FONGICIDES

FUNGICIDAL FORMULATIONS

Abrégé anglais

ABSTRACT
Fungicidal formulations are described which comprises as a first fungicidally
active ingredient a triazole or pyrimidine of formula :-
<IMG> or <IMG>
I(a) I(b)
where X is chlorine or fluorine and as a second fungicidally active
ingredient a compound of formula :
<IMG> or <IMG>
II(a) II(b)
where R is fur-2-yl or -CH2OCH3, associated with one or more inert non-
phytotoxic carrier(s) therefor. Fungicidal methods employing such
formulations are also described.

Revendications

CLAIMS
1. A fungicidal formulation comprising as a first fungicidally active
ingredient a triazole or pyrimidine of formula :-
<IMG> or <IMG>
I(a) I(b)
where X is chlorine or fluorine, and as a second fungicidally active
ingredient a compound of formula :
<IMG> or <IMG>
II(a) II(b)
where R is fur-2-yl or -CH2OCH3, associated with one or more inert, non-
phytotoxic carrier(s) therefor.
2. A fungicidal formulation according to claim 1 comprising a compound
of formula I(a) and a compound of formula II(a), said compound
of formula I(a) and said compound of formula II(a) being present
in the ratio range of 5:1 to 1:250 by weight.
11

3. A fungicidal formulation according to claim 1
comprising a compound of formula I(a) and a compound of
formula II(b), said compound of formula I(a) and said
compound of formula II(b) being present in the ratio range
of 5:1 to 1:250 by weight.
4. A fungicidal formulation according to claim 1
comprising a compound of formula I(b) and a compound of formula
II(a), said compound of formula I(b) and said compound of
formula II(a) being present in the ratio range of 5:1 to
1:250 by weight.
5. A fungicidal formulation according to claim 1
comprising a compound of formula I(b) and a compound of
formula II(b), said compound of formula I(b) and said compound
of formula II(b) being present in the ratio range of 5:1 to
1:250 by weight.
6. A method of treating fungal infections of plants
which comprises applying to said plants a fungicidally
effective amount of a fungicidal formulation as claimed in
claim 1.
7. A method according to claim 7 which comprises applying
the formulation to grapes.
8. A method according to claim 6 in which the
fungicidal formation is applied as a foliar spray, said
compound of formula I(a) being used at an application rate of
from 10 to 500 grams per hectare, amd said compound of
formula I(b) being used at an application rate of from 10 to
100 grams per hectare.
9. A method according to claim 8 in which the compound
of formula II(a) is applied at a rate of from 100 to 2,500 g
per hectare, and in which the compound of formula II(b) is
applied or a rate of from 50 to 500 g per hectare.
12

Description

This invention relates to fungicidal formulations and to methods
of treating fungal infections of cultivated plants.
According to one aspect of the present invention, there is provided
a fungicidal formulation comprising as a first~fungicidally active ingredie t
a triazole or pyrimidine of formula :-
r'lD ' ~ ~\`Cl
Cl ~ O-CH-CO-C(CH3)3 ~ ~ C OH
I(a) ~ l(b)
. X
where X is chlor1ne or fluorine ? and as a second fungicidally active
- ingrçdient a compound of formula : - .
; 20 CIH3 0 ll
N or C2H5NH~NHCCCN
\ CO - R NOCH3 .
II(a) II(b)
25where R is fur-2-yl or -CH20CH3,
. associated with one or more inert, non-phytotoxic carrier(s) therefor.
A11 of the aforementioned compounds are known compounds and may be
prepared by methods well-defined in the literature. The triazole of formula
I(a) is described in U.S. Patent Specification No. 3,912,752, the pyrimidines
of formula I(b) in U.K. Patent Specification No. 1,218,623, the alanine
derivatives of formula II(a) in U.K. Patent Specification
.,
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.
No. 1,448,810 and 8elgian Patent Specification No. 827,57i and the urea
of formula II(b) in U.K. Patent Specification No. 1,470,740.
~ The combinations of active ingredients defined in the above formul-
; ation are novel and have been Found to be surprisingly effective in
controlling or combatting fungal infections of cultivated plants. They are
; of value in the treatment of a wide range of cultivate~ crops susceptible
to fungal attack, such as for example cereals an~ beans,
and in particular crops susceptible to powdery and downy mi1dew, as well
as late blight, i.e. crops such as grapes, cucurbits and tobacco susceptible
to attack by microorganisms of nomycestes an~ Erysiphales sp~cies
According to a second aspect of the invention, there is provided a
method of treating fungal infections of plants especially grapes
which comprises applying to said plants a fungicidally effective amount of a
fungicidal formulation as deFined above.
In the aforesaid method, the formulation can be applied by foliar
.. .. .. __ . .. . . ., . .. .
application or soil drench, depending on the crop being treated, at any
time after crop emergence until harvesting takes place. The amount and
frequency of application will be determined by the severity or expected
2~ severity of the fungal disease and, as is well known to those skilled in the
art, by the age and condition of the crop. However, it is a feature of the
invention and a particular advantage obtainçd therefrom that a reduced
frequency of treatment, for example only once evèry 2 to 3 weeks to control
; grape milde~l infections, may be effectively employed,thus achieving a
valuable reduction in labour costs.
I The preferred pyrimidine for use in foliar application for instance
¦, in grape treatment is that in which X is chlorine. However, when application
¦~ of the combination of the invention is to be effected by means of a soil
¦l drench it has been found that the pyrimidine of formula I in ~hich X is
3G I
i

