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(11) Pate. Number: ICE 291 (45) Date of grant: 12/01 /2009
--493_1111311
(19) Kenya Industrial Property Institute.
(12) PATENT
(51) Int.CLA: 01N 25124
(21)Application    KEPI 2001/ 000206    (84) WO No. WO 02/09517 Al
Number:    07/02/2002
(22)Filing Date:    19/07/2001
(31)Priority Number: 00/09898    (32) Date: 28/07/2001 (33) Country: FR
(73) Owner(s): Bayer Cropscience S.A. of 55, Avenue Rene Cassin - CP 106, F-69266 Lyon Cedex 09, France.
(72) Inventor(s)    Duvert, Patrice; Martinon, Isabelle and Buiret, Carinne
(74)Agent/address for correspondence: Hamilton Harrison & Mathews, P.O. Box 30333-00100,
Nairobi
(54) Title:    FUNGICIDAL COMPOSISTION COMPRISING IN PARTICULAR AN OIL OF
VEGETABLE ORIGIN WITH HIGH DRYING POWER
(57) Abstract: The invention concerns a fungicidal composition useful for treating fungal diseases of crops and comprising in particular at least a vegetable oil with high drying power, as well as a method for treating crops using said composition.
 
FUNGICIDAL COMPOSITION COMPRISING IN PARTICULAR AN OIL
OF PLANT ORIGIN WITH NIGH SICGATIVE POWER
The subject of the present invention is a fungicidal composition useful for the treatment of 5 fungal diseases of crops and which comprises a
vegetable Oil with high siccative power, and a method of treating Crops using a composition according to the invention.
It is always desirable to reduce the doses of 10 chemical products spread in the environment, for treating fungal diseases of crops, in particular by reducing the doses for application.
To do this, certain adjuvants, termed
biological activators such as mineral oils, wetting
15 agents and penetrating agents are combined with Commercial proprietaries, and now make it possible, for example, to combine a mineral oil-type adjuvant with fungicidal compounds, which has the advantage of reducing the applied dose of fungicidal compounds. This
20 thus broadens the possibilities of choices offered to farmers, so that the latter finds the solution best suited co their particular problem.
On the ether hand, the Ilse of some of these proprietaries is restricted when cases of phytotoxicity
25 are observed on 00,0111 cops,
One aim of the invention is therefore to provide a novel fungicidal composition, allowing better selectivity even on so-called sensitive crops, while
-3-
 
2
preserving an equivalent biological activity,
preventively or .cratively, against various diseases,
It has now been found that these aims Could be achieved using the fungicidal composition according 5 to the invention.
The subject of the present invention is a fungicidal composition useful for the treatment of fungal, diseases of crops, based on at least one
fungicidal compound and at least one adjuvant of the
10 oil- of plant origin type possessing high siccative
power, the latter acting as activator {doping agent). It also relates to a method of treating crops with the same aim.
in a first aspect, the present invention provide.
15 a, fungicidal composition, characterised in that it comprises at least one fungicidal compound A and at least one oil B, this all being of plant origin and possessing a
high siccative power, the compound's/compound A weight ratio being between 0,15 and 1.5.
20    In a second aspect, the present invention
provides a method of treatment intended for combating or preventing fungal diseases of crops, characterised in that an effective and non-phytotoxic dose of a composition according to the first aspect of the present invention is
25 applied to the aerial parts of the plants.
-4-
 
2a
In a third'aspect, the present invention provides a product for applying compounds A and B of the composition according to the first aspect of the present invention, wherein the dompOunds A and B are applied simultaneously, 5 sequentially Al alternately-
A Fairly large number of ekamp/e0 of the use of vegetable oils in formulations Al pesticidal, and in Particular fungicidal, compounds, axe known in the literature.
10    Nevertheless, no use 'of vegetable oils
possessing high siccative power in fungicidal compositions has ever been reported.
Thus, and most surprisingly, Such a Use in
fungicidal compositions according to the invention has
15 made it possible IC obtain particularly advantageous results.
The fungicidal compounds according to the present invention are, fox the most part, known to farmers in particular for their efficacy against the
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diseases affecting or likely to affect cereals and other crops.
Pne advantage is also noted with regard to the use of certain vegetable oils which make it
5 possible to reduce by 3 the dose of oil while preserving an equivalent biological efficacy.
Furthermore, the composition of the
formulation proposed makes it possible to obtain an excellent physical quality of the plant-protection
10 mixture for application and thus allows its use with various Other commercial combinations with no risk of physicochemical incompatibility.
Such a stability of the plant-protection mixture for application of the fungicidal composition
15 according to the invention also makes it possible to he able to formulate certain active substances whirl, are otherwise difficult or even impossible to formulate.
Another aim of the invention is to provide a novel fungicidal combination useful in the preventive
20 Of curative treatment of diseases.
Another aim of the invention is to provide a fungicidal combination allowing improved efficacy, preventively or curatively, against various diseases and/or improved selectivity.
25    Another aim if the invention is to improve,
in terms of persistence, the action of the fungicidal compounds.
-8-
 
