 nD21 1.5482 4-i-propylphenyl CH3 CH3 4-t-butylphenyl CH3 CH3 nD23 1.5229 4-cyclohexylphenyl CH3 CH3 nD22 1.5085 4-trifluoromethoxyphenyl CH3 CH3 nD22 1.4888 4-(4-chlorophenyl)phenyl CH3 CH3 4-84-methylphenyl)phenyl CH3 CH3 4-(4-trifluoromethylphenyl)phenyl CH3 CH3 4-c 4-fluorophenyl )phenyl CH3 CH3 4-(4-bromophenyl)phenyl CH3 CH3 nD22 1.5745 3-phenylphenyl CH3 CH3 nol 1.6002 3-trifluoromethylphenyl CH3 CH3 nD20 1.4927 3-chlorophenyl CH3 CH3 nD22 1.5560 2-trifluoromethylphenyl CH3 CH3 nD23 1.5065 2-phenylphenyl CH3 CH3 nD22 1.5996 2-chlorophenyl CH3 CH3 22 1.5382 no j.3B2 2-methoxyphenyl CH3 CH3 nD22 1.5344 2,3-dimethylphenyl CH3 CH3 2,3-dimethoxyphenyl CH3 CH3 nD22 1.5350 2,4-difluorophenyl CH3 CH3 2-fluoro-4-chlorophenyl CH3 CH3 2-chloro-4-fluorophenyl CH3 CH3 2-chloro-4-phenylphenyl CH3 CH3 3-chloro-4-phenylphenyl CH3 CH3 2-methyl-5-chlorophenyl CH3 CH3 Table XIV (continued) R1' R2 R3 2,6-dimethoxyphenyl CH3 CH3 nD23 1.5348 2,6-dimethylphenyl CH3 CH3 3,4-dichlorophenyl CH3 CH3 nD23 1.5673 3-methyl-4-fluorophenyl CH3 CH3 3,5-dichlorophenyl CH3 CH3 22 1.5461 no C2H5 C2H5 CH3 i-C3H7 cyclohexyl CH3 n-C4H9 n-C4H9 CH3 n-C10H21 cyclopropyl CH3 nD22 1.4710 n-C12H25 n-C3H7 CH3 n-C14H29 i-C3H7 CH3 n-C18H37 3-methylbutyl CH3 cyclopropyl n-C6H13 CH3 cyclopentyl cylopentyl CH3 cyclohexyl cyclohexyl CH3 1-naphthyl n-c4H9 CH3 1-naphthyl t-C4H9 CH3 2-naphthyl n-C5H11 CH3 phenyl n-C3H7 CH3 22 phenyl n-C4H9 CH3 nD22 1.5449 phenyl 1,1-dimethylpropyl CH3 phenyl n-C6H13 CH3 4-phenylphenyl C2H5 CH3 3 4-phenylphenyl n-C4H9 CH3 nD22 1.5880 4-bromophenyl i-C3H7 CH3 4-chlorophenyl n-C4H9 CH3 nD21 1.5415 4-fluorophenyl n-C4H9 CH3 nD22 1.5161 4-phenoxyphenyl t-C4H9 CH3 4-i-propylphenyl cyclopropyl CH3 4-t-butylphenyl i-C4H9 CH3 Table XIV (continued) R1' R2 R3 3-phenylphenyl i-C4H9 CH3 3-trifluoromethylphenyl s-C4H9 CH3 3-chlorophenyl n-C5H11 CH3 2-methoxyphenyl t-C4H9 CH3 2-thiomethylphenyl cyclobutyl CH3 2-phenylphenyl i-C4H9 CH3 n21 2,4-dichlorophenyl n-C4H9 CH3 nD21 1.5588 2,4-dichlorophenyl cyclopropyl CH3 2,3-dimethylphenyl n-C3H7 CH3 2-methyl-5-fluorophenyl cyclopentyl CH3 2, 5-dimethoxyphenyl 4-methylpentyl CH3 2,6-dimethylphenyl 1-methylbutyl CH3 3,4-dichlorophenyl n-C5H11 CH3 3,5-dichlorophenyl n-C4H9 CH3 3,5-dichlorophenyl cyclohexyl CH3 3-methyl-4-chlorophenyl cyclopropyl CH3 19 4-fluorophenyl phenyl CH3 19 5oiu 4-chlorophenyl phenyl CH3 21 U 4-bromophenyl phenyl CH3 nD22 1.6115 4-phenylphenyl phenyl CH3 21 1.6378 no 4-t-butylphenyl phenyl CH3 4-thiomethylphenyl phenyl CHs 4-phenoxyphenyl phenyl CH3 4-trifluoromethoxyphenyl phenyl CH3 4-methylsulfonylphenyl phenyl CH3 4-cyclohexylphenyl phenyl CH3 4-(4-fluorophenyl)phenyl phenyl CH3 3-trifluoromethylphenyl phenyl CH3 2-chlorophenyl phenyl CH3 nD22 1.6059 2-chlorophenyl phenyl CH3 Table XIV (continued) R1' R2 R3 2,4-dichlorophenyl phenyl CH3 n22 1.6150 0 2-chloro-4-phenylphenyl phenyl CH3 2-fluoro-4-phenylphenyl phenyl CH3 3,5-dichlorophenyl phenyl CH3 2,5-dimethoxyphenyl phenyl CH3 2,6-dimethoxyphenyl phenyl CH3 4-fluorophenyl 4-fluorophenyl CH3 no 1.5569 4-chlorophenyl 4-chlorophenyl CH3 no 1.5820 4-bromophenyl 4-bromophenyl CH3 nD21 1.6305 4-phenylphenyl 4-phenylphenyl CH3 m.p. 44-53 4-methoxyphenyl 4-methoxyphenyl CH3 nD21 1.5947 3-trifluoromethylphenyl 3-trifluoromethylphenyl CH3 2-chlorophenyl 2-chlorophenyl CH3 nD20 1.5999 2-methoxyphenyl 2-methoxyphenyl CH3 22 2,4-dichiorophenyl 2,4-dichlorophenyl CH3 no 1.6019 3,5-dichlorophenyl 3,5-dichlorophenyl CH3 2-chlorophenyl 4-chlorophenyl CH3 nD20 1.6044 2-chlorophenyl 4-fluorophenyl CH3 4-phenylphenyl 4-chlorophenyl CH3 4-phenylphenyl 4-fluorophenyl CH3 4-phenylphenyl 2,4-dichlorophenyl CH3 4-fluorophenyl 2, 4-dichlorophenyl CH3 4-chlorophenyl 2,4-dichlorophenyl CH3 1-naphthyl 2,6-dimethoxyphenyl CH3 4-phenoxyphenyl 3,4-dichlorphenyl CH3 C2H5 C2H5 C2H5 i-C3H7 i-C3H7 i-C3H7 n-C4H9 n-C4H9 n-C4H9 n-C8H17 C2H5 cyclopentyl n-C14H29 cyclopropyl l-methylbutyl Table XIV (continued) R1' R2 R3 n-C18H37 n-C6H13 n-C6H13 cyclopropyl C2H5 s-C4H9 cyclohexyl n-C3H7 n-C3H7 1-naphthyl n-C4H9 n-C4H9 2-naphthyl n-C4Hg cyclobutyl phenyl cyclopropyl n-C6H13 4-phenylphenyl C2H5 C2H5 4-phenylphenyl n-C4H9 n-C4Hg 4-phenylphenyl n-C6H13 n-C6H13 4-phenylphenyl cyclohexyl cyclohexyl 4-chlorophenyl n-C4H9 n-C4H9 4-fluorophenyl n-C3H7 n-C3H7 4-phenoxyphenyl n-C4Hg cyclohexyl 4-(4-chlorophenoxy)phenyl n-C4H9 n-C4H9 4-t-butylphenyl s-C4H9 i-C4H9 3-methoxyphenyl C2Hs <RTI ID=91.5> t-C4H9 3-trifluoromethylphenyl s-C4H9 s-C4H9 2-thiomethylphenyl i-C3H7 3-methylbuty 2-phenylphenyl cyclohexyl cyclohexyl 2,4-dichlorophenyl n-C4H9 n-C4H9 2,6-dimethylphenyl t-C4H9 t-C4H9 3,5-dichlorophenyl cyclopentyl cyclopentyl 3-methyl-4-chlorophenyl s-C4H9 s-C4H9 2-methyl-5-fluorophenyl n-C4H9 i-C4H9 C2H5 phenyl phenyl cyclohexyl phenyl phenyl n-C18H37 phenyl phenyl n-C4H9 4-chlorophenyl 4-chlorophenyl n-C12H25 4-chlorophenyl 4-chlorophenyl 1-naphthyl 4-fluorophenyl 4-fluorophenyl @@@@@@@@ol phenyl 4-methylphenyl n-C4H9 phenyl 4-methylphenyl Table XIV (continued) R1' R2 R3 t-C4Hg phenyl 2,4-dichlorophenyl n-C3H7 phenyl 3-trifluoromethylphenyl i-C4H9 phenyl 3,5-dicnlorophenyl cyclopentyl phenyl 2,6-dimethoxyphenyl n C14H29 4-chlorophenyl 2-fluorophenyl n-C4H9 4-fluorophenyl 4-phenylphenyl phenyl phenyl phenyl m.p. 175-1780 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-dichlorphenyl phenyl 4-fluorophenyl 4-fluorophenyl phenyl 4-chlorophenyl 4-chlorophenyl phenyl 4-phenylphenyl 4-phenylphenyl phenyl 2,4-dichlorophenyl 2,4-dichlorphenyl 2-naphthyl 4-methylthiophenyl 4-methylthiophenyl 4-chlorophenyl 2-meth oxyphenyl 2-methoxyphenyl 4-chlorophenyl 3-chlorophenyl 3-chlorophenyl phenyl 2-chlorophenyl 4-fluorophenyl phenyl 4-chlorophenyl 4-phenylphenyl l-naphthyl 4-bromophenyl 3-methylphenyl 4-phenoxyphenyl 3,5-dimethylphenyl 3,4-dichlorophenyl Example 41 Preparation of (l,l'-8iphenyl-4-yl)dimethyl(2-methyl- lH-imidazol-l-ylmethyl)silane The title compound is prepared by applying the procedure of Example 37 to (1,1'-biphenyl-4-yl)chloromethyidimethylsilane 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 EMI94.1 R1' R2 R3 Q1 Q2 Q3 O2H5 CH3 CH3 CH3 CH3 CH3 n-C18H37 CH3 CH3 H CH3 CH3 cyclohexyl CH3 CH3 H CH3 CH3 1-naphthyl CH3 CH3 CH3 H H phenyl CH3 CH3 H CH3 H phenyl CH3 CH3 H H CH3 4-phenylphenyl CH3 CH3 CH3 H H 4-(4-fluorophenyl)phenyl CH3 CH3 CH3 H H 4-phenoxyphenyl CH3 CH3 CH3 CH3 CH3 3-trifluoromethylphenyl CH3 CH3 H CH3 CH3 2-methoxyphenyl CH3 CH3 CH3 H H 2,4-diclorophenyl CH3 CH3 CH3 CH3 CH3 2-chloro-4-phenylphenyl CH3 CH3 H CH3 CH3 phenyl n-C4H9 CH3 CH3 H H 4-phenylphenyl n-C4H9 CH3 H CH3 CH3 2,4-dichlorophenyl n-C6H13 CH3 CH3 H H 4-(4-chlorophenoxy)phenoxy cyclohexyl CH3 CH3 H H phenyl phenyl CH3 CH3 CH3 CH3 4-fluorophenyl phenyl CH3 CH3 H H 4-fluorophenyl phenyl CH3 CH3 CH3 CH3 4-chlorophenyl phenyl CH3 H CH3 CH3 4-fluorophenyl 4-fluorophenyl CH3 CH3 H H' 4-fluorophenyl 4-fluorophenyl CH3 H CH3 CH3 4-fluorophenyl 4-chlorophenyl CH3 CH3 CH3 CH3 4-fluorophenyl 4-chlorophenyl Table XV (continued) R1' R2 R3 Q1 Q2 Q3 2-chlorophenyl 4-chlorsphenyl CH3 CH3 CH3 CH3 2,4-dichlorophenyl 2 4-dichlorophenyl CH3 CH3 H H n-C18H37 n-C6H13 n-C6H13 H CH3 CH3 1-naphthyl n-C4H9 n-C4H9 CH CH3 CH3 phenyl phenyl phenyl CH3 H H phenyl phenyl phenyl CH3 H CH3 phenyl phenyl phenyl CH3 CH3 H Example 42 Preparation of the 1: :1 complex of (l,l'-8iphenyl-4-yl)- dimethyl(1H-imidazol-1-ylmethyl)silane and Cuprous Chloride A mixture of 0.50 g (0.0017 mol) of (l,l'-bi- phenyl-4-yl)dimethyl(1H-imidazol-1-ylmethyl)silane 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 cm1. 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 (1,1-'Biphenyl-4-yl)(1H-imidazol1-ylmethyl)(methoxy)methylsilane A mixture of (l,l'-tiphenyl-4-yl)chloro(chloro- methyl)methylsilane 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 700 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 R6 = OH, water is used instead of an alcohol, and hydrolysis is conducted at 20-250 instead of 700. Example 44 Preparation of 1,1-(Dimethylethoxy)(1H-imidazol-1-yl methyl)methvl(ohenyl) silane A mixture of 3.6 9 (0.015 mol) of chloromethyl (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 500 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 900 (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, 0 3045, 2970, 1590, 1500, 1425, 1360, 1250, 1235, 1185, 1110; 1055, 1020, 900, 805, 740, 700, 660 cm-1; nmr (CDCl3): 0.6 (3H, s), 1.3 (9H, s), 3.6 (2H, s), 6.8 (1H, s), 7.0 (1H, s) and 7.3-7.7 (6H, m). The compounds of Tables XVI and XVII can be made using the procedures of Examples 43 and 44. Table'XVI EMI98.1 R1' R2 R6 C2H5 CH3 CH3 t-C4H9 CH3 t-C4H9 n-C4H9 CH3 C2H5 n-C12H25 C2H5 CH3 n-C18H37 n-C6H13 CH3 cyclopropyl CH3 s-C4H9 cyclohexyl CH3 CH3 1-naphthyl i-C3H7 i-C3H7 2-naphthyl cyclobutyl n-C3H7 phenyl CH3 H phenyl CH3 CH3 phenyl CH3 C2H5 phenyl Ch3 i-C3H7 nD20 1.5352 phenyl t-C4H9 H 4-phenylphenyl n-C4H9 CH3 4-phenylphenyl t-C4H9 H 4-phenylphenyl CH3 C2H5 4-phenylphenyl CH3 n-C4H9 4-chlorophenyl n-C4H9 n-C4H9 4-chlorophenyl CH3 CH3 4-chlorophenyl CH3 C2H5 4-fluorophenyl n-C6H13 n-C3H7 4-fluorophenyl CH3 C2Hs 4-phenoxyphenyl cyclohexyl i-C H 4-t-butylphenyl n-C3H7 s-C4H9 3-trifluoromethylphenyl t-C4H9 H 2-methylthiophenyl cyclopentyl C2H5 Table XVI (continued) Ri R2 R6 2,4-dichlorophenyl CH3 CH3 2,4-dichlorophenyl CH3 C2H5 2,4-dichlorophenyl CH3 t-C4H9 2,4-dichlorophenyl n-C4H9 C2H5 2,3-dimethylphenyl cyclopropyl i-C3H7 2-methyl-5-fluorophenyl s-C4H9 n-C3H7 2,6-dimethoxyphenyl 1,1-dimethylpropyl H 3-methyl-4-chlorophenyl C2H5 CH3 3,5-dichlorophenyl n-C5H11 C2H5 n-C12H25 2,4-dichlorophenyl t-C4H9 n-C18H37 phenyl CH3 1-naphthyl phenyl C2H5 phenyl phenyl t-C4H9 4-fluorophenyl phenyl CH3 4-chlorophenyl phenyl n-C3H7 4-phenylphenyl phenyl C2H5 4-phenylphenyl phenyl S-C4H9 4-t-butylphenyl phenyl