Note: Descriptions are shown in the official language in which they were submitted.
.. 20 ~ 1087
1
USE OF TRIFLUOROMETHYLPHENYLAZOLYLMETHYLOXIRANES
AS CROP PROTECTION AGENTS
The present invention as broadly disclosed
relates to a broad family of azole compounds, a process for
the preparation thereof and fungicides containing these.
The invention as claimed hereinafter is however
restricted to the use of some of said compounds for
controlling fungi.
EP-A 94 564 discloses azolylmethyloxiranes, in
particular 2-(1,2,4-triazol-1-ylmethyl)-2-(4-chlorophenyl)-
3-(3-trifluoromethyl)oxirane whose fungicidal action is not
satisfactory in all cases.
It has been discovered that very specific
azolylmethyloxiranes have an improved action. These
compounds are of the formula:
0 R2
X /
rJN-CH 2-C-CH~
R1
n
where:
Rl is hydrogen, halogen, nitro, phenyl, phenoxy, C1-C5-
alkoxy, Cl-C4-haloalkyl, Cl-C5-haloalkoxy and,
furthermore, Rl together with the phenyl nucleus can
also form naphthyl which is unsubstituted or
substututed by Rl,
n is an integer from 1 to 5,
R2 is ortho- or para-trifluoromethyl,
X is CH or N
A
2011087
la
and the acid addition salts or methal salts thereof which
are tolerated by plants.
These compounds have a better fungicidal action,
especially against diseases of cereals, than known
azol.ylmethyloxiranes.
As aforesaid, the present invention as claimed is
restricted to the use of such of these compounds. More
specifically, the invention as claimed in directed to a
process for combating fungi, wherein a fungicidally
effective amount of an azolylmethyloxirane of the general
formula (I'):
0 R2
~N-CH2-C~~ (I,)
R1
n
where:
Rl is hydrogen, halogen, nitro, phenyl, phenoxy, Cl-C5-
alkyl, Cl-C5-alkoxy, Cl-C4-haloalkyl, Cl-C5-haloalkoxy
and, furthermore, Rl together with the phenyl nucleus
may also form naphthyl which is unsubstituted or
substituted by Rl,
n is an integer from 1 to 5,
R2 is ortho-or para-trifluoromethyl, with the proviso
that when R2 is para-trifluoromethyl, Rl is not
hydrogen,
or a plant-tolerated acid addition salt or metal
salt thereof is allowed to act on the fungi, or the
materials, areas, timber, plants or seed threatened by
fungus attack.
A
20 1 1 0 8~'
lb
The compounds of the formula I contain chiral
centers and are generally obtained in the form of
reacemates or diastereomeric mixtures of erythro and threo
forms. The erythro and threo diastereomers of the compounds
~...."..a; .-"., t" tho i n~rant; ~n r-an he separated in a
A
- 2 - ~~~ ~ ~ ~~. Z . 0050/40637
conventional manner, for example on the basis of their
different solubilities or by column chromatography, and
isolated in pure form. Pure enantiomers can be obtained
by conventional methods from a diastereomer isolated in
such a way. Both the pure diastereomers or enantiomers
and the mixtures thereof produced in the synthesis are
used as fungicidal agents.
Examples of R1 are:
halogen such as fluorine, chlorine, bromine or iodine,
nitro, phenyl or phenoxy, eg. in the para position, C1-C5
alkyl or C1-CS-alkoxy, each alkyl being methyl, ethyl,
propyl, isopropyl, n-butyl, sec-butyl, tert-butyl,
n-pentyl or neopentyl, C1-C4-haloalkyl or C1-C4-haloalkoxy,
especially mono- to perhalogenated alkyls such as CHZC1,
CHC12, CC13, CHZF, CHF2, CH2Br, CHBrCl, CF2C1, CZFS, CF2-
CHF2, CHzCHZCl, CH2CHC12, CH2CHZBr, C3F~ and, in particular,
CF3.
In addition, Ri can form, together with the phenyl
nucleus to which it is bonded, a naphthyl, eg. 1-naphthyl
or 2-naphthyl, which in turn can be substituted one or
more times by the radicals mentioned above for Rl.
n is an integer from 1 to 5, in particular 1
to 3.
Examples of acid addition salts are the hydro-
chlorides, hydrobromides, sulfates, nitrates, phosphates,
oxalates or dodecylbenzenesulfonates. The activity of the
salts derives from the cation so that generally the anion
is immaterial. The salts of the active compounds accord-
ing to the invention are prepared by reacting the azolyl-
methyloxiranes (I) with suitable acids.