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ST I purled.. IuppTbung eq. 'AItree;e,d
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4, axr -55100 an T110o5s 46T4 a buTscesded oTTo 0501aCee
;0 men op5o05as aria 01 pouuT5.016e3upppe. au
9.5 pp. 55.0 4010014    10e500 p puma:beep/Er purled..
'.0100 01514005e q6514 13-641seessod pue uT65,0 weld ;0 bvreq 150 .FG1    111 sue 314ay .0e pm 0 punode. 505415640; OT
ouo 10105 ue 10150004e. 35 0141 ier paoT,ageoleue 11 5005100e40
0. 03 6u5p,... 5.515sodued 5e05155013 141
.    oalleTwee uppq lent-
eery colym saCpcupopecTp pup sure-mold ay3 03 SU0T7l1T0e 0074ze0 00 egeTduroe sepToad 40.514 puce; .5101 mcu 5 Ge. .05.70d000 100005bun; g ,ATEUTSTIdanS
•    1.11-ea o, s4inot,200 uT 'eurrTuTetree Ieuupem aswoe 01 WUR,0i70 10410q 4.540 ..51005T01ee 40540001511. 05.15. 0041004
 
The invention therefore relates to a
fungicidal composition combining an oily organic phase 8 which is a selection of unsaturated vegetable oil, of isemerized oil, of vegetable oil enter, of
5 vegetable polymer and/or of a mixture of these various organic ghee..
The vegetable oils may be of various origins, but those derived from linseed, sunflower, soya bean, maize, cotton, safflower and rapeseed will be
10 preferred, These oils are available in various qualities, namely crude, refined or isomerired.
Preferably, the oil is a polyunsaturated vegetable oil which naturally contains a large number of unsaturatIons.
15    The expression polyunsaturated oil is
understood to mean a triglyceride in which thO majority of the linear fatty chains possess two or three double bonds per chain, noted C19,2 Sr 018,3, that is to say chains consisting of 18 carbon atoms with 2 or 3
20 unsaturations.
As examples of polyunsaturated oils, there coy be mention., triglYcerides which predominantly contain so-called linoleic 018:3) fatty acid chains such as linseed oil. As a guide, the ...Position by
25 weight of this oil, characterlied at fatty acids, may be within the following range: 50 to 60% of C18:3 - 10 to 17% of C10:2 - 15 to 25% of C18:1 - 2 to 44 of C18,0 - 5 to 8% of 016,0,
 
As an example of polyunsaturated oils, there may also be mentioned triglycerides predominantly containing fatty acid chains of the linoleic type (C18:2) such as sunflower, maize, soya bean, safflower,
5 cotton or rapeseed oil. As a guide, the composition of these oils, characterized as fatty acids, may be within the following range: 45 to 70% of C18:2 - 0.1 to 10% of 118:3 - 10 to 401 of 018:1 - 0.1 to 10% of C18:0 - 1 to 26% of 016:0.
10    In other words, the oil coming within the
scope of the present invention is said to be siccative. The siccativity is either natural isiccative or semi-siccative oils: or is obtained by chemical treatment of an oil which is not or not very siccative (so-called
15 semisiccative or nonsiccative oils), this oiI is then said to be isomerized.
The isomerization reaction consists in conjugating the double bonds in the fatty acid chain - CH-CH-CH2-01-1,0-, to as to obtain conjugated dienes as
20 follows - CH-CH-CF.-CH-082-, thus increasing their siccarivity (reactivity to air).
There may be mentioned, as isomerized oil, isomerized sunflower oil with a percentage of
conjugated dienes of between 16 and 161, but also 25 isomerized linseed oil containing 11 to 138 of conjugated dienes.
For the fungicidal composition according to the invention, the use of vegetable oils whose iodine
 
