DE2034642A1 - Bactericide and algae - Google Patents

Description

The invention relates to a bactericide and algixid, that by a content of at least one N-Tetrahalogenäthylthiocarboxamid the general formula

OH R - C - N - 3 - R ¹

in which R is a hydrogen atom or an alkyl radical with 1 to 2 carbon atoms and H ^{1 is} a letrahalogenethyl radical, in which the halogens have an atomic number of 17 to 35, as active ingredient.

In US Pat. No. 3,344,153, If-tetra chloroethyltmocarboxamides are used called,: but no effect - | examples of such connections are given. The in this pa-

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data listed in the text »algae that aromatic and heterocyclic N-fluoromethyltmocarboxamides a fungi cide and have miticidal effects.

Bs - has now been found to be a selected group the above formula described in the patent 3 344 153 Gar »boxamide unusual bactericidal and have algicidal properties.

Preferred compounds of this * group are those in which R ^{1 is} a tetrachloroethyl radical, in particular a 1,1,2,2-tetrachloroethyl radical.

Typical examples of H-Tetrahalogenäthylthio carboxamides of the above formula are: N-1,1,2,2- * Tetrachloräthylthioformainid * N-1,1,2, .2-Tetrachloräthylthioformamid, N ^ -Brom-ll ^ -trichiLoräthylthioformamid, 1, 1,2,2-Tetrabromoethylthioformamid, N-1,1,2, -2-Tetraehloräthylthioacetamid, N-1 , 2,2,2-Tetrachloräthylthioacetamid, Nl ^^^ - Tetrabromäthylthioacetamid, Nl, 2-iJibr <om-2, 2-dichloroethylthioacetamide and Nl, l, 2-tribromo-2-chloroethylthioacetamide.

Me carboxamides of the formula above can be obtained by condensing a primary carboxamide with a Tetrahaloäthylsulfenylhalogenid, usually a Tetra haloäthylsulfenylchlorid produce. This reaction can be represented by the following chemical (K) calibration:

O OH

ti ir i

RC-NB ^ + R'-SX ■ - * RC-jr-SR ¹ + HX

in which Ä and H ¹ di »have the meanings given above and χ is a chlorine or broaatoa.

It is twofold that this reaction should be carried out in the presence of an inert solution such as OJLwetayleulfoxide, dimethylformamide, acetonitrile, dioxane or methylene chloride. The reaction temperature is generally not critical and is usually in the range from about -20 to 50.degree. C., preferably between about 0 and 20.degree. Likewise, the pressure is not critical and is usually atmospheric pressure or autogenous pressure. It is expedient to use stoichi © metric amounts of the reactants or a small amount of the carbonamides.

It was found * that the above-described benen N-TetrahaLoäthylthiocarDoxaffiicte plant patnogens. Fight bacteria and α, «en when in bactericidal or algiJEiaen amounts applied to these organisms who the. They are particularly effective in combating bacteria and algae, industrial drains and cooling washes strönie, such as those used in the paper and food industries occur and contaminate other bodies of water such as lakes, ponds, rivers or the like. When these compounds ssur combat bacteria and al ^ en are used in such waters, will (werαen) one or more carboxamides egg in the formula above added to a kenge that inhibits the growth of these organisms. In water they are usually used in concentrations of about Oil to 50 ppm. Will you Mainly used to combat algae, they are usually used in concentrations of around 0.1 to 10 ppm used, which is about 1 to 100 kg / ha of water surface at 1 m

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Depth corresponds to that of the Garböxattiide tiles in the environment · such bacteria and algae as dispersible powder, concentrates emulsifiable in water or in solution in water-miscible solvents, trains set.

Typical solid supports, 'those used to poittml these Carboxamides that can be used are ion, talc, chalk and sawdust, typical solvents are aromatic Hydrocarbons such as xylene, benzene., .. toluene, petroleum fractions » Alcohols (especially low-molecular alkanols) and chlorinated aliphatic hydrocarbons such as ghloroi'orn or methylene chloride. These formulations can also contain emulsifiers, adhesives, fillers and other compatible pesticides.

The following examples are provided for explanation the invention. The percentages relate to that Weight,

Example It

yI ^^ - ietrachioräthylthioformamla.

