IP Library Granted Patent US 9,420,780
Granted Patent B2
US 9,420,780 · App. 14/350,599 · Granted Aug 23, 2016

Composition, method for producing the composition, and phytosanitary formulation containing same

Inventors: Thierry Vidal (Lyons, FR); Benoit Abribat (Saint Fargeau Ponthierry, FR); Valerio Bramati (Arese, IT); Marc Balastre (Paris, FR)
Assignee: RHODIA OPERATIONS
A01N25/02A01N25/04
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Quick Facts
Patent No.
US 9,420,780
App. No.
14/350,599
Granted
Aug 23, 2016
Kind
B2
Abstract

The present disclosure relates to compositions comprising from 10 to 90 wt % of a mixture M of compounds A having formula R 1 CONR 2 R 3 , wherein R 1 , R 2 , and R 3 are described herein, and from 10 to 90 wt % of at least one compound B selected from the amide solvents, optionally combined with an ester solvent, and methods for producing the same. The present disclosure further relates to phytosanitary formulations comprising such compositions.

Claims (66)

1. A composition comprising:

from 10% to 90% by weight of a mixture M of compounds A having the formula (I):

R 1 CONR 2 R 3   (I)

the said mixture comprising at least two compounds A having different formulas (I), wherein:

R 1 is a group having the formula —Z—COOR′, where Z is a linear or branched divalent alkylene group comprising from 2 to 4 carbon atoms and R′ is a methyl group;

R 2 and R 3 , which are identical or different, are methyl or ethyl groups; and

from 10% to 90% by weight of at least one compound B selected from amide solvents, optionally in combination with an ester solvent.

2. A composition according to claim 1 , in which the mixture M is a mixture of compounds having the formula (I), the mixture comprising:

a compound having the formula (I) wherein R 1 is —CH(CH 2 —CH 3 )—CH 2 —COOMe,

a compound having the formula (I) wherein R 1 is —CH 2 —CH(CH 2 —CH 3 )—COOMe

a compound having the formula (I) wherein R 1 is —CH(CH 3 )—CH 2 —CH 2 —COOMe, and

a compound having the formula (I) wherein R 1 is —CH 2 —CH 2 —CH(CH 3 )—COOMe.

3. A composition according to claim 2 , in which the mixture M further comprises a compound having the formula (I) wherein R 1 is —(CH 2 ) 4 —COOMe.

4. A composition according to claim 1 , in which the mixture M comprises at least one compound A having the formula (I) wherein R 2 and R 3 are methyl groups.

5. A composition according to claim 1 , that comprises at least one amide solvent as compound B in a mixture with at least one ester solvent.

6. A composition according to claim 1 , in which the amide solvents are chosen from compounds having the formula (II):

R″—CONMe 2   (II)

where R″ is a linear or branched alkyl group, comprising of 8 to 20 carbon atoms.

7. A composition according to claim 6 , in which the amide solvents are chosen from the compounds having the formula (II) wherein R″ is selected from among the C8, C10, C12, C18 linear alkyls and mixtures thereof, in all ratios.

8. A composition according to claim 1 , in which the ester solvent is selected from the group consisting of 2-ethylhexyl lactate, alkyl acetates, esters of fatty acids, fatty esters of carboxylic acids and mixtures of methyl diesters of 2-ethyl succinic acid, methylglutaric acid and optionally adipic acid.

9. A composition according to claim 1 , comprising:

from 20% to 60% by weight of the mixture M, and

from 40% to 80% by weight of the compound B,

wherein the mixture M is a mixture of compounds having the formula (I), the mixture comprising:

a compound having the formula (I) wherein R 1 is —CH(CH 2 —CH 3 )—CH 2 —COOMe,

a compound having the formula (I) wherein R 1 is —CH 2 —CH(CH 2 —CH 3 )—COOMe

a compound having the formula (I) wherein R 1 is —CH(CH 3 )—CH 2 —CH 2 —COOMe, and

a compound having the formula (I) wherein R 1 is —CH 2 —CH 2 —CH(CH 3 )—COOMe; and

wherein compound B is selected from amide solvents, optionally in combination with an ester solvent.

10. A method for obtaining a composition of solvents having a water solubility of less than or equal to 1% by weight at 20° C.-25° C., the method comprising mixing from 10% to 90% by weight of at least one mixture M with 10% to 90% by weight of at least one compound B;

wherein the mixture M is a mixture of compounds A having the formula (I):

R 1 CONR 2 R 3   (I)

the said mixture comprising at least two compounds A having different formulas (I), wherein:

R 1 is a group having the formula —Z—COOR′, where Z is a linear or branched divalent alkylene group comprising from 2 to 4 carbon atoms and R′ is a methyl group;

R 2 and R 3 , which are identical or different, are methyl or ethyl groups; and

wherein compound B is selected from amide solvents, optionally in combination with an ester solvent.

11. A solvent having a water solubility of less than or equal to 1% by weight at 20° C.-25° C. comprising the composition according to claim 1 .

12. A phytosanitary formulation comprising at least one phytosanitary active ingredient and, as a solvent for the at least one phytosanitary active ingredient, the composition according to claim 1 .

13. A phytosanitary formulation according to claim 12 , wherein the phytosanitary formulation is in the form of an emulsifiable concentrate, a concentrated emulsion or a micro emulsion.

14. A phytosanitary formulation according to claim 12 , in which the phytosanitary active ingredient is selected from among the following compounds:

Abamectin,

Alachlor

Bromoxynil

Chlorpyrifos,

Alpha-cypermethrin,

Cyfluthrin,

Ethofenprox,

Flufenoxuron,

Lufenuron,

Myclobutanil,

Phenmedipham,

Prochloraz,

Propanil,

Pendimethalin,

Azoles,

Triadimenol,

Trifluralin,

Oxyfluorfen,

Imidacloprid,

Ethofumesate,

Dimethyl phosphate,

Dimethoate, and

Propoxur; and mixtures thereof.

15. A phytosanitary formulation according to claim 12 , wherein the solvent is from 10% to 90% by weight relative to the weight of the formulation.

16. A phytosanitary formulation according to claim 14 , wherein the azole is a triazole.

17. A phytosanitary formulation according to claim 16 , wherein the triazole is tebuconazole or uniconazole.

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 May 6, 2014
From: VIDAL, THIERRY; ABRIBAT, BENOIT; BRAMATI, VALERIO; BALASTRE, MARC
To: RHODIA OPERATIONS
Reel/Frame 032827/0927 →
Priority Claims (1)
FR 11 59258 · Oct 13, 2011 · national
Continuity (1)
Related Publication 20140256554A1 · Sep 11, 2014