OA20264A - Encapsulation of cyclohexanediones process and product. - Google Patents

Encapsulation of cyclohexanediones process and product. Download PDF

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Publication number
OA20264A
OA20264A OA1202100209 OA20264A OA 20264 A OA20264 A OA 20264A OA 1202100209 OA1202100209 OA 1202100209 OA 20264 A OA20264 A OA 20264A
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OA
OAPI
Prior art keywords
oil
composition
cyclohexanediones
dispersion
block copolymer
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Application number
OA1202100209
Inventor
Hong ZHAN
Rachel Louise BRANAGHAN
Sarah Jane MAUDE
Original Assignee
Arysta Lifescience Inc.
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Publication of OA20264A publication Critical patent/OA20264A/en

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Abstract

Encapsulation of cyclohexanediones process and product. A composition particularly adapted for herbicidal use is described, including biopolymer micro-capsules containing one or more cyclohexanediones encapsulated therein, resulting in enhanced chemical stability and dispersibility of the encapsulated cyclohexanediones for such use. A complex coacervation method of forming such microcapsules is also described.

Description

ENCAPSULATION OF CYCLOHEXANEDIONES PROCESS AND PRODUCT
TECHNICAL FIELD
CROSS-REFERENCE TO RELATED APPLICATION
[001] This International Application claims the benefit of U.S. Provisional Application No. 62/760,565 filed November 13, 2018, the disclosure of which is expressly incorporated by reference herein in its entirety.
[002] The field of art to which this invention generally pertains is products and methods of making products which are useful in fungicidal, insecticidal and herbicidal compositions.
BACKGROUND
[003] While many Chemical products are known to be very useful as materials for herbicidal and insecticidal applications, because of their complexity, there is a constant search for ways to improve the efficiency and effectiveness of such products such as, for example, improving their stability and dispersibility.
BRIEF DESCRIPTION OF THE DRAWINGS
[004] The Figure depicts a représentative complex coacervation process for making products as described herein.
BRIEF SUMMARY
[005] A composition particularly adapted for herbicidal use is described including one or more biopolymer containing micro-capsules containing one or more cyclohexanediones encapsulated therein, resulting in enhanced Chemical stability and dispersibility of the encapsulated cyclohexanediones for such use.
[006] Additional embodiments include, the composition described above where the cyclohexanedione comprises Clethodim; the composition described above where the biopolymer comprises polysaccharide and/or cellulose; the composition described above where the polysaccharide comprises Inulin; the composition described above including one or more surfactants; the composition described above where the cyclohexanediones are présent in the micro-capsules in an amount of 1 % to 70% by weight; the composition described above made by complex coacervation; the composition described above where the composition optionally contains one or more natural gum, starch, protein, alcohol, water soluble polymer, and/or an oil; the composition described above where the alcohol comprises Sorbitol; the composition described above where the natural gum comprises Gum Arabie; the composition described above where the surfactant comprises one or more polyalkylene oxide block copolymers; a water dispersion containing the composition described above; and an oil dispersion containing the composition described above; the composition described above where the oil comprises vegetable oil; the composition described above where the oil comprises soybean oil, pine oil, and/or sunflower oil; the composition described above where the oil comprises paraffinic oil; the composition described above where the oil comprises an aromatic solvent; the composition described above where the solvent comprises C9 to Cio dialkyl and trialky benzenes (such as, for example, Aromatic 100, Aromatic 150 or Aromatic 200); the composition described above where the vegetable oil comprises rapeseed oil/or methylated rapeseed oil; the composition described above where the oil comprises a polyoxyethylene sorbitan monolaurate with a carbon chain length varying from Cio to C20 ( such as, for example, Tween® 80, or Tween® 20, or Tween® 85, or Tween® 60 (Sigma-Aldrich); the composition described above where the polyoxyethylene sorbitan is a monolaurate, monostearate, tristearate, and/or trioleate.
[007] A method of controlling insects and/or weeds comprising applying the composition described above is also described.
[008] Additional embodiments described include the method described above where the applying step is performed post-emergently after the crop breaks ground; and the method 5 described above where the applying step is performed pre-emergently before the crop breaks ground.
[009] These, and additional embodiments, will be apparent from the following descriptions.
