Organosiloxane containing modified groups in agricultural...

Details Organosiloxane containing modified groups in agricultural... Organosiloxane containing modified groups in agricultural...

2001-05-18

2003-03-18

Dawson, Robert (Department: 1712)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Biocides; animal or insect repellents or attractants

C556S444000, C556S445000, C568S673000, C528S031000, C528S028000, C528S027000, C528S025000, C525S474000, C525S477000, C524S287000, C524S588000, C524S189000, C524S190000, C524S211000, C504S116100

Reexamination Certificate

active

06534077

ABSTRACT:

BACKGROUND OF THE INVENTION
Many herbicides require the addition of an adjuvant to the spray mixture to provide wetting and spreading on foliar surfaces. Often that adjuvant is a surfactant, which can perform a variety of functions, such as increasing spray droplet retention on difficult to wet leaf surfaces, or to provide penetration of the herbicide into the plant cuticle. These adjuvants are provided either as a tankside additive or used as a component in herbicide formulations.
Gaskin, et al.,
Pestic. Sci.
1993, 38, 185-192, demonstrated that some trisiloxane ethoxylates (TSE), such as Silwet L-77® surfactant (available from Witco Corp. of Greenwich, Conn.), can antagonize cuticular penetration of a herbicide into grasses, when compared to the herbicide alone. The term antagonism is used to indicate that the treatment of herbicide plus adjuvant is less effective than the comparative herbicide treatment.
Sandbrink, et al., (Pest. Sci. 1993, 38, 272-273, published that a TSE antagonized glyphosate performance relative to glyphosate alone in the control of
Panicum maximum
Jacq. Snow, et al., Langmuir, 1993, 9, 424-30, discusses the physical properties and synthesis of novel cationic siloxane surfactants. These siloxanes are based on the reaction of chloro propyl modified trisiloxane with an alkanolamine, such as N-methylethanolamine, which was further reacted with a halide to make a quaternary surfactant.
Petroff, et al., EP 92116658, describes the use of cationic, quaternary trisiloxanes to enhance the efficacy of glyphosate on velvetleaf, a broadleaf weed. Henning, et al., (DE 4318537) describes cationic siloxanyl modified polyhydroxy hydrocarbon or carbohydrate for use with plant protection agents. These compounds are derived from a saccharide containing 1 to 10 pentose and/or hexose units, modified with a quaternary ammonium group, and a siloxane moiety.
Reid, et al., U.S. Pat. No. 3,389,160 describes amino modified siloxane alkoxylates where the amino functionality appears as the terminal group on the alkyleneoxide moiety, opposite the siloxane group.
Policello in U.S. Pat. No. 5,998,331 discloses amino modified siloxanes wherein the amine is bound by an ether bond to the siloxane backbone wherein the amine may be terminal or pendant to the backbone.
SUMMARY OF THE INVENTION
It has now been discovered that an organosiloxane copolymer containing separate terminal or pendant amino-containing and polyether-containing functional groups are useful as adjuvants and additives for applications with herbicides.
Optionally, the modified organosiloxanes of this invention may be blended with conventional trisiloxane alkoxylates (TSAs). Blends of these modified organosiloxanes with TSAs provide enhanced wetting properties on difficult to wet plant surfaces.
Additionally the modified organosiloxanes of this invention may be blended with conventional organic surfactants, as emulsifiers, dispersants, coadjuvants or cosurfactants.
DETAILED DESCRIPTION OF THE INVENTION
The modified organosiloxanes are useful as adjuvants for herbicide applications.
Modified Organosiloxanes:
The modified organosiloxanes of the present invention preferably are amino polyether siloxanes and have the average general formula:
[O
½
Me
2
SiO
½
]
d
[O
½
MeSi(Z)O
½
]
e
[O
½
SiMe(Q)O
½
]
f
[O
½
SiMe
2
P]
g
where d is 0 to 2; e is >0 and <4, preferably >0 to 2; f≧0 and <4, most preferably >0 to 2; g is 2 if the siloxane is not cyclic or zero if the siloxane is cyclic; d+e+f+g≦6; Z=C
n
H
2n
O(C
a
H
2a
O)
w
R
1
; n=2 to 4, preferably 3; a=2-4, preferably 2; w=1 to 30; R
1
is hydrogen, or a hydrocarbon radical between 1 and 4 carbon atoms; Q=B(O)
j
R
2
N(R
3
)
2
; B is a divalent bridging group of C
1
to C
6
, preferably C
3
to C
4
; R
2