fluorine is particularly efficacious.
As stated above, formulations of this invention are
applied by foliar application or by soil drench. In soil
drenches, the compounds Of formula I (a) and I (b) are preferably
applied in an amount of from 50 to 500g per hectare, whereas
the compounds of formula II(a) are preferably applied in amounts
of from 500 to 3000g per hectare. Thus the ratio of compounds
of formula I to compounds of formula II(a) in such formulations
may preferably range from 1:1 to 1:60 by weight.
When foliar application is utilised the compound of
formula I(a) is preferably applied at a rate of from 10 to
500g per hectare, whereas the compounds of formula I(b) are
preferably applied at a rate of from 10 to lOOg per hectare.
The compound of formula II(a) is preferably applied at a rate
of from 100 to 2,500g per hectare. In such circumstances, the
compound of formula II(b) is preferably applied at a rate of
from 50 to 500g/hectare. Accordingly, the ratio of compounds
of formula I to compounds of formula II in formulations applied
by foliar application is preferably from 5:1 to 1:250 by weight.
The formula II(b) compound is preferably used in com-
bination with a further fungicide, such as for example zineb or
; mancozeb, and as specified in U.K. Patent Specification No.
1,470,740. It should be noted that such further fungicides
are used at approximately half their normal rate and that the
compound of formula II(b) is not compatible with compounds
which increase alkalinity.
In order to simplify manufacture, storage and trans-
port, the combinations of the formulae I and II compounds will
be normally produced in concentrate from intended for dilution
in water to the degree necessary to enable the above mentioned
application rates to be easily achieved. Such concentrated
formulations may contain from 0.5 to 90%, preferably 5 to 90%,
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by weight of active ingredients associated with one or more
inert non-phytotoxic carrier(s~ therefor. Such formulations
will usually be in the form of a wettable powder or dust,
aqueous suspension, emulsifiable concentrate or granules.
The concentrate formulations are intended for appropriate
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385~
dilution with water prior to use. This formation of an aqueous dispersion
can be carried out in conventional spray tanks suitable for the purpose.
It is to be clearly understood that the diluted formulations so produced are
formulations in accordance with the invention in which one or all of the
inert non-phytotoxic carrier(s) is water.
Wettable powders or dusts comprise an intimate mixture of the active
ingredients, one or more inert carriers and appropriate surfactants. The
inert carrier may be chosen from the attapulgite clays, the montmorillonite
clays 9 the diatomaceous earths, kaolins, micas, talcs and purified silicates.
Effective surfactants may be found among the sulfonated lignins, the
naphthalene sulfonates and condensed naphthalene sulfonates, the alkyl
succinates, the alkylbenzene sulfonates~ the alkyl sulfates and nonionic
surfactants such as ethylene oxide adducts of phenol. Illustrative of
wettable powders falling within the scope of the invention are those having
the following composition :
Wettab1`e Powders
~ by weight
Formula I compound l to lO
Formula II compound 5 to 60
Surfactant(s) 0 to lO
Dispersing Agent 0 to lO
Anticaking agent 0 to 15
Inert carrier(s) to lO0
j The following non-limitative Examples will serve to further illustrate
i the invention.
The compound of formula I in which Y is chlorine is known as fenarimol,
whilst the related compound in which X is fluorine is kno~.~/n as nuarimol.
I Simil3rly, the compound of formula I(a) is known as triadimefon. In the
3û Examples below the compound of formula II(a) in which R is fur-2-yl is
represented by the letter "A", the formula II(a) compound in which
;l -5-
1, :

