WO2014180215A1

WO2014180215A1 - Agrochemical composition, method for its preparation and use thereof

Info

Publication number: WO2014180215A1
Application number: PCT/CN2014/075131
Authority: WO
Inventors: James Timothy Bristow
Original assignee: Rotam Agrochem International Co. Ltd
Priority date: 2013-05-07
Filing date: 2014-04-11
Publication date: 2014-11-13
Also published as: AU2014264173B2; GB2513859B; GB2513859A; CN105120668A; AU2017100044A4; GB201308136D0; TWI646894B; AU2014264173A1; CN105120668B; TW201446142A

Abstract

An agrochemical composition is provided,the composition comprising iprodione and at least one macrolide compound selected from compounds of the general formula(I) in which R₁, R₂, R₃, R₄, R₅and R₆independently represent hydrogen or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl group;and substructures A and B independently denote that the two carbon atoms to which each of these substructures is bonded are linked by a single bond,by a double bond or by a single bond and an epoxy bridge; and compounds of the general formula(II) in which R₇is hydrogen; R₈is hydrogen or a group of the general formula(III) in which R₉is OH or CH₃-CO-NH–; the group of formula (IV) or the group of formula(V): D is a single bond,in which case both R₁₀and R₁₁are hydrogen or are combined to form the group=N-O-CH₃, or D is a double bond and R₁₀and R₁₁are combined to represent hydrogen; R₁₂is an alkyl, alkenyl or phenyl group; and R₁₃is OH, R₁₄is hydrogen or R₁₃and R₁₄are combined to form the group=N-OH. The composition finds use in the control of pests at a locus,in particular nematodes.

Description

AGROCHEMICAL COMPOSITION, METHOD FOR ITS PREPARATION AND USE THEREOF

The present invention relates to an agrochemical composition, in particular to a nematicidal composition. The present invention also relate to a method for preparing the said agrochemical composition and to its use in controlling nematodes.

Nematodes are microscopic round worms. They can generally be described as aquatic, triploblastic, unsegmented, bilaterally symmetrical roundworms, which are colourless, transparent, usually bisexual, and worm-shaped (vermiform), although some can become swollen (pyroform). It has been suggested that nematodes are the most abundant form of animal life and that to date only about 3% of nematode species have been studied in detail.

Plant parasitic nematodes typically feed on the roots or shoots of plants. The nematodes can be ectoparasites, that is feeding on the exterior of a host plant, or endoparasites, that is living/feeding inside the host plant. Parasitic nematodes can be migratory or sedentary. They constitute severe plant production constraints in many agronomic and horticultural crops. Severe infestations of endoparasitic nematodes, such as certain root-knot or cyst nematodes, can result in yield losses of from 10% to 50%. Worldwide crop losses due to plant parasitic nematodes have been estimated at $80 billion annually.

Some of the most commercially significant plant parasitic nematodes are: Meloidogyne; Root-knot nematode Pratylenchus; Lesion nematode Heterodera; Cyst nematode Globodera; Cyst nematode

Ditylenchus; Stem and bulb nematode

Tylenchulus; Citrus nematode Xiphinema; Dagger nematode

Radopholus; Burrowing nematode

Rotylenchulus; Reniform nematode

Helicotylenchus; Spiral nematode Belonolaimus; Sting nematode.

Nematodes are a serious pest and methods to control their parasitic activities are an important feature in maximising crop production in modern intensive agriculture. Current pest management options for controlling nematodes are very limited. Soil fumigants and effective non-fumigant nematicides, especially carbamate and organophosphate compounds, are increasingly under regulatory pressure because of potential undesirable effects on users, consumers, and the environment. Other effective methods to reduce plant-parasitic nematode populations, such as exposing infested soil to heat by steam treatment, are technically difficult and too costly for general or widespread application in the field. Certain seed treatments, for example using abamectin as a nematicide, have been shown to effectively protect roots of young seedlings against various plant pests, including plant-parasitic nematodes. Non-protected root systems show stunting, and in the case of root-knot nematodes (Meloidogyne spp.) show more severe galling, in comparison to abamectin-protected plants. These below-ground differences are reflected in significant height and dry weight differences of the shoots. However, seed treatment protection against nematode invasion often lasts for only a relatively short period of time.

Accordingly, there is a significant need for an improved nematicidal composition and methods of controlling nematodes, as well as other plant pests and pathogens. It would be an advantage if the treatment could be long lasting. It has now been found that an improved agrochemical composition can be prepared from a combination of iprodione and at least one macrolide compound.

Accordingly, in a first aspect, the present invention provides an agrochemical composition comprising iprodione and at least one macrolide compound selected from compounds of the general formula (I):

in which R_h R₂, R₃, R₄, R5 and R₆ independently represent hydrogen or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyi, aryl or heterocyclyl group; and substructures A and B independently denote that the two carbon atoms to which each of these substructures is bonded are linked by a single bond, by a double bond or by a single bond and an epoxy bridge; and compounds of the general formula (II):

the group of formula (IV):

or the group of formula (V):

O CH₃

(V)

D is a single bond, in which case both R₁₀ and Rn are hydrogen or are combined to form the group =N-0-CH₃, or D is a double bond and R₁₀ and Rn are combined to represent hydrogen;

Ri2 is an alkyl, alkenyl or phenyl group; and

R₁₃ is OH, R₁₄ is hydrogen or R₁₃ and R₁₄ are combined to form the group =N-OH.

