Agrochemical composition

Details Agrochemical composition Agrochemical composition

2002-01-29

2004-06-15

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S237000, C504S250000, C504S337000, C504S365000

Reexamination Certificate

active

06750178

ABSTRACT:

This invention relates to an agrochemical composition and in particular to an agrochemical composition containing an activity-enhancing adjuvant.
An agrochemical is generally used with an adjuvant or combination of adjuvants to provide optimum biological activity. Much has been published on the selection of adjuvants to achieve particular effects with individual agrochemicals and classes of agrochemical. In general it has been assumed that activity-enhancement results from surfactant properties of the adjuvant and most such activity-enhancing adjuvants are surfactants in that they contain within the molecule both a hydrophobic portion and a-lypophobic-portion. We have now found that a class of alkoxylated amines provides excellent activity enhancement when used in an agrochemical formulation. Surprisingly certain members of the class have either no surfactant properties or low surfactant properties. Furthermore, unlike many surfactants used as conventional agrochemical adjuvants, the alkoxylated amines of the present invention generally exhibit an exceptionally low toxicological profile and in particular excellent ecotoxicological characteristics and provide compositions which are especially benign to the environment. It is exceptional to find adjuvants which combine a high level of activity enhancement with low toxicity.
According to the present invention there is provided an agrochemical composition comprising an agrochemical active ingredient and an adjuvant of formula (I) and salts thereof
X—(R
3
O)
a
—R
4
—NR
2
R
1
  (I)
wherein R
1
and R
2
are independently hydrogen or a lower alkyl group or a group X′—(R
3′
O)
a′
—R
4′
— wherein R
3′
and R
4′
respectively may take any of the values of R
3
and R
4
as hereinafter defined and wherein X′ is —OH or a lower alkoxy group containing from 1 to 6 carbon atoms and a′ is from 0 to 400
R
3
O is an ethoxy, propoxy or butoxy group or a random or block mixture thereof,
R
4
is a linear or branched chain alkylene bridging group containing from 1 to 4 carbon atoms, X is
(IA) —OH or a lower alkoxy group containing from 1 to 6 carbon atoms
or X is
(IB) a group R
5
R
6
N— or R
5
R
6
N—R
7
—
wherein R
5
and R
6
are independently hydrogen or a lower alkyl group or a group X′—(R
3′
O)
a′
—R
4′
— as hereinbefore defined wherein X′ is —OH or a lower alkoxy group containing from 1 to 6 carbon atoms,
and R
7
is a linear or branched chain alkylene bridging group containing from 1 to 4 carbon atoms
or X is
(IC) a group
wherein R
10
, R
11
, R
14
and R
15
are independently hydrogen or a lower alkyl group or a group X′—(R
3′
O)
a′
—R
4′
— as hereinbefore defined wherein X′ is —OH or a lower alkoxy group containing from 1 to 6 carbon atoms;
and R
8
and R
12
, are independently alkyl groups containing from 1 to 4 carbon atoms and R
9
and R
13
and R
21
are independently a linear or branched chain alkylene bridging group containing from 1to 6 carbon atoms, R
16
, R
17
, R
18
, R
19
and R
20
are independently hydrogen or a lower alkyl group and d is 0 or 1
and wherein a, is from 1 to 400 or if X is of formula IC, the sum of a, b and c is from 3 to 400.
A considerable number of salts of the compound of formula (I) suitable for use in agrochemical applications will occur to one skilled in the art. Examples of salts include phosphate, sulphate, carboxylate, acetate, formate and chloride although many other suitable salts will occur to one skilled in the art. Alternatively the compound of formula (I) may form a salt with an acidic agrochemical such as glyphosate. Salts of the compound of formula (I) can also be prepared from acidic surfactants, for example optionally ethoxylated alkyl or alkylene ester derivatives of phosphoric acid or phosphonic acid, or optionally ethoxylated alkyl or alkylene carboxylic acids or sulphonic acids. It will be appreciated that where more than one amine functionality is present in the compound of formula (I) or the relevant acid has more than one functional group, the option for different salt stoichiometries and mixed salts exists and all such variations are included herein.
