# US 4,395,276 A · Thiosulfenamide derivatives of N-phosphonomethylglycinonitriles as herbicides > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,395,276 A - Document ID: US4395276A - Status: Granted - Kind: A - Application number: 06/309,323 - Filed: 1981-10-05 - Granted: 1983-07-26 - Earliest claimed: 1980-06-18 - Assignees: Monsanto Company - Inventors: James A. Sikorski; Tommie G. Curtis - Web page: https://patentgrep.com/patent/US4395276A ## CPC - A01M 7/005: {Special arrangements or adaptations of the spraying or distributing parts, e.g. adaptations or mounting of the spray booms, mounting of the nozzles, protection shields (nozzles, spray heads or other outlets B05B1/00; spray pistols B05B9/01)} - C07F 9/4006: {Esters of acyclic acids which can have further substituents on alkyl} - A01M: CATCHING, TRAPPING OR SCARING OF ANIMALS (appliances for catching swarms or drone-catching A01K57/00; fishing A01K69/00 - {A01K99/00}; biocides, pest repellants or attractants A01N); APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) ## Abstract This invention relates to alkyl, cycloalkyl, aryl, and araloweralkyl thiosulfenamide derivatives of N-phosphonomethylglycinonitriles which are useful as herbicides and a process for producing the same. This invention further relates to herbicidal compositions containing such derivatives and to herbicidal methods employing such compounds and compositions. ## Claims ### Claim 1 A method of controlling undesired plants which comprises applying to said plants or plant growth medium a herbicidally effective amount of a compound of the formula ##STR8## wherein R is selected from the group consisting of phenyl, naphthyl or biphenylyl; or phenyl, naphthyl or biphenylyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, alkoxycarbonyl, methylenedioxy, trifluoromethyl, cyano, nitro and halogen; and R.sub.1 is alkyl, aralower alkyl, cycloalkyl, naphthyl or phenyl or phenyl or naphthyl or aralower alkyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, and trifluoromethyl. ### Claim 2 (depends on 1) A method according to claim 1 wherein R is phenyl or phenyl substituted. ### Claim 3 (depends on 2) A method according to claim 2 wherein R.sub.1 is phenyl or phenyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogen and trifluoromethyl. ### Claim 4 (depends on 2) A method according to claim 2 wherein R.sub.1 is alkyl or cycloalkyl or aralower alkyl. ### Claim 5 (depends on 4) A method according to claim 4 wherein R.sub.1 is isopropyl. ### Claim 6 (depends on 4) A method according to claim 4, wherein R.sub.1 is tertiary butyl. ### Claim 7 (depends on 4) A method according to claim 4, wherein R.sub.1 is n-octyl. ### Claim 8 (depends on 4) A method according to claim 4, wherein R.sub.1 is cyclohexyl. ### Claim 9 (depends on 4) A method according to claim 4, wherein R.sub.1 is phenylethyl. ### Claim 10 (depends on 4) A method according to claim 4 wherein said compound is phosphonic acid, [[(cyanomethyl)[(1,1-dimethylethyl)dithio]amino]methyl]-, diphenyl ester. ### Claim 11 (depends on 4) A method according to claim 4 wherein said compound is phosphonic acid, [[(cyanomethyl)[(1,1-dimethylethyl)dithio]amino]methyl]-, bis(4-methoxyphenyl)ester. ### Claim 12 (depends on 4) A method according to claim 4 wherein said compound is phosphonic acid, [[(cyanomethyl)[(methyl)dithio]amino]methyl]-, diphenyl ester. ### Claim 13 (depends on 4) A method according to claim 4 wherein said compound is phosphonic acid, [[(cyanomethyl)[(2-phenylethyl)dithio]amino]methyl]-, diphenyl ester. ### Claim 14 A compound of the formula ##STR9## wherein R is selected from the group consisting of phenyl, naphthyl or biphenylyl; or phenyl, naphthyl or biphenylyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, alkoxycarbonyl, methylenedioxy, trifluoromethyl, cyano, nitro and halogen; and R.sub.1 is independently alkyl, aralower alkyl, cycloalkyl, phenyl, naphthyl or phenyl or