It has surprisingly been found that the combination of iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) provide a synergistic effect and improved control of nematodes and other plant pests and pathogens. In particular, the combination exhibits surprisingly high activity in controlling nematodes in crops, such as tomato, pepper, cucumber, melons, coffee and soybeans.

The term "synergistic" as used herein is not to be understood in this connection as being restricted to the pesticidal activity of the combination, but also refers to other advantageous properties, compared with iprodione and the macrolide compounds applied individually. Examples of such advantageous properties which may be mentioned are: extension of the pesticidal spectrum of action to other pests, for example to resistant strains; reduction in the application rate of the macrolide compound, or control of the target pests with the aid of the compositions according to the invention at an application rate of iprodione and the macrolide compound alone that is ineffective; enhanced crop safety; improved quality of produce, such as higher content of nutrient or oil, better fiber quality, enhanced shelf life, reduced content of toxic products, for example such as mycotoxins, reduced content of residues or unfavorable constituents of any kind or better digestability; improved tolerance to unfavorable temperatures, draughts or salt content of water; enhanced assimilation rates, such as nutrient uptake, water uptake and photosynthesis; favorable crop properties such as altered leaf area, reduced vegetative growth, increased yields, favorable seed shape/seed thickness or germination properties, altered colonialisation by saprophytes or epiphytes, reduction of senescense, improved phytoalexin production, improved of accelerated ripening, flower set increase, reduced boll fall and shattering, better attraction to beneficials and predators, increased pollination, reduced attraction to birds.

The agrochemical composition of the present invention is advantageous for controlling nematodes and other plant pests and pathogens, including such pests as Meloidogyne incognita and Meloidogyne javanica, in crops, such as tomato, pepper, cucumber, melons, coffee and soybeans. The composition of the present invention comprises iprodione. Iprodione is the common name for the compound 3-(3,5-dichlorophenyl)-N-isopropyl-2,4- dioxoimidazolidine-1 -carboxamide. Iprodione was first disclosed in US 3,755,350 as a fungicide, in particular for the control of dollar spot, brown patch, and leaf spot diseases in bentgrass. Existing registrations for this fungicide also include the control of a wide range of foliar and soil diseases on amenity turf, commercial ornamentals, vegetables, and tree fruits, as well as the control of Sclerotinia blight in peanut. The activity of iprodione as a nematicide is disclosed in EP 1 941 798.

The composition of the present invention further comprises a macrolide selected from the compounds of general formulae (I) and (II), as set out above. The macrolide compounds of formulae (I) and (II) are known in the art. The macrolides are the classes of substances which are known as milbemycins and avermectins, and disclosed, for example, in US 4,310,519, US 5,077,298, DE 2 717 040 and US 4,427,663. The term 'macrolides' is also to be understood as meaning, in accordance with the present invention, the derivatives of these substances, that is, for example, milbemycin oxime, moxidectin, ivermectin, abamectin, emamectin, and doramectin, and also the spinosyns of general formula (I). In the compounds of general formula (I), Ri is preferably hydrogen or a lower alkyl group, more preferably having from 1 to 4 carbon atoms, still more preferably methyl. R₂ is preferably a heterocyclyl group, more preferably a group of the general formula (VI):

(VI) in which R₁₅ is a lower alkyl group, preferably having from 1 to 4 carbon atoms, in particular methyl or ethyl. R₃ is most preferably hydrogen. R₄ is preferably lower alkyl, more preferably having from 1 to 3 carbon atoms, in particular methyl. R₅ is preferably a heterocycle group, more preferably the group of formula (VII):

R₆ is preferably a lower alkyl group, more preferably having from 1 to 3 carbon atoms, particular ethyl. In the compounds of general formula (I), A and B are each preferably single or a double bond.

Preferred compounds of general formula (I) are spinosad and spinetoram. In the compounds of general formula (II), Ri₂ is preferably an alkyl group having from 1 to 8 carbon atoms, more preferably from 1 to 6 carbon atoms, still more preferably from 1 to 4 carbon atoms. The alkyl group may be straight chain or branched, preferably straight chain. Preferred alkyl groups are methyl, ethyl, propyl and butyl. Alternatively, R₁₂ is an alkenyl group, preferably having from 2 to 10 carbon atoms, more preferably from 2 to 8 carbon atoms, still more preferably from 2 to 4 carbon atoms. The alkenyl group may be straight chain or branched, preferably branched. In one embodiment, a branched C₆ alkenyl group is preferred. As a further alternative, R₁₂ is preferably a phenyl group. Preferred macrolide compounds of general formula (II) are ivermectin, abamectin, milbemectin, moxidectin, eprinomectin, lepimectin, selamectin and doramectin.

The macrolide compounds of general formulae (I) and (II) may be employed in its free form or in the form of a salt. The agrochemically compatible salts of the macrolide compounds are, for example, acid addition salts of inorganic and organic acids, in particular of hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, perchloric acid, phosphoric acid, formic acid, acetic acid, tri-fluoroacetic acid, oxalic acid, malonic acid, toluenesulfonic acid or benzoic acid.

