The invention provides agriculturally useful fungicidal phenylbenzamides of the formula ##STR1## wherein R.sub.1 and R.sub.2, which are identical or different, are each a hydrogen or halogen atom or an optionally halogenated alkyl radical having from 1 to 6 carbon atoms; and R.sub.3 and R.sub.4, which are identical or different, are each an alkyl radical having from 1 to 4 carbon atoms, or R.sub.3 and R.sub.4, taken together with the nitrogen atom to which they are attached, form a morpholino radical.

The present invention relates to new phenylbenzamide derivatives, their 
preparation, fungicidal compositions containing them and their use in 
protecting plants against fungal diseases. 
European Application No. 0,360,701 describes a very great number of amide 
derivatives and especially phenylbenzamides, as well as their use as 
active materials for controlling fungal diseases of plants. The examples 
show in particular their preventive activity against diseases such as 
mildews. 
Applicants have now discovered that a narrow selection of these derivatives 
have the properties already described but furthermore, and surprisingly, 
such an activity at an excellent level as well as a notable curative 
activity. 
More precisely, the present invention relates to phenylbenzamide 
derivatives of the formula: 
##STR2## 
wherein R.sub.1 and R.sub.2, which are identical or different, are each a 
hydrogen or halogen atom or an optionally halogenated alkyl radical having 
from 1 to 6 carbon atoms; and R.sub.3 and R.sub.4, which are identical or 
different, are each an alkyl radical having from 1 to 4 carbon atoms, or 
R.sub.3 and R.sub.4 taken together with the nitrogen atom to which they 
are attached form a morpholino radical. 
The optionally halogenated alkyl radical represented by R.sub.1 and/or 
R.sub.2 preferably has from 1 to 4 carbon atoms. 
A preferred group of compounds encompassed by formula (I) are the compounds 
in which R.sub.1 and R.sub.2, which are identical or different, are each a 
hydrogen or chlorine atom or a trifluoromethyl radical. 
Particularly preferred compounds encompassed by formula (I) are the 
compounds in which one of R.sub.1 and R.sub.2 is a hydrogen atom and the 
other of R.sub.1 and R.sub.2 is a trifluoromethyl radical; and the 
compounds in which R.sub.1 and R.sub.2 are each a chlorine atom. 
Another preferred group of compounds encompassed by formula (I) are the 
compounds in which R.sub.3 and R.sub.4, which are identical or different, 
are each a methyl or ethyl radical. 
Yet another preferred group of compounds encompassed by formula (I) are the 
compounds in which R.sub.3 and R.sub.4, taken together with the nitrogen 
atom to which they are attached, form a morpholino radical. 
Especially preferred compounds of the invention are the following: 
(1) N,N-Diethyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamide; 
(2) 2-(3,4-dimethoxyphenyl)-4-trifluoromethyl-1-morpholinocarbonylbenzene; 
(3) N-Ethyl-N-methyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamide; 
(4) N-Ethyl-N-methyl-2-(3,4-dimethoxyphenyl)-3,4-dichlorobenzamide; and 
(5) N,N-Diethyl-2-(3,4-dimethoxyphenyl)-3,4-dichlorobenzamide. 
The compounds of formula (I) can be prepared according to the process 
described in the aforementioned European Application No. 0,360,701, or 
according to one of the two other processes described below. 
According to a first process, the compounds of formula (I) above can be 
prepared from the corresponding compounds of the formula 
##STR3## 
after activation of the acidic functional group by treating said formula 
(II) compounds with a suitable activating agent preferably thionyl 
chloride (SOCl.sub.2), phosphoryl chloride (POCl.sub.3), phosphorus 
trichloride or pentachloride (PCl.sub.3, PCl.sub.5), 
dicyclohexylcarbodiimide, carbonyldiimidazole, a lower alkyl chloroformate 
(e.g. methyl chloroformate), trifluoroacetic anhydride or the like! and 
then reacting the resultant intermediate with an amine of the formula 
HNR.sub.3 R.sub.4 in the presence of an organic or inorganic base in an 
organic solvent (preferably a chlorinated or aromatic solvent or an ether 
such as THF). 
The compounds of formula (II) above can be prepared by saponifying the 
corresponding compounds of the formula 
##STR4## 
wherein R is an aliphatic radical, preferably an alkyl radical having 1 to 
4 carbon atoms. The reaction is carried out in an aliphatic alcohol such 
as ethanol in the presence of water and an inorganic base derived from an 
alkali metal (preferably an alkali metal hydroxide such as potassium 
hydroxide or sodium hydroxide), at a temperature from about room 
temperature to the reflux temperature of the reaction mixture. The 
reaction mixture is then treated with an organic or inorganic acid, such 
as, preferably, hydrochloric acid, to afford the corresponding compound of 
formula (II). 
