DE2029191A1 - Fluoroacetamide tickicides -n-(2,2,2-trichloro-1-phenylthioethyl) - fluoroacetamides and their prepn - Google Patents

Abstract

Fluoroacetamide tickicides - N-(2,2,2,-trichloro-1-phenylthioethyl)-fluoroacetamides and their prepn. Cpds of formula: (where R=halogen and n=2 or 3, or R=t-Bu and n=1) are tickicides and also insecticides, acaricides, selective rodenticides, fungicides and bactericides, and may be prepd by reacting a (R)n-substd. thiophenol (or its alkali metal or NH4 salt) with N-(2,2,2-trichloro-1-chloroethyl)fluoroacetamide.

Description

N- (2.2.2-Trichlor-1-henylmercaptoethyl) -fluoroacetic acid amide. procedure for their preparation and their use as tickicides The present invention relates to new N - (2.2.2-Trichlorl-phenylmercaptoethyl) -fluoroacetic acid amides, which have tickicidal properties and a process for their manufacture.

It is already known that N- (2.2.2-trichloro-l-monochlorophenylmercapto-ethyl) -fluoroacetic acid amides, e.g. N-z2.2.2-trichloro-l- (p-chlorophenylmercapto) -äthylS-fluoroacetic acid amide, have an insecticidal and acaricidal effect (see J.Sci.Food Agric 16, 330 (1965), Belgian patent 693 575).

It has now been found that the new N- (2.2.2-Trichlorl-phenylmercaptoethyl) -fluoroacetic acid amides of the formula (1) in which R is a halogen atom or the tert. Butyl radical and n for the case that R is halogen, has the value 2 or 3 and if R represents the tert-butyl radical, is 1, have strong tickicidal and insecticidal, acaricidal, selective rodenticidal, fungicidal and bactericidal properties.

It has also been found that the N- (2.2.2-Trichlorl-phenylmercapto-ethyl) -fluoroacetic acid amides of the constitution (I) are obtained when N- (2.2.2-trichloro-1-chloroethyl) -fluoroacetic acid amide of the formula (II ) with thiophenols of the formula (III) in which R and n have the meaning given above and X stands for a hydrogen or alkali atom or the ammonium group, in the presence or absence of acid binders.

Surprisingly, the ivr- (2 * 2.2-trichloro-1-phenylmercapto-ethyl) -fluoroacetic acid amides have them an equally good, e.g. better tickicidal, if the dinant toxicity is significantly lower Effect like the well-known N- (2.2.2-trichloro-1-monochlorophenyl-mercapto-ethyl) -fluoroacetic acid amides, which are the closest chemically comparable active ingredients with the same direction of action. The compounds according to the invention thus represent a real asset to technology represent.

If 14- (2.2. 2-Trichlor-1-chloroethyl) -fluoroacetic acid amide and 2,4-dichlorothiophenol are used as starting materials, the course of the reaction can be represented by the following equation: O C1 acid- O C1 F-CH2-C-NH-CH-C1 + HS b C1 HSCl F-CH, -CI \ KI-CH-S- -HCl F-CH2-C-NH-CH - HC1 CC13 CC15 The starting materials to be used for the process are clearly defined by the formulas (II) and (III). In the formula (III), however, R preferably represents chlorine and the tert. Butyl radical.

All inert organic solvents or thinning agents can be used Solvents or thinners in question. These include, in particular, aliphatic and aromatic, optionally chlorinated hydrocarbons, such as benzene, toluene, Xylene, gasoline, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, Ethers such as diethyl and dibutyl ethers, dioxane, and ketones such as acetone, methylethyl, Nethyl isopropyl and methyl isobutyl ketone, as well as nitriles such as acetonitrile.

All customary acid binders can be used as acid acceptors. Alkali carbonates and alcoholates, such as sodium or potassium carbonate, methylate or ethylate, also aliphatic, aromatic or heterocyclic amines, for example triethylamine, dimethylamine, dimethylaniline, Dimethylbenzylamine and pyridine.

The reaction temperatures can be varied within a relatively wide range will. In general, between 20 and 50, preferably 20 to 250C.

The reactions are generally carried out under normal pressure.

When carrying out the process, the starting materials are equimolar Ratio a. An excess of one or other reaction component does not bring any significant advantages. The implementation takes place in one of the above Solvent in the presence or absence of an acid acceptor, preferably at room temperature. After several hours of stirring at room temperature, the mixture is made by customary methods worked up.

The substances according to the invention are mostly in the form of crystalline compounds which are characterized by their melting point and elemental analysis can.

TlZie already mentioned several times above, have the invention Compounds strong tickicidal, especially acaricidal properties, especially against acarids, animals domesticated as animal ectoparasites, such as cattle and infested sheep. They are therefore well suited for combating animal ectoparasites from the order of the Akarida. As economically important ectoparasites of this type, which play a particularly important role in tropical and subtropical countries, Examples include: the Australian and South American beef ticks Boophilus microplus, the South African beef tick, Boophilus decoloratus, both from the family of the Ixodidae.

