Fungicidal 1,2,4-triazole and imidazole derivatives

Claim 2

A compound of the formula: wherein Q 1 and Q 2 are independently H or CH 3 ; n is 1; R 1 is C 2 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl, or where R 4 and R 5 are independently -H; halogen; - OCH3 ; - OCF3 ; -SC H3 ; -S0 2 CH 3 ; phenyl; phenyl substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; phenoxy; phenoxy substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; -CF 3 ; C 1 -C 4 alkyl; or cyclohexyl; R 2 and R 3 are independently C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, OR 6 , or where R 6 is H or C 1 -C 4 alkyl, or one R 6 group nay be with the proviso that both R 2 and R 3 may not be OH; and R 2 and R 3 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 R 7 -R 10 that have a total of up to four carbon atoms, viz. or and salts thereof with protic acids and complexes with metal ions.

Claim 3

A compound of the formula: wherein Q 1 , Q 2 and Q 3 are independently H or CH 3 ; n is 1; R' 1 is C 6 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl or where R 4 and R 5 are independently -H; halogen; -OCH 3 ; -OCF 3 ; -SCH 3 ; -S0 2 CH 3 ; phenyl; phenyl substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; phenoxy; phenoxy substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; -CF 3 ; C 1 -C 4 alkyl; or cyclohexyl; with the proviso that for compounds of Formula II, both R 4 and R 5 may not simultaneously be H; and R 2 and R 3 are independently C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, OR 6 , or where R 4 and R 5 are as defined above except that said proviso does not apply, and R 6 is H or C 1 -C 4 alkyl, or one R 6 group may be with the proviso that both R 2 and R 3 may not be OH; and R 2 and R 3 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 R 7 -R 10 that have a total of up to four carbon atoms, viz. or and salts thereof with protic acids and complexes with metal ions.

Claim 4

A compound of the formula: wherein Q 1 , Q 2 and Q 3 are independently H or CH 3 ; n is 1; R' 1 is C 6 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl or where R 4 and R 5 are independently -H; halogen; -OCH 3 ; -OCF 3 ; -SCH 3 ; -S0 2 CH 3 ; phenyl; phenyl substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; phenoxy; phenoxy substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; -CF 3 ; C 1 -C 4 alkyl; or cyclohexyl; with the proviso that for compounds of Formula II, both R 4 and R 5 may not simultaneously be H; and R 2 and R 3 are independently C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, OR 6 , or where R 4 and R 5 are as defined above except that said proviso does not apply, and R 6 is H or C 1 -C 4 alkyl, or one R 6 group may be with the proviso that both R 2 and R 3 may not be OH; and R 2 and R 3 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 R 7 -R 10 that have a total of up to four carbon atoms, viz. or and salts thereof with protic acids and complexes with metal ions.

Claim 5

A compound of claim 1 or 2 wherein Q 1 and Q 2 are H .

Claim 6

A compound of claim 3 wherein R 1 or is R 2 is C 1 -C 4 alkyl or and R 3 is C 1 -C 4 alkyl.

Claim 7

A compound of claim 4 wherein R, and R are where R 4 is H, F, Cl, Br or phenyl, and R 5 is H, F, Cl or Br; and R 2 is or C 1 -C 4 alkyl; and R 3 is C 1 -C 4 alkyl.

Claim 8

The compound of Claim 1 which is (1,1'-biphenyl-4-yl)dimethyl(1H-1,2,4-triazol-1-ylmethyl)-silane.

Claim 9

The compound of Claim 1 which is bis(4-chlorophenyl)methyl(1H-1,2,4-triazol-1-ylmethyl)-silane.

Claim 10

8 . The compound of Claim 1 which is [bis(4-fluorophenyl)]methyl(1H-1,2,4-triazol-1-ylmethyl)-silane.

Claim 11

The compound of Claim 1 which is 4-fluorophenyl(methyl)phenyl(1H-1,2,4-triazol-1-ylmethyl)-silane.

Claim 12

The compound of claim 2 which is (2,4-dichlorophenyl)dimethyl(1H-imidazol-1-ylmethyl)silane.

Claim 13

A compound of claim 1 wherein: Q 1 and Q 2 are H; R 1 is C 2 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl, or where R 4 and R 5 are independently -H, halogen, phenyl, -OCH 3 , -SCH 3 , phenoxy, -CF 3 or C 1 -C 4 alkyl; and R 1 and R 3 are independently C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, or OR 6 , where R 6 is H or C 1 -C 4 alkyl.