The compounds of formula (III) can be prepared by an aryl coupling reaction 
between the compounds of the formula 
##STR5## 
and 3,4-dimethoxyphenylboronic acid in the presence of a catalyst such 
as, for example, tetrakis(triphenyl-phosphine)palladium!. In order to 
provide good selectivity, it is understood that neither R.sub.1 nor 
R.sub.2 may be a bromine or iodine atom. 
3,4-Dimethoxyphenylboronic acid can be prepared by analogy to methods 
described in the literature, for example Organic Synthesis, Coll. Vol. 4, 
page 68 or Journal of Organic Chemistry, 49, pp. 5237-5243. 
The esters of formula (IV) can be prepared by esterifying the corresponding 
acids of the formula 
##STR6## 
by reaction with an aliphatic alcohol ROH wherein R is preferably an alkyl 
radical having 1 to 4 carbon atoms, such as methanol or ethanol, in the 
presence of a suitable amount (typically from 1 to 20%) of an inorganic 
acid, such as gaseous hydrochloric acid or concentrated sulfuric acid, 
generally at the reflux temperature of the reaction mixture. The product 
can be isolated by precipitation in water or extraction using an organic 
solvent. 
The acids of formula (V) can be prepared by diazotization of the 
corresponding anthranilic acids of the formula 
##STR7## 
according to known methods. 
The preparation of the anthranilic acids of formula (VI) is amply described 
in the literature. 
In a second process, the compounds of formula (I) can be prepared from the 
corresponding compounds of the formula 
##STR8## 
by coupling with 3,4-dimethoxyphenylboronic acid, analogously in all 
respects to the process described above for the preparation of the 
compounds of formula (III) from the corresponding compounds of formula 
(IV). 
The compounds of formula (VII) can be prepared from the corresponding 
compounds of the formula 
##STR9## 
by a process analogous in all respects to the process described above for 
the preparation of the compounds of formula (I) from the corresponding 
compounds of formula (II).

In order to further illustrate the present invention and the advantages 
thereof, the following specific examples are given, it being understood 
that same are intended as illustrative and in nowise limitative. 
EXAMPLE 1 
N,N-Diethyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamide (Compound 
No. 1) (Formula I with R.sub.1 .dbd.H, R.sub.2 .dbd.CF.sub.3, R.sub.3 
.dbd.R.sub.4 .dbd.C.sub.2 H.sub.5). 
500 ml of 1,2-dichloroethane, 60 g (0.184 mol) of 
2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoic acid and 5 ml of 
N,N-dimethylformamide are introduced successively into a 1000 ml 
round-bottomed flask. 20 ml of thionyl chloride (0.276 mol) are then run 
in dropwise with stirring and while cooling at 0.degree. C. When the 
addition is finished, the reaction mixture is heated progressively to 
55.degree. C. over 2 hours and then evaporated to dryness. The residue is 
taken up in 200 ml of tetrahydrofuran and then poured dropwise into a 
solution containing 58 ml (0.55 mol) of diethylamine in 200 ml of 
tetrahydrofuran maintained at a temperature below 10.degree. C. When the 
addition is finished, the reaction mixture is stirred at room temperature 
for one hour and then evaporated to dryness. The residue is taken up in 
dichloromethane and washed successively with 1N HCl and distilled water. 
After drying over magnesium sulfate, the organic phase is evaporated under 
reduced pressure to provide 62.3 g (yield: 89%) of 
N,N-diethyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamide in the 
form of a white solid melting at 109.degree.-110.degree. C. 
The two compounds below were prepared analogously: 
2-(3,4-dimethoxyphenyl)-4-trifluoromethyl-1-morpholinocarbonylbenzene: 60 g 
(82.5%) melting at 130.degree. C. (Compound No. 2) (Formula I with R.sub.1 
.dbd.H, R.sub.2 .dbd.CF.sub.3, R.sub.3 +R.sub.4 =morpholino). 
N-ethyl-N-methyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamide: 71.2 
g (81%) melting at 103.degree.-104.degree. C. (Compound No. 3) (Formula I 
with R.sub.1 .dbd.H, R.sub.2 .dbd.CF.sub.3, R.sub.3 .dbd.CH.sub.3, R.sub.4 
.dbd.C.sub.2 H.sub.5). 