In the course of time, the above-mentioned ticks are in different areas against the phosphoric acid esters and carbamates previously used as control agents become resistant, so that the control success in many areas is called into question will. To ensure economic livestock husbandry in the infested areas hence a need for means by which ticks, even more resistant strains, for example of the genus Boophilus can be safely fought. To a large extent against the previous ones Phosphoric acid ester agents and carbamates are resistant, for example, in Australia the Ridgeland tribe and the Biarra tribe of Boophilus microplus. The active ingredients according to the invention are both against the normally sensitive and equally effective against the resistant strains, for example Boophilus. she have a strong egg deposition inhibiting effect on the adult forms. The application of these active ingredients takes place in the usual way, for example by spraying, dousing, misting or as a bath (dip). The formulations or the ready-to-use solutions can still other auxiliaries or active ingredients, such as disinfectants, are added.

Example A: In vitro test for egg-deposition-inhibiting effect on ticks.

3 parts of active ingredient will be'mit 7 parts of a mixture of the same Parts by weight of ethylene glycol monomethyl ether and nonylphenol polyglycol ether mixed. The emulsion concentrate obtained in this way is adjusted to the desired e with water Application concentration diluted.

Adult fully suckled female ticks are put into this active substance preparation of the species Boophilus microplus (resistant) immersed for one minute. After diving from every 10 female specimens of the different tick strains one transfers the individual ticks in plastic trays, the bottom of which is covered with a filter paper disc is occupied. The effectiveness of the active compound preparation is determined after 35 days by determining the inhibition of the deposition of fertile eggs compared to egg deposition of untreated control ticks. The effect is given in%, where 100% means that no more fertile sows were deposited and 0 yo means that the ticks are in normally like the untreated control ticks laid eggs.

Investigated active ingredients, tested concentrations, tested parasites and the results obtained are shown in the following table.

Table in vitro test for ovicidal effects on ticks 1 Active ingredient medium tox. oviz.Wkg. gegen Mouse or I Boophilus microglus Rat jBiarra strain per os inhibition in one Wkst.-Ronz. from ~ 100 74> 50% ci FCH2-CO-NH-CH-S-C1 mouse: CCl5 2000 0.03 0.01 (according to the invention) C1 i? CH2CONHCCIHlSÄ} /) \ la mouse: r 2000 0.1 0.03 CC1I 5 (according to the invention) FCH2-CO-NH-CH-S / Cl j'I from: 1 - CClj ç 1000 0.01 0.005 3 (according to the invention) FCH2-CO-I-CH-S e C (CH3) 3 mouse: 0.1 003 CClg 100 0.1 0.03 (according to the invention) (according to the invention) FCH2-CO-NH-CH-OH rat: CCl3 7.5 0.3 0.1 (known) (known) FCH2-CO-NH2 rat: (known) 5 0.03 0.01 Example B: 72 g (0.3 mol) of N- (2.2.2-trichloro-1-chloro) -fluoroacetic acid amide are dissolved in 300 ml of acetonitrile, and 30 g (0.3 mol) of triethylamine are added. At room temperature, 54 g (0.3 mol) of 2,4-dichlorothiophenol are dissolved in a little acetonitrile, added dropwise, then the mixture is stirred overnight and the precipitated triethylamine hydrochloride is filtered off with suction. The filtrate is concentrated, and the above compound crystallizes out with a melting point of 720C.

The yield is 84 g = (83% theoretical).

Analysis: C1 N Calculated for C10H7Cl5FNOS (molecular weight 385.5): 46, o %; 3.63; Found: 45.85%; 3.56%.

The following connections can be established in an analogous manner: Yield: 55.5% of theory mp: 850C (from cyclohexane) Analysis: NS Calculated for CloH7Cl5FNOS (molecular weight 385.5): 3.63%; 8.30%; Found: 3.62%; 8.63%.

Yield: 75.5% of theory. M.p .: 660C Analysis: NS Calculated for C10H6Cl6FNOS (molecular weight 420): 3.34%; 7.64%; Found: 3.38%; 7.80%.

Yield: 68% of theory. Mp. 520C Analysis: N Calculated for C14H17Cl3FNOS (Molecular weight 372.5): 3.76%; Found: 3.73 5 '.

Claims (5)

Patent claims: 9 N- (2.2.2-trichloro-1-phenylmercaptoethyl) -fluoroacetic acid amides of the formula in which R is a halogen atom or the tert. Butyl radical and n for the case that R is halogen, has the value 2 or 3 and if R is the tert. Butyl radical is equal to 1. 2. Process for the preparation of N- (2.2.2-trichloro-l-phenyl mercapto-ethyl) -fluoroacetic acid amides, characterized in that N- (2.2.2-trichloro-1-chloroethyl) -fluoroacetic acid amide with thiophenols of the formula in which R and n have the meaning given in claim 1 and X is a hydrogen or alkali atom or the ammonium group, in the presence or absence of acid binders. 3. Tickicidal agents characterized by a content of compounds according to claim 1. 4. A method of combating ticks, characterized in that one compounds according to claim 1 on the said pests or their habitat let it act. 5. Use of compounds according to Claim 1 for combating Ticks. 6, a process for the production of tickicidal agents, characterized in, that one compounds according to claim 1 with extenders and / or surface-active Means mixes.