Claims
- 1. A process for making a compound having the formula: ##STR5## wherein R is:
- C.sub.1 -C.sub.12 alkyl,
- C.sub.2 -C.sub.13 alkoxyalkyl,
- C.sub.7 -C.sub.9 aralkyl,
- C.sub.5 -C.sub.6 cycloalkyl,
- C.sub.3 -C.sub.12 alkenyl,
- naphthyl,
- phenyl,
- phenyl substituted with at least one member selected from the group consisting of:
- fluorine,
- chlorine,
- bromine,
- iodine,
- C.sub.1 -C.sub.4 alkyl,
- C.sub.1 -C.sub.4 alkoxy,
- methylenedioxy,
- NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 are the same or different and are hydrogen or C.sub.1 -C.sub.6 alkyl,
- C.sub.2 -C.sub.5 alkoxycarbonyl,
- carboxy,
- phenoxy,
- nitro,
- cyano,
- trihalomethyl wherein halo is fluorine, chlorine or bromine,
- trihalomethoxy wherein halo is fluorine, chlorine or bromine,
- C.sub.1 -C.sub.6 alkylthio, and
- C.sub.1 -C.sub.6 fluoroalkylthio; or
- benzyl substituted with at least one member selected from the group consisting of:
- fluorine,
- chlorine,
- bromine,
- iodine,
- C.sub.1 -C.sub.4 alkyl,
- C.sub.1 -C.sub.4 alkoxy,
- methylenedioxy,
- C.sub.2 -C.sub.5 alkoxycarbonyl,
- phenoxy,
- nitro,
- cyano,
- trihalomethyl wherein halo is fluorine, chlorine or bromine,
- trihalomethoxy wherein halo is fluorine, chlorine or bromine,
- C.sub.1 -C.sub.6 alkylthio, and
- C.sub.1 -C.sub.6 fluoroalkylthio;
- R.sup.1 and R.sub.2 are the same or different and are
- C.sub.1 -C.sub.6 alkyl,
- C.sub.3 -C.sub.6 alkenyl,
- C.sub.5 -C.sub.6 cycloalkyl,
- C.sub.7 -C.sub.9 aralkyl,
- C.sub.7 -C.sub.9 aralkyl substituted with at least one member selected from the group consisting of:
- fluorine,
- chlorine,
- bromine,
- iodine,
- C.sub.1 -C.sub.6 alkyl,
- C.sub.1 -C.sub.2 haloalkyl wherein halo is fluorine, chlorine or bromine,
- halomethoxy wherein halo is fluorine, chlorine or bromine,
- C.sub.1 -C.sub.6 alkoxy,
- C.sub.1 -C.sub.6 alkylthio,
- C.sub.1 -C.sub.6 fluoroalkylthio,
- phenoxy,
- phenylthio,
- carboxy,
- C.sub.2 -C.sub.5 alkoxycarbonyl,
- methylenedioxy,
- nitro,
- cyano, and
- NR.sup.7 R.sup.8 wherein R.sup.7 and R.sup.8 are the same or different and are hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.4 -C.sub.8 alkylene or C.sub.4 -C.sub.8 oxydialkylene;
- naphthyl,
- phenyl, or
- phenyl substituted with at least one member selected from the
- group consisting of:
- fluorine,
- chlorine,
- bromine,
- iodine,
- C.sub.1 -C.sub.6 alkyl,
- C.sub.1 -C.sub.2 haloalkyl wherein halo is fluorine, chlorine or bromine;
- halomethoxy wherein halo is fluorine, chlorine or bromine,
- C.sub.1 C.sub.6 alkoxy,
- C.sub.1 -C.sub.6 alkylthio,
- C.sub.1 -C.sub.6 fluoroalkylthio,
- phenoxy,
- phenyl,
- phenylthio,
- carboxy,
- C.sub.2 -C.sub.5 alkoxycarbonyl,
- C.sub.1 -C.sub.2 alkylenedioxy, optionally substituted with 1-2 methyl groups,
- C.sub.1 -C.sub.2 alkyleneoxy, optionally substituted with 1-2 methyl groups,
- nitro,
- cyano, and
- NR.sup.7 R.sup.8 wherein R.sup.7 and R.sup.8 are the same or different and are hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.4 -C.sub.8 alkylene or C.sub.4 -C.sub.8 oxydialkylene; or
- R.sup.1 and R.sub.2 together are C.sub.4 -C.sub.8 alkylene or C.sub.4 -C.sub.8 oxydialkylene,
- with the proviso that when R is other than C.sub.3 -C.sub.12 alkenyl, C.sub.1 -C.sub.6 alkylthio-substituted phenyl, C.sub.1 -C.sub.6 alkylthio-substituted benzyl, C.sub.1 -C.sub.6 fluoroalkylthio-substituted phenyl or benzyl and wherein at least one of R.sup.1 and R.sub.2 is C.sub.7 -C.sub.9 aralkyl, C.sub.7 -C.sub.9 substituted aralkyl phenyl or substituted phenyl, wherein substitution is as indicated above,
- comprising: the step of reacting, in an inert solvent at a temperature range from about 40.degree. C. up to the boiling point of said solvent a tetrazolinone compound having the formula: ##STR6## wherein R has the meanings given above and wherein M is hydrogen with an alkali metal carbonate to form an intermediate of the formula above wherein M is Li, Na or K followed by the reaction of said intermediate with a carbamoyl halide having the formula XCONR.sup.1 R.sup.2, wherein X is chlorine or bromine and R.sup.1 and R.sub.2 have the meanings above.
- 2. A process in accordance with claim 1 where the equivalent ratio of X/M is in the range of 0.75 to 2/1.
- 3. A process in accordance with claim 1 wherein said equivalent ratio of X/M is in the range of 0.9 to 1.5/1.
Parent Case Info
This is a division application of U.S. patent application Ser. No. 737,371 filed May 23, 1985, U.S. Pat. No. 4,826,529 which is a continuation of copending U.S. patent application Ser. No. 560,031 filed Dec. 9, 1983, now U.S. Pat. No. 4,618,365.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4618365 |
Covey et al. |
Oct 1986 |
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4826529 |
Covey et al. |
May 1989 |
|
4830661 |
Covey et al. |
May 1989 |
|
Non-Patent Literature Citations (1)
Entry |
T. Price, J. Chem. Soc. (1926) pp. 3230-3233. |
Divisions (1)
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Number |
Date |
Country |
Parent |
737371 |
May 1985 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
560031 |
Dec 1983 |
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