value linked to their siccative power is greater than 70, preferably greater than 90, more preferably Still greater than 130; most preferably greater Chan 150, is preferred.
, • In some embodiments, the present invention also relates to a combination of compounds A and B, such a combination is then a combination of two camoounda,.and may be
applied simultaneously as a ready-to-use mixture or as a freshly made-rektor'.
10    •    The compound 8/compound A weight ratio in the
composition according to the invention is
between 0.15 and .1.6, preferably between 0.2 and 1.35, more preferably still between 0.25 and 1, or
alternatively between 0.3 and 0.7, and most
15 advantageously 0.45.
This composition 'is useful for Ohs treatment of fungal diseases of various crops. It is thus effective for treating rust, leaf blotch, net blotch of barley, for treating eyespot, rust, septoria diseases,
20 yellow leaf spot and fusaria of wheat. It is also effective for controlling grey mould, alternarea leaf Spot, sclerotinia disease, not blotch and fossils of protein-rich Plants and of oil-producing plants (in particular pea, rapeseed and main) and for the
25 treatment of turf diseases such as rust, fusaria, scierotinia and Scut,
It Is particularly useful forethe treatment of grey mould of vine, vegetable crops, the peach tree,
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the almond tree, the apple tree, the pear tree, the rape plant, the pea, the haricot bean and citrus; alternaria diseases of vegetable crops, the peach tree, the almond tree, the apple tree, the pear tree, the 5 rape plant, potato and citrus; brown rot of the peach tree, the almond tree, the cherry tree; sc lerotinia disease of vegetable crops, the rape plant and potato: and scurf of vegetable crops and rice.
Compounds A, contained in the composition 10 according to the invention are described in at least one of the following manuals,
- "The pesticide manual!' edited by Clive TOMLIN and published by the British Crop Protection Council, 11th edition;
15    - 'I'Index phytosanitaire 200C., published by the
Association de Coordination Technique Agricole, 36th edition.
Compound B, also contained in the composition according to the invention, is preferably refined
20 and/or isomerired Sunflower oil.
For their practical use, compounds A and B of the composition according to the invention are rarely used alone.
In the fungicidal composition according to
25 the invention, compound, A and B most often represent from 0.5 to 95% by weight of the said composition as described above.
 