Abamectin is one preferred macrolide compound for use in the composition of the present invention. Abamectin is a mixture of avermectin B_1a and avermectin B_{1 b} and is described, for example, in The Pesticide Manual, l OthEd. (1994), The British Crop Protection Council, London, page 3. Abamectin is a commercially available compound.

Another preferred macrolide compound is emamectin, that is 4"-De-oxy-4"-epi-N- methylamino avermectin B_{1 b}/B_1a, known from US 4,874,749. Emamectin is also known as MK-244 and is described in Journal of Organic Chemistry, Vol. 59 (1994), pages 7704- 7708. Agrochemically especially useful salts of emamectin are described in US 5,288,710.

A further preferred macrolide compound is the group of compounds consisting of the spinosyns and their derivatives; the group of compounds consisting of the naturally occurring spinosyns; and the group of compounds consisting of the derivatives of the naturally occurring spinosyns. Preferably, the active ingredient comprises spinosyn A, spinosyn D, or a mixture of spinosyn A and spinosyn D. An especially component is spinosad. Spinosad is known from the "The Pesticide Manual", 1 1 ^th Ed. (1997), The British Crop Protection Council, London, United Kingdom, pages 1272-1273.

Preferred embodiments of the present invention are a composition which comprises, as the macrolide active ingredient, abamectin or spinosad, in particular in the free form, or emamectin, in particular as a salt, especially the benzoate salt.

Iprodione may be present in the composition in any suitable amount. In some embodiments of the invention, iprodione is present in an amount of 1 % to 99% by weight, preferably 30% to 90%, more preferably 50% to 80%.

The macrolide compounds of general formulae (I) and (II) may be present in the composition in any suitable amount. In some embodiments of the invention, the macrolide compound selected from the compounds of general formulae (I) and (II) is present in an amount of 1 % to 50% by weight, preferably 5% to 40%, more preferably 10% to 30%.

The composition may comprise a single macrolide compound selected from the compounds of general formulae (I) and (II). Alternatively, the composition may comprise a mixture of two or more macrolide compounds of formulae (I) and (II).

The weight ratio of iprodione and the macrolide compounds selected from the compounds of general formulae (I) and (II) may be in the range of from 1 :100 to 100:1 , preferably from 1 :50 to 50:1 .

The agrochemical composition of the present invention may further contain one or more agriculturally acceptable auxiliaries. The auxiliaries employed in the composition and their amounts will depend upon the type of formulation and/or the manner in which the formulation is to be applied by the end user. Suitable auxiliaries are customary formulation adjuvant or components, such as solvents, surfactants, stabilizers, anti- foaming agents, anti-freezing agents, preservatives, antioxidants, colorants, thickeners and inert fillers. Such auxiliaries are known in the art and are commercially available. Their use in the formulation of the compositions of the present invention will be apparent to the person skilled in the art.

The composition may comprise one or more solvents. The solvent may be organic or inorganic. Suitable solvents are selected from customary solvents which thoroughly dissolve the agrochemically active substances employed. Suitable solvents are known in the art and are commercially available. Examples of suitable solvents include water; aromatic solvents, such as xylene (for example solvent products commercially available from Solvesso™); mineral oils; animal oils; vegetable oils; alcohols, for example methanol, butanol, pentanol, and benzyl alcohol; ketones, for example cyclohexanone, and gamma-butyrolactone; pyrrolidones, such as NMP, and NOP; acetates, such as glycol diacetate; glycols; fatty acid dimethylamides; fatty acids; and fatty acid esters.

The composition optionally further comprises one or more surfactants. Suitable surfactants are known in the art and include, but are not limited to, alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, arylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose and ethylene oxide/propylene oxide block copolymers. Suitable surfactants are commercially available.

The composition optionally further comprises one or more polymeric stabilizers. Suitable polymeric stabilizers that may be used in the present invention include, but are not limited to, polypropylene, polyisobutylene, polyisoprene, copolymers of monoolefins and diolefins, polyacrylates, polystyrene, polyvinyl acetate, polyurethanes or polyamides. Suitable stabilizers are known in the art and are commercially available.

The composition may include an anti-foaming agent. Suitable anti-foam agents include those substances which can normally be used for this purpose in agrochemical compositions and will be readily apparent to the person skilled in the art. Suitable anti- foam agents are known in the art and are commercially available. Particularly preferred antifoam agents are mixtures of polydimethylsiloxanes and perfluroalkylphosphonic acids, such as the silicone anti-foam agents (for example commercially available from GE or Compton). One or more preservatives may also be present in the composition. Suitable preservatives include those substances which can normally be used for this purpose in agrochemical compositions of this type and again are well known in the art. Suitable examples that may be mentioned include Preventol® (commercially available from Bayer AG) and Proxel® (commercially available from Bayer AG).

Further, the composition may include one or more antioxidants. Suitable antioxidants are substances which can normally be used for this purpose in agrochemical compositions, as is known in the art. Preference is given, for example, to butylated hydroxytoluene. The compositions may further comprise one or more solid adherents. Such adherents are known in the art and available commercially. They include organic adhesives, including tackifiers, such as celluloses of substituted celluloses, natural and synthetic polymers in the form of powders, granules, or lattices, and inorganic adhesives such as gypsum, silica, or cement. The compositions may further comprise one or more inert fillers. Such inert fillers are known in the art and available commercially. Suitable fillers include, for example, natural ground minerals, such as kaolins, aluminas, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, or synthetic ground minerals, such as highly dispersed silicic acid, aluminum oxide, silicates, and calcium phosphates and calcium hydrogen phosphates. Suitable inert fillers for granules include, for example, crushed and fractionated natural minerals, such as calcite, marble, pumice, sepiolite, and dolomite, or synthetic granules of inorganic and organic ground materials, as well as granules of organic material, such as sawdust, coconut husks, corn cobs, and tobacco stalks.

