Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1980-09-06
1982-06-22
Jiles, Henry R.
Chemistry: fertilizers
Processes and products
Forms or conditioning
548375, 548376, 548378, 548255, 548262, 548264, 548265, 548337, 548341, A01N 4350, A01N 4356, A01N 4364, C07D23112, C07D23361, C07D24904, C07D24908
Patent
active
043360610
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The invention is used for combating unwanted plants.
Characteristics of prior art technical solutions
Haloacetanilides which have herbicidal or growth-regulating properties have been disclosed. The compound 2-chloro-2',6'-diethyl-N-methoxymethylacetanilide (U.S. Pat. No. 3,547,620) has achieved considerable economic importance. A further active ingredient which has been disclosed is 2-chloro-2'-ethyl-6'-methyl-N- (1'-methoxyprop-2'-yl)-acetanilide (German Published Application DE-AS No. 2,328,340). This compound exhibits, in addition to a good action on unwanted grasses, good persistence in the soil.
Object of the invention
The object of the invention is to develop herbicidal agents having increased activity.
Description of the essence of the invention
The invention is based on the desire to provide a new herbicidal agent.
It has been found that a herbicide containing an acetanilide of the formula ##STR1## where R and R.sup.1 are identical or different and each denotes alkyl of 1 to 4 carbon atoms, Z denotes methylene, or ethylene which is unsubstituted or substituted by 1 or 2 methyl groups, and A denotes pyrazole which is linked via a ring nitrogen atom and is unsubstituted or mono- or disubstituted by halogen, methyl or methoxy, triazole which is linked via a ring nitrogen atom and is unsubstituted or mono- or disubstituted by halogen, methyl or methoxy, or imidazole which is linked via a ring nitrogen atom and is unsubstituted or mono- or disubstituted by halogen, methyl or methoxy, has a broadened herbicidal action and is well tolerated by important crop plants.
Depending on the aim to be achieved and the application rate, the new active ingredients are suitable for the selective control of unwanted plants in certain crops consisting of herbaceous or woody plant species, for growth regulation by inhibiting plant growth, or, at appropriately high application rates, for total elimination of plant growth.
The following are suitable meanings for R, R.sup.1, Z and A:
R and R.sup.1 denote alkyl of 1 to 4 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl;
Z denotes methylene, or ethylene which is unsubstituted or substituted by 1 or 2 methyl groups, such as ethylene (--CH.sub.2 --CH.sub.2 --), 1-methylethylene, 2-methylethylene, and 1,2-dimethylethylene;
A denotes pyrazole, triazole or imidazole, each of which is linked via a ring nitrogen atom and is unsubstituted or mono- or disubstituted by halogen, methyl or methoxy, such as 3(5)-methylpyrazole, 4-methylpyrazole, 3,5-dimethylpyrazole, 4-chloropyrazole, 4-bromopyrazole, 4-methoxypyrazole, 3(5)-methyl-5(3)-methoxypyrazole, 4(5)-methyl-1,2,3-triazole, 4,5-dimethyl-1,2,3-triazole, 3(5)-methyl-1,2,4-triazole, 3,5-dimethyl-1,2,4-triazole, 4,5-dichloroimidazole, and 4,5-dibromoimidazole.
In certain asymmetrically substituted azoles, such as pyrazole, 1,2,3-triazole, 1,2,4-triazole and imidazole, two isomers appear in the starting materials because of tautomeric structures, as is illustrated here with reference to pyrazole: ##STR2##
In these instances, therefore, two isomers appear in the new acetanilides; the ratio of the one to the other is determined mainly by the type of the radicals B, C and D and may be of significance for the herbicidal properties.
The new acetanilides may be produced by the following process. They are obtained by reaction of 2-chloro-N-chloromethylacetanilides of the formula II with an alcohol of the formula III in accordance with the following equation: ##STR3##
The substituents R, R.sup.1, Z and A have the above meanings. Some of the 2-chloro-N-chloromethylacetanilides of the formula II are disclosed in U.S. Pat. No. 3,637,847; others may be produced analogously by reaction of the corresponding azomethines with chloroacetyl chloride.
Advantageously, the alcohol of the formula III is employed in at least the molar amount, with reference to 2-chloro-N-chloromethylacetanilide.
The hydrogen chloride liberated during the reaction may be removed as gas, or intercepte
REFERENCES:
patent: 3547620 (1970-12-01), Olin
Eicken Karl
Goetz Norbert
Rohr Wolfgang
Wuerzer Bruno
BASF - Aktiengesellschaft
Harkaway N.
Jiles Henry R.
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