PYRAZOLE COMPOUNDS AS NITRIFICATION INHIBITORS

• US 20180016199A1
• Filed: 02/05/2016
• Published: 01/18/2018
• Est. Priority Date: 02/06/2015
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Nave, Barbara, Dickhaut, Joachim, Nesvadba, Peter, Sisay, Mihiret Tekeste, Wissemeier, Alexander, Zerulla, Wolfram, Pasda, Gregor, Wallquist, Olof, Cunningham, Allan F
• Granted Patent: US 10,556,844 B2
• Time in Patent Office: Days
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/58 1,2-Diazines; Hydrogenated 1,2-diazines
• CPC Class Codes: C05C 3/00 Fertilisers containing other salts of ammonia or ammonia itself, e.g. gas liquor
• CPC Class Codes: C05G 3/90 for affecting the nitrification of ammonium compounds or urea in the soil
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 231/14 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 231/18 One oxygen or sulfur atom
• CPC Class Codes: C07D 231/20 One oxygen atom attached in position 3 or 5
• CPC Class Codes: C07D 231/54 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 231/56 Benzopyrazoles; Hydrogenated benzopyrazoles
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: Y02P 60/21 Dinitrogen oxide [N2O], e.g. using aquaponics, hydroponics or efficiency measures

Abstract

Pyrazole derivatives as nitrification inhibitors are described herein.

Claims

1. A pyrazole compound of formula I for use as a nitrification inhibitor

2. The pyrazole compound of claim 1, wherein:

R¹ is a terminal C₃-C₄-alkynyl group.

3. The pyrazole compound of claim 1, wherein:

R¹ is a terminal C₃-C₄-allenyl group.

4. The pyrazole compound of claim 1, wherein:

R², R³ and R⁴ are independently of each other selected from H, halogen, CN, OR^a, C(═

O)R^a, C(═

O)OR^a, C(═

O)NR^cR^d;

C₁-C₈-alkyl, wherein the C-atoms may be unsubstituted or may carry 1, 2, 3 identical or different substituents selected from halogen, CN, and OR^a;

C₆-C₁₀-aryl, and C₅-C₁₀-hetaryl, wherein the aromatic moieties may in each case be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from halogen, CN, OR^a, C₁-C₄-alkyl, C₁-C₄-haloalkyl, and C₂-C₄-alkynyl;

or R³ and R⁴ together form a bridge, which forms together with the atoms to which R³ and R⁴ are bonded an annulated partly or fully unsaturated, or aromatic 5 to 10-membered carbocyclic ring, wherein the carbocyclic ring may be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from ═

O, halogen, CN, OR^a, O(C═

O)NR^cR^d, C₅-C₁₀-hetaryl, and C₅-C₁₀-heterocyclyl, wherein the C₅-C₁₀-hetaryl, and C₅-C₁₀-heterocyclyl moieties may be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from ═

O, halogen, CN, and C₁-C₄-haloalkyl;

or R² and R⁴ together form a bridge, which forms together with the atoms to which R² and R⁴ are bonded an annulated partly or fully unsaturated, or aromatic 5 to 10-membered carbocyclic ring, wherein the carbocyclic ring may be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from ═

O, halogen, CN, OR^a, O(C═

O)NR^cR^d, C₅-C₁₀-hetaryl, and C₅-C₁₀-heterocyclyl, wherein the C₅-C₁₀-hetaryl, and C₅-C₁₀-heterocyclyl moieties may be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from ═

O, halogen, CN, and C₁-C₄-haloalkyl;

and wherein

R^a is H, C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₂-C₈-alkynyl;

C₅-C₁₀-hetaryl or C₆-C₁₀-aryl, wherein the C₅-C₁₀-hetaryl or C₆-C₁₀-aryl moieties may each be unsubstituted or may carry 1, 2, 3, 4, or 5 identical or different substituents selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkynyl, C₅-C₆-hetaryl and C₆-aryl, wherein said C₅-C₆-hetaryl and C₆-aryl moieties may be unsubstituted or may carry 1, 2, 3, 4, or 5 substituents selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, and C₂-C₄-alkynyl; and

R^c and R^d are independently of each other selected from the group consisting of H, C₁-C₄-alkyl, C₃-C₈-cycloalkyl, and C₅-C₁₀-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.

