Selective herbicidal composition

Details Selective herbicidal composition Selective herbicidal composition

1998-01-09

2001-08-07

Qazi, Sabiha (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S213000, C504S214000, C504S215000, C504S124000, C504S125000

Reexamination Certificate

active

06271177

ABSTRACT:

The present invention relates to a novel selective herbicidal composition for controlling grasses and weeds in crops of cultivated plants, which composition comprises a herbicide and an iron compound and protects the cultivated plants, but not the weeds, from the phytotoxic action of the herbicide, and to the use of said composition for controlling weeds in crops of cultivated plants.
When applying herbicides, the cultivated plants may also suffer severe damage owing to factors that include the concentration of the herbicide and the mode of application, the cultivated plant itself, the nature of the soil, and the climatic conditions such as exposure to light, temperature and rainfall.
To counteract this problem and similar ones, the proposal has already been made to use different compounds e.g. as antidote or safener which are able to antagonise the harmful action of the herbicide on the cultivated plant, i.e. to protect the cultivated plant while leaving the herbicidal action on the weeds to be controlled virtually unimpaired. It has, however, been found that the proposed compounds often have a very specific action, not only with respect to the cultivated plants but also to the herbicide, and in some cases also subject to the mode of application.
Surprisingly, it has now been found that a variable amount of a combination of herbicidal acetolactate synthase inhibitors (ALS inhibitors) with specific iron compounds develops an increased selectivity of the respective ALS inhibitors for the crops of cultivated plants, which combination is able to control the majority of weeds that occur preferably in crops of cultivated plants by the preemergence as well as, in particular, by the postemergence method without substantially damaging the cultivated plant.
Accordingly, the invention proposes a selective herbicidal composition comprising, in addition to customary inert formulation assistants such as carriers, solvents and wetting agents, a mixture of
a) a herbicidally effective acetolactate synthase inhibitor (ALS inhibitor) selected from the group consisting of sulfonyl ureas, sulfonamides and imidazolinones; and
b) a water-soluble iron compound.
In the compositions of this invention it is preferred to use
a) the herbicidally effective acetolactate synthase inhibitors of the sulfonyl urea group which are characterised in that they correspond to formula A
wherein
E is a group of formula
W is a group of formula
R and R
1
are each independently of the other hydrogen, methyl or methoxy;
R
2
is chloro, nitro, —CH
2
CH
2
CF
3
, —OCH
2
CH
2
OCH
3
, —OCH
2
CH
2
Cl, —COO—C
1
alkyl,
—COO—C
2
alkyl or
R
3
is —COO—C
1
alkyl or —COO—C
2
alkyl;
R
4
is —COOCH
3
, —CF
3
, —OCHF
2
, —OCH
2
CF
3
, —OCH
2
CHCIF, —CON(CH
3
)
2
or —SO
2
C
2
H
5
;
R
04
is hydrogen or —CF
3
;
R
5
is —COO—C
1
alkyl or —COO—C
2
alkyl or the group of formula
R
6
is hydrogen or chloro;
R
7
is methyl or the group of formula
R
8
is chloro or —SO
2
C
2
H
5
;
X
1
is chloro, methyl, methoxy or —OCHF
2
;
Y
1
is methyl, methoxy or —OCHF
2
;
X
2
is methyl, methoxy, ethoxy, —CF
3
or —N(CH
3
)
2
; and
Y
2
is —CF
3
, methoxy, —OCH
2
CF
3
or —NHCH
3
, and the salts of those compounds;
those herbicidally effective acetolactate synthase inhibitors of the sulfonamide group which are characterised in that they correspond to formula C
wherein
R
10
is fluoro or chloro;
R
11
is fluoro, chloro or a —COOCH
3
group;
R
12
is hydrogen or methyl;
R
13
is hydrogen or fluoro;
R
14
is hydrogen or methoxy;
V is nitrogen or a C—OC
2
H
5
group; and
Q is nitrogen or a C—CH
3
or C—OCH
3
group; or
to formula C
1
wherein
R
22
is C
1
-C
10
alkyl, C
1
-C
10
alkyl which is substituted by halogen, C
3
-C
8
cycloalkyl, cyano or oxiranyl, C
2
-C
8
alkenyl, C
2
-C
8
haloalkenyl or amino; and
those herbicidally effective acetolactate synthase inhibitors of the imidazolinone group which are characterised in that they correspond to formula D
