(Poly)ethereal ammonium salts of herbicides bearing acidic...

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Reexamination Certificate

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C514S114000, C562S553000

Reexamination Certificate

active

06300323

ABSTRACT:

BACKGROUND OF THE INVENTION
Some herbicides bearing acidic moieties are known to be highly effective and commercially important herbicides useful for combating the presence of a wide variety of unwanted vegetation, including agricultural weeds.
Since usually, such acidic herbicides have low solubility in water, they are applied as their derivatives such as metal salts or ammonium salts to enhance the solubility, or esters or amides to enhance movement into plant. For example, N-phosphonomethyl-glycine is formulated in commercial compositions in the form of a water-soluble salt. Herbicidal amine salts of N-phosphonomethylglycine are disclosed, for example, in U.S. Pat. Nos. 3,799,758, 3,853,530, 4,140,513, 4,315,765, 4,405,531, 4,481,026, and 4,507,250. These salts are claimed to have uses as plant regulators, herbicides and defoliants. Many of these salts have the counter-cation to N-phosphonomethylglycine anion bearing relatively low molecular weight. Typical of such salts are alkali metal, for example sodium and potassium salts; ammonium salt; and numerous salts having an ammonium, sulfonium or sulfoxonium cation with 1-3 organic groups containing in total 1-6 carbon atoms, for example 2-propylammonium (isopropylammonium), ethanolammonium, ethylenediammonium, trimethylsulfonium or trimethylsulfoxonium.
Recent Patent WO 99/05914 reveals the herbicidal compositions promoting herbicidal effectiveness of exogeneous chemical substances. The compositions are the amphiphilic salts having anions of the parent exogeneous chemical substances and cations derived by protonation of one or more polyamine(s) or polyamine derivative(s) each having (a) at least two nitrogen-containing groups, of which a number n not less than 1 are amino groups that can be protonated to form cationic primary, secondary, or tertiary ammonium groups, and (b) at least one hydrocarbyl or acyl group having about 6 to 30 carbon atoms.
BRIEF DESCRIPTION OF THE INVENTION
A preferred group of the acidic herbicide consists of those that are normally applied post-emergence to foliage of plants. An especially preferred group of foliar-applied herbicide consists of those that are systemic in plants, that is, translocated to some extent from their point of entry in the foliage to other parts of the plant where they can usefully exert their herbicidal effect.
This invention relates to the enhancement of the activity of acidic herbicides by the formation of salts using (poly)ethereal amine compounds and also to a method of controlling undesirable vegetation by applying a herbicidally effective amount of the (poly)ethereal amine salts to such vegetation when the latter is in a post-emergent state. These (poly)ethereal ammonium salts are thought to aid the penetration and transport of acidic herbicides into and throughout the plant. These salts contain anions derived from parent herbicides and amphiphilic (poly)ethereal ammonium cation(s). These features are proved to enhance the activity of acidic herbicides.
The term “herbicidally effective amount” designates any amount of the compounds disclosed herein, which will kill a plant or any portion thereof. By “plants” is meant germinating seeds, emerging seedlings, and established vegetation, including roots and above ground-portions.
By the term “post-emergent” as used herein, is meant the application of the herbicide compound to weed pests, after these pests have emerged from the ground.
The present invention provides a (poly)ethereal ammonium salt of acidic herbicides of the following formula I:
Wherein x, y, and z are integers from 0 to 3 with the proviso that 0<x+y+z≦3.
Acidic Herbicide-X, Acidic Herbicide-Y, and Acidic Herbicide-Z, same or different that can be used in compositions of the present invention and possess the dissociable proton(s) in their structures include, but are not limited to, the following herbicides.
acifluorfen, asulam, benazolin, bentazon, bilanafos, bromacil, bromoxynil, chloramben, clopyralid, cyhalofop, 2,4-D, 2,4-DB, dalapon, dicamba, dichlorprop, diclofop, DNOC, endothall, fenac, fenoxaprop, flamprop, fluazifop, flumiclorac, fluoroglycofen, fomesafen, fosamine, glufosinate, glyphosate, haloxyfop, imazameth, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, ioxynil, MCPA, MCPB, MCPP, mecoprop, methylarsonic acid, naptalam, nonanoic acid, picloram, quinclorac, quizalofop, sulfamic acid, 2,3,6-TBA, TCA, and triclopyr.
The (poly)ethereal amine(s) II or derivative(s) thereof are preferably selected from compounds of formula II
1
through II
5
:
wherein R
1
is a hydrogen, a C
1-26
alkyl, a C
2-6
alkenyl, a C
2-6
alkynyl branched-chain or straight-chain which may or may not be substituted with one or more halogen, hydroxy, C
1-6
alkoxy, (C
1-6
alkyl-)
q
-amino (
q
is an integer of 0, 1, or 2), morpholino, or C
1-6
alkoxycarbonyl group, an aryl, or a heteroaryl which may or may not be substituted with C
1-6
alkyl, C
1-6
haloalkyl, halogen, C
1-6
alkoxy, (C
1-6
alkyl-)
q
-amino (
q
is an integer of 0, 1, or 2), nitro, or C
1-6
alkoxycarbonyl group;
R
2
, R
5
, and R
6
are independently C
1-8
alkylene branched-chain or straight-chain, which may contain imine or ether linkage therein and may be substituted by a C
1-6
alkyl group.
R
3
and R
4
are a hydrogen atom or a C
1-6
alkyl group, which may be branched or straight and may or may not be substituted with one or more C
1-6
alkoxy, or a group Of R
1
—(—O—R
2
—)
m′
—O—.
R
7
is a hydrogen or a C
1-6
alkyl group.
l, m and n is a number from 1 to about 500.
m′ is a number from 0 to about 35.
p is an integer of 0 or 1.
When m is 1, none of R
1
, R
3
, and R
4
is H and furter R
2
is not ethylene.
Many of these (poly)ethereal amine exist as steric or enantiomeric isomers and this invention covers all forms and mixtures of the aforementioned compounds. Most of the (poly)ethereal amines and their derivatives are commercially available. New (poly)ethereal amines II
6
bearing (hetero)aryl moiety were synthesized by the following reaction between (hetero)aryl halide and hydroxyl-amine.
The examples of the (poly)ethereal amines II include, but are not limited to, the following (poly)ethereal amines in Tables-1 through -5.
TABLE 1
(poly)ethereal amines II
1


