DD150683A1 - MEANS OF THE PROTECTION OF PLANTS AGAINST FROST CHEATS - Google Patents

Abstract

The invention relates to novel substances for the protection of plants against frost damage, characterized in that the plant to be protected is treated from a suspected sinking of potassium with an agent which has an effective concentration of an N-substituted 3,6-dioxo-hexahydro-pyridazinyl-4 acetic acid derivative of the general formula I contains. The various substituents R have the meaning given in the description. An application is possible in agriculture and horticulture.

Description

220580

AO1 Ή 43/58

Description of the invention Title of the invention

Means for protecting plants against damage to the prostate

Field of application of the invention

The present invention relates to compositions for protecting plants against frost damage containing N-substituted 3,6-dioxo-hexahydro-pyridazinyl-4-acetic acid derivatives as active ingredients, and their use in agriculture and horticulture.

Characteristic of the known technical solutions

The prevention of Prost damage in crops of cultivated plants is an economically important problem of agriculture and horticulture, have therefore already described some measures and drugs to "enhance the cold resistance, d _e h in resistance ability of crop and ornamental plants to low temperatures and "On the one hand, these are physical methods, such as the use of polymers ₉ foams and mists, the other is the application of chemical compounds." These are protective agents against the freezing death of plant cells caused by membrane damage, or

put the plant metabolism down and cause a reduction in vegetative turnover and so keep the plant in "dormatem state", so that it is much less sensitive to Prost ₀ in US Pat 3,867,126 _o be some 3,6-dioxo-hexahydro- pyridazinyl-4-acetic acid derivatives to protect plants from damage caused by the prostate, "their effectiveness is not satisfactory, especially at low application rates,"

Object of the invention

The aim of the invention is the development of new anti-proliferative agents for crops with improved properties «

Present the essence of the invention

The invention has set itself the task of creating new means for protecting plants against prostate damage, which cause a good Prostschutz with low phytotoxicity and reduced application rate, To solve this problem agents are proposed, which are characterized by a content of one or more N-substituted 3,6-dioxo-hexahydro-pyridazinyl-4-acetic acid derivatives of the formula I

in which

12 '

R and R independently of one another represent hydrogen, lower alkyl or phenyl,

R ^ is hydroxy, amide or OR, R is lower alkyl or metal, R ^{5 is} hydrogen or OR and R is hydrogen or an acyl radical of an organic acid

The N-substituted 3-6-dioxo-hexahydro-pyridazinyl-4-acetic acid derivatives of the formula I which are to be used according to the invention as active substances have, surprisingly, better antifreeze properties than the dioxo-hexahydro-pyridazinyl-acetic acid derivatives known from the prior art. In addition, they are distinguished by a good plant tolerance. The compositions according to the invention thus represent an enrichment of the state of the art. 3,6-dioxo-hexahydro-pyridazinyl-4-acetic acid and some of its derivatives are described in the literature Compounds which are used can be prepared by methods known per se (K, KNOEVENAGEL, Ro HIMMELREICH, DT 1542989) by refluxing stoichiometric amounts of substituted hydrazines with citric acid or corresponding derivatives for several hours. Esters, amides and salts are obtained by reacting stoichiometric amounts of the alcohols, amines or metal hydroxides with N-substituted 3,6-dioxo-hexahydro-pyridazinyl-4-acetic acids. Salts are physiologically well tolerated

Metal ions such as Z ₀ Be Na, Ca or Mg into consideration.

As examples of active ingredients of the compositions according to the invention, the compounds are mentioned in Table 1.

Table 1: 3s6-DLOXo-hexahydro-pyridazinyl-4-acetic acid

derivatives R ¹ R ² the general F R ⁵ ormel I CH-C ₆ H ₅ Mp / ⁰ Q / Verb. CH ₃ H r3 R ⁴ H R " CH-C ₆ H ₅ amorphous 1 CH ₃ H OH - OR ⁶ jl " - 58 2 CH ₃ H OH - OR ⁵ H .60 3 CH ₃ H OH - OR ⁶ CO-C ₂ H ₅ 118 4 CH ₃ H OH A - OR ⁶ CO-CH = 132 5 C ₂ H ₅ H OR ⁴ CH-, H r CO-CH a amorphous 6 H OH OR ⁶ - 104 7 C ₂ H ₅ H OH - OR ⁶ H 129 8th OR ⁴ CH ₃ H

