# US 4,391,626 A · Haloalkylamide compounds and herbicidal antidote compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,391,626 A - Document ID: US4391626A - Status: Granted - Kind: A - Application number: 06/226,287 - Filed: 1981-01-19 - Granted: 1983-07-05 - Earliest claimed: 1980-02-09 - Assignees: Bayer Aktiengesellschaft - Inventors: Jorg Stetter; Wolf Reiser; Wilfried Faust - Web page: https://patentgrep.com/patent/US4391626A ## CPC - A01N 37/20: containing the group [IMAGE cpc-sch-A01N-0935.gif], wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof - A01N 25/32: Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions - 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 New halogenoalkylamides of the general formula ##STR1## in which R.sup.1 represents halogenoalkyl, R.sup.2 represents alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, aralkyl, halogenoalkyl or alkoximinoalkyl, R.sup.3 represents hydrogen or alkyl with 1 to 4 carbon atoms, R.sup.4 represents hydrogen or alkyl with 1 to 4 carbon atoms and R.sup.5 represents hydrogen, alkyl, alkenyl, alkynyl or aralkyl, processes for their preparation and their use as antidotes for protecting crop plants from damage by herbicidally effective thiolcarbamates and acetanilides. Novel amine derivatives of the general formula ##STR2## in which R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the above-mentioned meaning, and a process for their preparation. A novel halogenoacylamines of the general formula ##STR3## in which R.sup.1, R.sup.2 and R.sup.3 have the above-mentioned meaning and R.sup.6 represents hydrogen or methyl, as well as processes for their preparation. ## Claims ### Claim 1 Haloalkylamide compound of the formula ##STR45## wherein R.sup.1 is haloalkyl; R.sup.2 is alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, haloalkyl or alkoximinoalkyl; R.sup.3 is hydrogen or alkyl with 1 to 4 carbon atoms; R.sup.4 is hydrogen or alkyl with 1 to 4 carbon atoms; and R.sup.5 is hydrogen, alkyl, alkenyl, alkynyl or aralkyl. ### Claim 2 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.1 is haloalkyl with 1 to 4 carbon atoms and 1 to 3 halogen atoms. ### Claim 3 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.2 is alkyl with 1 to 6 carbon atoms. ### Claim 4 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.2 is alkenyl with up to 6 carbon atoms. ### Claim 5 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.2 is alkynyl with up to 6 carbon atoms. ### Claim 6 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.2 is alkoxyalkyl with from 1 to 4 carbon atoms in the alkyl moiety and 1 to 4 carbon atoms in the alkoxy moiety. ### Claim 7 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.2 is alkylthioalkyl with 1 to 4 carbon atoms in the alkyl moiety and 1 to 4 carbon atoms in the alkylthio moiety. ### Claim 8 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.2 is haloalkyl with from 1 to 6 carbon atoms and 1 to 5 halogen atoms. ### Claim 9 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.2 is alkoximinoalkyl with from 1 to 4 carbon atoms in the alkoxy group and 1 to 2 carbon atoms in the alkyl group. ### Claim 10 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.3 is hydrogen. ### Claim 11 (depends on 1) Haloalkylamido compound as claimed in claim 1 wherein R.sup.3 is methyl. ### Claim 12 (depends on 1) Haloalkylamido compound as claimed in claim 1 wherein R.sup.3 is ethyl. ### Claim 13 (depends on 1) Haloalkylamido compound as claimed in claim 1 wherein R.sup.4 is hydrogen. ### Claim 14 (depends on 1) Haloalkylamido compound as claimed in claim 1 wherein R.sup.4 is methyl. ### Claim 15 (depends on 1) Haloalkylamido compound as claimed in claim 1 wherein R.sup.4 is ethyl. ### Claim 16 (depends on 1) Haloalkylamido compound as claimed in claim 1 wherein R.sup.5 is hydrogen. ### Claim 17 (depends on 1) Haloalkylamido compound as claimed in claim 1 wherein R.sup.5 is alkyl with from 1 to 6 carbon atoms. ### Claim 18 (depends on 1) Haloalkylamido compound as claimed in claim 1 wherein R.sup.5 is alkenyl with up to 6 carbon atoms. ### Claim 19 (depends on 1) Haloalkylamido compound as claimed in claim 1 wherein R.sup.5 is alkynyl with up to 6 carbon atoms. ### Claim 20 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.5 is aralkyl with from 6 to 10 carbon atoms in the aryl moiety and from 1 to 4 carbon atoms in the alkyl moiety. ### Claim 21 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.1 is straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 3 halogen atoms; R.sup.2 is straight-chain or branched alkyl with 1 to 6 carbon atoms, alkenyl with up to 6 carbon atoms, alkynyl with up to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkyl group and 1 to 4 carbon atoms in the alkoxy part, alkylthioalkyl with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkylthio part, aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, haloalkyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, or alkoximinoalkyl with 1 to 4 carbon atoms in the alkoxy group and 1 or 2 carbon atoms in the alkyl group; R.sup.3 is hydrogen, methyl or ethyl; R.sup.4 is hydrogen, methyl or ethyl; and R.sup.5 is hydrogen, straight-chain or branched alkyl with 