Use of a substituted thiazolidine compound as nitrification inhibitor
AssigneeBASF SE
InventorsPeter Nesvadba, Allan F. Cunningham, Olof Wallquist, Barbara Nave, Alexander Wissemeier
Life of this patent
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Abstract
The invention relates to novel nitrification inhibitors of formula I, which are substituted thiazolidine compounds. Moreover, the invention relates to the use of compounds of formula (I) as nitrification inhibitors, i.e. for reducing nitrification, as well as agrochemical mixtures and compositions comprising the nitrification inhibitors of formula (I).
Claims15
A method for reducing nitrification, comprising treating a plant growing on soil or soil substituents and/or the locus or soil or soil substituents where the plant is growing or is intended to grow with at least one compound of formula I
- or a salt, stereoisomer, tautomer, N-oxide, or S-oxide thereof for use as a nitrification inhibitor,
- wherein
- R1, R2, R3 and R4 are independently of each other selected from the group consisting of H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C4-alkylsulfonyl, benzyl, and phenyl, wherein said groups are unsubstituted or substituted by one or more, same or different substituents Rx;
- or
- R1 and R2 or R3 and R4 together form ═O;
- and wherein
- RN is H, C1-C6-alkyl, C3-C6-cycloalkyl, benzyl, allyl, propargyl, or phenyl, wherein said groups are unsubstituted or substituted by one or more, same or different substituents Ry;
- CHRaC(═O)ORb, CHRaC(═O)O−-Q+, CHRaC(═O)Rd, CHRaC(═O)NRbRc, C(═O)Rd, C(═O)ORb, C(═O)NRbRc, CHRaORb, C(═O)(CH2)2C(═O)ORb, or CSNRbRc;
- Ra is H, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C3-C6-cycloalkyl, phenyl, or phenyl-C1-C2-alkyl;
- Rb is H, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, aryl, phenyl, or phenyl-C1-C2-alkyl;
- Rc is H, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, aryl, phenyl, or phenyl-C1-C2-alkyl;
- Rd is H, C1-C3-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, phenyl-C1-C2-alkyl, hetaryl, or hetaryl-C2-C3-alkenyl, wherein these groups are unsubstituted or substituted by one or more, same or different substituents are selected from the group consisting of halogen, OH, OCH3, and CH3;
- Rx is halogen, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylcarbonyl, or C1-C6-alkylcarboxy;
- Ry is halogen, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, or phenyl;
- and
- Q+ is selected from the group consisting of Na+, K+, Ca2+, and NH4+.
A method for treating a fertilizer, comprising applying a nitrification inhibitor of formula I
- or a salt, stereoisomer, tautomer, N-oxide, or S-oxide thereof for use as a nitrification inhibitor,
- wherein
- R1, R2, R3 and R4 are independently of each other selected from the group consisting of H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C4-alkylsulfonyl, benzyl, and phenyl, wherein said groups are unsubstituted or substituted by one or more, same or different substituents Rx;
- or
- R1 and R2 or R3 and R4 together form ═O;
- and wherein
- RN is H, C1-C6-alkyl, C3-C6-cycloalkyl, benzyl, allyl, propargyl, or phenyl, wherein said groups are unsubstituted or substituted by one or more, same or different substituents Ry;
- CHRaC(═O)ORb, CHRaC(═O)O−-Q+, CHRaC(═O)Rd, CHRaC(═O)NRbRc, C(═O)Rd, C(═O)ORb, C(═O)NRbRc, CHRaORb, C(═O)(CH2)2C(═O)ORb, or CSNRbRc;
- Ra is H, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C3-C6-cycloalkyl, phenyl, or phenyl-C1-C2-alkyl;
- Rb is H, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, aryl, phenyl, or phenyl-C1-C2-alkyl;
- Rc is H, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, aryl, phenyl, or phenyl-C1-C2-alkyl;
- Rd is H, C1-C3-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, phenyl-C1-C2-alkyl, hetaryl, or hetaryl-C2-C3-alkenyl, wherein these groups are unsubstituted or substituted by one or more, same or different substituents are selected from the group consisting of halogen, OH, OCH3, and CH3;
- Rx is halogen, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylcarbonyl, or C1-C6-alkylcarboxy;
- Ry is halogen, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, or phenyl;
- and
- Q+ is selected from the group consisting of Na+, K+, Ca2+, and NH4+ to the fertilizer.
An agrochemical mixture comprising (i) at least one fertilizer;
- and (ii) at least one compound of formula I
- or a salt, stereoisomer, tautomer, N-oxide, or S-oxide thereof for use as a nitrification inhibitor,
- wherein
- R1, R2, R3 and R4 are independently of each other selected from the group consisting of H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C4-alkylsulfonyl, benzyl, and phenyl, wherein said groups are unsubstituted or substituted by one or more, same or different substituents Rx;
- or
- R1 and R2 or R3 and R4 together form ═O;
- and wherein
- RN is H, C1-C6-alkyl, C3-C6-cycloalkyl, benzyl, allyl, propargyl, or phenyl, wherein said groups are unsubstituted or substituted by one or more, same or different substituents Ry;
- CHRaC(═O)ORb, CHRaC(═O)O−-Q+, CHRaC(═O)Rd, CHRaC(═O)NRbRc, C(═O)Rd, C(═O)ORb, C(═O)NRbRc, CHRaORb, C(═O)(CH2)2C(═O)ORb, or CSNRbRc;
- Ra is H, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C3-C6-cycloalkyl, phenyl, or phenyl-C1-C2-alkyl;
- Rb is H, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, aryl, phenyl, or phenyl-C1-C2-alkyl;
- Rc is H, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, aryl, phenyl, or phenyl-C1-C2-alkyl;
- Rd is H, C1-C3-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, phenyl-C1-C2-alkyl, hetaryl, or hetaryl-C2-C3-alkenyl, wherein these groups are unsubstituted or substituted by one or more, same or different substituents are selected from the group consisting of halogen, OH, OCH3, and CH3;
- Rx is halogen, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylcarbonyl, or C1-C6-alkylcarboxy;
- Ry is halogen, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, or phenyl;
- and
- Q+ is selected from the group consisting of Na+, K+, Ca2+, and NH4+.
Dependencies are inferred from the claim text.