AP202A

AP202A - Procedure for protecting plant propagation products and the plants obtained from them.

Info

Publication number: AP202A
Application number: APAP/P/1991/000276A
Authority: AP
Inventors: Alfred Greiner; Jean Hutt; Jacques Mugnier; Regis Pepin
Original assignee: Rhone Poulenc Agrochimie
Priority date: 1990-06-12
Filing date: 1991-06-12
Publication date: 1992-06-30
Also published as: PT97932A; NO912210L; US5246953A; FR2662911A1; OA09361A; CN1057942A; FI912808A0; FI912808A7; EP0467791A1; ZA914495B; IL98416A0; FR2662911B1; FI912808L; EP0467791B1; DE69105847T2; DE69105847D1; JPH04243803A; DK0467791T3; NO912210D0; AP9100276A0

Abstract

The invention relates to the protection

Description

PROCESS FOR PROTECTING PLANT PROPAGATION

PRODUCTS AND THE PLANTS OBTAINED FROM THEM

The present invention provides a method for the protection against fungal diseases-of plant propagation products and plants obtained from them, to the treated products and plants, and to compositions useful in the method.

The present invention provides a process for protecting, by curative or prophylactic means, plant propagation products and the plants obtained from them against fungal diseases by applying to the propagation product 2-(4-chlorobenzylidene)-5,5-dimethyl-l-(1H-1,2,4triazol-l-ylmethyl)-1-cyclopentanol.

It has been found, in a completely unexpected manner, that a fungicidal composition, which comprises 2(4-chlorobenzylidene)-5,5-dimethyl-l-(1H-1,2,4-triazol-lylmethyl)-1-cyclopentanol in addition to its fungicidal activity applicable to the propagation products themselves, also allowed protection of the crop after germination and possibly up to harvest. Use of the composition and method of the invention avoids, in numerous cases, the need for one or more foliar treatments.

2-(4-Chlorobenzylidene)-5,5-dimethyl-l-(1H-1,2,4triazol-l-ylmethyl)-1-cyclopentanol is described in the European Patent Publication No. 0378953 published on 25th

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July 1990.

That Application also describes, in Examples 14, 15 and 16, a wheat seed of the Talent variety coated with the said triazole.

By the term propagation product is meant all the generative parts of the plant which may be used for its propagation. These include for example, seeds, roots, fruits, tubers, bulbs, rhizomes and plant sections.

Sprouted plants and young plants which have to be transplanted after germination or after coming out of the soil may also be mentioned. These young plants may be protected before transplanting, for example, J&X.A total or partial treatment by steeping. It is to be understood that the plant propagation products, for example seeds, can be treated in situ in the soil.

Seeds are preferred for crops other than potatoes. The following are preferred among the propagation products suitable for the method according to the invention:

- dicotyledon seeds: pea, cucumber, melon, soybean, cotton, sunflower, rape, bean, flax and beet,

- monocotyledon seeds: cereals (eg wheat with the exception of the Talent variety before the onset of tillering, preferably soft winter wheat, soft spring wheat, hard wheat, barley, rye, oat), lucerne, maize and rice.

- or potato tubers.

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Preferably, seeds are coated with 0.1 to 500 g of active material per quintal of seed, more preferably 1 to 400 g per quintal.

Preferably, in the case of tubers, they comprise, as coating or absorbate a quantity-of active material which corresponds to soaking the tubers in a composition containing 0.1 g/1 to 100 g/1 of active material.

The compositions according to the invention generally contain between 0.5 and 95% of active material.

In this specification unless otherwise seated all percentages are by weight.

The term carrier, in the present text, designates an organic or inorganic material, natural or synthetic, with which the active material is combined in order to facilitate its application to the plant propagation product, to the plant, to seeds or to the soil. This carrier is therefore generally inert and must be agriculturally acceptable, in particular on the treated plant. The carrier may be solid (eg clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers) or liquid (eg water, alcohols, ketones, petroleum fractions, aromatic or paraffinic hydrocarbons, chlorinated hydrocarbons, liquified gases).

The surface-active agent may be an emulsifying, dispersing or wetting agent of the ionic or nonionic type. The following may be mentioned by way of example:

AP 0 0 0 2 0 2 polyacrylic acid salts, iignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts, polycondensates of ethylene oxide and fatty alcohols or fatty acids or fatty amines, substituted phenols (alkylphenols or arylphenols in particular), ester salts of sulphosuccinic acids, taurine derivatives (alkyltaurates in particular), phosphoric esters of alcohols or of polyoxyethylated phenols. The presence of at least one surface-active agent is often required given that the active material and/or the inert carrier are insoluble in water and that the vector agent of the application is water. . ,- ......

