IP Library Granted Patent US 11,306,036
Granted Patent B2
US 11,306,036 · App. 16/315,631 · Granted Apr 19, 2022

Composition containing a urease inhibitor

Inventors: Zixian Chen (Singapore, SG); Krish Murthy Shanmuga (Plainsboro, NJ)
Assignee: RHODIA OPERATIONS
C05G3/90A01N25/22A01N57/02C05C9/00C09K15/26Y02P60/21
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Quick Facts
Patent No.
US 11,306,036
App. No.
16/315,631
Granted
Apr 19, 2022
Kind
B2
Abstract

The present invention relates to a composition comprising: (A) at least one (thio)phosphoric acid triamide and/or (thio)phosphoric acid diamide; (B) at least one amine compound; and optionally (C) a solvent. Said composition can notably be used in urea-containing fertilizers.

Claims (143)

1. A composition for use with a urea-containing fertilizer comprising:

(A) at least one (thio)phosphoric acid triamide of general formula (I) and/or (thio)phosphoric acid diamide of general formula (II)

R 1 R 2 N—P(X)(NH 2 ) 2   (I)

R 1 O—P(X)(NH 2 ) 2   (II)

wherein X is oxygen or sulphur;

R 1 and R 2 is independently selected from the group consisting of hydrogen, substituted or unsubstituted 2-nitrophenyl, C 1-10 alkyl, C 3-10 cycloalkyl, C 3-10 heterocycloalkyl, C 6-10 aryl, C 6-10 heteroaryl and diaminocarbonyl, or R 1 and R 2 , together with the nitrogen atom joining them, form a 5- or 6-membered saturated or unsaturated heterocyclic moiety, which optionally contains one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur;

(B) at least one amine compound selected from:

(B1) a compound having the general formula (III)

wherein:

Y is nitrogen or oxygen atom;

a and b is independently an integer of 2 to 6;

c is an integer of 2 to 10;

R 3 , R 4 , and R 6 is independently a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group;

R 5 is a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group or H;

R 7 is H, a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group when Y is nitrogen, R 7 is null when Y is oxygen;

(B2) a compound having the general formula (IV):

wherein:

d is an integer of 2 to 6;

e is an integer of 3 to 50 when d=2, e is an integer of 1 to 50 when d=3-6;

R 8 and R 9 , same or different, is a C 1-4 alkyl group, or R 8 and R 9 , same or different, is a C 1-4 hydroxylalkyl group, or R 8 and R 9 , same or different, is a C 1-4 alkoxyl group;

R 10 is H or a C 1-4 alkyl group;

(B3) 3-dimethylaminopropylamine

(B4) a compound having the general formula (VI)

wherein:

Z 1 , Z 2 , Z 3 is independently nitrogen or oxygen atom, wherein at least one of Z 1 , Z 2 , Z 3 is nitrogen atom;

R 15 , R 16 , R 17 , R 18 , R 19 and R 20 is independently a C 1-12 alkyl or hydroxylalkyl group, a C 1-12 alkoxyl group, H or null.

2. The composition according to claim 1 , wherein the amine compound is according to the general formula (III)

wherein:

Y is nitrogen or oxygen atom;

a and b is independently an integer of 2 to 6;

c is an integer of 2 to 10;

R 3 , R 4 , and R 6 is independently a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group;

R 5 is a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group or H;

R 7 is H, a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group when Y is nitrogen, R 7 is null when Y is oxygen.

3. The composition according to claim 2 , wherein R 3 , R 4 , R 5 and R 6 as defined in the general formula (III) are independently a C 1-4 alkyl group.

4. The composition according to claim 1 , wherein the amine compound is a compound having general formula (VII):

wherein:

Y 1 is nitrogen or oxygen atom;

g and h is independently an integer of 2-6;

R 21 , R 22 , R 24 is independently a C 1-4 alkyl or hydroxylalkyl group, or a C 1-4 alkoxyl group;

R 23 is a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group or H;

R 25 is H, a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group when Y 1 is nitrogen; and

R 25 is null when Y 1 is oxygen.

5. The composition according to claim 4 , wherein R 21 , R 22 , R 23 , R 24 as defined in the general formula (VII) are independently a C 1-4 alkyl.

