SK721689A3 - Algicidal and herbicidal agent on organic monoammoniacal bromides base - Google Patents

Abstract

The algicidal and herbicidal agent made based on the organic mono ammoniacal bromides contains mono ammonium bromides with a general formula (I), (II) or (III) as an active compound, where R means a linear or branched alkyl chain with 1 up 18 carbon atoms, 2-hydroxyethyl, R1 means a linear or branched chain CH3 up to C18H37, C11H23NH(CH2)2, C11H23CONCH3(CH2)2, C11H23COO(CH2)2, (CH3)3, C-C6H4-CH2, C6H5-CH2, C6H5CO(OCH2CH2)n, where n =1, 2, 3 HOCH2CH2, HC-triple bond-C-CH2, H2C=CH-CH2, C6H5CH=CH-CH2, CH3CH=CH-CH2; R2 is a linear or branched alkyl chain with 2 up 14 carbon atoms, R3 is a linear or branched hydrocarbon chain with 6 up to 18 carbon atoms, C11H23COO(CH2)2, X = (CH2)n, where n = 4, 5, 6 (CH2CH2)2O; R4 means a linear or branched hydrocarbon chain C6H13 up to C18H37. The compounds described in this invention have algicidal and herbicidal effect, at the concentration of 2.10 exp(-6) mol.dm-3 and higher.

Description

Algicidal aherbicidal composition based on organic monoammonium bromine i

Technical field

The invention relates to an algicidal and herbicidal composition which contains as active ingredient organic monoammonium bromides.

BACKGROUND OF THE INVENTION

The organic monoammonium salts have an amphiphilic character, as a result of which they exhibit a wide range of effects on biological systems. As solubilizers, they are suitable for the preparation of pigment-protein complexes from photosynthetic organisms (Loach PA: in Methods in Enzymology, Vol. 69, Part C (Ed. San Pietro A.), pp. 155-172, Acad. Press New York, 1980 Hermann P., Hladik J., Sofrova, Photosynthetica 22, 411 (1988). Due to their interaction with phospholipid membranes, the structure and arrangement of these membranes are altered (Balgavý P., Gawrisch K., Frischleder H., Biophys. Biochim. Acta 772, 115, 1984; Sherer F., Leitman A., Devinsky F. , Lacko I., Balgavý P .: Gen. Physiol. Biophys. 8, 133 (1989). Organic monoammonium salts also exhibit antimicrobial activity (Devinsky F., Lacko I., Mlynarcik D., Racansky V., Krasnec L., Tenside Detergents 22, 10, 1985; Imam T., Devinsky F., Lacko I., Mlynarcik D. , Krasnec L .: Pharmazie 38, 308, 1983).

SUMMARY OF THE INVENTION

The present invention relates to a novel, hitherto unknown algicidal and herbicidal composition based on organic monoammonium bromides, characterized in that it contains as active ingredient the monoammonium bromides of the formula I, II or III

CH3

I R-N + -R1 Br *

CH3

I r2 - N + X BrR3

II

R * dl ·

OL

CON (C2H5) 2

Wherein R represents a linear or branched alkyl chain having a carbon number of 1 to 18, 2 hydroxyethyl;

R ¹ represents a linear or branched chain of CH ₃ and C _Ig H ₃ 7 C _N H 2 ₃ NH (CH _{2) 2,} C _h H 2 ₃ CONCH ₃ (CH 2) _2, CnH ^ COOCCIth, (CHahC -C-CH, QA Where n = 1, 2, 3, HOCH ₂ CH ₂ , HC = C-CH ₂ , H ₂ C = CH-CH ₂ , CÄCH-CH-C 2, CH ₃ CH = CH-CH _2, R ² is a straight or branched alkyl chain having a carbon number 2 to 14;

R ³ is a linear or branched hydrocarbon chain having a carbon number of 6 to 18, CH 2 CHCOOCH 2 X = (CH 2) _n where n = 4.5, 6 (CH 3 CH 3 hO);

R ⁴ represents a linear or branched hydrocarbon chain C 6 H 4 to C 4 H 4.

In a further study of the biological activity of the compounds of the formulas I, II and III, we have found previously unknown effects on algae (Chlorella vulgaris) and plants: maize (Zea mays L.) and vetch (Vicia sativa L.). It was found that at concentrations higher than 2. 10 ^e mol. dm ' ³ exhibit algicidal and herbicidal activity according to the invention. Compared with conventional paraquat-type herbicides and benzalkonium-type algicides, the compositions according to the invention have more advantageous faimarological effects and faster biodegradation by microorganisms found in the environment.

The following examples illustrate but do not limit the anti-allergic and herbicidal properties of the compounds of the invention according to formula I, II or III.

