DE1107998B - Preparations for influencing plant growth, in particular for weed control - Google Patents

Description

It is known, s-triazine derivatives (German Auslegeschrift 1 011 904) or diazines or benzodiazines (German Patent 1 035 398) to be used as a weed control agent. In the latter Patent specification has already been made to pyridazine and pyrazine derivatives as a means for To use influence, in particular to inhibit plant growth.

It has been found that to influence plant growth, especially for weed control, such means are particularly suitable, the very specific, well-defined pyridazone of general formula:

AWAY

HN

"N '

-Cl

= 0

contain as a single active ingredient or one of several active ingredients in which A is hydrogen, B is a hydroxyl group and A and B together represent the oxo radical (= O) and R is hydrogen, one optionally by halogen substituted alkyl group, an alkenyl group, an aralkyl group optionally substituted by halogen or a phenyl group optionally substituted by halogen and D the phenyl radical or represents an optionally substituted cycloalkyl group.

These agents are ideal for combating weeds. A particular advantage over Diazine and triazine derivatives consist in the selective destruction of weeds under cultivated plants like onions or cereals, as well as in the shortened aftereffect. In a suitable dosage, the Agents according to the invention also for the total destruction of all plants and for preventing unwanted ones Use vegetation. Compared to the triazine derivatives, the agents of the present Invention a shortened after-effect, which because of the risk of subsequent damage to the Cultivated plants that are sown or planted later is very desirable. Another advantage of the invention Means consists in their, compared with the diazine and triazine derivatives, faster onset of action.

Furthermore, the agents according to the invention are also suitable for achieving other influencing of the

of plant growth,

especially for weed control

Applicant:

Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen / Rhein

Dr. Franz Reicheneder, Dr. Karl Dury,

Ludwigshafen / Rhine, Dr. Herbert Stummeyer,

Mannheim, and Dr. Adolf Fischer, mother city,

have been named as inventors

Plant growth, especially for drainage, to accelerate ripening through premature drying out, z. B. in potato crops, also to reduce the fruit set, to delay the Flowering as well as to extend the harvest period and shelf life.

In suitable concentrations, the agents according to the invention can, under certain circumstances, also be used as agents that promote germination or that promote rooting.
It is known to use pyridine or readily water-soluble pyridine derivatives or salts of these compounds as weed control agents. In comparison with the compounds to be used according to the invention, these substances show only a weak herbicidal action. The use of maleic hydrazide for weed control is also known. The use of this compound has the disadvantage that it has hardly any effect on broad-leaved weeds and that larger amounts are necessary to destroy grasses than when the above-mentioned substances are used according to the invention. The use of substituted pyridines, quinolines and isoquinolines to influence plant growth is also known. Some of them have only a low herbicidal activity, or if they are sufficiently effective, they have insufficient selectivity for cultivated plants.

According to an older proposal, pyridazones, which are in the 4-position, inter alia through an oxyalkyl radical have substituted amino group, can be used as active ingredients for herbicidal agents. In contrast the agents according to the invention have an increased selectivity with approximately the same effect on the weeds

109 609/506

vity towards crops, especially sugar beets.

The pyridazone derivatives to be used according to the invention are prepared in a manner known per se, for. B. by reacting l-phenyl ^ -amino-S-chloropyridazone-6 with aldehydes or acids or acid derivatives, such as acyl chlorides, advantageously in a solvent, for example dimethylformamide. One obtains z. B. by reacting l-phenyl ^ -amino-S-chloropyridazon-o, which is obtained by reacting l-phenyl- ^ S-dichloropyridazon-o, which is obtained by the process described in US Pat. No. 2,628,181 can, obtained with ammonia in methanolic solution, with chloroacetyl chloride the l-phenyl-4-chloroacetylamino-S-chlorpyridazon-ö. The preparation of the chloroacetylamino compound is described in more detail below: 22 parts of 1-phenyl-4-amino-5-chloropyridazone-6 with a melting point of 202 to 204 ^° C. are dissolved in 20 parts of hot N-methylpyrrolidone in a stirred vessel. 11 parts of chloroacetyl chloride are added dropwise with thorough stirring and the mixture is heated to 150.degree. This temperature is maintained for 10 minutes, then allowed to cool slowly, diluted with water, and the crystal slurry that forms is filtered off with suction and recrystallized from methanol. This gives 27 parts of a white crystal powder with a melting point of 124.5 to 125 ° C., which corresponds to a yield of 88% of theory. The other compounds to be used according to the invention can be obtained in an analogous manner. But you can also implement the l-phenyl ^ -amino-S-chloropyridazon-6 directly with the free acids or the aldehydes in the presence or absence of solvents.

