N-arylcarbamic acid esters

Abstract

New N-arylcarbamic acid esters of the formula ##STR1## in which R is lower aliphatic hydrocarbyl, optionally substituted, R 1 , R 2 and R 3 , which may be identical or different, are each hydrogen, alkyl, cycloalkyl, alkoxy, haloalkyl or halogen, R 4 is alkyl, alkenyl, cycloalkenyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl or alkylthioalkyl, acylalkyl (i.e., alkanoyloxyalkyl), alkoxycarbonylalkyl, carbalkoxyalkyl, carbalkoxyalkenyl, or an optionally substituted cycloalkyl, aryl, aralkyl, aryloxyalkyl or arylthioalkyl radical, or the grouping ##STR2## wherein R 4' is hydrogen or is defined as R 4 is defined above, and Y and Y' are oxygen or sulfur, are outstandingly effective in regulating the growth of plants, i.e., to inhibit, stimulate or alter the growth of plants.

What is claimed is: 
     
       1. N-arylcarbamate of the formula: ##STR64## wherein R is alkyl of from one to four carbon atoms; alkenyl of from three to six carbon atoms; alkynyl of from three to six carbon atoms; cycloalkyl of from five to eight carbon atoms; hydroxyalkyl of from two to four carbon atoms; hydroxyalkenyl or hydroxyalkynyl of from three to six carbon atoms; alkoxyalkyl of from one to four carbon atoms in the alkoxy moiety and two to four carbon atoms in the alkyl moiety; chloro alkyl of from one to four carbon atoms and one to three chlorine atoms; chloroalkenyl or chloroalkynyl of from three to six carbon atoms and one to three chlorine atoms; or aralkyl of from one to four carbon atoms in the alkyl moiety and six to 10 carbon atoms in the aryl moiety wherein the aryl moiety may carry at least one of fluorine, chlorine, and bromine, alkyl of from one to four carbon atoms, chloroalkyl of from one to four carbon atoms and one to three chlorine atoms, alkoxy of from up to 4 carbon atoms and nitro;   R 1 , R 2  and R 3  are individually selected from the group consisting of hydrogen, fluorine, chlorine, bromine, alkyl of from one to four carbon atoms, cycloalkyl of from five to seven carbon atoms, alkoxy of from one to four carbon atoms, chloroalkyl of from one or two carbon atoms and two to five chlorine atoms;   R 4  is the grouping ##STR65## wherein R 4'  is hydrogen, alkyl of from one to 17 carbon atoms; alkenyl of from three to 10 carbon atoms; alkynyl of from three to six carbon atoms; chloroalkyl of from one to six carbon atoms and one to three chlorine atoms; chloroalkenyl of from three to six carbon atoms and one to four chlorine atoms; chloroalkynyl of from three to six carbon atoms and one to four chlorine atoms; or alkoxyalkyl, alkylthioalkyl methylcarbonylalkyl, methoxycarbonylalkyl of from one to four carbon atoms per alkyl moiety; cycloalkyl of from three to eight carbon atoms, cycloalkenyl of from five to six carbon atoms; aryl, aralkyl, or aroxyalkyl of from six to 10 carbon atoms in the aryl moiety and one to four carbon atoms in the alkyl moiety, wherein said aryl moiety may carry at least one of fluorine, chlorine and bromine, alkyl or alkoxy of from one to four carbon atoms and chloroalkyl of from one or two carbon atoms and one to five chlorine atoms, and wherein the alkyl moiety of said aralkyl may be substituted with chlorine and   Y and Y' are oxygen.   
     
     
       2. Compound as claimed in claim 1 wherein R is alkyl of about four carbon atoms. 
     
     
       3. Compound as claimed in claim 1 wherein R is alkenyl or alkynyl of from three to six carbon atoms. 
     
     
       4. Compound as claimed in claim 1 wherein R is cycloalkyl of from five to eight ring carbon atoms. 
     
     
       5. Compound as claimed in claim 1 wherein R is hydroxyalkyl of from two to four carbon atoms, hydroxyalkenyl or hydroxyalkynyl of from three up to six carbon atoms. 
     
     
       6. Compound as claimed in claim 1 wherein R is alkoxyalkyl of up to four carbon atoms in each alkyl moiety. 
     
     
       7. Compound as claimed in claim 1 wherein R is chloroalhyl chloroalkenyl and chloroalkynyl of up to six carbon atoms and from one to three halogen atoms. 
     
     
       8. Compound as claimed in claim 1 wherein R is aralkyl of from one to four carbon atoms in the alkyl moiety and six to 10 carbon atoms in the aryl moiety, wherein the aryl moiety may be substituted with at least one member selected from the group consisting of halogen, alkyl of from one to four carbon atoms, haloalkyl of from one to four carbon atoms and one to three halogen atoms, alkoxy of from one to four carbon atoms and nitro. 
     
     
       9. Compound as claimed in claim 1 wherein R 1 , R 2  and R 3  are individually selected from the group consisting of hydrogen, fluorine, chlorine, bromine, alkyl with one to four carbon atoms, cycloalkyl with five to seven carbon atoms, straightchain or branched alkoxy with one to four carbon atoms or chloroalkyl with one or two carbon atoms and two to five chlorine atoms. .[.10. Compound as claimed in claim 1 designated Methyl-N-methoxymethyl-N-phenyl carbamate..]. .[.11. Compound as claimed in claim 1 designated Methyl-N-ethoxymethyl-N-phenyl carbamate..]. .[.12. Compound as claimed in claim 1 designated Methyl-N-isopropoxymethyl-N-phenyl carbamate..]. .[.13. Compound as claimed in claim 1 designated Methyl-N-n-butoxymethyl-N-phenyl 
     
     
        carbamate..]. .[.14.  Compound as claimed in claim 1 designated Isopropyl-N-methoxymethyl-N-phenyl carbamate..]. .[.15. Compound as claimed in claim 1 designated Isopropyl-N-ethoxymethyl-N-phenyl carbamate..]. .[.16. Compound as claimed in claim 1 designated 
     
     
        Isopropyl-N-n-propoxymethyl-N-phenyl carbamate..]. 17. Compound as claimed in claim 1 designated Isopropyl-chloroacetoxymethyl-N-phenyl carbamate. 
     
     
            Compound as claimed in claim 1 designated 
     
     
        Isopropyl-N-acetoxymethyl-N-3-chlorophenyl carbamate. 19. Compound as claimed in claim 1, designated isopropyl-N-n-propanoyl-oxymethyl-N-(3-chlorophenyl)-carbamate.