DETAILED DESCRIPTION OF THE INVENTION

Example 1

To test the algicidal effect of organic ammonium salts on Chlorella vulgans, they were cultured stationary at 25 ° C under a light regime of 16 hours light, 8 hours dark in Šetlík's culture medium (Šetlík I .: Annual Report of Algolog. Láb. For 1967 , 71, Trebon, 1968). The culture medium was inoculated with the exact volume of a homogeneous algae suspension and finally the test compound Ndodecyl-N-propyldimethylammonium bromide was added to the culture medium at a graduated concentration. After a 7-day cultivation, the volume of the culture medium was made up to the original volume with distilled water (equalizing the evaporation of water) and absorbance at 660 nm - proportional to the number of algal cells and chlorophyll content after extraction - was measured in the cell suspension. Ν, Ν-dimethylformamide. The total chlorophyll content of algae in the culture medium was evaluated according to the equation given in: Inskeep W.F., Bloom P.R .; Plant Physiol. 77, 263 (1985). The obtained values of these parameters were compared to the parameter values of the co-cultured control samples and evaluated as% of control. The absorbance data to determine the number of algae cells in the culture medium in the case of the algicidal action of the test compound also includes the number of dead algae that no longer contain chlorophyll.

At the concentration of N-dodecyl-N-propyldimethylammonium bromide in the culture medium:

1. 10 ' ^J mol dm' ³ is an algal chlorophyll content of 71.0 ± 2.5% of the control, an absorbance at 660 nm of 88.9 ± 2.0% of the control.

At concentration:

1.10 ⁴ mol dm ³ is the chlorophyll content of algae 0% of the control, absorbance at 660 nm 12.6 ± 1.3% of the control.

Example 2

The procedure is the same as in Example 1 except that N- (1-methyldodecyl) trimethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1.10 ' ⁵ mol dm' ³ is the algal chlorophyll content of 63.3 ± 0.5% of the control, the absorbance at 660 nm is 71.6 ± 2.1% of the control.

At concentration:

5. 10 ⁵ mol dm- ³ has an alga chlorophyll content of 16.8 ± 1.1% of the control, an absorbance at 660 nm of 41.7 ± 1.3% of the control.

EXAMPLE 1 a d 3

The procedure is the same as in Example 1 except that N-dodecyl-N- (2-propynyl) dimethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ⁵ mol of day ³ , the chlorophyll content of algae is 52.8 ± 4.0% of the control, the absorbance at 660 nm is 66.1 ± 1.2% of the control.

Example 4

The procedure is the same as in Example 1 except that N-dodecyl-N- (3-phenyl-2-propenyl) dimethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ' ⁵ mol dm' ³ is an alga chlorophyll content of 56.7 ± 5.5% of the control, an absorbance at 660 nm of 89.9 ± 13.5% of the control.

Example 5

The procedure is the same as in Example 1 except that N- (2-butenyl) -N-dodecyl-dimethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

10 * mol dm ' ³ is the content of alga chlorophyll 77.4 ± 13.4% of the control, absorbance at 660 nm 74.5 ± 3.7% of the control.

At concentration:

1.10 ' ⁵ mol dm' ³ is the content of alga chlorophyll at 1.0 ± 1.3% of the control, absorbance at 660 nm 33.8 ± 5.3% of the control.

Example 6

The procedure is the same as in Example 1 except that N-8- (benzoyoxy-3,6-dioxaoctyl) -N-octyldimephylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ' ⁴ mol dm' ³ is an algal chlorophyll content of 69.0 ± 4.1% of the control, an absorbance at 660 nm of 88.7 ± 0.5% of the control.

Example 7

The procedure is the same as in Example 1 except that N-8- (benzoyloxy-3,6-dioxaocphyl) -N-octadecyldimethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ^J mol dm ^{3 the} algal chlorophyll content is 67,5 ± 0,4% of the control, the absorbance at 660 nm is 83,4 ± 1,8% of the control.

Example 8

The procedure is the same as in Example 1 except that N-5- (benzoyloxy-3-oxapentyl) -N-dodecyldimethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

. 10 ⁶ mol dm- ³ has an algal chlorophyll content of 18.0 ± 0.3% of the control, an absorbance at 660 nm of 41.6 ± 1.5% of the control.

At concentration:

1. 10 ^{5 5} mol dm je ³ is an algal chlorophyll content of 0,8 ± 1,1% of the control, an absorbance at 660 nm of 45,3 ± 1,0% of the control.

Example 9

The procedure is the same as in Example 1 except that N-2-benzoyloxyethyl-N-dodecyldimethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

10 ^e mol dm- ³ is the algal chlorophyll content of 56,2 ± 3,2% of the control, the absorbance at 660 nm 69,7 ± 0,6% of the control.

At concentration:

1. 10 ' ⁵ mol dm ³ is the content of alga chlorophyll 9.7 ± 0.7% of control, absorbance at 660 nm 41.5 ± 0.6% of control.

Example 10

The procedure is the same as in Example 1 except that N- (p-tert-butylbenzyl) -N-dodecylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

. 10 ^e mol dm- ³ is an algal chlorophyll content of 55.0 ± 12.4% of the control, an absorbance at 660 nm of 75.9 ± 5.6% of the control.

At concentration;

1. 10 ^J mol dm- ³ is an alga chlorophyll content of 0,8 ± 1,1% of the control, an absorbance at 660 nm of 23,0 ± 0% of the control.

Example 11

The procedure is the same as in Example 1 except that N-ethyl-N-hexylpiperidine bromide was added to the culture medium.