As used herein, the term lower alkyl means a linear or branched chain primary or secondary alkyl group containing from 1 to 6 carbon atoms. Preferred lower alkyl groups contain from 1 to 4 carbon atoms, and methyl, ethyl and propyl or isopropyl groups are especially preferred.
R
1
, R
2
, R
5
, R
6
, R
10
, R
11
, R
14
and R
15
are preferably methyl or hydrogen. Hydrogen is especially preferred.
Thus it is preferred that in a compound of formula (I):—
X is —OH or a lower alkoxy group containing from 1 to 4 carbon atoms or
X is R
5
R
6
N— wherein R5 and R6 are hydrogen or a lower alkyl group containing from 1 to 4 carbon atoms or
X is a group of formula IC′
wherein R
8
O and R
12
O are independently ethoxy, or propoxy, in particular isopropoxy, or a random or block mixture thereof, R
9
and R
13
are independently a linear or branched chain alkylene bridging group containing 2 or 3 carbon atoms and R
21
is a linear or branched chain alkylene bridging group containing from 1 to 3 carbon atoms, R
18
is hydrogen or lower alkyl containing from 1 to 4 carbon atoms and d is 0 or 1,
R
1
and R
2
are independently hydrogen or a lower alkyl group containing from 1 to 4 carbon atoms, R
3
O is ethoxy, or propoxy, in particular isopropoxy, or a random or block mixture thereof, R
4
is a linear or branched chain alkylene bridging group containing 2 or 3 carbon atoms and a is from 1 to 400 or if X is of formula IC′, the sum of a, b and c is from 3 to 400.
The compounds for use in the composition of the present invention are alkoxylated monoamines (X is of Formula IA), diamines (X is of Formula IB) or triamines (X is of Formula IC). Alkoxylation typically takes place to introduce ethoxy groups or propoxy groups, although butoxy groups may sometimes also be used. The propoxy group is preferably an isopropoxy group, —OCH
2
—CH(CH
3
)—. Mixed alkoxylation may also take place to introduce for example both ethoxy and propoxy or butoxy groups which may be present as a mixture in either random or block arrangement. Thus each of —(OR
3
)
a
—, —(OR
8
)
b
— and —(OR
12
)
c
)— in the above formulae independently represent alkoxy groups, for example ethoxy and propoxy groups or a mixture thereof. Thus the definition of group —(OR
3
)
a
for example includes a group
—(OC
2
H
4
—)
x
—(OCH
2
—CH(CH
3
)—)
y
wherein a is represented by the sum of x and y. Other combinations of for example ethoxy propoxy and butyoxy groups in any desired order are similarly included in the definition of —(OR
3
)
a
—, —(OR
8
)
b
— and —(OR
12
)
c
— respectively.
The process of alkoxylation may produce a mixture of products having different degrees of alkoxylation. Thus the values of a, b, c and a′ represent an average degree of alkoxylation over the product as a whole. Preferred values of a, b, and c, respectively are from 1 to 100, for example from 1 to 50 and especially from 1 to 30 . Thus when X in formula (I) is of formula IC, the sum of a+b+c is preferably from 3 to 90. In the group X′—(R
3′
O)
a′
—R
4′
— if present, a′ is preferably from 0 to 50 and especially from 0 to 30.
An especially preferred alkoxylated monoamine (wherein X is of formula IA) for use in the present invention has the formula II wherein X is methoxy, —(R
3
O—)
a
represents a mixture of ethoxy and propoxy groups R
4
represents a propylene bridging group.
CH
3
—O—(—CH
2
CH
2
O—)
x
—(—CH
2
—CH(CH
3
)—O—)
y
—CH
2
—CH(CH
3
)—NH
2
  (II)
The average degree of ethoxylation (x) may vary from 0 to about 45 or more preferably from 0 to about 40, for example from 0 to about 20 and the average degree of propoxylation (y) may vary from 0 to about 90 and more preferably from about 1 to about 35, for example from about 2 to about 30, provided that x and y are not both 0 at the same time. Products are commercially available wherein x is abo

Affiliated with

Also associated with

Rating

Agrochemical composition does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Agrochemical composition, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Agrochemical composition will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3294736