Thioether compounds as nitrification inhibitors

A method for reducing nitrification, the method comprising:

• applying a composition comprising a compound of Formula (I), or a stereoisomer, a salt, a tautomer, or N-oxide thereof, to a locus where nitrification occurs, wherein
• R1 and R2 are independently selected from the group consisting of H and C1-C2-alkyl;
• R3 is selected from the group consisting of:
• (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;
• (ii) C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C3-C8-cycloalkenyl, or C2-C8-alkynyl, wherein the C-atoms of these groups optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of 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;
• (iii) C6-C14-aryl, C5-C14-hetaryl, C6-C14-aryl-C1-C2-alkyl, or C5-C14-hetaryl-C1-C2-alkyl, wherein the aromatic moieties optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of 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 optionally carry 1, 2, 3, 4, or 5 identical or different substituents 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
• (iv) C5-C14-carbocyclyl, C5-C14-carbocyclyl-C1-C2-alkyl, C5-C14-heterocyclyl, or C5-C14-heterocyclyl-C1-C2-alkyl, wherein the heterocyclyl rings optionally carry 1, 2, 3, 4, or 5 heteroatoms selected from the group consisting of O, S, and N, of which S and/or N are optionally oxidized, and wherein the carbocyclic or heterocyclic rings optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of ═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, C1-C4-alkylen-NRcRd, C6-C10-aryl, 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 optionally carry 1, 2, 3, 4, or 5 identical or different substituents 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;
• Ra is selected from the group consisting of H, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, and C5-C10-hetaryl or C6-C10-aryl, wherein the C5-C10-hetaryl or C6-C10-aryl moieties optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of 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 optionally carry 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, CN, OH, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, and C2-C4-alkynyl;
• Rb is selected from the group consisting of H, C1-C4-alkyl, C3-C8-cycloalkyl, C2-C4-alkenyl, C2-C8-alkynyl, and C6-C10-aryl;
• Rc and Rd are independently of each other selected from the group consisting of H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C8-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 optionally carries a further heteroatom selected from the group consisting of O, S, and N as a ring member atom, of which S and/or N are optionally oxidized, and wherein the heterocyclic ring optionally carries 1, 2, 3, 4, or 5 substituents, which are independently selected from the group consisting of halogen, CN, OH, NO2, C1-C4 alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy;
• Rx is
• V, W, X, Y, and Z are independently selected from the group consisting of N, CH and CRy,
• 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;
• m is 0, 1, or 2;
• n is 0, 1, or 2;
• and
• p is 0, 1, or 2.

A method for reducing nitrification, the method comprising:

• applying a composition comprising a compound, or a stereoisomer, a salt, a tautomer, or N-oxide thereof, to a locus where nitrification occurs, wherein the compound is selected from the the group consisting of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, and A-33 as shown below:
• No.
• Compound
• A-1
• A-2
• A-3
• A-4
• A-5
• A-6
• A-7
• A-8
• A-9
• A-10
• A-11
• A-12
• A-13
• A-14
• A-15
• A-16
• A-17
• A-18
• A-19
• A-20
• A-21
• A-22
• A-23
• A-24
• A-25
• A-26
• A-27
• A-28
• A-29
• A-30
• A-31
• A-32
• A-33

An agrochemical mixture comprising (i) at least one fertilizer;

• and (ii) at least one compound, or a stereoisomer, a salt, a tautomer, or N-oxide thereof, wherein the compound is selected from the group consisting of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, and A-33 as shown below:
• No.
• Compound
• A-1
• A-2
• A-3
• A-4
• A-5
• A-6
• A-7
• A-8
• A-9
• A-10
• A-11
• A-12
• A-13
• A-14
• A-15
• A-16
• A-17
• A-18
• A-19
• A-20
• A-21
• A-22
• A-23
• A-24
• A-25
• A-26
• A-27
• A-28
• A-29
• A-30
• A-31
• A-32
• A-33

A method for treating a fertilizer, the method comprising:

• applying a compound of Formula (I), or a stereoisomer, salt, tautomer or N-oxide thereof, to the fertilizer, wherein
• R1 and R2 are independently selected from the group consisting of H and C1-C2-alkyl;
• R3 is selected from the group consisting of
• (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, and C(═N—Rx)NRcRd;
• (ii) C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C3-C8-cycloalkenyl, or C2-C8-alkynyl, wherein the C-atoms of these groups optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of 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;
• (iii) C6-C14-aryl, C5-C14-hetaryl, C6-C14-aryl-C1-C2-alkyl, or C5-C14-hetaryl-C1-C2-alkyl, wherein the aromatic moieties optionally carry 1, 2, 3, 4, or 5 identical or different substituents, selected from the group consisting of 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 that optionally carry 1, 2, 3, 4, or 5 identical or different substituents 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
• (iv) C5-C14-carbocyclyl, C5-C14-carbocyclyl-C1-C2-alkyl, C5-C14-heterocyclyl, or C5-C14-heterocyclyl-C1-C2-alkyl, wherein the heterocyclyl rings optionally carry 1, 2, 3, 4, or 5 heteroatoms selected from the group consisting of O, S, and N, of which S and/or N may optionally be oxidized, and wherein the carbocyclic or heterocyclic rings optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of ═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, 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 optionally carry 1, 2, 3, 4, or 5 identical or different substituents 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;
• Ra is selected from the group consisting of 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 optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of 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 optionally carry 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, CN, OH, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, and C2-C4-alkynyl;
• Rb is selected from the group consisting of H, C1-C4-alkyl, C3-C8-cycloalkyl, C2-C4-alkenyl, C2-C8-alkynyl, and C6-C10-aryl;
• Rc and Rd are independently of each other selected from the group consisting of H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C8-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 optionally carries a further heteroatom being selected from the group consisting of O, S, and N as a ring member atom, of which S and/or N are optionally oxidized, and wherein the heterocyclic ring optionally carries 1, 2, 3, 4, or 5 substituents, which are independently selected from the group consisting of halogen, CN, OH, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy;
• Rx is
• V, W, X, Y, and Z are independently selected from the group consisting of N, CH and
• CRy,
• 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;
• m is 0, 1, or 2;
• n is 0, 1, or 2;
• and
• p is 0, 1, or 2.

An agrochemical composition comprising:

• (i) a compound, or a stereoisomer, a salt, a tautomer, or N-oxide thereof selected from the group consisting of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, and A-33 as shown below:
• No.
• Compound
• A-1
• A-2
• A-3
• A-4
• A-5
• A-6
• A-7
• A-8
• A-9
• A-10
• A-11
• A-12
• A-13
• A-14
• A-15
• A-16
• A-17
• A-18
• A-19
• A-20
• A-21
• A-22
• A-23
• A-24
• A-25
• A-26
• A-27
• A-28
• A-29
• A-30
• A-31
• A-32
• A-33
• and
• (ii) at least one agrochemical carrier.