At its concentration in the culture medium:

. 10 ' ³ mol dm' ³ is an algal chlorophyll content of 84.2 ± 4.8% of the control, an absorbance at 660 nm of 88.6 ± 0.4% of the control.

At concentration:

1. 10 ^{2 2} mol dm je ³ is algal chlorophyll content 57,0 ± 4,8% of control, absorbance at 660 nm 58,3 ± 0,8% of control.

Example 12

The procedure is the same as in Example 1 except that N-ethyl-N-hexadecylpiperidmium bromide was added to the culture medium.

At its concentration in the culture medium:

. 10 ' ⁶ mol dm' ³ is algal chlorophyll content 90.4 ± 1.3% of control, absorbance at 660 nm 93.0 ± 4.0% of control.

At concentration;

1.10 ⁵ mol dm ³ is the chlorophyll content of algae 0% of the control, the absorbance at 660 nm is 25.4 ± 0% of the control.

Example 13

The procedure is the same as in Example 1 except that N-ethyl-N-heptadecylpiperidinium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ⁵ mol dm- ³ is an algal chlorophyll content of 78.5 ± 11.8% of the control, an absorbance at 660 nm of 78.3 ± 14.4% of the control.

At concentration:

. 10 ^-3 mol dm ³ is the chlorophyll content of algae 19.7 ± 1.6% of control, absorbance at 660 nm 38.4 ± 2.9% of control.

Example 14

The procedure is the same as in Example 1 except that 4-ethyl-4-nonylniorpholinium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ' ³ mol dm ³ is algal chlorophyll content of 75.2 ± 4.3% of control, absorbance at 660 nm 61.0 ± 0.2% of control.

Example 15

The procedure is the same as in Example 1 except that 4-ethyl-4-hexadecylmorpholinium bromide was added to the culture medium.

At its concentration in the culture medium:

. 10 mol mol dm ' ³ is an algal chlorophyll content of 84.1 ± 0.6% of the control, an absorbance at 660 nm of 90.2 ± 1.3% of the control.

At concentration:

1. 10 ^{5 5} mol dm ^{3 3} is algal chlorophyll content of 14,3 ± 0,4% of control, absorbance at 660 nm 43,9 ± 4,4% of control.

Example 16

The procedure is the same as in Example 1 except that 1- (2-dodecanoyloxyethyl) -1-pentylpyrrolidinium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ^{4 4} mol dm je ³ is the algal chlorophyll content of 0% of the control, the absorbance at 660 nm is 20.1 ± 0.2% of the control.

Example 17

The procedure is the same as in Example 1 except that 1- (2-dodecanoyloxyethyl) -1-octylpyrrolidinium bromide is added to the culture medium.

At its concentration in the culture medium:

1. 10 ⁵ mol dm- ³ is the algal chlorophyll content of 50.3 ± 1.4% of the control, the absorbance at 660 nm is 58.1 ± 1.8% of the control.

Example 18

The procedure is the same as in Example 1, except that 1 N- (2-dodecanoylaminoethyl) -N-hexyldiethylammonium bromide is added to the culture medium.

At its concentration in the culture medium:

1.10 ' ⁵ mol dm' ³ is the algal chlorophyll content of 0% of the control, the absorbance at 660 nm is 16.7 ± 3.3% of the control.

Example 19

The procedure is the same as in Example 1 except that N- (2-dodecanoylmethylaminomethyl) -N-efylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ^{4 4} mol dm je ³ is algal chlorophyll content of 20,1 ± 4,4% of control, absorbance at 660 nm 50,1 ± 1,9% of control.

Example 20

The procedure is the same as in Example 1 except that N- (2-dodecanoylaminomethyl) -N-hexylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

. 10 ' ⁶ mol. dm- ³ is the chlorophyll content of algae 84.2 ± 5.0% of the control, absorbance at 660 nm 93.3 ± 4.0% of the control.

At concentration:

1. 10 ^- mol. dm ^{3 3} is the chlorophyll content of algae 0% of the control, absorbance at 660 nm 11.2 ± 0.8% of the control.

EXAMPLE 21

The procedure is the same as in Example 1 except that N- (2-dodecanoylmethylaminomethyl) -N-dodecylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ' ⁵ mol dm' ^{3 the} algal chlorophyll content is 84.1 ± 6.2% of the control, the absorbance at 660 nm is 94.8 ± 1.8% of the control.

At concentration:

. 10 ' ⁵ mol dm' ³ is the chlorophyll content of algae 0% of the control, the absorbance at 660 nm is 26.2 ± 0.1% of the control.

Example 22

The procedure is the same as in Example 1 except that N- (2-dodecanoyloxyethyl) -N-heptyldimethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1.10 ' ⁴ mol dm' ³ is the content of chlorophyll algae of 0% of the control, absorbance at 660 nm 13.0 ± 0.6% of the control.

Example 23

The procedure is the same as in Example 1 except that N- (2-dodecanoyloxyethyl) -N-benzyldimethylethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ⁴ mol dm * ³ is an algal chlorophyll content of 94.5 ± 5.0% of the control, an absorbance at 660 nm of 92.2 ± 4.1% of the control.

