GB2531098A - Novel microbiocides - Google Patents

Abstract

Benzoxaborole compounds as microbiocides Benzoxaborole compounds of formula (I) and agronomically acceptable salts, stereoisomers, diasteroisomers, enantiomers, tautomers, atropisomers and N-oxides thereof wherein R1 is a substituent as herein defined; R2 is a substituent as herein defined or is a moiety of the structure: R3 and R4 are each independently a substituent as herein defined or R3 and R4 may form together with the carbon atom to which they are attached an aliphatic 3 to 8 membered ring which can be substituted by one or more substituents R8 as herein defined; R5 and R6 are each independently a substituent as herein defined or R5 and R6 may form together with the carbon atom to which they are attached an aliphatic 3 to 8 membered ring which can be substituted by one or more substituents R7 as herein defined; W is a substiuent as herein defined; n is 0, 1, 2, 3, 4, 5 or 6 and m is 1. The use of oxaborole compounds of formula (I) in compositions and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and processes for the preparation of these compounds are also provided.

Description

Intellectual Property Office Application No. GB1508944.4 RTN4 Date:5 February 2016 The following terms are registered trade marks and should be read as such wherever they occur in this document: ACQLITY (page 35) Intellectual Property Office is an operating name of the Patent Office www.gov.uk/ipo Novel Microbiocides The present invention relates to novel microbiocidally active, in particular fungicidally active, oxaborole amino compounds their use in compositions and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants or plant propagation material, harvested food crops by phytopathogenic microorganisms, preferably fungi and to processes for the preparation of these compounds. Preferably these compounds are used in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

The incidence of serious microbial infections, particularly fungal infections, either systemic or topical, continues to increase for plants.

Fungicides are compounds, of natural or synthetic origin, which act to protect plants against damage caused by fungi. Current methods of agriculture rely heavily on the use of fungicides. In fact, some crops cannot be grown usefully without the use of fungicides. Using fungicides allows a grower to increase the yield of the crop and consequently, increase the value of the crop. Numerous fungicidal agents have been developed. However, the treatment of fungal infestations continues to be a major problem. Furthermore, fungicide resistance has become a serious problem, rendering these agents ineffective for some agricultural uses. As such, a need exists for the development of new fungicidal compounds with improved antifungal properties. It has been found that oxaborole with a specific substitution pattern are novel and have improved microbiocidal activity.

Fungicidally active oxaboroles are described in W09533754, oxaborole amides are described in W0201101 9616 and W0201 0045503 as antiprotozoal agents.

It has been found that certain novel oxaborol amino derivatives with a specific substitution pattern have advantageous microbiocidal activity.

