Plant protecting and regulating compositions – Antidotes – Hetero ring containing antidote
Reexamination Certificate
2000-12-20
2002-07-02
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Antidotes
Hetero ring containing antidote
C504S106000, C504S107000, C504S108000, C504S133000, C504S136000, C504S137000
Reexamination Certificate
active
06413907
ABSTRACT:
The present invention relates to a novel herbicidal synergistic composition that contains a combination of herbicides suitable for selectively controlling weeds in crops of cultivated plants, typically in crops of maize. The invention further relates to a process for controlling weeds in crops of cultivated plants and to the use of said novel composition for this purpose.
Compounds of Formula I
wherein either A
1
is nitro and A
2
is hydrogen or A
1
is methyl and A
2
is methoxy, and their salts, possess herbicidal activity, as is described for example in EP-A-0 338 992.
It has now surprisingly been shown that a combination of active compounds, in a ratio varying within specific limits, i.e. an active ingredient of formula I with one or more of the herbicides of formulae 2.1 to 2.33 listed below, which are known and are partly available commercially, exerts a synergistic effect that is able to control the majority of weeds occurring preferably in crops of cultivated plants preemergence as well as postemergence.
Accordingly, the present invention provides a novel synergistic composition for the selective control of weeds that, in addition to customary inert formulation assistants, contains as active ingredient a mixture of
a) a compound of formula I
wherein either A
1
is nitro and A
2
is hydrogen or A
1
is methyl and A
2
is methoxy, as well as their salts, and
b) a synergistically active amount of one or more compounds selected from the compound of formula 2.1
wherein
R
1
is CH
2
—OMe, ethyl or hydrogen,
R
2
is hydrogen or R
1
and R
2
together are the group —CH═CH—CH═CH—;
and the compound of formula 2.2
and the compound of formula 2.3
wherein R
6
is CH(Me)—CH
2
OMe or <S>CH(Me)—CH
2
OMe;
and the compound of formula 2.4
wherein R
7
is chlorine or SMe, R
8
is ethyl and R
9
is ethyl, isopropyl or tert.-butyl;
and the compound of formula 2.5
wherein R
10
is ethyl or n-propyl, R
11
is COO
−
1/2 Ca
++
, —CH
2
—CH(Me)S—CH
2
CH
3
or the group
and X is oxygen, N—O—CH
2
CH
3
or N—O—CH
2
CH═CH—Cl; and the compound of formula 2.6
wherein R
12
is hydrogen, methoxy or ethoxy, R
13
is Me, methoxy or fluorine, R
14
is COOMe, fluorine or chlorine, R
15
is hydrogen or Me, Y is methane or nitrogen, Z is methane or nitrogen and R
16
is fluorine or chlorine;
and the compound of formula 2.7
wherein R
17
is hydrogen or —C(O)—S-n-octyl;
and the compound of formula 2.8
wherein R
18
is bromine or iodine;
and the compound of formula 2.9
wherein R
19
is chlorine or nitro;
and the compound of formula 2.10
wherein R
20
is fluorine or chlorine and R
21
is —CH
2
—CH(Cl)—COOCH
2
CH
3
or —NH—SO
2
Me;
and the compound of formula 2.11
wherein R
22
is trifluoromethyl or chlorine;
and the compound of formula 2.12
wherein R
23
is NH
2
or <S>NH
2
;
and the compound of formula 2.13
wherein Y
1
is nitrogen, methine or N—Me, Y
2
is nitrogen, methine or C—I, Y
3
is methine, Y
4
is methine, or Y
3
and Y
4
together are sulphur or C—Cl, Y
5
is nitrogen or methine, Y
6
is methyl or methoxy and R
24
is CONMe
2
, COOMe, CH
2
—CH
2
CF
3
or SO
2
CH
2
CH
3
, or the sodium salts thereof;
and the compound of formula 2.14
and the compound of formula 2.15
and the compound of formula 2.16
and the compound of formula 2.17
and the compound of formula 2.18
and the compound of formula 2.19
and the compound of formula 2.20
and the compound of formula 2.21
and the compound of formula 2.22
and the compound of formula 2.23
and the compound of formula 2.24
and the compound of formula 2.25
and the compound of formula 2.26
and the compound of formula 2.27
and the compound of formula 2.28
and the compound of formula 2.29
and the compound of formula 2.30
and the compound of formula 2.31
and the compound of formula 2.32
and the compound of formula 2.33
In the above formulae, “Me” signifies the methyl group. The invention also embraces the salts that the compounds of formula I are able to form with amines, alkali metal bases and alkaline earth metal bases or quarternary ammonium bases. Salt-forming alkali metal and alkaline earth metal hydroxides include the hydroxides of lithium, sodium, potassium, magnesium or calcium, those of sodium or potassium being especially preferred.
Illustrative examples of amines suitable for forming ammonium salts are ammonia, as well as primary, secondary, and tertiary C
1
-C
18
alkylamines, C
1
-C
4
hydroxyalkylamines and C
2
-C
4
alkoxyalkylamines, typically methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl ethylamine, methyl isopropylamine, methyl hexylamine, methyl nonylamine, methyl pentadecylamine, methyl octadecylamine, ethyl butylamine, ethyl heptylamine, ethyl octylamine, hexyl heptylamine, hexyl octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-nbutylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and,ethoxyethylamine; heterocyclic amines such as pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines such as anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines. Preferred amines are triethylamine, isopropylamine and diisopropylamine. The compound of formula I, wherein A
1
is methyl and A
2
is methoxy, is most preferably present in the form of the diisopropylammonium salt.
It is entirely surprising that the combination of the compound of formula I with one or more herbicides selected from formulae 2.1 to 2.33 exceeds the expected additive action against the weeds to be controlled and thus in particular enhances the activity range of the individual components in two respects: On the one hand, the concentrations of the single compounds of formulae I and 2.1 to 2.33 are reduced whilst retaining good activity. On the other hand, the novel herbicidal combination also achieves a high degree of weed control where the single compounds have become no, longer agriculturally effective at low concentrations. The consequence is a substantial broadening of the activity spectrum against weeds and an additional increase in the selectivity for the cultivated plants that is necessary and desirable in the event of unintentional overapplication of herbicide. In addition, the novel composition permits greater flexibility with respect to subsequent crops while retaining the excellent control of weeds in crops of cultivated plants.
The composition of the invention may be used against a large number of agronomically important weeds, typically Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus,
Sorghum halepense
, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola, and Veronica. The composition of this invention is suitable for all methods of application commonly used in agriculture, including preemergence application, postemergence application and seed dressing. The composition of the invention is preferably suitable for weed control in crops of cultivated plants, typically cereals, rape, sugar beet, sugar cane, plantations, ri
Clardy S. Mark
Hamilton Thomas
Syngenta Crop Protection Inc.
Teoli, Jr. William A.
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