DETAILED DESCRIPTION
[0010] The particulars shown herein are by way of example and for purposes of 10 illustrative discussion of the various embodiments of the présent invention only and are presented in the cause of providing what is believed to be the most useful and readily understood description of the principles and conceptual aspects of the invention. In this regard, no attempt is made to show details of the invention in more detail than is necessary for a fundamental understanding of the invention, the description making apparent to those skilled in 15 the art how the several forms of the invention may be embodied in practice
[0011] The présent invention will now be described by reference to more detailed embodiments. This invention may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complété, and will fully convey the scope 20 of the invention to those skilled in the art.
[0012] Unless otherwise defîned, ail technical and scientifïc terms used herein hâve the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for describing particular embodiments only and is not intended to be limiting of the invention. As used in the 25 description of the invention and the appended claims, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. Ail
publications, patent applications, patents, and other references mentioned herein are expressly incorporated by reference in their entirety.
[0013] Unless otherwise indicated, ail numbers expressing quantities of ingrédients, reaction conditions, and so forth used in the spécification and claims are to be understood as being modified in ail instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following spécification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained by the présent invention. At the very least, and not as an attempt to limit the application of the doctrine of équivalents to the scope of the claims, each numerical parameter should be construed 10 in light of the number of significant digits and ordinary rounding approaches.
[0014] Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the invention are approximations, the numerical values set forth in the spécifie examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard déviation found in their respective 15 testing measurements. Every numerical range given throughout this spécification will include every narrower numerical range that falls within such broader numerical range, as if such narrower numerical ranges were ail expressly written herein.
[0015] Additional advantages of the invention will be set forth in part in the description which follows, and in part will be obvious from the description, or may be leamed by practice of 20 the invention. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as claimed.
[0016] What is described herein is the encapsulation of cyclohexanediones to improve both their Chemical stability and dispersibility, including improving their compatibility with other 25 premix molécules and different mixtures, sustainable release, extend release profile, and longer crop protection, among others. Through the use of biopolymer encapsulation materials (such as polysaccharides and cellulose, for example - see also the tables), cyclohexanediones (such as Clethodim, for example) microcapsules are formed through conventional complex coacervation techniques. However, by carefully selecting this encapsulation technology and one or more
appropriate surfactants, the new deliveiy system demonstrates many advantages, including the following to name just a few: significant Chemical stability (e.g., for Clethodim, at least 2 weeks at 54°C as compared to currently available Clethodim products); stability of microcapsules after aging at accelerated températures in either a dry form or an oil dispersion (e.g., for Clethodim 5 products); high dispersibility of microcapsules in either aqueous phase or oil phase; controlled release of the encapsulated active ingrédient; signifïcantly high loading of active ingrédient in either a dry form or an oil dispersion with a target of a practical formulation volume for the particular application method and, the oil phase acts as a built-in adjuvant for improving bioefficacy for oil dispersions.
EXAMPLE 1
A représentative complex coacervation process with the selected appropriate surfactants is described below. See, also, the Figure. The composition materials are first hydrated and thoroughly mixed (1). The solutions are prepared by dispersing the composition materials in a 15 concentration from 2% to 50% by weight based on their molecular weights and the desired viscosity of the final solutions, i.e. balanced viscosity for product handling and minimized phase séparation. The solutions are gently stirred and stored, for example, ovemight to ensure complété hydration of the biopolymers (2). Heat may be applied to enhance dissolving if necessary. The biopolymer solution or a mixture of biopolymer solutions are mixed in a beaker with appropriate 20 surfactants (3). A Clethodim solution in a concentration from 50% to 80% is then metered into the breaker (4) and homogenized (5) for 10 minutes at 5,000 to 10,000 rpm (révolutions per minute) in a conventional mixer to generate micro-emulsions. The micro-emulsion mixture is further spray-dried (6) with an air flow whose inlet température is from 110°C to 120 °C. The microcapsule powder is collected and analyzed.
EXAMPLE 2
Altematively, the microcapsule powder can be further made into an Oil Dispersion by suspending the powder into one or more selected oils in a concentration from 20% to 90% under agitation. Optionally, one or more surfactants including dispersants, emulsifiers, rheology aids are added into the Oil Dispersion to stabilize the mixture. The oil dispersion is analyzed below.
