Herbicidal compounds

{
  "publication_number": "US5139563A",
  "country": "US",
  "kind": "A",
  "title": "Herbicidal compounds",
  "abstract": "Compounds of formula I ##STR1## wherein A is nitrogen or a group CR 5; each of R 1, R 2 and R 5 is, independently, hydrogen, halogen, formyl, cyano, carboxy, azido or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, aryloxy, alkylthio, alkenylthio, alkynylthio, arylthio, alkylcarbonyl, alkoxycarbonyl, amino, aminoxy or dialkyliminoxy; and R is ##STR2## in which R 3 is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic or aryl, or COR 8, R 8 being hydroxy, alkoxy, carboxy, alkoxycarbonyl, amino or mono- or di- alkylamino; and R 4 is a group COR 6 wherein R 6 is hydrogen, halogen, hydroxy, or optionally substituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, alkylthio, alkenylthio, alkynylthio, arylthio, aminoxy, dialkyliminoxy or amino, or R 6 is a group OR 7 in which R 7 is an optionally substituted heterocyclic ring; or ##STR3## each of R 9 and R 10 being, independently, hydrogen or alkyl; or a carboxylic acid salt of a compound with an equivalent amount of an inorganic or organic cation; have herbicidal properties. The invention also provides processes for their preparation and their use as herbicides.",
  "claims": [
    "1. A compound of the formula I ##STR30## in which A represents group CH; R 1 and R 2 each independently represents a halogen atom, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio or mono- or di-C 1-4 alkylamino; and R represents a group of the formula ##STR31## in which R 3 represents a C 1-6 alkyl group optionally substituted by C 1-4 alkylthio; cyclohexyl; benzyl; phenyl optionally substituted by one or more substituents independently selected from halogen, trifluoromethyl, C 1-4 alkyl and (C 1-4 alkoxy) carbonyl; thienyl; carboxy; (C 1-4 alkoxy)carbonyl; (C 1-4 alkoxy)carbonylcarbonyl or de(C 1-4 alkyl)carbamoyl; and R 4 represents a group COR 6 wherein R 6 represents hydroxy; C 1-4 alkoxy optionally substituted by halogen or C 1-4 alkoxy, C 1-4 alkylthio, phenyl, optionally substituted on the phenyl ring by one or more substituents independently selected from halogen and C 1-4 alkoxy, furyl, tetrahydrofuryl or thienyl; C 1-4 alkylthio; C 2-4 alkynyloxy; phenoxy optionally substituted by one or more substituents independently selected from C 1-4 alkyl, nitro, hydroxy (C 1-4) alkyl, and a group of the formula ##STR32## phenylthio; amino optionally substituted by amino, di(C 1-4) alkylamino or phenyl optionally substituted by carboxy or (C 1-4 alkoxy)carbonyl; or di(C 1-4) alkylaminoxy; or R represents a group of the formula ##STR33## in which R 4 is as defined above and wherein one of R 9 and R 10 represents hydrogen and the other represents C 1-4 alkyl, or a carboxylic acid salt of a compound of formula I with an equivalent amount of an inorganic or organic cation.",
    "2. A compound as claimed in claim 1, in which R 1 and R 2 each independently represent chlorine, methyl, methoxy, methylthio, methylamino or dimethylamino.",
    "3. A compound as claimed in claim 1, in which R 3 represents C 2-6 alkyl, benzyl or an unsubstituted phenyl.",
    "4. A compound as claimed in claim 3, in which R 3 represents isopropyl, n-propyl, i-butyl, n-butyl, s-butyl, t-butyl, benzyl or phenyl.",
    "5. A compound as claimed in claim 1, in which R 4 represents COR 6 wherein R 6 represents hydroxy, C 1-4 alkoxy or optionally substituted amino.",
    "6. A compound as claimed in claim 5, in which R 4 represents the group COR 6 in which R 6 represents hydroxy or C 1-4 alkoxy.",
    "7. A carboxylic acid salt as claimed in claim 1, which is an alkali metal salt.",
    "8. A compound as claimed in claim 1, wherein R 1 and R 2 are the same and each represents methyl or methoxy, and R represents a group of the formula (A) in which R 3 represents n-butyl, i-butyl, t-butyl or phenyl and R 4 represents carboxy or methoxycarbonyl.",
    "9. A compound as claimed in claim 8, wherein R 1 is CH 3, R 2 is CH 3, R 3 is i-C 4 H 9 and R 4 is COOH, or R 1 is OCH 3, R 2 is OCH 3, R 3 is i-C 4 H 9 and R 4 is CO 2 CH 3, or R 1 is CH 3, R 2 is CH 3, R 3 is phenyl and R 4 is CO 2 CH 3.",
    "10. A herbicidal composition which comprises an effective amount of the compound as claimed in claim 1 in association with a carrier.",
    "11. A method of combating undesired plant growth at a locus which comprises treating the locus with an effective amount of a compound as claimed in claim 1.",
    "12. A method of combating undesired plant growth at a locus which comprises treating the locus with an effective amount of a composition as claimed in claim 10."
  ],
  "cpc": [
    "C07D 239/52",
    "A01N 43/54",
    "A01N 43/66",
    "C07D 239/34",
    "C07D 239/60",
    "C07D 251/16",
    "C07D 251/20",
    "C07D 251/26",
    "C07D 251/30",
    "C07D 251/46",
    "C07D 405/12",
    "C07D 409/12"
  ],
  "assignees": [
    "SHELL RES LTD"
  ],
  "filing_date": "1990-05-30",
  "publication_date": "1992-08-18",
  "grant_date": "1992-08-18",
  "priority_date": "1989-06-02",
  "application_number": "US-52936890-A",
  "family_id": "10657773",
  "citations": [
    "DD109170A1",
    "EP0030138A1",
    "EP0347811A1",
    "GB1132306A",
    "GB814947A",
    "US3920648A",
    "US4871387A",
    "US4889552A"
  ]
}