The present invention accordingly relates to substituted oxaborol amino derivatives of formula (I) B" OH (I) wherein R1 is hydrogen, halogen, cyano, C1-C3alkyl which can be substituted by one or more substituents R3, C3-C6cycloalkyl which can be substituted by one or more substituents R5, C2-C5alkenyl which can be substituted by one or more substituents R3, C2-C5alkynyl which can be substituted by one or more substituents R8, C1-C5haloalkyl, C(O)(C1-C4)alkyl which can be substituted by one or more substituents R, C(O)O(C1-C4)alkyl which can be substituted by one or more substituents RB; R2 is hydrogen, C1-C6alkyI which can be substituted by one or more substituents R5, C3-C5cycloalkyl which can be substituted by one or more substituents R3, C1-C5haloalkyl, C2-C5alkenyl which can be substituted by one or more substituents R3, C2-C6alkynyl which can be substituted by one or more substituents R5, C(O)H, C(O)(C1-C4)alkyl which can be substituted by one or more substituents R5, C(O)phenyl which can be substituted by one or more substituents R7, C(O)O(C1-C4)alkyl which can be substituted by one or more substituents R3; or R2 is a moiety of the following structure [Wn R3 and R4 are, independently from each other hydrogen, C1-C6aIkyl which can be substituted by one or more substituents R, C1-C6haloalkyl, C2-C5alkenyl which can be substituted by one or more substituents R3, C2-C5alkynyl which can be substituted by one or more substituents R5, C3-C5cycloalkyl which can be substituted by one or more substituents R5, phenyl which can be substituted by one or more substituents R7 or R3 and R4 may form together with the carbon atom to which they are attached an aliphatic 3 to 8 membered ring which can be substituted by one or more R5 and R3 are, independently from each other hydrogen, halogen, C1-C3alkyl which can be substituted by one or more substituents R5, C1-C6haloalkyl C2-C6alkenyl which can be substituted by one or more substituents R5, C2-C5alkynyl which can be substituted by one or more substituents R5, C3-C5cycloalkyl which can be substituted by one or more substituents R3, C3-C6alkynyl which can be substituted by one or more substituents R3, phenyl which can be substituted by one or more substituents R7 or R5 and R6 may form together with the carbon atom to which they are attached an aliphatic 3 to 8 membered ring which can be substituted by one or more substituents R7; W is hydrogen, OH, SH, NH2, C1-C5alkylamino which can be substituted by one or more substituents R8, di(C1-C5alkyl)amino which can be substituted by one or more substituents R5, C1-C6alkoxy which can be substituted by one or more substituents R8, C1-C5haloalkoxy, C1-C6alkylthio which can be substituted by one or more substituents R3, OC(O)(C1-C4)alkyl which can be substituted by one or more substituents R8, OC(O)(C1-C4)haloalkyl, C1-C4aIkyI-O-N=CH-which can be substituted by one or more substituents R5, HO-NCH-, -O-NC-(C1-C4alkyl) which can be substituted by one or more substituents R6, C1-C5alkyI which can be substituted by one or more substituents R8, C1-C6haloalkyl, C2-C5alkenyl which can be substituted by one or more substituents R8, C2-C5alkynyl, C3-C5cycloalkyl which can be substituted by one or more substituents R8, mono-or bi-cyclic six-to ten-membered aryl which can be substituted by one or more substituents R7, five-to ten-memberd heteroaryl contains 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms and the heteroaryl can be substituted by one or more substituents R7; n isO, 1,2,3,4,5 or 6; misi; R7 is independently selected from the group consisting of halogen, OH, NH2, cyano, nitro, C1-C5alkyl, 01-C6haloalkyl, C1-C5alkylamino, di(C1-C5alkyl)amino, C1-C6alkoxy, 01-C6alkoxy-C1-C6alkyl, C- C6haloallcoxy, C1-C6allcoximino and C1-C5alkylendioxy, C(O)(Ci.4 alicoxy), -C(O)(C14 alicyl), -OC(O)(C1-4 alkyl), -C(O)-NH-(01.4 alkyl), -C(O)-N(C1.4 alkyl)2, -C(O)H, -C(O)OH; R8 is independently selected from -OH, ON, NH2, NO2, F, Cl, C14alkoxy, -C(O)(O14alkoxy), -OC(O)(C1-4 alkyl), -C(O)(C1-4 alkyl), -C(O)-NH-(C14 alkyl), -C(O)-N(C14 alkyl)2 and C14alkylamino; and agronomically acceptable salts, stereoisomers, diastereoisomers, enantiomers, tautomers, atropisomers and N-oxides of those compounds.

The present invention accordingly further relates to the use of benzoxaborole derivatives according to formula (I) and salts thereof for controlling or preventing infestation of plants or plant propagation material, the application of benzoxaborole derivatives according to formula (I) to useful plants, the application of benzoxaborole derivatives according to formula (I) to the locus of useful plants or the application of benzoxaborole derivatives according to formula (l)to plant propagation material of useful plants a compound of formula (I).

The present invention accordingly further relates to the use of benzoxaborole derivatives according to formula (I) and salts thereof for controlling or preventing infestation of plants or plant propagation material by treating plants or plant propagation material with an effective amount of an benzoxaborole of general formula (I).

The present invention accordingly further relates to the method of controlling phytopathogenic diseases on useful plants or plant propagation material thereof, which comprises applying to said plant or plant propagation material a fungicidally effective amount of a compound of formula (I). Preferably the method method of controlling phytopathogenic diseases on useful plants or plant propagation material thereof, which comprises applying to said plant or plant propagation material a fungicidally effective amount of a compound of formula (I), wherein plant propagation material of useful plants are seeds of useful plants.

The present invention accordingly further relates to the method for controlling or preventing infestation of plants or plant propagation material by treating plants or plant propagation material with an effective amount of an oxaborole of general formula (I).