At concentration:

1. 10 ' ³ mol dm' ³ is the algal chlorophyll content of 0% of the control, the absorbance at 660 nm is 31.0 ± 0.6% of the control.

Example 24

The procedure is the same as in Example 1 except that 1-hexyl-3- (diethylcarbamoyl) pyridinium-imimide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ' ² mol dm * ³ is an alga chlorophyll content of 52.9 ± 3.0% of the control, an absorbance at 660 nm of 78.1 ± 14.2% of the control.

Example 25

The procedure is the same as in Example 1, except that 1-dodecyl-3- (diethylcarbamoyl) pyridinium bromide was added to the culture medium.

At its concentration in the culture medium:

1.10 ' ³ mol dm' ³ is an algal chlorophyll content of 91.0 ± 2.4% of the control, an absorbance at 660 nm of 97.5 ± 1.5% of the control.

At its concentration:

1. 10 ^{4 4} mol dm ^{3 3} is an algal chlorophyll content of 0% of the control, an absorbance at 660 nm of 20.9% of the control.

Example 26

The procedure is the same as in Example 1 except that 1-hexadecyl-3- (diethylcarbamoyl) pyridinium bromide was added to the culture medium.

At its concentration in the culture medium:

. 10 * mol dm- ³ is algal chlorophyll content of 60.2 ± 4.0% of control, absorbance at 660 nm 64.9 ± 4.5% of control.

At concentration:

1. 10 ^ies mol dm ^"3 is a chlorophyll of algae of 5.1 ± 1.3% of control, the absorbance at 660 nm, 28.3 ± 0.4% of control.

Example 27

The procedure is the same as in Example 1, except that 1-octadecyl-3- (diethylcarbamoyl) pyridinium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ' ⁵ mol dm' ³ is the algal chlorophyll content of 51.7 ± 4.3% of the control, the absorbance at 660 nm is 75.7 ± 3.1% of the control.

Example 28

The procedure is the same as in Example 1 except that N, N-di- (2-hydroxyethyl) -N-octylmethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ^{3 3} mol dm ^{3 3} is an algal chlorophyll content of 5.3% of the control, an absorbance at 660 nm of 27.5% of the control.

Example 29

The procedure is the same as in Example 1 except that N, N-di (2-hydroxyethyl) -N'-hexadecylmethylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

. 10 ^e mol dm- ³ is an algal chlorophyll content of 72.7 ± 7.1% of the control, an absorbance at 660 nm of 79.2 ± 5.0% of the control.

At concentration:

1.10 ' ⁵ mol dm' ³ is an algal chlorophyll content of 18.1 ± 3.2% of the control, an absorbance at 660 nm of 40.0 ± 4.5% of the control.

Example 30

The procedure is the same as in Example 1 except that N, N-di- (2-hydroxyethyl) -N-dodecyl-N-octylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

.10 ^'3 mol. dm ^{3 3} is the algal chlorophyll content of 0% of the control, the absorbance at 660 nm is 21.0 ± 0.4% of the control.

Example 31

The procedure is the same as in Example 1 except that N, N-di- (2-hydroxyethyl) -N-decyl-N-dodecylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

10 ' ⁶ mol dm ³ is the algal chlorophyll content of 63.9% of the control, the absorbance at 660 nm is 75.9 ± 4.1% of the control.

At concentration:

1:10 ^'3 mol ^dm3 are chlorophyll of algae 0% control, absorbance at 660 nm of 22.7% of control.

Example 32

The working procedure is the same as in Example 1 except that N, N-di- (2-hydroxyphyl) -N-dodecyl-N-octadecylammonium bromide was added to the culture medium.

At its concentration in the culture medium:

1. 10 ^{4 4} mol dm je ³ is an alga chlorophyll content of 6.1 ± 3.7% of the control, an absorbance at 660 nm of 31.3 ± 3.3% of the control.

Example 33

The herbicidal activity of organic ammonium salts was evaluated by measuring the root and stem growth of monocotyledons and dicots in maize (Zea mays L.) and vetch (Vicia sativa L.) (Murin A., Kolekova A., Vachova M., Regula S., Biology (Bratislava) 35, 937, 1980; Sekerka V., Sutoris V., Agriculture 31, 872, 1985). Test solutions of N-dodecyl-N-propyldimephylammonium bromide of graduated concentration in water were prepared in which the seeds of the plants were allowed to swell for 24 hours. The seeds were then deposited on filter paper moistened with the appropriate solutions of the test concentrations and pre-glazed for 72 hours at room temperature, with the twisted rolls of filter paper being placed in perforated polyethylene bags (ČSN 46 0610). After this time, the length of the roots and aboveground part of the plant was measured. Results were evaluated as a percentage of control.

In the application of the test solution at a concentration of 1.10 ^"4 mol dm ³ of vetch root, the length of 51.6 ± 5.4% of control, the stem length of 77.5 ± 2.6% of control.

When using a test solution of 1.10 ' ³ mol dm' ³ for the lid the root length is 4.7 ± 0.4% of the control, the stem length is 22.1 ± 2.3% of the control, for maize the root length is 19.5 ± 2.5 % of control, stem length 47.5 ± 5.6% of control.