EXAMPLE 2 
2-(3,4-Dimethoxyphenyl)-4-(trifluoromethyl)benzoic acid (Formula II with 
R.sub.1 .dbd.H, R.sub.2 .dbd.CF.sub.3). 
1000 ml of absolute ethanol, 290 g (0.82 mol) of ethyl 
2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoate and 170 ml (0.164 mol) 
of 10N sodium hydroxide solution are introduced successively into a 
2-liter round-bottomed flask. The reaction mixture is brought to reflux 
for two hours and then evaporated to dryness under reduced pressure. The 
residue is taken up in 2.5 liters of water and extracted successively with 
500 ml of ethyl acetate and 500 ml of pentane. 500 g of crushed ice are 
added to the aqueous phase which is then treated with an excess of 
concentrated hydrochloric acid. The precipitate which forms is filtered on 
sintered glass and then dried under a stream of air; there is thus 
obtained 240.5 g (yield: 90%) of 
2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoic acid in the form of a 
light-beige solid melting at 194.degree. C. 
EXAMPLE 3 
Ethyl 2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoate (Formula III with 
R.sub.1 .dbd.H, R.sub.2 .dbd.CF.sub.3, R.dbd.C.sub.2 H.sub.5). 
263 g (0.885 mol) of ethyl 2-bromo-4-(trifluoromethyl)benzoate, 750 ml of 
1,2-dimethoxyethane, 4 g of tetrakis(triphenylphosphine)palladium, 177 g 
(0.974 mol) of 3,4-dimethoxyphenylboronic acid and 1000 ml of a 2M aqueous 
sodium carbonate solution are introduced successively, under an inert 
atmosphere, into a four-liter round-bottomed flask. The reaction mixture 
is brought to reflux for fourteen hours and then evaporated to a third 
under reduced pressure. The reaction mixture is poured onto two liters of 
water; the precipitate which forms is filtered on sintered glass, rinsed 
with water and then dried under a stream of air. There is thus obtained 
294 g (yield: 94%) of ethyl 
2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoate in the form of a beige 
solid melting at 89.degree. C. 
EXAMPLE 4 
Ethyl 2-bromo-4-(trifluoromethyl)benzoate (Formula IV with R.sub.1 .dbd.H, 
R.sub.2 .dbd.CF.sub.3, R.dbd.C.sub.2 H.sub.5). 
238 g (0.885 mol) of 2-bromo-4-(trifluoromethyl)benzoic acid, 1000 ml of 
absolute ethanol and 100 ml of concentrated sulfuric acid are introduced 
successively into a 2-liter round-bottomed flask. The reaction mixture is 
brought to reflux for 6 hours and then poured, after cooling, onto 2.5 
liters of ice-cold water; the oil formed is extracted with ethyl acetate. 
The organic phase is successively washed with water, with 1N sodium 
hydroxide solution and then again with water. After drying over magnesium 
sulfate, the solvent is evaporated to provide 263 g (yield: 100%) of ethyl 
2-bromo-4-(trifluoromethyl)benzoate in the form of a yellow oil. 
EXAMPLE 5 
2-Bromo-4-(trifluoromethyl)benzoic acid (Formula V with R.sub.1 .dbd.H, 
R.sub.2 .dbd.CF.sub.3). 
205 g (1 mol) of 4-(trifluoromethyl)anthranilic acid, 600 ml of glacial 
acetic acid and 400 ml of 47% hydrobromic acid are introduced successively 
into a three-liter round-bottomed flask. After dissolution, the reaction 
mixture is cooled to -10.degree. C., diluted with 400 ml of water and then 
treated dropwise with a solution of 69 g (1 mol) of sodium nitrite in 200 
ml of water while maintaining the temperature below 0.degree. C. When the 
addition is finished, the reaction mixture is stirred at 0.degree. C. for 
2 hours. This solution is run in dropwise into a six-liter reactor 
containing 143.5 g (1 mol) of cuprous bromide in 500 ml of 47% hydrobromic 
acid maintained at 60.degree. C. When the addition is finished, the 
reaction mixture is stirred at 60.degree. C. for one hour, cooled to room 
temperature and then poured into two liters of ice-cold water. The 
precipitate which forms is filtered on sintered glass, washed with water 
and then dried under a stream of air. There is thus obtained 216 g (yield: 
80%) of 2-bromo-4-(trifluoromethyl)benzoic acid in the form of a solid 
melting at 118.5.degree. C. 
The preparation of 4-(trifluoromethyl)anthranilic acid (Formula VI with 
R.sub.1 .dbd.H, R.sub.2 .dbd.CF.sub.3) used in Example 5 is described in 
the literature. 