s-C4H9 3-fluorophenyl phenyl C2H 2-methoxyphenyl phenyl H 2-chlorophenyl phenyl CH3 2,4-dichlorophenyl phenyl i-C3H7 3,4-dichlorophenyl phenyl n-C3H7 4-fluorophenyl 4-fluorophenyl t-C4Hg 4-fluorophenyl 4-fluorophenyl C2H5 4-chlorophenyl 4-chlorophenyl CH3 4-chlorophenyl 4-chlorophenyl C2H5 4-ohenylphenyl 4-phenylphenyl CH3 2,4-dichlorophenyl 2,4-dichlorophenyl C2H5 3-trifluoromethylphenyl 3-trifluoromethylphenyl i-C4H 2-methoxyphenyl 2-methoxyphenyl H 2-chlorophenyl 4-fluorophenyl H Table XVI (continued) R1' R2 R6 3-trifluoromethylphenyl 4-t-butylphenyl n-C4Hg 2-fluoro-4-chlorophenyl 4-bromophenyl i-C3H7 2,3-dimethylphenyl 4-methylthiophenyl 2,6-dimethoxyphenyl 4-methoxyphenyl H 3,4-dichlorophenyl 4-methylphenyl i-C4H9 Table XVII EMI101.1 R1' R2 R6 Q1 Q2 Q3 C2H5 CH3 CH3 CH3 CH3 CH3 cyclohexyl CH3 i-C3H7 H CH3 CH3 n-C18H37 n-C6H13 t-C4H9 CH3 H H l-naphthyl CH3 i-C3H7 CH3 H H phenyl CH3 t-C4H9 H CH3 H phenyl CH3 t-C4H9 H H CH3 phenyl CH3 t-C4H9 CH3 CH3 CH3 phenyl CH3 s-C4H9 H CH3 CH3 phenyl CH3 i-C4H9 CH3 H H 4-phenylphenyl n-C4H9 t-C4H9 CH3 CH3 CH3 4-phenylphenyl CH3 t-C4H9 CH3 H H 4-phenylphenyl CH3 t-C4H9 CH3 CH3 CH3 4-chlorophenyl CH3 t-C4H9 CH3 H H 4-chlorophenyl CH3 t-C4H9 H CH3 CH3 4-fluorophenyl CH3 t-C4H9 H CH3 H 4-fluorophenyl CH3 t-C4H9 H H CH3 phenyl phenyl C2H5 CH3 CH3 CH3 phenyl phenyl n-C3H7 CH3 CH3 CH3 4-fluorophenyl phenyl i-C3H7 H CH3 CH3 4-fluorophenyl phenyl t-C4H9 CH3 H H 4-chlorophenyl phenyl i-C3H7 CH3 H H 2,4-dichlorophenyl phenyl H CH3 H H 4-fluorophenyl 4-fluorophenyl t-C4H9 CH3 H H 4-fluorophenyl 4-fluorophenyl t-C4H9 H CH3 CH3 4-fluorophenyl 4-fluorophenyl t-C4H9 CH3 CH3 CH3 2-methoxyphenyl 2-methoxyphenyl C2H5 CH3 H H 3-methylphenyl 3-methylphenyl i-C4H9 CH3 H H Example 45 Preparation of (1H-imidazol-1-ylmethyl)phenylbis(2propoxy)silane The title compound can be made by applying the procedure of Example 26 to chloromethyl(phenyl)bis (2-propoxy)silane: nD22 1.4971; nmr (CDCl3) 1.2 (12H, d, J = 6), 3.6 (2H, s), 4.2 (2H, septet, J = 6), 6.8-7.6 (8H, m). The compounds of Tables XVIII and XIX can be made similarly. Table XVIII EMI103.1 RI' R6 Q1 Q2 Q3 C2H5 t-C4Hg H H H n-C4H9 C2H5 H H H n C18H37 CH3 H H H cyclohexyl n-C3H7 H H H 1-naphthyl i-C4H9 H H H phenyl CH3 CH3 CH3 CH3 phenyl n-C3H7 CH3 H H phenyl i-C3H7 H CH3 CH3 phenyl t-C4Hg H H H 4-phenylphenyl C2H5 H H H 4-phenylphenyl n-C4Hg CH3 CH3 CH3 4-fluorophenyl CH3 CH3 H H 4-fluorophenyl O2H5 H H H 4-chlorophenyl O2H5 H H H 4-chlorophenyl i-C3H7 H H H 3-trifluoromethylphenyl s-C4H9 CH3 CH3 CH3 2-methoxyphenyl n-C3H7 CH3 H H 2,3-dimethylphenyl i-C4H9 H H H 2,4-dichlorophenyl CH3 H H H 2,4-dichlcrophenyl C 2H5 H H H 2-methoxy-5-fluorophenyl i-C3H7 H H H 2,6-dimethoxyphenyl CH3 H H H 3,4-dichlorophenyl C2H5 H H H 3,5-dichlorophenyl n-C4Hg H H H Table XIX EMI104.1 EMI104.2 <tb> RI <SEP> R; <SEP> Q1 <SEP> Q2 <SEP> Q3 <tb> CfflS <SEP> -CHH2- <SEP> H <SEP> H <SEP> H <tb> <SEP> OH3 <tb> fl-C <SEP> 4H9 <SEP> -CH2OH- <SEP> CH3 <SEP> H <SEP> H <tb> n-C18H37 <SEP> -CH2CH2CH2- <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> C,2H5 <tb> cyclohexyl <SEP> -CH2CH <SEP> CH3 <SEP> CH3 <SEP> CH3 <tb> l-naphthyl <SEP> -CH2CH2- <SEP> CH3 <SEP> H <SEP> H <tb> phenyl <SEP> CH2CH2 <SEP> H <SEP> H <SEP> H <tb> <SEP> C2Hs <tb> phenyl <SEP> -CH2CH- <SEP> H <SEP> H <SEP> H <tb> <SEP> ¯ <SEP> ,3 <SEP> 7 <tb> phenyl <SEP> -CH2CH- <SEP> H <SEP> H <SEP> H <tb> phenyl <SEP> -CtCH3)2C(CH3)2- <SEP> H <SEP> H <SEP> H <tb> 4-phenylphenyl <SEP> -CH2CH2- <SEP> H <SEP> H <SEP> H <tb> <SEP> OH <SEP> 3 <tb> 4-phenylphenyl <SEP> -CH2CH- <SEP> H <SEP> H <SEP> H <tb> <SEP> OH,3O,H3 <tb> 4-phenylphenyl <SEP> -CHL-CH- <SEP> H <SEP> H <SEP> H <tb> 4-fluorophenyl <SEP> CH2CH2 <SEP> H <SEP> H <SEP> H <tb> <SEP> ,CH3 <tb> 4-fluorophenyl <SEP> -CH2CH- <SEP> H <SEP> H <SEP> H <tb> <SEP> C'2H5 <tb> 4-chlorophenyl <SEP> -CH2CH- <SEP> H <SEP> H <SEP> H <tb> 4-chlorophenyl <SEP> -C(CH <SEP> 3) <SEP> 2O(CH3)2- <SEP> H <SEP> H <SEP> H <tb> <SEP> C,H3 <tb> 3-trifluoromethylphenyl <SEP> OHOH2O(CH3)2 <SEP> CH¯ <SEP> OH <SEP> CH3 <tb> Table XIX (continued) EMI105.1 <tb> Rf <SEP> R6 <SEP> Qr <SEP> Q2 <SEP> Q3 <tb> <SEP> 1 <SEP> 6 <tb> <SEP> -n-C's', <tb> 2-methoxyphenyl <SEP> -CH2CH- <SEP> CH3 <SEP> H <SEP> H <tb> 2,3-dimethylphenyl <SEP> - <SEP> -CH <SEP> i <SEP> H <SEP> r <SEP> H <SEP> CH <SEP> CHm <tb> <SEP> OH <tb> 2,4-dichlorophenyl <SEP> -CH2CH- <SEP> H <SEP> H <SEP> H <tb> <SEP> n-C,?'7 <tb> 2,4-dichlorophenyl <SEP> -CH2CH- <SEP> H <SEP> H <SEP> H <tb> <SEP> CH3 <SEP> C,H3 <tb> <SEP> 13 <SEP> 13 <tb> 2-methoxy-5-fluorophenyl <SEP> -CHC(CH3)2CH- <SEP> C <SEP> 3 <SEP> H <SEP> H <tb> 2,6-dimethoxyphenyl <SEP> -CH2CH2- <SEP> H <SEP> H <SEP> H <tb> <SEP> CH3 <SEP> CH3 <tb> 3 <SEP> ,4-dichlorophenyl <SEP> -CHCH2CH- <SEP> CH3 <SEP> CH3 <SEP> CH3 <tb> <SEP> CH3 <SEP> C, <SEP> H3 <tb> 3,5-dichlorophenyl <SEP> -CH <SEP> - <SEP> CH- <SEP> CH3 <SEP> CH3 <SEP> CH3 <tb> C2Hs <SEP> -CH2CH=CHCH2- <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> OH,3 <SEP> OH,3 <tb> n-C18H37 <SEP> CHCH2CH2CH <SEP> H <SEP> CH3 <SEP> CH3 <tb> phenyl <SEP> -CH2CH=CHCH2- <SEP> H <SEP> H <SEP> H <tb> phenyl <SEP> -( <SEP> -O(O)2OH=CHC(CH3)2 <SEP> H <SEP> H <SEP> H <tb> <SEP> CH3 <SEP> CH3 <tb> phenyl <SEP> CHCH2CH2CY- <SEP> H <SEP> H <SEP> H <tb> phenyl <SEP> -C(CH3)2CH2 <SEP> H2C(CH3)2 <SEP> H <SEP> H <SEP> H <tb> 4-phenylphenyl <SEP> -CH2CH=CHCH2- <SEP> H <SEP> H <SEP> H <tb> <SEP> OH,3C,H3 <tb> 4-phenylphenyl <SEP> -CH <SEP> -CH2C===CCH2- <SEP> CH <SEP> - <SEP> H <SEP> H <SEP> H <tb> 4-fluorophenyl <SEP> -CH2-CH=CHCH2- <SEP> H <SEP> H <SEP> H <tb> 4-chlorophenyl <SEP> -CH2CH2CH2CH2- <SEP> H <SEP> H <SEP> H <tb> <SEP> n-Cs', <tb> 4-phenoxyphenyl <SEP> CH2CH2CH2CH <SEP> CH3 <SEP> H <SEP> H <tb> <SEP> CH3 <SEP> CH3 <tb> <SEP> 13 <SEP> 13 <tb> 3-trifluoromethylphenyl <SEP> -CHCH=CHCH- <SEP> H <SEP> CH3 <SEP> CH3 <tb> <SEP> CH3 <SEP> C,H3 <tb> 2-methoxyphenyl <SEP> -OH2CH-CHCH2- <SEP> CH3 <SEP> CH3 <SEP> CH3 <tb> 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 20S surfactant(s) and b) about 5% to 999S solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: : Percent by Weight Active Ingredient Oiluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 5-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable Concentrates) 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. 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, 1956. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0 C. "MeGutcheon"s Detergents and Emulsifiers Annual11, 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. Example 46 Wettable Powder (1,1-Biphenyl-4-yl)dimethyl(1H-1,2,4-triazol-1-yl methyl)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. Example 47 Wettable Powder (4-8romOphenyl)dimethyl(1H-1,2,4-triazol-1-ylmethyl)- silane 20 < sodium alkylnaphthlenesulfonate 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-1,2,4-triazol-1-yl- methyl)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 49 Oust high strength concentrate from Example 48 25.4% pyrophyllite, powdered 74.6% The ingredients are thoroughly blended and packaged for use. Example 30 Aqueous Suspension (l,lt-Biphenyl-4-yl)dimethyl(lH-1,2,4-triazol-1-yl- methyl)silane 50.0% polyacrylic acid thickener 0.3% dodecylphenyl polyethylene glycol ether 0.3% 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. Examole 51 Emulsifiable Concentrate Oimethyl(phenyl)(lH-1,2,4-triazol-1-ylmethyl)- silane 20% chlorobenzene 74% sorbitan monostearate and poly oxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. Example 52 Emulsifiable Concentrate Oimethyl(4-methylphenyl)(lH-1,2,4-triazol-1-ylmethyl) silane 30% blend of oil soluble sulfonates and polyoxyethylene ethers 4% xylene 66t 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 an to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 mm. (U.S.S. it 18 to 46 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-Oichlorophenyl)dimethyl(lH-1,2,4-triazol-l-yI- methyl)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 includes in packaging operate to insure the absence of any extraneous undissolved material in the product. Example 55 Emulsifiable Concentrate Butyl(4-chlorophenyl)methyl(lH-1,2,4-triazol-1-yl- methyl)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 56 Emulsifiable Concentrate bis(4-Ohlorophenyl)methyl(lH-l,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 57 Emulsifiable Concentrate bis(4-Fluorophenyl)methyl(lH-1,2,4-triazol-1-ylmethyl) silane 20% chlorobenzene 74% sorbitan monostearate and poly oxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. Example 58 Emulsifiable Concentrate 4-FluorophenyL(methyl)phenyl(lH-1,2,4-triazal-1-yl- methyl)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 Cl,l'-Biphenyl-4-yl)dimethyl(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 Pawder (l,L-8iphenyl-4-yl)dimethyl(lH-imidazol-l-ylmethyl)- silane 40% dioctyl sodium sulfosuccinate 1.5% sodium ligninsulfonate 3 < low viscosity methyl cellulose 1.526 attapulgite 54% The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, blended, 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 61 Emulsifiable Concentrate (1,1'-8iphenyl-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 filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product. Example 62 Emulsifiable Concentrate (1,1'-Biphenyl-4-yl)dimethyl(1H-imidazol-1-ylmethyl) silane 20% chlorobenzene 74% sorbitan monostearate and poly oxy.ethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. Examole 63 Aqueous Suspension (l,l'-ssiphenyl-4-yl)dimethyl(lH-imidazol-l-ylmethyl)- silane 25% hydrated attapulgite 3% crude calcium ligninsulfonate 10% sodium dihydrogen phosphate 0.5 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. Example 64 High Strength Concentrate (1,1'-8iphenyl-4-yl)dimethyl(lH-imidazol-l-yl.methyl)- 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 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. &num; 18 to 40 sieves), the granules are removed, dried1 and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain active ingredient. Examole 66 Oust high strength concentrate from Example 64 25.4 < pyrophyllite, powdered 74.6% The ingredients are thoroughly blended and packaged for use. Example 67 Emulsifiable Concentrate 4-Chlorophenylmethyl)phenyl(lH-imidazol-l-yl- methyl)silane 20% chlorobenzene 74% sorbitan monostearate and poly oxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified In water for application. 