wherein
R
20
is hydrogen, methyl, ethyl or a —CH
2
—OCH
3
group;
R
21
is hydrogen; or
R
20
and R
21
, taken together, form a —CH═CH—CH═CH— group; and
b) water-soluble iron compounds which are characterised in that they correspond to formula B
[Fe
II,III
-Z]  (B),
wherein
Fe
II,III
is the element iron having the oxidation number +2 (II) or +3 (III); and
Z is a mono- or polyvalent anion of inorganic or organic acids H-Z.
Compounds of formula A which are preferably used in the composition of this invention are those, wherein E is a group of formula
W is a group of formula
R and R
1
are each independently of the other hydrogen or methyl;
R
2
is chloro, nitro, —CH
2
CH
2
CF
3
, —OCH
2
CH
2
OCH
3
, —OCH
2
CH
2
Cl, —COO—C
1
alkyl, —COO—C
2
alkyl or
R
3
is —COO—C
1
alkyl or —COO—C
2
alkyl;
R
4
is —CF
3
, —OCHF
2
, —OCH
2
CF
3
, —OCH
2
CHCIF, —CON(CH
3
)
2
or —SO
2
C
2
H
5
;
R
5
is —COO—C
1
alkyl or —COO—C
2
alkyl or the group of formula
R
6
is hydrogen or chloro;
R
7
is methyl or the group of formula
X
1
is chloro, methyl, methoxy or —OCHF
2
;
Y
1
is methyl, methoxy or —OCHF
2
;
X
2
is methyl, methoxy, ethoxy or —N(CH
3
)
2
; and
Y
2
is —CF
3
, methoxy, —OCH
2
CF
3
or —NHCH
3
, and the salts of those compounds.
The sulfonyl urea compounds of formula A used according to this invention are known, inter alia, from “The Pesticide Manual”, Tenth Edition, 1994, Editor C. Tomlin, pages 34, 85, 180, 211, 701, 734, 829, 865, 904, 931, 976, 1005 and 1010; EP-A-0 084 020, EP-A-0 318 602 and EP-A-0 388 873, and some are commercially available (see Tables 1 and 2).
The invention also includes the salts that the compounds of formula A can form with in principle any bases that are capable of abstracting an acid hydrogen atom, e.g. in the —SO
2
—NH—CO— grouping. Amines, hydrides, hydroxides, alcoholates, hydrogen carbonates and carbonates of alkali metal and alkaline earth metals, especially of sodium, potassium, magnesium and calcium, have proved especially advantageous in that connection.
The sulfonamides of formula C and C
1
used according to this invention and their preparation are known, inter alia, from “The Pesticide Manual”, Tenth Edition, 1994, Editor C. Tomlin, pages 486 and 696, and from EP-A-0 592 680, and some are commercially available (see Tables 5 and 6).
The imidazolinones of formula D and their preparation are known, inter alia, from “The Pesticide Manual”, Tenth Edition, 1994, Editor C. Tomlin, pages 584, 586 and 587, and some are commercially available (see Table 7).
The water-soluble iron compounds of formula B are iron salts or iron chelates, wherein the iron may have the oxidation number +2 (II: divalent iron) or +3 (III: trivalent iron). The appertaining anions Z can carry one or more than one negative charge. They can be formed from the corresponding inorganic or organic acids H-Z by abstracting the acid hydrogen atom. Suitable are, for example, mineral acids, such as hydrochloric acid, sulfuric acid or nitric acid, organic acids, preferably polyacids, such as (HOOC—CH
2
—)
2
and
and, particularly preferably, organic acids, the iron chelates (Fe
II,III
-Z) of which are distinguished by high stability even at basic pH (pH values>7), typically ethylenediamine tetracetic acid (HOOC—CH
2
)
2
NCH
2
CH
2
N(CH
2
—COOH)
2
(ETA), N,N′-ethylenebis[2-(2-hydroxyphenyl)glycine]
(EDDHA), diethylenetriaminepentacetic acid (HOOC—CH
2
)
2
NCH
2
CH
2
N(CH
2
—COOH)CH
2
CH
2
N(CH
2
—COOH)
2
(DTPA) and N-(2-hydroxyethyl)ethylenediaminetriacetic acid HO—CH
2
CH
2
N(CH
2
—COOH)CH
2
CH
2
N(CH
2
—COOH)
2
(HEDTA).
The iron chelates of formula B are obtained from iron salts and mono- or polyvalent acids HZ, such as are also used in the preparation of commercial iron chelates. The preparation of such iron chelates and their use as micronutrients in agriculture is disclosed, inter alia, in US-A-2 921 847.
Commercial forms of the above-mentioned iron chelates (Fe
II,III
-Z) react according to the nature of Z acidically in aqueous solutions or emulsions, e.g. in accordance with [Fe
II,III
-Z(—COOH)
m
], or neutrally, e.g. i

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