These compositions may also contain other ingredients such as, for example, protective colloids, adhesives, thickeners, thixotropic agents, penetrating agents, stabilisers, sequestrants, pigments, colorants and polymers.

More generally, the compositions according to the invention may be combined with all those solid or liquid additives found in the usual formulation procedures for applying the seed treatment in particular.

In this regard, it will be noted that in the jargon used by specialists, the term seed treatment in fact refers tc the treatment of grains.

The methods of application are well known to the specialist and may be used within the scope of the present

BAD ORIGINAL invention.

The formation of a thin film or coating may for example be mentioned.

Among the compositions, solid or liquid 5 compositions may generally be mentioned.

By way of solid composition forms, the following may be mentioned: powders for dusting or dispersing (with a content of active material which may be as high as 100%) and granules, in particular those obtained by extrusion, by compaction, by impregnation of a granulated carrier and by granulation from a powder (the content of active material in these granules being between 1 and 80% in the latter cases).

The compositions may furthermore be used in the form of a powder for dusting; a composition comprising 50 g of active material, 10 g of finely divided silica, 10 g of organic pigment and 970 g of talc may thus be used; these constituents are mixed and ground and the mixture is applied by dusting.

By way of liquid composition forms or forms intended to constitute liquid compositions on application, the following may be mentioned: solutions, in particular water-soluble concentrates, emulsifiable concentrates, emulsions, concentrated suspensions, aerosols, wettable powders (or spray powder), pastes and dispersible granules.

The emulsifiable or soluble concentrates generally

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BAD ORIGINAL comprise 10 to 80% of active material; the emulsions or solutions ready for application contain, for their part, 0.01 to 20% of active material.

For example, in addition to the solvent, the 5 emulsifiable concentrates may contain, when necessary, 2 to

20% of appropriate additives such as stabilisers, surfaceactive agents, penetrating agents, corrosion inhibitors, colorants or adhesives previously mentioned.

From these concentrates, emulsions of any desired concentration, which are particularly suitable for application to seeds, may be obtained by dilution with water.

The concentrated suspensions, which can also be applied by spraying, are prepared so as to obtain a stable fluid product which does not form deposits, and they normally contain from 10 to 75% of active material, 0.5 to 15% of surface-active agents, 0.1 to 10% of thixotropic agents, 0 to 10% of appropriate additives, such as pigments, colorants, antifoams, corrosion inhibitors, stabilisers, penetrating agents and adhesives and, by way of carrier, water or an organic liquid in which the active material is barely soluble or insoluble: some organic solid materials or inorganic salts may be dissolved in the carrier to help prevent sedimentation or as anti-freeze fcr water.

The wettable powders (or spray powder) are normally λ BAD ORIGINAL

Ί prepared so that they contain 20 to 95% of active material, and they normally contain, in addition to the solid carrier, from 0 to 5% of a wetting agent, 3 to 10% of a dispersing agent and, when necessary, from 0 to 10% of one or more stabilisers and/or other additives, such as pigments, colorants, penetrating agents, adhesives, or anticoagulating agents.

To obtain these spray powders or wettable powders, the active material is thoroughly mixed in appropriate mixers with the additional substances and they are ground using mills or other appropriate grinders. Spray powders are thereby obtained whose wettability and ability to form suspensions are advantageous; they can be suspended in water at any desired concentration and these suspensions may be used very advantageously in particular for application to seeds.

In place of the wettable powders, pastes may be prepared. The conditions and methods for the preparation and the use of these pastes are similar to those for ’0 wettable powders or spray powders.

The dispersible granules are normally prepared by agglomeration, in appropriate granulation systems, of the compositions of the wettable powder type.

As already indicated, the dispersions and aqueous 25 emulsions, for example the compositions obtained by diluting a wettable powder or an emulsifiable concentrate

&P 0 0 0 2 0 2

BAD ORIGINAL according to the invention with water, are included within the general scope of the present invention. The emulsions may be of the water-in-oil or oil-in-water type and they may have a thick consistency like that of a rcayonnaise'·.

Among these compositions, -the specialist will advantageously choose that or those which is/are suitable in relation to the conditions of use.