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 cichoracearum, Erysiphe araminis, Venturia inaegualis, Helminthosporium maydis, CFrco- spora arachidicola, blromvces phase and Monilinia fructicola, Rhizoctonia solani, Pyricularia oryzae, Phytophthora infestans and other Phytophthora species. They also control seed pathogens such as Pythium 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 fom 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. 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 are well-known to those skilled in the art. Some are listed below: Fungicides: methyl 2-benzimidazolecarbamate (carbendazim) tetramethylthiuram disulfide (thiuram) n-dodecylguanidine acetate (dodine) manganese ethylenebisdithiocarbamate (maneb) 1,4-dichloro-2,5-dimethoxybenzene (chloroneb) methyl l-(butylcarbamoyl)-2-benzimidazolecarbamate (benomyl) 2-cyano-N-ethylcarbamoyl-2-methoxyimincacetamide (cymoxanil) N-trichloromethylthiotetrahydrophthal.imide (captan) N-trichloromethylthiophthalimide (folpet) dimethyl 4,4'-(o-phenylene)bis(3-thioallophanate) (.thiophanate-methyl) 2-(thiazol-4-yl)benzimidazole (thiabendazole) aluminum tris(O-ethyl phosphonate) ("Aliette") tetrachloroisophthalonirile (chlorothalonil) 2,6-dichloro-4-nitroaniline <RTI ID=117.6> (dichloran) N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine methyl ester (metalaxyl) cis-N-[(1,1,2,2-tetrachloroethyl)thio]cyclohex-4-ene 1,2-dicarbioximide (captafol) 3-(3,5-dichlorophenyl)-N-(l-methylethyl)-2, 4-dioxo-l- imidazolidine carboxamide (iprodione) 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-axazoli dinedione (vinclozolin) kasugamycin O-ethyl-S,S-diphenylphosphorodithioate (edifenphos) Bactericides: tribasic copper sulfate streptomycin sulfate oxytetracycline Acaricides: senecioic acid, ester with 2-sec-butyl-4,6-dinitro phenol (binapacryl) 6-methyl-1,3-dithioloC2,3-8]quinonolin-2-ane (oxythisquinox) 2,2,2-trichloro-l,l-bis(4-chlorophenyl)ethanol (dicofol) bs(pentachloro-2,4-cyclopentadien-l-yl) (dienochlor) tricyclohexyltin hydroxide (cyhexatin) hexakis(2-methyl-2-phenylpropyl)distannoxane (fenbutin oxide) Nematicides: 2-[diethoxyphosphinylimino]-1,3-dithietane (fosthietan) S-methyl-l-(dimethylcarbamoyl)-N-(methylcarbamoyloxy) thioformimidate (oxamyl) S-methyl-l-carbamoyl-N-(methylcarbamoyloxy)thioformi midate N-isopropylphosphoramidic acid, O-ethyl-O'-C4-(methyl thio)-m-tolyl]diester (fenamiphos) Insecticides: 3-hydroxy-N-methylcrotonamide(dimethylphosphate)ester (monocrotophos) methylcarbamic acid, ester with 2,3-dihydro-2,2-di methyl-7-benzofuranol (carbofuran) O-C2,4,5-trichloro-c-(chLoromethyl)benzyl]phosphoric acid, O',O'-dimethyl ester (tetrachlorvinphos) 2-mercaptosuccinic acid, diethyl ester, S-ester with thionophosphoric acid, dimethyl ester (malathion) phosphorothioic acid, 0,0-dimethyl, O-o-nitrophenyl ester (methyl parathion) methylcarbamic acid, ester with &alpha; ;-naphthol (carbaryl) methyl N-[[(methylamino)carbonyl]oxy]ethyanimidothioate (methomyl) N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine (chlordimeform) û,O-diethyl-0-(2-isopropyl-4-methyl-6-pyrimidyl)phos- phorothioate (diazinon) octachlorocamphene (toxaphene) O-ethyl O-p-nitrophenyl phenylphosphonothioate (EPN) cyano(3-phenoxyphenyl)-methyl 4-chloro-&alpha; ;-(1-methyl- ethyl)benzeneacetate (fenvalerate) (3-phenoxyphenyl)methyl (+)-cis,trans-3-(2,2-dichloro- ethenyl)-2,2-dimethylcyclopropanecarboxylate (permethrin) dimethyl N,N'-[thiobis](N-methylimino)carbonyloxy]] bis(ethanimidothioate) (thiodicarb) phosphorothiolothionic acid, O-ethyl-O-C4-(methylthio)- phenyl)-S-n-propyl ester (sulprofos) a-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2 dimethylcyclopropane carboxylate (cypermethrin) cyano(3-phenoxyphenyl)methyl 4-(difluoromethoxy)- (methylethyl)benzeneacetate ("Payoff1,) 0,0-diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphoro- thioate (chlorpyrifos) O,O-dimethyl-S-[(4-oxo-1,2,3-benzotriazin-3-(4H)-yl) <RTI ID=119.14> methyl)phosphorodithioate (azinphos-methyl) 5,6-dimethyl-2-dimethylamino-4-pyrimidinyl dimethyl carbamate ("Pirimor") S-(N-formyl-N-methylcarbemoylmethyl)-O,O-dimethyl phosphorodithioate (formothion) S-2-(ethylthioethyl)-O,O-dimethyl phosphiorothioate (demeton-S-methyl) c'-cyano-3-phenoxybenzyl cis-3-(2,2-dibromovinyl)-2,2 dimethylcyclopropane carboxylate (deltamethrin) cyano(3-phenoxyphenyl)methyl ester of N-(2-chloro-4 trifluoromethylphenyl)alanine ('1Mavrik") 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 230 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. tritici, causal agent of wheat leaf rust, and incubated in a saturated humidity chamber at 200 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 Comoound < Control Wheat Rust (Dimethyl)phenyl(1,2,4-triazol-I ylmethyl)silane 90 (4-8romophenyl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane 80 (1,1'-8iphenyl-4-yl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane 100 (4-Chlorophenyl)dimet-hyl(lH-1,2,4- triazol-I-ylmethyl)silane 100 Butyl(4-chlorophenyl)methyl(lH 1,2,4-triazol-l-ylmethyl)silane 80 (3,4-Oichlorophenyl)dimethyl(lH- l,2,4-triazol-l-ylmethyl)silane 60 Table 1 (continued) Compound 96 Control Wheat Rust (2,4-Dichlorophenyl)dimethyl(lH l,2,4-triazol-l-ylmethyl)silane 90 bis(4-Chlorophenyl)(methyl)(1H <RTI ID=121.3> l,2,4-triazol-l-ylmethyl)silane 90 Dimethyl(4-fluorphenyl)(1H-1,2,4 triazol-l-ylmethyl)silane 100 C4-(l,l-OimethylethyI)phenylldi- methyl(lH-1,2,4-triazol-l-yl- methyl)silane gA Butyl(2,4-dichlorophenyl)methyl(lH 1,2,4-triazol-1-ylmethyl)silane 100 bis(2,4-0ichlorophenyl)(methyl)(lH- 1,2,4-triazol-l-ylmethyl)silane 100 (2,4-Oichlorophenyl)methyl(phenyl)- (1H-1,2,4-triazol-1-ylmethyl)silane 100 (4-Chlorophenyl)methyl(phenyl)(lH l,2,4-triazol-l-ylmethyl)silane 100 (4-Fluorophenyl)methyl(phenyl)(lH 1,2,4-triazol-l-ylmethyl)silane 90 Oodecyl(dimethyl)(lH-1,2,4-triazol- 1-ylmethyl)silane 100A [4-(4-Chlorophenoxy)phenyl]dimethyl (1H-1,2,4-triazol-1-ylmethyl)silane 90 <RTI ID=121.10> (3,5-Oichlorophenyl)dimethyl(lH- 1,2,4-triazol-1-ylmethyl)silane 80 (1,1'-Biphenyl-4-yl)butyl(methyl) (1H-1,2,4-triazol-1-ylmethyl)silane 90 bis(l,l'-8iphenyl-4-yl)(methyl)(lH l,2,4-triazol-1-ylmethyl)silane 80 (l,l'-8iphenyl-4-yl)methyl(phenyl)- (lH-1,2,4-triazol-1-ylmethyl)silane 100 (l,l'-8iphenyl-3-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane 80 Table (continued) Compound X Control Wheat Rust 2-Chlorophenyl(methyI)phenyl(lH-1,2,4- triazol-l-ylmethyl)silane 80 [bis(2-Chlorophenyl)]methyl(1H-1,2,4 triazol-1-ylmethyl)silane 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-l-ylmethyl)silane, 4-dodecyl benzenesulfonic acid salt lOO (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 . triazol-l-ylmethyl)silane, 1:1 com plex with zinc (II) chloride 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-l-ylmethyl)silane, 1:1 com plex with manganous sulfate 90 2-Chlorophenyl( 4-chlorophenyl)methyl- (1H-1,2,4-triazol-1-ylmethyl)silane 100 Cbis(2-Fluoropenyl)]metyl(lH- 1,2,4-triazol-1-ylmethyl)silane, 1:1 complex with cuprous chloride 90 Cbis(2-Fluorophenyl)Imethyl(lH- 1,2,4-triazol-1-ylmethyl)silane, 2: :1 complex with cupric chloride 100 (1,1'-8iphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 100 (4-Chlorophenyl)(lH-imidazol-l ylmethyl)dimethylsilane 50 Butyl(4-chlorophenyl) (lH-imidazol- l-ylmethyl)methylsilane 90 (lH-Imidazol-l-ylmethyl)dimethyl- (4-phenoxyphenyl)silane 60 Oimethyl(lH-imidazol-l-ylmethyl) (4-methoxyphenyl)silane 60 (2,4-Dichlorophenyl)dimethyl(lH imidavol-l-ylmethyl)silane 90 Table I (continued) Compound 96 Control Wheat Rust bis(4-Fluorophenyl) (lH-imidazol-l- ylmethyl)methylsilane 100 Dimethyl(4-fluorophenyl)(lH-imida zol-l-ylmethyl)silane 80 Dimethyl(lH-imidazol-l-ylmethyl) (4-trifluoromethylphenyl)silane <RTI ID=123.4> locA Butyl(2,4-dichlorophenyl)(1H-imida zol-l-ylmethyl)methylsilane 100 bis(2,4-Dichlorophenyl) (lH-imidazol- l-ylmethyl)methylsilane 100 2,4-Oichlorophenyl(lH-imidazol-l- ylmethyl)methyl(phenyl)silane 90 4-Chlorophenyl(lH-imidazol-l-yl- methyl)methyl(phenyl)silane 100 Dodecyl(dimethyl)(lH-imidazol-l ylmethyl)silane (4-(4-Chlorophenoxy)phenyl]dimethyl- (lH-imidazol-l-ylmethyl)silane 90 Butyl(lH-imidazol-l-ylmethyl) methyl(phenyl)silane 90 (l,l'-8iphenyl-4-yl)butyl(lH-imida- zol-l-ylmethyl)methylsilane 100 (l,1'-Biphenyl-4-yl) (lH-imidazol- l-ylmethyl)methyl(phenyl)silane 100 (l,1'-Siphenyl-3-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 90 (4-Bromophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 90 (l,l'-8iphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 (2-Chlorophenyl)(4-chlorophenyl)(lH imidazol-l-ylmethyl)methylsilane 100 Table i (continued) Compound ¯ Control Wheat Rust (2-Chlorophenyl)(dimethyl)(lH-imi dazol-l-ylmethyl)silane 80 A Compound applied at a concentration of 200 ppm. 