6. The composition according to claim 1 , wherein the amine compound is a compound having the general formula (IV)

wherein:

d is an integer of 2 to 6;

e is an integer of 3 to 50 when d=2, e is an integer of 1 to 50 when d=3-6;

R 8 and R 9 , same or different, is a C 1-4 alkyl group, or R 8 and R 9 , same or different, is a C 1-4 hydroxylalkyl group, or R 8 and R 9 , same or different, is a C 1-4 alkoxyl group;

R 10 is H or a C 1-4 alkyl group.

7. The composition according to claim 1 , wherein the amine compound is a compound having the general formula (VI)

wherein:

Z 1 , Z 2 , Z 3 is independently nitrogen or oxygen atom, wherein at least one of Z 1 , Z 2 , Z 3 is nitrogen atom;

R 15 , R 16 , R 17 , R 18 , R 19 and R 20 is independently a C 1-12 alkyl or hydroxylalkyl group, a C 1-12 alkoxyl group, H or null.

8. A composition for use with a urea-containing fertilizer comprising:

(A) at least one (thio)phosphoric acid triamide of general formula (I) and/or (thio)phosphoric acid diamide of general formula (II)

R 1 R 2 N—P(X)(NH 2 ) 2   (I)

R 1 O—P(X)(NH 2 ) 2   (II)

wherein X is oxygen or sulphur;

R 1 and R 2 is independently selected from the group consisting of hydrogen, substituted or unsubstituted 2-nitrophenyl, C 1-10 alkyl, C 3-10 cycloalkyl, C 3-10 heterocycloalkyl, C 6-10 aryl, C 6-10 heteroaryl and diaminocarbonyl, or R 1 and R 2 , together with the nitrogen atom joining them, form a 5- or 6-membered saturated or unsaturated heterocyclic moiety, which optionally contains one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur;

(B) at least one amine compound selected from:

(B1) a compound having the general formula (III)

wherein:

Y is nitrogen or oxygen atom;

a and b is independently an integer of 2 to 6;

c is an integer of 1 to 10;

R 3 , R 4 , and R 6 is independently a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group;

R 5 is a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group or H;

R 7 is H, a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group when Y is nitrogen, R 7 is null when Y is oxygen;

(B2) a compound having the general formula (IV):

wherein:

d is an integer of 2 to 6;

e is an integer of 2 to 50 when d=2, e is an integer of 1 to 50 when d=3-6;

R 8 and R 9 , same or different, is a C 1-4 alkyl group, or R 8 and R 9 , same or different, is a C 1-4 hydroxylalkyl group, or R 8 and R 9 , same or different, is a C 1-4 alkoxyl group;

R 10 is H or a C 1-4 alkyl group;

(B3) 3-dimethylaminopropylamine

(B4) a compound having the general formula (VI)

wherein:

Z 1 , Z 2 , Z 3 is independently nitrogen or oxygen atom, wherein at least one of Z 1 , Z 2 , Z 3 is nitrogen atom;

R 15 , R 16 , R 17 , R 18 , R 19 and R 20 is independently a C 1-12 alkyl or hydroxylalkyl group, a C 1-12 alkoxyl group, H or null, wherein the amine compound is a compound having the general formula (VIII):

wherein:

R 26 and R 27 is independently a C 1-12 alkyl or hydroxylalkyl group, a C 1-12 alkoxyl group or H.

9. The composition according to claim 1 , wherein the amine compound is selected from the group consisting of:

3,3′-iminobis(N,N-dimethylpropylamine) (TMBPA);

3-dimethylaminopropylamine (DMAPA);

3-am inopropane-1,2-diol;

1-[bis[3-(dimethylamino)propyl]amino]-2-propanol;

bis[2-(N,N-dimethylamino)ethyl] ether;

2-(2-(dimethylam ino)ethoxy)ethanol;

N,N,N′,N″,N″-pentamethyldiethylene triamine, and mixtures thereof.

10. The composition according to claim 1 , wherein the amine compound is selected from the group consisting of 3,3′-iminobis(N,N-dimethylpropylamine), 1-[bis[3-(dimethylamino)propyl]amino]-2-propanol, bis[2-(N, N-dimethylamino)ethyl] ether, N, N, N′,N″, N″-pentamethyldiethylene triamine, and mixtures thereof.

11. The composition according to claim 1 , wherein component (A) is N-alkylthiophosphoric acid triamide or N-alkylphosphoric acid triamide.