This may include the concentrated
composition, that is to say the commercial product combining the two active substances (for the purpOses
of the Present text, the expression active substance 5 _should be understood to mean both compound A, a
fungicidal compound, and compound a, an adjuvant). This
may also include the dilute composition ready to be sprayed on the crop to be treated. In the latter case, the dilution with water may be carried out either using
l0 a concentrated commerical composition containing the two active substances (this mixture is called "ready mix") or by means of the. fresh mixture .(called "tank mix") cf two•commercial eoncentraied compositions each containing one substance.
15    Typically the composition according to the
invention is liquid, and in this case in the form of a solution, suspension, emulsion or emulsifiable concentrate.
oil-aqueous liquid compositions are preferred both for their ease of use and the simplicity of their
20 manufacture. Preferably, an aqueous concentrated suspension is available which uses vegetable oil in the form of an oil-in-water emulsion.
More generally, the composition according to the invention may include any solid or liquid additives 25 corresponding to the customary techniques of
formulating plant-protection products.
The composition according to the inventien
may comprise, in addition, any customary additives or
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10
adjuvants of plant-protection compositions, in particular carriers, surfactants, adhering agents,
flow-enhancing agents and antigels. This composition may also contain any sort of other ingredients such as, 5 for example, protective colloids, adhesives,
thickeners, thixotropic agents, penetrating agents, stabilizers, Sequestrants, pigments, colorants, polymers and antifoams.
The term -carrie,' in the present text
10 denotes a natural or synthetic, organic or inorganic material with which the active substances are combined to facilitate their application to the plant. This carrier is therefore generally inert and should be agriculturally acceptable, in particular on the treated
15 plant. The carrier may be solid (clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, and the like) or liquid (water, alcohols, ketones, petroleum fractions, aromatic or paraffin hydrocarbons, chlorinated hydrocarbons, liquefied gases
20 and the like).
The surfactant may be an emulsifying,
dispersing or wetting agent of the ionic or nonionic type. There may he mentioned, for example, salts of polyacrylic acids, salts of lignosulphonic acids, salts
25 if phanoleulphonic or nauhthalenesulphonic attic,
polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in particular alkylphenols or arylphenols),
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11
salts of esters of sulphosuccinic acids, derivatives of taurine (in particular alkyl taucateS), phosphoric esters of polyoxyethylated alcohols or phenols. The presence of at least one surfactant is desirable to 5 promote the dispersion of the active substances in water and their good application to pleat,.
The expression oil-aqueous suspension concentrate is understood to mean an aqueous suspension in which the solid active substances are in the form of
00 crystals in suspension in water and the oily organic phase, here the vegetable oil plus an emulsifier, in the form of an oil-in-water emulsion.
The suspension concentrates, which can also be applied by spraying, are prepared so as to obtain a
15 stable fluid product which does not give cite to thickening or to the formation of a sediment after storage or to phase separation, and they usually contain from 10 to 75% of active substances, from 0.5 to 15% of surfactants, from 0.1 to 10% of thixotropic
20 agents, from 0 to 10% of appropriate additives, such as pigments, colorants, antifoams, corrosion inhibitors, sterilizers, penetrating agents, adhesives and, as carrier, water or an organic liquid in which the active substances are not or not very soluble.
25    Some organic solid substances or Inorganic
salts may be dissolved or dispersed in the carrier to prevent sedimentation or AS antigel for the water.
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According to an advantageous variant of the invention and by way of example, here is a composition of the oil-aqueous suspension concentrate type:
Example SC1:
- ACtive substance    375
- Ethoxylated polyararylphenol
phosphate potassium salt    60
- Dioctyl sulphosuccinate sodium salt    10
- Ethcxylated oleic acid    8.5
- Polyunsaturated vegetable oil    170
Mondpropylene glycol    50
- Polysaccharide    1.4
- 1,2-Benzisothiasolin-3-one    0-7
Isotridocanol    10
- Citric acid monohydrate    1
- water    (qa 1 litre)
The composition according to the invention is prepared according to methods known per ale. An example of a method, as a guide, is described below:
- Add simultaneously, to water with stirring, monopropylene glycol, isotridecanol, ethoxylated
10 polyararylphenol phosphate potassium salt, dioctyl sulphosuccinate sodium salt, citric arid monohydrate.
- Continue stirring to as to disperse and dissolve the constituents.
- Then add, with stirring, the active substance.
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-    The suspension is pre-ground with the aid of a colloid mill and then ground to the final particle size with the aid of a ball mill.
-    With stirring, add the solution containing 2% of 5 polysaccharide and 1% of 1,2-benzisothiazolin-3-one to the ground suspension.
- With stirring, add the oily phase, consisting of the homogeneous mixture of vegetable oil and
ethoxylated oleic acid, so as to form the oil-in-water 10 emulsion.
The fungicidal composition which is the subject of the invention is applied by means of various methods of treatment such as spraying onto the aerial parts of the crops to be treated with a liquid
15 comprising the said composition, sprinkling, injection into the trees and coating.
Spraying a liquid on the aerial parLs of the crops to be treated is the preferred method of
treatment.
20    The invention finally relates to a method of
treatment intended for combating or preventing fungal diseases of crops, characterized in that an effective and non-phytotoxic dose of a composition according to the invention is applied to the aerial parts of the
25 plants.
The expression "effective and non-phytotoxic quantity' is understood to mean a quantity of
composition according to the invention sufficient to
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14
allow control or destruction of the fungi present or likely to appear on the crops, and resulting in no symptom of phytotoxiCity for the said crops. Such a quantity is likely to vary within broad limits
5 depending on the fungus to be combated, the type of crop, the climatic conditions and the compounds inCluded In the fungicidal composition according to the invention. This quantity may be determined by
systematic field trials, within the capability of 10 persons skilled in the art.
These combinations are advantageously used to that the applied dose is between 250 and 1 000 g/na, preferably between 500 and 750 g/ha for compound A and between 0.25 to 0.45 times the data of compound A, that
15 is from 225 to 337.5 e/ha for a ratio of 0.45 P
(0 - guarantee in relation to active substance) for compound B (when A is taken at 1st preference doses of 500 to 750 g/ha).
These doses depend on the plant treated, the
20 degree of infestation, the climatic conditions and the like. For example, in the case of turf, the dose of A may be up to 5 kg/ha.
PhYtoPnthogenic fungi of crops which may be combated by this process are in particular those)
25    - of the adelomy.tes group,
- of the genus Alterneria, for example
A. solani, A. citri, A. mall, A. kikuchiana,
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15
A. alternate, A. pOtri, A. brassicae, A. brassicicola, A. dauci, and the like
-    of the genus Botrytis, for example S. cicerea or B. sgeamosa,
5    - of the genus Sclerotinia, for example
S. sclerctiniem, S. miner or 5. homeocarpa,
- of the genus Penicillium, for example P. digitate, P. exp..,
- of the genus Monilia, for example M. Mali, 10 M. laxa, M. fructigema,
- of the genus Rhiscpes, for example
R. stclonifer,
-    of the genus Sclerotiem, for example
S. cep,v0tam,
15    - of the genus F1.Sari um, for example
F. rOSOUM,
 