Claim 14

A compound of claim 2 wherein Q 1 , Q 2 and Q 3 are H; R is where R 4 and R 5 are as defined in claim 11 but are not both H; and R 2 and R 3 are independently C 1 -C 4 alkyl or OR 6 , where R 6 is H or C 1 -C 4 alkyl.

Claim 15

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 1 to 12.

Claim 17

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 Q 1 , Q 2' Q 3 , n, R 2 , R 3 , and R 6 are as defined in claim 2, and R' 1 is C 2 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl or where R 4 and R 5 are independently -H; halogen; -OCH 3 ; 3; -SCH 3 ; -SO 2 CH 3 ; phenyl; phenyl substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; p henoxy; phenoxy substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; -CF 3 ; C 1 -C 4 alkyl; or cyclohexyl; or a salt thereof with a protic acid or a complex thereof with a metal ion.

Claim 18

A process for preparing a compound of claim 1 or 2 which comprises reacting a silane derivative of formula wherein R 1 , R , R 2 and R 3 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 wherein Q 1 and Q 2 are independently H or CH 3 and X is H, CH or CCH 3 , or with an alkali metal salt thereof.

Claim 19

A process for preparing a compound of claims 1 or 2 wherein R 2 and/or R 3 is OR 6 which comprises reacting a corresponding compound of formula wherein R is halogen or R 2 and R3 is halogen or R 3 , at least one of R 2 and R 3 being halogen, and Y is as defined in claim 15, with a triazole or imidazole sodium salt of formula wherein X is N, CH or CCH 3 , and reacting the intermediate so obtained with R 6 OH to obtain a compound of claim 1 or 2 wherein R 2 and/or R 3 is R 6 0; R 1 having a value as defined for R in claim 2 when X is CH or CCH 3 .

Claim 20

A process for preparing a compound of claim 1 which comprises reacting 1) an intermediate selected from the group. in a suitable solvent with R 1 M where M is Na, Li or MgX where X is Br, Cl, I, at a temperature of from -80° to 40°C to form a chloromethylsilane; and 2) reacting the 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 ketches at 0° to 200°C; R 1 , R 2 and R 3 being as defined in claim 1.

Claim 21

A process for preparing a compound of Claim 1 which comprises 1) reacting with R 6 OH in a suitable solvent with a suitable base at a temperature of 0°-100°C to form an alkoxy or dialkoxy chloromethylsilane; and 2) reacting the chloromethylsilanes 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; R 1 , R 2 and R 6 being: as defined in claim 1.

Claim 22

A process for preparing a compound of claim 2 which comprises reacting 1) an intermediate selected from the group in a suitable solvent with R M where M is Na, Li or MgX where X is Br, Cl, I, at a temperature of from -80° to 40°C to form a chloromethylsilane; and 2) reacting the 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; R , R 2 and R 3 being as defined in claim 2.

Claim 23

A process for preparing a compound of claim 2 which comprises 1) reacting with R 6 0H in a suitable solvent with a suitable base at a temperature of 0° to 100°C to form an alkoxy or dialkoxy chloromethylsilane; and 2) reacting the chloromethylsilane with imidazole, its 2-methyl, 2,4-methyl, 4,5-methyl, and 2,4,5-trimethyl derivatives, or their alkali metal salts in polar aprotic solvents, ethers or ketones at 0° to 200°C; R , R 2 and R 6 being as defined in claim 2.

Claim 24

A process for the preparation of a compound of the formula: wherein Q 1 and Q 2 are independently H or CH 3 ; n is 1; R 1 is C 2 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl, or where R 4 and R 5 are independently -H; halogen; -OCH 3 ; -OCF 3 -; -SCH 3 ; -SO 2 CH 3 ; phenyl; - phenyl substituted with halogen and/or C 1 -C 4 alkyl and/or -CF3; phenoxy; phenoxy substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; -CF 3 ; C 1 -C 4 alkyl; or cyclohexyl; R 2 and R 3 are independently C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, OR 6 , or where R 6 is H or C 1 -C 4 alkyl, or one R 6 group may be with the proviso that both R 2 and R 3 may not be OH; and R 2 and R 3 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 R 7 -R 10 that have a total of up to four carbon atoms, or and salts thereof with protic acids and complexes with metal ions, which comprises (a) reaction of a silane derivative of formula wherein R 1 , R 2 and R 3 are as defined above and Y is chlorine, bromine or arylsulfonyloxy, with a 1,2,4-triazole of formula wherein Q 1 and Q 2 are as defined above or with an alkali metal salt thereof; or (b) reacting a corresponding compound of formula wherein R 1 and Y are as defined above, R 2 is halogen or R 2 and R 3 is halogen or R 3 , at least one of R and R being halogen, with a triazole sodium salt of formula wherein Q 1 and Q 2 are as defined above, and reacting the intermediate so obtained with R 6 OH to obtain a product of formula I wherein R 2 and/or R 3 is R 6 O.

