Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/02—Amines; Quaternary ammonium compounds
  • A01N33/12—Quaternary ammonium compounds

Definitions

• the invention is concerned with compounds which have been found to be highly effective in controlling the growth of algae and with the use of such compounds.
• the compounds which are employed in the practice of the invention have the formula in which the symbol R represents an aliphatic hydrocarbon residue or a cycloaliphatic-aliphatic hydrocarbon residue containing from 10 to 15 carbon atoms; the symbol R represents hydrogen or a lower alkyl radical; the symbols R represents hydrogen or a lower alkyl radical; the symbol R represents an aliphatic hydrocarbon residue or a cycloaliphatic-aliphatic hydrocarbon residue containing from 10 to 15 carbon atoms; the symbol R represents a straight or branched chain alkylene residue having from 2 to carbon atoms; with the proviso that the residues represented by the symbols R and R taken with the alkylene residue represented by the symbol R provide a total of at least 27 carbon atoms.
• Acid addition salts of the Formula I compounds, as well as quaternary products produced therefrom, are also suitable for use in the practice of this invention.
• the present invention provides a means for effectively controlling the growth of algae.
• the compounds which are used in the practice of the invention have been found to possess a high degree of activity against algae growth, and in use, their effectiveness is long-lasting.
• the algae growth controlling agent there is employed, as the algae growth controlling agent, at least one diamine having the formula 2 Rs 1 in which the symbol R represents an aliphatic hydrocarbon residue or a cycloaliphtic-aliphatic hydrocarbon residue containing from 10 to carbon atoms; the symbol R represents hydrogen or lower alkyl radical; the symbol R represents hydrogen or a lower alkyl radical; the symbol R represents an aliphatic hydrocarbon residue or a cycloaliphatic-aliphatic hydrocarbon residue containing from 10 to 15 carbon atoms; the symbol R represents a straight or branched chain alkylene residue having from 2 to 10 carbon atoms; with the proviso that the residues represented by the symbols R and R taken with the alkylene residue represented by the symbol R provide a total of at least 27 carbon atoms, or an acid addition salt of, or a quaternary product produced from, a Formula I compound.
• the symbols R and R taken with the alkylene residue represented by the symbol R provide a total of at least 27 carbon atom
• Preferred classes of compounds which fall within the scope of Formula I are those in which the symbol R and R each represent a 1,5,9-dimethyl-decyl residue, or the corresponding residue unsaturated in the 2,3-, 4,5- and/or 8,9-position; or in which the symbols R and R each represent a 1-methyl-3-(2,6,G-trimethylcyclohexyl)- propyl radical; or in which the symbols R and R each represent a 1 methyl-3-[2,6,6-trimethylcyclohexen-(1)- yl]-propyl residue.
• Such compounds preferably have, as
• R and R substituents a hydrogen atom or an alkyl radical having from 1 to 3 carbon atoms, especially a methyl radical.
• R represents a straight chain alkylene residue
• such residue contains preferably from about 4 to 6 carbon atoms, especially, 6 carbon atom
• R represents a branched chain residue
• such residue contains, preferably, from about 7 to 10 carbon atoms, especially 9 carbon atoms.
• the present invention embraces the use of diamines having the formula in which the symbol R and R represent a hydrogen atom or a methyl group; and R represents a polymethylene chain, which may be methyl-substituted, having from 2 to 10, and preferably from 6 to 9, carbon atoms, and wherein double bonds indicated by the broken line can be hydrogenated.
• Acid addition salts of, and quaternary products derived from, the Formula 1(a) compounds are also suitable for use.
• Representative of a preferred class of compounds, embraced by Formula 1(a) are those in which the symbol R represents hexamethylene or a trimethyl hexamethylene group, such as, the 2,2-dimethyl-4-methylhexamethylene and the 2-methyl-4,4-dimethyl-hexamethylene radicals.
• Specific examples of certain Formula 1(a) compounds are as follows:
• N,N'-bis-(1,5,9-trimethyldecyl) 2,2-dimethyl-4-methyl-1,6-hexanediamine and N,N' bis-(1,5,9-trimethyldecyl) Z-methyl 4,4-dimethyl 1,6-hexanediamine is used.
• the invention involves the use of a mixture of N,N'-bis-(l-methyl-3- [2,6,6-trimethylcyclohexyl] propyl) 2, dimethyl-4- methyl-1,6-hexanediamine and N,N'-bis (l-methyl)-3 [2,6,6-trimethylcyclohexyl] propyl) 2-methyl 4,4-dimethyl-1,6-hexanediamine.
• the present invention contemplates the use of diamine bases of Formulas I, 1(a) and I(b) as well as acid addition salts thereof and quaternary products derived therefrom.
• Suitable for use are salts of the compounds of Formulas I, 1(a) and I(b) with organic acids, such as, acetic acid; benzoic acid; citric acid; malic acid; maleic acid; salicylic acid; tartaric acid; etc. or with mineral acids, such as, the hydrohalic acids, for example, hydrochloric acid; nitric acid; phosphoric acid; sulfuric acid; etc.
• salts of the compounds with methane sulfonic acid can be used.
• quaternary compounds produced from the compounds of Formulas I, 1(a) and I(b) can be employed. These quaternary compounds are produced, for example, by treating the base with an alkyl halide, such as, methyl bromide, or with an alkyl sulfonate, such as, dimethyl sulfate.
• an alkyl halide such as, methyl bromide
• an alkyl sulfonate such as, dimethyl sulfate.
• the compounds of Formulas I are used to prevent or at least retard the growth of algae.
• the compounds described herein act to inhibit algae growth.
• the compounds will retard the growth of algae.
• the quantity of active ingredient which, in any given case, is added to the medium to be treated will determine, to a great extent, the frequency with which the treatment is repeated.
• the compounds of Formulas I, 1(a) and I( b) are used in the practice of this invention to prevent and/or inhibit the growth of algae will be readily apparent to persons skilled in the art.
• the compounds can be formulated as solutions or emulsions and used as such.
• the compounds can be formulated as emulsifiable concentrates, such concentrates being converted into emulsions prior to use.
• the bases of Formulas I, 1(a) and I(b) after having been converted into water-soluble acid addition salts, for example, into an acetate salt, a hydrochloride salt or a sulfate salt, can be incorporated into a permeable vessel, for example, a cloth bag.
• Such bag can be aflixed to a water hose in such a manner that the water leaving the hose flows through the bag into the tank or pool which is to be protected against algae growth.
• the water-soluble salts become dissolved in the water and are distributed throughout the tank or pool by the flow of the water therein.
• the compound of Formulas I, I(a) or I(b), or a mixture thereof, in the form of a water-soluble salt can be introduced onto the filter layer. As the water flows through the filter, the active ingredient becomes dissolved therein.
• such concentrates can be produced, for example, by reacting the Formulas I, I(a) or I(b) base with a quantity of acid, for example, acetic acid, slightly in excess of that theoretically required for salt formation and adding such salt to water.
• a quantity of acid for example, acetic acid
• an emulsifiable concentrate can be obtained by treating the Formulas I, I(a) or I(b) compounds with a quantity of a suitable emulsifier which is sufficient to emulsify the compound when mixed with water.
• Example 1 In this example, 500 ml. of concentrated (95100%) acetic acid was added to, and stirred in, 9.5 liters of Water. Thereafter, 2.5 kg. of N,N'-bis-(1-methyl-3-[2,6,6 trimethylcyclohexyl] -propyl 1 ,6-hexanediamine was added to the aqueous acetic acid solution. The product, thus obtained, was in the form of a clear concentrate capable of being diluted further with water.
• Example 2 A concentrate was produced, in the manner described in Example 1 using, with but one exception, the same ingredients and the same quantities thereof as were used in Example 1.
• the 2.5 kg. of N,N'-bis- (1-rnethyl-3-[2,6,6 trimethylcyclohexyl] propyl) 1,6- hexanediamine used in Example 1 was replaced with 2.5 kg. of a mixture comprising equal amounts of N,N'-bis- (1,5,9 trimethyldecyl) 2,2 dimethyl 4-methyl-1,6- hexanediamine and N,N-bis-(1,5,9 trimethyldecyl) 2- methyl-4,4-dimethyl-1,6-hexanediamine.