EXAMPLE 3
Représentative encapsulation efficiency with various deliver Systems is demonstrated below. To détermine total oil content, 0.5g (grams) the encapsulated powder is mixed with 10 ml (milliliters) of water and stirred for 2 minutes. 10 ml of isopropanol and hexane (1:1 to 1:3 ratio) is added and stirred for 5 minutes. The solution is then centrifuged, filtered and placed in a water bath at 70 °C to evaporate the solvent. The final weight of the oil is recorded. To détermine surface oil content, 0.5g of encapsulated powder is mixed with hexane, centrifuged and filtered. The supematant is evaporated as above and the quantity of oil recorded. Results are given in Table 1 below.
Table 1
Sample A B C D E
Encapsulation Efficiency 95.5% 95.1% 96.1% 95.8% 96.2%
EXAMPLE 4
Chemical rétention of encapsulated Clethodim powder stored at 54 °C is compared with some commercial EC (emulsifiable concentrate) products currently on the market,
Table 2
Sample Commercial 1 (D Commercial 2 (2) F G H I J K
Day 7 87.3% 90.7% 96.0 % 99.7 % 98.5% 97.7 % >100 % >100 %
Day 14 87.2% 88.2% 92.4 % 94.3 % 94.6% 93.5 % 95.3 % 96.1 %
Notes:
(1) The commercial EC product contains 120 g/L of Clethodim (2) The commercial EC product contains 360 g/L of Clethodim
Chemical rétention of encapsulated Clethodim oil dispersions stored at 54 °C. is demonstrated in
Table 3.
Table 3
Sample L M N O
Stored for 7 Days 97.3% >100% 99.8% >100%
Stored for 14 Days 97.7% >100% >100% 98.6%
Dispersibility at 2.5% OD (oil dispersion) in dilution in ASTM 100 milliliter graduated 10 centrifuge tubes is demonstrated in Table 4.
Table 4
Sample Bloom Number of inversions* Sédimentation (ml) at time period (hours) Comments after 24 hours Number of inversions for ReDispersion (ASTM Testing Tube)
1 2 24
P Moderate 3 0 0 0 Slight creaming 1
Q Good 1 0 0 0 Slight creaming 1
*Inversion is to flip over testing tubes upside down to mix the solution to re-suspend or re-mix. The number of inversions is to evaluate the ease of re-mixing the solution. The lower the better.
i
EXAMPLE 5
Représentative emulsion-in-water compositions (before spray-drying) are shown in Tables 5 and . Représentative compositions of encapsulated powder suspended in oil to form oil dispersions are shown in Table 7.
Table 5
25 20 MG MG 1 1 1 1 1 1 1 1 1 MG
24 20 MG MG 1 1 î 1 1 1 a a VG
23 20 MG MG i 1 1 1 1 1 a a VG
22 30 MG 10 I 1 1 i ί 1 a a MG
25 VG o t— 1 t 1 | 1 J a a a a
20 20 MG VG T—1 1 1 1 1 i i 1 a a
o T—< 20 MG MG 1 1 1 1 j t 1 a
oo 20 MG o •H > 1 1 1 ; a a a MG
r- 20 MG MG 1 a 1 1 1 | a a a MG
s© i 20 i i 1 i i i 1 1 a a a
mg 20 mg 15 1 1 1 1 1 1 i a a a 1
1 i< 20 MG VG 1—i 1 1 ! i 1 1 a a a î
CG 20 MG VG V—Ί 1 1 J 1 i t a a a 2.5
CM 20 MG MG r—H i 1 1 1 « 2.5 1
1— T—— 20 MG VG i I 1 1 1 2.5 a a a a
10 o O) MG VG r—h 2.5 a i 1 i a a
CN 20 1—* CG CG cq oo 1 1 ; t
OO o Ci 6.2 5 OC MG 1 1 ; 1 a ί a a
r- 20 2.5 17. 5 1 1 ; ! a a i J
SO 20 i i VG MG H 1 1 t • «
MG 20 1 1 10 O t—i 1 1 1 «
20 1 1 VG VG ' a a a î
CG O CM MG r-H MG 1 1 ί 1 à a a
Ci 20 O T—M 10 ; â a à i à a i
t—H 20 MG MG T- • 1 t ! i «
Formulation Component Clethodim (Cyclohexanedi one) Inulin Polysaccharide Gum Arabie Natural Gum Maltodextrin Polysaccharide Waxy Maize Starch/Polysacc haride Whey Protein Xylitol Sugar Alcohol Sorbitol Sugar
1 1 1 1 1 1 } 1 t 1 1 1 1 1 1
1 1 t 1 1 1 un 1 1 1 1 1 1
1 t 1 1 1 1 1 1 1 i i 1 i V)
1 1 1 1 1 1 1 1 1 1 1 i 1 1 1 J
1 1 1 i i 1 1 1 1 1 1 1 1 1 ! 1 J 1
1 f i i 1 1 1 1 i i 1 1 1 1 1 1 1 1
1 1 1 1 1 1 1 1 i — t 1 1
1 1 1 1 1 1 1 i 1 1 « 1 1 f 1 1
1 1 1 1 f 1 1 1 i 1 1 1 t 1 ί 1 1 !
