Substituted 5-alkoxy-1,2,4-triazol-3-(THI) ones

• US 5,652,372 A
• Filed: 04/25/1996
• Issued: 07/29/1997
• Est. Priority Date: 05/09/1988
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Kluth, Joachim, Muller, Klaus-Helmut, Lurssen, Klaus, Santel, Hans-Joachim, Konig, Klaus, Schmidt, Robert R.
• Primary Examiner(s): Morris, Patricia L.
• Application Number:
  US08/637,995
• Time in Patent Office: 460 Days
• Field of Search: 548/263.4
• US Class Current: 548/263.4
• CPC Class Codes: A01N 47/38 containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
• CPC Class Codes: A01N 51/00 Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
• CPC Class Codes: C07D 249/12 Oxygen or sulfur atoms
• CPC Class Codes: C07D 249/14 Nitrogen atoms
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems

Abstract

Herbicidal 5-alkoxy-1,2,4-triazol-3-(thi)ones of the gerneral formula ##STR1## (in which the radicals R¹, R², R³, X and Y have the meanings given in the description),

processes for their preparation, and their use as herbicides, and also new intermediates of the formula (II) ##STR2##

Claims

1. A 5-alkoxy-1,2,4-triazol-3-(thi)one derivative of the formula ##STR677## in which R² represents in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl having 2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, alkoxyalkyl or alkoxy, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, cyanoalkyl having 1 to 8 carbon atoms, or represents cycloalkylalkyl or cycloalkyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety,

R³ represents in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, halogenoalkinyl having 2 to 8 carbon atoms, and 1 to 13 identical or different halogen atoms, alkoxyalkyl having 1 to 6 carbon atoms in each of the individual alkyl moieties, or represents cyanoalkyl having 1 to 8 carbon atoms, and

R⁴ is methyl, ethyl, phenyl or benzyl.

2. A 5-alkoxy-1,2,4-triazol-3-(thi)one derivative according to claim 1 in which

R² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, or represents allyl, propargyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl or ethoxyethyl, or represents straight-chain or branched halogenoalkyl, halogenoalkenyl and halogenoalkinyl halogenoalkenyl and halogenoalkinyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or represents cyclopentyl, cyclohexyl, cyclopropyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl or cyclohexylethyl,

R³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, n- or i-hexyl, or represents allyl, propargyl, methoxyethyl, ethoxyethyl, fluoroethyl, chloroethyl, fluoropropyl, chloropropyl or cyanoethyl,

R⁴ represents methyl, ethyl, phenyl or benzyl.

3. A 5-alkoxy-1,2,4-triazol-3-one derivative according to claim 1, which has the formula

R² represents methyl, ethyl, n-, i- or cyclopropyl, n-, i-, s- or t-butyl,

R³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl,

R⁴ represents methyl, ethyl, phenyl or benzyl.

4. A 5-alkoxy-1,2,4-triazol-3-one derivative according to claim 1, which has the formula ##STR678##