Metal salts of the active compounds I or their
salts can be formed with, for example, copper, zinc, tin,
manganese, iron, cobalt or nickel by reacting the azolyl-
methyloxiranes with corresponding metal salts.
The compounds of the formula I can be prepared by
a) reacting a compound of the formula II
~o~~os~
- 3 - O.Z. 0050/40637
0 RZ
_ L-CHZ-C/ \C~ I I
R1
n
where R1 and RZ have the stated meanings, and L is a
leaving group which can be replaced nucleophili-
cally, with a compound of the formula III
~x~N-Me III
where Me is hydrogen or a metal, and X has the
stated meaning, or
b) converting a compound of the formula IV
~x' R 2
CH~
IV
R1
n
where R1, RZ, n and X have the stated meanings, into
the epoxide and, where appropriate, converting the
resulting compounds into their salts with acids
which are tolerated by plants.
Reaction a) is carried out, if Me is hydrogen, in
the presence or absence of a solvent or diluent and with
or without the addition of an inorganic or organic base
and of a reaction accelerator.
The preferred solvents and diluents include
ketones such as acetone, methyl ethyl ketone or cyclo
hexanone, nitriles such as acetonitrile or propionitrile,
alcohols such as methanol, ethanol, iso-propanol, n-
butanol or glycol, esters such as ethyl acetate, methyl
~01108'~
- 4 - O.Z. 0050/40637
acetate or butyl acetate, ethers such as tetrahydrofuran,
diethyl ether, methyl tert-butyl ether, dimethoxyethane,
dioxane or diisopropyl ether, amides such as dimethyl-
formamide, dimethylacetamide or N-methylpyrrolidone, as
well as dimethyl sulfoxide, sulfolane or mixtures
thereof.
Examples of suitable bases, which can also be
used as acid-binding agents in the reaction, are alkali
metal hydroxides such as lithium, sodium or potassium
hydroxide, alkali metal carbonates such as sodium,
potassium or cesium carbonate, or sodium, potassium or
cesium bicarbonate, pyridine or 4-dimethylaminopyridine,
alkali metal hydrides such as lithium, sodium or potas-
sium hydride, alkali metal amides such as of sodium or
potassium, as well as sodium or potassium tert-butoxide,
triphenylmethyllithium, -sodium or -potassium, and
naphthyllithium, -sodium or -potassium. However, it is
also possible to use other conventional bases.
Suitable and preferred reaction accelerators are
metal halides such as sodium iodide or potassium iodide,
quaternary ammonium salts such as tetrabutylammonium
chloride, bromide, iodide or bisulfate, benzyltriethyl
ammonium chloride or bromide or crown ethers such as 12
crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown or
dicyclohexano-18-crown-6.
The reaction is generally carried out at from 10
to 150°C, in particular 20 to 120°C, under atmospheric or
superatmospheric pressure, continuously or batchwise.
If Me is a metal, reaction a) can be carried out
in the presence of a solvent or diluent and at from -10
to 150°C, in particular 0 to 120°C, preferably 20 to
80°C. When a solvent is present, the reaction is expedi
ently carried out at the boiling point of the solvent.
The preferred solvents and diluents include
amides such as dimethylformamide, diethylformamide,
dimethylacetamide,diethylacetamide,N-methylpyrrolidone,
hexamethylphosphoric triamide, sulfoxides such as
2Q11~$7
- 5 - O.Z. 0050/40637
dimethyl sulfoxide and, finally, sulfolane.
Suitable solvents and diluents for reaction b)
are ketones such as acetone, methyl ethyl ketone or
cyclohexanone, nitriles such as acetonitrile or propio-
nitrile, alcohols such as methanol, ethanol, iso-propa-
nol, n-butanol or glycol, esters such as ethyl acetate,
methyl acetate or butyl acetate, ethers such as tetra-
hydrofuran, diethyl ether, dimethoxyethane, dioxane,
diisopropyl ether or methyl tert-butyl ether, amides such
as dimethylformamide, dimethylacetamide or N-methyl-
pyrrolidone, as well as dimethyl sulfoxide, sulfolane or
mixtures thereof.