EXAMPLE 6 
Second process: 
N-ethyl-N-methyl-2-(3,4-dimethoxyphenyl)-3,4-dichlorobenzamide (Compound 
No. 4) (Formula I with R.sub.1 .dbd.R.sub.2 .dbd.Cl, R.sub.3 
.dbd.CH.sub.3, R.sub.4 .dbd.C.sub.2 H.sub.5). 
12.4 g (0.040 mol) of N-ethyl-N-methyl-2-bromo-3,4-dichlorobenzamide, 100 
ml of 1,2-dimethoxyethane, 0.5 g of tetrakis(triphenylphosphine)palladium, 
8 g (0.044 mol) of 3,4-dimethoxyphenylboronic acid and 60 ml of a 2M 
aqueous sodium carbonate solution are introduced successively, under an 
inert atmosphere into a 500 ml round-bottomed flask. The reaction mixture 
is brought to reflux for fourteen hours and then evaporated to a third 
under reduced pressure. The reaction mixture is poured onto two liters of 
water; the precipitate which forms is filtered on sintered glass, rinsed 
with water and then dried under a stream of air. After purification by 
chromatography, there is thus obtained 10.3 g (yield: 70%) of 
N-ethyl-N-methyl-2-(3,4-dimethoxyphenyl)-3,4-dichlorobenzamide in the form 
of a white solid melting at 102.degree. C. 
The following compound was prepared analogously: 
N,N-diethyl-2-(3,4-dimethoxyphenyl)-3,4-dichlorobenzamide: 6.5 g (47.8%) 
melting at 108.degree. C. (Compound No. 5) (Formula I with R.sub.1 
.dbd.R.sub.2 .dbd.Cl, R.sub.3 .dbd.R.sub.4 .dbd.C.sub.2 H.sub.5). 
EXAMPLE 7 
N-Ethyl-N-methyl-2-bromo-3,4-dichlorobenzamide (Formula VII with R.sub.1 
.dbd.R.sub.2 .dbd.Cl, R.sub.3 .dbd.CH.sub.3, R.sub.4 .dbd.C.sub.2 
H.sub.5). 
200 ml of 1,2-dichloroethane, 14 g (0.052 mol) of 
2-bromo-3,4-dichlorobenzoic acid and 2 ml of N,N-dimethylformamide are 
introduced successively into a 500 ml round-bottomed flask. 11.5 ml of 
thionyl chloride (0.078 mol) are then run in dropwise with stirring and 
while cooling at 0.degree. C. When the addition is finished, the reaction 
mixture is heated progressively to 55.degree. C. over 2 hours and then 
evaporated to dryness. The residue is taken up in 50 ml of tetrahydrofuran 
and then poured dropwise into a solution containing 13 ml (0.15 mol) of 
N-methylethylamine in 50 ml of tetrahydrofuran maintained at a temperature 
below 10.degree. C. When the addition is finished, the reaction mixture is 
stirred at room temperature for one hour and then evaporated to dryness. 
The residue is taken up in dichloromethane and washed successively with 1N 
HCl and distilled water. After drying over magnesium sulfate, the organic 
phase is evaporated under reduced pressure to provide 12.4 g (yield: 80%) 
of N-ethyl-N-methyl-2-bromo-3,4-dichlorobenzamide in the form of a white 
solid melting at 71.degree. C. 
The following compound was prepared analogously: 
N,N-diethyl-2-bromo-3,4-dichlorobenzamide (Formula VII with R.sub.1 
.dbd.R.sub.2 .dbd.Cl, R.sub.3 .dbd.R.sub.4 .dbd.C.sub.2 H.sub.5): 13.6 g 
(yield: 83.7%). 
The preparation of 2-bromo-3,4-dichlorobenzoic acid (Formula V with R.sub.1 
.dbd.R.sub.2 .dbd.Cl) used in Example 7 was carried out as above in 
Example 5: the product was obtained in the form of a beige powder, 63 g 
(yield: 81%), melting at 196.degree. C. 
EXAMPLE 8 
In vivo curative test under glass on grape downy mildew (Plasmopara 
viticola): 
Vine cuttings (Vitis vinifera), of Chardonnay variety, are grown in pots. 
When these seedlings are 2 months old (8 to 10-leaf stage, height of 20 to 
30 cm), they are infected, by spraying, with an aqueous suspension of 
spores of Plasmopara viticola, responsible for grape downy mildew, at a 
concentration of approximately 5 ml/seedling (or approximately 
1.times.10.sup.5 spores per seedling). 