Example 34

The procedure is the same as in Example 33 except that N- (1-methyldodecyl) trimethylammonium bromide was used to prepare the test solutions.

When a test solution of concentration 1 is applied. 10 ^ó mol dm ^{3 3} for the lid, the root length is 5.5 ± 0.2% of the control, the stem length is 3.0 ± 0.1% of the control, for maize the root length is 14.0 ± 2.9% of control, stem length 49.5 ± 0.4% of control.

Example 35

The procedure is the same as in Example 33 except that N-dodecyl-N- (2-propynyl) dimethylammonium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ' ³ mol dm' ³ for the lid, the root length is 4.0 ± 0.7% of the control, the stem length is 31.2 ± 0.4% of the control, for maize the root length is 23.5 ± 3.0% of control, stem length 48.7 ± 0.1% of control.

Example 36

The procedure as in Example 33 except that Ndodecyl-N- (3-phenyl-2-propenyl) dimethylammonium bromide was used to prepare the test solutions.

When using a test solution of 1.10 ' ³ mol dm' ³ for the lid, the root length is 33.9 ± 4.9% of the control, the stem length is 55.0 ± 5.1% of the control, for maize the root length is 80.0 ± 2.8 % of control, stem length 81.3 ± 2.9%.

When applying a test solution of concentration 2. The 10 ' ⁴ mol dm' ³ of the lid is the root length of 70.7% of the control.

Example 37

The procedure as in Example 33 except that N- (2-butenyl) -N-dodecyldimethylammonium bromide was used to prepare the test solutions.

When using a test solution with a concentration of 1.1 O * ³ mol dm ^-3 for the root, the root length is 5.6 ± 0.3% of the control, the stem length is 50.6 ± 4.6% of the control, for corn the root length is 41.2 ± 3.4% control, stem length 63.5 ± 0.5% control.

Example 38

The procedure of Example 33 was followed except that N-8 (benzoyloxy-3,6-dioxaoctyl) -N-octyldimethylammonium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ' ³ mol dm' ³ for the lid, the root length is 81.2 ± 0.2% of the control, the stem length is 89.1 ± 1.1% of the control, for maize the root length is 56.7 ± 2%. 9% control, stem length 69.1 ± 2.1% control.

Example 39

The procedure as in Example 33 was followed except that N-8 (benzoyloxy-3,6-dioxaoctyl) -N-octadodecylammonium bromide was used to prepare the test solutions.

When applying the test solution at a concentration of. 10 ' ³ mol dm' ³ for the lid, the root length is 73.0 ± 5.0% of the control, the stem length 60.8 ± 0.5% of the control.

Example 40

The procedure of Example 33 was followed except that N-5 (benzoyloxy-3-oxapentyl) -N-dodecyldimethylammonium bromide was used to prepare the test solutions.

When applying test solution 1. 10 ' ³ mol dm' ³ for the lid the root length is 28.0 ± 0.6% of the control, the stem length is 75.5 ± 1.2% of the control, for maize the root length is 57.3 ± 0 2% of control, stem length 68.1 ± 2.2% of control.

Example 41

The procedure as in Example 33 except that Ν-2-benzoyloxyethyl N-dodecyldimethyl ammonium bromide was used to prepare the solutions.

When applying the test solution 1.10 ' ³ mol dm' ³ for the lid, the root length is 15.3 ± 0.9% of the control, the stem length is 72.0 ± 1.8% of the control, for maize the root length is 50.9 ± 3.5 % of control, stem length 72.7 ± 2.5% of control.

Example 42

The procedure as in Example 33 except that N- (tert-butylbenzyl) -N-dodecyldimethylammonium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ' ³ mol dm' ³ for the lid, the root length is 20.0 ± 1.7% of the control, the stem length is 67.7 ± 1.1% of the control, for maize the root length is 42.2 ± 4.3% of control, stem length 71.3 ± 1.2% of control.

When applying the test solution at a concentration of. 10 ' ⁴ mol dm' ³ for the lid, the root length is 69.8 ± 3.0% of the control, the stem length 84.7 ± 1.0% of the control.

Example 43

The procedure as in Example 33, except that N-ethyl N-hexylpiperidinium bromide was used to prepare the test solutions.

For a test solution with a concentration of 1.10 ' ³ mol dm' ³ for the lid the root length is 65.5 ± 7.1% of the control, the stem length is 37.4 ± 3.2% of the control, for maize the root length is 71.5 ± 2% 2% of control, stem length 84.5 ± 2.4% of control.

Example 44

The procedure as in Example 33, except that N-ethyl N-decylpiperidinium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ³ mol. dm ' ³ for the lid, the root length is 10.2 ± 1.8% of the control, the stem length is 12.7 ± 2.0% of the control, for maize the root length is 29.9 ± 1.2% of the control, the stem length is 66.1 ± 2.7% of control.

Example 45

The procedure as in Example 33, except that N-ethyl N-heptadecylpiperidinium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ' ³ mol dm' ³ for the lid the root length is 63.1 ± 2.2% of the control, the stem length is 53.4 ± 2.2% of the control, for maize the root length is 77.1 ± 3.5% of control, stem length 82.3 ± 0.7% of control.

