Use of N-functionalized alkoxy pyrazole compounds as nitrification inhibitors

Patent metadata

Field	Value
Publication number	US-12060308-B2
Application number	US-202318156209-A
Country	US
Kind code	B2
Filing date	Jan 18, 2023
Priority date	Feb 28, 2018
Publication date	Aug 13, 2024
Grant date	Aug 13, 2024

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 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 CHR a OR b ;
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 x is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy;
n is 0, 1, or 2.

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

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

4. The compound 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.

5. A composition comprising at least one compound of formula I as defined in claim 1 and at least one carrier.

6. The compound of claim 1 , wherein a reduction of nitrification occurs in or on a plant, in a root zone of a plant, in or on soil or soil substituents and/or at a locus where the plant is growing or is intended to grow.

7. A method for reducing nitrification, comprising treating a plant growing on soil or soil substituents and/or the locus or soil or soil substituents where the plant is growing or is intended to grow, with at least one compound of formula I as defined in claim 1 .

8. The method of claim 7 , wherein the plant and/or the locus or soil or soil substituents where the plant is growing or is intended to grow is additionally provided with a fertilizer.

9. The method of claim 8 , wherein the application of said compound of formula I and of said fertilizer is carried out simultaneously or with a time lag.

10. The method of claim 9 , wherein the time lag is 1 day, 2 days, 3 days, 1 week, 2 weeks, or 3 weeks.

11. The method of claim 7 , wherein said plant is an agricultural plant, a vegetable; sorghum; a silvicultural plant; an ornamental plant; or a horticultural plant, each in its natural or in a genetically modified form.

12. The method of claim 11 , wherein the agricultural plant or vegetable is selected from the group consisting of wheat, barley, oat, rye, soybean, corn, potatoes, oilseed rape, canola, sunflower, cotton, sugar cane, sugar beet, rice, spinach, lettuce, asparagus, and cabbage.

13. A method for treating a fertilizer, comprising applying a nitrification inhibitor as defined in claim 1 to the fertilizer.

14. The method of claim 13 , wherein said fertilizer is a solid or liquid ammonium-containing inorganic fertilizer; a solid or liquid organic fertilizer, or a urea-containing fertilizer.

15. The method of claim 14 , 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, 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

• C05C9/00

  Fertilisers containing urea or urea compounds · CPC title

• Y02W30/40

  Bio-organic fraction processing; Production of fertilisers from the organic fraction of waste or refuse · CPC title

• Y02E50/30

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

• C07D403/12 Primary

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

• C05G3/90 Primary

  for affecting the nitrification of ammonium compounds or urea in the soil · CPC title