Thioether compounds as nitrification inhibitors

Patent metadata

Field	Value
Publication number	US-11053175-B2
Application number	US-201615573224-A
Country	US
Kind code	B2
Filing date	May 11, 2016
Priority date	May 12, 2015
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

Abstract

Provided herein are a use of thioether compounds of formula I as nitrification inhibitors, and agricultural mixtures and compositions including the thioether compounds.

First claim

The invention claimed is:

1. At least one thioether compound of formula I 1 ,

or a stereoisomer thereof, a salt thereof, a tautomer thereof, or an N-oxide thereof as nitrification inhibitor,
wherein
R 1 and R 2 are independently selected from the group consisting of H and C 1 -C 2 -alkyl;
and wherein
R 3 is selected from the group consisting of (i) C(═N—OH)R a and C(═N—R x )NR c R d ;
wherein
R a is selected from the group consisting of H and C 1 -C 2 -alkyl;
R c and R d are independently selected from the group consisting of H and C 1 -C 2 -alkyl; and
R x is

wherein § marks the connection to the atom to which R x is bonded; and
wherein V, W, Y, and Z each represent CH, and X is selected from the group consisting of CH and CR y ,
wherein R Y is selected from the group consisting of halogen, CN, C 1 -C 2 -alkyl, and C 1 -C 2 -alkoxy;
and wherein
m is one of 0, 1, and 2;
p is one of 1 and 2.

2. 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

R 1 and R 2 are independently selected from the group consisting of H and C 1 -C 2 -alkyl;
R 3 is selected from the group consisting of:
(i) C(═O)R a , C(═O)OR a , C(═O)NR c R d , C(═N—OH)R a , C(═N—OH)NR c R d , C(═N—R b )R a , C(═N—R b )NR c R d , C(═N—R x )R a , or C(═N—R x )NR c R d ;
(ii) C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, C 3 -C 8 -cycloalkenyl, or C 2 -C 8 -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, OR a , NO 2 , NR c R d , NR b (C═O)R a , C(═O)R a , C(═O)OR a , C(═O)NR c R d , S(O) n R a , and S(O) n NR c R d ;
(iii) C 6 -C 14 -aryl, C 5 -C 14 -hetaryl, C 6 -C 14 -aryl-C 1 -C 2 -alkyl, or C 5 -C 14 -hetaryl-C 1 -C 2 -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, R x , OR a , SR a , NR c R d , NR b (C═O)R a , NR b (C═O)NR c R d , C(═O)R a , C(═O)OR a , C(═O)NR c R d , S(O) n R a , S(O) n NR c R d , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkylen-OR a , C 1 -C 4 -alkylen-NR c R d , C 6 -C 10 -aryl, C 6 -C 10 -aryl-C 1 -C 2 -alkyl, C 5 -C 10 -hetaryl, C 5 -C 10 -hetaryl-C 1 -C 2 -alkyl, C 5 -C 10 -carbocyclyl, C 5 -C 10 -carbocyclyl-C 1 -C 2 -alkyl, C 5 -C 10 -heterocyclyl, and C 5 -C 10 -heterocyclyl-C 1 -C 2 -alkyl, wherein the C 6 -C 10 -aryl, C 5 -C 10 -hetaryl, C 5 -C 10 -carbocyclyl, and C 5 -C 10 -heterocyclyl moieties optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of halogen, CN, NO 2 , OH, SH, NH 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -dialkylamino, and C 1 -C 4 -haloalkyl; and
(iv) C 5 -C 14 -carbocyclyl, C 5 -C 14 -carbocyclyl-C 1 -C 2 -alkyl, C 5 -C 14 -heterocyclyl, or C 5 -C 14 -heterocyclyl-C 1 -C 2 -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, R x , OR a , SR a , NO 2 , NR c R d , NR b (C═O)R a , NR b (C═O)NR c R d , C(═O)R a , C(═O)OR a , C(═O)NR c R d , S(O) n R a , S(O) n NR c R d , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkylen-OR a , C 1 -C 4 -alkylen-NR c R d , C 6 -C 10 -aryl, C 5 -C 10 -hetaryl, C 5 -C 10 -hetaryl-C 1 -C 2 -alkyl, C 5 -C 10 -carbocyclyl, C 5 -C 10 -carbocyclyl-C 1 -C 2 -alkyl, C 5 -C 10 -heterocyclyl, and C 5 -C 10 -heterocyclyl-C 1 -C 2 -alkyl, wherein the C 6 -C 10 -aryl, C 5 -C 10 -hetaryl, C 5 -C 10 -carbocyclyl, and C 5 -C 10 -heterocyclyl moieties optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of halogen, CN, NO 2 , OH, SH, NH 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -dialkylamino, and C 1 -C 4 -haloalkyl;
R a is selected from the group consisting of H, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, and C 5 -C 10 -hetaryl or C 6 -C 10 -aryl, wherein the C 5 -C 10 -hetaryl or C 6 -C 10 -aryl moieties optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of halogen, CN, OH, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 5 -C 6 -hetaryl and C 6 -aryl, wherein said C 5 -C 6 -hetaryl and C 6 -aryl moieties optionally carry 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, CN, OH, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, and C 2 -C 4 -alkynyl;
R b is selected from the group consisting of H, C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 8 -alkynyl, and C 6 -C 10 -aryl;
R c and R d are independently of each other selected from the group consisting of H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 8 -cycloalkyl, C 6 -C 10 -aryl, and C 5 -C 10 -hetaryl;
or R c and R d 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, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -haloalkoxy;
R x is