The present invention accordingly further relates to the method of controlling phytopathogenic diseases on useful plants or plant propagation material thereof, which comprises applying to said plant propagation material a fungicidally effective amount of a compound of formula (I).

Accordingly the present invention also relates to a method of protecting plant propagation material and organs that grow at a later point in time against damage phytopathogenic diseases, which method comprises applying to said propagation material a fungicidally effective amount of a compound of formula (I).

In a further aspect of the invention, the invention provides a plant propagation material protecting composition comprising a compound of formula (I), together with a suitable carrier S therefore.

In a further aspect of the invention, the invention provides a method of controlling phytopathogenic diseases on useful plants or plant propagation material thereof, which comprises applying to said plant propagation material a fungicidally effective amount of a plant propagation material protecting composition comprising a compound of formula (I) as defined in claim 1, together with a suitable carrier therefore.

A preferred embodiment of this aspect of the invention is a plant propagation material protecting composition comprising a compound of formula (I), together with a suitable carrier therefor, wherein said plant propagation material protecting composition comprises additionally a colouring agent.

In yet a further aspect of the invention, the invention provides plant propagation material treated with a plant propagation material protecting composition comprising a compound of formula (I), together with a suitable carriertherefor.

A preferred embodiment of this aspect of the invention is plant propagation material treated with a plant propagation material protecting composition comprising a compound of formula (I), together with a suitable carrier therefor, wherein said plant propagation material protecting composition comprises additionally a colouring agent.

A method of controlling or preventing pest damage in a growing plant said method comprising applying onto the plant propagation material, before planting or sowing thereof a compound of formula (I).

A method of controlling or preventing damage by phytopathogenic diseases in a growing plant or growing plant tissue said method comprising: applying onto the plant propagation material, before planting orsowing thereof a fungicidial effective amount of a compound of formula (I).

A method of controlling or preventing fungal diseases in a growing plant or growing plant tissue said method comprising: applying onto the plant propagation material before planting or sowing thereof a fungicidial effective amount of a compound of formula (I).

In a preferred embodiment the plant propagation material is a seed or a tuber. In a further preferred embodiment the plant propagation material is a seed. In a further preferred embodiment the plant propagation material is a tuber. Preferably the seeds and tubers (stem tubers and root tubers) according to this application are alive. Preferably the seeds and tubers according to this application are able to germinate.

In a further aspect of the invention, the invention provides a method of controlling or preventing damage by phytopathogenic diseases in a growing plant said method comprising applying onto the seed, before planting or sowing thereof a compound of formula (I).

In a further aspect of the invention, the invention provides a method of controlling or preventing damage by phytopathogenic diseases in a growing plant or growing plant tissue said method comprising: applying onto the seed, before planting or sowing thereof a fungicidial effective amount of a compound of formula (I).

In a further aspect of the invention, the invention provides a method of controlling or preventing fungal diseases in a growing plant or growing plant tissue said method comprising: applying onto the seed before planting or sowing thereof a fungicidial effective amount of a compound of formula (I).

In a further aspect of the invention, the invention provides a method of protecting plant propagation material and organs that grow at a later point in time against damage by phytopathogenic diseases, which method comprises applying to said propagation material a fungicidally effective amount of a compound of formula (I).

In a further aspect of the invention, the invention provides a plant propagation material comprising compound a compound of formula (I). Preferably the plant propagation material comprising a fungicidal effective amount of a compound of formula (I).

In a further aspect of the invention, the invention provides a plant propagation material comprising compound a compound of formula (I) and comprises additionally a colouring agent.

In a further aspect of the invention, the invention provides a coated plant propagation material coated with a compound of formula (I).

In a further aspect of the invention, the invention provides a combination of a plant propagation material and a compound of formula (I).

In a further aspect of the invention, the invention provides a coated plant propagation material coated with coating comprising a compound of formula (I) as defined in claim 1.

In a further aspect of the invention, the invention provides a plant propagation material comprising an outer coating characterized that the outer coating comprises a compound according to formula (I), preferably a seed comprising an outer coating characterized that the outer coating comprises a compound according to formula (I).

In a further aspect of the invention, the invention provides a composition comprising a plant propagation material and a compound of formula (I).

In a further aspect of the invention, the invention provides a composition comprising a plant propagation material and a compound of formula and further comprising a a seed grow medium.

