DE1285786B - fungicide - Google Patents

Description

contains, in which X and X 'fluorine or chlorine, η an integer from 1 to 4, m an integer from 1 to 3 and either Ri is hydrogen and R2 is a phenyl,

Vinyl or 3-phenylpropin- (l) -yl group or a 20-sided or formation of noticeable secondary alkyl group with 1 to 3 carbon atoms, which accompanies products. The infrared spectrum of the possibly by bromine atoms; Hydroxy or nitro adducts suggests that they are carbonyl adducts groups or are substituted by groups of the formula - NRR 'of the halogenated acetone, i.e. one hemiketal may be, wherein R and R 'have structure. However, this is only intended as a the phenyl radical or, if appropriate, hydroxyl or theory or hypothesis, and none mean amino-substituted lower alkyl radicals, or an absolutely correct statement regarding the structure Ri and R2 together with the door that supports them mean.

Carbon atom represent the cyclohexyl radical, under The reaction after which the invention

Except for the sym.-dichlorotetrafluoroacetone, whose halogenated acetone alcohol adducts contain who-hydrates and that of aliphatic alcohols can be used within a wide range with a with 1 to 20 carbon atoms formed Aiko- large number of reactants vorgeholaten. be taken. However, it has been found that the

The subject of the German patent 1 203 535 are alcoholic components of an aliphatic nature Fungicides, which should be sym.-dichloro as the active substance, d. i.e., the hydroxyl function cannot tetrafluoroacetone or its hydrates or its 35 sit on a carbon atom that is part of a of aliphatic alcohols with 1 to 20 carbon aromatic ring system. When the hydrogen atoms contain formed alcoholates. hydroxyl function on the alcoholic reaction

It has now been found that the alcoholates also participate in a variety of electronegative of dichlorotetrafluoroacetone is surrounded by other alcohol groups, the reactivity becomes than the above-mentioned aliphatic alcohols 40 of the hydroxyl function in terms of their ability to as well as the completely halogenated acetones with the completely halogenated acetone one

Complex, reduced or even ineffective

CF3 made sam. In this context, z. B.

I found that 2,2,2-trichloroethanol is inactive. A

CO (II) 45 other, non-reactive alcohol is completely

I constantly halogenated ethanol, such as. B. fluorinated

CF2CI ethanol. With regard to this implementation was also

and found that the carbon atom of the aliphatic

CF3 carbinols do not directly contain more than 2 halogen

I 50 atoms or a fully halogenated methyl

CO (III) should carry the rest. There, as already stated above

I was, the implementation, after which the inventive

CF3 according to compounds are obtained, an Ad

dition of the alcoholic component and the

and whose hydrates and alcohol adducts appear to be the effective 55 carbonyl function of acetone, Means for combating microorganisms are, the reacting compounds should be steric if the alcohol component of the formula (I) is unsuitable, d. h., it should be directly at the speaks. Carbon atom of the carbinol sitting groups

Those contained as active ingredient according to the invention should not be too extensive. For example, the production of hydrates and alcohol adducts can be achieved by not using the halogenated ketone and chlorotetrafluoroacetone.
Water or the required alcoholic compo- The in the fungicides according to the invention are

brings each other into contact. The in- volved are halogenated acetone-alcohol adducts Settlement is expedient in the presence of a systemic toxin, and this property is effected normally liquid organic solvent 65 and increases their utility and their made, e.g. B. lower ketones, such as acetone value. A systemic biocide is produced internally by the or methyl ethyl ketone, saturated aliphatic and added organism to which it is applied aromatic hydrocarbons as well as their normal- will; it remains in the tissue of the organism and

retains its toxicological properties there. Systemic toxins are not weathering exposed when applied to planting as they are located within the interstices of the plant tissue are located, which thereby internally against the action of invading microorganisms, such as B. fungi and bacteria, is immunized. There have already been certain halogenated acetones proposed for combating fungi and related harmful microorganisms, and there have been various chloroacetones, especially chlorodichloroacetone and sym.-dichloroacetone, proven valuable. However, chlorinated acetones do not work systemically, but practice their effect only through direct local action on the microorganisms. Even the Completely halogenated acetone alcoholates show no general or universal fungicidal as a group Effect. For example, numerous adducts have been made from alcohols and 1,3-trichloro-1,3,3-trifluoroacetone made with different alcoholic components, and surprisingly it was found that such substances do not show the systemic effect by which the particular fluorinated and chlorofluorinated acetone-alcohol adducts of the present invention are characterized.