Preferably the compositions of the invention comprise a marker, preferably visible, eg a pigment or colorant, by which treated plant propagation products, eg seeds, can be distinguished.

According toa preferred future ofsthe?invention, the composition according to the invention will furthermore contain a pigment known per se to reduce the phytotoxicity of triazoles. This feature may be useful in the case of high fungicidal doses, especially for dicotyledons.

In the case of rice, it has been found that the composition also possessed a disinfectant effect.

The method according to the invention may be used 20 in a prophylactic as well as curative capacity for the protection of plant propagation products against fungal disease, particularly of the basidiomycete, ascomycete, adelomycete or imperfect fungi types, in particular rusts, bunt, oidium, eyespot, fusarioses, Fusarium roseum,

Fusarium nivale, net blotch, leaf blotch, septoria spot, rhizoctonioses of vegetables and plants in general and, in

BAD ORIGINAL particular, of cereals such as wheat, barley, rye, oat and their hybrids and also rice and maize.

The method according to the invention allows in particular the combating of fungi particularly of the following types: basidiomycetes, ascomycetes, adeloraycetes or imperfect fungi such as Botrytis cinerea. Erysiphe graminis. Puccinia graminis. Puccinia recondita.

Piricularia oryzae. Cercospora beticola. Puccinia striiformis, Erysiphe cichoracearum. Rhinchosporium

1° secalis. Fusarium solani. Fusarium oxysporum (var-melonis. for example), Pvrenophora avenae. Septoria tritici.

Septoria avenae, Whetzjgiinia sclerotjorufl, MysogphftSEeXIfr fiiiensis. Mvcosphaerella musicola. Alternaria solani. Aspergillus niqer. Cercospora arachidicola, Cladosporium herbarum. Tilletia caries. Tilletia contreversa. Fusarium roseum, Fusarium nivale. Helminthosporium oryzae. Helminthosporium teres. Helminthosporium gramineum. Helminthosporium sativum. Penicillium expansum. Pestalozzia sp, Phoma betae, Phoma foveata. Phoma 1 ingam. Ustilago mavdis. Ustilago nuda, Ustilago hordei. Ustilago avenae. Verticillium dahliae, Aschochvta pisi. Aschochyta anthracnose. Guignardia bidwellii. Corticium rolfsii. Phomopsis viticola. Sclerotinia sclerotiorum. Sclerotinia minor. Coryneun cardinale. Rhizoctonia solani.

Acrostalagmus koningi. Alternaria. Colletotrichum. Diplodia natalensis, Gaeumannomyces graminis. Gibberella fuj ikuroi..

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Hormodendron cladosporioides. Myrothecium verrucaria. Paecylomyces varioti, Pel1icularia sasakii, Phellinun megaloporus, Sclerotium rolfsii. Stachybotris atra . Trichoderma pseudokcningi, Trichothecium roseum and

Vascular fusarioses.

The method of the invention makes it possible to effectively combat cereal diseases (oidium, rust, oyespot, leaf blotch, net blotch, septoria spot and fusarioses).

They are also of great interest because of their ac tivity on grey mould (Botrytis) and leaf spot, and, as a result, they can be applied to products of crop propagation as varied as vines, market garden crops, arboricultural crops and tropical crops such as groundnuts, banana plants, coffee plants and pecan nuts.

The fungicidal compositions of the present invention are also useful for the disinfection of cereal seeds against Ustilago nuda. Septoria nodorum. Tilletia caries and Tilletia controversa. Helminthosporium aranineum and numerous Fusarium species.

The present invention also provides a plant propagation product or plant obtained therefrom coated with and/or containing 2-(4-chlorobenzyliden.e)-5,5-dimethyl-l(1H-1,2,4-triazol-l-ylmethyl)-l-cyciopentanol with the proviso that the said propagation product is not a wheat grain of the Talent variety.

The active material is generally present at the surface of the product during application although a more or less substantial portion may penetrate the product depending on the mode of application. When the said propagation product is replanted, it absorbs the active material.

In fact, commercially, it could be said that most of the active material is at the surface most of the time.

Preferably, the propagation product is chosen from among seeds chosen advantageously from among the seeds:

- dicotyledons: pea, cucumber, soybean, melon, cotton, sunflower, rape, bean, flax and beet

- monocotyledons: cereals (eg wheat with the exception of the Talent variety, preferably soft winter wheat, soft spring wheat, hard wheat, barley, rye, oat), lucerne, maize and rice.