The compositions may further comprise one or more thickeners. Suitable thickeners include those substances which can normally be used for this purpose in agrochemical compositions. Examples of suitable thickeners include gums, such as xanthan gum, PVOH, cellulose and its derivatives, clay hydrated silicates, magnesium aluminum silicates or a mixture thereof. Again, such thickeners are known in the art and are available commercially. In some embodiments of the present invention, the agrochemical composition may be applied and used in pure form, or more preferably together with at least one of the auxiliaries, as described hereinabove.

The composition of the present invention may also comprise other active ingredients for achieving specific effects, for example, bactericides, fungicides, insecticides, nematicides, molluscicides or herbicides. Suitable compounds for providing the aforementioned activities are known in the art and are commercially available.

The agrochemical composition of the present invention may be formulated in different ways, depending upon the circumstances of its use. Suitable formulation techniques are known in the art and include water-dispersible powders, dusts, pastes, water-dispersible granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates, suspoemulsion, aerosols, or microencapsulation suspensions. More preferably, the agrochemical composition is formulated as water-dispersible granules, an emulsifiable concentrate, a suspension concentrate, a suspoemulsion, or a microencapsulation suspension.

Examples of formulation types for use in the present invention are as follows:

A) Water-soluble concentrate (SL)

Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are dissolved in a water-soluble solvent. One or more wetting agents and/or other auxiliaries may be included. The active compound dissolves upon dilution with water.

B) Emulsifiable concentrates (EC) Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are dissolved in a water-immiscible solvent, preferably with the addition of one or more non-anionic emulsifiers and anionic emulsifiers. The mixture is agitated, for example by stirring, to get a uniform formulation. Dilution with water provides a stable emulsion. C) Emulsions (EW)

Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are dissolved in one or more suitable water immiscible solvents, preferably with the addition of one or more non-anionic emulsifiers and anionic emulsifiers. The resulting mixture is introduced into water by appropriate means, such as an emulsifying machine, to provide a homogeneous emulsion. Dilution with water gives a stable emulsion.

D) Suspension (SC, OD, FS)

In an agitated ball mill, iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are comminuted, preferably with the addition of one or more dispersants and wetting agents, and water or solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound.

E) Water-dispersible granules and water-soluble granules (WG, SG)

Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are ground finely, preferably with the addition of one or more dispersants and wetting agents, and prepared as water-dispersible or water-soluble granules by means of suitable techniques, for example by extrusion, drying in a spray tower, or by processing in a fluidized bed. Dilution with water gives a stable dispersion or solution of the active compound.

F) Water-dispersible powders and water-soluble powders (WP,SP)

Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are ground in a suitable apparatus, such as a rotor-stator mill, preferably with addition of one or more dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active compound.

G) Granules (GR, FG, GG, MG) Iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) are finely ground in a suitable apparatus, with addition of up to 99.5 parts by weight of carriers. Granules are then prepared either by suitable techniques, such as extrusion, spray-drying or using a fluidized bed.

In a further aspect, the present invention provides the use of a composition as hereinbefore described in the control of pests at a locus, in particular for use as a nematicide.

In a still further aspect, the present invention provides a method for controlling pests, in particular nematodes, at a locus, comprising applying to the locus a composition as hereinbefore described.

In use, the composition of the present invention may be applied to the target plant or plant of interest, to one or more parts thereof (such as leaves or seeds), or to the locus thereof.

In a still further aspect, the present invention provides a method of controlling nematodes and other plant pests and pathogens at a locus, comprising applying to the locus iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II). The aforementioned active compounds may be applied separately, for example simultaneously or consecutively, to the locus. Alternatively, the active compounds are applied together, preferably in the form of a composition as hereinbefore described.

In particular, the agrochemical composition and the methods of the present invention may be applied in controlling nematodes and other plant pests and pathogens, for example: nematodes selected from the group consisting of root-knot, cyst, burrowing, dagger, lance, pin, reniform, lesion, ring, spiral, sting, stubby, stunt, stem and bulb, seed gall and foliar nematodes;

Paratrichodorus minor, Longidorus spp., Helicotylenchus pseudorobustus, Hoplolaimus galeatus, H. columbus, H. tylenchiformis, Trichodorus proximus, Xiphinema index, X. americanum, Ditylenchus dipsaci, D. destructor, Nacobbus aberrans, Longidorus breviannulatus, L. africanus, Mesocriconema xenoplax, Aphelenchoides besseyi, A. fragariae, Zygotylenchus guevarai, Belonolaimus longicaudatus, B. gracilis, Anguina tritici, Rotylenchulus spp., Subanguina spp., Criconemella spp., Criconemoides spp., Dolichodorus spp., Hemicriconemoides spp., Hemicycliophora spp., Hirschmaniella spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., Quinisulcius spp., Scutellonema spp., and Tylenchorhynchus spp.;

from the group of Anguina spp.; Aphelenchoides spp.; Ditylenchus spp.;

from the group of Globodera spp., for example G. rostochiensis, and G. pallida; Longidorus spp.;

from the group of Meloidogyne spp., for example Meloidogyne incognita and Meloidogyne javanica;

from the group of Pratylenchus, for example P. neglectans, P. scribneri, P. thornei, P. brachyurus, P. coffeae, P. zeae, and P. penetrans

from the group of Radopholus spp., for example Radopholus similis, and R. citrophilus;