5. The pyrazole compound of claim 1, wherein:

R¹ is propargyl, and

R², R³ and R⁴ are independently of each other selected from H, OH, C₁-C₂-alkyl, C₁-C₂-alkoxy, OC(═

O)C₁-C₂-alkyl, C(═

O)OOC₁—

C₂-alkyl, and C(═

O)OOH,

or R² and R⁴, Or R³ and R⁴ together form a bridge, which forms together with the atoms to which the substituents are bonded an annulated saturated, partly or fully unsaturated, or aromatic 5 to 10-membered monocyclic or bicyclic carbocyclic ring, wherein the carbocyclic ring may be unsubstituted or may carry 1, 2, or 3 identical or different substituents selected from ═

O, halogen, C₁-C₂-haloalkyl, C₁-C₂-alkyl and C₁-C₂-alkoxy.

6. A composition for use in reducing nitrification comprising at least one compound of formula I as defined in claim 1 and at least one carrier.

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

and (ii) at least one compound of formula I as defined in claim 1.

8. The pyrazole compound of claim 1, wherein said compound of formula I is used in combination with a fertilizer as an agrochemical mixture.

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

10. A method for reducing nitrification, comprising treating at least one of a plant growing on soil or soil substituents and the locus, 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.

11. The method of claim 10 further comprising providing a fertilizer to the at least one of the plant and the locus, soil or soil substituents where the plant is growing or is intended to grow.

12. The method of claim 11, wherein the application of said compound of formula I and of said fertilizer are carried out simultaneously or with a time lag between the application of said compound of formula I and of said fertilizer.

13. A method for treating a fertilizer or a composition, comprising the application of a nitrification inhibitor as defined in claim 1.

14. The agrochemical mixture of claim 7, wherein said fertilizer is one of the following:

(i) a solid or liquid ammonium-containing inorganic fertilizer;

(ii) a solid or liquid organic fertilizer; and

(iii) an urea-containing fertilizer.

15. The method of claim 10, wherein said plant is one of the following:

(i) an agricultural plant;

(ii) a vegetable;

(iii) sorghum;

(iv) a silvicultural plant;

(v) an ornamental plant; and

(vi) a horticultural plant, wherein said plant is in its natural form or in a genetically modified form.

16. The pyrazole compound of claim 1, wherein:

R¹ is C₃-allenyl, and

R², R³ and R⁴ are independently of each other selected from H, OH, C₁-C₂-alkyl, C₁-C₂-alkoxy, OC(═

O)C₁-C₂-alkyl, C(═

O)OOC₁—

C₂-alkyl, and C(═

O)OOH,

or R² and R⁴, or R³ and R⁴ together form a bridge, which forms together with the atoms to which the substituents are bonded an annulated saturated, partly or fully unsaturated, or aromatic 5 to 10-membered monocyclic or bicyclic carbocyclic ring, wherein the carbocyclic ring may be unsubstituted or may carry 1, 2, or 3 identical or different substituents selected from ═

O, halogen, C₁-C₂-haloalkyl, C₁-C₂-alkyl and C₁-C₂-alkoxy.

17. The pyrazole compound of claim 4, wherein in said compound of formula I, R², R³ and R⁴ are independently of each other selected from H, halogen, OR^a, C(═

O)OR^a, and C₁-C₄-alkyl;

and wherein

R^a is H, C₁-C₈-alkyl, or C₁-C₈-haloalkyl.

18. The pyrazole compound of claim 4, wherein in said compound of formula I, R³ and R⁴ together form a bridge, which forms together with the atoms to which R³ and R⁴ are bonded an annulated partly or fully unsaturated, or aromatic 5 to 10-membered carbocyclic ring, wherein the carbocyclic ring may be unsubstituted or may carry 1, 2, or 3 identical or different substituents selected from ═

O, halogen, CN, and OR^a,

and wherein

R^a is H, C₁-C₈-alkyl, or C₁-C₈-haloalkyl.