After this infection, the vine seedlings are incubated for two days at 
approximately 18.degree. C. in an atmosphere saturated with moisture and 
then for five days at approximately 20.degree.-22.degree. C. under 90-100% 
relative humidity. 
The infected plants are then treated, by spraying, with an aqueous 
suspension or solution of the material to be tested, at the desired 
concentration and containing a condensate of 20 molecules of ethylene 
oxide with sorbitan monooleate to a limit of half the active material 
concentration. Each vine seedling receives approximately 5 ml of the 
solution or dispersion. The treatment is carried out on two seedlings for 
each concentration of active material to be tested. Contaminated 
seedlings, used as controls, are treated with a solution which does not 
contain active material but which contains the same condensate of ethylene 
oxide with sorbitan monooleate at an identical concentration. 
After drying for 24 hours, the results obtained in the case of the 
seedlings treated with the active material to be tested are compared with 
those obtained in the case of the seedlings used as controls. 
Under these conditions, it is observed that, at a dose of 110 ppm (0.11 
g/l), Compounds 1 to 5 led to at least 95% inhibition in the development 
of the fungus, i.e. an activity equivalent to that of the commercial 
reference cymoxanil, taken under the same conditions. 
These examples illustrate well the fungicidal properties of the compounds 
according to the invention. 
The latter may, in effect, be used as fungicidal active materials, in 
particular for controlling fungal diseases of plants, especially those due 
to pathogenic fungi, especially those of the Oomycetes family of the 
Phytophthora sp type, for example Phytophthora infestans (potato or tomato 
late blight), Phytophthora citrophthora, Phytophthora capsici, 
Phytophthora cactorum, Phytophthora palmivora, Phytophthora cinnamoni, 
Phytophthora megasperma, or Phytophthora parasitica, Peronospora sp type 
(especially tobacco downy mildew), Plasmopara sp type, especially 
Plasmopara viticola (grape downy mildew) and Plasmopara halstedei 
(sunflower downy mildew), Pseudoperonospora sp type (especially downy 
mildew of the Cucurbitaceae and hop downy mildew), or Bremia lactucae type 
(lettuce downy mildew), as well as soil fungi. 
They are advantageously applied at doses of 0.01 to 5 kg/ha, and more 
specifically of approximately 0.02 to 2 kg/ha. 
For their practical use, the compounds according to the invention are 
rarely used on their own. Most often they form part of compositions. These 
compositions, which can be used for protecting plants against fungal 
diseases or in plant growth regulatory compositions, contain, as active 
material, at least one compound according to the invention as described 
above in combination with solid or liquid inert vehicles which are 
acceptable in agriculture, and/or surface-active agents which are 
compatible with the active material and which are also acceptable in 
agriculture. In particular, the customary inert vehicles and the customary 
surface-active agents can be used. 
The term "vehicle", in the present account, means a natural or synthetic, 
organic or inorganic material with which the active material is combined 
in order to facilitate its application to the plant, to seeds or to the 
soil. This vehicle is therefore generally inert and it has to be 
acceptable in agriculture, especially to the treated plant. The vehicle 
can be solid (clays, natural or synthetic silicates, silica, resins, 
waxes, solid fertilizers, and the like) or liquid (water, alcohols, 
ketones, petroleum fractions, aromatic or paraffinic hydrocarbons, 
chlorinated hydrocarbons) or gaseous. 
The surface-active agent can be an emulsifying, dispersing or wetting agent 
of ionic or nonionic type. There may be cited, for example, salts of 
poly(acrylic acids), salts of lignosulfonic acids, salts of phenolsulfonic 
or naphthalenesulfonic acids, polycondensates of ethylene oxide with fatty 
alcohols or fatty acids or fatty amines, substituted phenols (especially 
alkylphenols or arylphenols), salts of esters of sulfosuccinic acids, 
derivatives of taurine (especially alkyltaurates) and phosphoric esters of 
polycondensates of ethylene oxide with alcohols or phenols. The presence 
of at least one surface-active agent is generally indispensable where the 
active material and/or the inert vehicle are not soluble in water and 
where the vector agent of the application is water. 
The compositions used in the invention can be in fairly diverse, fluid, 
liquid or solid forms. 
As fluid composition forms, or liquids, there may be mentioned especially 
emulsifiable concentrates, emulsions, aqueous suspension concentrates, 
pastes, solutions, in particular water-soluble concentrates, concentrated 
solutions in an organic medium (ULV solution), and aerosols. 
