# US 4,400,508 A · Orotic acid derivatives > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,400,508 A - Document ID: US4400508A - Status: Granted - Kind: A - Application number: 06/319,793 - Filed: 1981-11-09 - Granted: 1983-08-23 - Earliest claimed: 1980-11-18 - Assignees: Ube Industries, Ltd. - Inventors: Kiyoshi Fukui; Noboru Kakeya; Hiroshi Jibiki; Fumio Matsuo - Web page: https://patentgrep.com/patent/US4400508A ## CPC - C07D 239/557: with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid - A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines - C07D 233/96: having three double bonds between ring members or between ring members and non-ring members - 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 Novel orotic acid derivatives useful as agricultural chemicals or intermediates thereof are disclosed. The orotic acid derivatives are represented by the formula ##STR1## where Me is an alkali metal, R.sup.1 is an alkyl group of from 1 to 4 carbon atoms, an allyl group, a cyclohexyl group, a benzyl group, or a group ##STR2## (where R.sup.2 is an alkyl group of from 1 to 4 carbon atoms, an alkoxyl group of from 1 to 4 carbon atoms or a halogen atom and n is 0, 1, 2 or 3), m is an integer of 1 or 2, and X is a chlorine, bromine or iodine atom or a group --COR.sup.0 (where R.sup.0 is an alkyl group of from 1 to 4 carbon atoms or a phenyl group) when m is 1, and a group --COO.sup.- when m is 2. ## Claims ### Claim 1 An orotic acid derivative represented by the general formula ##STR67## where Me is an alkali metal, R.sup.1 is an alkyl group of from 1 to 4 carbon atoms, an allyl group, a cyclohexyl group, a benzyl group, or a group ##STR68## (where R.sup.2 is an alkyl group of from 1 to 4 carbon atoms, an alkoxyl group of from 1 to 4 carbon atoms or a halogen atom and n is an integer of 0, 1, 2 or 3), m is an integer of 1 or 2, and X is a chlorine atom, a bromine atom, an iodine atom or --COR.sup.0 (where R.sup.0 is an alkyl group of from 1 to 4 carbon atoms or a phenyl group) when m is 1, and a group --COO.sup.- when m is 2. ### Claim 2 (depends on 1) The orotic acid derivative as claimed in claim 1, which is represented by the formula ##STR69## where Me and R.sup.1 are as defined in claim 1. ### Claim 3 (depends on 1) The orotic acid derivative as claimed in claim 1, which is represented by the formula ##STR70## where R.sup.1 and X are as defined in claim 1. ### Claim 4 (depends on 2) The orotic acid derivative as claimed in claim 2, which is selected from the group consisting of potassium 5-carboxy-1-isopropylorotate, sodium 5-carboxy-1-(n-butyl)orotate, lithium 5-carboxy-1-(n-butyl) orotate, potassium 5-carboxy-1-allylorotate, potassium 5-carboxy-1-cyclohexylorotate, sodium 5-carboxy-1-cyclohexylorotate, potassium 5-carboxy-1-phenylorotate, lithium 5-carboxy-1-phenylorotate, potassium 5-carboxy-1-(p-tolyl)orotate, sodium 5-carboxy-1-(p-tolyl)orotate, potassium 5-carboxy-1-(2,5-dichlorophenyl)orotate, sodium 5-carboxy-1-(3,5-dicholorophenyl)orotate, lithium 5-carboxy-1-(3,5-dichlorophenyl)orotate, potassium 5-carboxy-1-(2,4,5-trichlorophenyl)orotate, and sodium 5-carboxy-1-(p-methoxyphenyl)orotate. ### Claim 5 (depends on 2) The orotic acid derivative as claimed in claim 2, which is potassium 5-carboxy-1-(n-butyl)orotate. ### Claim 6 (depends on 2) The orotic acid derivative as claimed in claim 2, which is potassium 5-carboxy-1-benzylorotate. ### Claim 