Of those which can be used as agents according to the invention for influencing plant growth Connections are named as follows:

1-phenyl-4-hydroxymethylamino-5-chloropyridazon-6

(Mp. 180 to 181 ⁰ C),. l-phenyl-4 - ^, /?, /? - trichloro-s; -hydroxy-ethylamino-

5-chlorpyridazon-o (melting point 163 to 166 ° C),

l-phenyl-4-formamino-5-chloropyridazon-6

(M.p. 242 ° C), 1-phenyl-4-acetylamino-5-chloropyridazon-6

(Mp. 175 to 176 ° C), l-PhenyM-chloroacetylamino-S-chlorpyridazon-o

(Mp. 124.5 to 125 ⁰ C), l-phenyl-4-dichloroacetylamino-5-chlorpyridazon-6

(Mp. 165.5 to 166.5 ° C), 1-phenyl ^ -trichloroacetylamino-S-chlorpyridazon-o so

(Mp. 194 to 195 ° C), l-phenyl-4- (2 ', 4'-dichlorophenoxy) -acetylamino-

5-chloropyridazon-6 (melting point 221 to 222 ° C),

1-phenyl-4- (2'-methyl-4'-chlorophenoxy) acetylamino-5-chloropyridazon-6

(M.p. 214 to 215 ° C), 1-phenyl-4-propionylamino-5-chloropyridazon-6

(Mp. 127 to 128 ⁰ C) ₁ l-phenyl-4 - «- chloropropionylamino-5-chloropyrid-

azon-6 (m.p. 137 to 138 ° C),

l-Phenyl ^ / S-chloropropionylamino-S-chlorpyridazon-6 (M.p. 119 to 120 ° C),

1 -Phenyl-4-Ä, «-dichloropropionylamino-S-chloro-

pyridazon-6 (melting point 148 to 149 ^° C.),

1 -PhenyM-pentachloropropionylamino-S-chloropyrid -

azon-6 (mp. 164-165 ⁰ C),

1-Phenyl-4-A: -chlorobutyrylamino-5-chloropyridazon-6

(Mp. 148 to 15O ⁰ C),

l-PhenyM-ÄjW-dichlorbutyrylamino-S-chlorpyridazon-6 (mp. 149-150 ⁰ C),

1-phenyl-4-isobutyrylamino-5-chloropyridazon-6

(M.p. 117 to 118 ° C),

1-phenyl-4-crotonylamino-5-chloropyridazon-6

(Mp. 137 to 139 ⁰ C),

l-Phenyl-4-laurylamino-5-chloropyridazon-6

(M.p. 72 to 74 ° C),

l-phenyl-tf-a-chlorlaurylamino-S-chlorpyridazon-o
(Syrup), N, N'-bis- [l-phenyl-5-chloropyridazon- (6> yl- (4)] - oxalic acid diamide (melting point 294 ° C),

1-phenyl-4-benzoylamino-5-chloropyridazon-6

(M.p. 188 to 189 ° C),

l-phenyl-4- (2 ', 3', 5'-trichlorobenzoyl) amino-5-chlorpyridazon-6 (mp. 199-203 ⁰ C),

1 -PhenyM-phenylacetamino-S-chlorpyridazon-Ci

(Mp. 110 to 112 ⁰ C),

l-Cyclohexyl ^ -chloroacetylamino-S-chlorpyridazon-6 (M.p. 121 to 122 ° C),

l-CyclooctyM-chloracetylamino-S-chlorpyridazon-o

(M.p. 102 ⁰ C).