According to the prior art to date, no systemically acting fungicides are known.

CClF ₂
C = O

_ CClF ₂

example 1

• [CH ₂ = CH-CH ₂ OH] ₃

17.5 g of allyl alcohol were gradually added to 20.0 g of sym.-dichlorotetrafluoroacetone, which had been dissolved in 60 ecm of methylene dichloride, and the temperature was kept ^{at about 40 ° C. during the addition.} The mixture was allowed to cool to room temperature and then subjected to fractional distillation at normal pressure. (. Of active ingredient No. 1) The product had a boiling point of 108 ⁰ C and was a colorless oil with a ⁵ Nl - value of 1.4045. It was obtained in essentially quantitative yield. The chemical and physical analyzes showed the ratio of reactants given by the above formula.

The following active ingredients were obtained using the same procedure:

Active ingredient
No. Halogenated
Ketone *) Alcoholic component C ₂ H ₅ - N relationship Physical Properties 2 5FK Ethyl alcohol ^ CH ₂ CH ₂ OH 1: 3 JVi, ⁵ = 1.3565 3 dFK Ethyl alcohol 4th 4FK Benzyl alcohol 1: 2 Colorless oil, AP ₀ ⁵ = 1.4921 5 4FK Cyclohexanol 1: 2 Light yellow oil, Nl ⁵ = 1.4415 6th 4FK 1,2 propanediol 2: 1 Colorless oil, AP ₀ ⁵ = 1.4045 7th 4FK Glycerin 1: 1 Colorless viscous oil, AF = ₀ ⁵ 1.4250 8th 4FK / V-CH ₂ -C = C-CH ₂ OH 1: 2 Light brown oil, JVS? ' = 1.4712 9 4FK BrCH ₂ CH ₂ OH 1: 1 Light brown oil, JV I ⁵ = 1.4280 10 4FK CH3 CH CH ₂ CH ₂ OH 1: 1 Yellow oil, AP ₀ ⁵ = 1.4156 NO ₂ / CH ₂ OH 11 4FK NO ₂ • C-CH ₂ OH 3: 1 Pale yellow liquid, AP ₀ ⁵ = 1.4156 ^X CH ₂ OH / CH ₂ CH ₂ OH 12th 4FK 2: 1 White solid, M.p. = 130 ⁰ C

CF ₂ Cl
*) 4FK = C = O

CF ₂ Cl

/ ^CF '

5FK = C = O
\
CF ₂ Cl

/ ^CF -

6FK = C = O

\
CF ₃

continuation

Active ingredient
No. Halogenated
Ketone *) Alcoholic component 2 relationship Physical Properties 13th
14th 4FK
5FK / CH ₂ CH ₂ OH
O-\
^ CH ₂ CH, OH
H ₂ O 2 2: 1 White solid,
Melting point = 84 ° C
(Not isolated) 15th 4FK 2: 1 Yellow glassy product 16 4FK 4: 1 White semi-solid material 17th 6FK Colorless liquid HIGH ₂ CH ₂ K
NCH ₂
HIGH ₂ CH ₂ / HIGH ₂ CH ₂ V
NCH ₂
HIGH ₂ CH ₂ / H ₂ O

CF ₂ CI

4FK = C = O

CF ₂ Cl

CF,
5FK = C = O

Vf, ci

6FK = C = O

CF,

CF,

Systemic tube test

When performing the systemic fungicide tube tests, 60 ecm of the compound to be tested first diluted to 50 ppm and then placed in small tubes. In each of the tubes a pinto bean plant was placed in it so carefully that only the roots of the Test liquid were touched and the remaining parts of the plant remained untouched. The tube was closed with a cotton plug. After 48 hours, two plants with bean brandy and two more inoculated with powdered meltau and stored in a cloud chamber overnight. The treated and untreated plants were then compared and the results evaluated. The same experiments were carried out with test solutions in decreasing concentrations. the The results obtained are shown in Table I.

Soak test

When carrying out the soil soaking test, cardboard boxes were filled with 454 g of soil each and this Soaked soil with various concentrations of an aqueous solution of the compound to be tested or doused. This method and its evaluation is described in detail in the journal »Phytopathology«, Vol. 54, No. 5, pp. 580-583 (May 1964) by T. C. Allen, Jr. and A. H. Freiberg. The plants were then planted in the soil treated in this way, proceeding with such care was that only the roots and no other parts of the plant were in contact with the ground came. The plants were then inoculated and further treated exactly as in the tube test above. The test results are given in Table I.