Trichodorus spp.; Tylenchulus, for example Tylenchulus semipenetrans; and Xiphinema spp.;

from the group of Heterodera spp., for example H. schachtii, H. avenae, H. glycines, H. ^'carotae, H. goettingiana, H. zeae and H. trifolii; and

from the group of Meloidogyne spp., for example M. incognita, M. javanica, M. hapla, M. arenaria, M. chitwoodi, M. graminis, M. mayaguensis, M. fallax, M. naasi.

from the order Lepidoptera, for example Acleris spp., Adoxophyes spp., especially Adoxophyes reticulana; Aegeria spp., Agrotis spp., especially Agrotis spinifera; Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyrotaenia spp., Autographa spp., Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydia spp., especially Cydia pomonella; Diatraea spp., Diparopsis castanea, Earias spp., Ephestia spp., especially E. Khiiniella; Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., especially H. virescens and H. zea; Hellula undalis, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lobesiaspp., Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Operophtera spp., Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Pectinophora spp., Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodopteralittoralis, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni and Yponomeuta spp.;

from the order Coleoptera, for example Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Leptinotarsa decemlineata, Lissorhoptrus spp., Melolontha spp., Oryzaephilus spp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Tribolium spp. and Trogoderma spp.;

from the order Orthoptera, for example Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. and Schistocerca spp.; from the order Isoptera, for example Reticulitermes spp.;

from the order Psocoptera, for example Liposcelis spp.;

from the order Anoplura, for example Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;

from the order Mallophaga, for example Damalinea spp. and Trichodectes spp.; from the order Thysanoptera, for example Frankliniella spp., Hercinothrips spp., Taeniothrips spp., Thrips palmi, Thrips tabaci and Scirtothrips aurantii;

from the order Heteroptera, for example Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp. Eurygaster spp. Leptocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotinophara spp. and Triatoma spp.; from the order Homoptera, for example Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella aurantii, Aphididae, Aphiscraccivora, A. fabae, A. gosypii; Aspidiotus spp., Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus hesperidum, Empoasca spp., Eriosoma lanigerum, Erythroneura spp., Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp., Macrosiphus spp., Myzus spp., especially M.persicae; Nephotettix spp., especially N. cincticeps; Nilaparvata spp., especially N. lugens; Paratoria spp., Pemphigus spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., especially P. Fragilis, P. citriculus and P. comstocki; Psylla spp., especially P. pyri; Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri;

from the order Hymenoptera, for example Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.;

from the order Diptera, for example Aedes spp., Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis pomonella, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.;

from the order Siphonaptera, for example Ceratophyllus spp. and Xenopsylla cheopis;

from the order Thysanura, for example Lepisma saccharina and

from the order Acarina, for example Acarus siro, Aceria sheldoni; Aculus spp., especially A. schlechtendali; Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., especially B. californicus and B. phoenicis; Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., especially E.carpini and E. orientalis; Eriophyes spp., especially E. vitis; Hyalomma spp., Ixodes spp., Olygonychus pratensis, Ornithodoros spp., Panonychus spp., especially P. ulmi and P. citri; Phyllocoptruta spp., especially P. oleivora; Polyphagotarsonemus spp., especially P. latus; Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Tarsonemus spp. and Tetranychus spp., in particular T. urticae, T. cinnabarinus and T. Kanzawai.

The composition and method of the present invention finds particular advantageous use in the control of nematodes in crops. Suitable target crops include, in particular, cereals, such as wheat, barley, rye, oats, rice, maize, sorghum, millet and manioc; beet, such as sugar beet and fodder beet; fruit, such as pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries, or berries, for example strawberries, raspberries and blackberries; leguminous plants, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucurbitaceae, such as marrows, cucumbers and melons; fibrous plants, such as cotton, flax, hemp and jute; citrus fruit, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, such as avocados, cinnamon and camphor; and tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas, natural rubber plants, eucalyptus, as well as ornamental plants. Especially preferred crops for treatment are tomato, pepper, cucumber, melons, coffee and soybeans.

In general, the composition may be prepared and applied such that the agrochemical composition of iprodione and the macrolide compounds of formulae (I) and (II) are applied at any suitable rate, as demanded by the locus to be treated. The application rate may vary within wide ranges and depends upon such factors as the soil constitution, the type of application (foliar application; seed dressing; application in the seed furrow), the target crop plant, the nematodes to be controlled, the climatic circumstances prevailing in each case, and other factors determined by the type of application, timing of application and target crop. In general, the application rates are from 1 to about 2000 g of the agrochemical composition per hectare, in particular 10 to 1000 g/ha, preferably 10 to 500 g/ha, more preferably 10 to 200 g/ha.