The agents according to the invention for influencing plant growth can be used as solutions, emulsions, Suspensions or dusts are used. The application forms are entirely up to you According to the intended use, they should in each case contribute to a fine distribution of the active substance ensure the application. Especially when used as a total herbicide, when it is premature Dehydration as well as defoliation can have phytotoxic effects through the use of per se Carriers, such as high-boiling mineral oil fractions or chlorinated hydrocarbons, increased even further will.

On the other hand, there is the selectivity of growth inhibition when using compared to plants indifferent carriers, e.g. B. in selective weed control in onion or cereal crops, may be more evident.

Medium to high mineral oil fractions are used to produce solutions that can be sprayed directly Boiling point, for example kerosene or diesel oil, also coal tar oils and vegetable oils of animal origin, also cyclic hydrocarbons, for example tetrahydronaphthalene and alkylated naphthalenes, which the active compounds according to the invention, optionally using suitable auxiliary solvents, e.g. B. xylene, can be added. Solutions in low boiling points Solvents such as alcohols, e.g. B. ethanol, isopropanol or methylcyclohexanol, ketones, e.g. B. Acetone or cyclohexanone, ethers, e.g. B. tetrahydrofuran or dioxane, hydrocarbons, e.g. B. benzene, Toluene, xylene, also in chlorinated hydrocarbons, such as chloroform, carbon tetrachloride, tetrachloroethane, Ethylene chloride or trichlorethylene, are less suitable for direct use, rather than in combination with suitable emulsifiers for the purpose of producing concentrates for the preparation of aqueous emulsions.

Aqueous use forms can be made from emulsion concentrates, pastes or wettable powders (Wettable powders) can be prepared by adding water. For the production of emulsions, the Substances as such, or dissolved in one of the above-mentioned solvents, by means of mixing or Dispersants are homogenized in water. As emulsifying and dispersing agents, both

cation-active emulsifiers, such as quaternary ammonium compounds, as well as anion-active, such as soap, soft soap, aliphatic long-chain sulfuric acid monoesters, as well as aliphatic-aromatic sulfonic acids, lignin sulfonic acid, long-chain alkoxyacetic acid acids, but also nonionic emulsifiers, e.g. B. polyethylene ethers of fatty alcohols and Polyethylene oxide condensation products, find use. But it can also consist of active substances, Emulsifying or dispersing agents and possibly solvents existing concentrates are produced which are suitable for dilution with water. Compounds that have sufficient basicity, can also be used as salts in aqueous solution after salt formation with acids.

Dusts can be produced by mixing or grinding together the active substances with one solid carrier material. Examples of these are: talc, diatomaceous earth, Kaolin, bentonite, calcium carbonate, boric acid, calcium phosphate, but also wood flour, cork flour, Coal and other materials. Scatterable granules can, for. B. by using ammonium sulfate can be obtained as a carrier. On the other hand, carriers can also be mixed with solutions of the active substances are impregnated in liquid solvents. By adding wetting agents and protective colloids, powdered preparations or Pastes obtained which are suspendable in water and can be used as a spray.

The various application forms can be used in the usual way by adding substances that improve the distribution, improve adhesion, rain resistance and penetration, such as fatty acids, Resins, wetting agents, emulsifying agents, glue or alginates, the various uses better adapted. The biological spectrum of activity can also be broadened by adding of substances with bactericidal, fungicidal or plant growth-influencing properties as well by combining it with fertilizers.

example 1

Pea, beet, carrot, onion, Mustard and airport seeds sown in transverse rows. After most plants are at the When the cotyledon stage has developed, it becomes a fine-grained one over the plants and the bottom of the pods Mixture, corresponding to an application of 3 kg of l-phenyl-4-chloroacetylamino-5-chlorpyridazon- (6) and 197 kg calcium nitrate per hectare, evenly spread. 5 weeks later it is found that beets and onions have tolerated this treatment without any growth damage. Peas show low chlorotic leaf edge damage, while wild oats, mustard and carrots are almost completely destroyed. Of the weeds that have emerged between the crop plants are Galinsoga parviflora, Matricaria chamomilla, Urtica urens, Poa annua, Chenopodium album and Stellaria media almost completely dead.