12. The composition according to claim 1 , wherein component (A) is N-(n-butyl)thiophosphoric acid triamide (NBPT).

13. The composition according to claim 1 , wherein the composition further comprises a solvent.

14. The composition according to claim 13 , wherein said solvent is a compound having the general formula (X):

wherein:

m is an integer of 1 to 10;

R 31 and R 32 is independently H, a C 1-10 alkyl group, a C 1-10 alkenyl group, or a phenyl group.

15. The composition according to claim 1 , wherein the component (B) is present in an amount of 2% to 25% by weight based on the total weight of the composition.

16. A composition for use with a urea-containing fertilizer comprising:

(A) at least one (thio)phosphoric acid diamide of general formula (II)

R 1 O—P(X)(NH 2 ) 2   (II)

wherein X is oxygen or sulphur;

R 1 and R 2 is independently selected from the group consisting of hydrogen, substituted or unsubstituted 2-nitrophenyl, C 1-10 alkyl, C 3-10 cycloalkyl, C 3-10 heterocycloalkyl, C 6-10 aryl, C 6-10 heteroaryl and diaminocarbonyl, or R 1 and R 2 , together with the nitrogen atom joining them, form a 5- or 6-membered saturated or unsaturated heterocyclic moiety, which optionally contains one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur;

(B) at least one amine compound selected from:

(B1) a compound having the general formula (III)

wherein:

Y is nitrogen or oxygen atom;

a and b is independently an integer of 2 to 6;

c is an integer of 1 to 10;

R 3 , R 4 , and R 6 is independently a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group;

R 5 is a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group or H;

R 7 is H, a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group when Y is nitrogen, R 7 is null when Y is oxygen;

(B2) a compound having the general formula (IV):

wherein:

d is an integer of 2 to 6;

e is an integer of 2 to 50 when d=2, e is an integer of 1 to 50 when d=3-6;

R 8 and R 9 , same or different, is a C 1-4 alkyl group, or R 8 and R 9 , same or different, is a C 1-4 hydroxylalkyl group, or R 8 and R 9 , same or different, is a C 1-4 alkoxyl group;

R 10 is H or a C 1-4 alkyl group;

(B3) a compound having the general formula (V)

wherein:

f is an integer of 3 to 6;

R 11 and R 12 is independently a C 1-4 alkyl or hydroxylalkyl group, or a C 1-4 alkoxyl group;

R 13 and R 14 is independently a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group or H;

(B4) a compound having the general formula (VI)

wherein:

Z 1 , Z 2 , Z 3 is independently nitrogen or oxygen atom, wherein at least one of Z 1 , Z 2 , Z 3 is nitrogen atom;

R 15 , R 16 , R 17 , R 18 , R 19 and R 20 is independently a C 1-12 alkyl or hydroxylalkyl group, a C 1-12 alkoxyl group, H or null.

17. A composition for use with a urea-containing fertilizer comprising:

(A) at least one (thio)phosphoric acid triamide of general formula (I) and/or (thio)phosphoric acid diamide of general formula (II)

R 1 R 2 N—P(X)(NH 2 ) 2   (I)

R 1 O—P(X)(NH 2 ) 2   (II)

wherein X is oxygen or sulphur;

R 1 and R 2 is independently selected from the group consisting of hydrogen, substituted or unsubstituted 2-nitrophenyl, C 1-10 alkyl, C 3-10 cycloalkyl, C 3-10 heterocycloalkyl, C 6-10 aryl, C 6-10 heteroaryl and diaminocarbonyl, or R 1 and R 2 , together with the nitrogen atom joining them, form a 5- or 6-membered saturated or unsaturated heterocyclic moiety, which optionally contains one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur;

(B) at least one amine compound

wherein the amine compound is a compound having general formula (VII):

wherein:

Y 1 is nitrogen or oxygen atom;

g and h is independently an integer of 2-6;

R 21 , R 22 , R 24 is independently a hydroxylalkyl group, or a C 1-4 alkoxyl group;

R 23 is a hydroxylalkyl group, a C 1-4 alkoxyl group or H;

R 25 is H, a C 1-4 alkyl or hydroxylalkyl group, a C 1-4 alkoxyl group when Y 1 is nitrogen; and

R 25 is null when Y 1 is oxygen.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2023
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 065488/0365 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2019
From: CHEN, ZIXIAN; SHANMUGA, KRISH
To: RHODIA OPERATIONS
Reel/Frame 049573/0097 →
Continuity (2)
Provisional Application 62358268 · Jul 5, 2016
Related Publication 20190300452A1 · Oct 3, 2019