According to the present invention, the iprodione and the macrolide active compounds of general formulae (I) and (II) may be applied in any suitable form, as described above, and applied to the locus where control is desired either simultaneously or in succession at short intervals, for example on the same day. In a preferred embodiment, iprodione and the macrolide compound of general formulae (I) and (II) are applied simultaneously, in particular by way of a composition of the present invention. Iprodione and the macrolide compounds of general formulae (I) and (II) may be applied to the plant or locus in any order. Each compound may be applied just once or a plurality of times. Preferably, each of the compounds is applied a plurality of times, in particular from 2 to 5 times, more preferably 3 times.

According to the present invention, the active compounds may be applied at any suitable time. In some embodiments of the present invention, the active compounds are applied to the soil or the locus of the plant prior to planting, during planting, or after planting. Such a treatment may take place by conventional methods known in the art, for instance, drip-irrigation, spray, and soil fumigation. In some embodiments, the active compounds are applied to the plant propagation material, such as a seed, by seed coating. These application methods and corresponding application machines are known in the art.

Iprodione and the macrolide compounds of general formulae (I) and (II) may be applied in any amounts relative to each other. In particular, the relative amounts of the compounds to be applied to the plant or locus are as hereinbefore described, with the ratio of iprodione and the macrolide compounds of general formulae (I) and (II) preferably being in the range of from 1 :100 to 100:1 .

In the event iprodione and the macrolide compounds of general formulae (I) and (II) are applied simultaneously, they can be obtained from a separate formulation source and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry), optionally with other pesticides, or they can be obtained as a single formulation mixture source (known as a pre-mix, concentrate, formulated compound (or product)), and optionally mixed together with other pesticides. Embodiments of the present invention are now described, for illustrative purposes only, by way of the following examples.

Where not otherwise specified throughout this specification and claims, percentages are by weight.

Formulation Examples Example 1 Water-soluble concentrates (SL)

A water-soluble concentrate formulation was prepared having the following composition:

Iprodione 25 g

Abamectin 5 g

TWEEN 80 (Sorbitan monooleate ethoxylate) 10 g

N-methyl pyrrolidone balance to 100 g

Example 2 Emulsifiable concentrates (EC)

An emulsifiable concentrate was prepared having the following composition:

Iprodione 50 g

Abamectin 2.5 g

TWEEN 80 (Sorbitan monooleate ethoxylate) 10 g

Calcium dodecylphenylsulfonate (70B) 4 g

Solvesso 200 10 g

N-methyl pyrrolidone balance to 100 g

Example 3 Water-dispersible powders (WP) A water dispersible powder was prepared having the following composition:

Iprodione 80 g

Emamectin Benzoate 0.8 g

Dispersogen1494 (sodium salt of a cresol-formaldehyde 5 g condensation)

Kaolin balance to 100 g

Example 4 Water-dispersible granules (WG)

A water dispersible granule formulation was prepared having the following composition:

Iprodione 60 g

Spinosad 3 g

Poly vinyl alcohol 2 g

Dispersogen1494 (sodium salt of a cresol-formaldehyde 5 g condensation)

Kaolin balance to 100 g

Example 5 Suspension

A suspension formulation was prepared having the following composition: Iprodione 2 g

Abamectin 2 g

Dispersogen 4387 (anionic polymeric ester) 5 g

Propylene glycol 5 g

Xanthan Gum 2 g

Water balance to 100 g

Example 6 Water-soluble concentrates (SL)

A water soluble concentrate was prepared having the following composition:

Iprodione 40 g

Spinosad 4 g

TWEEN 80 (Sorbitan monooleate ethoxylate) 10 g

N-methyl pyrrolidone 5 g

Water balance to 100 g

Example 7 Water-dispersible granule (WG)

A water dispersible granule was prepared having the following composition: Iprodione 16 g

Abamectin 4 g

Poly vinyl alcohol 2 g

Dispersogen 1494 (sodium salt of a cresol-formaldehyde 5 g condensation)

Kaolin balance to 100 g

Example 8 Flowable -seed treatment (FS)

A flowable seed treatment was prepared having the following composition:

Iprodione 20 g

Abamectin 40 g

Dispersogen 4387 (anionic polymeric ester) 5 g

Propylene glycol 5 g

Xanthan Gum 2 g

Poly vinyl pyrrolidone 4 g

Carmosine 12 g

Water balance to 100 g

Example 9 Water-soluble concentrate (SL)

A water soluble concentrate was prepared having the following composition: Iprodione 25 g

Emamectin Benzoate 2 g

TWEEN 80 (Sorbitan monooleate ethoxylate) 10 g

N-methyl pyrrolidone Balance to 100 g

Example 10 Water-dispersible granule (WG) A water-dispersible granule formulation was prepared having the following composition:

Iprodione 8 g

Emamectin Benzoate 16 g

Poly vinyl alcohol 2 g

Dispersogen 1494 (sodium salt of a cresol-formaldehyde 5 g condensation)

Kaolin balance to 100 g

Example 1 1 Oil-in-water emulsion (EW)

An oil-in-water emulsion formulation was prepared having the following composition: Iprodione 8 g Abamectin 4 g Solvesso 200 20 g

EL360 (ethoxylated soybean oil) 5 g 70B (calcium dodecylphenylsulfonate) 3 g Water balance to 100 g

