HU188555B - Defoliating composition containing 1,2,3-thia-diazole derivative as active ingredient - Google Patents

Abstract

The invention relates to an agent for defoliation of plants, preferably cotton plants, containing synergistic mixtures of exfoliating effective 1,2,3-thiadiazol-5-yl-urea or 1,2,3-thiadiazoline-2-id-derivatives with basic from 1 part by weight of the active compounds to 0.5 to 1000 parts by weight of the inactive compounds, wherein 1-phenyl-3- (1,2,3-thiadiazol-5-yl) urea and the like are effective as an effective compound ineffective substances are those from the group of alkali metal hydroxides, amines, carbonates, phosphates and the monocarboxylic acid alkali metal salts.

Description

(57) EXTRAS

The present invention relates to an agent for desiccation of plants, preferably cotton plants, wherein the active ingredient is 1,2,3-thia-diazol-5-yl-urea derivative of the formula I in an amount of 5 to 95% by weight.

R 1 is hydrogen or C 1-4 alkyl; R _{2 is} phenyl or pyridyl;

R _{3 is} hydrogen and

X is O, or the 1,2,3-thia-diazolin-2-id derivative of formula (11) wherein R) is hydrogen;

Rj is phenyl;

X is oxygen and

Suitable equivalents of calcium, magnesium or manganese atom B, and the activator is an alkali metal hydroxide, an alkali metal carbonate, an ammonium carbonate, an alkali metal phosphate, an alkali metal pyrophosphate, an alkylamine, an alkanolamine, a hexamethylene tetramine or an alkali metal.

It is a mixture of 1: 1 to 1: 250 by weight, a solid or liquid carrier or diluent, preferably a mineral, and a surfactant, preferably a fatty acid methyl tauride, a calcium salt of lignin sulfonic acid, tetraethylene glycol nonylphenyl ether and a fatty acid. condensation product based - with at least one.

Ϊ = C, c

X R

I Ϊ c — N — c — N

I \ (I), H

N-C-N / Ri (II)

-1188,555

FIELD OF THE INVENTION The present invention relates to an agent for desiccation of plants, preferably cotton plants, which is a 1,2,3-thiadiazol-5-yl urea or 1,2,3-thiadiazolin-2-id derivative with basic reactants. .

Agents containing 1,2,3-thia-diazol-5-yl-urea and 1,2,3-thia-diazolin-2-id derivatives are already known for decapitating plants (No. 2,506,690, 2,619,861). and German Patent Publication Nos 2 719 8100). However, these are not always satisfactory.

Mixtures of 1,2,3-thia-diazol-5-yl-urea compounds with other antifungal agents are also known, in which compounds having a more or less potent decongestant effect are mutually reinforcing (German Patent No. 2,646,712). disclosure document); therefore, the synergistic effect of these mixtures depends on the two compounds which are already active.

SUMMARY OF THE INVENTION It is an object of the present invention to provide agents, in particular for plant antifouling, in which the known 1,2,3-thiadiazol-5-yl urea or 1,2,3-thia diazolin-2-id derivatives are ineffective with the addition of materials.

This object of the present invention is solved by an agent which is characterized in that the active ingredient is a 1,2,3-thiadiazol-5-yl urea derivative of formula (I).

- in the formula.

R 1 is hydrogen or C 1-4 alkyl;

R ₂ is phenyl or pyridyl;

R ₃ is hydrogen and

X is O - or 1,2,3-thia-diazolin-2-id of formula II

- in the formula

Rj is hydrogen;

R ₂ is phenyl;

X is O and

B is a wedge for a suitable individual of calcium, magnesium or manganese and, as activator, an alkali metal hydroxide. alkali metal carbonate, ammonium carbonate, alkali metal phosphate, alkali metal pyrophosphate, alkylamine, alkanolamine, hexamethylene tetramine or alkali metal oleate

1: 1 to 1: 250 by weight, a solid or liquid carrier or diluent, preferably a mineral and surfactant additive, preferably a fatty acid methyl tauride, a calcium salt of lignin sulfonic acid. based on at least one of tetraethylene glycol nontl-phenyl ether and a fatty acid condensation product.

