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US 12,122,728 B2Granted
Use of substituted 2-thiazolines as nitrification inhibitors
AssigneeBASF SE
InventorsPeter Nesvadba, Allan F. Cunningham, Shrirang Hindalekar, Barbara Nave, Tejas Pothi, Alexander Wissemeier
Life of this patent
Estimating the term…
Abstract
The invention relates to novel nitrification inhibitors of formula I, which are substituted 2-thiazoline 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.
Claims16
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 H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C4-alkylsulfonyl, benzyl, hetaryl, 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, or ═CRC1RC2, wherein RC1 and RC2 together form a 5- or 6-membered saturated, partially or fully unsaturated, or aromatic carbocyclic or heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms selected from O, N or S, wherein said N- and/or S-atoms are independently oxidized or non-oxidized, and wherein each substitutable carbon or heteroatom in the aforementioned cyclic moieties is independently unsubstituted or substituted with one or more, same or different substituents Rx;
- and wherein
- RS is H, C1-C2-alkyl, C3-C6-cycloalkyl, 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-C6-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 selected from 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, or C1-C6-haloalkoxy;
- and
- Q+is selected from the group consisting of Na+, K+, Ca2+, and NH4+.
15 more elements
A substituted 2-thiazoline compound of formula I
- wherein the compound of formula I is selected from the group consisting of
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 H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C4-alkylsulfonyl, benzyl, hetaryl, 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, or ═CRC1RC2, wherein RC1 and RC2 together form a 5- or 6-membered saturated, partially or fully unsaturated, or aromatic carbocyclic or heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms selected from O, N or S, wherein said N- and/or S-atoms are independently oxidized or non-oxidized, and wherein each substitutable carbon or heteroatom in the aforementioned cyclic moieties is independently unsubstituted or substituted with one or more, same or different substituents Rx;
- and wherein
- RS is H, C1-C2-alkyl, C3-C6-cycloalkyl, 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-C6-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 selected from 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, or C1-C6-haloalkoxy;
- and
- Q+is selected from the group consisting of Na+, K+, Ca2+, and NH4+.
14 more elements
A method for treating a fertilizer or a composition, comprising applying a nitrification inhibitor
- 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 H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C4-alkylsulfonyl, benzyl, hetaryl, 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, or ═CRC1RC2, wherein RC1 and RC2 together form a 5- or 6-membered saturated, partially or fully unsaturated, or aromatic carbocyclic or heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms selected from O, N or S, wherein said N- and/or S-atoms are independently oxidized or non-oxidized, and wherein each substitutable carbon or heteroatom in the aforementioned cyclic moieties is independently unsubstituted or substituted with one or more, same or different substituents Rx;
- and wherein
- RS is H, C1-C2-alkyl, C3-C6-cycloalkyl, 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-C6-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 selected from 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, or C1-C6-haloalkoxy;
- and
- Q+ is selected from the group consisting of Na+, K+, Ca2+, and NH4+ to the fertilizer or the composition.
13 more elements
Dependencies are inferred from the claim text.