The emulsifiable or soluble concentrates most often comprise 10 to 80% of 
active material, while the ready-to-apply solutions or emulsions contain, 
for their part, 0.001 to 20% of active material. In addition to the active 
material and the solvent, the emulsifiable concentrates can contain, when 
this is necessary, a suitable co-solvent and 2 to 20% of suitable 
additives such as stabilizing agents, penetration agents, corrosion 
inhibitors, dyes or adhesives. 
It is possible, by diluting these concentrates with water, to obtain 
emulsions of any desired concentration which are particularly suitable for 
application to crops. 
By way of examples, the composition of several emulsifiable concentrates 
will now be given: 
______________________________________ 
EC Example 1: 
active material (Compound No. 1) 
250 g/l 
epoxidized vegetable oil 
25 g/l 
mixture of alkylarylsulfonate 
100 g/l 
and of ether of polyglycol and 
fatty alcohols 
dimethylformamide 50 g/l 
xylene 575 g/l 
EC Example 2: 
active material (Compound No. 2) 
400 g/l 
alkaline dodecylbenzenesulfonate 
24 g/l 
condensate of 10 molecules of ethylene 
16 g/l 
oxide with nonylphenol 
cyclohexanone 200 g/l 
aromatic solvent qs for 1 liter 
______________________________________ 
It is possible, by diluting these concentrates with water, to obtain 
emulsions of any desired concentration which are particularly suitable for 
application to leaves. 
The suspension concentrates, which can also be applied by spraying, are 
prepared so as to produce a stable fluid product which does not settle out 
and they generally contain from 10 to 75% of active material, from 0.5 to 
15% of surface-active agents, from 0.1 to , 10% of thixotropic agents, 
from 0 to 10% of suitable additives, such as antifoaming agents, corrosion 
inhibitors, stabilizing agents, penetration agents and adhesives and, as 
vehicle, water or an organic liquid in which the active material has 
little or no solubility: certain solid organic materials or inorganic 
salts can be dissolved in the vehicle to help in preventing sedimentation 
or as antifreeze for the water. 
By way of example, the composition of a number of aqueous suspension 
concentrates will now be given: 
______________________________________ 
ASC Example 1: 
An aqueous suspension is prepared comprising: 
active material (Compound No. 3) 
100 g/l 
wetting agent (polycondensate of 
5 g/l 
ethylene oxide with alkylphenol) 
dispersing agent (Na naphthalene 
10 g/l 
sulfonate) 
antifreeze (propylene glycol) 
100 g/l 
thickening agent (polysaccharide) 
3 g/l 
biocide (formaldehyde) 1 g/l 
water q.s. for 1 liter 
ASC Example 2: 
An aqueous suspension is prepared comprising: 
active material (Compound No. 4) 
250 g/l 
wetting agent (polycondensate of 
10 g/l 
ethylene oxide with a C13 synthetic 
alcohol) 
dispersing agent (sodium 15 g/l 
lignosulfonate) 
antifreeze (urea) 50 g/l 
thickening agent (polysaccharide) 
2.5 g/l 
biocide (formaldehyde) 1 g/l 
water q.s. for 1 liter 
ASC Example 3: 
An aqueous suspension is prepared comprising: 
active material (Compound No. 5) 
500 g/l 
wetting agent (polycondensate of 
10 g/l 
ethylene oxide with a C13 synthetic 
alcohol) 
dispersing agent (salified phosphate 
50 g/l 
of a condensate of ethylene oxide 
with polyarylphenol) 
antifreeze (propylene glycol) 
100 g/l 
thickening agent (polysaccharide) 
1.6 g/l 
biocide (sodium salt of methyl 
3.3 g/l 
4-hydroxybenzoate) 
water q.s. for 1 liter 
______________________________________ 
There may be mentioned, as solid composition forms, powders for dusting 
(containing the active materials at a content of up to 100%) and granules, 
especially those obtained by extrusion, by compacting, by impregnation of 
a granulated vehicle, or by granulation from a powder (the content of the 
compound of formula (I) in these granules being between 0.5 and 80% for 
the latter cases). 
The wettable powders (or sprayable powders) are generally prepared so that 
they contain 10 to 95% of active material, and they generally contain, in 
addition to the solid vehicle, from 0 to 5% of a wetting agent, from 3 to 
10% of a dispersing agent and, when necessary, from 0 to 10% of one or 
more stabilizing agents and/or other additives, such as penetration 
agents, adhesives, or anti-caking agents, dyes, and the like. 