naphthyl or aralower alkyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, and trifluoromethyl. ### Claim 15 (depends on 14) A compound according to claim 14 wherein R is phenyl or phenyl substituted. ### Claim 16 (depends on 15) A compound according to claim 15 wherein R.sub.1 is phenyl or phenyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogen and trifluoromethyl. ### Claim 17 (depends on 15) A compound according to claim 15 wherein R.sub.1 is alkyl or cycloalkyl or aralower alkyl. ### Claim 18 (depends on 17) A compound according to claim 17 wherein R.sub.1 is isopropyl. ### Claim 19 (depends on 17) A compound according to claim 17 wherein R.sub.1 is tertiary butyl. ### Claim 20 (depends on 17) A compound according to claim 17 wherein R.sub.1 is n-octyl. ### Claim 21 (depends on 17) A compound according to claim 17 wherein R.sub.1 is cyclohexyl. ### Claim 22 (depends on 17) A compound according to claim 17 wherein R.sub.1 is phenylethyl. ### Claim 23 (depends on 17) A compound according to claim 17 wherein the compound is phosphonic acid, [[(cyanomethyl)[(1,1-dimethylethyl)dithio]amino]methyl]-, diphenyl ester. ### Claim 24 (depends on 17) A compound according to claim 17 wherein the compound is phosphonic acid, [[(cyanomethyl)[(1,1-dimethylethyl)dithio]amino]methyl]-, bis(4-methoxyphenyl)ester. ### Claim 25 (depends on 17) A compound according to claim 17 wherein the compound is phosphonic acid, [[(cyanomethyl)[(methyl)dithio]amino]methyl]-, diphenyl ester. ### Claim 26 (depends on 17) A compound according to claim 17 wherein the compound is phosphonic acid, [[(cyanomethyl)[(2-phenylethyl)dithio]amino]methyl]-, diphenyl ester. ### Claim 27 A herbicidal composition comprising an inert adjuvant and a herbicidally effective amount of a compound of the formula ##STR10## wherein R is selected from the group consisting of phenyl, naphthyl or biphenylethyl; or phenyl, naphthyl or biphenylyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, alkoxycarbonyl, methylenedioxy, trifluoromethyl, cyano, nitro and halogen; and R.sub.1 is alkyl, aralower alkyl, cycloalkyl, naphthyl or phenyl or phenyl or naphthyl or aralower alkyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, and trifluoromethyl. ### Claim 28 (depends on 27) A composition according to claim 27 wherein said compound is a compound wherein R is phenyl or phenyl substituted. ### Claim 29 (depends on 28) A composition according to claim 28 wherein said compound is a compound wherein R.sub.1 is phenyl or phenyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogen and trifluoromethyl. ### Claim 30 (depends on 28) A composition according to claim 28 wherein said compound is a compound wherein R.sub.1 is alkyl or cycloalkyl or aralower alkyl. ### Claim 31 (depends on 30) A composition according to claim 30 wherein R.sub.1 is isopropyl. ### Claim 32 (depends on 30) A composition according to claim 30 wherein R.sub.1 is tertiary butyl. ### Claim 33 (depends on 30) A composition according to claim 30 wherein R.sub.1 is n-octyl. ### Claim 34 (depends on 30) A composition according to claim 30 wherein R.sub.1 is cyclohexyl. ### Claim 35 (depends on 30) A composition according to claim 30 wherein R.sub.1 is phenylethyl. ### Claim 36 (depends on 30) A composition according to claim 30 wherein said compound is phosphonic acid, [[(cyanomethyl)[1,1-dimethylethyl)dithio]amino]methyl]-, diphenyl ester. ### Claim 37 (depends on 30) A composition according to claim 30 wherein said compound is phosphonic acid, [[(cyanomethyl)[(1,1-dimethylethyl)dithio]amino]methyl]-, bis(4-methoxyphenyl)ester. ### Claim 38 (depends on 30) A composition according to claim 30 wherein said compound is phosphonic acid, [[(cyanomethyl)[(methyl)dithio]amino]methyl]-, diphenyl ester. ### Claim 39 (depends on 30) A composition according to claim 30 wherein said compound is phosphonic acid, [[(cyanomethyl)[(2-phenyl-ethyl)dithio]amino]methyl]-, diphenyl ester.