• Example 3 A concentrate was produced, in the manner described in Example 1, using, with but one exception, the same ingredients and the same quantities thereof as were employed in Example 1. In producing the concentrate of this example, however, there was used 2.5 kg. of a mixture of equal quantities of N,N-bis-(1-methyl-3-[2,6,6-trimethylcyclohexyl] -propyl) 2,2-dimethyl-4-methyl-1,6-hexanediamine and N,N'-bis-(1 methyl-3-[2,6,6-trimethylcyclohexYlJ-propyl) -2-methyl-4,4-methyl-1,6-hexanediamine in place of the 2.5 kg. of N,N-bis-(1-methyl-3-[2,6,6-trimethylcyclohexylJ-propyl) 1,6-hexanediamine employed in Example 1.
• Example 4 In this example, 250 grams of N,N'-bis-(1-methyl-3- [2,6,6 trimethylcyclohexyl]-propyl)-1,6-hexanediamine dihydrochloride was incorporated into a tightly woven cotton sack. This sack was affixed to the water inlet orifice of a tank. The tap was opened and water was allowed to flow in a rapid stream through the cloth sack into the tank. The active ingredient was thus carried into the tank, dissolved in the tank water. The tank was then filled to a capacity of 50 cubic meters of water.
• Example 5 In this example, 250 grams of N,N-bis-( 1,5 ,9-trimethyldecyl) 1,6 hexanediamine dihydrochloride were introduced into a swimming pool, equipped with a rotary pump and filter installation, having the dimensions of 4 meters x 7 meters. The pool was filled with water to the depth of 1.8 meters. The active ingredient was incorporated into. the system by adding it to the circulating water prior to the passage of the water through the filter. The active ingredient became dissolved in the water.
• Example 6 there was used a glass aquarium containing about 10 liters of water. The water in this aquarium, kept in constant motion by the continuous passage of air, was maintained at a temperature within the range of about 20 to about 25 C. This aquarium was lit with a mercury vapor lamp. There was added thereto N,N-bis- (1 methyl 3-[2,6,6-trimethylcyclohexyl]-propyl)-1,6- hexanediamine at a level of 2 parts per million parts of water.
• a second aquarium was set up, identical to that described in the preceding paragraph, containing the same active ingredient but at a level of 2.5 parts per million rather than the 2.0 parts per million mentioned heretofore. Furthermore, nine additional glass aquaria were set up to evaluate eight other compounds, identified in the table which follows, at the concentration indicated therein.
• N,N-bis-(1,5,9-trirnethyldecyl)- N,N-dimethyl-1.2-ethylendiamine 2. 5 0-20 (5) N,N-bis-(1,5,9-trimethyldecyl)- N,N-dimethy1-l,6-hexanediamine- 2 0 020 (6) N,Nbis-(l-methyl-3-[2.6.6-trimethylcyclohexyl]-propy1)-N,N- dirnethyl-l,4-butane-diamine bis- (methoehloride) 2.
• Process for the control of algae growth in an aqueous system which comprises adding to said aqueous system an effective amount of at least one compound selected from the group consisting of (1) N,N'-bis-(1,5,9-trimethyldecyl) 1,6 hexanediamine, N,N-bis-(1,5,9-trimethyldecyl) 1,2 ethylenediamine, N,N'-bis-(1,5,9-trimethyldecyl)-N,N'-dimethyl 1,2 ethylenediamine, N,N-bis- (1,5,9 trimethyldecyl) N,N dimethyl-1,6-hexanediamine, N,N' bis (1 methyl 3-[2,6,6-trimethylcyclm hexyl] propyl) 1,6 hexanediamine, N,N'-bis-(1-methyl 3 [2,6,6-trimethy1cyclohexyl]-propyl)-N,N-dimeth yl 1,4 butanediamine bis-(met

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• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
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• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Cited By (12)

Citations (2)

• 1966
  • 1966-02-25 CH CH278966A patent/CH481569A/de not_active IP Right Cessation
• 1967
  • 1967-02-07 US US614403A patent/US3466162A/en not_active Expired - Lifetime
  • 1967-02-17 NL NL6702404A patent/NL6702404A/xx unknown
  • 1967-02-17 FR FR95302A patent/FR1511855A/fr not_active Expired
  • 1967-02-20 BE BE694294D patent/BE694294A/xx unknown
  • 1967-02-24 BR BR187276/67A patent/BR6787276D0/pt unknown
  • 1967-02-24 ES ES337254A patent/ES337254A1/es not_active Expired

Patent Citations (2)

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