1 1 1 1 1 20 « i i 1 i
1 1 1 2.5 i i i 1 i 1 1 1
1 2.5 1 1 1 1 1 1 i 1 1 1 1 1
1 1 i i 1 t 1 1 1 1 t i 1 1
1 1 1 i 1 1 i i i 1 1 1 1
1 i t 1 1 1 1 1 i i 1 1 1 i i 1
1 1 1 1 i 1 1 1 1 1 1 i 1
» 1 ! l 1 t 1 1 i 1
1 ΐ ; t 1
1 t 1 t 1 1 ί 1 l 1 t 1 1
1 i i 1 1 1 i ! i ! i t 1
1 1 1 i ί ( 1 >
1 1 1 1 1 ! । ί 1 1 I >
1 i 1 1 ( 1 1 ! i 1 1 l i 1
1 ! । ! । 1 1 t ! ।
1 1 1 > ! । 1 1 1 1
Alcohol Mannitol Sugar Alcohol Stai'ch Polysaccharide Cyclodextrin Cyclic oligosaccharide Polyoxyethylen e (20) sorbitan monolaurate surfactant Alkylated vinylpyrrolidone polymer surfactant Isopropyl alcohol EO/PO (ethylene oxide/propylene oxide) block
I
1 1 1 1 J 1 ’ 1 50 o — o
1 1 1 1 1 1 t 1 1 1 50 o — o
j 1 1 f 1 1 1 1 50 o — o
1 1 i i 1 i J 1 50 o — o
1 1 1 1 i i 1 1 V) un o o
1 i i 1 1 1 1 1 1 1 un un o —' o
1 1 1 1 1 J 1 1 59 o — O
i 1 1 I i 1 1 1 1 09 — o
1 1 1 1 1 1 1 1 1 un un o -- o
1 1 1 1 1 1 1 1 » 1 1 1 59 o — o
1 1 i i 1 1 « un un o — o
i > i i i l 1 un un o — o
1 1 i i 1 1 1 1 1 un un c — o
« 1 1 1 1 1 1 1 un un o — o
i 1 1 1 1 1 1 1 1 un un o — o
1 ! । 1 ΐ 1 un un o o
1 1 1 ! 55 100
! i 1 55 100
ί 1 1 1 I 1 1 1 09 o o
’ 1 i i t t 1 ! । 09 o -H O
î 1 î 1 t ! t 09 o —' O
! । 1 1 1 09 o o
! i ; 1 09 o — o
î î 09 o -H O
! । I 09 o o
copolymer surfactant EO/PO block copolymer surfactant Nonionic block copolymer surfactant Butyl block copolymer surfactant Polyvinylpyrroli done Water soluble polymer Water Total
I
un 20 un un 1 1 1 1 1 i 1 1 1 un 1 1
50 20 un un 1 1 J 1 1 1 J 1 1 un 1
49 20 Un 15 1 i ï 1 1 J 1 i un 1
48 20 un 15 1 J 1 1 1 1 i 1 I un 1
47 20 un un 1 1 1 1 un i
46 20 un 15 1 ! J 1 1 1 1 i un 1
45 20 un un 1 ] i > J t f 1 1 1 1 un
44 20 un 15 i 1 1 1 « t i un
43 20 un te < 1 1 1 i 1 un «
42 20 un 1 1 > 1 1 ί . I 1 J
20 un O 1 1 O ί 1 1 1 un
40 20 un 10 J O 1 1 { 1 un !
39 20 un o i 1 10 I i 1 1 1 i î
38 20 1 O T—« 1 1 O T—-4 ! i « 1 î
37 20 un 20 1 1 O »·>—A 1 « i i 1
36 o un un 1 1 un i 1 1 1 1 1 •
35 25 1 J 10 1 1 O t 1
34 20 un un r-H 1 1 1 un !