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R is -CH20CH3 by "B" and the formula II(b) compound by "C"
EXAMPLES l to lO
The following wettable powders were prepared :- ¦
(l) ~O by weight
Compound A 25
Fenarimol 5.0
Sodium lauryl sulphate 4.0
Sodium lignin sulphonate 3.0
Precipitated silica 8.0
- Kaolin clay to lOO.O
(2) ~0~ by weight
Compound A 50.0
Nuarimol 2.5
Sodium dioctyl sulphosuccinate 5.0
Sulphonated lign1n 2.0
Diatomaceous earth to lOO.O
: ~ . ~ ,
2û (3) ~O' by weiqht
Compound 8 40.0
Fenarimol 4.0
Ethoxylated alkyl phenol 3.0
Sodium lignin sulphonate 5.0
I Hydrated sodium silicoaluminate 4.0
I Talc to lOO.O
~l
1l -6-
1' .

1~2.~
ll
(4) O by weight
~uarimol 2.0
Compound B 40.û
Sodium alkylnaphthalene sulphonate a . o
Silica 3.0
Kaolin to lO0.0
(5) ~ by weight
Compound C 36.0
Fenarimol 6.0
Sodium alkyl ether sulphate 4.0
Sodium lignin sulphonate 3.0
Silica 7.0
. Attapulgite to 100~0
(6) . O by weight
Compound C 6.0
F~narimol l.0
Zineb 50.0
Sodium salt of condensed
naphthalene sulphonic acids 3.0
Sodium lignin sulphonate 4.0
Hydrated sodium silicoaluminate 8.0
Montmorillonite to lO0.0
(7) O by weight
Compound C 3.0
Fenarimol 0-5
Mancozeb 36.0
Sulphite lye powder 2.0
I Sodium laurylsulphate 5.0
I Silica 6.n
Kaolin to 100.0
_7_
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~ s~
(8) ,~ by weight
Compound A 40.0
Triadimefon lO.0
Ethoxylated nonyl phenol 5.0
Sodium lignin sulphonate 2.0
Silica 4.0
Talc to lO0.0
(9) ~ by weight
Compound B 50.0
Triadimefon lO.0
Sodium lauryl sulphate 2.0
Sodium salt of condensed naphthalene 4.0
Sulphonic acids
Precipitated silica 6.0
Kaolin to lO0.0
(lO) ~ ~ by weight
Compound C 30.0
Triadimefon lO.0
Sodium dioctyl sulphosuccinate 3.0
Sulphonated lignin 4.0
Hydrated sodium silicoaluminate 8.0
Attapulgite to lO0.0
In each of the above Examples, the active ingredients were carefully ¦
I blended with the specified excipients in conventional mlxing equipment.
¦ The blend was then further milled in a fluid energv mill to a size range
of from l to lO microns and finally the mixture was reblended and
deaerated prior to being packaged.
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The formulations described in Examples l,3 and 5 to lO are intendod
for use in foliar application whereas the formulations of Examples 2 and 4
are of value as soil drenches.
E~AMPLE ll
The following Example illustrates the typical synergistic activity
to be observed when combinations of the inventions are employed For control
of fungal organisms.
Solutions of fenarimol in water were prepared at a concentration of
lû and 20 parts per million and solutions of compound 8 at a concentration
of 50 andlOO parts per million. They were applied separately and together
to ll day old Pinto bean plants. . A single treatment consisted in
spraying 3 pats, each pot containing two plants.
When the plants had dried they were inoculated with a suspension of
spores of bean leaf rust and incubated for 48 hours in a cool moist chamber. ¦
The percentage control of the disease was then noted as follows :
_ . -
FENARIMOL CaMPOUND B Percentage
control by
(concentrate (percentage (concentrate (percentage combination of
p-p-m) disease p-p-m) disease fenarimol and
control) control) compound 8
~ _ _ _
6 62
lOO 29 85
77 50 6 95
77 lOO 29 96
. I . I
~5
I
I 'I
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When analysed by the well-known "Calby equation" ~see ~leeds ? 15,
20-22 (1967) the above results clearly showed that under the conditions
of the test,this mixture of the invention demonstrated synergism.
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