7 (depends on 2) The orotic acid derivative as claimed in claim 2, which is sodium 5-carboxy-1-phenylorotate. ### Claim 8 (depends on 2) The orotic acid derivative as claimed in claim 2, which is lithium 5-carboxy-1-(p-tolyl)orotate. ### Claim 9 (depends on 2) The orotic acid derivative as claimed in claim 2, which is sodium 5-carboxy-1-(p-chlorophenyl)orotate. ### Claim 10 (depends on 2) The orotic acid derivative as claimed in claim 2, which is potassium 5-carboxy-1-isopropylorotate. ### Claim 11 (depends on 2) The orotic acid derivative as claimed in claim 2, which is potassium 5-carboxy-1-(2,4,5-trichlorophenyl)orotate. ### Claim 12 (depends on 3) The orotic acid derivative as claimed in claim 3, which is selected from the group consisting of 5-chloro-1-isopropylorotic acid, 5-chloro-1-phenylorotic acid, 1-(p-methoxyphenyl)-5-chloroorotic acid, 5-chloro-1-(p-chlorophenyl)orotic acid, 5-bromo-1-isopropylorotic acid, 5-bromo-1-(n-butyl)orotic acid, 1-benzyl-5-bromoorotic acid, 5-bromo-1-phenylorotic acid, 5-bromo-1-(p-tolyl)orotic acid, 1-(p-methoxyphenyl)-5-bromoorotic acid, 5-bromo-1-(p-chlorophenyl)orotic acid, 5-bromo-1-(3,5-dichlorophenyl)orotic acid, 5-iodo-1-isopropylorotic acid, 1-cyclohexyl-5-iodoorotic acid, 1-allyl-5-iodoorotic acid, 5-iodo-1-phenylorotic acid, 1-(p-methoxyphenyl)-5-iodoorotic acid, 1-(p-chlorophenyl)-5-iodoorotic acid, 5-benzoyl-1-isopropylorotic acid, 5-benzoyl-1-n-butylorotic acid, 5-benzoyl-1-benzylorotic acid, 5-benzoyl-1-(p-tolyl)orotic acid, 5-benzoyl-1-(3,4-xylyl)orotic acid, 5-benzoyl-1-(3,5-dichlorophenyl)orotic acid, 5-benzoyl-1-(2,4,5-trichlorophenyl)orotic acid, 5-benzoyl-1-(p-methoxyphenyl)orotic acid, 5-acetyl-1-ethylorotic acid, 5-acetyl-1-(n-butyl)orotic acid, 5-acetyl-1-phenylorotic acid, 5-acetyl-1-cyclohexylorotic acid, 5-acetyl-1-(p-tolyl)orotic acid, 5-acetyl-1-(p-chlorophenyl)orotic acid, 5-acetyl-1-(3,5-dichlorophenyl)orotic acid and 5-acetyl-1-(p-methoxyphenyl)orotic acid. ### Claim 13 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-chloro-1-isopropylorotic acid. ### Claim 14 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-chloro-1-phenylorotic acid. ### Claim 15 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 1-(p-methoxyphenyl)-5-chloroorotic acid. ### Claim 16 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-bromo-1-(p-tolyl)orotic acid. ### Claim 17 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 1-(p-methoxyphenyl)-5-bromoorotic acid. ### Claim 18 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-bromo-1-(3,5-dichlorophenyl)orotic acid. ### Claim 19 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-iodo-1-isopropylorotic acid. ### Claim 20 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 1-(p-methoxyphenyl)-5-iodoorotic acid. ### Claim 21 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 1-(p-chlorophenyl)-5-iodoorotic acid. ### Claim 22 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-benzoyl-1-methylorotic acid. ### Claim 23 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-benzoyl-1-phenylorotic acid. ### Claim 24 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-acetyl-1-(3,5-dichlorophenyl)orotic acid. ### Claim 25 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-benzoyl-1-allylorotic acid. ### Claim 26 (depends on 3) The orotic acid derivative as claimed in claim 3, which is 5-benzoyl-1-cyclohexylorotic acid.