Verb, Hr * R ¹ R ² r3 R ⁴ R ⁵ R " Pp-Z ⁰ CJ -9 C ₂ H H OR ⁴ C ₂ H OR ⁶ H 128 10 H OH H - amorphous 11 C ₃ H ₇ H OH OR ⁶ H 124 12 C ₃ H ₇ H OR ⁴ CH ^ OR ⁶ H 142 13 C ₃ H ^ H OR ⁴ OR ⁶ H . 142 14 H OH - OR ⁶ H 136 15 tC ₄ H ₉ H OR ⁴ CHO OR ⁶ H 158 16 CH ₂ -C ₆ H ₅ H OH OR ⁶ α H -78 17 18 19 20 CH ₂ -C ₆ H ₅ ° ^6H 5 ° ^6H 5 CH ₃ H H .H H OR ⁴ OH OR ⁴ OR ⁴ CH ₃ Na OR ⁶ OR ⁶ OR ⁶ OR ⁶ MMMM 110 260 260 21 22 CH ₃ CH ₃ CH ₃ CH ₃ OH OR ⁴ CH ₃ OR ⁶ OR ⁶ H H Oil 135 23 ° 6 ^H 5 ^C 6 ^H 5 OH - OR ⁶ H 260 24 25 ^C 6 ^H 5 CH ₃ ^C 6 ^H 5 H OR ⁴ OR ⁴ OH OR ⁶ ₉ OR ⁶ H H 260. -73 26 CH ₃ H OR ⁴ YJMY OR ⁶ H 101-108

Ys = 1-methyl-3,6-dioxo-4-hydroxy-hexahydro-pyridazinyl-4-acetic acid

The present invention as active ingredients to verv / ending compounds cause a strong increase in hard frost when the treated plants _o

The difference in the application rates in which an antifreeze effect occurs or "phytotoxic" damage is observed is very large, so that when used in the required concentration no damage to the crops takes place. For this reason, the compounds are useful as agents for anti-prostate agents.

Depending on the specific application, the N-substituted 3,6-dioxohexahydro-pyridazinyl-4-acetic acid derivatives to be used according to the invention can be converted into the customary formulations, such as solutions, emulsion concentrates, wettable powders, dusts, pastes, granules, microcapsules, etc.

These are produced in a known manner, eg »B. by stretching the active compounds with solvents and / or excipients, if appropriate using emulsifiers and / or dispersants (see "Agricultural Chemicals, March 1960, pages 35-38)." Suitable as Pormulxerungshilfsstoffe are substantially: solvents, such as average alcohols (butanol , pentanol ^ paraffins, dimethyl sulfoxide, ethylene glycol and barrels;! carriers such as ground natural minerals (e.g. _o B "kaolins, clays, Bimsgries, talc, chalk) and synthetic emulsifiers such as nonionic, anionic and cationic emulsifiers (e.g." B _e polyoxyethylene Pettsäureester , Polyoxyethylene-Pettalkoholether, alkylsulfonates, arylsulfonates) and dispersants such as lignin, liquors and Methylcelluloseο

All preparations of the active compounds can be other than those already mentioned extenders contain special additives such as agents for improving the adhesion to plants, corrosion inhibitors, defoamers, etc. _ee Due to the low chemical reactivity of the agent is a combination with other systemic and non-systemic pesticides and means for controlling , biological processes possible and meaningful

The formulations generally contain between 0.5 and 95 % by weight of active ingredient, preferably between 5 and 90 %. The active ingredients can be used in the form of their formulations or the forms of use prepared therefrom, such as ready-to-use broths. iron, z _e B ₀ by spraying, spraying, dusting, spreading or pouring «

The following examples serve to illustrate the antifreeze effect of the agents according to the invention.

Ausführungsbeispiei

active substance

Solvent / emulsifier

2 parts by weight DMSO 7 ti paraffin oil .1 H Alkylphenylpolyglycol- 0.5 Il ether

Mix the required for the desired drug concentration in the spray "amount of active ingredient with the specified amount of solvent / emulsifier and dilute the concentrate with water, winter barley is grown in pots at a temperature of + 5 ⁰ C." After the primary leaves an average length of 8 cm, the plants are sprayed with the prepared middle broths to drip-wet 36 hours after application, they are exposed in a climatic chamber for 2 hours the specified frosts, then slowly thawed for 24 hours at 0 ⁰ C and kept at room temperature for 3 days Prosthärte was the% ual share of dead plants determined

Table 2

Number of dead plants in % active ingredient "foliar application, drug concentration 250 / ug / m

(Nr ₀ d, Verb _o ) -6 ⁰ C -8 ⁰ C -10 ⁰ O -12 ⁰ C ~ U ⁰ G

Unbeho control 0 0 15 60 100

Pydanon (known) 0 0 13 43 78

2 0 0 8 25 60

.7 0 0 .9 25 65

11 0 0 10 35 68

16 0 0 .9 25 60

19 0 0 10 30 64

Claims (1)

invention claim 1 © Means for protecting plants against frost damage, characterized in that they contain as active ingredients at least one M-substituted 3,6-dioxo-hexahydro-pyridazinyl-4-acetic acid derivative of general formula I, H ₂ (I) = O in which 12 R and R independently of one another represent hydrogen, lower alkyl or phenyl, R ^ for hydroxy, amide or OR ^, R for lower alkyl or metal, R ^{5 is} hydrogen or OR ⁶ and R is hydrogen or an acyl radical of an organic acid, in addition to conventional extenders and / or surfactants contained Use of the preparations according to item 1, characterized in that crops are treated with these before a suspected frost fracture, Use of preparations according to item 1, characterized in that they are used as antifreeze in crop protection.