Use of N-functionalized alkoxy pyrazole compounds as nitrification inhibitors

Patent metadata

Field	Value
Publication number	US-12559442-B2
Application number	US-202418756040-A
Country	US
Kind code	B2
Filing date	Jun 27, 2024
Priority date	Feb 28, 2018
Publication date	Feb 24, 2026
Grant date	Feb 24, 2026

Abstract

The present invention relates to the use of novel nitrification inhibitors of formula I, which are N-functionalized alkoxy pyrazole 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.

First claim

The invention claimed is:

1 . An agrochemical mixture comprising (i) at least one fertilizer and (ii) at least one N-functionalized alkoxy pyrazole compound of formula I

or a salt, stereoisomer, tautomer, or N-oxide thereof,
wherein
R 1 is H, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, benzyl, allyl, CHR a C(═O)OR b , CHR a C(═O)NR b R c , or phenyl, wherein said phenyl group is unsubstituted or substituted by one or more, same or different substituents R x ;
R 2 is halogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, benzyl, allyl, propargyl, or phenyl, wherein said phenyl group is unsubstituted or substituted by one or more, same or different substituents R x ;
R N is C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, benzyl, allyl, or phenyl, wherein said groups are unsubstituted or substituted by one or more, same or different substituents R y ;
CHR a C(═O)OR b , CHR a C(═O)NR b R c , CH(C(═O)OR b ) CH 2 (C(═O)OR b );
C(═O)R d , C(═O)OR b , C(═O)NR b R c , CHR a OR b , or CHR a NR e (C═O)R f ;

and wherein
R a is H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 8 -cycloalkyl, phenyl, or phenyl-C 1 -C 2 -alkyl;
R b is H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 8 -cycloalkyl, phenyl, or phenyl-C 1 -C 2 -alkyl;
R c is H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, or phenyl;
R d is H, C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, phenyl, or phenyl-C 1 -C 2 -alkyl, wherein these groups are unsubstituted or substituted by a group COOH;
R e is H, C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, or C 6 -C 10 -aryl;
R f is H, or C 1 -C 4 -alkyl;
R x is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy;
R y is halogen, CN, OH, NO 2 , COOH, NR b R c , NR b (C═O)R f , C(═O)NR b R c , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylcarboxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, and S(O) 2 NR b R c ;
n is 0, 1, or 2.

2 . The agrochemical mixture of claim 1 , wherein
R 1 is C 1 -C 6 -alkyl, benzyl, allyl.

3 . The agrochemical mixture of claim 1 , wherein
n is 0; or n is 1, and R 2 is C 1 -C 3 -alkyl or phenyl.

4 . The agrochemical mixture of claim 1 , wherein
R N is C(═O)R d , CHR a C(═O)OR b , CHR a C(═O)NR b R c , CH(C(═O)OR b )CH 2 (C(═O)OR b ), or CHR a NR e (C═O)R f .

5 . The agrochemical mixture of claim 1 , wherein
R a is H; R b is H or C 1 -C 4 -alkyl; R c is H or C 1 -C 4 -alkyl; R d is C 1 -C 3 -alkyl; R e is H; R f is H or CH 3 .

6 . The agrochemical mixture of claim 1 , wherein said fertilizer is a solid or liquid ammonium-containing inorganic fertilizer; a solid or liquid organic fertilizer, or a urea-containing fertilizer.

7 . The agrochemical mixture of claim 1 , wherein the fertilizer is selected from the group consisting of an NPK fertilizer, ammonium nitrate, calcium ammonium nitrate, ammonium sulfate nitrate, ammonium sulfate, ammonium phosphate, liquid manure, semi-liquid manure, biogas manure, stable manure and straw manure, worm castings, compost, seaweed, guano, urea, formaldehyde urea, anhydrous ammonium, urea ammonium nitrate (UAN) solution, urea sulphur, urea based NPK-fertilizers, and urea ammonium sulfate.

Assignees

• Basf Se

Inventors

• Nesvadba Peter
• Cunningham Allan F
• Hindalekar Shrirang
• Nave Barbara
• Pothi Tejas
• Wallquist Olof
• Wissemeier Alexander

Classifications

• C07D231/20

  One oxygen atom attached in position 3 or 5 · CPC title

• C05C9/00

  Fertilisers containing urea or urea compounds · CPC title

• C05C3/00

  Fertilisers containing other salts of ammonia or ammonia itself, e.g. gas liquor · CPC title

• A01N43/56 Primary

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

• C07D471/04

  Ortho-condensed systems · CPC title