In a further aspect of the invention, the invention provides a plant which results from the germination of a a coated seed wherein the coating comprises a compound of formula (I).

In a further aspect of the invention, the invention provides a coated plant propagation material wherein the coating comprises a compound of formula (I).

In a further aspect of the invention, the invention provides a coated plant propagation material according to the preceding paraghraph, wherein the said material is a seed.

In a further aspect of the invention, the invention provides the combination of a plant propagation material and a composition comprising a compound of formula (I).

In a further aspect of the invention, the invention provides the combination according to the preceding parapgraph wherein the said material is a seed.

In a further aspect of the invention, the invention provides the combination according to one of the two preceding parapgraphs, further comprising a plant growth and/or seed germination S medium.

In a further aspect of the invention, the invention provides a plant which results from the germination and/or growth of the coated plant propagation material wherein the coating comprises a compound of formula (I).

In a further aspect of the invention, the invention provides a plant which results from the germination and/or growth of the coated plant propagation material wherein the coating comprises a compound of formula (I) and wherein the coated plant propagation material is a seed. Preferably the coated plant propagation material is a seed.

In a further aspect of the invention, the invention relates to the use of a compound of formula (I) according to claim 1, in the preparation of a composition for coating a plant propagation material forthe prevention or control of plant pathogenic fungi.

In a further aspect of the invention, the invention relates to a method of controlling or preventing infestation of plants or plant propagation material and/or harvested food crops susceptible to microbial attack by treating plants or plant propagation material and/or harvested food crops with an effective amount of an oxaborole of general formula (I) In a further aspect of the invention, the invention relates to a method of controlling or preventing infestation of plants or plant propagation material and/or harvested food crops susceptible to microbial attack by providing in a Frst step a agrochemical compositions according to the present invention comprising from 0.1 to 99% by weight of the compound of formula (I) and 99.9 to 1% by weight, of a solid or liquid adjuvant and/or an surfactant and in a second step applying said composition to the plants or the locus thereof The compounds of formula (I) are applied by treating plant propagation material with a fungicidally effective amount of a compound of formula (I). Preferably, compounds of formula (I) are applied by adhering compounds of formula (I) to plant propagation material in a fungicidally effective amount.

A preferred application method is seed treatment.

The method according to the invention is especially suitable to increase the yield and/or quality of useful plants, such as crop yield of crop plants.

The invention covers all agronomically acceptable salts, isomers, structural isomers, stereoisomers, diastereoisomers, enantiomers, tautomers, atropisomers and N-oxides of those compounds. The compounds of formula (I) may exist in different geometric or optical isomeric forms or in different tautomeric forms. One or more centres of chirality may be present, in which case compounds of the formula (I) may be present as pure enantiomers, mixtures of enantiomers, pure diastereomers or mixtures of diastereomers. There may be double bonds present in the molecule, such as C=C or C=N bonds, in which case compounds of formula (I) may exist as single isomers or mixtures of isomers. Centres of tautomerisation may be present. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. Also atropisomerism may occur as a result of a restricted rotation about a single bond.

S Suitable salts of the compounds of formula (I) include acid addition salts such as those with an inorganic acid such as hydrochloric, hydrobromic, sulphuric, nitric or phosphoric acid, or an organic carboxylic acid such as oxalic, tartaric, lactic, butyric, toluic, hexanoic or phthalic acid, or a sulphonic acid such as methane, benzene or toluene sulphonic acid. Other examples of organic carboxylic acids include haloacids such as trifluoroacetic acid.

N-oxides are oxidised forms of tertiary amines or oxidised forms of nitrogen containing heteroaromatic compounds. They are described in many books for example in "Heterocyclic N-oxides" by Angelo Albini and Silvio Pietra, CRC Press, Boca Raton, Florida, 1991.

Where substituents are indicated as being optionally substituted or can be substituted repectively, this means that they may or may not carry one or more identical or different substituents, e.g. one to three substituents. Normally not more than five such optional substituents are present at the same time, preferably not mor than three optional substituents are present. Where a group is indicated as being substituted, e.g. alkyl, this includes those groups that are part of other groups, e.g. the alkyl in alkylthio or alkoxy or alkylamino. The same applies forthe cycloalkyl, aryl, alkenyl, alkynyl and heteroaryl groups.