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 eucumber seedlings. The following day, the plants were inoculated with a spore suspension of the fungus Erysiphe cichoracearum, causal agent of cucumber 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. Phytotoxicity in the form of growth reduction or hormonal effects was observed on some of the plants in association with disease control. Table 2 % Control Cucumber Compound Powdery Mildew (Dimethyl) phenyl (1,2, 4-triazol-l- ylmethyl ) silane 100 Ethyldimethyl(lH-1,2,4-triazol-l ylmethyl)silane 100 Butyldimethyl(lH-1,2,4-triazol-l ylmethyl)silane 100 Oimethyl(4-methylphenyl)(lH-1,2,4- triazol-l-ylmethyl)silane lOOGA (4-8romophenyl)dimethyl(lH-1,2,4 triazol-l-ylmethyl)silane lOOG Table 2 (continued) % Control Cucumber Compound Powdery Mildew (l,l'-Biphenyl-4-yl)dimethyl(lH 1,2,4-triazol-1-ylmethyl)silane 100 (4-Chlorophenyl)dimethyl(lH-1,2,4- triazoI-l-ylmethyl)silane 100 Butyl(4-chlorophenyl)methyl(1H 1,2,4-triazol-1-ylmethyl)silane 1000 Dimethyl(l-naphthalenyl)(lH-1,2,4- triazol-l-ylmethyl)silane 100 (3,4-Dichlorophenyl)dimethyl(1H 1,2,4-triazol-1-ylmethyl)silane 100 Dimethyl(4-phenoxyphenyl)(1H-1,2,4 triazol-1-ylmethyl)silane 70 Dimethyl(4-methozxyphenyl)(1H-1,2,4 triazol-l-ylmethyl)silane 100 (2,4-Dichlorophenyl)dimethyl(lH- 1,2,4-triazol-1-ylmethyl)silane 100H8 bis(4-Chlorophenyl)(methyl)(lH 1,2,4-triazol-l-ylmethyl)silane 100 (lH-1,2,4-Triazol-l-ylmethyl)tri- phenylsilane 100 Methyldiphenyl(1H-1,2,4-triazol-1 ylmethyl)silane 100G (l,l'-8iphenyl-4-yl)dimethyl(4H- 1,2,4-triazol-4-ylmethyl)silane 90 bis(4-Fluorophenyl) (methyl) (lH- 1,2,4-triazol-l-ylmethyl)silane lOOG Oimethyl(4-fluorophenyl)(lH-1,2,4- triazol-l-ylmethyl)silane lOOG Oimethyl(4-methylthiophenyl)(lH 1,2,4-triazol-l-ylmethyl)silane 100 Table 2 (continued) % Control Cucumber Compound Powdery Mildew Dimethyl(lH-l,2,4-triazol-l-yl- methyl) (4-trifluoromethylphenyl)- silane 100G Dimethyl(lH-1,2,4-triaral-l-yl- methyl)(3-trifluoromethylphenyl)- silane Dimethyl(1H-1,2,4-triazol-1-yl methyl)(2-trifluoromethylphenyl) silane 100 (2-Methoxyphenyl)dimethyl(lH-1,2,4 triazol-l-ylmethyl)silane lOOG Butyl(2,4-dichlorophenyl)methyl)(1H 1,2,4-triazol-l-ylmethyl)silane lOOG bis(2,4-Dichlorophenyl)(methyl)(1H 1,2,4-triazol-l-ylmethyl)silane lOOG (2,4-Oichlorophenyl)methyl(phenyl) (1H-1,2,4-triazol-1-ylmethyl)silane 100G (4-Chlorophenyl)methyl(phenyl)(lH l,2,4-triazol-l-ylmethyl)silane lOOG (4-Fluorophenyl)methyl(phenyl)(1H 1,2,4-triazol-l-ylmethyl)silane 100 Butyl(methyl)phenyl(1H-1,2,4-triazol l-ylmethyl)silane 100 (2,3-Oimethoxyphenyl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane lOOG (2,6-Dimethoxyphenyl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane lOOG Dodecyl(dimethyl)(lH-1,2,4-triazol l-ylmethyl)silane 60C (2-Chlorophenyl)dimethyl(lH-1,2,4 triazol-l-ylmethyl)silane lOOG [4-(4-Chlorophenoxy)phenyl]dimethyl (1H-1,2,4-triazol-1-ylmethyl)silane 80 Table 2 (continued) % Control Cucumber Compound -Powdery Mildew (1,1'-Biphenyl-4-yl)butyl(methyl) (1H-1,2,4-triazol-1-ylmethyl)silane 100 Butyl (4-fluorophenyl)methyl(1H-1,2,4 triazol-1-ylmethyl)silane 100 bis(1,1'-Biphenyl-4-yl)(methyl)(1H l,2,4-triazol-l-ylmethyl)silane 100 (l,l'-8iphenyl-4-yl)methyl(phenyl)- (1H-1,2,4-triazol-1-ylmethyl)silane 100 (l,l-Dimethylethoxy)methyl(phenyl) (1H-1,2,4-triazol-1-ylmethyl)silane 100 Methyl(phenyl)(2-propoxy)(1H-1,2,4 triazol-l-ylmethyl)silane 100 (1,1'-Biphenyl-2-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane 90 2-Chlorophenyl(methyl)phenyl(1H-1,2,4 triazol-1-ylmethyl)silane 100 4-Bromophenyl(methyl)phenyl(1H-1,2,4 triazol-1-ylmethyl)silane 100 [bis(2-Chlorophenyl)]methyl(1H-1,2,4 triazol-1-ylmethyl)silane 100 Cyclohexyl(dimethyl)(lH-1,2,4-triazol- l-ylmethyl) silane lOOG Cbis(4-Bromophenyl)lmethyl(lH-1,2,4- triazol-l-ylmethyl)silane 80G (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane, 4-dodecyl benzenesulfonic acid salt 100 (1,1'-8iphenyl-4-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane, 1: :1 com plex with cuprous chloride 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane, 1:1 com plex with zinc (II) chloride 80 Table 2 (continued) % Control Cucumber Compound Powdery Mildew (l,l'-Biphenyl-4-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane, 1:1 com plex with manganous sulfate 90 2-Chlorophenyl(4-chlorophenyl)methyl (1H-1,2,4-triazol-1-ylmethyl)silane 100 Phenyl[bis(2-propoxy)](1H-1,2,4 triazol-l-ylmethyl)silane 100 Cbis(2-Fluorophenyl)]methyl(lH- 1,2,4-triazol-1-ylmethyl)silane, 1:1 complex with cuprous chloride 100 [bis(2-Fluorophenyl)]methyl(1H 1,2,4-triazol-1-ylmethyl)silane, 2: :1 complex with cupric chloride 100 Oimethyl(lH-imidazol-l-ylmethyl) phenylsilane 100 Ethyl ( lH-imidazol-l-ylmethyl ) - dimethylsilane 100 Butyl(lH-imidazol-l-ylmethyl)- dimethylsilane 100 (lH-Imidazol-l-ylmethyl)dimethyl- (4-methylphenyl)silane silane (4-Bromophenyl)(lH-imidazol-l-yl methyl)dimethylsilane 100 (l,l'-Biphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 100 (4-Chlorophenyl) (lH-imidazol-l- ylmethyl)dimethylsilane 100 Butyl(4-chlorophenyl)(1H-imidazol l-ylmethyl)methylsilane lOOG (lH-Imidazol-l-ylmethyl)dimethyl (l-naphthalenyl)silane 100 Table 2 (continued) % Control Cucumber Compound Powdery Mildew (3,4-Dichlorophenyl)(1H-imidazol l-ylmethyl)dimethylsilane 100 (1H-Imidazol-1-ylmethyl)dimethyl (4-phenoxyphenyl)silane 100 Oimethyl(lH-imidazol-l-ylmethyl)- (4-methoxyphenyl)silane 100 (2,4-0ichlorophenyl)dimethyl(lH- imidazol-l-ylmethyl)silane silane bis(4-Chlorophenyl)(1H-imidazol-1 ylmethyl)methylsilane 100 (lH-Imidazol-l-ylmethyl) triphenyl- silane 100 Diphenyl(lH-imidazol-l-ylmethyl)- methylsilane 100 bis(4-Fluorophenyl)(1H-imidazol-1 ylmethyl)methylsilane 100 Dimethyl(4-fluorophenyl)(1H-imida zol-l-ylmethyl)silane lOOG Dimethyl(lH-imidazol-l-ylmethyl) (4-methylthiophenyi)silane 100 Oimethyl(lH-imidazol-l-ylmethyl) (4-trifluoromethylphenyl)silane 100 Dimethyl(1H-imidazol-1-ylmethyl) (3-trifluoromethylphenyl)silane 80 [4-(1,1-Dimethylethyl)phenyl](1H imidazol-1-ylmethyl)dimethylsilane 80 (lH-Imidazol-l-ylmethyl)dimethyl (2-trifluoromethylphenyl)silane lOOG Butyl(2,4-dichlorophenyl)(1H-imida zol-l-ylmethyl)methylsilane Table 2 (continued) % Control Cucumber Compound ¯ Powdery Mildew bis(2,4-Dichlorophenyl)(1H-imidazol l-ylmethyl)methylsilane 100 (2,4-Dichlorophenyl)(1H-imidazol-1 ylmethyl)methyl(phenyl)silane 100 (4-Chlorophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 100 (4-Fluorophenyl) (lH-imidazol-l-yl- methyl)methyl(phenyl)silane 100 (lH-Imidazol-l-ylmethyl) (2-methoxy- phenyl)dimethylsilane lOOG (2,3-Dimethoxyphenyl)(1H-imidazol l-ylmethyl)dimethylsilane 100 Dodecyl(dimethyl)(lH-imidazol-l ylmethyl)silane 55 (2-Chlorophenyl)(lH-imidazol-l-yl methyl)dimethylsilane 100 [4-(4-Chlorophenoxy)phenyl]dimethyl (lH.imidazol-l-ylmethyl)silane 100 Butyl(lH-imidazol-l-ylmethyl) - methyl (phenyl) silane 100 (l,l'-8iphenyl-4-yl)butyl(lH-imida- zol-l-ylmethyl)methylsilane 100 Butyl(4-fluorophenyl) (lH-imidazol- l-ylmethyl)methylsilane 100 Oibutyl(lH-imidazol-l-ylmethyl)- methylsilane 100 (1,1'-Biphenyl-4-yl)(1H-imidazol 1-ylmethyl)methyl(phenyl)silane 100 (1,1-Dimethylethoxy)(1H-imidazl-1 ylmethyl)methyl(phenyl)silane 100 Table 2 (continued) % Control Cucumber Compound Powdery Mildew (lH-Imidazol-l-ylmethyl)methyl (phenyl)(2-propoxy)s-ilane 90 (1H-Imidazol-1-ylmethyl)[bis(4 methoxyphenyl) )methylsilane 50 (1,1'-Biphenyl-2-yl)dimethyl(1H imidazol-l-ylmethyl)silane 50 (2-Chlorophenyl)(1H-imidazol-1-yl methyl)methyl(phenyl)silane 100 (4-Bromophenyl)(1H-imidazol-1-yl methyl)methyl(phenyl)silane 100 Cbis(2-Chlorophenyl)](lH-imidazol- l-ylmethyl)methylsilane 100 Cyclohexyl(dimethyl(lH-imidazol-l- ylmethyl)silane 100Q [bis(4-Bromophenyl)](1H-imidazol-1 ylmethyl)methylsilane 100 (1,1'-8iphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride lOû (2-Chlorophenyl)(4-chlorophenyl)(lH imidazol-l-ylmethyl)methylsilane 100 (2-Chlorophenyl)(dimethyl)(lH-imi dazol-l-ylmethyl)silane 80 AG = growth reduction; and 8H = hormonal effects. 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 % Control Barley Compound Powdery Mildew Butyl(4-chlorophenyl)methyl(lH- l,2,4-triazol-l-ylmethyl)silane 90 (3,4-Dichlorophenyl)dimethyl(lH l,2,4-triazol-l-ylmethyl)silane 100 Oimethyl(4-methoxyphenyl)(lH-1,2,4- triazol-l-ylmethyl)silane 100 (2,4-Oichlorophenyl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane 100 bis(4-Chlorophenyl)(methyl)(lH- 1,2,4-triazol-1-ylmethyl)silane 100 (lH-1,2,4-Triazol-l-ylmethyl)tri- phenylsilane 100 Methyldiphenyl(1H-1,2,4-triazol-1 ylmethyl)silane 100 Oimethyl(lH-1,2,-triazol-1-yl- methyl) (2-trifluoromethylphenyl) silane 100 Table 3 (continued) % Control Barley Compound Powdery Mildew <RTI ID=134.1> Dodecyl(dimethyl)(lH-1,2,4-triazol- l-ylmethyl)silane 1OQA Butyl(4-chlorophenyl)(1H-imidazol l-ylmethyl)methylsilane 100 (3,4-Dichlorophenyl)(1H-imidazol l-ylmethyl)dimethylsilane 80 Dimethyl(lH-imidazol-l-ylmethyl) (4-methoxyphenyl)silane 100 (2,4-Dichlorophenyl)dimethyl(lH- imidazol-l-ylmethyl)silane 100 bis(4-Chlorophenyl)(lH-imidazol-l- ylmethyl)methylsilane 100 Oiphenyl(lH-imidazol-l-ylmethyl)- methylsilane 100 Dimethyl(lH-imidazol-l-ylmethyl) (4-trifluoromethylphenyl)silane 100 Oodecyl(dimethyl)(lH-imidazol-l ylmethyl) silane 100A A Compound applied at a concentration of 200 ppm. 