No.
R
1
R
2
m
R
3
R
4
1-1
H
1

1-2
H
2
H
H

1-3
H
1
H
H

1-4
H
1

1-5
H
1
H
H

1-6
H
10
H
H

1-7
H
3
C—
16.34
H
H

1-8
H
3
C—
44.75
H
H

1-9
1
H
H

1-10
1
H

1-11
3
H

1-12
1
H
H

1-13
1
H
H

1-14
5
H
H

1-15
1
H
H

1-16
(n)-C
12
H
25

2
H
H

1-17
(n)-C
12
H
25

1
H
H

1-18
(n)-C
12
H
25

35 H
H

1-19
15
—CH
3
—CH
3

1-20
2
H
H

1-21
1
H
H

1-22
26
H
H

1-23
33.1
H
H

1-24
2.6
H
H

1-25
5.6
H
H

1-26
1
H
H

1-27
2

1-28
1
H
H

1-29
1

1-30
1
H
H

1-31
1
H
H

1-32
6
H
H

1-33
10
H
H

1-34
6
H
H

1-35
2
H
H

1-36
1

1-37
1
H
H

1-38
1

1-39
1
H
H

1-40
1
H
H

1-41
1

1-42
2

1-43
3

1-44
-(n)-C
6
H
13
-(n)-C
6
H
13

1-45
-(n)-C
6
H
13
-(n)-C
6
H
13

1-46
H
3
C—
112.93
H
H

1-47
H
3
C—
226.56
H
H

1-48
H
3
C—
453.84
H
H
TABLE 2
(poly)ethereal amines II
2


No.
R
1
R
2
R
3
R
4
R
5
m
2-1
H
3
C—
H
H
9

2-2
H
3
C—
H
H
19.85

2-3
H
H
34.17

2-4
H
3
C—
H
H
5

2-5
H
3
C—
25

2-6
H
3
C—
H
H
45

2-7
H
H
15

2-8
35

2-9
H
H
55

2-10
H
3
C—
H
H
63.3

2-11
(n)-C
12
H
25

35

2-12
—CH
3
—CH
3
5
TABLE 3
(poly)ethereal amines II
3


No.
R
1
R
2
R
3
R
4
R
5
R
6
m
3-1
H
H
1

3-2
H
3
C—
H
H
8

3-3
H
3
C—
H
H
8

3-4
H
3
C—
H
H
15

3-5
H
3
C—
H
H
35

3-6
H
3
C—
—CH
3
—CH
3
55

3-7
H
H
20

3-8
—CH
3
—CH
3
15
TABLE 4
(poly)ethereal amines II
4


No.
R
1
R
2
R
3
R
4
R
5
R
6
l
n
m
4-1
H
H
l + n = 3.6
9
4-2
—CH
3
—CH
3
5
5
5

4-3
H
H
2
4
6

4-4
3
5
7
TABLE 5
(poly)ethereal amines II
5


No.
R
2
R
3
R
4
R
7
l
m
n
p
5-1
H
H
C
2
H
5

l + m + n = 5.2
1

5-2
H
H
H
l + m + n = 50
0

5-3
—CH
3
—CH
3
(n)-C
6
H
13

l + m + n = 10
1

5-4
H
3
C—
l + m + n = 80
0
These (poly)ethereal amines will react with one or more molar equivalent of acidic herbicide(s). The ge

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