is a divalent organic group containing 2 to 8 carbons, preferably 3 to 4 carbons, each optionally OH substituted; j is 0 or 1, preferably 1; R
3
is hydrogen, an amino alkyl of one to four carbons, an alkyl of 2 to 4 carbon atoms, an alkyl of 2 to 4 carbon atoms substituted with one or more hydroxy groups or a polyether of the general structure —(C
a
H
2a
O)
b
R
4
; each a is 2 to 4, preferably 2 to 3; each b is 2 to 30, preferably 2 to 8; the R
4
groups independently are hydrogen or a group of 1 to 4 carbons; and P is Q or, provided f is not 0, methyl.
Preferably a is such that there is a mixture of ethylene oxide (EO), propylene oxide (PO) units and butylene oxide (BuO) units, where a=2 and 4. Preferably, for aqueous applications, there is a preponderance of EO units, most preferably every a=2. For non-aqueous applications, such as crop oil concentrates, there may be more PO and BuO units. When Z or R
3
contain a mixture of oxyalkylenes, the different oxyalkylene groups may be arranged in blocked or random manner. One skilled in the art will understand the advantages in the position of the oxyethylene relative to the oxypropylene, when the alkyleneoxide group is blocked.
The Q groups may include protonated amines, i.e., where there is a hydrogen atom attached to the nitrogen in the Q group, which can occur to the aminosilicon alkoxylates under acidic conditions. Also contemplated herein are quaternary versions of Q, i.e., where there is a third R
3
group on the nitrogen in Q. Quaternarization may be accomplished in conventional manner. In either such case, i.e., protonated or quaternarized Q, the group Q may be represented by the formula:
B(O)
j
R
2
N
+
(R
3
)
3
.
OTHER SOLIXANES
In addition, the compositions of the present invention optionally may include TSAs of the general formula:
R
5
Me
2
SiO[MeSi(G)O]
x
SiMe
2
R
5
Wherein x=0 to 2, preferably 1; G=C
n
H
2n
O(C
2
H
4
O)
t
(C
3
H
6
O)
w
R
6
; n=2 to 4, preferably 3; t=3 to 20, preferably 4 to 8; w=0 to 8, providing that when w is >0, (t+w) is preferably between 5 and 12; R
6
is hydrogen, acetyl or a hydrocarbon radical between 1 and 4 carbon atoms; and R
5
is G, or an alkyl of one to four carbons. The preferred nonionic siloxane alkyoxylates are trisiloxane alkoxylates, where x=1, n=3, t=4 to 8, w=0, R
5
is Me, R
6
is H or Me.
PESTICIDES
The compositions of the present invention also optionally include pesticides, especially acid functionalized ones, i.e., compounds that contain at least one carboxylic, sulfonic or phosphonic acid group or their salt or ester. The term pesticide means any compound used to destroy pests, e.g., rodenticides, fungicides, and herbicides. Illustrative examples of pesticides which can be employed include, but are not limited to, growth regulators, photosynthesis inhibitors, pigment inhibitors, mitotic disrupters, lipid biosynthesis inhibitors, cell wall inhibitors, and cell membrane disrupters. The amount of pesticide employed in compositions of the invention varies with the type of pesticide employed. More specific examples of pesticide compounds that can be used with the compositions of the invention are: phenoxy acetic acids, phenoxy propionic acids, phenoxy butyric acids, benzoic acids, triazines and s-triazines, substituted ureas, uracils, bentazon, desmedipham, methazole, phenmedipham, pyridate, amitrole, clomazone, fluridone, norflurazone, dinitroanilines, isopropalin, oryzalin, pendimethalin, prodiamine, trifluralin, glyphosate, sulfonylureas, imidazolinones, clethodim, diclofop-methyl, fenoxaprop-ethyl, fluazifop-p-butyl, haloxyfop-methyl, quizalofop, sethoxydim, dichlobenil, isoxaben, and bipyridylium compounds.
EXCIPIENTS
The compositions also may include fatty acid esthers, e.g., methyl soyate, for crop oil concentrate formulations, as well as water, for aqueous applications. Buffers, preservatives and other standard excipients known in the art also may be included in the composition. When the compositions of the present invention are insoluble in distilled water, spreading may be achieved by the addition of a small am

Affiliated with

Also associated with

Rating

Organosiloxane containing modified groups in agricultural... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Organosiloxane containing modified groups in agricultural..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Organosiloxane containing modified groups in agricultural... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3018781