Benzyl-pyrimidinylalkyl-ethers as plant growth regulators and fungicides, and corresponding pyrimidinyl-carbinols

Abstract

A benzyl-pyrimidinylalkyl-ether of the formula ##STR1## in which R is alkyl, optionally substituted cycloalkyl or optionally substituted phenyl, and X 1 , X 2 and X 3 each independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, cyano, optionally substituted phenoxy, optionally substituted phenylalkyl or optionally substituted phenylalkoxy, or an acid addition salt or metal salt complex thereof, which possesses fungicidal and plant growth-regulating properties. The corresponding pyrimidinyl-carbinols are also new.

We claim: 
     
       1. A benzyl-pyrimidinylalkyl-ether of the formula ##STR39## in which R is alkyl having 1 to 8 carbon atoms; cycloalkyl which has 3 to 7 carbon atoms and which is optionally substituted by alkyl having 1 to 4 carbon atoms; or phenyl which is optionally substituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms and/or halogenoalkyl having 1 .[.to.]. .Iadd.or .Iaddend.2 carbon atoms and 1 to 5 halogen atoms, .[.having 1 to 2 carbon atoms and 1 to 5 halogen atoms.]., X 1  is hydrogen, halogen, alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally sustituted by halogen and/or by alkyl having 1 to 4 carbon atoms, phenoxy which is optionally substituted by halogen and/or by alkyl having 1 to 4 carbon atoms, phenylalkyl which has 1 to 4 carbon atoms in the alkyl part and which is optionally substituted in the phenyl part by halogen and/or by alkyl having 1 to 4 carbon atoms, or phenylalkoxy which has 1 to 4 carbon atoms in the alkoxy part and which is optionally substituted in the phenyl part by halogen and/or by alkyl having 1 to 4 carbon atoms, and   X 2  and X 3  each independently is hydrogen, halogen, alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms or halogenoalkyl, halogenoalkoxy or halogenoalkylthio each having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or an acid addition salt or metal salt complex thereof.     
     
     
       2. A compound according to claim 1, in which R is alkyl with 1 to 8 carbon atoms, cycloalkyl with 3 to 7 carbon atoms or phenyl,   X 1  is hydrogen, halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms or phenyl,   X 2  is hydrogen or halogen, and   X 3  is hydrogen or a hydrochloric acid addition salt thereof.     
     
     
       3. A compound according to claim 1 in which R is isopropyl, isobutyl, tert.-butyl, n-pentyl, n-hexyl, optionally methyl-substituted cyclopentyl or cyclohexyl, or phenyl which is optionally substituted by fluorine, chlorine, methyl, methoxy or trifluoromethyl,   X 1  is hydrogen, fluorine, chlorine, methyl, tert.-butyl, cyclohexyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, cyano, or phenyl, phenoxy, benzyl or benzyloxy, each of which is optionally substituted by fluorine, chlorine or methyl,   X 2  is hydrogen, fluorine, chlorine, methyl, tert.-butyl, cyclohexyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, and   X 3  is hydrogen, fluorine, chlorine, methyl, methoxy, methyl or trifluoromethyl, or an addition salt thereof with a hydrohalic acid, phosphoric acid, nitric acid, sulphuric acid, a sulphonic acid or a monofunctional or bifunctional carboxylic or hydroxycarboxylic acid, or a complex thereof with a salt, the metal of the salt being copper, zinc, manganese, magnesium, tin, iron or nickel and the anion of the salt being halide, phosphate or sulphate.     
     
     
       4. A compound according to claim 1, wherein such compound is 5-[1-(4-chlorobenzyloxy)-2,2-dimethylpropyl]-pyrimidine of the formula ##STR40## 
     
     
       5. A compound according to claim 1, wherein such compound is 5-[1-(4-methoxybenzyloxy)-2,2-dimethylpropyl]-pyrimidine of the formula ##STR41## 
     
     
       6. A compound according to claim 1, wherein such compound is 5-[1-(2-chloro-6-fluorobenzyloxy)-2,2-dimethylpropyl]-pyrimidine of the formula ##STR42## 
     
     
       7. A compound according to claim 1, wherein such compound is 5-[1-(4-fluorobenzyloxy)-2,2-dimethylpropyl]-pyrimidine of the formula ##STR43## 
     
     
       8. A compound according to claim 1, wherein such compound is 5-[1-(2,4-dichlorobenzyloxy)-2,2-dimethylpropyl]-pyrimidine of the formula ##STR44##  .Iadd. 
     
     
       9.  A compound of the formula ##STR45## wherein R is benzyl; benzyl substituted on the aryl ring with 1 to 3 of the same or different halo, lower alkoxy, lower alkyl, or lower alkyl substituted with 1 to 5 of the same or different halogens; phenylbenzyl; or phenylbenzyl substituted in the benzene rings with halo or lower alkyl; R 1  is alkyl having 1 to 8 carbon atoms, phenyl or phenyl substituted with substituents selected from halo, C 1-4  -alkoxy or C 1-2  -alkyl substituted with the same or different halogens. .Iaddend. .Iadd.   
     
     
       10.  A compound of the formula described in claim 9 wherein R 1  is phenyl or phenyl substituted with substituents selected from halo, C 1-4  -alkoxy or C 1-2  -alkyl substituted with the same or different halogens. .Iaddend. .Iadd.11. A compound of the formula described in claim 10 werein R is benzyl or benzyl substituted on the aromatic ring with 1 to 5 of the same or different substituents selected from halo, lower alkoxy, lower alkyl or lower alkyl substituted with 1 to 
     
     
        5 of the same or different halogens. .Iaddend. .Iadd.12.  A compound of the formula described in claim 10 wherein R 1  is chlorophenyl. .Iaddend. .Iadd.13. A compound of the formula described in claim 12 wherein R is 2,4-dichlorobenzyl. .Iaddend. .Iadd.14. A compound of the formula described in claim 12 wherein R is trifluoromethylbenzyl. .Iaddend.