Preferably the seeds are coated with an amount of 0.1 to 500 g of active material per quintal of seed and more preferably 1 to 400 g/quintal.

According to a further feature of the invention the 20 propagation product is preferably a potato tuber coated with and/or containing a quantity of active material which corresponds to soaking the said product in a solution containing 0.1 g/1 to 100 g/1 of active material.

The present invention also provides a fungicidal composition for use in the method of the present invention, comprising 2-(4-chlorobenzylidene)-5,5-dimethy1-1-(ihAP 0 0 0 2 0 2 bad original

1,2,4-triazol-l-ylmethyl) -1-cyclopentanc1, an agriculturally acceptable inert carrier and/or an agriculturally acceptable surface-active agent.

Preferably, the fungicidal composition is characterised in that the propagation products are seeds chosen from among the seeds of:

- dicotyledons: pea, cucumber, soybean, melon, cotton, sunflower, rape, bean, flax and beet,

- monocotyledons: soft winter wheat with the exception of wheat of the Talent variety, hard wheat, soft spring wheat, barley, rye, maize and rice.

The invention also provides a fungicidal composition for use in the method*of the present invention, characterised in that it applies to seeds of soft winter wheat and in that it contains 2-(4-chlorobenzylidene)-5,5dimethyl-1-(1H-1,2,4-triazol-l-ylmethyl)-1-cyclopentanol, an agriculturally acceptable inert carrier and/or an agriculturally suitable surface-active agent.

The fungicidal composition is characterised in particular in that it applies to seeds of the Talent variety.

The following Examples illustrate the invention. Lose units g/q are grams per quintal.

EXAMPLES

Example Ί

2- (4-Chlorobenzyl idene)-5,5-dimethyl -1- ( 1i , 2,4BAD ORIGINAL triazol-1-ylraethyl)-l-cyclopentanol (A) has been formulated in the form of a concentrated suspension at 200 g/1 according to techniques well known to the specialist.

Wheat seeds of the Nebraska variety particularly 5 sensitive to yellow rust (Puccinia- striifonnis) are treated with the above formulation after appropriate dilution so as to obtain the quantities of active material per quintal r

indicated in the table below. These seeds are sown. The results are read 192 days after sowing.

Treatment	Dose g/q %	foliar surface attacked
Control	-	42.5
A	30	18.8
	60	11.0
	90	9.3
	120	3.0
Example 2: Phvtotoxicity trial

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Barley seeds are treated as before and one month after sowing, the percentage of sprouted seeds is determined.

The results are shown below.

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Treatment

Dose g/q % cf sprouted seeds

Control

A

120

180

78.5

76.1

76.3

77.5

No sign of phytotoxicity was observed.

Example 3

Barley seedsnaturally contaminated by

Ustilago nuda are treated with the above formulation so as to obtain the quantities of active material per quintal indicated in the table below. These seeds are sown.

The results are read 8 months after sowing.

Treatment Dose g/q Ears attacked/m^{2 * 3}

Control - 30.3

A 5 0

0

0 0

Example 4

Barley seeds naturally contaminated by Septoria nodorum are treated as in Example 2.

The results are read 1 month after sowing.

Treatment	Dose g/q	% efficacy
Control		0
	5	100
	10	100
	30	100 ,

Example 5

Barley seeds are treated as in Example 4.

The results are read 152 days after sowing, after and attack by Erysiphe graminis.

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Treatment	Dose g/q	% foliar surface attacked
Control		35.0
A	30	18.8
	60	11.3
	90	9.0
	120	9.3

Example 6

Maize seeds naturally contaminated by Gibberella fu~i ikuroi are treated with the slurry of Example

The results are read 22 days after sowing.

Treatment Dose g/q % of healthy plants, 22 days after sowing

Control	—	13.5
A	5	24.1
	25	26.2
	50	59.0
	100	70.2

__

Example 7

Rice seeds naturally contaminated by Gibberella fui ikuroi (Fusarium) are treated with the slurry of Example 1.

The results are read one month after sowing.

Treatment

Dose g/q % diseased plants

AP 0 0 0 2 0 2

Control - 93.0

A 5 45.6

5 3.0

100 (;

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No phytotoxic effect was observed.

Example 8

Pea seeds naturally contaminated by Fusarium solani are treated with the slurry-of Example 1.

The results are read one month after sowing.

Treatment	Dose g/q	% stalks
	—
Control	-	57.3
A	5	27.1
	25	23.2
	50	22.1
	100	10.0

attacked

-5 Example 9

Cucumber seeds are treated with the slurry o

Example 1.