33 20 un un T—-H 1 i t 1 • 1 ‘ 1
32 20 un un r-H 1 1 i un i
CC 20 un un i—H 1 1 1 1 | » un ί
30 20 un un T-Ή 1 i i i 1 l
29 20 un un 1 1 t I , « un
28 20 un un T—H I 1 1 | ( ! ( ί un un
27 20 un un »—1 1 i 1 ! i ! । un ί
26 20 un un —-H » l ! । ! > un !
Formulation Component Clethodim (Cyclohexanedi one) Inulin Polysaccharide Gum Arabie Natural Gum Maltodextrin Polysaccharide Waxy Maize Starch/Polysacc haride Whey Protein Xylitol Sugar Alcohol Sorbitol Sugar Alcohol Mannitol Sugar
1 1 1 i 1 1 1 i 1 1 1 1 1 1 1
1 1 1 1 1 1 1 1 1 1 i 1 1
1 i 1 1 1 1 i 1 1 1 1 1 1 1 f 1 1 1
1 1 1 i i 1 1 1 1 1 1 1 1 i 1
1 1 1 1 1 1 1 1
> 1 1 ; 1 1 1 1 i 1 1 1
! 1 1 i i 1 1 J 1 1 t ! i
i i 1 1 1 f 1 J 1 1 1 1 1 i
i 1 1 1 1 1 1 1 1 1 J 1 1 , 1 1
i t 1 1 i J 1 } 1 1 J f
1 1 t 1 1 i 1 J 1 1 1 1 1 1
1 1 1 1 1 1 1 1 1 1 1 1 J 1 1
i 1 1 1 1 l j 1 1 1 1
1 ! । 1 | 1 1 1 1 1 | î 1 i 1
1 } l 1 1 1 1 1 1 1 1 un
1 1 t 1 i 1 I 1 1 un
1 j , J i 1 i i 1 « I 10
1 1 1 1 1 1 1 1 l 1 1 in o T—1
1 ! 1 f 1 ! i 1 7.5
1 1 j 1 1 1 « 2.5
1 j j 1 1 1 1 1 1 ! ।
1 ! । 1 , t 1 1 1 ί 1
1 1 î 1 l 1 I 1
1 j t î i ! ।
1 1 1 1 1 I
l i i 1 î I ί I
Alcohol Starch Polysaccharide Cyclodextrin Cyclic oligosaccharide Polyoxyethylen e (20) sorbitan monolaurate surfactant Alkylated vinylpyrrolidone polymer surfactant Isopropyl alcohol EO/PO (ethylene oxide/propylen e oxide) block copolymer
1 1 1 i 1 1 1 1 1 1 J 1 1 »
i i 1 1 1 1 1 1 1 1 1 1
1 1 1 1 1 1 1 1 1 J 1 1 1 1 1 I
1 1 1 1 1 1 1 1 1 1 1 1
1 1 1 1 1 1
1 1 1 1 « 1 1 1 1 1 1
1 1 1 1 1 1 1 1 1 1
। 1 1 1 1 1 i i 1 1
1 1 1 t 1 1 1 i i i i 1
1 1 1 1 ! । » i i i 1 1
1 1 ! । un 1 |
! । ! । un 1 1 1 J
1 > i un 1 ! । 1 1
1 1 1 ! i J t 1 1 1 1 i i
1 1 1 « 1 1 1 1 1
ί 1 f |
i 1 i 1 f 1 i i 1 1 1
i 1 i 1 i l i ! 1 1
I 1 | ! । i 1
I l i J i
» ! । ;
î 1 1 1 1 ! ।
1 1 un i i 1 1 1 1 1 1
! t ! । ! । ί un
ί 1 ! । ί 1 ! i un 1
> ! । ! । un ί t 1
surfactant EO/PO block copolymer surfactant EO/PO block copolymer surfactant EO/PO block copolymer surfactant EO/PO block copolymer surfactant EO/PO block copolymer EO/PO block copolymer surfactant EO/PO block copolymer EO/PO block copolymer
ι
1 1 1 1 1 i 1 1 i 1 i <o 50 o — O
1 1 1 1 1 | 1 1 2.5 cm LO LO O — O
1 1 i i 1 1 1 r— 54 O — O
1 1 J 1 0.5 —M 1 1 CO LO LO O o
1 t d ir> r— 1 CO LO LO CM 100
i i 1 1 2.5 LO i i ζ- ir> o — o
l 1 1 ·—< LO i i 49 o — o
1 i i io oi ir> 1 1 LO — o
{ i t t t 2.5 1 1 LO LO o o
1 1 1 T--* 1 | 58 o — o
1 1 < 1 i 1 1 45 O — o
1 1 1 1 ! » 1 t 50 10 0
J I i 1 1 1 1 1 55 o -,
1 1 ! i ! । 1 1 09 o _
LO 1 ! t ï 1 1 40 10 0
io 1 l 1 « i i i i 50 o —1 O
O T— 1 t ! i I 55 O
