DD143851A1 - HERBICIDE MEDIUM - Google Patents

Abstract

The invention relates to herbicidal agents which 1-hydroxyalkanephosphonic acid dialkyl ester and 2,4-Bin ~ alkylaminio-t5 ~ chloro-s-triazines in proportions of 5 to 1 to 10 to 1 included. The combinations are as after the emergence of the plants as selective herbicides in Grain crops applicable.

Description

The invention can be used in agriculture and horticulture for weed control.

Characteristic of the known n technical solutions

It is known that s-triazines, as potent inhibitors of photosynthesis in the various general and specific applications, have found access to industrially produced crop protection agents.

The applied on the Agj? Arflachen application rates generally move by about "2 kg of active ingredient / ha triazines have in the application of a considerable long-term effect, which can often exclude or delay a short-term reproduction of crops often.

Combinations of phosphonic acid compounds with s-Tria ™ zinen are known »So are proposed in DD-PS 123 261 agents that are suitable for Krautabtötung in potatoes. As a mixing partner, 1-aminoalkanephosphonic diesters are mentioned, which, however, possess strong herbicidal activity even without addition of triazine and are known as commercial or experimental products.

ο ι / 4 - 2 -

Object of the invention

The aim of the invention is to develop herbicidally effective combinations based on s-triazines, which reduce the application rate of these compounds to agricultural land and consequently enable their more rational use. ·.

Explanation of the essence of the invention

This object is achieved in that the herbicidal agent in addition to conventional excipients and carriers as active ingredients 1-Hydroxyalkanphosphonsäurediester the general formula

T) ΛΤΤ

in the

Ε ,, and Rp, which may be the same or different,

H or. Älkyl or represent with the C atom they bind a cyclohexyl radical, and

Eu is an alkyl radical having 1 to 12 carbon atoms. :: -.

and triazines of the general formula

cc

in the

B. ^ and Rg, which may be the same or different,

Alkyl radicals with Λ to 4 C atoms mean, in weight

3174 - 3 - 1987

Ratio of 5 to 1 to 20 to 1 included.

While 1-Hydroxyalkanphosphonsäurediester when used only weak to at most average herbicidal activity can be seen, it was found that these compounds in combination with Triazinmengen far below the usual for 2,4-bis-alkylamino-6-chloro-s-triazines applications limit, which have good herbicidal activity required for practical use.

embodiments

The herbicidal activity was tested by spraying emulsified or suspended formulations of the active compound mixtures in the after-flow method onto monocotyledonous and dicotyledonous weeds and aerial strains. An evaluation was made 21 days after the application. Monocot test plants were Avena sativum (oats), Triticum aestivum (wheat) and Hordeum vulgare (barley). The dicotyledonous test plants used were Chrysanthemum carinatum (weedy flower), Tripleurospermum inodora (chamomile), Sinapis alba (mustard) and Lycopersicon esculentum (tomato).

The results are based on a rating of 1 to 9 with the following meaning:

1 corresponds to 100% killing the pi ian 2 U 90- 99% tt tt tt 3 tt '70-89% It tt tt 4 It 51-69% tt ti ti It 50% It It tt 6 M 30- 4-9% It tt tt 7 tt 10- 29% tt It tt 8th ti 1-9% tt tt tt 9 tt 0% tt ti

Ä - 4- -. 198?

"Sr

From the table it can be seen that "the sole application of the dosages of the individual components used in the mixtures can lead to almost total ineffectiveness against certain plant material." Moreover, the synergistic effect is limited only to combinations of 1-hydroxyalkane phosphonic diesters with 2, 4-bis- alkylamino-6-chloro-s-triazines.

6 ~ Alkylmercapto ~ s-triazines analogous structure in mixture with the phosphonic acid esters only an additive effect on the herbicidal action (see Example J).