By way of example, the composition by weight of a number of wettable 
powders will now be given: 
______________________________________ 
WP Example 1: 
active material (Compound No. 1) 
10% 
condensate of 8 to 10 mol of ethylene 
0.75% 
oxide with C13 branched-type synthetic 
oxo alcohol (wetting agent) 
neutral calcium lignosulfonate 
12% 
(dispersing agent) 
calcium carbonate (inert filler) 
qs for 100% 
WP Example 2: 
active material (Compound No. 2) 
50% 
condensate of ethylene oxide with 
2.5% 
fatty alcohol (wetting agent) 
condensate of ethylene oxide with 
5% 
styrylphenol (dispersing agent) 
chalk (inert vehicle) 42.5% 
______________________________________ 
WP Example 3 
The same ingredients are used as in the above example, in the proportions 
below: 
______________________________________ 
active material (Compound No. 2) 
75% 
wetting agent 1.5% 
dispersing agent 8% 
calcium carbonate (inert filler) 
qs for 100% 
______________________________________ 
______________________________________ 
WP Example 4: 
active material (Compound No. 3) 
90% 
condensate of ethylene oxide with 
fatty alcohol (wetting agent) 
4% 
condensate of ethylene oxide with 
styrylphenol (dispersing agent) 
6% 
______________________________________ 
In order to obtain these sprayable powders or wettable powders, the active 
material is intimately mixed in suitable mixers with the additional 
substances and the mixture is milled in mills or other suitable grinders. 
Sprayable powders are thereby obtained whose wettability and 
suspensibility are advantageous; they can be suspended in water at any 
desired concentration, and this suspension can be used very advantageously 
in particular for application to plant leaves. 
The compounds of formula (I) can also be used in the form of powders for 
dusting; it is also possible to use a composition comprising 50 g of 
active material and 950 g of talc; it is also possible to use a 
composition comprising 20 g of active material, 10 g of finely divided 
silica and 970 g of talc; these constituents are mixed and milled and the 
mixture is applied by dusting. 
The granules for dusting have sizes between 0.1 and 2 mm and can be 
manufactured by agglomeration or impregnation. In general, the granules 
contain 0.5 to 25% of active material and 0 to 10% of additives such as 
stabilizing agents, slow-release modifying agents, binders and solvents. 
Two examples of granule compositions will now be given: 
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G Examples 1 and 2: 
active material (Compound No. 4) 
50 g 200 g 
propylene glycol 50 g 50 g 
cetyl polyglycol ether 2.5 g 2.5 g 
polyethylene glycol 35 g 35 g 
kaolin (particle size: 0.3 to 
0.8 mm) 910 g 760 g 
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The compounds according to the invention may advantageously be formulated 
in the form of water-dispersible granules also included in the scope of 
the invention. 
These dispersible granules, with an apparent density generally of between 
approximately 0.3 and 0.6, have a particle size generally between 
approximately 150 and 2000, and preferably between 300 and 1500 microns. 
The active material content of these granules is generally between 
approximately 1% and 90%, and preferably between 25% and 90%. 
The remainder of the granule is essentially composed of a solid filler and 
optionally of surface-active adjuvants which confer water-dispersibility 
properties on the granule. These granules can be essentially of two 
distinct types depending upon whether the filler used is water-soluble; it 
can be inorganic and, preferably, organic. Excellent results have been 
obtained with urea. In the case of an insoluble filler, the latter is 
preferably inorganic, such as, for example, kaolin or bentonite. It is 
then accompanied by surface-active agents (in an amount of 2 to 20% by 
weight of the granule), surface-active adjuvants of which more than half 
consists of at least one essentially anionic dispersing agent such as a 
poly(alkali metal or alkaline-earth metal naphthalene sulfonate) or alkali 
metal or alkaline-earth metal lignosulfonate, the remainder consisting of 
nonionic or anionic wetting agents such as an alkali metal or 
alkaline-earth metal alkylnaphthalene sulfonate. 
Moreover, although this is not indispensable, it is possible to add other 
adjuvants such as antifoaming agents. 
The granule according to the invention can be prepared by mixing the 
required ingredients and then granulating according to several techniques 
known per se (pelletizer, fluid bed, atomizer, extrusion, and the like). 
Generally, the preparation is completed by crushing followed by sieving to 
the particle size chosen within the abovementioned limits. 
Preferably, it is obtained by extrusion. By carrying out the preparation as 
shown in the examples below, the following dispersible-granule 
compositions were prepared. 
DG Example 1 
90% by weight of active material (Compound No. 5) and 10% of urea in the 
pearl form are mixed in a mixer. The mixture is then milled in a pin mill. 
A damp powder is obtained which is extruded in a perforated-cylinder 
extruder. A granule is obtained which is dried and then crushed and sieved 
so as to retain only the granules with a size of between 150 and 2000 
microns respectively. 