O 1 1 1 1 45 O — o
7.5 ! । ! । i 1 47. 5 o —' o
2.5 J 1 1 J • } CM LO LO 10 0
LO J 50 10 0
« • • 50 o —। O
1 1 ! । i 1 50 o —' o
i 1 ! । ! । ! i 50 o — O
1 1 i 1 ! । ! । l 50 10 0
I 1 ί t • I » O LO 10 0
surfactant Polyalkylene oxide block copolymer surfactant EO/PO block copolymer surfactant Nonionic block copolymer surfactant Butyl block copolymer surfactant Polyvinylpyrrol idone Water soluble polymer Water Total
Table 6
62 20 un un 1 t 1 1 1 un 1 i
G 20 1 1 un ! 1 1 1 un 1 ;
09 20 1 un T— 1 1 j 1 1 un 1 1
59 20 1 un 1 ! t ! un 1 1 1
58 20 1 J un T—< 1 j 1 1 un 1 1 1
57 20 1 1 un »— un ; ! 1 un 1 1 i 1 1
56 20 1 un T- ! j 1 1 un 1 J
55 20 un un ! ! j I i un 1 1
54 20 un un ; ! ; 1 t un 1 »
53 20 un un > t 1 1 1 un 1 t
52 20 un un 1 < ; • i i un 1 1 ;
Formulation Component Clethodim (Cyclohexanedione) Inulin Polysaccharide Gum Arabie Natural Gum Maltodextrin Polysaccharide Waxy Maize Starch/Polysaccharide Whey Protein Xylitol Sugar Alcohol Sorbitol Sugar Alcohol Mannitol Sugar Alcohol Starch Polysaccharide
I
! ! ΐ 1 1 1 » ! i 1 1
un 1 1 1 t 1 ; ; 1 I
1 1 1 ir> 1 1 J ; 1 1 i
1 1 1 1 i ; 1 1
1 LO 1 I i 1 1 t ! ; i 1
! 1 ; 1 1 ; ; t i 1
ΐ ΐ ; ; 1 ; t t i 1 1
ί ; 1 ; 1 ; ; t 1 } 1 1
I J 1 t ! ; [ 1 1 i
! ! ; 1 1 1 1 J ; 1
! • ; I 1 1 ! 1 J « 1
Cyclodextrin Cyclic oligosaccharide Chitosan Gelatin Microcrystalline Cellulose Polyoxyethylene (20) sorbitan monolaurate surfactant Alkylated vinylpyrrolidone polymer surfactant Isopropyl alcohol EO/PO (ethylene oxide/propylene oxide) block copolymer surfactant EO/PO block copolymer surfactant EO/PO block
; 1 1 1 1 i i 1 1 -H 1 1
; t 1 1 1 1 t 1 1
1 1 1 1 1 ! 1 1
1 î 1 1 1 1 i i 1 i 1
i 1 l t 1 1 ; ΐ t 1
। 1 1 f 1 1 t < 1 ΐ l t
j 1 ! 1 1 1 i t t 1 1 ; 1
1 ! 1 ! ! 1 T—H 1——<
1 i ! i ; ! } ; 1
1 ; 1 1 > J 1 1
t î 1 I 1 ! ; 1 1
copolymer surfactant EO/PO block copolymer surfactant EO/PO block copolymer surfactant EO/PO block copolymer surfactant EO/PO block copolymer surfactant Polyalkylene oxide block copolymer surfactant EO/PO block copolymer surfactant Nonionic block copolymer surfactant Alkyl Polysaccharide Polymeric Dispersant - Croda Atlox PN100
Ο CM
1 1 1 49 100
1 1 i 50 100
; 1 1 50 100
1 1 J 1 50 100
J 1 50 100
j 1 O un 100
i J 50 100
1 i 48 100
! un 45 100
i 2.5 47.5 100
i ! T— 49 100
Butyl block copolymer surfactant Polyvinylpyrrolidone Water soluble polymer Water Total
82 14.9 3.7 11.2 3.7 1 1
H oo 14.9 3.7 11.2 3.7 1 1 1
08 14.9 3.7 11.2 3.7 i 1
79 14.9 3.7 11.2 3.7 1
78 14.9 3.7 11.2 3.7 1
14.9 3.7 11.2 3.7 i
76 14.9 3.7 11.2 3.7 l 1
75 16.4 4.1 12.3 4.1 1 1
74 15.6 3.9 11.7 3.9 1 1
