# US 4,400,200 A · Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines - herbicidal antidotes > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,400,200 A - Document ID: US4400200A - Status: Granted - Kind: A - Application number: 06/317,957 - Filed: 1981-11-04 - Granted: 1983-08-23 - Earliest claimed: 1975-02-14 - Assignees: Stauffer Chemical Company - Inventors: Eugene G. Teach - Web page: https://patentgrep.com/patent/US4400200A ## CPC - C07D 263/04: having no double bonds between ring members or between ring members and non-ring members - C07D 277/04: having no double bonds between ring members or between ring members and non-ring members - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines useful as active antidotes against crop injury when used with various herbicides; herbicidal compositions and utility of various herbicides and aryl substituted oxazolidines and thiazolidines having the formula ##STR1## wherein X and Y are independently oxygen or sulfur; R is haloalkyl or chloroalkenyl; R.sub.1 is hydrogen, lower alkyl, phenyl, naphthyl, substituted phenyl wherein said substituents are monofluoro, mono- or di- chloro, nitro, methyl, methoxy, or hydroxyl; R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen, lower alkyl, hydroxymethyl, N-methyl carbamoyloxymethyl or dichloroacetoxymethyl; R.sub.4 is hydrogen or lower alkyl; R.sub.5 is hydrogen, lower alkyl or phenyl; and R.sub.6 is hydrogen; provided that at least one of R.sub.1 or R.sub.5 is phenyl, substituted phenyl or naphthyl. ## Claims ### Claim 1 An herbicidal composition comprising an active thiolcarbamate herbicidal compound and a non-phytotoxic antidotally effective amount of antidote therefor corresponding to the formula ##STR11## wherein R is haloalkyl having 1 to 6 carbon atoms, inclusive, halo is chloro or bromo or chloroalkenyl; R.sub.1 is hydrogen, lower alkyl having 1 to 4 carbon atoms, inclusive, phenyl, naphthyl, substituted phenyl wherein said substituents are mono-fluoro, mono- or di-chloro, nitro, methyl, methoxy, or hydroxyl; R.sub.2 is hydrogen or lower alkyl having 1 to 4 carbon atoms, inclusive; R.sub.3 is hydrogen, hydroxymethyl, N-methylcarbamoyloxymethyl or dichloroacetoxymethyl; R.sub.4 is hydrogen, or lower alkyl having 1 to 4 carbon atoms, inclusive; R.sub.5 is hydrogen, lower alkyl having 1 to 4 carbon atoms, inclusive or phenyl; and R.sub.6 is hydrogen; provided that at least one of R.sub.1 or R.sub.5 is phenyl, substituted phenyl or naphthyl; said compound being antidotally active with said thiolcarbamate herbicide compound and wherein said compound is present in an amount between about 0.0001 to about 30 parts by weight of antidote compound per each part by weight of herbicide. ### Claim 2 (depends on 1) The herbicidal composition according to claim 1 in which, R is haloalkyl, R.sub.1 is phenyl, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 3 (depends on 2) The herbicidal composition according to claim 2 in which R is monochloromethyl. ### Claim 4 (depends on 2) The herbicidal composition according to claim 2 in which R is dichloromethyl. ### Claim 5 (depends on 2) The herbicidal composition according to claim 2 in which R is trichloromethyl. ### Claim 6 (depends on 2) The herbicidal composition according to claim 2 in which R is 1,1-dichloroethyl. ### Claim 7 (depends on 2) The herbicidal composition according to claim 2 in which R is 2-bromoethyl. ### Claim 8 (depends on 2) The herbicidal composition according to claim 2 in which R is 1,2-dibromoethyl. ### Claim 9 (depends on 1) The herbicidal composition according to claim 1 in which, R is haloalkyl, R.sub.1 is chlorophenyl and R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 10 (depends on 9) The herbicidal composition according to claim 9 in which R is monochloromethyl and R.sub.1 is meta-chlorophenyl. ### Claim 11 (depends on 9) The herbicidal composition according to claim 9 in which R is dichloromethyl and R.sub.1 is meta-chlorophenyl. ### Claim 12 (depends on 9) The herbicidal composition according to claim 9 in which R is trichloromethyl and R.sub.1 is meta-chlorophenyl. ### Claim 13 (depends on 9) The herbicidal composition according to claim 9 in which R is 1,1-dichloroethyl and R.sub.1 is meta-chlorophenyl. ### Claim 14 (depends on 9) The herbicidal composition according to claim 9 in which R is 2-bromoethyl and R.sub.1 is meta-chlorophenyl. ### Claim 15 (depends on 9) The herbicidal composition according to claim 9 in which R is 1,2-dibromomethyl and R.sub.1 is meta-chlorophenyl. ### Claim 16 (depends on 9) The herbicidal composition according to claim 9 in which