Example 46

The procedure of Example 33 was followed except that 4-ethyl-1-4-nonylmorpholinium bromide was used to prepare the test solutions.

When using a test solution with a concentration of 1.10 ' ³ mol dm' ³ for the lid, the root length is 22.0 ± 1.7% of the control, the stem length is 26.0 ± 3.0% of the control, for maize the root length is 18.6 ± 0.3 % of control, stem length 59.8 ± 0.1% of control.

Example 47

The procedure as in Example 33, except that 4-ethyl-4-hexadecylmorpholinium bromide was used to prepare the test solutions.

When a test solution with a concentration of 1. 10 ³ mol dm ^{3 is applied} to the lid, the root length is 63.5 ± 7.5% of the control, the stem length 76.6 ± 8.8% of the control.

Example 48

The procedure as in Example 33 except that 1- (2-dodecanoyloxyethyl) -1-pentylpyrrolidinium bromide was used to prepare the test solutions.

When applying the test solution at a concentration of. 10 ' ³ mol dm' ³ for the lid, the root length is 51.7 ± 3.9% of the control, the stem length 69.3 ± 1.1% of the control.

Example 49

The procedure as in Example 33 was followed except that 1- (2-dodecanoyloxyethyl) -1-octylpyrrolidinium bromide was used to prepare the test solutions.

When using a test solution with a concentration of 1.10 ' ³ mol dm' ³ for the lid, the root length is 44.8 ± 5.4% of the control, the stem length is 79.4 ± 2.7% of the control, for maize the root length is 48.1 ± 3%. 0% control, stem length 78.5 ± 0.7% control.

When applying the test solution at a concentration of. The 10 * mol dm- ³ of the lid is the root length of 86.7 ± 0.7% of the control.

Example 50

The procedure as in Example 33 except that test solutions were used to prepare test solutions. N- (2dodekanoylamimoetyl) -N-hexyldimetylamóniumbromid.

For a test solution with a concentration of 1.10 ' ³ mol dm' ³ for the lid the root length is 12.8 ± 2.1% of the control, the stem length is 64.2 ± 6.5% of the control, for maize the root length is 52.0 ± 5% 6% control, stem length 70.3 ± 0.2% control.

Example 51

The procedure as in Example 33 except that N- (2-dodecanoylmethylaminomethyl) -N-ethylammonium bromide was used to prepare the test solutions.

When using a test solution of 1.10 ' ³ mol dm' ³ for the lid, the root length is 66.9 ± 1.1% of the control, the stem length is 83.8 ± 0.1% of the control, for maize the root length is 59.0 ± 2.4% % of control, stem length 68.5 ± 1.8% of control.

Example 52

The procedure as in Example 33 except that N - (- 2-dodecanoylmethylaminomethyl) -N-hexylammonium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ³ mol dm ³ for the lid, the root length is 10.0 ± 0.9% of the control, the stem length is 51.9 ± 6.6% of the control, for maize the root length is 39.6 ± 3.5% control, stem length 65.0 ± 1.4% control.

When a test solution with a concentration of 1 × 10 ^-4 mol dm ^{-3 is applied} to the lid, the root length is 77.6 ± 3.1% of the control, the stem length is 85.2 ± 0.7% of the control.

Example 53

The procedure of Example 33 was followed except that N- (2-dodecanoylmethylaminomethyl) -N-dodecylannionibromide was used to prepare the test solutions.

When applying the test solution at a concentration of. 10 ' ³ mol dm' ³ for the lid, the root length is 88.5 ± 4.1% of the control, the stem length 61.4 ± 3.5% of the control.

Example 54

The procedure of Example 33 was followed except that N- (2-dodecanoyloxyethyl) -N-heptyldimethylammonium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ' ³ mol dm' ³ for the lid the root length is 65.8 ± 2.2% of the control, the stem length is 85.9 ± 3.4% of the control, for maize the root length is 79.0 ± 2.9% of control, stem length 88.1 ± 4.3% of control.

Example 55

The procedure of Example 33 was followed except that N- (2-dodecanoyloxyethyl) -N-benzyldimethylammonium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ' ³ mol dm' ³ for the lid, the root length is 81.9 ± 0.2% of the control, for maize the root length is 84.3 ± 0.5% of the control, the stem length is 83.1 ± 3.1% of control.

Example 56

The procedure as in Example 33 except that 1-hexyl-3- (diethylcarbamoyl) -pyridine bromide was used to prepare the test solutions.

When applying the test solution at a concentration of. 10 ^-3 mol dm ³ of vetch root, the length of 67.2 ± 0.8% of control, the stem length of 87.8 ± 2.5% of control, the administration of the test solution at a concentration of 1 10 ^-3 mol dm ³ of the vetches root length 87.2 ± 0.2% of control, stem length 89.1 ± 0.6% of control.

Example 57

The procedure as in Example 33 except that 1-dodecyl-3- (diethylcarbamoyl) pyridinium bromide was used to prepare the test solutions.