 
M. nivale,
- of the Basidiomycetes group:
-    of the family Rhizoctonia opp.
25    A classification made, no longer based on the
fungi targeted. bit On the target crops may be
illustrated as below:
- barley: net blotch illeleinthosporieml,
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10
- rapeseed: alternaria leaf spot (Alter-Marla spp.), grey mould (sotrytis c.inerea), sclexotinia diseases (Sclerotinia scIeroticrom)
- vine: grey mould iliotrytis ciner.),
- Solanaceae: alternarie leaf spot (Alternaria solani) and grey mould (Botrytis cinerea) in
particular,
- vegetable crops: alternaria leaf spot
(1Iternaria spp.I, SCIeratinia diseases (Sclerotlnia
10 app.?, grey mould (Sourytis cinema), foot or root rot {Rhizectenia spp.),
- rice: foot or root rot (RhIroOtonla spp.), deceleration of the grains (Alternaria sop., Helminthesporium spy., and the like),
15    - arboriculture: alternaria leaf spot (Alternaria
app.), grey mould (Botrytis c,nere,0 and brown rot (Monilia fructigena),
- citrus: scab (Els2nee faweetti), green and blue moulds (PeniciLlium digital. and EI.exyans.),
20    - turf: rust, oidium, net blotch, telluric
diseases liVicrodeohirm niva2e, SYthlo(II spp. Rhizoctonia
Sele.rotinfa hameocarpa and the like).
Among the crops suitable far the method of
treatment according to the invention, there may be
25 mentioned cereals, in particular barley, protein-rich plants and oil-producing plants, such as peas, rapeseed, sunflower, maize, vine, potato, tomato, vegetable crops (lettuce, Cueurbitaceae and the like),
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• rice,. arbbriculture (apple tree, -pear tree, cherry tree and the like), citrus and turf.
In the method of treatment according to the invention, components A and A of the composition
5 according to the invention' are generallY applied, -simultaneously, by means of a composition according to the invention prepared from a ready-to-use concentrate or from a tank mix.
Another aspect of the invention relates-to a
10 prod., for applying demponrds A and 5 of tharfungicidal oduposition according to the invention, wherein the compounds A anotTi are applied simultaneously, sequentially or alternately.
The following examples are given without limitation of the ,advantageous properties o£ the
15 combinations according to the invention.
The compositions, numbered with roman numerals, are or the type described above. Example I
In this study, the effect of the nature of
20 the vegetable or mineral oil is compared in terms of se/activity and efficacy, with or without rain, by means of two formulations, numbered in roman numeral's, suCh as,
I: 245 g/1 of iprodione + 255 5/1 of mineral oil
25 512 (that in to say Sommer insecticide Bane) (SC). Ii( 255 g/I of iProdione + 255 9/1 of vegetable
all Rapeseed CT !SC).
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18
The experimental protocol relating as the study of the selectivity on tobacco plants is the following:
The two formulations are sprayed at doses of 5 750 and 1500 g of iprodione/ha in a plant-protection mixture volume of 150 1/ha on 2-week old young tobacco plants (4-6 leaf stage) (3 repetitions/test factor). After drying of the products sprayed onto leaves, the plants are placed in a controlled environment cabinet
10 at 25°C during the day and 20°C during the night (photoperiod 16 h/8 h). A phytotoxicity score at S of
surface attacked) is determined after 7 days 17 JATII followed by a second treatment and that the placing of the plants under the same conditions as above. A final
15 phytotoxicity score is determined after 7 days (7 JAT2).
Selectivity        7 JAT1    7 JAT2
I-    750 g/ha    1 P SIB    0.7    1-0
- 1500 g/na.    mineral    2.3    4.3
II -750 g/ha    1 P Rapeseed CT    1.0    1.0
- 1500 g/ha    vegetable    1.3    1.3

The formulation based on rapeseed vegetable oil is found to be more selective than the formulation based on mineral oil Summer Insecticide Base for the
20 same dose of oil.
The efficacy is determined against Betrytis cinerea of gherkin in the presence or in the absence of
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19
washing out, that is to say with or without raze- For this study, the experimental protocol is the following:
The formulations under study are used at doses    50 - 100 - 200 and 400 ppm of iprodione (test
5 without washing out) or 100 - 200 - 400 and 800 ppm of iprodione (test with washing out). They are sprayed on gherkins, Petit Vert de Paris variety, at the cotyledon-first visible leaf stage (2 x 3 repents/test facto/9. Four hours after the treatment, the groups of
10 3 plants/dose of fungicide under study are subjected to washing out with 25 as of rain for 30 min. A day after the treatment, the gherkin plants are contaminated by depositing drops of water containing an inoculum at 150 000 spores of iiorrytis cinerealml of inoculum. They
15 are then placed in a controlled environment cabinet at 12-15°C, 100% RH. A score (in % of surface attacked) is determined 7 days after the inoculation. The data then serve to establish a sigmoid type dose-response curve which cakes it possible to determine the rC90
20 (concentration causing 909 inhibition of the disease) as well as the confidence interval in which each IC50 exists,
 