Claim 25

A process for the preparation of a compound of the formula: wherein Q 1 and Q 2 are independently H or CH 3 ; n is 1; R 1 is C 2 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl, or where R 4 and R 5 are independently -H; halogen; -OCH 3 ; -OCF 3 -; -SCH 3 ; -SO 2 CH 3 ; phenyl; - phenyl substituted with halogen and/or C 1 -C 4 alkyl and/or -CF3; phenoxy; phenoxy substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; -CF 3 ; C 1 -C 4 alkyl; or cyclohexyl; R 2 and R 3 are independently C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, OR 6 , or where R 6 is H or C 1 -C 4 alkyl, or one R 6 group may be with the proviso that both R 2 and R 3 may not be OH; and R 2 and R 3 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 R 7 -R 10 that have a total of up to four carbon atoms, or and salts thereof with protic acids and complexes with metal ions, which comprises (a) reaction of a silane derivative of formula wherein R 1 , R 2 and R 3 are as defined above and Y is chlorine, bromine or arylsulfonyloxy, with a 1,2,4-triazole of formula wherein Q 1 and Q 2 are as defined above or with an alkali metal salt thereof; or (b) reacting a corresponding compound of formula wherein R 1 and Y are as defined above, R 2 is halogen or R 2 and R 3 is halogen or R 3 , at least one of R and R being halogen, with a triazole sodium salt of formula wherein Q 1 and Q 2 are as defined above, and reacting the intermediate so obtained with R 6 OH to obtain a product of formula I wherein R 2 and/or R 3 is R 6 O.

Claim 26

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 in a suitable solvent with R 1 M where M is Na, Li or MgX where X is Br, Cl, I, at a temperature of from -80°C to 40°C to form a chloromethylsilane; and 2) reacting the chloromethylsilane with 1,2,4-triazole, its 3-methyl or 3,5-dimethyl derivative, or their alkali metal salts in polar aprotic solvents, ethers or ketones at 0° to 200°C; R 1 , R 2 and R 3 being as defined in claim 1.

Claim 27

The process of claim 1 or claim 2 wherein: Q 1 and Q 2 are H; R 1 is C 2 -C 18 alkyl,- C 3 -C 6 cycloalkyl, naphthyl, or where R 4 and R 5 are independently -H, halogen, phenyl,-OCH 3 , -SCH 3 , phenoxy, -CF 3 or C 1 -C 4 alkyl; and R 1 and R 3 are independently C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, or OR 6 , where R 6 is H or C 1 -C 4 alkyl.

Claim 28

A process for the preparation of a compound of the formula: wherein Q 1 , Q 2 and Q 3 are independently H or CH 3 ; n is 1; R' 1 is C 6 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl or where R 4 and R 5 are independently -H; halogen; -OCH 3 ; -OCF 3 ; -SCH 3 ; -S0 2 CH 3 ; phenyl; phenyl substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; phenoxy; phenoxy substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; -CF 3 ; C 1 -C 4 alkyl; or cyclohexyl; with the proviso that for compounds of Formula II, both R 4 and R 5 may not simultaneously be H; and R 2 and R 3 are independently C I -C 6 alkyl, C 3 -C 6 cycloalkyl, OR 6 , or where R 4 and R 5 are as defined above except that said proviso does not apply and R 6 is H or C 1 -C 4 alkyl, or one R 6 group may be with the proviso that both R 2 and R 3 may not be OH; and R 2 and R 3 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 R 7 -R 10 that have a total of up to four carbon atoms, viz or and salts thereof with protic acids and complexes with metal ions, which comprises (a) reacting a silane derivative of formula wherein R , R 2 and R 3 are as defined above and Y is chlorine, bromine, iodine or arylsulfonyloxy, with an imidazole of formula wherein Q 1 and Q 2 are as defined above, or with an alkali metal salt thereof, or (b) reacting a corresponding compound of formula wherein R and Y are as defined above, R is halogen or R 2 , R is halogen or R 3 , at least one of R and R being halogen, with an imidazole sodium salt of formula - wherein Q 1 and Q 2 are as defined above, and reacting the intermediate so obtained with R 6 OH to obtain a compound of formula II wherein R 2 and/or R 3 is R 6 O.

