Triazolinethione-phosphoric acid derivatives

• US 6,586,415 B2
• Filed: 11/15/2001
• Issued: 07/01/2003
• Est. Priority Date: 07/25/1997
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Stenzel, Klaus, Dutzmann, Stefan, Krüger, Bernd-Wieland, Hillebrand, Stefan, Mauler-Machnik, Astrid, Jautelat, Manfred
• Primary Examiner(s): Morris, Patricia L.
• Application Number:
  US10/003,374
• Publication Number:
  US 20030040628A1
• Time in Patent Office: 593 Days
• Field of Search: 514/93, 514/184, 548/101, 548/111
• US Class Current: 514/93
• CPC Class Codes: A01N 57/32 containing heterocyclic radicals
• CPC Class Codes: C07F 9/6518 Five-membered rings

Abstract

Novel triazolinethilone-phosphoric acid derivatives of the formula

in which

R¹, R², R³ and Q are each as defined in the description

and their metal salt complexes,

a process for preparing the novel substances and their use as microbicides in crop protection and in the protection of materials are described.

Claims

1. A triazolinethione-phosphoric acid derivative of the formula

wherein

R¹ represents a moiety selected from the group consisting of straight-chain or branched alkyl having 1 to 6 carbon atoms;

cycloalkyl having 3 to 6 carbon atoms;

straight-chain or branched alkoxy having 1 to 6 carbon atoms;

alkoxyalkoxy having 1 to 4 carbon atoms in each alkoxy moiety;

alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety;

phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano;

phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety, wherein the phenyl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano;

phenoxy which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano;

phenylalkoxy having 1 or 2 carbon atoms in the alkoxy moiety, wherein the phenyl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano; and

a radical of the formula

wherein

R⁴ represents hydrogen or alkyl having 1 to 4 carbon atoms and

R⁵ is a moiety selected from the group consisting of alkyl having 1 to 6 carbon atoms;

phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety, wherein the phenyl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano; and

phenyl which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano;

R² represents a moiety selected from the group consisting of straight-chain or branched alkoxy having 1 to 6 carbon atoms, cycloalkoxy having 3 to 6 carbon atoms, alkoxyalkoxy having 1 to 4 carbon atoms in each alkoxy moiety;

phenoxy which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano; and

phenylalkoxy having 1 or 2 carbon atoms in the alkoxy moiety, wherein the phenyl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano.

and

R³ represents a radical of the formula

 

in which

R²³ represents straight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms having 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms and halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogen atoms or represents phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to4 carbon atoms and halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogen atoms,

X⁹ represents fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, and methyl or represents phenoxy which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl, and

z represents the numbers 0, 1, 2 or 3, where X⁹ represents identical or different radicals if z represents 2 or 3, and

Q represents sulphur.

2. A triazolinethione-phosphoric acid derivative according to claim 1, wherein

R¹ represents a moiety selected from the group consisting of straight-chain or branched alkyl having 1 to 6 carbon atoms; cycloalkyl having 3 to 6 carbon atoms;

straight-chain or branched alkoxy having 1 to 6 carbon atoms;

alkoxyalkoxy having 1 to 4 carbon atoms in each alkoxy moiety;

alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety.

3. A triazolinethione-phosphoric acid derivative according to claim 1, wherein

R¹ represents a moiety selected from the group consisting of phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano.

4. A triazolinethione-phosphoric acid derivative according to claim 1, wherein

R¹ represents a moiety selected from the group consisting of phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety, wherein the phenyl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano;

phenoxy which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano;

phenylalkoxy having 1 or 2 carbon atoms in the alkoxy moiety, wherein the phenyl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano; and

a radical of the formula

5. A triazolinethione-phosphoric acid derivative according to claim 1, wherein

R² represents a moiety selected from the group consisting of straight-chain or branched alkoxy having 1 to 6 carbon atoms, cycloalkoxy having 3 to 6 carbon atoms, alkoxyalkoxy having 1 to 4 carbon atoms in each alkoxy moiety.

6. A triazolinethione-phosphoric acid derivative according to claim 1, wherein

R² represents a moiety selected from the group consisting of phenoxy which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano;

and

phenylalkoxy having 1 or 2 carbon atoms in the alkoxy moiety, wherein the phenyl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano.

7. A microbicidal composition comprising a microbiocidally effective amount of a triazolinethione-phosphoric acid derivative of the formula (I) of claim 1 in admixture with an inert diluent.

8. A method for controlling undesirable microorganisms in crop protection and in the protection of materials comprising applying a microbiocidally effective amount of a triazolinethione-phosphoric acid derivative of the formula (I) of claim 1 to the microorganisms and/or their habitat.