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 inaegualis, causal agent of apple scab, and incubated in a saturated humidity chamber at 200 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. Phyto- toxicity expressed as growth reduction was observed on some of the plants in association with disease control. Table 4 Compound % Control Apple Scab Oimethyl(4-methylphenyl)(lH-1,2,4- triazol-l-ylmethyl)silane SOGA (4-8romophenyl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane 90G (l,l'-8iphenyl-4-yl)dimethyl(lH l,2,4-triazol-l-ylmethyl)silane 100 (4-Chlorophenyl)dimethyl(lH-1,2,4 triazol-l-ylmethyl)silane 100 Butyl(4-chlorophenyl)methyl(lH- 1,2,4-triazol-l-ylmethyl)silane lOOG Oimethyl(l-naphthalenyl)(lH-1,2,4- triazol-l-ylmethyl)silane 50 Table 4 (continued) Compound -. X Control Apple Scab (3,4-Oichlorophenyl)dimethyl(lH- 1,2,4-triazol-1-ylmethyl)silene 80 Dimethyl(4-phenoxyphenyl)(lH-1,2,4- triazol-l-ylmethyl)silane 100 Dimethyl(4-methoxyphenyl)(1H-1,2,4 triazol-l-ylmethyl)silane 100 (2,4-Oichlorophenyl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane 100 bis(4-Chlorophenyl)(methyl)(1H 1,2,4-triazol-1-ylmethyl)silane 100 Methyldiphenyl(1H-1,2,4-triazol-1 ylmethyl)silane 100 (1,1'-Biphenyl-4-yl)dimethyl(4H 1,2,4-triazol-4-ylmethyl)silane 80 bis(4-Fluorophenyl)(methyl)(1H 1,2,4-triazol-1-ylmethyl)silane 100 Dimethyl(4-fluorophenyl)(lH-1,2,4- triazol-l-ylmethylsilane 8SC8 Oimethyl(4-methylthiophenyl)(lH 1,2,4-triazol-1-ylmethyl)si.lane 60 Oimethyl(lH-1,2,4-triazol-l-ylmethyl) (2-trifluoromthylphenyl)silane (2-Methoxyphenyl)dimethyl(1H-1,2,4 triazol-l-ylmethyl)silane 80 Butyl(2,4-dichlorophenyl)methyl(1H 1,2,4-triazol-l-ylmethyl)silane lOOG bis(2,4-Dichlorophenyl)(methyl)(1H 1,2,4-tiazol-1-ylmethyl)silane 100 (2,4-Dichlorophenyl)methyl(phenyl) (1H-1,2,4-triazol-1-ylmethyl)silene 100Q (4-ChlorophenyL)methyl(phenyl)(lH 1,2,4-triazol-1-ylmethyl)silane 100 Table 4 (continued) Compound % Control Apple Scab (4-Fluorophenyl)methyl(phenyl)(lH- l,2,4-triazol-l-ylmethyl)silane 100 Butyl(methyl)phenyl(1H-1,2,4-triazol l-ylmethyl) silane 80 Dodecyl(dimethyl)(1H-1,2,4-triazol 1-ylmethyl)silane 408C,Q (2-Chlorophenyl)dimethyl(lH-1,2,4 triazol-l-ylmethyl)silane 100 [4-(4-Chlorophenoxy)phenyl]dimethyl (1H-1,2,4-triazol-1-ylmethyl)silane 100 (1,1'-Biphenyl-4-yl)butyl(methyl) (1H-1,2,4-triazol-1-ylmethyl)silane 80 Butyl(4-fluorophenyl)methyl(lH-1,2,4- triazcl-l-ylmethyl)silane 100 (1,1'-Biphenyl-4-yl)methyl(phenyl) (1H-1,2,4-triazol-1-ylmethyl)silane 100 (1,1'-Biphenyl-2-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane 60 (l,l'-8iphenyl-3-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane 50 2-Chlorophenyl(methyl)phenyl(1H-1,2,4 triazol-l-ylmethyl)silane 90 4-8romophenyl(methyl)phenyl(lH-1,2,4 triazol-l-ylmethyl)silane 100 [bis(2-Chlorophenyl)]methyl(1H-1,2,4 triazol-1-ylmethyl)silane 40 [bis(4-Bromophenyl)]methyl(1H-1,2,4 triazol-1-ylmethyl)silane 80 (1,1'-Biphenyl-4-yl)dimthyl(1H-1,2,4 triazol-1-ylmethyl)silane, 4-dodecyl benzenesulfonic acid salt 100 Table 4 (continued) Comoound % Control Aople Scab (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane, 1: :1 com plex with cuprous chloride 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-l-ylmethyl) silane, 1:1 com plex with zinc (II) chloride 100 (l,l'-8iphenyl-4-yl)dimethyl(lH-1,2,4- triazol.l-ylmethyl)silane, 1:1 com plex with manganous sulfate 100 2-Chlorophenyl(4-chlorophenyl)methyl (1H-1,2,4-triazol-1-ylmethyl)silane 90 2-Chlorophenyl(dimethyl)(lH-1,2,4- triazol-l-ylmethyl)silane 60 (l,l'-Biphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 80 Butyl(4-chlorophenyl)(1H-imidazol 1-yülmethyl)methylsilane 90 (lH-Imidazol-l-ylmethyl)dimethyl- (l-naphthalenyl)silane 40 (3,4-Dichlorophenyl)(1H-imidazol l-ylmethyl)dimethylsilane 80 (lH-Imidazol-l-ylmethyl)dimethyl- (4-phenoxyphenyl)silane 100 (2,4-Oichlorophenyl)dimethyl(lH- imidazol-l-ylmethyl)silane 100 Oiphenyl(lH-imidazol-l-ylmethyl) methylsilane 50 bis(4-Fluorophenyl) (lH-imidazol-l- ylmethyl)methylsilane 100 Dimethyl(lH-imidazol-l-ylmethyl)- (4-trifluoromethylphenyl)silane 60C [4-(1,1-Dimethylethyl)phenyl](1H imidazol-l-ylmethyl)dimethylsiiane 50 Table 4 (continued) Compound % Control Aoole Scab 8utyl(2,4-dichlorophenyl) (lH-imida- zol-l-ylmethyl)methylsilane 1008 bis(2,4-Dichlorophenyl)(1H-imidazol 1-ylmethyl)methylsilane 40 (2,4-Dichlorophenyl)(1H-imidazol-1 ylmethyl)methyl(phenyl)silane 80 (4-Chlorophenyl)(1H-imidazol-1-yl methyl)methyl(phenyl)silane 100 (4-Fluorophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 100 (lH-Imidazol-l-ylmethyl) (2-methoxy- phenyl)dimethylsilane 60 (2-Chlorophenyl)(lH-imidazol-l-yl methyl)dimethylsilane 90 Butyl(lH-imidazol-l-ylmethyl) methyl(phenyl)silane 80 (l,l'-8iphenyl-4-yl)butyl(lH-imida zol-l-ylmethyl)methylsilane 100 8utyl(4-fluorophenyl)(lH-imidazol- l-ylmethyl)methylsilane 80 Oibutyl(lH-imidazol-l-ylmethyl)- methylsilane 30 bis(l,l'-8iphenyl-4-yl)(lH-imi dazol-l-ylmethyl)methylsilane 50 (lH-Imidazol-l-ylmethyl)bis(4- methoxyphenyl)]methylsilane 50 (I,L'-Biphenyl-2-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 90 (l,l'-Biphenyl-3-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 90 (2-Chlorophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 100 Table 4 (continued) Compound t Control Apple Scab (4-8romophenyl)(lH-imidatol-l-yl- methyl)methyl(phenyL)silane 30 [bis(2-Chlorophenyl)](1H-imidazol l-ylmethyl)methylsilane 6Q Dimethyl(1H-imidazol-1-ylmethyl) (4-methylsulfonylphenyl)silane 80 Cyclohexyl(dimethyl(1H-imidazol-1 ylmethyl) silane lOGE [bis(4-Bromophenyl)](1H-imidazol-1 ylmethyl)methylsilane 50 (1,1'-Biphenyl-4-yl)dimethyl(1H imidazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 (2-Chlorophenyl)(4-chlorophenyl)(1H imidazol-1-ylmethyl)methylsilane 80 (lH-Imidazol-l-ylmethyl) phenyl- Cbis(2-propoxy) ]silane 70 (2-Chlorophenyl)(dimethyl)(lH-imi dazol-l-ylmethyl) silane 60 AG = growth reduction. BC = chlorosis. Ccompound applied at a concentration of 400 ppm. DB = burn. 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 200 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 same of the plants in association with disease control. Table 5 Control of Southern Compound Corn Leaf blight (4-8romophenyl)dimethyl(lH-1,2,4 triazol-l-ylmethyl)silane 90 (1,1'-8iphenyl-4-yl)dimethyl(lH- l,2,4-triazol-l-ylmethyl)silane 90 (3,4-Oichlorophenyl)dimethyl(lH- l,2,4-triazol-l-ylmethyl)silane 90 Oimethyl(4-methoxyphenyl)(lH-1,2,4- triazol-l-ylmethyl)silane 90 (2,4-Dichlorophenyl)dimethyl(lH 1,2,0-triazol-l-ylmethyl)silane 90 bis(4-Chlorophenyl)(methyl)(lH 1,2,4-triazol-l-ylmethyl)silane 80 Table 5 (continued) % Control of Southern Compound Corn Leaf Blight Methyldiphenyl(lH-l,2,4-triazol-1 ylmethyl)silane 80 (1,1'-Biphenyl-4-yl)dimethyl(4H 1,2,4-triazol-4-ylmethyl)silane 100 bis(4-Fluorophenyl)(methyl)(1H 1,2,4-triazol-1-ylmethyl)silane 100 Dimethyl(4-fluorophenyl)(lH-1,2,4 triazol-l-ylmethyl)silane 90 Oimethyl(4-methylthiophenyl) (lH- 1,2,4-triazol-l-ylmethyl)silane 80 Dimethyl(1H-1,2,4-triazol-1-yl methyl) (4-trifluoromethylphenyl) silane 50 C4-(l,l-DimethyfethyIfphenyljdi- methyl(lH-1,2,4-triazol-l-yl- methyl) silane 60 (2-Methoxyphenyl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane 70 Butyl(2,4-dichlorophenyl)methyl(1H 1,2,4-triazol-l-ylmethyl)silane 100 bis(2,4-Dichlorophenyl)(methyl)(1H 1,2,4-triazol-1-ylmethyl)silane 80 (4-Chlorophenyl)methyl(phenyl)(lH 1,2,4-triazol-1-ylmethyl)silane 90 (4-Fluorophenyl)methyl(phenyl) (lH- 1,2,4-triazol-1-ylmethyl)silane 90 (2-Chlorophenyl)dimethyl(lH-1,2,4 triazol-l-ylmethyl)silane 100 [4-(4-Chlorophenoxy)phenyl]dimethyl (1H-1,2,4-triazol-1-ylmethyl)silane 50 (3,5-Oichlorophenyl)dimethyl(lH- 1,2,4-triazol-1-ylmethyl)silane 40 Table 5 (continued) % Control of Southern Compound Corn Leaf Blight (l,l'-8iphenyl-4-yl)butyl(methyl) (lH-1,2,4-triazol-1-ylmethyl)silane 50 (1,1'-Biphenyl-4-yl)methyl(phenyl) (1H-1,2,4-triazol-1-ylmethyl)silane 90 [bis(4-Methoxyphenyl)]methyl(1H-1,2,4 triazol-1-ylmethyl)silane 90 (1,1'-Biphenyl-2-yl)dimethyl(1H-1,2,4 triazol-l-ylmethyl)silane 90 (l,l'-8iphenyl-3-yl)dimethnyl(lH-1,2,4- triazol-l-ylmethyl)silane 100 2-Chlorophenyl(methyl)phenyl(1H-1,2,4 triazol-1-ylmethyl)silane 100 4-Bromophenyl(methyl)phenyl(lH-1,2,4- triazol-l-ylmethyl)silane 80 [bis(2-Chlorophenyl)]methyl(1H-1,2,4 triazol-1-ylmethyl)silane 60 Cyclohexyl(dimethyl)(lH-1,2,4-triazol- l-ylmethyl)silane 50 (l,l'-8iphenyl-4-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane, 4-dodecyl benzenesulfonic acid salt 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane, 1:1 com plex with cuprous chloride 100 (l,l'-8iphenyl-4-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane, 1:1 com plex with zinc (II) chloride 90 (l,l'-8iphenyl-4-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane, 1: :1 com plex with manganous sulfate 100 2-Chlorophenyl(4-chlorophenyl)methyl- (1H-1,2,4-triazol-1-ylmethyl)silane 60 Table 5 (continued) % Control of Southern Compound -Corn eaf Blight (1,1'-Biphenyl-4-yl)dimethyl(1H imidazol-l-ylmethyl)silane 90 Butyl(4-chlorophenyl)(1H-imidazol l-ylmerhyl)methylsilane 30 (3,4-Dichlorophenyl)(1H-imidazol l-ylmethyl)dimethylsilane 70 (2,4-Dichlorophenyl)dimethyl(1H imidazol-l-ylmethyl)silane 70 bis(4-Chlorophenyl) (lH-imidazol-l- ylmethyl )methylsilane 60 (lH-Imidazol-l-y lmethyl ) triphenyl- silane 50 Diphenyl(lH-imidazol-I-ylmethyl)- methylsilane 60 bis(4-Fluorophenyl)(1H-imidazol-1 ylmethyl)methylsilane 60 <RTI ID=144.7> C4-(l,l-OimethylethyI)phenyllC1H- imidazol-l-ylmethyl)dimethylsilane 70 (lH-Imidazol-l-ylmethyl)dimethyl- (2-trifluoromethylphenyl)silane 90 Butyl(2,4-dichlorophenyl)(lH-imida- zol-l-ylmethyl)methylsilane 80 bis(2,4-Dichlorophenyl)(1H-imidazol l-ylmethyl)methylsilane 80 (4-Fluorophenyl)(1H-imidazol-1-yl methyl)methyl(phenyl)silane 80 (2,6-0imethoxyphenyl)(dimethyl)(lH- imidazol-l-ylmethyl)silane 50 Oibutyl(lH-imidazol-l-ylmethyl) methylsilane 90 Table 5 (continued) % Control of Southern Compound Corn Leaf Blight (1,1'-Biphenyl-4-yl)(1H-imidazol 1-ylmethyl)methyl(phenyl)silane 80 (l,l'-8iphenyl-3-yl)dimethylCaH- imidazol-l-ylmethyl)silane 90 [bis(2-Chlorophenyl)](1H-imidazol 1-ylmethyl)methylsilane 90 Cyclohexyl(dimethyl(1H-imidazol-1 ylmethyl)silane 50 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 inccu-- lated with a spore suspension of Cercospora arachidicola, 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)(lH l,2,4-triazol-l-ylmethyl)silane 100 Methyldiphenyl(lH-l ,2, 4-triazol-l- ylmethyl)silane 100 (l,l'-Biphenyl-4-yl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane 100 (4-Chlorophenyl)dimethyl(lH-l,2,4- triazol-l-ylmethyl)silane 90 Oimethyl(l-naphthalenyl)(lH-1,2,4- triazol-l-ylmethyl)silane 90 (2,4-Dichlorophenyl)dimethyl(lH l,2,4-triazol-l-ylmethyl)silane 100 Table 6 (continued) % Control Peanut Compound Early Leafspot bis(4-Fluorophenyl)(methyl)(1H l,2,4-triazol-l-ylmethyl)silane 100 Dimethyl(4-fluorophenyl)(1H-1,2,4 triazol-l-ylmethyl)silane 50 [4-(1,1-Dimethylethyl)phenyl]di methyl(1H-1,2,4-triazol-1-yl methyl)silane 35 Oimethyl(lH-1,2,4-triazol-1-yl- methyl)(2-trifluoromethylphenyl) silane 258 8utyl(2,4-dichlorophenyl)methyl(lH l,2,4-triazol-l-ylmethyl)silane 100 bis(2,4-0ichlorophenyl)(methyl)(lH- l,2,4-triazol-l-ylmethyl)silane 100 (2,4-Oichlorophonyl)methyl(phenyl)- (1H-1,2,4-triazol-1-ylmethyl)silane 100 (4-Chlorophenyl)methyl(phenyl)(lH 1,2,4-triazol-1-ylmethyl)silane 100 (4-Fluorophenyl)methyl(phenyl)(lH 1,2,4-triazol-l-ylmethyl)silane 100 (2-Chlorophenyl)dimethyl(lH-1,2,4 triazol-l-ylmethyl)silane 30 (1,1'-Biphenyl-4-yl)butyl(methyl) (1H-1,2,4-triazol-1-ylmethyl)silane 100 bis(l,l'-8iphenyl-4-yl)(methyl)(lH 1,2,4-triazol-l-ylmethyl)silane 80 <RTI ID=147.8> (l,l'-8iphenyl-4-yl)methyl(phenyl)- (1H-1,2,4-triazol-1-ylmethyl)silane 100 [bis(4-Methoxyphenyl)]methyl(1H-1,2,4 triazol-l-ylmethyl)silane 30 (l,l'-8iphenyl-2-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane 100 Table 6 (continued) % Control Peanut Compound Early Leafspot (1,1'-Biphenyl-3-y)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane 90 2-Chlorophenyl(methyl)phenyl(1H-1,2,4 triazol-l-ylmethyl)silane 100 4-8romophenyl(methyl)phenyl(lH-1,2,4- triazol-l-ylmethyl)silane 100 Cbis(2-Chlorophenyl)]methyl(lH-1,2,4 triazol-l-ylmethyl)silane 100 [bis(4-Bromophenyl)]methyl(1H-1,2,4 triazol-1-ylmethyl)silane 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane, 4-dodecyl benzenesulfonic acid salt 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-l-ylmethyl)silane, 1:1 com plex with cuprous chloride 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-l-ylmethyl)silane, 1:1 com plex with zinc (II) chloride 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane, 1:1 com plex with manganous sulfate 100 2-Chlorophenyl(4-chlorophenyl)methyl (1H-1,2,4-triazol-1-ylmethyl)silane 90 Cbis(2-Fluorophenyl)jmethyl(1H- 1,2,4-triazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 Ebis(2-Fluorophenyl) ]methyl(1H- 1,2,4-triazol-l-ylmethyl)silane, 2: :1 complex with cupric chloride 100 (l,l'-8iphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 100 Table 6 (continued) 96 Control Peanut Compound Early teafspot (2,4-2ichlorophenyl)dimethyl(lH- imidazol-l-ylmethyl)silane 100 Diphenyl(lH-imidazol-l-ylmethyl)- methylsilane 50 bis(4-Fluorophenyl)(1H-imidazol-l- ylmethyl)methylsilane 100 Dimethyl(4-fluorophenyl)(lH-imida zol-l-ylmethyl)silane 60BA Dimethyl(1H-imidazol-1-ylmethyl) (4-trifluoromethylphenyl)silane 368 Dimethyl(lH-imidazol-l-ylmethyl) (3-trifluoromethylphenyl)silane 50 Butyl(2,4-dichlorophenyl)(1H-imida zol-l-ylmethyl)methylsilane . 100 bis(2,4-Dichlorophenyl)(lH-imidazol 1-ylmethyl)nethylsilane 90 (2,4-Oichlorophenyl)(lH-imidazol-l- ylmethyl)methyl(phenyl)silane 100 (4-Chlorophenyl) (lH-imidazol-l-yl- methyl)methyl(phenyl)silane 100 (4-Fluorophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 100 (2-Chlorophenyl)(lH-imidazol-l-yl- methyl)dimethylsilane 80 (1,1'-8iphenyl-4-yl)butyl(1H-imida zol-l-ylmethyl)methylsilane 90 bis(l,l'-8iphenyl-4-yl)(lH-ii- dazol-l-ylmethyl)methylsilane 60 (l,l'-Biphenyl-4-yl) (lH-imida- zol-1-ylmethyl)nethyl(phenyl) silane 80 Table 6 (continued) % Control Pe Compound Early Leafs (l,l'-8fphenyl-2-yl)dimethyl(lH- imidazol-l-ylmethyl)sllane 30 (1,1'-Biphenyl-3-yl)dimethyl(1H imidazol-l-ylmethyl)silane 80 (2-Chlorophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 100 (4-Bromophenyl)(1H-imidazol-1-yl methyl)methyl(phenyl)sila-ne 90 [bis(2-Chlorophenyl)](1H-imidazol l-ylmethyl)methylsilane 100 [bis(2-Bromophenyl)](1H-imidazol ylmethyl )methylsilane 50 (l,l'-8iphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane, 1:1 complex with cuprous chloride 100 (2-Chlorophenyl)(4-chlorophenyl)(1H imidazol-l-ylmethyl)methylsilane 80 AB = Phytotoxic burn. BCompound applied at a concentration of 400 ppm. Example 74 Compounds of this invention were dissolved in acetone in an amount equal to 656 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 phaseoli, causal agent of bean rust, and incubated in a saturated humidity chamber at 200 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 ó Control Compound Bean Rust (1,1'-8iphenyl-4-yl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane 100 (2,4-Diclorophenyl)dimethyl(1H 1,2,4-triazol-l-ylmethyl)silane 30GA bis(4-Chlorophenyl)(methyl)(lH- 1,2,4-triazol-l-ylmethyl)silane lOOG (4-Chlorophenyl)methyl(phenyl)(lH 1,2,4-triazol-1-ylmethyl)silane 988 (4-Fluorophenyl)methyl(phenyl)(lH l,2,4-triazol-l-ylmethyl)silane 1008 bis(4-Fluorophenyl) (methyl) (lH- 1,2,4-triazol-l-ylmethyl)silane 988 (l,l'-Biphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 100 Table 7 (continued) só Control Compound Bean Rust (2,4-Dichlorophenyl)dimethyl(lH imidazol-1-ylmethyl)silane 83 AG = growth reduction. 8compound applied at a concentration of 16 ppm. 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 con tanners. Upon drying, the peach halves were inoculated with two pieces of Monilinia 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 % Control Compound 8rown Rot (Dimethyl)phenyl(1,2,4-triazol-1 ylmethyl)silane 89 (Butyl)dimethyl(lH-l,2,4-triazol-1- ylmethyl) silane 95 (1,1'-8iphenyl-4-yl)dimethyl(lH- l,2,4-triazol-1-ylmethyl)silane 100 Butyl (4-chlorophenyl ) methyl ( lH- 1,2,4-triazol-l-ylmethyl)silane 98 Oimethyl(4-methoxyphenyl)(lH-1,2,4- triazol-l-ylmethyl)silane 97 Table 8 (continued) % Control Compound Brown Rot (2,4-Dichlorophenyl)dimethyl(1H 1,2,4-triazol-1-ylmethyl)silane 100 bis(4-Chlorophenyl)(methyl)(lH 1,2,4-triazol-1-ylmethyl)silane 95 (1,1'-Biphenyl-4-yl)dimethyl(4H l,2,4-triazol.4-ylmethyl)silane 96 bis(4-Fluorophenyl)(methyl)tlH- 1,2,4-triazol-l-ylmethyl)silane 100 Butyl(2,4-dichlorophenyl)methyl(lH 1,2,4-triazol-1-zlmethzl)silane 98 (4-Chlorophenyl)methyl(phenyl)(lH 1,2,4-triazol-1-zlmethzl)silane 70 (4-Fluorophenyl)methyl(phenyl)(lH 1,2,4-triazol-l-ylmethyl)silane 90 Butyi(4-fluorophenyl)methyl(lH-1,2,4- triazol-l-ylmethyl)silane 100 Dibutyl(methyl)(1H-1,2,4-triazol-1 ylmethyl) silane 81 (1,1'-Biphenyl-4-yl)dimethyl(1H imidazol-1-ylmethyl)silane 83 Butyl(4.chlorophenyl)(1H-imidazol l-ylmethyl)methylsilane 45 (lH-Imidazol-l-ylmethyl)dimethyl- (4-phenoxyphenyl)silane 80 (2,4-Oichlorophenyl)dimethyl(lH- imidazol-l-ylmethyl)silane 100 Diphenyl(lH-imidazol-l-ylmethyl) methylsilane 76 (4-Chlorophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 45 (4-Fluorophenyl)(1H-imidazol-1-yl methyl)methyl(phenyl)silane 63 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 Rhizoctonia 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. Table 9 % Control of Compound Rice Sheath Blight (l,l'-8iphenyl-4-yl)dimethyl (lH-1,2,4-triazol-1-ylmethyl)- silane 40 (3, 4-Oichlorophenyl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane 80 bis(4-Fluorophenyl)(methyl)(lH 1,2,4-triazol-l-ylmethyl)silane 80 E4-(l, 1-Dimethylethyl)phenyl]di- methyl(lH-1,2,4-triazol-l-yl- methyl)silane 90 Butyl(2,4-dichlorophenyl)methyl(lH l,2,4-triazol-l-ylmethyl)silane 50 (4-Chlorophenyl)methyl(phenyl)(lH 1,2,4-triazol-l-ylmethyl)silane 90 (4-Fluorophenyl)methyl(phenyl)(lH 1,2,4-triazol-l-ylmethyl)silane 80 Table 9 (continued) % Control of Compound Rice Sheath Blight Butyl(methyl)phenyl(1H-1,2,4-triazol l-ylmethyl)silane 90 (1,1'-Biphenyl-4-yl)butyl(methyl) (1H-1,24-triazol-1-ylmethyl)silane 80 Butyl(4-fluorophenyl)methyl(1H-1,2,4 triazol-l-ylmethyl)silane 80 bis(l,l'-Biphenyl-4-yl)(methyl)(lH- 1,2,4-triazol-l-ylmethyl)silane 90 Ebis(4-Methoxyphenyl)]methyl(lH-1,2,4- triazol-l-ylmethyl)silane 80 2-Chlorophenyl(methyl)phenyl(1H-1,24 triazol-l-ylmethyl)silane 90 4-8romophenyl(methyl)phenyl(lH-1,2,4- triazol-l-ylmethyl)silane 90 [bis(2-Chlorophenyl)]methyl(1H-1,2,4 triazol-1-zlmethyl)silane 60 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane, 1:1 com plex with cuprous chloride 90 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triyzol-1-ylmethyl)silane, 1:1 com plex with zinc (II) chloride 90 2-Chlorophenyl(4-chlorophenyl)methyl- (1H-1,2,4-triazol-1-ylmethyl)silane 70 (bis(2-Fluorophenyl) methyl(lH- 1,2,4-triazol-l-ylmethyl)silane, 1: :1 complex with cuprous chloride 90 (lH-Imidazol-l-ylmethyl)dimethyl (4-phenoxyphenyl)silane 70 bis(4-Fluorophenyl)(lH-imidazol-l- ylmethyl)methylsilane 90 Table 9 (continued) % Control of Compound Rice Sheath blight (lH-Imidazol-l-ylmethyl)dimethyl- (2-trifluoromethylphenyl)silane 80 Butyl(2,4-dichlorophenyl)(1H-imida zol-l-ylmethyl)methylsilane 90 bis(2,4-Dichlorophenyl)(1H-imidazol l-ylmethyl)methylsilane 80 (4-Fluorophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 90 (lH-Imidazol-l-ylmethyl) (2-methoxy- phenyl)dimethylsilane 90 [4-(4-Chlorophenoxy)phenyl]dimethyl (lH-imidazol-l-ylmethyl)silane 70 Butyl(lH-imidazol-l-ylmethyl)- methyl (phenyl) silane 80 (1,1'-Biphenyl-4-yl)butyl(1H-imida zol-l-ylmethyl)methylsilane 90 Butyl(4-fluorophenyl)(lH-imidazol- l-ylmethyl)methylsilane 80 (l,1'-8iphenyl-2-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 90 (1,1'-Biphenyl-3-yl)dimethyl(1H imidazol-l-ylmethyl)silane 90 Cbis(2-Chlorophenyl)](lH-imidazol- l-ylmethyl)methylsilane 40 (1,1'-Biphenyl-4-yl)dimethyl(1H imidazol-l-ylmethyl)silane, 1: :1 complex with cuprous chloride 50 (2-Chlorophenyl)(dimethyl)(lH-imi dazol-l-ylmethyl)silane 90 Example 77 Compounds of this invention were dissolved in acetone in an