Claim 29

A process for the preparation of a compound of the formula: wherein Q 1 , Q 2 and Q 3 are independently H or CH 3 ; n is 1; R' 1 is C 6 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl or where R 4 and R 5 are independently -H; halogen; -OCH 3 ; -OCF 3 ; -SCH 3 ; -S0 2 CH 3 ; phenyl; phenyl substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; phenoxy; phenoxy substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; -CF 3 ; C 1 -C 4 alkyl; or cyclohexyl; with the proviso that for compounds of Formula II, both R 4 and R 5 may not simultaneously be H; and R 2 and R 3 are independently C I -C 6 alkyl, C 3 -C 6 cycloalkyl, OR 6 , or where R 4 and R 5 are as defined above except that said proviso does not apply and R 6 is H or C 1 -C 4 alkyl, or one R 6 group may be with the proviso that both R 2 and R 3 may not be OH; and R 2 and R 3 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 R 7 -R 10 that have a total of up to four carbon atoms, viz or and salts thereof with protic acids and complexes with metal ions, which comprises (a) reacting a silane derivative of formula wherein R , R 2 and R 3 are as defined above and Y is chlorine, bromine, iodine or arylsulfonyloxy, with an imidazole of formula wherein Q 1 and Q 2 are as defined above, or with an alkali metal salt thereof, or (b) reacting a corresponding compound of formula wherein R and Y are as defined above, R is halogen or R 2 , R is halogen or R 3 , at least one of R and R being halogen, with an imidazole sodium salt of formula - wherein Q 1 and Q 2 are as defined above, and reacting the intermediate so obtained with R 6 OH to obtain a compound of formula II wherein R 2 and/or R 3 is R 6 O.

Claim 30

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 in a suitable solvent with R M where M is Na, Li or MgX where X is Br, Cl; I, at a temperature of from -80°C to 40°C to form a chloromethylsilane; 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; R , R 2 and R 3 being as defined in claim 2. The process of claims 4 or 5 wherein Q 1 , Q 2 and Q 3 are H; R is where n 4 and R 5 are as defined in claim 3 but are not both H; and R 2 and R 3 are independently C 1 -C 4 alkyl or OR 6 , where R 6 is H or C 1 -C 4 alkyl.

Claim 31

The process of any of claims 1-6 wherein Q 1 and Q 2 are H, R 1 or R is R 2 is C 1 -C 4 alkyl or and R 3 is C 1 -C 4 alkyl.

Claim 32

The process of claim 7 wherein R 1 and R2 are where R 4 is H, F, Cl, Br or phenyl, and R 5 is H, F, Cl or Br; and R 2 is or C 1 -C 4 alkyl; and R 3 is C 1 -C 4 alkyl.

Claim 33

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-1-ylmethyl)-silane; bis(4-chlorophenyl)methyl(1H-1,2,4-triazol-1-ylmethyl)-silane; [bis(4-fluorophenyl)]methyl(1H-1,2,4-triazol-1-ylmethyl)-silane; 4-fluorophenyl(methyl)phenyl(1H-1,2,4-triazol-1-ylmethyl)-silane; and (2,4-dichlorophenyl)dimethyl(1H-imidazol-1-ylmethyl)silane.

Claim 36

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 : wherein Q 1 , Q 2' Q 3 , n, R 2 , R 3 and R 6 are as defined in claim 2, and R is C 2 -C 18 alkyl, C 3 -C 6 cycloalkyl, naphthyl or where R 4 and R 5 are independently -H; halogen; -OCH 3 ; -OCF 3 ; -SCH 3 ; -SO 2 CH 3 ; phenyl; phenyl substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; phenoxy; phenoxy substituted with halogen and/or C 1 -C 4 alkyl and/or -CF 3 ; -CF 3 ; C 1 -C 4 alkyl; or cyclohexyl; or a salt thereof with a protic acid or a complex thereof with a metal ion.