# US 4,398,941 A · Herbicidal composition and method > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,398,941 A - Document ID: US4398941A - Status: Granted - Kind: A - Application number: 06/356,010 - Filed: 1982-03-08 - Granted: 1983-08-16 - Earliest claimed: 1982-03-08 - Assignees: Monsanto Company - Inventors: Robert K. Howe; Len F. Lee - Web page: https://patentgrep.com/patent/US4398941A ## CPC - C07D 279/12: not condensed with other rings - A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4 - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS ## Abstract The invention herein pertains to dialkyl 3,5-bis(perfluoroalkyl)-2H-1,4-thiazine-2,6-dicarboxylates, a method for preparing the compounds and to herbicidal compositions and methods utilizing said compounds. ## Claims ### Claim 1 A compound represented by the formula ##STR5## wherein R is selected from the group consisting of H and lower alkyl radicals and R.sub.1 represents a perfluoroalkyl radical having from 1 to 3 carbon atoms. ### Claim 2 (depends on 1) A compound of claim 1 wherein R is ethyl and R.sub.1 is perfluoroethyl. ### Claim 3 (depends on 1) A compound of claim 1 wherein R is ethyl and R.sub.1 is trifluoromethyl. ### Claim 4 (depends on 1) A compound of claim 1 wherein R is hydrogen and R.sub.1 is perfluoroethyl. ### Claim 5 (depends on 1) A compound of claim 1 wherein R is hydrogen. ### Claim 6 (depends on 1) A compound of claim 1 wherein R is lower alkyl. ### Claim 7 (depends on 1) A compound of claim 1 wherein R is ethyl and R.sub.1 is perfluoropropyl. ### Claim 8 (depends on 1) A compound of claim 1 wherein R is butyl and R.sub.1 is perfluoroethyl. ### Claim 9 (depends on 1) A compound of claim 1 wherein R is methyl and R.sub.1 is perfluoroethyl. ### Claim 10 Herbicidal compositions comprising an adjuvant and a herbicidally effective amount of a compound represented by the formula ##STR6## wherein R is selected from the group consisting of H and lower alkyl radicals and R.sub.1 represents a perfluoroalkyl radical having from 1 to 3 carbon atoms. ### Claim 11 (depends on 10) A composition of claim 10 wherein R is ethyl and R.sub.1 is perfluoroethyl. ### Claim 12 (depends on 10) A composition of claim 10 wherein R is ethyl and R.sub.1 is trifluoromethyl. ### Claim 13 (depends on 10) A composition of claim 10 wherein R is hydrogen and R.sub.1 is perfluoroethyl. ### Claim 14 (depends on 10) A composition of claim 10 wherein R is hydrogen. ### Claim 15 (depends on 10) A composition of claim 10 wherein R is lower alkyl. ### Claim 16 (depends on 10) A composition of claim 10 wherein R is ethyl and R.sub.1 is perfluorpropyl. ### Claim 17 (depends on 10) A composition of claim 10 wherein R is butyl and R.sub.1 is perfluoroethyl. ### Claim 18 (depends on 10) A composition of claim 10 wherein R is methyl and R.sub.1 is perfluoroethyl. ### Claim 19 A method for controlling the growth of undesirable plants which comprises applying to the locus of the seed a herbicidal amount of a compound represented by the formula ##STR7## wherein R is selected from the group consisting of H and lower alkyl radicals and R.sub.1 represents a perfluoroalkyl radical having from 1 to 3 carbon atoms. ### Claim 20 (depends on 19) A method of claim 19 wherein R is ethyl and R.sub.1 is perfluoroethyl. ### Claim 21 (depends on 19) A method of claim 19 wherein R is ethyl and R.sub.1 is trifluoromethyl. ### Claim 22 (depends on 19) A method of claim 19 wherein R is hydrogen or lower alkyl. ### Claim 23 (depends on 19) A method of claim 19 wherein R is ethyl and R.sub.1 is perfluoropropyl. ### Claim 24 (depends on 19) A method of claim 19 wherein R is