The novel starting compounds II are obtained by
epoxidation of the corresponding olefins V:
R2
L
i
_ ~~ V
R1
n
(cf. G. Dittus in Houben-Weyl-Miiller, Methoden der
Organischen Chemie, Georg Thieme Verlag, Stuttgart, 1965,
vol. VI, 3, pages 385 et seq.).
Compound V is prepared by halogenating or oxidiz-
ing olefins of the formula VI
RZ
CH
C
VI
R1
n
in the allyl position by conventional methods.
Suitable halogenating reagents are N-chloro- and
N-bromosuccinimide. Examples of solvents are halohydro
carbons such as carbon tetrachloride, trichloroethane or
methylene chloride. The halogenation is generally carried
X011087
- 6 - O.Z. 0050/40637
out at from 20 to 100°C.
The allyl oxidation is carried out with peresters
such as tert-butyl perbenzoate or tert-butyl peracetate
in the presence of a heavy metal salt such as copper(I)
chloride or copper(I) bromide. The oxidation is usually
carried out in inert solvents such as dichloromethane,
toluene, xylene, chloroform, tetrachloromethane or
dichloromethane at from 10 to 100°C.
The allyl halides V and the allyl alcohols with
L - OH obtained in this way are subsequently converted
into the corresponding epoxides II and VII.
0 RZ
HO---~ / \ ~-~/
C-C H
VII
R1
n
For this, the olefins V are oxidized with peroxy-
carboxylic acids such as perbenzoic acid, 3-chloroper-
benzoic acid, 4-nitroperbenzoic acid, monoperphthalic
acid, peracetic acid, perpropionic acid, permaleic acid,
monopersuccinic acid, perpelargonic acid or trifluoroper-
acetic acid in inert solvents, preferably chlorinated
hydrocarbons, eg. methylene chloride, chloroform, carbon
tetrachloride or dichloroethane, but possibly also in
acetic acid, ethyl acetate, acetone or dimethylformamide,
in the presence or absence of a buffer such as sodium
acetate, sodium carbonate, disodium hydrogen phosphate or
Triton B.
The reaction is carried out at from 10 to 100°C,
and the reaction can be catalyzed with, for example,
iodine, sodium tungstate or light. Also suitable for the
oxidation are alkaline solutions of hydrogen peroxide
(about 30 ~ strength) in methanol, ethanol, acetone or
acetonitrile at 25 to 30 °C, and alkyl hydroperoxides, eg.
tert-butyl hydroperoxide, cumene hydroperoxide and
20~1~8~
- 7 - o.z. 005040637
cyclohexyl hydroperoxide, with or without the addition of
a catalyst, eg. sodium tungstate, pertungstic acid,
molybdenum hexacarbonyl or vanadyl acetylacetonate. Some
of these oxidizing agents can be generated in situ.
Whereas the resulting epoxy halides II (L -
halogen) can be immediately reacted by process a) , the
corresponding epoxy alcohols VII are converted into
reactive esters which are then reacted with the compounds
III by process a).
The reactive esters which are reacted with III
are prepared by conventional methods ( Houben-Weyl-Miiller,
Methoden der Organischen Chemie, Georg Thieme Verlag,
Stuttgart, 1955, volume 9, pages 388, 663, 671). Examples
of such esters are methanesulfonates, trifluoromethane-
sulfonates, 2,2,2-trifluoroethanesulfonates, nonafluoro-
butanesulfonates, 4-methylbenzenesulfonates, 4-bromo-
benzenesulfonates, 4-nitrobenzenesulfonates or benzene-
sulfonates.
The compounds V can be prepared by conventional
methods for olefin synthesis (Houben-Weyl-Miiller,
Methoden der Organischen Chemie, Georg Thieme Verlag,
Stuttgart, 1972, volume V, lb).
Furthermore, the epoxy alcohols VII can be
prepared by oxidation and subsequent reduction of the
propenals obtainable as described in DE-A 37 22 886.
These substituted propenals are dissolved in alcohols
such as methanol, et-hanol, n- or iso-propanol or buta-
nols, or solvent mixtures containing these alcohols are
used, and are oxidized with hydrogen peroxide, cyclohexyl
peroxide, tert-butyl hydroperoxide or cumene hydroper-
oxide with the addition of bases. The resulting formyl-
oxirane can be reduced without further purification to
the corresponding epoxy alcohol VII with basic sodium
borohydride solution or catalytically.