Examples of compounds of formula (I) include:

-phenyl-3- (1,2,3-thia-diazol-5-yl) -urea, 1-phenyl-1-methyl-3- (12.3-thia-diazol-5-yl) -urea, 1- ( 2-pyridyl) -3- (1,2,3-diaza-diazol-5-yl) urea,

- (4-Pyridyl) -3- (1,2,3-thia-diazol-5-yl) urea, 1- (3-pyridyl) -3- (1,2,3-thia-diazol-5) yl) urea, 1- (3-methyl-2-pyridyl) -3- (1,2,3-thiadiazol-5-yl) urea, 1- (5-methyl-2-pyridyl) -3 - (1,2,3-Thia-diazol-5-yl) -urea, 1- (6-methyl-2-pyridyl) -3- (1,2,3-thia-diazol-5-yl) -urea .

Examples of materials of formula II include:

5- (phenylcarbamoylamino) -1,2,3-thia-diazolin-2: d, calcine salt X 8 H ₂ O,

5- (phenylcarbamoylamino) -1,2,3-thia-diazolin-2-id, magnesium salt X 2 H ₂ O,

5- (Phenylcarbamoylamino) -1,2,3-thia-diazolin-2-id, manganese salt X 3 H ₂ O.

g. Of the listed materials, the following are particularly suitable for use in the present invention:

-phenyl-3- (1,2,3-thiadiazol-5-yl) urea,

1- (2-Pyridyl) -3- (1,2,3-thia-diazol-5-yl) -urea, 5- (phenylcarbamoylamino) -1,2,3-thia-diazolin-2-one. id salts.

The basic reactants which are inactive according to the present invention are as follows:

alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, amines such as alkylamines such as triethylamine, alkagolamines such as diethanolamine, triethanolamine and triisopropanolamine, hexamethylene tetramine, carbonates, Such as sodium carbonate, potassium carbonate, ammonium carbonate, phosphates such as tertiary phosphates such as trisodium phosphate, tricalcium phosphate, pyrophosphates such as tetrakalium pyrophosphate, alkali metal oleate such as sodium oleate.

Preferably, substances are used which adjust the pH of the agent of the invention to above 8, preferably from 9.5 to 11.5.

Surprisingly, the agent of the present invention has an effect that is greater than that of the individual components.

The agent of the present invention is particularly suitable for decortication of cotton plants θ, thus ideally allowing the use of harvesting machines for harvesting sturgeon fruits.

However, other plants can also be advantageously decapitated or regulated in their growth, for example, in terms of promoting germination, formation of side shoots, inhibition of the growth of 3 roots, lawns and dicotyledons such as hibiscus, apple, and other trees and shrubs. It will be appreciated that, as a result, the agent of the present invention can be advantageously used for both defoliation and growth control of plants.

It is known to the person skilled in the art that defoliation is not a herbicidal effect and, moreover, the killing of treated plants is undesirable since the leaves may remain adhered to the destroyed plants and damage the productive plantar parts. When using herbicides, the sense of foliage, that is, to facilitate harvesting and obtain a clearer crop, is lost. Therefore, it is necessary for the plants to survive, whereas the leaves are detached and fallen. This allows the productive parts of the plant to continue to develop and the leaves to be prevented from re-growing. All these tasks are advantageously solved by the agent of the invention and thus the solutions of the prior art are far exceeded.

The agents according to the invention may be used, depending on the intended purpose, in combination with other substances, such as decongestants, pesticides, and pesticides.

In addition, enhancement of the effect and rate of action can be achieved by the addition of potentiators, such as organic solvents, wetting agents. This allows a further reduction of the actual amount of active ingredient used.

The compositions of the invention are used in the form of compositions such as powders, sprays, solutions, emulsions or suspensions, which are liquid.

188,555 and / or as solid carriers or diluents and optionally wetting, tackifying, emulsifying and / or dispersing agents.

Suitable liquid carriers include, for example, water, aliphatic and aromatic hydrocarbons such as petrol _g benzene, toluene, xylene, dklohexanon, isophorone, dimethylsulfoxide, dimethylformamide and mineral oil fractions.

Solid carriers include minerals such as tonsil, silica gel, talc, kaolin, attaclay, limestone, silica, and plant products such as flour. ₁ θ

Surfactants Examples include the following: sodium or calcium lignin sulfonate, poly (oxyethylene) alkyl phenyl ether, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, long chain fatty _1g salts thereof, and substituted benzenesulfonic acids and their salts.

The proportion of the mixture described above in the various formulations may vary widely. For example, the compositions contain from 5% to 95% by weight of the mixture, from 95% to 5% by weight of a liquid or solid carrier, and optionally up to 30% by weight of a surfactant.