Efficacy and resistance    IC90 min. IC max. IC
to rain

I    1 P SIB           
without rain    mineral    137    96    194
with rain        459    303    550
II    1 9 Rapeseed           
without rain    CT
vegetable    220    188    273
with rain        473    387    572
 
The formulation based on rapeseed vegetable
oil has efficacy without rain which is slightly less than that based on mineral oil SIB, but with a
5 nonsignificant difference in efficacy.
On the other hand, this formulation based on rapeseed oil exhibits efficacy in the presence of washing out with rain which 13 equivalent to the
formulation containing the same dose of mineral oil
10 SIB.
Example 2
In this study, the effect of the nature of the vegetable or mineral oil is compared in terms of efficacy in the presence of rain (resistance to rain),
15 by means of two formulations such EIS:
III:    255 g/1 of iprodione + 350 gfl of mineral
oil SIP (SO).
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2
IV,    500 g/1 of iprodione 4 125 g/.1 of linseed
oil TS (SC).
The efficacy is determined against Sotrytis cineria of gherkin in the presence of rain. For this 5 study, the experimental protocol is the same as above.
Resistance to rain    IC90 Tri.n. IS max. IC
III    1.35 P SIB    BO    593    109
with rain    mineral    5    3
Is    0.25 P    96    915    101
with rain    linseed TS    2    2
The linseed vegetable oil-based formulation appears slightly less effective than that based on mineral oil but this difference is not significant.
10 This linseed vegetable oil-based formulation therefore
exhibits efficacy in the presence Of rain (resistance to washing out) equivalent to the formulation
containing 1.35 a of mineral old. It should be noted that the nose of vegetable oil used is about 5 times
15 less than that used in III (for an equal dose of active Substance).
Example 3
Is this study, the effect of the nature of
the vegetable or mineral oil is compared in terms of
20 efficacy in the presence of rain (resistance to rain), by means of tour formulations such as,
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2
V;    500 gIl of iprodione + 175    of linseed
oil TS (SC).
VI:    500 g/1 of iprodione + 175 9/1 of refined
sunflcwer oil (SC).
5    VII:    SOT g/1 of iprodione + 175 g/1 of mineral
oil SIB (SC).
III: 255 g/l Of iprodione + 350 g/1 of mineral Oil (EC).
The efficacy is determined against Botrytis
10 cineria of gherkin in the presence of washing out with rain. For this study, the experimental protocol is the same as above.
Resistance to CO.    1090    min.    IC    max.    IC
    0.35 P linseed    327    262        40
                7   
VI    0.35 P refined    287    252        33
    sunflower            0   
VII    0.35    P 8113    497    445        55
    mineral            5   
III    1.35    P SIB    290    225        31
    mineral            2   

The two vegetable oil-based formulations
15 containing only 0.35 P of oil exhibit resistance to rain equivalent to that of III (formulation containing 3.8 times more mineral oil).
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2
The mineral oil-Cased formulation at the dose of 0.35 P is found to be significantly less resistant to rain than those containing the seine dose of polyunsaturated vegetable oil such as refined sunflower 5 or linseed oil.
Example 4
In this study, the effect of the nature of the vegetable or mineral oil is compared in terms of efficacy, resistance to rain and selectivity, by means
10 of three formulations such as:
VIII:    500 9/1 of lProdione + 175 9/1 of
lsomerized sunflower oil (SC).
IX:    500 9/1 of iprodione without addition of oil (SC).
255 g/1 of iprodione r 350 g/1 of mineral oil SIB (SC)-
The efficacy is determined against BOtrytis cineria of gherkin in the presence or absence of ...Shim out with lain. For this study, the experimenraT
20    protocol is the same as above.           
Efficacy and resistance to rain    IC90    min.    IC    max.    IC
VIII - without rain
- with rain    0.35 P
isomerired
sunflower    1 65 5 09    10
6
39
7    25
7
65
3
IX    - without rain    without
oil    1
69    95    2

-25-
 
2
- with rain    9    DO    12
    54    2
III - without rain 1.35 P 3113    1    10    24
    62    8    2
- with rain    4    42    55
    87    8    5
The formulation containing an isomerized sun-flower vegetable oil exhibit, efficacy without rain and resistance to rain equivalent to III. The use of a veg-etable oil of this type, that is to say polyunsaturat¬5 ed, makes it possible to reduce the dose of oil by
about 3.8 fold, in the treatment plant-protection mixture.
The selectivity is determined on tobacco plants according to the protocol previously described.
10
Selectivity        7    JAT1    7    JA72
VIII - 750 g/ha    0.25 P        0        1.7
- 1500 g/ha    isomerized
sunflower        0        2.0
Selectivity        7    5,171    7    .1272
Ix    -750 g/ha    without oil        0.7        1.0
IX    -150D g/ha            0.3        0.3
III -750 g/ha    1.25 P SIB        1.3        1.3
III    -1500 g/ha            13.0        15.0