The examples which follow illustrate the prepara-
tion of the active compounds:
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- 8 - O.Z. 0050/40637
Preparation Examples
I Preparation of the starting materials
EXAMPLE A
4.2 g of sodium hydroxide in 30 ml of water are
added to a solution of 40 g of 2-trifluoromethylbenz
aldehyde in 300 ml of methanol. The reaction mixture is
cooled to 10°C, and 35 g of phenylacetaldehyde are
rapidly added, during which the solution warms to 30
40°C. The mixture is stirred at 40°C for 10 hours and
then 200 ml of water are added to the colorless reaction
solution, and the resulting emulsion is extracted by
shaking with methyl tert-butyl ether. The organic phase
is separated off, dried over sodium sulfate and concen-
trated. Filtration of the residue through a silica gel
column (ethyl acetate/n-hexane = 1:3) results in an 80 $
yield of E/Z-2-phenyl-3-(2-trifluoromethylphenyl)prope-
nal.
EXAMPLE B
52 g of E/Z-2-phenyl-3-(2-trifluoromethylphenyl)
propenal are dissolved in 300 ml of methanol, and 2.2 ml
of concentrated sodium hydroxide solution are added. The
reaction solution is stirred at 0°C while 14.3 g of
hydrogen peroxide (approximately 50 ~ strength) are
slowly added dropwise, during which the internal tempera
ture does not exceed 30°C. After the addition is com-
plete, the mixture is stirred at room temperature for 6
hours and subsequently 2.35 g of sodium borohydride
dissolved in a little 10 ~ strength sodium hydroxide
solution are added. The reaction mixture is stirred at
room temperature for 18 hours and then 200 ml of water
are added, and the resulting emulsion is extracted by
shaking with methylene chloride. The organic phase is
then dried over sodium sulfate and concentrated, and the
residue is recrystallized from isopropanol. A 62 $ yield
of cis-2-hydroxymethyl-2-phenyl-3-(2-trifluoromethyl-
phenyl)oxirane is obtained.
2~J~.1087
- 9 - O.Z. 0050/40637
EXAMPLE C
37.5 g of 4-methylbenzenesulfonyl chloride are
added to a solution of 49 g of cis-2-hydroxymethyl-2-
phenyl-3-(2-trifluoromethylphenyl)oxirane in 200 ml of
dichloromethane and 53 g of triethylamine at room temper-
ature. After 24 hours, the reaction mixture is washed
with aqueous sodium bicarbonate solution and water, dried
over sodium sulfate and evaporated under reduced pres-
sure. 55 g of cis-2-(4-methylbenzenesulfonyloxymethyl)-
2-phenyl-3-(2-trifluoromethylphenyl)oxirane are obtained
from the residue and subsequently reacted with triazole
as in the following example.
II Preparation of the final products
EXAMPLE 1
5.2 g of sodium hydroxide are added to a solution
of 9.4 g of 1,2,4-triazole in 100 ml of N-methylpyr-
rolidone, and the mixture is heated at 50°C for 30
minutes. After it has cooled to room temperature, 57 g of
cis-2-(4-methylbenzenesulfonyloxymethyl)-2-phenyl-3-(2-
trifluoromethylphenyl)oxirane dissolved in 100 ml of N-
methylpyrrolidone are slowly added dropwise, and the
mixture is stirred at room temperature for 12 hours.
Subsequently 200 ml of water are added, and the mixture
is extracted several times with methyl tert-butyl ether;
the organic phase is washed twice with water, dried over
sodium sulfate and concentrated. Crystallization from
methyl tert-butyl ether/n-hexane results in a 75 $ yield
of cis-2-(1,2,4-triazol-1-ylmethyl)-2-phenyl-3-(2-tri
fluoromethylphenyl)oxirane with melting point 132-134°C
(compound no. 1).