The weight ratio of the components in the characterized mixture depends on the sensitivity and resistance of the plants, the time of application, and the climatic and soil conditions.

The amount used to achieve the desired desiccation effect is usually from 1 to 10,000 grams of the mixture, preferably

10-1000 g mixture / ha.

The agent of the present invention may be applied in a conventional manner, for example, with water as a vehicle, using a perineal fluid of about 100 to 100 liters / ha. The agent can also be used in the so-called "Low-Volume" or "Ultra-Low-Volume" process. 35

The decolorizing agents and basic additives of the above-described mixture are known and can be prepared by methods known per se.

For example, the following ingredients are used in the preparation of the compositions:

a) 95% by weight% 1% by weight

b) 80% by weight 3% by weight c) 20% by weight 2% by weight of a mixture consisting of 1 part 1-phenyl-3- (1,2,3-thiadiazol-5-yl) of urea and 1 part of potassium carbonate, kaolin, 45

Mixture of N-methyl-N-oleyl taurine sodium salt and lignin sulphonic acid calcium salt based on 1 part of 5- (phenylcarbamoylimino) -1,2,3-thiadiazolin-2-id calcium salt and 6 parts alkylamine, calcium salt of lignin sulfone band, ammonium salt of tetraethylene glycol phenyl ether monoacetic acid ester, colloidal silica 55, which is 1 part 5- (phenylcarbamoylamino) -1,2,3-thia- consisting of diazoline-2-id-magnesium salt and 10 parts potassium phosphate, tonsil, 60 cellulose, fatty acid condensation product-based wetting agent

d) 5% by weight, 10% by weight, 5% by weight of a mixture consisting of 3 parts of 1-phenyl- (1,2,3-thiadiazol-5-yl) urea and 10 parts of ammonium carbonate, tonsil, cellulose , a fatty acid condensation product based wetting agent.

For example, the agents are prepared by mixing the individual ingredients in a drum and grinding them in a mill.

These agents can be applied directly or after dilution with water to the plants to be treated. The pH of these compositions is particularly significant for enhancing the effect of the mixture and is therefore preferably greater than 8, preferably 9.5 to 11.5.

The following examples are based on experiments conducted in greenhouses, usually on cotton plants with 5-8 true leaves. The agents were used in the form of aqueous formulations based on the formulations given above.

Experiments were evaluated by counting the number of leaves dropped after application and calculating the percentage of total leaves. Each experiment always had the same number of leaves per experimental item. The number of leaves per experiment varied from experiment to experiment, with between 20 and 28 leaflets per experiment.

The following examples provide data on the active ingredient, the basic reactant, the mixture, the amount used, and the specified percentage of defoliation. After the percentage of defoliation achieved with the combination according to the invention, the value calculated in SRColby, which would be expected in the case of an additive effect, is also partially enclosed in parentheses (SRColby, "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weels 15/1 ( 1967) p. 20-22].

The calculation was made using the following formula:

where

X = defoliation% with substance A, p kg active substance / ha

Y = defoliation% with substance B, q kg active ingredient / ha

E = Expected decalcification

A + B at p + q kg / ha

If the observed value is greater than the Colby E value, then the combination is synergistic. The results of the following examples clearly illustrate the enhancement of the desiccant by the basic reactants which are ineffective in themselves.

The following application examples were based on a formulation containing 20% by weight of the active ingredient or activator alone, or a mixture of the total amount detailed in the following examples, 70% by weight of tonsillon, 8% by weight of cellulose and 2% by weight of fatty acid condensation product. .

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Example 1

Example 4

Young 5-leaf cotton plants were treated with the following components of the above agent, namely the active ingredient, the basic reactant and a mixture thereof (repeat 4 times). The amount of water used was 500 liters / ha. After a few days, we determined the percentage of leaves dropped. The results are shown in the following table:

leaf used - E component (Colby) in g / ha%)

1-phenyl-3- (1,2,3-thia-diazol-5-yl) urea = 1 K, CO ₃ = 11 80 35 500 0 K ₄ P, O ₇ = 111 500 0 I + II 80 + 500 70 (35) Ι + 1Π 80 + 500 60 (35)