The number of substituents does not exceed the number of available C-H and N-H bonds, for example in the group C1-C6alkyl substituted by one or more R has only one to three substituents if C1alkyl thus methyl is meant.

In the context of the present specification the term "aryl" refers to a ring system which may be mono-, bi-ortricyclic. Examples of such rings include phenyl, naphthalenyl, anthracenyl, indenyl or phenanthrenyl. A preferred aryl group is phenyl.

The term "heteroaryl" refers to an aromatic ring system containing at least one heteroatom and consisting either of a single ring or of two or more fused rings. Preferably, single rings will contain up to three and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur. Examples of such groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl and tetrazolyl. A preferred heteroaryl group is pyridine.

Examples of bicyclic groups are benzothiophenyl, benzimidazolyl, benzothiadiazolyl, quinolinyl, cinnolinyl and quinoxalinyl.

The term "heterocyclyl" is defined to include heteroaryl and in addition their unsaturated or partially unsaturated analogues such as 4,5,6,7-tetrahydro-benzothiophenyl, 9H-fluorenyl, 3,4-dihydro-2H-benzo-1,4-dioxepinyl, 2,3-dihydro-benzofuranyl, piperidinyl, 1,3-dioxolanyl, 1,3-dioxanyl, 4,5-dihydro-isoxazolyl, tetrahydrofuranyl and morpholinyl.

The alkyl groups, the alkenyl groups, the alkynyl groups and the alkoxy groups in the compound of formula (I) are either linear or branched or they are perhalogenated and forming haloalkyl groups, haloalkenyl groups, haloalkynyl groups or haloalkoxy groups. Halogen signifies preferably F, Cl, Br, I, and more preferred halogen signifies F or Cl. A oxo substituent is =0, thus a oxygen atom doubly bonded to carbon or another element. The term "oxo substituent" thus embraces aldehydes, carboxylic acids, ketones, sulfonic acids, amides and esters.