V, W, X, Y, and Z are independently selected from the group consisting of N, CH and CR y ,
R Y is selected from the group consisting of halogen, CN, NO 2 , OH, SH, NH 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -dialkylamino, and C 1 -C 4 -haloalkyl;
m is 0, 1, or 2;
n is 0, 1, or 2; and
p is 0, 1, or 2.

3. The method according to claim 2 , wherein:
R 1 and R 2 are H; and
p is 1 or 2.

4. The method according to claim 2 , wherein:
R 3 is selected from the group consisting of:
(i) C(═O)R a , C(═N—OH)R a , or C(═N—R x )NR c R d ;
(ii) C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, or C 2 -C 8 -alkynyl, wherein the C-atoms of these groups optionally carry 1, 2, or 3 identical or different substituents selected from the group consisting of halogen and CN;
(iii) C 6 -C 14 -aryl, C 5 -C 14 -hetaryl, C 6 -C 14 -aryl-C 1 -C 2 -alkyl, and C 5 -C 14 -hetaryl-C 1 -C 2 -alkyl, wherein the aromatic moieties optionally carry 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, CN, R x , OR a , SR a , NO 2 , NR c R d , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 6 -C 10 -aryl, C 6 -C 10 -aryl-C 1 -C 2 -alkyl, C 5 -C 10 -hetaryl, C 5 -C 10 -hetaryl-C 1 -C 2 -alkyl, C 5 -C 10 -carbocyclyl, C 5 -C 10 -carbocyclyl-C 1 -C 2 -alky

Assignees

• Basf Se

Inventors

• Nave Barbara
• Dickhaut Joachim
• Nesvadba Peter
• Sisay Mihiret Tekeste
• Wissemeier Alexander
• Zerulla Wolfram
• Pasda Gregor
• Wallquist Olof
• Cunningham Allan F

Classifications

• C07D239/38

  One sulfur atom · CPC title

• C07C337/08 Primary

  the other nitrogen atom being further doubly-bound to a carbon atom, e.g. thiosemicarbazones · CPC title

• Y02E50/30

  Fuel from waste, e.g. synthetic alcohol or diesel · CPC title

• C05F11/00

  Other organic fertilisers · CPC title

• C07C323/07

  the carbon skeleton containing six-membered aromatic rings · CPC title