R is 2-chloroethyl and R.sub.1 is meta-chlorophenyl. ### Claim 17 (depends on 1) The herbicidal composition according to claim 1 in which, R is haloalkyl, R.sub.1 is chlorophenyl and R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 18 (depends on 1) The herbicidal composition according to claim 1 in which, R is haloalkyl, R.sub.1 is phenyl, R.sub.5 is phenyl and R.sub.2, R.sub.3, R.sub.4 and R.sub.6 are each hydrogen. ### Claim 19 (depends on 1) The herbicidal composition according to claim 1 in which, R is chloroalkenyl, R.sub.1 is chlorophenyl and R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 20 (depends on 1) The herbicidal composition according to claim 1 in which, R is haloalkyl, R.sub.1 is nitrophenyl and R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 21 (depends on 1) The herbicidal composition according to claim 1 in which, R is haloalkyl, R.sub.1 is phenyl, R.sub.3 is lower alkyl and R.sub.2, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 22 (depends on 1) The herbicidal composition according to claim 1 in which, R is haloalkyl, R.sub.1 is phenyl, R.sub.3 is lower alkyl, R.sub.4 is lower alkyl and R.sub.2, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 23 The method of protecting a crop from injury, said injury due to a thiolcarbamate herbicide, comprising application to the soil in which crop is to be planted and grown, a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##STR12## wherein R is haloalkyl having 1 to 6 carbon atoms, inclusive, halo is chloro or bromo or chloroalkenyl; R.sub.1 is hydrogen, lower alkyl having 1 to 4 carbon atoms, inclusive, phenyl, naphthyl, substituted phenyl wherein said substituents are mono-fluoro, mono- or di-chloro, nitro, methyl, methoxy, or hydroxyl; R.sub.2 is hydrogen or lower alkyl having 1 to 4 carbon atoms, inclusive; R.sub.3 is hydrogen, hydroxymethyl, N-methylcarbamoyloxymethyl or dichloroacetoxymethyl; R.sub.4 is hydrogen, or lower alkyl having 1 to 4 carbon atoms, inclusive; R.sub.5 is hydrogen, lower alkyl having 1 to 4 carbon atoms, inclusive or phenyl; and R.sub.6 is hydrogen; provided that at least one of R.sub.1 or R.sub.5 is phenyl, substituted phenyl or naphthyl; said compound being antidotally active with said thiolcarbamate herbicide compound and wherein said compound is present in an amount between about 0.0001 to about 30 parts by weight of antidote compound per each part by weight of herbicide. ### Claim 24 (depends on 23) The method according to claim 23 in which R is haloalkyl, R.sub.1 is chlorophenyl and R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 25 (depends on 24) The method according to claim 24 in which R is monochloromethyl and R.sub.1 is meta-chlorophenyl. ### Claim 26 (depends on 24) The method according to claim 24 in which R is dichloromethyl and R.sub.1 is meta-chlorophenyl. ### Claim 27 (depends on 24) The method according to claim 24 in which R is trichloromethyl and R.sub.1 is meta-chlorophenyl. ### Claim 28 (depends on 24) The method according to claim 24 in which R is 1,1-dichloroethyl and R.sub.1 is meta-chlorophenyl. ### Claim 29 (depends on 24) The method according to claim 24 in which R is 2-bromoethyl and R.sub.1 is meta-chlorophenyl. ### Claim 30 (depends on 24) The method according to claim 24 in which R is 1,2-dibromoethyl and R.sub.1 is meta-chlorophenyl. ### Claim 31 (depends on 24) The method according to claim 24 in which R is 2-chloroethyl and R.sub.1 is meta-chlorophenyl. ### Claim 32 (depends on 23) The method according to claim 23 in which R is haloalkyl, R.sub.1 is phenyl, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 33 (depends on 32) The method according to claim 32 in which R is monochloromethyl. ### Claim 34 (depends on 32) The method according to claim 32 in which R is dichloromethyl. ### Claim 35 (depends on 32) The method according to claim 32 in which R is trichloromethyl. ### Claim 36 (depends on 32) The method according to claim 32 in which R is 1,1-dichloroethyl. ### Claim 37 (depends on 32) The method according to claim 32 in which R is 2-bromoethyl. ### Claim 38 (depends on 32) The method according to claim 32 in which R is 1,2-dibromoethyl. ### Claim 39 (depends on 23) The method according to claim 23 in which R is haloalkyl, R.sub.1 is phenyl, R.sub.3 is lower alkyl and R.sub.2, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen. ### Claim 40 (depends on 39) The method according to claim 39 in which R is dichloromethyl, and R.sub.3 is ethyl. ### Claim 41 (depends on 39) The method according to claim 39 in which R is dichloromethyl, R.sub.3 is methyl and R.sub.4 is methyl.