When applying test solution 1. 10 ' ³ mol dm' ³ for the lid the root length is 71.4 ± 0.8% of the control, the stem length is 79.9 ± 0.1% of the control, for maize the root length is 74.4 ± 4% 2% of control, stem length 75.5 ± 2.2% of control.

Example 58

The procedure as in Example 33, except that 1-hexadecyl-3- (diethylcarbamoyl) pyridinium bromide was used to prepare the test solutions. For a test solution concentration of 8. 10 ' ⁴ mol dm' ³ , the root length is 76.3 ± 0.7% of the control, the stem length is 81.1 ± 3.2% of the control

Example 59

The procedure as in Example 33 except that 1-octadecyl-3- (diethylcarbamoyl) pyridinium bromide was used to prepare the test solutions.

When applying the test solution at a concentration of. 10 ' ³ mol dm' ³ at the top, the root length is 67.4 ± 8.4% of the control, the stem length 52.3 ± 3.6% of the control, when applying a test solution with a concentration of 1. 10 ' ³ mol dm' ³ u For maize, the root length is 84.1 ± 3.4% of the control.

Example 60

The procedure as in Example 33 except that N, N-di (2-hydroxyethyl) -N-octylniethylemmonium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ^-3 mol dm ^-3 for maize, the root length is 40.2 ± 3.2% of the control, the stem length is 84.8 ± 1.5% of the control.

Example 61

The procedure as in Example 33, except that N, Ndi (2-hydroxyethyl) -N-tetradecylmethylaminobromide was used to prepare the test solutions.

When applying the test solution at a concentration of. 10 ' ⁴ mol dm' ³ for the lid, the root length is 66.5 ± 2.5% of the control, the stem length 84.3 ± 3.3% of the control.

When applying test solution 1. 10 ' ³ mol dm' ³ in maize, the root length is 65.0 ± 4.3% of control, stem length 88.0 ± 1.8% of control.

Example 62

The procedure as in Example 33, except that N, N-di (2-hydroxyethyl) -N-hexadecylmethylammonium bromide was used to prepare the test solutions.

When applying the test solution 1. 10 ' ³ mol dm' ³ for the lid, the root length is 73.7 ± 1.1% of the control.

Example 63

The procedure as in Example 33, except that N, N-di (2-hydroxyethyl) -N-dodecyl-N-octylammonium bromide was used to prepare the test solutions.

When applying a test solution with a concentration of 1. 10 ' ³ mol dm' ³ for maize, the root length is 79.3 ± 3.6% of the control, the stem length is 84.4 ± 2.0% of the control, for the lid the root length is 70.5 ± 0.3% of control.

Example 64

The procedure as in Example 33, except that N, N-di (2-hydroxyethyl) -N-decyl-N-dodecylammonium bromide was used to prepare the test solutions.

When applying a test solution of concentration 1. 10 ' ³ mol dm' ³ for the lid, the root length is 81.1 ±

1.8% control.

Example 65

The procedure as in Example 33 except that N, N-di (2-hydroxyethyl) -N-dodecyl-N-octadecylammonium bromide was used to prepare the test solutions.

When a test solution with a concentration of 1. 10 ^-3 mol dm ^{-3 is applied} to the lid, the root length is 56.5 ± 0.7% of the control, the stem length is 86.0 ± 0.1% of the control.

Example 66

The organic monoammonium bromides of the invention inhibit the efficacy of the photosynthetic apparatus of the photosynthetic organisms. This is documented by results obtained by the electron paramagnetic resonance (EPR) method. In plant chloroplasts at room temperature in the dark, a signal in the region of g = 2, which is composed of two signals, can be observed: a signal I at g = 2.0026 and s ΔΒ = 0.72 mT belonging to the photosynthetic center of PS I, in particular the cation radical of the chlorophyll dimer a; 2) it is called. signal II at g = 2.0045 and s ΔΒ = 2 mT belonging to the semichinone cation radical of the donor side of the photosynthetic center PS II.

Illumination of chloroplasts in the measuring cavity of the EPR spectrometer increases signal intensity I and II in healthy, untreated chloroplasts by 1.5 to 2-fold. When the electron flux from photosystem II to photosystem I is disrupted, the ratio of the EPR signals of the photosystem measured in the light and in the dark increases. Comparing the values of this ratio for the samples treated with the compounds of the invention and the control samples gives an indication of the degree of inhibition of the photosystem II (referred to as parameter P).

The EPR signal intensity is measured in a preparation of chloroplasts obtained from green leaves of spinach after homogenization in TRIS buffer at pH 7.0 (with the addition of sucrose, potassium and magnesium chloride), followed by filtration and centrifugation. All operations are performed with cooling at 0 to 4 ° C. The chloroplast sediment is suspended in the above buffer so that the measurement samples contain 4 to 5 mg of chlorophyll.

Instrument parameters and measurement: ERS-230 (WG, AdW Berlin, East Germany; measurement is performed at 25 ° C at 5 mW with 5 mW modulation. 10 ' ⁴ T. The instrument operates in the X band, ie the microwave frequency is The organic monoammonium bromides studied are added to the chloroplasts just prior to measurement to a final concentration of 5.10 ^-2 mol dm ^-3 .