S

The preferred substituents of the substituted alkyl groups, the substituted alkenyl groups, the substituted alkynyl groups, the substituted alkoxy groups, substituted aryl groups and! orthe aromatic heterocycle groups in the compound of formula (I) are selected from the following substituents F, Cl, Br, I, -OH, -CN, nitro, an oxo substituent, -C1.4alkoxy, -C14 alkylthio, C1.4alkyl, C2 4alkenyl, C24alkenyl, C24alkynyl, -C(0)H, -C(0)(C14 alkyl), -C(0)(C14alkoxy), -C(O)NH2, -C(O)NH(C14 alkyl), -C(0)N(C14 alkyl)(C14 alkyl), -OC(0)NH(C14 alkyl), -OC(O)N(C14 alkyl)(C14 alkyl),-NHC(0)(C14 alkyl),-NHC(O)(C14 alkoxy), -N(C14alkyl)C(O)(C14 alkyl), -N(C14a1ky1 )C(0)(C14 alkoxy), -OC(0) (C14 alkyl), -OC(0)(C14 alkoxy), -Si(C14 alkyl)3, -Si(C14 alkoxy)3, C10aryl, C510aryloxy, C610arylthio, C610heteroaryl, -(C13 -perhaloalkyl) , arylC25alkynyl, -C25alkenyl, heteroarylC25alkynyl, -C26alkenyl, C38cycloalkyl, -NR8R9 where R3 and R9 are independently H, - C14a1ky1 -C24alkenyl, -C24alkynyl or combine with the interjacent nitrogen to form a five-or six-membered ring which may comprise one ortwo orthree heteroatoms (one ortwo N, 0 ors atoms in addition to the interjacent nitrogen atom), in which case the heterocyclic ring is unsubstituted or the heterocyclic ring is substituted by one or two oxo substituent, C14 alkyl groups, -C24alkenyl or substituted -C24alkenyl, -C24alkynyl or substituted -C24alkynyl, -C(O)H, -C(O)(C14 alkyl), -C(O)(C14 alkoxy), -C(O)NH2, -C(O)NH(C14 alkyl), -C(O)N(C14 alkyl)(C14 alkyl), -OC(O)NH(C14 alkyl), -OC(0)N(C14 alkyl)(C14 alkyl),-NHC(O)(C14 alkyl),-NHC(0)(C14 alkoxy), -N(C14 alkyl)C(O)(C14 alkyl), -N(C14 alkyl)C(O)(C14 alkoxy), -OC(O) (C1.4 alkyl), -OC(O)(C14 alkoxy), -Si(C14 alkyl)3, -Si(C1.4 alkoxy)3, C510ary1, C510aryloxy, C310arylthio, C510heteroaryl, -(C18 -perhaloalkyl) , arylC14alkynyl, -C15alkynyl, wherein all the alkyl, alkenyl, alkynyl, alkoxy, aryl, aryloxy, arylthio or heteroaryl groups are either substituted or unsubstituted, preferably these substituents of the substituted groups bear only one further substituent, more preferably these substituents of the substituted groups are not The more preferred substituents of the substituted alkyl groups, alkenyl groups, the alkynyl groups and the alkoxy are selected from the following substituents -OH, CN, F, Cl, C14alkoxy, -C14alkoxy, -C14 alkylthio. C14a1ky1, C24alkenyl. C24alkenyl, C24alkinyl, C10aryl, -C14alkylamino. -OC(O) (C1.4 alkyl) -C(O)(C14alkoxy). The alkyl groups are branched or linear. The most preferred alkyl groups are methyl, ethyl, propyl, iso-propyl, n-butyl, t-butyl (1,i-diemthylethyl), sec-butyl (1-methylpropyl), iso-butyl (2-methylpropyl), pentyl, iso-pentyl (3-methylbutyl, isoamyl), 1-methylpentyl, 1-ethylpentyl, hexyl, heptyl, or octyl. Preferred alkenyl groups are ethenyl, propenyl (i-propenyl, 2-propenyl), butenyl (1 -butenyl, 2-butenyl, 3-butenyl, 2-methylpropen-1 -yl, 2-methylpropen-2-yl), pentenyl (pent-i - enyl, pent-2-enyl, pent-3-enyl, 2-methylbut-1-enyl. 3-methylbut-i-enyl, 2-methylbut-2-enyl, 3- methylbut-2-enyl, 2-methylbut-3-enyl, 3-methylbut-3-enyl, 1,2-dimethylprop-2-enyl, 1,i-dimethylprop- 2-enyl). Preferred alkynyl groups are ethinyl, propinyl (prop-1-inyl or prop-2-inyl (propargyl)), butyl (but-i-ynyl, but-2-ynyl, but-3-ynyl), pentinyl (pent-i -inyl, pent-2-inyl, pent-3-inyl, pent-4-yl, 3-methylbut-1-inyl, 2-methylbut-3-inyl, 1-methylbut-3-inyl). The most preferred alkyl groups and the most preferred alkoxy groups are methyl, ethyl, propyl, t-buyl, methoxy and ethoxy groups. Methyl, ethyl and methoxy groups are very particularly preferred.

Preferably the alkyl groups in the compound of formula (I) and/or the alkoxy groups in the compound of formula (I) bear not more than two further substituents, more preferably the alkyl groups in the compound of formula (I) and/or the alkoxy groups in the compound of formula (I) bear not more than one further substituent, most preferred the alkyl groups in the compound of formula (I) and/orthe iO alkoxy groups in the compound of formula (I) are not further substituted.

The aryl and hetero aryl groups are either substituted or unsubstituted 5-membered or6-membered aromatic monocyclic which may contain at least one heteroatom selected from N, S, 0 or unsubtituted or substituted 9-membered or 1 0-membered aromatic bicyclic ring system which may iS contain one or two heteroatoms selected from N, S, 0.