Prom the firat application, the mineral oil-based formulation exhibits unacceptable phytotoxicity. On the other hand, the isomerizad sunflower vegetable
-27-
 
25
oil-based formulation is found to be particularly selective on tobacco plants.
Example 5
In this study, the effect of the nature of 5 the vegetable or mineral oil, and the effect of the dose of vegetable oil are compared in terms of
efficacy, resistance to washing out and selectivity by means of five foraulations such as,
x;    375 g of iprodione/1 + 131 g/1 of refined
10 sunflower oil (SC).
XI:    375 g of iprodione/1 + 169 g/1 of refined sunflower oil (SC).
XII:    375 g of iprodione/1 + 206 g/1 of refined sunflower oil (811•
IX:    500 g of iprodione/1 without addition of
oil (SC).
III:    255 g of iprodione/1 + 350 g/1 of mineral
oil SIB (SC).
She efficacy is determined against Botrytis
20 cinerea of gherkin in the presence or the absence of rein. For this ...AY, the experimental protocol is the same as above.
Efficacy and resistance to    IC90 min. IC max. IC
washing out  X    - without rain    0.35 P    150    10    2
    7    12
 

 
-28-
 
2

- with rain    refined    512    49    5
    sunflower        2    33
XI    - without rain    0.45 P    135    11    1
            1    65
- with rain    refined    479    43   
    sunflower        9    22
XII    - without rain    0.55 P    142    12    1
                69
- with fain    refined    426    37    4
    sunflower        9    30
IK    - without rain    without    134        2
    oil            62
- with rain        838    62    1
            1    129
III    - without rain    1.35    P    205    13    3
    SIB    7        07
- with rain        532    42   
        5        66

The formulations containing a refined
sunflower vegetable oil at doses of 0.35 P, 0.45 P and
0.55 P exhibit efficacy without rain and resistance to
rain equivalent to those of III. The use of a highly 5 polyunsaturated vegetable oil makes it possible to reduce the dose of oil to about 3.8 fold in the treatment plant-protection mixture.
-20-
 
27
The selectivity is deterraned on tobacco plants for these five formulations as well as the following formulation,
XIII:    SC containing 375 g of iprodione/1
5 + 199 g/1 of mineral oil SIB.
This formulation makes it possible to
determine the effect of the dose of mineral 011 on the selectivity of the product.
The protocol remains the same as previously
10 described:
    Selectivity    7    JAT1    7 JAT2
X    - 750 g/ha    0.35 P    0.3    1.0
    - 1500 g/ha    refined sunflower    0.3    0
XI    - 750 g/ha    0_45 P    0.7    1.0
    - 1500 g/ha    refined sunflower    1.3    0.7
XII    - 750 g/he    0.55    P    0.7    0.3
    - 1500 g/ha    refined sunflower    0.7    1.1
IX    - 750 g/ha    without oil    0.3    0
    -1500 g/ha        0    0
XIII - 750 g/ha    0.53    P. SIB    1.0    0.3
    -1500 g/ha        2.3    2.3
TIT -750 g/ha    1.35 P SIB    2.7    2.3
    -1500 g/na        3.3    6-0

The refined sunflower vegetable oil-based formulations exhibit better selectivity than that of III- The incorporation of mineral oil leads to
-30-
 
28
phytctoxicity which is sometimes unacceptable which is found to be dose-dependent.
Example 6
In this study, the effect of the nature of 5 the vegetable or mineral oil is compared in terms of efficacy, resistance to washing out and selectivity by means of three formulations such as)
XIV:    375 g/1 of iprodione + 170 g/1 of refined
sunflower oil (SC).
10    IX:    500 g/1 of iprodione without addition of
oil (SC).
III:    255 g/1 of iprodione + 350 g/1 of mineral
oil SIB (SC).
The efficacy is determined against Botrytis 15 cineres of gherkin in the presence or in the absence of washing out with rain. For this study, the experimental
protocol is the same as above.           
Efficacy and resistance to rain    IC90    min.    IC    max. IC
090 - without rain    0.45    a    122    83    17
                8
- with rain    refined    446    39    51
    aunflower        2    3
IX    - without rain    without    114    97    13
    oil            4
- with rain        671    51    88