The P-values of the compounds of the invention, which is a measure of the inhibition of the photosystem Π, are shown in Table 1. The higher the P-value, the greater the inhibition.

Industrial usability

The compounds of the invention act algicidal aherbicidal at concentrations of 2.6. Go ⁶ mol dm ³ and higher and can be used alone or in admixture with other substances as an active ingredient of anti-toxic and herbicidal preparations

Table 1

The P-values of the compounds of the invention, which express the degree of inhibition of photosystem II.

compound

Parameter P

N-dodecyl-N-propyldimetylamóniumbromid18,27

N- (l-metyldodecyl) trimetylamóniumbromid39,24

N-dodecyl-N- (2-propynyl) dimetylamóniumbroinid21,16

N-dodecyl-N- (3-phenyl-2-propenyl) dimetylamóniumbromid16,00

N- (2-butenyl) -N-dodecyldimetylamóniumbromid15,80

N-8- (benzoyloxy-3,6-dioxaoctyl) -N-oktyldimetylamóniumbromid18,60

N-8- (benzoyloxy-3,6-dioxaoctyl) -N-oktadecyldimetylamóniiunbromid12,00

N-5- (benzoyloxy-3-oxapentyl) -N-dodecyldimetylamóniumbromid14,18

N-benzoyloxyethyl-N-dodecyldimetylamóniumbromid15,68

N- (p-tert-butylbenzyl) -N-dodecylamóniuinbromid20,96

N-ethyl-N-hexylpiperidíniumbiOinid1,36

N-ethyl-N-hexadecylpiperidíniumbromid9,44

N-ethyl-N-heptadecylpiperidinium bromide18,18

4-ethyl-4-nonylmorfolíniumbromid13,85

4-ethyl-4-hexadecylmorpholinebromide 24,73 1- (2-dodecanoyloxyethyl) -1-pentylpyrrolidinium bromide 20,00 1- (2-dodecanoyloxyethyl) -1-octylpyrrolidinium bromide15,91

N- (2-dodekanoylaminoetyl) -N-hexyldimetylamóniuinbromid18,46

N- (2-dodekanoylmetylaminometyl) -N-etylamóniumbromid6,92

N- (2-dodekanoylmetylaminometyl) -N-hexylamóniumbromid18,27

N- (2-dodecanoylmethylaminomethyl) -N-dodecylammonium bromide 10,00

N- (2-dodekanoyloxyety]) - N-heptyldimetylamóniumbromniid16,91

N- (2-dodecanoyloxyethyl) -N-benzyldimethylannionium bromide12,42 1-hexyl-3- (diethylcarbamoyl) pyridinium bromide 1,41-dodecyl-3- (diethylcarbamoyl) pyridinium bromide28,60

1-Hexadecyl-3- (diethylcarbamoyl) pyridinium bromide 18.85 1-octadecyl-3- (diethylcarbamoyl) pyridinium bromide17.07

N, N-di- (2-hydroxyethyl) -N-tetradecylmetylamóninmbromid16,83

N, N-di- (2-hydroxyethyl) -N-hexadecylmetylamóniumbromid15,58

N, N-di- (2-hydroxyethyl) -N-dodecyl-N-oktylamóniumbromid6,81

N, N-di- (2-hydroxyethyl) -N-dodecyl-N-dodecyIamóniumbromid5,06

N, N-di- (2-hydroxyethyl) -N-dodecyl-N-octadecylammonium bromide 2,42 * P (Lvetlo: Itma) samples: (tvetio: Itma) controls

Claims (1)

PATENT CLAIMS Algicidal and herbicidal composition based on organic monoammonium bromides / characterized in that it contains, as active ingredient, the monoammonium bromides of the formula I, II or III CH3 1 R - N + - R1 Br r2-N + ^ XBr- I ♦ ch ₃ R3 « I Π R4 ^L ^^ ε0Ν (02-5) 2 Wherein R is a linear or branched alkyl chain having a carbon number of 1 to 18, 2-hydroxyethyl; ^R1 is a straight or branched chain CH ₃ to C ₈ H _37, CnH23NH (CH ₂₎ 2, C _n H 2 ₃ CONCH ₃ (CH 2) 2 CNH 2 ₃ COO (CH 2) 2, (CH _{3) 3} CC ₆ H 4 CH ₂ , C ₆ CH 3, CeH ₅ CO (OCH ₂ CH ₂ ) _n where n = 1, 2, 3, HOCH ₂ CH 3, HC = C-CH ₂ , H ₂ C = CH-CH 2, C ₆ H <CH = CH- CH ₂ , CH ₃ CH = CH-CH 3, R ³ is a linear or branched alkyl chain having 2 to 14 carbon atoms; * R ³ is a linear or branched hydrocarbon chain having from 6 to 18 carbon atoms, Cn = COOCCH 2, X = (CH ₂ ) _n where n = 4.5, 6 (CH ₂ CH ₂ ) ₂ O; ^Λ R ⁴ represents a linear or branched hydrocarbon chain of C 1 H 3 to C ₁₈ H ₃₇ .