DG Example 2 
The following constituents are mixed in a mixer: 
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active material (compound No. 2) 
75% 
wetting agent (sodium alkylnaphthalene 
2% 
sulfonate) 
dispersing agent (sodium polynaphthalene 
8% 
sulfonate) 
water-insoluble inert filler (kaolin) 
15% 
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______________________________________ 
DG Example 3: 
active material (Compound No. 1) 
20% 
sodium alkylnaphthalene sulfonate 
2% 
sodium methylenebis(naphthalene 
sulfonate) 8% 
kaolin 70% 
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This mixture is granulated in a fluid bed, in the presence of water, and is 
then dried, crushed and sieved so as to produce granules of between 0.16 
and 0.40 mm in size. 
These granules can be used alone or in solution or dispersion in water so 
as to produce the required dose. They can also be used to prepare 
combinations with other active materials, especially fungicides, the 
latter being in the form of wettable powders or of granules or aqueous 
suspensions. 
The compounds according to the invention can also be formulated in the form 
of organic solutions which can be encapsulated, especially by interfacial 
polymerization, in capsules having polymeric walls, for example based on 
polyamides, polyureas or urea polyamides. These capsules are found in the 
form of a concentrated aqueous dispersion which can be diluted at the time 
of use to produce a spraying mixture. 
As has already been said, the aqueous dispersions and emulsions, for 
example compositions obtained by diluting a wettable powder or an 
emulsifiable concentrate according to the invention using water, are 
included within the general scope of the compositions which can be used in 
the present invention. The emulsions can be of water-in-oil or 
oil-in-water type and they can have a thick consistency like that of a 
"mayonnaise". 
The invention moreover relates to a process for the treatment, both 
curative and preventive, of plants against diseases caused by 
phytopathogenic fungi especially those of the Oomycetes family of the 
Phytophthora sp type, for example Phytophthora infestans (potato or tomato 
late blight), Phytophthora citrophthora, Phytophthora capsici, 
Phytophthora cactorum, Phytophthora palmivora, Phytophthora cinnamoni, 
Phytophthora megasperma, or Phytophthora parasitica, Peronospora sp type 
(especially tobacco downy mildew), Plasmopara sp type, especially 
Plasmopara viticola (grape downy mildew) and Plasmopara halstedei 
(sunflower downy mildew), Pseudoperonosora sp type (especially downy 
mildew of the Cucurbitaceae and hop downy mildew), or Bremia lactucae type 
(lettuce downy mildew), as well as soil fungi, this process being 
characterized in that a derivative according to the invention is applied. 
The excellent curative activity of the compounds according to the 
invention is particularly advantageous since it makes it possible to 
reduce the number of systemic preventive treatments while providing good 
control of parasites. 
These derivatives can be used as the sole active material or in combination 
with another agrochemically active material, especially a fungicide such 
as, for example, those of the thiocarbamate or 
ethylenebis(dithiocarbamate) family, such as thiram, maneb, zineb and 
mancozeb, the phthalimide family, such as captan, captafol and folpet, the 
acylalanine family, such as metalaxyl, oxadixyl and benalaxyl, the family 
of copper-based compounds, the family of phosphonic acid derivatives such 
as fosetyl-aluminum, dithianon, chlorothalonil, cymoxanil, the thiadiazole 
family or the N,N'-dialkyl-N-phenylsufamide family. 
This process is characterized in that it comprises applying to plants or to 
the locus in which they grow an effective quantity of a compound of 
formula (I), especially by applying an anti-fungal composition containing, 
as active material, an effective quantity of a compound according to the 
formula (I). "Effective quantity" is understood to mean a quantity 
sufficient to make possible control or destruction of the fungi present on 
these plants, in a curative as well as in a preventative sense, i.e. a 
fungicidally effective amount. The use doses can, however, vary within 
wide limits depending on the fungus to be combated, the type of crop, the 
climatic conditions and depending on the compound used. 
In practice, doses ranging from 1 g/hl to 500 g/hl, corresponding 
substantially to doses of active material per hectare of approximately 10 
g/ha to 5000 g/ha, generally give good results. 
There may be mentioned, as examples of treatment processes which can be 
used, leaf or soil spraying, dusting, soaking, incorporation into the soil 
of granules, powders or mixtures, sprinkling, injection into trees, 
painting and seed treatment. 
While the invention has been described in terms of various preferred 
embodiments, the skilled artisan will appreciate that various 
modifications, substitutions, omissions and changes may be made without 
departing from the spirit thereof. Accordingly, it is intended that the 
scope of the present invention be limited solely by the scope of the 
following claims, including equivalents thereof.