amount equal to 6S 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 Pyricularia oryzae, causal agent of rice blast, and incubated in a saturated humidity chamber at 280C 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 % Control of Compound Rice Blast Dimethyl(1-naphthalenyl)(1H-1,2,4 triazol-l-ylmethyl)silane 70 bis(4-Chlorophenyl) (methyl) (lH- l,2,4-triazol-l-ylmethyl)silane 90 bis(4-Fluorophenyl) (methyl) (lH- 1,2,4-triazol-l-ylmethyl)silane 100 i4-(1,1-Oimethylethyl)phenyl3di- methyl(lH-1,2,4-triazol-l-yl- methyl) silane 90 (4-Chlorophenyl)methyl(phenyl)(lH- 1,2,4-triazol-l-ylmethyl)silane 100 8utyl(methyl)phenyl(lH-1,2,4-triazol- l-ylmethyl)silane 90 (2-Chlorophenyl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane 100 Table 10 (continued) X Control of Compound -Rice Blast (1,1'-8iphenyl-4-yl)butyl(methyl)- (1H-1,2,4-triazol-1-ylmethyl)silane 100 8utyl(4-fluorophenyl)methyl(lH-1,2,4- triazol-l-ylmethyl)silane 10 Dibutyl(methyl)(1H-1,2,4-triazol-1 ylmethyl)silane 80 bis(l,l'-8iphenyl-4-yl)(methyl)(lH 1,2,4-triazol-l-ylmethyl)silane 100 (1,1'-Biphenyl-2-yl)dimethyl(1H-1,2,4 triazol-l-ylmethyl)silane 90 2-Chlorophenyl(methyl)phenyl(1H-1,2,4 triazol-1-ylmethyl)silane 100 4-8romdphenyl(methyl)phenyl(lH-1,2,4- triazol-l-ylmethyl)silane 80 (bis(2-Chlorophenyl)]methyl(1H-1,2,4 triazol-l-ylmethyl)silane 90 Dimethyl(4-methylsulfonylphenyl)(1H l,2,4-triazol-1-ylmethyl)silane 70 Cbis(4-8romophenyl)]methyl(lH-1,2,4- triazol-l-ylmethyl)silane 90 (1,1'-8iphenyl-4-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane, 4-dodecyl benzenesulfonic acid salt 80 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-l-ylmethyl)silane, 1:1 com plex with cuprous chloride 100 (1,1'-Biphenyl-4-yl)dimethyl(1H-1,2,4 triazol-1-ylmethyl)silane, 1:1 com plex with zinc (II) chloride 100 bis(2-Fluorophenyl)]methyl(1H- 1,2,4-triazol-1-ylmethyl)silane, 1:1 complex with cuprous chloride 90 Table 10 (continued) % Control of Compound Rice Blast ±bis(2-Fluorophenyl) ]methyl(lH- 1,2,4-triazol-1-ylmethyl)silane, 2: :1 complex with cupric chloride 100 (lH-Imidazol-l-ylmethyl)dimethyl- (4-phenoxyphenyl)silane 70 [4-(1,1-Dimethylethyl)phenyl](1H imidazol-l-ylmethyl)dimethylsilane 80 (4-Fluorophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 100 [4-(4-Chlorophenoxy)phenyl]dimethyl (lH-imidazol-l-ylmethyl)silane 100 Butyl(lH-imidazol-l-ylmethyl) methyl(phenyl)silane 90 (1,1'-Biphenyl-4-yl)butyl(1H-imida zol-l-ylmethyl)methylsilane 90 Butyl(4-flurorophenyl)(1H-imidazol l-ylmethyl)methylsilane 100 (1,1'-Biphenyl-2-yl)dimethyl(1H imidazol-l-ylmethyl)silane 90 (l,l'-8iphenyl--yl)dimethyl(lH- imidazol-l-ylmethyl)silane 80 [bis(2-Chlorophenyl)](1H-imidazol 1-ylmethyl)methylsilane 90 Oimethyl(lH-imidazol-l-ylmethyl) (4-methylsulfonylphenyl)silane 100 [bis(4-Bromophenyl)](1H-imidazol-1 ylmethyl)methylsilane 80 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 2000 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 Oimethyl(4-phenoxyphenyl)(lH-1,2,4 triazol-l-ylmethyl)silane 50 4-(4-Chlorophenoxy)phenyl]dimethyl- (lH-l,2,4-triazol-l-ylmethyl)silane 50 (l,l'-8iphenyl-2-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane 50 (l,l'-Biphenyl-4-yl)dimethyl(lH-l,2,4- triazol-l-ylmethyl)silane, 4-dodecyl benzenesulfonic acid salt 60 (1,1'-8iphenyl-4-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane, 1:1 com plex with cuprous chloride 100 (l,l'-8iphenyl-4-yl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane, 1: :1 com plex with zinc (II) chloride 90 Table 11 (continued) % Control of Compound Tomato tate Blight (bis(2-Fluorophenyl) ]methyl(lH- 1,2,4-triazol-1-ylmethyl)silane, 2:1 complex wi-th cupric chloride 40 (4-Bromophenyl)(lH-imidazol-l-yl methyl)dimethylsilane 30 (l,l'-8iphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 50 (lH-Imidazol-l-ylmethyl)dimethyl- (4-phenoxyphenyl)silane 80 Dimethyl(lH-imidazol-l-ylmethyl) (3-trifluoromethylphenyl)silane 70 (2,6-0imethoxyphenyl)(dimethyl)(lH- imidazol-l-ylmethyl)silane 50 [bis(2-Chlorophenyl)](1H-imidazol l-ylmethyl)methylsilane 60 Example 79 Compounds of this invention were incorporated into <RTI ID=163.1> 450C 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 mm2 from agar cultures of 5 Phytophthora species: -Phytophthora cinnamomi, P. cactorum, P. infestans, P. palmivora, and P. parasitica var. nicotianae were placed on the media and incubated at 220C 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 of 5 Phytophthora species Compound controlled in vitro (Butyl)dimethyl(1H-l,2,4-triazol-1- ylmethyL)silane 1 (3,3-Dichlorophenyl)dimethyl(1H l,2,4-triazol-1-ylmethyl)silane 2 (l,l'-8iphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 3 (lH-Imidazol-l-ylmethyl)dimethyl- (4-phenoxyphenyl)silane 4 (2,4-Oichlorophenyl)dimethyl(lH- imidazol-l-ylmethyl)silane 5 Oiphenyl(lH-imidazol-l-ylmethyl) methylsilane 2 (4-Fluorophenyl)(lH-imidazol-l-yl methyl)methyl(phenyl)silane 2 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 thoroughly coated, the seeds were allowed to air dry at room temperature. The cotton seeds were then planted into soil amended with the fungus Pythium 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 Pythium on Cotton Ethyldimethyl(lH-1,2,4-triazol-1- ylmethyl) silane 48 (1,1'-Biphenyl-4-yl)dimethyl(1H 1,2,4-triazol-l-ylmethyl)silane 12 (4-Chlorophenyl)dimethyl(lH-1,2, 4- triazol-l-ylmethyl)silane 53A Dimethyl(4-phenoxyphenyl)(lH-1,2,4- triazol-l-ylmethyl)silane silane (1,1l-8iphenyl-4-yl)dimethyl(lH- imidazol-l-ylmethyl)silane 18 (4-Chlorophenyl)(lH-imidazol-l ylmethyl)dimethylsilane 18A (3,4-Oichlorophenyl)(lH-imidazol- l-ylmethyl)dimethylsilane 15A Acontrol at a rate of 0.5 gm/kg seed. 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 thoroughly 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 Pythium aphanadermatum, sand, and corn meal at a rate sufficient to kill most untreated seeds. The seeds were held at 490F for 2 weeks and then at 700F 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 % Control of Compound Pythium on Corn Ethyldimethyl (lH-1 , 2, 4-triazol-l- ylmethyl) silane 13 (1,1'-8iphenyl-4-yl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane 30 (4-Chlorophenyl)dimethyl(lH-1,2,4- triazol-l-ylmethyl)silane 8 Dimethyl(l-naphthalenyl)(lH-1,2,4 triazol-l-ylmethyl)silane 30 (3,4-Dichlorophenyl)dimethyl(lH- 1,2,4-triazol-l-ylmethyl)silane 43 Ethyl(lH-imidazol-l-ylmethyl) dimethyl silane 70 (lH-Imidazol-l-ylmethyl)dimethyl- (4-methylphenyl)silane 30 Table 14 (continued) % Control of Compound Pythium on Corn (1,1'-Biphenyl-4-yl)dimethyl(1H imidazol-l-ylmethyl)silane 32 (4-Chlorophenyl) (lH-imidazol-l- <RTI ID=166.3> ylmethyl)dimethylsilane 25 (lH-Imidazol-l-ylmethyl) dimethyl- (l-naphthalenyl)silane 27 (3,4-Dichlorophenyl)(1H-imidazol l-ylmethyl)dimethylsilane 30 (1H-Imidazol-1-ylmethyl)dimethyl (4-phenoxyphenyl)silane 5 Dimethyl(4-fluorophenyl)(1H-imi dazol-1-ylmethyl)silane 15

Claims: Claims: 1. A compound of the formula: EMI167.1 wherein Q1 and Q2 are independently H or CH3; n is 1; R1 is C2-C18 alkyl, C3-C6 cycloalkyl, naphthyl, or EMI167.2 where R4 and R5 are independently -H; halogen; -OCH3; -OCF3; -SCH3; -SO2CH3, phenyl; phenyl substituted with halogen and/or C1-C4 alkyl and/or -CF phenoxy; phenoxy substituted with halogen and/or C1-C4 alkyl and/or; -CF3; C1-C4 alkyl; or cyclohexyl; R2 and R3 are independently C1-C5 alkyl, C3-C6 cycloalkyl, OR6, or EMI167.3 where R6 is H or C1-C4 alkyl, or one R6 group may be EMI167.4 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 which may optionally be substituted by up to our alkyl groups R7-R10 that have a total of up to four carbon atoms, viz. EMI168.1 and salts thereof with protic acids and complexes with metal ions 2. A compound of the formula: EMI168.2 wherein Q1' Q2 and Q3 are independently H or : CH3; n is 1; is C6-C18 alkyl, C3-C6 cycloalkyl, naphthyl or EMI168.3 where R4 and R5 are independently -H; halogen; -OCH3; -OCF3; -SCH3; -S02CH3; phenyl; phenyl substituted with halogen and/or C1-C4 alkyl andior -CF3; phenoxy; phenoxy substituted with halogen and/or C1-C4 alkyl and/or -CF 3; -CF3; C1-C4 alkyl; or cyclohexyl; with the proviso that for compounds of Formula II, both R4 and R5 may not simultaneously be H; and R2 and R3 are independently C1-C6 alkyl, C3-C6 cycloalkyl, OR6, or EMI169.1 where R4 and R5 are as defined above except that said proviso does not apply, and R6 is H or C1-C4 alkyl, or one R6 group may be EMI169.2 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 which may optionally be substituted by up to four alkyl groups R7-R10 that have a total of up to four carbon atoms, viz. EMI169.3 EMI170.1 and salts thereof with protic acids and complexes with metal ions. 3. A compound of claim i or 2 wherein Q1 and Q2 are H. 4. A compound of claim 3 wherein R1 or R1' is EMI170.2 2 is C4 alkyl or EMI170.3 and R3 is C1-C4 alkyl. 5. A compound of claim 4 wherein R1 and R1' are EMI170.4 where R4 is H, F, C1, Br or phenyl, and R5 is H, F, C1 or Br; and R2 is EMI170.5 or C1-C4 alkyl; and R3 is C1-C4 alkyl 6. The compound of Claim 1 which is (l,l'-bi- phenyl-4-yl)dimethyl(lH-1,2,4-triazol-1-ylmethyl)- silane. 7. The compound of Claim 1 which is bis(4 chlOrophenyl3methyl(1H-1,2,4-triazol-1-ylmethyl)- silane. 8. The compound of Claim 1 which is Cpis(4- fluorophenyl)]methyl(1H-1,2,4-triazol-1-ylmethyl) silane. 9. The compound of Claim 1 which is 4-fluorophenyl(methyl)phenyl(1H-1,214-triazol-l-ylmethyl) silane. 10. The compound of claim 2 which is (2,4-di chlorophenyl)dimethyl(1H-imidazol-1-ylmethyl)silane. 11. A compound of claim 1 wherein: Q1 and Q2 are H; R1 is C2-C18 alkyl, C3-C6 cycloalkyl, naphthyl, or EMI171.1 where R4 and R5 are independently -H, halogen, phenyl, -OCH3, -SCH3, phenoxy, -CF3 or C1-C4 alkyl; and R1 and R3 are independently C1-C6 alkyl, C3-C6 cycloalkyl, or OR6, where R6 is H or C1-C4 alkyl. 