The results are read two months after sowing after and attack by Erysiphe cichoriacearun.

BAD ORIGINAL jr*** · 19

Treatment Dose g/q % foliar surface attacked

Control	-	36.2
A	25	23.0
	50	19.7
	100	18.3
	200	6.0

Example 10

Melon seeds are treated with the slurry of

Example 1.

The results are read 14 days after a contamination by Fusarium oxysporum var-melonis atment Dose g/q % efficacy

AP 0 0 0 2 0 2

Control	—	r
A	³	100
	6	100
	12	100
	25	100

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Example 11

Potato tubers naturally contaminated by Phoma foveata are soaked in a slurry as indicated in Example 1.

The results are read 64 days after sowing.

Treatment	Dose g a.m/1	% diseased tuber, 64 d. after showing
Control		84.8
A	1	4.4
	5	2.0
	10	2.0

It has moreover been found that the current fungicide is selective, with no sign of phytotoxicity on seeds of:

	cotton	at	lOOg/a
	sunflower	at	5 0g/q
dicots .	rape	at	50g/q
	bean	at	2 5g/c
	flax	at	10g/ q
	beet	at	50g/q
monocots .	maize	at	200g/q

BAD ORIGINAL under the same conditions as before.

Similarly, it has been found that the fungicide exhibited an excellent activity, against:

Phoma betae

Phoma foveata beet potato

Vascular fusarioses melon

Aschochyta (anthracnose) pea

Finally it has been found that the fungicidal composition was also useful in soil treatment for rice and banana plants.

SOIL TREATMENT

BANANA PLANTS - LEAF SPOT

Table: Effect of A against Mycosphaerella musicola, applied in soil treatment to banana plants in

Ivory Coast.

The banana plants are treated at all stage cf development.

AP 0 0 0 2 0 2

BAD ORIGINAL

Treatment	Dose/banana plant (g)	% leaves attacked
Control		26
A	0.5	6

2-(4-Chlorobenzylidene)-5,5-dimethyl-l-(lH1,2,4-triazol-l-ylmethyl)-1-cyclopentanol may be obtained as follows:

100 ml of a 10% aqueous solution of sodium hydroxide were added to a mixture of 10 g of 2,2dinethylcyclopentanone and 13.8 g of 4-chLorobenzaldehyde in 100 ml of ethanol at 0’C. After 30 minutes, a thick slurry was filtered off and the solid was washed and then dried. 12.5 g of 2,2-dimethyl-5-(4-chlorobenzylidene)-1cyclopentano.ne with a melting point of 120°C were obtained. Tnis compound, dissolved in 50 ml cf THF, was added to a solution formed in the following manner: 1.9 g of sodium hydride (80% dispersion in mineral oil) in 50 mi ol anhyaiOV? DMSO were heated to 80’C until complete dissolution of the solid. The solution was then diluted ,-. -s »-are bad ORIGINAL with 100 ml of THF, then cooled to -10*C. A solution of

11.5 g of trimethylsulphonium iodide in 80 ml of dimethyl sulphoxide was added to the mixture in the course of ten minutes and the mixture was stirred for 15 minutes at

-10’C. A solution of 11.8 g of 2,2-dimethyl-4-chloro-5-(4chlorobenzylidene)-1-cyclopentanone was then added in 100 ml of THF.

The mixture thus obtained was left at room temperature then poured into water and extracted with 10 ether, washed with water, dried and distilled. 7-(4Chlorobenzylidene)-4,4-dimethyl-l-oxaspiro[2.4 Jheptane, which was directly used in the subsequent stage, was ⁸⁵obtained.

A mixture of 5 g of product with 2.8 g of 15 1,2,4-triazole and 11 g of potassium carbonate was heated in 40 ml of N,N-dimethylformamide for 4 hours. The mixture was poured into water and extracted with ethyl acetate.

The organic phase was washed, dried and recrystallised to yield the stated product whose melting point is 142*C.

The structure of the compound is generally obtained (>95%), with the para-chlorophenyl group in the E position with respect to the carbon bearing the hydroxyl group.

2,2-Dimethylcyclopentancne may be obtained in :5 a manner which is known in the literature or is available commercially (see Fine Chemical Directory).