P 15.2 3.8 11.4 3.8 1 1
72 9.7 2.4 7.3 2.4 1
9.7 2.4 7.3 2.4 1 1
70 9.7 2.4 7.3 2.4 1
69 9.7 2.4 7.3 2.4 J 1
oo so 1.7 o 1.3 1 f
67 1.7 ό 1.3 ! 1
99 o 2.5 7.5 2.5 j
un so O 2.5 7.5 2.5 ;
64 o T— 2.5 7.5 2.5 2.5
en so 9.1 2.3 6.8 2.3 1
Formulation Component Clethodim (Cyclohexanedione) Inulin Polysaccharide Gum Arabie Natural Gum Sorbitol Sugar Alcohol EO/PO (ethylene
I
1 î 1 i 1 1 1 1 1
1 1 1 1 1 1 1 1
1 ! > J 1 1 1 1 1 1 ! 1
1 1 1 i 1 1 1 t 1
1 i 1 1 1 1 1 1 1 1 1
1 1 ! J 1 1 1 1 1 l
1 > ! 1 i i 1 1 1 1 1
J 1 I i i 1 4.1 un un l 1
1 1 1 1 1 2.0 un un >
J ! i t 00 O un un 1 1 J
; 1 J 1 i 1 un J
j ; t ! un î ;
J i i ΐ i un ; un
1 ; 1 1 un un J
ΐ i 5.1 5.1 i i ! i
I ! 0.1 o i J ί !
i 2.5 t j ; un un !
2.5 i î ; 1 t un un j
j J j ; un un ;
! ! ; ! un un I
oxide/propylene oxide) block copolymer surfactant Polyalkylene oxide block copolymer surfactant EO/PO block copolymer surfactant Nonionic block copolymer surfactant Butyl block copolymer surfactant Polyvinylpyrrolidone Water soluble polymer Anionic polymeric dispersant Cetyl ether phosphate surfactant Oleyl ether phosphate surfactant
I
1 1 1 1.9 59 100
1 t 1 3.8 3.8 O 100
1 1 1 5.6 1.9 59 100
1 i I 1 4.5 en 59 100
1 1 1 en 1 en 09 100
1 1 m 4.5 1 59 100
1 I 1 m 4.5 en 55.5 100
l 1 I 1 1 I 1 J 1 53 100
1 1 1 1 j 53 100
1 ; î J 55 100
ΐ m ! J ! 89 100
ΜΊ I 1 1 ; ; oo Ό 100
1 i i 1 t I 68 100
1 ι 1 t t 1 1 > 1 89 100
i 1 t 1 î 98 100
ΐ t ; î ; 96 100
t ; j ! 65 100
! l ; 65 100
; ; ΐ i ; 65 100
[ j i I1 i 78 100
Polyoxyethylene (5) oleyl mono/diphosphate surfactant Polyoxyethylene (3) oleyl mono/diphosphate surfactant Sodium dioctylsulfosuccinate surfactant Polyoxyethylene (40) sorbitol hexaoleate surfactant Ethoxylated castor oil Rapeseed oil fatty acid methyl ester Total
[0017] As demonstrated by the tables above, the water based dispersions can contain functional materials such as: Cyclohexanediones such as Clethodim, Polysaccharides such as Inulin, Natural gums such as Gum Arabie, Polysaccharides such as maltodextrin, starches and polysaccharides such as Waxy Maize Starch, proteins such as Whey Protein, Sugar Alcohols such as Sorbitol and Mannitol, Polysaccharide starches, Cyclic oligosaccharide such as Cyclodextrin; conventional surfactants such as Polyoxyethylene (20) sorbitan monolaurate, Alkylated vinyl- pyrrolidone polymer, Isopropyl alcohol, EO/PO (ethylene oxide/propylene oxide) block copolymer, Anionic polymeric dispersant Polyalkylene oxide block copolymer, nonionic block copolymer, Butyl block copolymer. and Polyvinylpyrrolidone Water soluble polymer.
