Thioether compounds as nitrification inhibitors

A thioether compound of formula I

• or a stereoisomer, salt, tautomer or N-oxide thereof as nitrification inhibitor,
• wherein
• R1 and R2 are independently selected from H and C1-C2-alkyl;
• and wherein
• R3 is
• (i) C(═O)Ra, C(═O)ORa, C(═O)NRcRd, C(═N—OH)Ra, C(═N—OH)NRcRd, C(═N—Rb)Ra, C(═N—Rb)NRcRd, C(═N—Rx)Ra, or C(═N—Rx)NRcRd;
• or
• (ii) C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C3-C8-cycloalkenyl, or C2-C8-alkynyl, wherein the C-atoms of these groups may in each case be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from halogen, CN, ORa, NO2, NRcRd, NRb(C═O)Ra, C(═O)Ra, C(═O)ORa, C(═O)NRcRd, S(O)nRa, and S(O)nNRcRd;
• or
• (iii) C6-C14-aryl, C5-C14-hetaryl, C6-C14-aryl-C1-C2-alkyl, or C5-C14-hetaryl-C1-C2-alkyl, wherein the aromatic moieties may in each case be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from halogen, CN, Rx, ORa, SRa, NRcRd NRb(C═O)Ra, NRb(C═O)NRcRd, C(═O)Ra, C(═O)ORa, C(═O)NRcRd, S(O)nRa, S(O)nNRcRd, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylen-ORa, C1-C4-alkylen-NRcRd, C6-C10-aryl, C6-C10-aryl-C1-C2-alkyl, C5-C10-hetaryl, C5-C10-hetaryl-C1-C2-alkyl, C5-C10-carbocyclyl, C5-C10-carbocyclyl-C1-C2-alkyl, C5-C10-heterocyclyl, and C5-C10-heterocyclyl-C1-C2-alkyl, wherein the C6-C10-aryl, C5-C10-hetaryl, C5-C10-carbocyclyl, and C5-C10-heterocyclyl moieties may in each case be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from halogen, CN, NO2, OH, SH, NH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-dialkylamino, and C1-C4-haloalkyl;
• or
• (iv) C5-C14-carbocyclyl, C5-C14-carbocyclyl-C1-C2-alkyl, C5-C14-heterocyclyl, or C5-C14-heterocyclyl-C1-C2-alkyl, wherein the heterocyclyl rings may carry 1, 2, 3, 4, or 5 heteroatoms being selected from O, S, and N, of which S and/or N may optionally be oxidized, and wherein the carbocyclic or heterocyclic rings may in each case be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from ═O, ═S, halogen, CN, Rx, ORa, SRa, NO2, NRcRd, NRb(C═O)Ra, NRb(C═O)NRcRd, C(═O)Ra, C(═O)ORa, C(═O)NRcRd, S(O)nRa, S(O)nNRcRd, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylen-ORa, C1i-C4-alkylen-NRcRd, C6-C10-aryl, C6-C10-aryl-C1-C2-alkyl, C5-C10-hetaryl, C5-C10-hetaryl-C1-C2-alkyl, C5-C10-carbocyclyl, C5-C10-carbocyclyl-C1-C2-alkyl, C5-C10-heterocyclyl, and C5-C00-heterocyclyl-C1-C2-alkyl, wherein the C6-C10-aryl, C5-C10-hetaryl, C5-C10-carbocyclyl, and C5-C10-heterocyclyl moieties may in each case be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from halogen, CN, NO2, OH, SH, NH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-dialkylamino, and C1-C4-haloalkyl;
• or
• and wherein
• Ra is H, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-alkynyl;
• C5-C10-hetaryl or C6-C10-aryl, wherein the C5-C10-hetaryl or C6-C10-aryl moieties may in each case be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from halogen, CN, OH, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C5-C6-hetaryl and C6-aryl, wherein said C5-C6-hetaryl and C6-aryl moieties may be unsubstituted or may carry 1, 2, 3, 4, or 5 substituents selected from halogen, CN, OH, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, and C2-C4-alkynyl;
• Rb is H, C1-C4-alkyl, C3-C8-cycloalkyl, C2-C4-alkenyl, C2-C8-alkynyl, or C6-C10-aryl;
• and
• Rc and Rd are independently of each other selected from the group consisting of H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C5-cycloalkyl, C6-C10-aryl, and C5-C10-hetaryl;
• or
• Rc and Rd together with the N-atom to which they are bonded form a 5- to 6-membered, saturated or unsaturated heterocycle, which may carry a further heteroatom being selected from O, S, and N as a ring member atom, of which S and/or N may optionally be oxidized, and wherein the heterocyclic ring may be unsubstituted or may carry 1, 2, 3, 4, or 5 substituents, which are independently selected from halogen, CN, OH, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy;
• and wherein
• Rx is
• wherein § marks the connection to the atom to which Rx is bonded;
• and
• wherein V, W, X, Y, and Z are independently selected from N, CH and CRy,
• wherein RY is selected from the group consisting of halogen, CN, NO2, OH, SH, NH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-dialkylamino, and C1-C4-haloalkyl;
• and wherein
• m is 0, 1, or 2;
• n is 0, 1, or 2;
• and
• p is 0, 1, or 2.