-31-
 
29
III - without rain    1.35 SIB    111    12
III - with rain    mineral    509    41    63
The formulation containing the refined
sunflower vegetable oil exhibits efficacy without rain and resistance to rain equivalent to that of III- The use of a vegetable oil of this type, that is co say
5 polyunsaturated, makes it possible II reduce the dose
of oil by 3, in the treatment plant-protection mixture.
The selectivity is determined on tobacco
plants according to the protocol previously described:
    Se:ecrivity    7    JAT1    7    JA22
XIV    - 750 g/ha    0.45    F    1.7    1.7
    - 1500 g/ha    refined sunflower    4.7    3.7
ix    - 750 g/ha    without oil    1.3    0.3
    - 1500 g/ha        1-3    0.3
    III
-750 q/ha    1.35 P SIB    3.3    1.3
    -1500 gilla    mineral    16.7    16.7

From the first application. the mineral oil-based formulation exhibits unacceptable phytotoxicity. on the other hand, the vegetable oil-based formulation containing 0.45 F of refined sunflower is found to be particularly more selective than III.
-32-
 
General conclusionf
These polyunsaturated vegetable oil-based formulations therefore favourably meet the object set. Indeed, the formulations based on vegetable oils
5 exhibit better selectivity than the formulation-based on mineral oil (Summer Insecticide Base), the
biological activity, with or without washing out, is at
the same level as that of the :vast effective, ineral oil-based 5hOmer Insecticide Base fOrmulations.
10    The advantage of this type of suspension
concentrates ale; consists in the ace.of a dice of oil which is three times less, in the treatment Plant-protection mixture, than thahcustomarily used in the case of the mineral oil SIB.
It is to he understood that a reference herein to a prior art docuient does not constitute an admission that the document form. part Of the common general knowledge in the art in Australia.
In the claims which follow and in the Prec.dng 20 descripciofi of the invention, except where the context
requires otherwise due to express language or necessary
implication, the word 'eempriSt" or variations suet, as
"comprises" or "comprising” is.used in an inclusive sense, i.e. tc specify the presence of the stated features but not
25 co preclude the presence or.addition of further features in various embodiments of the invention.
-33-
 
CLAIMS
1.    A fungicidal composition consisting essentially of
at least one fungicidal compound A, iprodione, and at least one oil B, this oil being of plant origin and possessing a high siccative power selected from the group consisting of linseed, sunflower, soya bean, maize, cottonseed, safflower and rapeseed oils, and possessing an iodine value greater than 90, wherein the compound B/compound A weight ratio is between 0.15 and 1.6.
 
2.    Fungicidal composition according to the preceding claim, characterized in that the fungicidal compound A is chosen from dicarboximide derivatives.
3.    Fungicidal composition according to
10 either of the preceding claims, characterized in that the fungicidal compound A is chosen from captan, captafol, chlozolinate, iprodione, procymidone and vinclozolin.
4.    Fungicidal composition according to any
15 of the preceding claims, characterized in that the vegetable oil B possesses an iodine value which is greater than 70, preferably greater than 90, more preferably still greater than 130, and most preferably greater than 150.
20    5.    Fungicidal composition according to any
of the preceding claims, characterized in that the vegetable oil B is chosen from linseed, sunflower, soya bean, maize, cottonseed, safflower and rapeseed oils.
6.    Fungicidal composition according to any
25 of the preceding claims, characterized in that the compound B/compound A weight ratio is between 0.15 and 1.6, preferably between 0.2 and 1.35, more preferably
 
7.    A fungicidal composition consisting essentially of:
(i)    at least one fungicidal compound A, said fungicidal compound A
being iprodione; and
(ill    at least one oil B, said oil B being of plant origin, possessing a
high siccative power, and possessing an iodine value greater than 150, wherein the compound B/compound A weight ratio is between 0.15 and 1.6.
8.    A method of treatment for combating fungal
diseases of crops comprising applying an effective and non-phytotoxic dose of the composition of claim 7 to the aerial parts of the plants.
9.    A fungicdal composition consisting essentially of:
(i)    at least one fungicdal compound A, said fungicidal compound A
being iprodione; and
(ii)    at least one oil B, said oil B being sunflower oil and possessing    a
high siccative power, wherein the compound B/compound A weight ratio is between 0.15 and 1.6.
10. A method of treatment for combating fungal diseases of crops comprising applying an effective and non-phytotoxic dose of the composition of claim 9 to the aerial parts of the plants.
11.    A fungicidal composition consisting essentially of:
(i)    at least one fungicidal compound A, said fungicdal compound A
being iprodione; and
(ii)    at least one oil B selected from the group consisting of linseed,
sunflower, soya bean, maize, cottonseed, safflower and rapeseed oils, said oil possessing a high siccative power, wherein the compound B/compound A weight ratio is 0.45.
12. A method of treatment for combating fungal diseases of crops comprising applying an effective and non-phytotoxic dose of the composition of claim 11 to the aerial parts of the plants.
 
indexation.Ist QCOK tags.Ist

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