methyl and R.sub.1 is perfluoroethyl. ### Claim 25 A method for controlling the growth of undesirable plants which comprises applying to the plant a herbicidally effective amount of a compound represented by the formula ##STR8## wherein R is selected from the group consisting of H and lower alkyl radicals and R.sub.1 represents a perfluoroalkyl radical having from 1 to 3 carbon atoms. ### Claim 26 (depends on 25) A method of claim 25 wherein R is ethyl and R.sub.1 is perfluoroethyl. ### Claim 27 (depends on 25) A method of claim 25 wherein R is ethyl and R.sub.1 is trifluoromethyl. ### Claim 28 (depends on 25) A method of claim 25 wherein R is hydrogen. ### Claim 29 (depends on 25) A method of claim 25 wherein R is lower alkyl. ### Claim 30 (depends on 25) A method of claim 25 wherein R is ethyl and R.sub.1 is perfluoropropyl. ### Claim 31 (depends on 25) A method of claim 25 wherein R is methyl and R.sub.1 is perfluroroethyl. ### Claim 32 (depends on 25) A method of claim 25 wherein R is butyl and R.sub.1 is perfluoroethyl. ### Claim 33 (depends on 1) A process for the preparation of a compound of claim 1 which comprises reacting a sulfur chloride selected from the group consisting of sulfur monochloride and sulfur dichloride with a 3-perfluoroalkyl-3-amino acrylate represented by the structural formula ##STR9## wherein R is selected from the group consisting of H and lower alkyl radicals and R.sub.1 represents a perfluoroalkyl radical having from 1 to 3 carbon atoms. ### Claim 34 (depends on 33) The process of claim 33 wherein the 3-perfluoroalkyl-3-aminoacrylate is added to a reaction vessel containing said sulfur chloride. ### Claim 35 (depends on 33) The process of claim 33 wherein the sulfur monochloride is added to a reaction vessel containing said aminoacrylate. ### Claim 36 (depends on 33) A process of claim 33 wherein R is ethyl and R.sub.1 is perfluoroethyl. ### Claim 37 (depends on 33) A process of claim 33 wherein R is ethyl and R.sub.1 is trifluoromethyl. ### Claim 38 (depends on 33) A process of claim 33 wherein R is methyl and R.sub.1 is perfluoroethyl. ### Claim 39 (depends on 33) A process of claim 33 where R is ethyl and R.sub.1 is perfluoropropyl. ### Claim 40 (depends on 33) A process of claim 33 wherein R is hydrogen. ### Claim 41 (depends on 33) A process of claim 33 wherein R is lower alkyl. ### Claim 42 A compound represented by the formula ##STR10## wherein R is selected from the group consisting of H and lower alkyl radicals and R.sub.1 represents a perfluoroalkyl radical. ### Claim 43 Diethyl 3-amino-3,5-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-thiazine-2,6-dicarboxy late. ### Claim 44 (depends on 42) A method for controlling the growth of undesirable plants which comprises applying to the locus of the seed a herbicidal amount of a compound of claim 42. ### Claim 45 (depends on 44) A method of claim 44 wherein the compound is diethyl 3-amino-3,5-bis(trifluoromethyl)3,4-dihydro-2H-1,4-thiazine-2,6-dicarboxyl ate. ### Claim 46 (depends on 42) A method for controlling the growth of undesirable plants which comprises applying to the plant a herbicidal amount of a compound of claim 42. ### Claim 47 (depends on 46) A method of claim 46 wherein the compound is diethyl 3-amino-3,5-bis(trifluoromethyl)3,4-dihydro-2H-1,4-thiazine-2,6-dicarboxyl ate. ### Claim 48 A herbicidal composition comprising an adjuvant and a herbicidally effective amount of a compound represented by the formula ##STR11## ### Claim 49 (depends on 48) A composition of claim 48 wherein said compound is diethyl 3-amino-3,5-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-thiazine-2,6-dicarboxy late.