Preferrably the unsubtituted or substituted heteroaryl which is mono cyclic or bicyclic ring system which is five to ten membered containing at least one heteroatom selected from 0, N or S and has not more than 3 heteroatoms For examples of such groups include furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, i,3,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, i,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl and indolizinyl, preferably thiazolyl, imidazolyl, pyrrazolyl, pyridyl and pyrimidinyl The aryl groups and heteroaryl groups are preferably unsubtituted or substituted 5-membered or6-membered aromatic monocyclic ring system which may contain one or two heteroatoms selected from N or S or 0 wherein the substituents are selected from the group consisting of halogen, hydroxy, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkoxy-C1-C4alkyl,C1-C4haloalkoxy, C1-C4alkoximino and C1-C4alkylendioxygroups, phenyl, pyridyl, thiophene, imidazole or pyrrazol groupsThe aryl groups and heteroaryl groups are preferably unsubstituted or substituted 9-membered or 1 0-membered aromatic bicyclic ring system which may contain one or two heteroatoms selected from N or S or 0 wherein the substituents are selected from the group consisting of halogen, hydroxy, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkoxy- 01-C4alkyl,01-C4haloalkoxy, 01-C4alkoximino and 01-C4alkylendioxygroups, more preferably naphtyl, benzofuranyl, purinyl, indolyl, benzo[b]thiophenyl or quinolinyl groups The preferred substituents of the substituted aryl groups and heteroaryl groups in the compound of S formula (I) are selected from the group consisting of halogen, hydroxy, cyano, nitro, -C(0)(C 14 alkoxy), -C(O)(01-4 alkyl), -C(O)-NF--I-(C1-4 alkyl), -C(O)-N(C1-4 alkyl)2, C1-C4alkyl, 01-C4haloalkyl, 01-C4alkoxy, C1-C4alkylthio, C1-C4alkoxy-C1-C4alkyl,C1-C4haloalkoxy, C1-C4alkoximino, C- C4allcylendioxy, -C(O)NH(C14 alkyl), -C(O)N(C14 alky(C14 alkyl), -OC(O)NH(C14 alkyl), -OC(O)N(C14 alky(C14 alkyl),-NHC(0)(C14 alkyl),-NHC(O)(C14 alkoxy), -N(C,4 alkyl)C(O)(014 alkyl), -N(C14a1ky1)0(O)(C14 alkoxy), -00(0) (014a1ky1), more preferred substituents of the substituted aryl groups or heteroaryl groups in the compound of formula (I) are selected from the following substituents F, Cl, OF3, ON, -OH, nitro, C14 alkyl, -C14 alkoxy, -C(0)(C alkoxy), -C(0)H, -C(0)(C14 Alkyl), -wherein the alkyl groups are either The most preferred substituents of the substituted aryl groups and heteroaryl groups in the compound of formula (I) are selected from the following substituents, F, Cl, -C14a1ky1, C14alkoxy, -CN, -C(O)(C 1-4 alkoxy), -C(0)(C1-4 alkyl), -C(O)-N-(C1-4 alkyl) and preferably F, Cl are the even more preferred substituents of the substituted aryl groups in the compound of formula (I).

In particularly preferred embodiments for the methods and compounds of the present invention the preferred groups R1, R2, R3, R4, R5, R5, R7, R3 and Wand the meaning of n and m in any combination thereof, are as set out below.

Preferably R1 is hydrogen, halogen, ON, C,-C5alkyl which can be substituted by one or more substituents R5, C,-C5haloalkyl, C2-C4alkynyl which can be substituted by one or more substituents R3.

More preferably R1 is halogen, methyl, trifluoromethyl, cyano, ethynyl, even more preferably halogen, most preferably F or Cl.

Preferably R2 is hydrogen, C1-Calkyl which can be substituted by one or more substituents R5, C-C5haloalkyl, C(0)aryl which can be substituted by one or more substituents R7, C(0)C1-C4alkyl which can be substituted by one or more substituents R8. C(0)0C1-C4alkyl which can be substituted by one or R2 is a moiety of the following structure [W More preferably R2 is hydrogen, C(O)aryl which can be substituted by one or more substituents R7, C(O)C1-C4alkyl which can be substituted by one or more substituents R3 or R2 is a moiety of the following structure Even more preferred R2 is hydrogen or C(O)aryl which can be substituted by one or more substituents R7, C(O)C1-C4alkyl which can be substituted by one or more substituents R3 or R2 is a moiety of the following structure Most preferably R2 is hydrogen or R2 is a moiety of the following structure [w Preferably R3 and R4 are independently from each other hydrogen, C1-C5alkyl.

More preferably R3 and R4are both hydrogen.

Preferably R5 and R3 are independently from each other hydrogen, halogen, C1-C6alkyl which can be substituted by one or more substituents R5, C1-C6haloalkyl.

More preferably R5 and R5are independently from each other hydrogen, halogen, C1-C6alkyl which can be substituted by one or more substituents R3.

S Most preferably R5 and R5are both hydrogen.