The following phenylpyridazones mixed with calcium nitrate are similarly effective when using the same amounts of active ingredient:

l-phenyl-4-acetylamino-5-chloropyridazon- (6),

l-PhenyM-dichloroacetylamino-S-chlorpyridazon- (6),

l-PhenyM-trichloroacetylamino-S-chlorpyrid-

azone- (6),

l-PhenyM-propionylamino-S-chlorpyridazon-Co),
l-PhenyM-je-chlorpropionylamino-S-chlorpyrid-

azone- (6),
l-phenyl - ^ - ^ Ä-dichloropropionylamino-S-chloro-

pyridazon- (6).

Example 2

Sugar beet plants are grown on a cultivated area after singling out and after chopping the soil with l-phenyl-4- / 3, ^, _j ö-trichloro-a-hydroxy-ethylamino-5-chloropyridazon- (6) in one of the applications of 4 kg of active ingredient, dispersed in 1000 l of water, sprayed corresponding amount per hectare. A new growth of weeds between the individual rows is no longer observed until the sugar beet plants are harvested. The following weeds are destroyed during emergence or at the cotyledon stage: Urtica urens, Chenopodium album, Galinsoga parviflora, Poa annua and Panicum sanguinale. The beet plants suffer no damage from this treatment.

Example 3

On a winter barley stand that is weed with wind stalks, chickweed and burdock weeds is, l-phenyl-4-chloroacetylanüno-5-chlorpyridazon- (6) in an amount corresponding to the application of 3 kg per hectare, dispersed in 10001 Water, sprayed. After about 4 weeks, the wind stalk, chickweed and burdock plants are mostly gone dead. The winter barley shows a slight growth depression, but then grows normal without further damage.

Example 4

Beets and onions are sown on a cultivated area. After the plants emerge (stature height 5 to 10 cm) the active ingredient is in an amount that the application of 3 kg of l-phenyl-4-chloroacetylamino-5-chlorpyridazon- (6) per hectare, dispersed in 10001 water, corresponds to the beet or bulbous plants sprayed. 4 to 5 weeks later, the crop plants are growing very well. The effect on the weeds, also after this time, can be seen in the following table, which is the respectively determined Indicates the number of weed plants still present; the individual numbers are averages out of sixteen repetitions.

Untreated 3 kg per hectare
Active ingredient Goosefoot
Chickweed
Knotweed
Cruciferous vegetables
French herb
chamomile
Stinging nettle
Goose thistle
Poppy
Dead nettle
sorrel
Wild oats
Other grasses 112
102
38
52
14th
11
19th
13th
9
21
16
9
116 24
14th
4th
3
0
0
2
4th
5
2
3
6th
11 Total ... 532 78

Claims (3)

PATENT CLAIMS: 1. Means for influencing plant growth, especially for weed control, characterized by a content of pyridazones of the general formula: AWAY HN - C - R Cl "N ' as a single active ingredient or one of several active ingredients in which A is hydrogen, B is a hydroxyl group and A and B together the oxo radical (= 0) and R hydrogen, one optionally through Halogen-substituted alkyl group, an alkenyl group, one optionally substituted by halogen Aralkyl group or a phenyl group optionally substituted by halogen and D denotes the phenyl radical or an optionally substituted cycloalkyl group. 2. Means for influencing plant growth according to claim 1, characterized by a content of 1-phenyl-4-chloroacetylamino-5-chloropyridazon-6. 3. Means for influencing plant growth according to claim 1, characterized by a content of l-phenyl - ^ / ^ / J-trichloro-x-hydroxy-äthylamino-S-chlorpyridazon-ö. Considered publications:
German patent specification No. 1 035 398. © 109 609/506 5.