20 e forxamla around 10 ml of Ilime-snyl formamide beads mixed in a vessel cooled in an ice bath. This Gemiscn wurae slowly with 20 gl »l, was added 2 (.2-Tetrachloräthylaulfenylehlorid. Hach beenieter addition was taken from the vessel and remained the Sisbaa Ib hours at gebungstemperatur to stand. Anschließena were 500 ml ice" Aaser brought into the (Jefäi and the mixture with twice

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.; .. ■■; .; ■, ■ ■, _ 5 ->"^■;■■" ■ \ v _:. \ \

200 ml of ethyl ether extracted. The ether extracts were washed with saturated sodium chloride solution and dried over magnesium sulfate. After drying it was Ether stripped off and the substance from a benzene / hexane mixture recrystallizedx. 7 g of H-1,1,2,2-Tetraehlorätnylthioformamid were obtain. This solid bond melted at 40-45 C. The sulfur and chlorine analyzes resulted in the following values:

Calculated S. Ip * 18% ■; . Cl 58 , 4 Found: rf 12th ,8th ; Cl 57 , 6 Example 2:

The ΕΓ-1,1,2,2-Ietrachloräthylthioacetamid -wurde after the general procedure described in Example 1. This compound, also as a solid was present, melted at 89-92 ° C. The sulfur and chlorine analysis resulted in the following values:

Calculated S 12.46 % ; Cl 55.2 '■% ... ff found: S 12.43 j Cl 54.15.

The Carbozamides prepared in Examples 1 and 2 were tested for bactericidal by the following procedure and algisside effect investigated

Algicidal effect:

One made from the same filing Ö * rboxamid 4o «tone loosening; was »it aofriel broth Teraiselit that

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a concentration of 2 ppm carboxamide resulted. Four Pair of sample beakers of 150 ml were used with this oemic filled. 350-400 g of the test organism are added to each sample cup and the cups were then placed in a Climate chamber placed for incubation. The cups were periodically examined for algae growth. The algicidal Effectiveness of the carboxamide was based on a final Assessment of the algae growth after 10 days is determined.

Me results of these tests are in Table I. reproduced »in which the mean value calculated from the 4 Boppelversuöhßn is given as 0 to 100, where Q total ineffectiveness and 100 mean total effectiveness.

Bactericidal effect:

Bacterial suspensions were made by that you can culture the desired bacteria with sterile Water from a sloping agar bottom into a, vessel out of the rinsed and the aqueous suspension with sterile barrels further diluted to 250 ml *

Garboxamide to be tested was dissolved to 500 ppm in acetone and 30% of this solution was pipetted onto each of 2 surfaces of a plate covered with 20 ml of Emerson agar. Üie treated agar plates were then sprayed with the Bakterien8uspenaion and incubated for 44 to 48 hours at 24 ⁰ C. The two treated plate surfaces were then examined for bacterial growth. Me Wiiit-

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inspected ¹

Samkeit dee Carboxaaide regarding the fight against the Bacterial wmchetuma on the treated flee was rait + or - Devaluate "where + means ·" that the surfaces completely free from BaJcterienwaohetuii and - meant that they could be completely overgrown by bacteria. The results of these bacteria are also shown in Table I.

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Iib »llt I ι

Connection Effectiveness

algitide

Nitell *

Eugltn

Pe "udone" e Erwinia Syringe

H- (1,1,2,2-t * tr * chlorithylthio) formamide

N- (l, l, 2 _t 2-t «trachloroethylthio). nootamid

100

100

86

In further jjakteri.zid ~ T.eats. could ianthomonas xnaseoli, Agrobacteriua tasafaciens _t Gorynebacteria michiganenae and A. aerogenes ait S- (1,1,2,2-Tetraehlorätii.ylthio) foraa3iid bei'einer Kcnzentra-Eion of 10 ppm in substantially (to AENR than 50 ^) are bsiCäspft .

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Claims (4)

_ ίο - Patent applications: 1, bactericide uöd algicide, labeled iureix a G-enslt at jsin at least one li-r a aer alleesseinöi; ? orffiel OH
ECSSH ¹ in the 3rd a hydrogen or an alkyl radical with 1 to 2 carbon atoms. and R ¹ denotes a tetrahydrofuran ether radical, narln let halogens have an atomic number τοπ 17 to 35, as an active ingredient. 2. Bakterizid and Algizia nack claim 1, wherein E ^{1 is} a tetrachloroethyl radical. 3. Bactericide and algicide after injection 1,% * orin H "means a 1,1,2,2-fetraenlcrätiiylrest. 4. Bactericide and algicide after. Addressed, 1, wherein the concentration of the active ingredient in the water to be treated is between 0.1 and 50 ppm. 009886/2141 5 · .JWÄ'teiSUiid i "cb Aaepruch l _f known""indicatesthat" * Wt fight iron piiana pathogens Fürt Öhevron leeÄgrch Lawyer BATH ORIGINAL 009886/2141