Example 12 Suspension

A suspension formulation was prepared having the following composition:

Iprodione 20 g

Spinosad 9 g

Dispersogen 4387 (anionic polymeric ester) 5 g

Propylene glycol 5 g

Xanthan Gum 2 g

Water balance to 100 g

Test Examples

Test 1 - Nematicidal activity against Meloidogyne incognita To plastic boxes with a base of 0.25 m² and containing 2 to 3 cm deep layer of sandy soil, 100 Meloidogyne incognita was introduced uniformly. Three replicates of each treatment were tested. Iprodione (Rovral® from Bayer), abamectin (Agador® from Syngenta), emamectin benzoate (Affirm® from Syngenta), spinosad (Success from Dow) and formulations of each of Examples 1 to 12 set out above were applied. Efficacy was assessed based on mortality rate after 24 and 48 hours. The results are set out in the table below.

% of % of

Rate of

Mortality Mortality

Treatment application (g Al

after 24 after 48

/ha)

hours hours

Untreated 0 0 0

Iprodione

200 10 15 (Rovral® from Bayer)

Abamectin

40 23 26 (Agador® from Syngenta)

Emamectin benzoate

16 19 25 (Affirm® from Syngenta)

Spinosad

90 23 27 (Success from Dow)

Ex. 1 Iprodione + Abamectin 200 + 40 99 100

Ex. 2 Iprodione + Abamectin 200 + 10 77 84

Iprodione + Emamectin

Ex. 3 200 + 2 72 89

benzoate

Ex. 4 Iprodione + Spinosad 200 + 10 66 79

Ex. 5 Iprodione + Abamectin 40 + 40 65 74

Ex. 6 Iprodione + Spinosad 200 + 20 74 85

Ex. 7 Iprodione + Abamectin 160 + 40 87 93

Ex. 8 Iprodione + Abamectin 20 + 40 52 67

Iprodione + Emamectin

Ex. 9 200 + 16 98 100

benzoate Iprodione + Emamectin

Ex. 10 8 + 16 60 73 benzoate

Ex. 1 1 Iprodione + Abamectin 80 + 40 79 85

Ex. 12 Iprodione + Spinosad 200 + 90 98 100

As can be seen from the above table, the formulations prepared according to the present invention exhibited significantly improved efficacy in controlling the target pests than the commercially available compositions.

Test 2 - Nematicidal activity against Meloidogyne javanica

The general procedure of Test 1 was repeated to assess the nematicidal activity against Meloidogyne javanica.

The results are set out in the table below.

% of % of

Rate of

Mortality Mortality

Treatment application (g Al

after 24 after 48

/ha)

hours hours

Untreated 0 0 0

Iprodione

200 12 17 (Rovral® from Bayer)

Abamectin

40 22 26 (Agador® from Syngenta)

Emamectin benzoate

16 20 27 (Affirm® from Syngenta)

Spinosad

90 25 31 (Success from Dow)

Ex. 1 Iprodione + Abamectin 200 + 40 99 100

Ex. 2 Iprodione + Abamectin 200 + 10 74 81 Iprodione + Emamectin

Ex. 3 200 + 2 73 89

benzoate

Ex. 4 Iprodione + Spinosad 200 + 10 67 81

Ex. 5 Iprodione + Abamectin 40 + 40 65 74

Ex. 6 Iprodione + Spinosad 200 + 20 76 89

Ex. 7 Iprodione + Abamectin 160 + 40 86 93

Ex. 8 Iprodione + Abamectin 20 + 40 54 69

Iprodione + Emamectin

Ex. 9 200 + 16 99 100 benzoate

Ex. Iprodione + Emamectin

8 + 16 61 72 10 benzoate

Ex.

Iprodione + Abamectin 80 + 40 79 87

1 1

Ex.

Iprodione + Spinosad 200 + 90 98 100

12

Test 3 - Nematicidal effects on Tomato

Tomato seeds were sown into seeding trays with commercial seedling substrate and after 2 weeks the plants were transplanted into 10-cm pulp pots filled with 250 g (dry weight) steam-pasteurized sand. Each pot was infested with ca. 30000 eggs of Meloidogyne javanica. Iprodione (Rovral® from Bayer), abamectin (Agador® from Syngenta), emamectin benzoate (Affirm® from Syngenta), spinosad (Success from Dow) and formulations of each of Examples 1 to 12 set out above were applied. Pots were arranged in a randomized complete block design with 6 replications per treatment and incubated in greenhouse at ambient temperate and lighting. Plants were watered daily as needed. At one month after treatments, plant height and root galling were determined, based on a 0-10 gall rating where 0 = no galling and 10 = 100% of the root surface galled. The results are set out in the table below.