Table I.

Systemic powdered
Meltau Soaked floor powdered
Meltau Active ingredient Tube test 25th No. fire 25th fire 1 5 50 0.75 6th 5 25th 0.75 7th 5 > 50 0.75 10 5 25th 11 5 25th 16 10 10 0.375 4th 5 25th 0.75 8th 5 50 1.5 5 5 10 1.5 6th 12th 5 25th 15th 5 10 1.5 9 5 5 13th 1 5 17th 1 5 3 0.5 5 14th 1 2 1

The numbers indicate the respective concentrations in ppm that are necessary for the complete destruction of the Fungus lead.

Leaf nest

In the leaf test, both the protective and the systemic effects of the test Fungicide determined.

a) Protective effect

Pinto bean plants were used to determine the protective effect sprayed with aqueous solutions of the fungicide to be tested in concentrations of 1000, 500 and 100 ppm. Appropriately Surfactants or wetting agents are added to the aqueous dispersion to make the formulation to facilitate dispersion. After the leaves were dried, they became after Inoculated with the above method with bean blister and meltau pores and treated further. Both Results shown in Table II, the number 100 means that no pustules or meltau are to be found are observed, + + + + means a 75- to 100% destruction, + + + 50- to 75%, + + 25 to 50% and + no visible destruction.

Table II

Active ingredient 1000 fire 100 Powdered meltau 1000 500 100 Fire under Weathering conditions 100 100 No. 100 500 + + + + 1000 500 100 100 1 100 100 100 100 100 100 6th 100 100 + + + + + + + + 100 100 7th 100 100 100 100 10 100 100 + + + + + + + + 100 11 100 100 100 + + + + + + + 100 16 100 100 + + + + 100 + + + + + + + 4th 100 100 + + + + + + + + 100 + 8th 100 100 + + + + 100 + + + + 5 100 100 100 + + + + + + + + 100 100 12th 100 100 100 + + + + + 100 100 15th 100 100 100 + + + + + + 100 100 9 100 100 100 + + + + + 100 + + + 13th 100 100 100 100 100 + + + + + + + + 17th 100 100 100 100 + + + + + + + + + + 100 + 3 100 100 100 100 100 + + + + + + + + 100 100 14th 100 100 100 100 + + + + + + + 100 100 2 100 100

When determining the protective effect against »fire under weathering conditions«, the pinto bean plants treated with the compound to be tested Exposed to weathering conditions for 2 days, d. that is, they were for 2 days Sunlight and exposed to a fine mist in a humidity chamber for 2 nights and only then inoculated with fire and placed in the greenhouse.

b) Systemic effect

To determine the systemic effect on plant leaves, primary leaves of pinto beans were used sprayed with a solution of the respective test compound. After that, the secondary After the leaves have unfolded, inoculated with bean blight spores according to the above method and treated further. The secondary leaves that were just unfolding became when the .primary leaves covered.

At concentrations of 1000 and 500 ppm, almost all of the fungicides according to the invention showed one 100% destruction effect on secondary leaves.

Claims (1)

Claim: Fungicide containing perhaloacetone derivatives, thereby characterized in that it is a polyfluoroacetone as the active ingredient the formula CF ₃ -CO-CF ₂ X its hydrate or an alcohol adduct of the formula (XCF ₂ -CO-CF ₂ X '). ¹ X CH-OH contains, in which X and X 'fluorine or chlorine, 11 is an integer from 1 to 4, m is an integer from 1 to 3 and either Ri is hydrogen and R2 is a phenyl, vinyl or 3-phenylpropine (l) - yl group or an alkyl group with 1 to 3 carbon atoms, which may optionally be substituted by bromine atoms, hydroxyl or nitro groups or by groups of the formula —NRR ', where R and R' denote the phenyl radical or optionally hydroxyl- or amino-substituted lower alkyl radicals, or Ri and R2 together with the carbon atom bearing them represent the cyclohexyl radical, with the exception of sym.-dichlorotetrafluoroacetone, its hydrates and its alcoholates formed from aliphatic alcohols having 1 to 20 carbon atoms. 809648/1908