The compounds listed in the table can be prepared
as in Example 1:
2~1108'~
O.Z. 0050/40637
Table 0 R2
X
rJN-CHZ-C-CH~ I
N
R1
n
No. R1 R2 X M.p. (oC)/IR
n
5 1 H 2-CF3 N 132-134
2 2-Cl 2-CF3 N 1506,1315, 1172, 1124, 1038, 771
cm-1
3 2-F 2-CF3 N
4 4-Cl 2-CF3 N 117-119
5 4-F 2-CF3 N 110-112
106 2, 4-F2 2-CF3 N
7 2, 4-C12 2-CF3 N
8 4-Br 2-CF3 N
9 4-OCF3 2-CF3 N
10 4-OCH3 4-CF3 N
1511 H 4-CF3 N
12 2-Cl 4-CF3 N
13 2-F 4-CF3 N
14 4-Cl 4-CF3 N
4-F 4-CF3 N
2016 2, 4-F2 4-CF3 N
17 2, 4-C12 4-CF3 N
18 4-Br 4-CF3 N
19 4-OCF3 4-CF3 N
4-OCH3 4-CF3 CH
2521 H 2-CF3 CH 132-134
22 2-C1 2-CF3 CH 1503, 1315, 1170, 1124, 1038,
770 cm-1~"
23 2-F 2-CF3 CH
24 4-C1 2-CF3 CH
3025 4-F 2-CF3 CH 127-130
26 2, 4-F2 2-CF3 CH
27 2, 4-C12 2-CF3 CH
28 4-Br 2-CF3 CH
29 4-OCF3 2-CF3 CH
35
890092
11 O.Z. 0050/40637
Table - continued -
No. R1 R2 X M.p. (~C)
n
30 4-OCH3 4-CF3 CH
31 H 4-CF3 CH
32 2-C1 4-CF3 CH
33 2-F 4-CF3 CH
34 4-C1 4-CF3 CH
35 4-F 4-CF3 CH 1512, 1326, 1125, 1068, 840
cm-1
36 2,4-F2 4-CF3 CH
37 2, 4-C12 4-CF3 CH
38 4-Br 4-CF3 CH
39 4-OCF3 4-CF3 CH
40 4-OCH3 4-CF3 CH
2:1 cis/trans mixture
25
35
201108
12 O.Z. 0050/40637
Generally speaking, the novel compounds are extremely effective on a broad
spectrum of phytopathogenic fungi, in particular those from the Asco-
mycetes and Basidiomycetes classes. Some of them have a systemic action
and can be used as foliar and soil fungicides.
The fungicidal compounds are of particular interest for controlling a
large number of fungi in various crops or their seeds, especially wheat,
rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee,
sugar cane, fruit and ornamentals in horticulture and viticulture, and in
vegetables such as cucumbers, beans and cucurbits.
The novel compounds are particularly useful for controlling the following
plant diseases:
Erysiphe graminis in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,
Podosphaera leucotricha in apples,
uncinula necator in vines,
Puccinia species in cereals,
Rhizoctonia species in cotton and lawns,
Ustilago species in cereals and sugar cane,
Venturia inaequalis (scab) in apples,
Septoria nodorum in wheat,
Botrytis cinerea (gray mold) in strawberries and grapes,
Cercospora arachidicola in groundnuts,
Pseudocercosporella herpotrichoides in wheat and barley,
Pyricularia oryzae in rice,
Hemileia vastatrix in coffee,
Alternaria solani in potatoes and tomatoes,
Sclerotium rolfsii in groundnuts and lawn varieties,
Fusarium and Verticillium species in various plants.
The compounds are applied by spraying or dusting the plants with the
active ingredients, or treating the seeds of the plants with the active
ingredients. They may be applied before or after infection of the plants
or seeds by the fungi.
The novel substances can be converted into conventional formulations such
as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
The application forms depend entirely on the purposes for which they are
intended; they should at all events ensure a fine and uniform distribution
of the active ingredient. The formulations are produced in known manner,
for example by extending the active ingredient with solvents and/or
2fl~1~~~
13 O.Z. 0050/40637
carriers, with or without the use of emulsifiers and dispersants; if water
is used as solvent, it is also possible to employ other organic solvents
as auxiliary solvents. Suitable auxiliaries for this purpose are solvents
such as aromatics (e. g., xylene), chlorinated aromatics (e. g., chlorobenz-
enes), paraffins (e. g., crude oil fractions), alcohols (e. g., methanol,
butanol), ketones (e. g., cyclohexanone), amines (e. g., ethanolamine,
dimethylformamide), and water; carriers such as ground natural minerals
(e. g., kaolins, aluminas, talc and chalk) and ground synthetic minerals
(e. g., highly disperse silica and silicates); emulsifiers such as nonionic
and anionic emulsifiers (e. g., polyoxyethylene fatty alcohol ethers, alkyl
sulfonates and aryl sulfonates); and dispersants such as lignin, sulfite
waste liquors and methylcellulose.