1 to 6 carbon atoms, alkenyl with up to 6 carbon atoms, alkynyl with up to 6 carbon atoms or aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part. ### Claim 22 (depends on 1) Haloalkylamide compound as claimed in claim 1 wherein R.sup.1 is haloalkyl with 1 to 3 carbon atoms and 1 to 3 chlorine or bromine atoms; R.sup.2 is alkyl with 1 to B 4 carbon atoms, alkenyl with up to 4 carbon atoms, alkynyl with up to 4 carbon atoms, alkoxyalkyl with 1 to 3 carbon atoms in the alkoxy group and 1 to 4 carbon atoms in the alkyl part, alkylthioalkyl with 1 to 3 carbon atoms in the alkylthio part and 1 to 3 carbon atoms in the alkyl part, aralkyl with 6 to 10 carbon atoms in the aryl part and 1 or 2 carbon atoms in the alkyl part, haloalkyl with 1 to 4 carbon atoms and 1 to 3 halogen atoms selected from fluorine, chlorine and bromine atoms, or alkoximinoalkyl with 1 to 3 carbon atoms in the alkoxy group and 1 or 2 carbon atoms in the alkyl group; R.sup.3 is hydrogen, methyl or ethyl; R.sup.4 is hydrogen, methyl or ethyl; and R.sup.5 is hydrogen, alkyl with 1 to 4 carbon atoms, alkenyl with up to 4 carbon atoms, alkynyl with up to 4 carbon atoms or aralkyl with 6 to 10 carbon atoms in the aryl part and 1 or 2 carbon atoms in the alkyl part. ### Claim 23 (depends on 1) Haloalkylamide compound as claimed in claim 1 designated N-allyl-N-(2-methoximino-ethyl)-dichloroacetamide. ### Claim 24 (depends on 1) Haloalkylamide compound as claimed in claim 1 designated N-allyl-N-(2-methoximino-propyl)-dichloroacetamide. ### Claim 25 (depends on 1) Haloalkylamide compound as claimed in claim 1 designated N-methyl-N-(2-methoximino-propyl)-dichloroacetamide. ### Claim 26 (depends on 1) Haloalkylamide compound as claimed in claim 1 designated N-allyl-N-(2-methoximino-propyl)-2-chloropropionamide. ### Claim 27 (depends on 1) An antidote composition for protecting crop plants from herbicidal damage by herbicidally active acetanilides comprising as an active ingredient an antidotal amount of at least one haloalkylamide compound as claimed in claim 1, in admixture with a solid diluent or with a liquid diluent containing a surfactant. ### Claim 28 (depends on 27) An antidote composition as claimed in claim 27 containing from 0.1 to 95% of the said compound by weight. ### Claim 29 (depends on 1) Method for the protection of crop plants from damage by herbicidally active acetanilides, which method comprises applying to the plants or their habitat an antidotally effective amount of a haloalkylamide compound as claimed in claim 1. ### Claim 30 (depends on 29) Method of claimed in claim 29 wherein said compound is applied to an area of agriculture in an amount of from 0.1 to 5 kg per hectare. ### Claim 31 (depends on 29) Method as claimed in claim 29 wherein said compound is applied to seen in an amount of 10 to 300 grams per kg of seed. ### Claim 32 (depends on 1) Herbicidal composition comprising a herbicidally active compound selected from thiolcarbamates and acetanilide herbicides and, as an antidote, an effective amount of a haloalkylamide compound as claimed in claim 1. ### Claim 33 (depends on 32) Herbicidal composition as claimed in claim 32 wherein said herbicidally active compound is a thiolcarbamate. ### Claim 34 (depends on 32) Herbicidal composition as claimed in claim 32 wherein said herbicidally active compound is an acetanilide. ### Claim 35 (depends on 32) Herbicidal composition as claimed in claim 32 containing from 0.1 to 95% of the combination of said antidote compound and said herbicide, by weight. ### Claim 36 (depends on 32) Herbicidal composition as claimed in claim 32 containing from 0.04 to 1 part by weight of said antidote compound per part by weight of said herbicidally active compound. ### Claim 37 (depends on 32) Herbicidal composition as claimed in claim 32 containing from 0.1 to 0.5 part by weight of said antidote compound per part by weight of said herbicidally active compound. ### Claim 38 (depends on 32) Method of combating weeds comprising applying to the weeds or their habitat a composition as claimed in claim 32. ### Claim 39 (depends on 38) Method as claimed in claim 38 wherein the composition is applied at a rate corresponding to 0.5 to 5 kg per hectare of said herbicidally active compound. ### Claim 40 (depends on 29) Method as claimed in claim 29 wherein said antidotal compound is selected from N-allyl-N-(2-methoximino-ethyl)-dichloroacetamide; N-allyl-N-(2-methoximino-propyl)-dichloroacetamide; N-methyl-N-(2-methoximino-propyl)-dichloroacetamide; or N-allyl-N-(2-methoximino-propyl)-2-chloroproponamide. ### Claim 41 (depends on 32) Herbicidal composition as claimed in claim 32 wherein said antidotal compound is selected from N-allyl-N-(2-methoximino-ethyl)-dichloroacetamide; N-allyl-N-(2-methoximino-propyl)-dichloroacetamide; N-methyl-N-(2-methoximino-propyl)-dichloroacetamide; or N-allyl-N-(2-methoximino-propyl)-2-chloroproponamide. ### Claim 42 (depends on 38) Method as claimed in claim 38 wherein said antidotal compound is selected from N-allyl-N-(2-methoximino-ethyl)-dichloroacetamide; N-allyl-N-(2-methoximino-propyl)-dichloroacetamide; N-methyl-N-(2-methoximino-propyl)-dichloroacetamide; or N-allyl-N-(2-methoximinopropyl)-2-chloroproponamide.