IP Library Granted Patent US 9,392,785
Granted Patent B2
US 9,392,785 · App. 14/249,021 · Granted Jul 19, 2016

Use of esteramides as solvents, novel esteramides and process for preparing esteramides

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Quick Facts
Patent No.
US 9,392,785
App. No.
14/249,021
Granted
Jul 19, 2016
Kind
B2
Abstract

One subject of the present invention is the use, as solvents, of compounds of esteramide type. Another subject of the invention are particularly practical processes for preparing esteramides. Another subject of the invention are novel esteramides, which may in particular be used as solvents, for example in phytosanitary formulations.

Claims (37)

1. A composition comprising:

(a) an active substance selected from the group consisting of an insecticide, a herbicide, a fungicide, an acaricide, and a rodenticide;

(b) an esteramide compound of formula (I):

R 1 OOC-A-CONR 2 R 3   (I)

wherein:

R 1 is a radical selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36;

R 2 and R 3 are each methyl radicals; and

A is a linear divalent alkyl radical having an average number of carbon atoms ranging from 2 to 4, said radical being selected from among the radicals of the following formulae: —CH 2 —CH 2 —(ethylene), —CH 2 —CH 2 —CH 2 — (n-propylene), —CH 2 —CH 2 —CH 2 —CH 2 — (n-butylene),

excluding the following compounds: -MeOOC—CH 2 —CH 2 —CH—CONMe 2 and -MeOOC—CH 2 —CH 2 —CONMe 2 ;

(c) optionally at least one emulsifier; and

(d) optionally water;

wherein said active substance is solubilized in a solution comprising the esteramide compound of formula (I).

2. A method of solubilizing an active substance that is insoluble in water, said method comprising dissolving said active substance (a) in the esteramide compound (b) having formula (I) as defined in claim 1 .

3. A composition comprising a mixture of two or more esteramide compounds having formula (I) as defined below:

R 1 OOC-A-CONR 2 R 3   (I)

wherein:

R 1 is a radical selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36;

R 2 and R 3 are each methyl radicals; and

A is a linear divalent alkyl radical having an average number of carbon atoms ranging from 2 to 4, said radical being selected from among the radicals of the following formulae: —CH 2 —CH 2 — (ethylene), —CH 2 —CH 2 —CH 2 — (n-propylene), —CH 2 —CH 2 —CH 2 —CH 2 — (n-butylene),

excluding the following compounds: -MeOOC—CH 2 —CH 2 —CH 2 —CONMe 2 and -MeOOC—CH 2 —CH 2 —CONMe 2 .

4. The composition of claim 1 , wherein the active substance is selected from the group consisting of: Ametryne, Diuron, Linuron, Chlortoluron, Isoproturon, Nicosulphuron, Metamitron, Diazinon, Aclonifen, Atrazine, Chlorothalonil, Bromoxynil, Bromoxynil heptanoate, Bromoxynil octanoate, Mancozeb, Manebe, Zineb, Phenmedipham, Propanyl, a phenoxyphenoxy series, a heteroaryloxyphenoxy series, CMPP, MCPA, 2,4-D, Simazine, an active product of imidazolinone series, an organophosphorus family including Azinphos-ethyl, Azinphos-methyl, Alachlore, Chlorpyriphos, Diclofop-methyl, Fenoxaprop-p-ethyl, Methoxychlore, Cypermethrine, Fenoxycarbe, cymoxanil, chlorothalonyl, neonicotinoid insecticides, azaconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxyconazole, fenbuconazole, flusilazole, myclobutanyl, tebuconazole, triadimefon, triadimenol, pyraclostrobine, picostrobine, azostrobine, famoxadone, kresom-methyl, trifloxystrobine, bensulphuron-methyl, chlorimuron-ethyl, chlorsulphuron, metsulphuron-methyl, nicosulphuron, sulphomethuron-methyl, triasulphuron, tribenuron-methyl, Alachlor, Chlorpyrifos, alpha-cypermethrine, Phenmedipham, Propanil, Pendimethalin, triadimenol, Trifluralin, Oxyfluorfen, Dimethoate, Imidacloprid, Proxopur, Benomyl, Deltamethrine, Fenvalerate, Abamectin, Amicarbazone, Bifenthrin, Carbosulphan, Cyfluthrin, Difenconazole, Ethofenprox, Fenoxapropethyl, Fipronil, Fenvalerate, Fluazifop-p-butyl, Flufenouron, Hexazinone, Lambda-cyalothrin, Methomyl, Permethrin, Prochloraz, Propiconazole, and Tebuconazole.

5. A phytosanitary composition comprising at least one esteramide compound having the formula (I) below:

R 1 OOC-A-CONR 2 R 3   (I)

in which:

R 1 is a radical selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36;

R 2 and R 3 , which may be identical or different, are each radicals selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36, with the proviso that R 2 and R 3 may optionally together form a ring member that is optionally substituted and/or that optionally comprises a heteroatom; and

A is a linear divalent alkyl radical having an average number of carbon atoms ranging from 2 to 4,

wherein the esteramide compound is not C 4 H 9 —OOC—CH 2 —CH 2 —CONEt 2 ,

and wherein said at least one esteramide compound having the formula (I) solubilizes and/or coalesces other ingredients in said phytosanitary composition.

6. The composition according to claim 1 , wherein R 1 is a radical selected from among C 1 -C 12 alkyl, aryl, alkaryl and arylalkyl radicals, and the phenyl radical.

7. The composition according to claim 1 , wherein R 1 is selected from among methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, isoamyl, n-hexyl, cyclohexyl, 2-ethylbutyl, n-octyl, isooctyl, 2-ethylhexyl, and tridecyl radicals.

8. The composition according to claim 1 , wherein the esteramide compound is selected from among the following compounds:

MeOOC—CH 2 —CH 2 —CONMe 2 ; and

MeOOC—CH 2 —CH 2 —CH 2 —CONMe 2 .

9. The composition according to claim 3 , wherein R 1 is a radical selected from among C 1 -C 12 alkyl, aryl, alkaryl and arylalkyl radicals, and the phenyl radical.

10. The composition according to claim 3 , wherein R 1 is selected from among methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, isoamyl, n-hexyl, cyclohexyl, 2-ethylbutyl, n-octyl, isooctyl, 2-ethylhexyl, and tridecyl radicals.

11. The composition according to claim 3 , wherein the esteramide compound is MeOOC—CH 2 CH 2 —CH 2 —CH 2 —CONMe 2 .

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 Apr 9, 2014
From: JENTZER, OLIVIER; GUGLIERI, MASSIMO
To: RHODIA OPERATIONS
Reel/Frame 032638/0040 →