The fungicidal agents generally contain from 0.1 to 95, and preferably
from 0.5 to 90, wt% of active ingredient. The application rates are from
0.02 to 3 kg or more of active ingredient per hectare, depending on the
type of effect desired. The novel compounds may also be used for protect-
ing materials, for example against wood-destroying fungi such as Conio-
phora puteana and Polystictus versicolor. The novel active ingredients may
also be employed as fungicidally effective components of oily wood pre-
servatives for protecting wood against wood-discoloring fungi. The agents
are applied by treating, e.g., impregnating or painting, the wood with
them.
The agents and the ready-to-use formulations prepared from them, such as
solutions, emulsions, suspensions, powders, dusts, pastes and granules,
are applied in conventional manner, for example by spraying, atomizing,
dusting, scattering, dressing or watering.
Examples of formulations are given below.
I. 90 parts by weight of compound no. 5 is mixed with 10 parts by weight
of N-methyl-a-pyrrolidone. A mixture is obtained which is suitable for
application in the form of very fine drops.
II. 20 parts by weight of compound no. 21 is dissolved in a mixture
consisting of 80 parts by weight of xylene, 10 parts by weight of the
adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-
monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzene-
sulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene
oxide and 1 mole of castor oil. By pouring the solution into water and
uniformly distributing it therein, an aqueous dispersion is obtained.
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14 O.Z. 0050/40637
III. 20 parts by weight of compound no. 25 is dissolved in a mixture con-
sisting of 40 parts by weight of cyclohexanone, 30 parts by weight of iso-
butanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide
and 1 mole of castor oil. By pouring the solution into water and finely
distributing it therein, an aqueous dispersion is obtained.
Iv. 20 parts by weight of compound no. 5 is dissolved in a mixture con-
sisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a
mineral oil fraction having a boiling point between 210 and 280°C, and
10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole
of castor oil. By pouring the solution into water and uniformly distribut-
ing it therein, an aqueous dispersion is obtained.
v. 80 parts by weight of compound no. 1 is well mixed with 3 parts by
weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid,
10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained
from a sulfite waste liquor, and 7 parts by weight of powdered silica gel,
and triturated in a hammer mill. By uniformly distributing the mixture in
water, a spray liquor is obtained.
vI. 3 parts by weight of compound no. 21 is intimately mixed with
97 parts by weight of particulate kaolin. A dust is obtained containing 3~0
by weight of the active ingredient.
VII. 30 parts by weight of compound no. 1 is intimately mixed with a
mixture consisting of 92 parts by weight of powdered silica gel and
8 parts by weight of paraffin oil which has been sprayed onto the surface
of this silica gel. A formulation of the active ingredient is obtained
having good adherence.
VIII. 40 parts by weight of compound no. 5 is intimately mixed with
10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-
formaldehyde condensate, 2 parts of silica gel and 48 parts of water to
give a stable aqueous dispersion. Dilution in water gives an aqueous
dispersion.
IX. 20 parts by weight of compound no. 25 is intimately mixed with
2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid,
8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight
of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate
and 68 parts by weight of a paraffinic mineral oil. A stable oily
dispersion is obtained.
2tl'~~_~87
15 O.Z. 0050/40637
In these application forms, the agents according to the invention may also
be present together with other active ingredients, for example herbicides,
insecticides, growth regulators, and fungicides, and may furthermore be
mixed and applied together with fertilizers. Admixture with other fun-
s gicides frequently results in an increase in the fungicidal spectrum.
For the following experiment, the active ingredient 2-(1,2,4-triazol-1-yl-
methyl)-2-(4-chlorophenyl)-3-(3-trifluoromethyl)-oxirane (A) disclosed in
EP-A 94,564 was employed.
Use Example
Action on Botrytis cinerea in pimientos
Pimiento seedlings of the "Neusiedler Ideal Elite" variety with 4 to 5
well developed leaves were sprayed to runoff with aqueous suspensions
containing (dry basis) 80% of active ingredient and 209'0 of emulsifier.
After the sprayed-on layer had dried, the plants were sprayed with a
conidial suspension of the fungus Botrytis cinerea and kept in a high-
humidity chamber at 22 to 24°C. After 5 days, the disease had spread on
the untreated control plants to such an extent that the necroses covered
the major portion of the leaves.
The results show that active ingredients nos. 1, 5, 21 and 25, applied as
0.05wt% spray liquors, had a better fungicidal action (0 - 10% attack)
than comparative agent A (80% attack).
35
