Pyrazole compounds as nitrification inhibitors

Patent metadata

Field	Value
Publication number	US-10556844-B2
Application number	US-201615548561-A
Country	US
Kind code	B2
Filing date	Feb 5, 2016
Priority date	Feb 6, 2015
Publication date	Feb 11, 2020
Grant date	Feb 11, 2020

Abstract

Pyrazole derivatives as nitrification inhibitors are described herein.

First claim

The invention claimed is:

1. 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 is C 4 -C 6 -alkynyl, propargyl, or C 3 -C 6 -allenyl, wherein the C-atoms of these groups optionally carry 1, 2, or 3 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 , O(C═O)R a , C(═O)R a , C(═O)OR a , C(═O)NR c R d , S(O) m R a , and S(O) m NR c R d ;
R 2 , R 3 and R 4 are independently selected from the group consisting of H, 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) m R a , S(O) m NR c R d ; C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, 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, 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) m R a , and S(O) m NR c R d ; C 6 -C 10 -aryl, and C 5 -C 10 -hetaryl, wherein the aromatic moieties optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of halogen, CN, OR a , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, and C 2 -C 4 -alkynyl;
or R 3 and R 4 together form a bridge, which forms together with the atoms to which R 3 and R 4 are bonded an annulated partly or fully unsaturated, or aromatic 5 to 10-membered carbocyclic or heterocyclic ring, wherein the heterocyclic ring may carry 1, 2, or 3 heteroatoms being selected from O, S, and N, of which at least one of S and N may optionally be oxidized, and wherein the carbocyclic or heterocyclic ring optionally carries carries 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of ═O, 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 , O(C═O)NR c R d , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 6 -C 10 -aryl, C 5 -C 10 -hetaryl, C 5 -C 10 -carbocyclyl, and C 5 -C 10 -heterocyclyl, 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 ═O, halogen, CN, C 1 -C 4 -alkyl, and C 1 -C 4 -haloalkyl;
or R 2 and R 4 together form a bridge, which forms together with the atoms to which R 2 and R 4 are bonded an annulated partly or fully unsaturated, or aromatic 5 to 10-membered carbocyclic or heterocyclic ring, wherein the heterocyclic ring may carry 1, 2, or 3 heteroatoms being selected from O, S, and N, of which at least one of S and N may optionally be oxidized, and wherein the carbocyclic or heterocyclic ring optionally carries carries 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of ═O, 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 , O(C═O)NR c R d , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 6 -C 10 -aryl, C 5 -C 10 -hetaryl, C 5 -C 10 -carbocyclyl, and C 5 -C 10 -heterocyclyl, 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 ═O, halogen, CN, C 1 -C 4 -alkyl, and C 1 -C 4 -haloalkyl;
R a is selected from the group consisting of H, C 1 -C 8 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl; C 5 -C 10 -hetaryl and 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 o and R d are independently 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 may carry a further heteroatom being selected from O, S, and N as a ring member atom, of which at least one S and N may optionally be 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; and
m is 0, 1, or 2.

2. The method according to claim 1 , wherein:
R 1 is a terminal C 4 -alkynyl group or propargyl.

3. The method according to claim 1 , wherein:
R 1 is a terminal C 3 -C 4 -allenyl group.

4. The method according to claim 1 , wherein:
R 2 , R 3 and R 4 are independently selected from the group consisting of H, halogen, CN, OR a , C(═O)R a , C(═O)OR a , C(═O)NR c R d ; C 1 -C 8 -alkyl, wherein the C-atoms optionally carry 1, 2, 3 identical or different substituents selected from the group consisting of halogen, CN, OR a ; C 6 -C 10 -aryl, and C 5 -C 10 -hetaryl, wherein the aromatic moieties optionally carry 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of halogen, CN, OR a , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, and C 2 -C 4 -alkynyl;
or R 3 and R 4 together form a bridge, which forms together with the atoms to which R 3 and R 4 are bonded an annulated partly or fully unsaturated, or aromatic 5 to 10-membered carbocyclic ring, wherein the carbocyclic ring optionally carries 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of ═O, halogen, CN, OR a , O(C═O)NR c R d , C 5 -C 10 -hetaryl, and C 5 -C 10 -heterocyclyl, wherein the C 5 -C 10 -hetaryl, 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 ═O, halogen, CN, and C 1 -C 4 -haloalkyl;
or R 2 and R 4 together form a bridge, which forms together with the atoms to which R 2 and R 4 are bonded an annulated partly or fully unsaturated, or aromatic 5 to 10-membered carbocyclic ring, wherein the carbocyclic ring optionally carries 1, 2, 3, 4, or 5 identical or different substituents selected from the group consisting of ═O, halogen, CN, OR a , O(C═O)NR c R d , C 5 -C 10 -hetaryl, and C 5 -C 10 -heterocyclyl, wherein the C 5 -C 10 -hetaryl, 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 ═O, halogen, CN, 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 -alkynyl; 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, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, 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 subs

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

• C07D231/56

  Benzopyrazoles; Hydrogenated benzopyrazoles · CPC title

• C07D231/12 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D403/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• A01N43/56 Primary

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title