[0018] As also demonstrated by the tables above, the oil based dispersions can also contain functional materials such as: conventional surfactants such as EO/PO (ethylene oxide/propylene oxide) block copolymer, Polyalkylene oxide block copolymer, EO/PO block copolymer, nonionic block copolymer, Butyl block copolymer, Polyvinylpyrrolidone Water soluble polymer, anionic polymeric dispersant, cetyl ether phosphate, oleyl ether phosphate, polyoxyethylene (5) oleyl mono/di-phosphate, polyoxyethylene (3) oleyl mono/di-phosphate, sodium dioctylsulfosuccinate, polyoxyethylene (40) sorbitol hexaoleate, ethoxylated castor oil and rapeseed oil fatty acid methyl ester.
[0019] These examples are merely illustrations and are not to be understood as limiting the scope and underlying principles of the invention in any way. Various modifications of the invention in addition to those shown and described herein will become apparent to those skilled in the art form after the following examples and foregoing description. Such modifications are also intended to fall within the scope of the appended claims.
[0020] As described herein, these problems and others in this area are addressed by the invention described herein. Thus, the scope of the invention shall include ail modifications and variations that may fall within the scope of the attached claims. Other embodiments of the invention will be apparent to those skilled in the art from considération of the spécification and practice of the invention disclosed herein. It is intended that the spécification and examples be considered as exemplary only, with a true scope and spirit of the invention being indicated by the following claims.

Claims (23)

  1. What is claimed is:
    1. A composition particularly adapted for herbicidal use, comprising micro5 capsules comprising one or more biopolymers, wherein the micro-capsules encapsulateone or more cyclohexanediones, wherein the encapsulation provides enhanced Chemical stability and dispersibility of the encapsulated cyclohexanediones compared to an unencapsulated cyclohexanedione.
  2. 2. The composition of claim 1, wherein the cyclohexanedione comprises
    10 Clethodim
  3. 3. The composition of claim 1, wherein the biopolymer comprises a polysaccharide and/or a cellulose.
  4. 4. The composition of claim 3, wherein the polysaccharide comprises Inulin.
  5. 5. The composition of claim 3, including one or more surfactants.
    15
  6. 6. The composition of claim 1, wherein the cyclohexanediones are présent in the micro-capsules in an amount of 1% to 70% by weight.
  7. 7. The composition of claim 1, made by complex coacervation.
  8. 8. The composition of claim 1, wherein the composition optionally contains one or more of a natural gum, starch, a protein, an alcohol, a water soluble polymer, 20 and/or an oil.
  9. 9. The composition of claim 8, wherein the alcohol comprises sorbitol.
  10. 10. The composition of claim 8 wherein the natural gum comprises gum arabic.
  11. 11. The composition of claim 5, wherein the surfactant comprises one or more 25 polyalkylene oxide block copolymers.
    I
  12. 12. A water dispersion containing the composition of claim 1.
  13. 13. An oil dispersion containing the composition of claim 1.
  14. 14. The oil dispersion of claim 13, wherein the oil comprises a vegetable oil.
  15. 15. The oil dispersion of claim 13, wherein the oil comprises soybean oil, pine oil, and/or sunflower oil, rapeseed oil, and/or methylated rapeseed oil.
  16. 16. The oil dispersion of claim 13, wherein the oil comprises paraffinic oil.
  17. 17. The oil dispersion of claim 13, wherein the oil comprises an aromatic solvent,
  18. 18. The oil dispersion of claim 17 wherein the solvent comprises C9 to Cio dialkyl and trialky benzenes.
  19. 19. The oil dispersion of claim 13, wherein the oil comprises a polyoxyethylene sorbitan monolaurate with a carbon chain length varying from Cio to C20.
  20. 20. The oil dispersion of claim 19, wherein the polyoxyethylene sorbitan is a monolaurate, monostearate, tristearate, and/or trioleate.
  21. 21. A method of controlling insects and/or weeds in a crop comprising applying the composition of claim 1 to the crop.
  22. 22. The method of claim 17, where the applying step is performed postemergently after the crop breaks ground.
  23. 23. The method of claim 17, where the applying step is performed preemergently before the crop breaks ground.
OA1202100209 2018-11-13 2019-11-12 Encapsulation of cyclohexanediones process and product. OA20264A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US62/760,565 2018-11-13

Publications (1)

Publication Number Publication Date
OA20264A true OA20264A (en) 2022-04-14

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