Example 2

Young cotton plants were treated as in Example 1. The results are shown in the following table:

components used quantity g / ha of letter- telcnítés %-in E (Colby by) 1-Phenyl-3- (1,2,3-thia-diazol-5-yl) carbanide = 1 K, CO ₃ = II 80 57 5Ó0 0 Well, CO _a = XV 500 0 (NH,), 00, = IV 500 0 KOH = V 500 0 = I + II 80 + 500 70 (57) I + XV 80 + 500 85 (57) I + IV 80 + 500 80 (57) I + V 80 + 500 60 (57)

Young cotton plants were treated as in Example 1. The lower percentage effect compared to the previous examples is due to the unfavorable environmental conditions during the conduct of the experiments in the winter months. The results are shown in the following table:

components used quantity g / ha of Icvéltelenítés %-in 1-Phenyl-3- (1,2,3-thia-diazol-5-yl) -carbamtd = I 80 0 K, CO ₃ = II 500 0 1000 0 I + II 80 + 500 29 5- (phenyl-carbamoyl imino) -l, 2,3-thia · -diazolin-2-id, calcium salt = IX 80 0 1X + II 80 + 500 24 1- (2-Pyridyl) -3- (1,2,3-thiadiazol-5-yl) urea = X 80 0 X + II 80 + 500 23.5

Example 5

Young cotton plants were treated as in Example 4. The results are shown in the following table:

components used quantity g / ha of levélte- regrowth of micro %-in E (Colby by) 5- (phenylmethyl karbanioil- 500 17 -inino) -1,2,3-thia-diazolin-2-id-calcium salt = XI K ₃ CO ₃ = II 500 0 XI + II 500 + 500 39 (17)

Example 3

Young cotton plants were treated as in Example 1. The results are shown in the following table:

components used quantity g / ha of levélte- Icnítcs %-in E (Colby by) l-phenyl-3- (l, 2,3-thia- -diazol-5-iD-urea = I sodium olate = VI 40 29 500 0 trictanol = VII 500 0 triethanolamine = Vil 500 0 I + VI 40 + 500 33 (29) I + VII 40 + 500 43 (29) I + VIII 40 + 500 62 (29)

Example 6

Young Hibiscus plants with 7-10 expanded leaves were treated as in Example 1. The percentage of fallen leaves was determined 6 days after application.

components quantity used g / ha of levélte- liming %-in E (Colby by) l-phenyl-3- (t, 2,3-thia- 25 0 d azole-5-yl) urea 10 4 K, CO II 500 0 R "P, O, III 500 0 Ι Π + 25 + 500 14 (0) 10 + 500 46 (4) I + I1I 25 + 500 11 (0) 10 + 500 54 (4)

188 555

Example 7

Young cotton plants were treated as in Example 1. The results are shown in the following table:

components used quantity g / ha of levélte- liming %-in E (Colby by) l-phenyl (l, 2,3-thia- 40 19 -diazol-5-yl) -. -ureas - I K, CO ₃ II 3000 0 K ₄ P, 0, ill 3000 0 I + II 40 + 300 57 (19) 40 -t-1000 67 (19) 40+ 3000 71 (19) 40 + 10,000 76 (19) I + UI 40 + 1000 62 (19) 40+ 3000 86 (19) 40 +10000 90 09)

Example 8

Young cotton plants were treated as in Example 1. The results are shown in the following table:

components used quantity g / ha of % of mailing E (Colby by) l-phenyl-l-methyl - (l, 2,3- 40 63 thia-oxadiazol-5-yl) - -urea K.CO, 500 0 k, after ₄ 500 0 40 + 500 71 (63) 40 + 500 76 (63)

Example 11

Young cotton plants were treated as in Example 1. The results are shown in the following table:

components used quantity g / ha of ievélte- liming %-in E (Colby by) 5-phenylcarbamoylimino) -], 2,3-thia-diazolin-2-id, magnesium salt = XIII 40 52 K, PO ₄ = XVII 500 0 XIII XVh where n + 40 + 500 71 (52)

components used quantity g / ha of levélte- liming %-in E (Colby by) l-phenyl- (I, 2,3-thia- -diazol-5-yl) urea = l 40 33 K, COj = Π hexamethylene 540 0 -tetramine - XVI 540 0 I + II 40 + 500 71 (33) I + XVI 40 + 500 48 (33)

Example 9

Young cotton plants were treated as in Example 1. The results are shown in the following table:

Example 12

Young cotton plants are given in Example 1

treatment. The results are shown in the following table: components used quantity g / ha of levélte- liming %-in E (Colby by) 5-phenyl-karbanioil imino) -l, 2,3-thiadiazolyl-2-id. manganese = XIV 40 32 K, P0 ₄ = 'XVII 500 0 XVII + XIV 40 + 500 82 (32)

components used quantity g / ha of ievélte- liming %-in E (Colby by) l-phenyl (l, 2,3-thia- 40 64 -diazol-5-yl) - -urea = I K, CO, = H 500 0 K.PO ₄ = XVII 500 ü Ι Π + 40 + 500 86 (64) I + XVII 40 + 500 91 (64)

Example 10

Young cotton plants were treated as in Example 1. The results are shown in the following table:

Example 13

Young citrus plants with 21-27 leaves were treated as in Example 1. The results are shown in the following table:

amount of foliar application used len g / ha% l-phenyl-G, 2,3-thia-diazol-5-iurea urea 300 19

KjCO, 1000 0

300 + 1000 48

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Example 14

Young Urtica urens plants were sprayed with the components of the above agent, or mixtures thereof, as described below. Three weeks later, the fresh weight of the above-ground parts of the plant was determined. The following table shows relative values of plant height and fresh weight (untreated = 100). Plants are, as desired, more robust, lower, and thus more stable in growth compared to untreated control. Nevertheless, their fresh weight is higher. The results of the experiment show that the agent of the invention has a greater growth regulating effect than the individual components.

components employee concentration ppm relative plant- height relative fresh- -weight l-phenyl (l, 2,3-thia-diazol- -5-iD-urea 2 79 113 K, CO 26 100 100 2 + 26 75 131

Patent claims

Claims (11)

A decolorizing agent, characterized in that it contains 5 to 95% by weight of the active ingredient of the formula (I) A 1,2,3-thiadiazol-5-ylcarbamide derivative wherein R 1 is hydrogen or C 1-4 alkyl; R 1 is phenyl or pyridyl; R ₃ is hydrogen and X is O - or 1,2,3-thia-diazolin-2-id of formula II Rj is hydrogen; R 1 is phenyl; X is O and B is a suitable equivalent of calcium, magnesium or manganese, and as activator is an alkali metal hydroxide, an alkali metal carbonate, an ammonium carbonate, an alkali metal phosphate, an alkali metal pyrophosphate, an alkylamine, an alkanolamine, a hexamethylene tetramine or an alkali metal; 5 in a weight ratio of 1: 1 to 1: 250, a solid or liquid carrier or diluent, preferably a mineral, and a surfactant, preferably a fatty acid methyl tauride, a calcium salt of lignin sulfonic acid, tetraethylene glycol nonyl phenyl ether and based on a fatty acid condensation product with at least one. 2. An agent according to claim 1, wherein 1-phenyl- 3- (1,2,3-thiadiazol-5-yl) urea, 1-phenyl-1-methyl-3- (1,2,3-thiadiazol-5-yl) urea, or 1 Contains (2-pyridyl) -3- (1,2,3-thiadiazol-5-yl) urea. 3. An agent according to claim 1, characterized in that it contains sodium or potassium hydroxide. 4. An agent according to claim 1, characterized in that it contains triethylamine, diethanolamine, tri ethanolamine, triisopropanolamine or hexamethylene tetramine. 20 5. An agent according to claim 1, characterized in that it contains sodium carbonate, potassium carbonate or ammonium carbonate. 6. An agent according to claim 1, characterized in that it contains trisodium phosphate, tri-potassium phosphate, tetra-25-sodium pyrophosphate or tetrakotassium pyrophosphate. 7. An agent according to claim 1, characterized in that it contains sodium oleate. An agent according to claim 1, characterized by. 30 1-Phenyl-3- (1,2,3-thiadiazol-5-yl) urea with potassium hydroxide, potassium carbonate, ammonium carbonate, tetrakalium pyrophosphate, triethylamine, triethanolamine or sodium contains a mixture of oleate, 35 9. An agent according to claim 1, characterized in that it comprises a mixture of 1- (2-pyridyl) -3- (1,2,3-thiadiazol-5-yl) urea with potassium carbonate. 10. An agent according to claim 1, characterized in that it comprises a mixture of the calcium salt of 5- (phenylcarbamoylamino) -1,2,3-thiadiazoline-2-id-cal with potassium carbonate. 11. An agent according to claim 1, wherein the pH is greater than 8, preferably 9.5 to 11.5. 1 figure -6188555 NGO ₄ : A01 Ν 43/82 c-Η X I Ν-C I