AP 0 0 0 2 0 2

BAD ORIGINAL

The fungicide (A), i.e., 2-(4chlorobenzylidene)-5,5-diraethyl-l-(1H-1,2,4-triazol-l ylmethyl)-1-cyclopentanol, is of the following formul

Claims

1. A method for the protection against fungal diseases of plant propagation products and the plants obtained from them which comprises applying to the

5 propagation product a compound which is 2-(4chlorobenzylidene)-5,5-dimethyl-l-(1H-1, 2,4-triazol-lylmethyl)-1-cyclopentanol.

2. A method according to claim 1, wherein the propagation product is a seed.

10

3. A method according to claim 2, wherein the seed is a seed of:

a monocotyledon which is hard wheat, soft spring wheat, soft winter wheat, barley, oat, rye, maize or rice; or

15 a dicotyledon which is pea, cucumber, melon, cotton, sunflower, rape, soybean, bean, flax or beet.

4. A method according to claim 1, wherein the propagation product is a potato tuber.

5. A method according to any one of claims 2 20 to 4, wherein there is applied to tne seed, 0.1 to 500 g of compound, in the form of a fungicidal composition, per quintal of seed.

6. A method according to claim 5 wherein 1 to 4CC g of compound per quintal of seed is applied.

25

7. A method according to claim 4 which comprises soaking the tuber in a composition comprising 0.1

BAD ORIGINAL to 100 g/1 of compound.

8. A method according to claim 1 substantially as hereinbefore described.

9. A plant propagation product, with the

5 exception of wheat grains of the Talent variety, comprising a compound which is 2-(4-chlorobenzylidene)-5,5-diraethyl-l(1H-1,2,4-triazol-l-ylmethyl)-1-cyclopentanol.

10. A plant propagation product according to claim 9, which is a seed.

10

11. A plant propagation product according to claim 10, wherein the seed is: a dicotyledon seed which is pea, cucumber, soybean, melon, cotton, sunflower, rape, bean, flax or beet; or a monocotyledon seed which is soft winter wheat with the exception of the Talent variety,

15 hard wheat, soft spring wheat, barley, rye, maize or rice.

12. A plant propagation product according to claim 10 or 11, wherein the seeds are coated with 0.1 to Oo0 g of compound per quintal of seed.

13. A plant propagation product according to 20 claim 12 wherein the seeds are coated with 1 to 400 g of compound per quintal of seed.

14. A plant propagation product according to claim 9, which is a potato tuber.

15. A plant propagation product according to • > claim 14, which has been soaked in a composition containing o.l g/1 to 100 g/1 of compound.

---. - -R

ΒΑΠ ORIGINAL

- 27

16. A plant propagation product according to claim 9 substantially as hereinbefore described.

17. A fungicidal composition intended especially for implementing a method according to any one

5 of claims 1 to 8, with the exception of the treatment of wheat of the Talent variety, comprising a compound which is 2-(4-chlorobenzylidene)-5,5-dimethyl-1-(1H-1,2,4-triazol-lylmethyl)-1-cyclopentanol, an agriculturally acceptable inert carrier and/or an agriculturally acceptable surface10 active agent.

18. A fungicidal composition according to claim 17, wherein the propagation products are seeds of:

a dicotyledon which is pea, cucumber, soybean, melon, cotton, sunflower, rape, bean, flax or beet; or

15 a monocotyledon which is hard wheat, soft spring wheat, barley, rye, maize or rice.

19. A fungicidal composition according to claim 17 or 18, which comprises 0.5 to 95% by weight of compound.

20 20. A fungicidal composition intended exclusively for implementing a method according to any one of claims 1 to 8, to seeds cf soft winter wheat and whiah contains 2-(4-chlorobenzylidene)-5,5-dimethyl-1-(1H-1,2,4criazol-l-ylmethyl)-1-cyclopentanol, an agriculturally

25 acceptable inert carrier and/or an agriculturally acceptable surface-active agent.

AP 0 0 0 2 0 2

DAD ORIGINAL

21. A fungicidal composition according to claim 20, wherein the seeds are wheat seeds of the Talent variety.

22. A fungicidal composition according to 5 claim 20 or 21, which comprises 0.5 to 95% by weight of active material.

23. A fungicidal composition which comprises 2-(4-chlorobenzylidene)-5,5-dimethyl-1-(1H-1,2,4-triazol-lylmethyl)-l-cyclopentanol, in association with an

10 agriculturally acceptable carrier and/or an agriculturally acceptable surface-active agent and which comprises a marker.

24. A fungicidal composition according to claim 17, 20 or 23 substantially as hereinbefore described.