12. A compound of claim 2 wherein Q1' Q2 and Q3 are H; R1' EMI171.2 where R4 and R5 are as defined in claim 11 but are not both H; and R2 and R3 are independently C1-C4 alkyl or OR6, where R6 is H or C1-C4 alkyl. 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 l-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 1 to 12. 15. 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 comprises a compound of the formula: wherein EMI172.1 Q1' Q2' Q3, n, R2, R3, and R6 are as defined in claim 2, and R1' is C2 C18 alkyl, C3-C6 cycloalkyl, naphthyl or EMI172.2 where R4 and R5 are independently -H; halogen; -OCH3; -OCF3; -SCH3; -SO2CH3; 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; C1-C alkyl; or cyclohexyl; or a salt thereof with a protic acid or a complex thereof with a metal ion. 16. A process for preparing a compound of claim 1 or 2 which comprises reacting a silane derivative of formula EMI173.1 wherein R1, R1, 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 EMI173.2 wherein Q1 and Q2 are independently H or CH3 and X is H, CH or 0CM3, or with an alkali metal salt thereof. 17. A process for preparing a compound of claims 1 or 2 wherein R2 and/or R3 is ORE which comprises reacting a corresponding compound of formula EMI173.3 wherein R2 is halogen or R2 and R3 is halogen or R3, at least one of R2 and R3 being halogen, and Y is as defined in claim 15, with a triazole or imidazole sodium salt of formula EMI173.4 wherein X is N, CH or CCH3, and reacting the intermediate so obtained with R6 OH to obtain a compound of claim 1 or 2 wherein R2 and/or R3 is R60; R1 having a value as defined for R; in claim 2 when X is CH or COM3. 18. A process for preparing a compound of claim 1 which comprises reacting I) an intermediate selected EMI174.1 <tb> from <SEP> the <SEP> group <SEP> R3 <SEP> R,2 <tb> <SEP> Cl3SiCH2Cl, <SEP> C12SiCH2Cl <SEP> and <SEP> Cl-Si-CH2Cl <tb> <SEP> R3 <tb> in a suitable solvent with R1M where M is Na, Li or MgX where X is Br, C1, I, at a temperature of from -804 to 400C to form a chloromethyl silane; 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; R1, R2 and R3 being as defined in claim 1. 19. A process for preparing a compound of Claim 1 which comprises 1) reacting EMI174.2 with R6OH in a suitable solvent with a suit able base at a temperature of OOlOOOC to form an alkoxy or dialkoxy chloromethylsilane; and 2) reacting the chloromethylsilanes with 1,2,4-tri azole, its 3-methyl or 3,5-dimethyl derivative, or their alkali metal salts in polar aprotic solvents, ethers or ketones at Oo to 200 C; R1, R2 and R6 being: as defined in claim ]. 20. A process for preparing a compound of claim 2 which comprises reacting 1) an intermediate selected from the group EMI174.3 in a suitable solvent with R1,M where M is Na, Li or MgX where X is Br, C1, I, at a temperature of from -80 to 40 C to form a chloromethyl silane; and 2) reacting the chloromethylsilane with imidazole, its 2-methyl, 2,4-dimethyl, 4,5-dimethyl, and 2,a,5-trimethyl derivatives, or their alkali metal salts in polar aprotic solvents, ethers or ketones at 0 to 200 C; R1, R2 and R3 being as defined in claim 2. 21. A process for preparing a compound of claim 2 which comprises 1) reacting EMI175.1 with R6OH in a suitable solvent with a suitable base at a temperature of 0 to 1000C to form an alkoxy or dialkoxy chloromethylsilane; and 2) reacting the chloromethylsilane with imidazole, its 2-methyl, 2,4methyl, 4,5-methyl, and 2,4,5-trimethyl derivatives, or their alkali metal salts in polar aprotic solvents, ethers or ketones at 0 to 200 C; R1', R2 and R6 being as defined in claim 2. Claims: 1. A process for the preparation of a compound of the formula: EMI176.1 wherein Q1 and Q2 are independently H or CH3; n is 1; R1 is C2-C18 aklyl, C3-C6 cycloalkyl, naphthyl, or EMI176.2 where Ra and R5 are independently -H; halogen; -OCH3; -OCF3; -SCH3; -S02CH3; 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; C1-C4 alkyl; or cyclohexyl; R2 and R3 are independently C1-C6 alkyl, C3-C, cycloalkyl, OR6, or EMI176.3 where R6 is H or C1-C4 alkyl, or one R6 group may be EMI177.1 with the proviso that both R2 and R3 may not be OH; and R2 and 23 together may be a 1,2- or 1,3- or 1,4-glycol bridge or a 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, EMI177.2 and salts thereof with protic acids and complexes with metal ions, which comprises (a) reaction of a silane derivative of formula EMI177.3 wherein R1, R2 and R3 are as defined above and Y is chlorine, bromine or arylsulfonyloxy, with a 1,2,4-triazole of formula EMI178.1 wherein Q1 and Q2 are as defined above or with an alkali metal salt thereof; or (b) reacting a corresponding compound of formula EMI178.2 wherein R1 and Y are as defined above, R2 is halogen or R2 and R3 is halogen or R3, at least one of R2, and R3 being halogen, with a triazole sodium salt of formula EMI178.3 wherein Q1 and Q2 are as defined above, and reacting the intermediate so obtained with R,OH to contain a product of formula I wherein R2 and/or R3 is R60. 2. A process for the preparation of a compound of formula I as defined in claim 1, which comprises reacting 1) an intermediate selected from the group EMI179.1 in a suitable solvent with R1M where M is Na, Li or MgX where X is Br, C1, I, at a temperature of from -800C to 40 C to form a chloromethyl silane; 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; R1, R2 and R3 being as defined in claim 1. 3. The process of claim 1 or claim 2 wherein: Q1 and Q2 are H; R1 is C2-C18 alkyl, C3-C6 cycloalkyl, naphthyl, or EMI179.2 where R4 and R5 are independently -H, halogen, phenyl,-OCH3, -SCH3, phenoxy, -CF3 or C 1-C4 alkyl; and R1 and R3 are independently C1-Cs alkyl1 C3-C6 cycloalkyl, or OR6, where R6 is H or C1-C4 alkyl. 4. A process for the preparation of a compound of the formula: EMI180.1 wherein Q1' Q2 and Q3 are independently H or CH3; n is 1; R'1 is C6-C18 alkyl, C3-C6 cycloalkyl, naphthyl or EMI180.2 where R4 and R are independently -H; halogen; -OCH3; -OCF3; -SCH3; -SO2CH3; phenyl; phenyl substituted with halogen and/or C1-C4 alkyl andior -CF3; phenoxy; phenoxy substituted with halogen and/or C1-C4 alkyl and/or -CF3; -CF3; 3' C1-C4 alkyl; or cyclohexyL; with the proviso that for compounds of Formula II, both R4 and R5 may not simultaneously be H; and R2 and R3 are independently C1-C6 alkyl, C3-C6 cycloalkyl, OR6, or EMI180.3 where R4 and R5 are as defined above except that said proviso does not apply and R6 is H or C 1-C4 alkyl, or one R6 group may be EMI181.1 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 which may optionally be substituted by up to four alkyl groups R7 -R10 that have a total of up to four carbon atoms, viz EMI181.2 and salts thereof with protic acids and complexes with metal ions, which comprises (a) reacting a silane derivative of formula EMI182.1 wherein R1', R2 and R3 are as defined above and Y is chlorine, bromine, iodine or arylsulfonyloxy, with an imidazole of formula EMI182.2 wherein Q1 and Q2 are as defined above, or with an alkali metal salt thereof, or (b) reacting a corresponding compound of formula EMI182.3 wherein R1 and Y are as defined above, R2 is halogen or R2, R3 is halogen or R3, at least one of R2 and R3 being halogen, with an imidazole sodium salt of formula EMI182.4 wherein Q1 and Q2 are as defined above, and reacting the intermediate so obtained with R 6OH to obtain a compound of formula II wherein R2 and/or R3 is R6O. 5. A process for the preparation of a compound of formula II as defined in claim 4 which comprises reacting 1) an intermediate selected from the group EMI183.1 in a suitable solvent with R1,M where M is Na, Li or MgX where X is Br, C1, I, at a temperature of from -80 C to 40 C to form a chloromethyl silane; and 2) reacting the chloromethylsilane with imidazole, its 2-methyl, 2,4-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; R1, R2 and R3 being as defined in claim 2. 6. The process of claims 4 or S wherein Q1' Q2 and Q3 are H; R EMI183.2 where R4 and R5 are as defined in claim 3 but are not both H; and R2 and R3 are independently C 1-C4 alkyl or OR6, where R6 is H or C1-C4 alkyl. 7. The process of any of claims 1-6 wherein Q1 and Q2 are H, R1 or R' is EMI183.3 R2 is C1-C4 alkyl or EMI184.1 and R3 is C 1-C4 alkyl. 8. The process of claim 7 wherein R1 and R2, are EMI184.2 where R4 is H, F, C1, Br or phenyl, and R5 is H, F, C1 or Br; and R2 is EMI184.3 or C1 -C4 alkyl; and R3 is C1-C4 alkyl. 9. The process of claim 1 or 4 wherein the product is selected from: (1,1'-bi-phenyl-4-yl)dimethyl(1H-1,2,4-triazol-1ylmethyl)-silane; bis(4-chlorophenyl)methyl(1H-1,2,4-triazol-1ylmethyl)-silane; [bis(4-fluorophenyl)]methyl(1H-1,2,4-triazol1-ylmethyl) -silane; 4-fluorophenyl(methyl)phenyl (1H-1 ,2,4-triazol- 1-ylmethyl)-silane; and (2,4-dichloroiphenyl)dimethyl(1H-imidazol-1ylmethyl)silane. 10. 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 formula I as defined in any of claims 1-3 or 7-9. 11. 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 formula II as defined in any of claims 4-9. 12. 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 formula EMI185.1 where in Q1 t Q2 t Q3, n, R2, R3 and R6 are as defined in claim 2, and R1 is C2-C18 alkyl, C3-C6 cycloalkyl, naphthyl or EMI186.1 where R4 and R5 are independently- -H; halogen; -OCH3; -OCF3; -SCH3; -SO2CH3; 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; C1 -C4 alkyl; or cyclohexyl; or a salt thereof with a protic acid or a complex thereof with a metal ion.

Inventors: MOBERG, WILLIAM KARL
Applicants: E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1982
Main classification: C07F7
IPC codes: A01N55, C07F7