Furthermore, examples have selective herbicidal effects. It can be seen that dicotyledonous weeds are severely damaged, while monocotyledonous crops show little or no dying-off symptoms in the postemergence process. As a result, combinations according to the invention of use as selective herbicides are obtainable, for example, in cereal crops. Rormaldosierung of 2,4-bis-alkylamino-6-chloro-s-triazines for weed control (1.5 to 2.0 kg of active ingredient / ha) does not show this selectivity towards cereals.

The so applicable herbicide mixtures are distinguished by the high content of 1-hydroxyalkanephosphonic diesters to be extremely toxic and fast metabolizing funds from _o

In general, the herbicidal effect has subsided so quickly that even replant cultures suffer no more damage. For the application of the combinations in plant stands are usually produced with the addition of inert carriers, oils, wetting agents, adhesives, dispersants and solvents producible spray powder, suspension spray or emulsions.

The preparation of the individual active ingredients used in the combinations is carried out by known methods. For the synthesis of the claimed phosphonic acid compounds, which is hitherto not yet known industrially, for example, the following preparation procedure leads to high yields:

- 5 - 1987

Preparation of I- hydroxycyclohexanphosphonic diesters;

Zquimolar amounts of cyclohexanone and dialkylphosphine are mixed together, and at room temperature, the dropwise addition of a uniform amount of diethylamine is begun. The Reaktionsmisehung soon warms up by the onset of 'exothermic reaction. After all the diethylamine was added, with the self-heating is maintained in the temperature range of 50 to 60 ⁰ C, followed by a 1-2 hour stirring of the mixture at 70 to 80 ⁰ C; Finally, the unchanged diethylamine, which consequently acts only catalytically, and residues of the cyclohexanone are distilled off in a boiling water bath and by means of a water-jet vacuum. The viscous, often crystallizing residues contain in almost quantitative yields the 1-Hydroxycyclohexanphosphonsäurediester «

Table: Effect of the combinations according to the invention against mono- and dicotyledonous weeds in the postemergence process.

Individual connections and combinations

Application rate per hectare average damage of dicotyledon EClanzen

average damage to monocotyledonous crops

Example A:

1) 1-Hydroxycyclohexanphospho acid tert.-0 _s O-dibutyl ester

2) 2H-bis-ethylamino-6-chloro-s-triazine

3) combination 1). + 2)

2 kg

.125 p

1875 g D + 125 S 2) 7.8

8 _t 8 2.8

9 6.3

Example B:

1) 1-Hydroxycyclohexanphosphonsäure O »di-bishexyl ester

2) 2-ethylamino-4-isopropylamino-6-chloro-s-triazine

2 kg

333 p

182 g

125 g

.95 g

6.5

6.5 7.2 7.8 8.8

9 9 9

Continuation table:

1667 Application rate per hectare D + 333 G 2) average damage. diketyJLejL ·. Px lan zen 2 average damage to monocotyledonous crops Individual connections and combinations -1818 G D + 182 G 2) 2 ,8th '. 6.5 3) combination 1) + 2) 1875 G D + 125 G 2) 2 ,8th 6.5 1905 G D + 95 G 2) 2 , 0   6.5 G 3 6.5 •

Example 0 °.

1) 1-Hydroxycyclohexanophosphoic acid 0.0-dipropyl ester

2) 2-methylamino-4-isopropylamino-6-chloro-triazine

3) combination 1) + 2)

2 kg

8.5

s. Example B G 2) s. Example' B s. example B 1818 g 1) + 182 G 2) , 2.2 6.8 1875 g D + 125 4.0 • 7.0

Continuation table:

Binzel connections and combinations

Application rate per hectare

Example D:

1) 1-Hydroxy-1-methylpropane-phosphonic acid-0,0-diisobutyl ester

2 kg

2) 2,4- »bis-ethylamino-6-chloro-s-triazine 182 g

125 g

95 g

3) combination 1) + 2) 1818. g 1)

1875. g D

1905 g 1)

average damage to the dicotyledonous plants

G 2>. 8th ,8th 182 G 2) 2 , 7 125 G 2) 2 , 7 95 3 2

average damage to monocot cultures

7.8

9 ·

8 8 8

Continuation table:

Individual connections and combinations

Application rate per hectare average damage to dicotyledonous plants

average damage to monocotyledonous crops

Example Et D

1 - * hydroxypropoxylic acid 0,0-dibutyl ester

2) 2-Athylamino-4 · isopropylamino-6-s-triazine

3) combination 1) + 2)

2 kg

7.8

s. Example B s. Example B

1818 g 1) + 182 g 2) 2.5 1875 S D + 125 g 2) 2.8

Beis piel Έ ι

1) 1-Hydroxy-1-methyläthophophosphoric acid, 0,0-bis-2-ethylhexylester

2) 2,4-bis-isopropylamino-6-chloro-s-triazine

2 kg

333 g 182 g

125 S 95 g 7.0

8.1

9 9 9 9

s. Example B I 7.8 8.3 I

.Jk VD

Continuation table:

Single connections combinations

Application rate per hectare

average damage to the dicotyledonous plants

average damage to monocotyledonous crops

3) combination 1) + 2)

1667 g 1) + 333 g 2) 2,4

1818 g 1) + 182 g 2> 2.6

1875 g D + 125 g 2) 3.1

1905 g D + 95 g 2) 3.8

8.0 8.2 8.2 8.3

Example G:

1) I-Hydroxycyclohexanphospho ns aur e-0,0-diethyiester

2) 2-ethylamino-4-isopropylamino-6-chloro-striazine

3) combination 1) + 2)

2 kg

s. Example B

1667 g 1) - 333 g 2) 1818 g 1) + 182 g 2) 1875 S D + 125 g 2) 1905 g D + 95 g 2)

Example B

s. Example B

8 8 8 8

comfort table:

Costs per hectare 333 S 2) average damage to the dicotyledonous plants average damage to monocotyledonous crops Binzelverbindungen and Kombinatio neη 182 S 2) Example H: 2 kg 125 G 2) 1) 1-hydroxycyclohexane. ph. phosphonic acid-0, C-2-ethyl hex-1 s. example 95 S 2) .s, example F s. Example J ¹ 2) 2,4-bis-isopropylamino-6-chloro-s-triazine 1667 S 1) + 3.0 7 3) combination 1). + 2) 1818 g 1) + 3.5 8th 1875 S D + 3.6 8th 1905 g D + 3.8 8th Example I:

1) 1-hydroxycyclohexanephosphonic acid 0.0-

dibutyl ester 2 kg

2) 2-ethyl-amino-4-isopropylamino-6-chloro-s-triazine s. Example B

3) Combination 1) + 2) 1818 g 1) + 182 g 2)

1875 g D + 125 S 2)

7.8

Example B

2.0 2.8

8 s. Example B

7.5

Continuation: Table

Individual connections and combinations

Application rate per hectare

Example J;

1) I-hydroxycyclohexanephosphonic acid O, O-dibutyl ester

2) 2-methylthio-r4-ethylaraino-6-isopropylamino-s-triazine

3) combination 1) + 2)

2 kg

333 p

182 g

125 g

95 g

1667 g!

Isis g ι;

1875 g! 1905 g!

average damage to the dicotyledonous plants

average damage to monocotyledonous crops

333 g 2)

182'g 2)

125 g 2)

95 g..2)

7.8

2.2 2.2 2.5 3.2

2.0 2.5 3.0 3.8

6.3

7.5

7.5

6.3 6.7 6.7 6.7.

Claims (1)

2 t 1987 invention claim Herbicidal agents, characterized in that they are in addition to conventional excipients and carriers as active ingredients 1 ~ Hydroxyalkanphosphonsäurediester the general formula R. .OH in the R ^ and Rp _S which may be the same or different; H or alkyl or with the C atom which binds them represent a cyclohexyl radical and R ~ is an alkyl radical having 1 to 12 carbon atoms, and triazines of the general formula in the R ₁ and R ₂ , which may be the same or different, Alkyl radicals having 1 to 4 carbon atoms, in a weight ratio of, 5 to 1 to 20 to 1,