Rate of Numbers of

Plant Average applicatio egg

Treatment height root n (g AI masses/roo

(cm) galling /ha) t

Untreated 0 4.9 140 10

Iprodione

200 5.2 136 9 (Rovral® from Bayer)

Abamectin

40 5.9 120 7 (Agador® from Syngenta)

Emamectin benzoate

16 5.6 126 6 (Affirm® from Syngenta)

Spinosad

90 5.5 124 8 (Success from Dow)

Ex. 1 Iprodione + Abamectin 200 + 40 1 1 .3 56 0

Ex. 2 Iprodione + Abamectin 200 + 10 10.8 72 2

Iprodione + Emamectin

Ex. 3 200 + 2 9.7 91 1 benzoate

Ex. 4 Iprodione + Spinosad 200 + 10 8.3 72 2

Ex. 5 Iprodione + Abamectin 40 + 40 7.5 78 2

Ex. 6 Iprodione + Spinosad 200 + 20 9.4 58 1

Ex. 7 Iprodione + Abamectin 160 + 40 10.0 64 1

Ex. 8 Iprodione + Abamectin 20 + 40 6.9 85 3

Iprodione + Emamectin

Ex. 9 200 + 16 10.9 60 1 benzoate

Ex. Iprodione + Emamectin

8 + 16 7.7 1 13 2 10 benzoate

Ex.

Iprodione + Abamectin 80 + 40 8.7 69 2

1 1

Ex. Iprodione + Spinosad 200 + 90 10.7 47 1

Claims

in which R_{1 5} R₂, R₃, R₄, R5 and R₆ independently represent hydrogen or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyi, aryl or heterocyclyl group; and substructures A and B independently denote that the two carbon atoms to which each of these substructures is bonded are linked by a single bond, by a double bond or by a single bond and an epoxy bridge; and compounds of the general formula (II):

the group of formula (IV):

or the group of formula (V):

O CH₃

(V) D is a single bond, in which case both R₁₀ and Rn are hydrogen or are combined to form the group =N-0-CH₃, or D is a double bond and Ri₀ and Rn are combined to represent hydrogen;

Ri2 is an alkyl, alkenyl or phenyl group; and

2. The agrochemical composition according to claim 1 , wherein in the compounds of general formula (I) Ri is hydrogen or lower alkyl.

3. The agrochemical composition according to claim 2, wherein is methyl.

4. The agrochemical composition according to any preceding claim, wherein R₂ is a group of the general formula (VI):

(VI) in which R15 is a lower alkyl group.

5. The agrochemical composition according to claim 4, wherein R₁₅ is methyl or ethyl.

6. The agrochemical composition according to any preceding claim, wherein R₃ is hydrogen.

7. The agrochemical composition according to any preceding claim, wherein R₄ is lower alkyl.

8. The agrochemical composition according to claim 7, wherein R₄ is methyl.

9. The agrochemical composition according to any preceding claim, wherein R₅ is a group of the general formula (VII):

10. The agrochemical composition according to any preceding claim, wherein R₆ is lower alkyl.

1 1 . The agrochemical composition according to claim 10, wherein R₆ is methyl.

12. The agrochemical composition according to any preceding claim, wherein A and B are each a single or a double bond.

13. The agrochemical composition according to any preceding claim, wherein the compound of general formula (I) is spinosad or spinetoram.

14. The agrochemical composition according to any preceding claim, wherein in the compound of general formula (II) Ri₂ is an alkyl group having from 1 to 4 carbon atoms.

15. The agrochemical composition according to any of claims 1 to 13, wherein in the compound of general formula (II) Ri₂ is a alkenyl group having from 2 to 4 carbon atoms or a branched alkenyl group having 6 carbon atoms.

16. The agrochemical composition according to any of claims 1 to 13, wherein in the compound of general formula (II) Ri₂ is a phenyl group.

17. The agrochemical composition according to any preceding claim, wherein the compound of general formula (II) is ivermectin, abamectin, milbemectin, moxidectin, eprinomectin, lepimectin, selamectin or doramectin.

18. The agrochemical composition according to any preceding claim, wherein the compound of general formula (I) or (II) is present as a salt.

19. The agrochemical composition according to any preceding claim, wherein iprodione is present in an amount of from 30 to 90% by weight.

20. The agrochemical composition according to any preceding claim, wherein the compound of general formula (I) or (II) is present in an amount of from 5 to 40% by weight.

21 . The agrochemical composition according to any preceding claim, comprising two or more compounds of general formula (I) and/or (II).

22. The agrochemical composition according to any preceding claim, wherein the weight ratio of iprodione to the macrolide compound of general formula (I) or (II) is from 1 :50 to 50:1 .

23. The agrochemical composition according to any preceding claim, further comprising a solvent.

24. The agrochemical composition according to any preceding claim, further comprising a surfactant.

25. The agrochemical composition according to any preceding claim, further comprising a polymeric stabiliser.

26. The agrochemical composition according to any preceding claim, wherein the composition is a water-soluble concentrate (SL), an emulstifiable concentrate (EC), an emulsion (EW), a suspension (SC, OD, FS), a water-dispersible or water-soluble granule (WG, SG), a water-dispersible or a water soluble powder (WP, SP), or a granule (GR, FG, GG, MG).

27. The use of an agrochemical composition according to any preceding claim in the control of pests at a locus.

28. A method for controlling pests at a locus, the method comprising applying to the locus a composition according to any of claims 1 to 26.

29. A method of controlling nematodes and other plant pests and pathogens at a locus, comprising applying to the locus iprodione and at least one macrolide compound selected from the compounds of general formulae (I) and (II) as defined in any of claims 1 to 18.

30. The method according to claim 29, wherein the method comprises applying to the locus a composition according to any of claims 1 to 26.

31 . An agrochemical composition substantially as hereinbefore described.

32. A method of controlling pests at a locus substantially as hereinbefore described.