Preferably W is hydrogen, OH, SH, C1-C6alkylamino which can be substituted by one or more substituents R8, di(C1-C6alkyl)amino which can be substituted by one or more substituents R8, C1-C6allcoxy which can be substituted by one or more substituents R8, C1-C5haloallcoxy which can be substituted by one or more substituents R3, C1-C5alkylthio which can be substituted by one or more substituents R3, C1-C5alkyl; OC(O)(C1-C4)alkyl which can be substituted by one or more substituents R3.

More preferably W is hydrogen, OH, C1-C6alkoxy which can be substituted by one or more substituents R3, C1-C5alkyl which can be substituted by one or more substituents R3; Most preferred, W is hydrogen, C1-C6alkoxy which can be substituted by one or more substituents R3; Preferably m is 1 and n isO, 1,2,3, or 4; More preferably mis 1 and n isO, 1 2, or 3; Preferably R7 is independently selected from the group consisting of halogen, OH, NH2, cyano, nitro, C1-C5alkyl, C1-C5haloalkyl; and R5 is independently selected from -OH, CN, NH2, NO2, F, Cl, C14alkoxy, -C(O)(C14alkoxy), -OC(O)(C1-4 alkyl) -C(O)(C1-4 alkyl).

More preferably R7 is independently selected from the group consisting of F, Cl; and R3 is independently selected from -OH, C14alkoxy, -C(O)(C14alkoxy).

In a preferred embodiment R1 is hydrogen, CN, C1-C5alkyl which can be substituted by one or more substituents R5, C1-C3haloalkyl which can be substituted by one or more substituents R3, C2-C4alkynyl which can be substituted by one or more substituents R5; R2 is hydrogen, C1-C6alkyl which can be substituted by one or more substituents R3, C1-C5haloloalkyl, C(O)aryl which can be substituted by one or more substituents R7, C(O)C1-C4alkyl which can be substituted by one or more substituents R8, C(O)0C1-C4alkyl which can be substituted or R2 is a moiety of the following structure [W R5 and R5 are independently from each other hydrogen, halogen, C1-C5alkyl which can be substituted by one or more substituents R3, C1-C6haloalkyl; preferably R5 and R6 are independently from each other hydrogen, halogen, C1-C5alkyl which can be substituted by one or more substituents R3; W is hydrogen, OH, SH, C1-C5alkylamino which can be substituted by one or more substituents R8, di(C1-C5alkyl)amino which can be substituted by one or more substituents R3, C1-C5alkoxy which can be substituted by one or more substituents R3, C1-C6haloalkoxy which can be substituted by one or more substituents R3, C1-C5alkylthio which can be substituted by one or more substituents R8, C1-C5alkyl which can be substituted by one or more substituents RB; m is 1 and n isO, 1, 2, 3, or 4; R7 is independently selected from the group consisting of halogen, OH, NH2, cyano, nitro, C1-C5alkyl, C1-C5haloalkyl; and R3 is independently selected from -OF-I, CN, NH2, NO2, F, Cl, C14alkoxy, -C(O)(C14alkoxy), -In a further more preferred embodiment R1 is halogen, methyl, trifluoromethyl, cyano, ethynyl, even more preferably F or Cl.

R2 is hydrogen, C(O)aryl which can be substituted by one or more substituents R7, C(O)C1-C4alkyl which can be substituted by one or more substituents R8 or R2 is a moiety of the following structure [w R5 and R5are both hydrogen; W is hydrogen, OH, C1-C6alkoxy which can be substituted by one or more substituents R3, C1-C6alky which can be substituted by one or more substituents R31; mislandnisO,1,2,or3; R7 is independently selected from the group consisting of halogen, OH, NH2, cyano, nitro, C1-C5alkyl, C1-C5haloalkyl; and R3 is independently selected from -OH, CN, NH2, NO2, F, Cl, C14alkoxy, -C(O)(C14alkoxy), -In a further even more preferred embodiment R1 is halogen, methyl, trifluoromethyl, cyano, ethynyl, even more preferably F or Cl.

R2 is hydrogen, C(O)aryl which can be substituted by one or more substituents R7, C(O)C1-C4alkyl S which can be substituted by one or more substituents R3 or C1-C6alkyl which can be substituted by R5 and R5are both hydrogen; W is hydrogen, C1-C5alIcyl which can be substituted by one or more substituents R8; m is 1 and n is 0, 1, 2, or 3; R7 is independently selected from the group consisting of halogen, OH, NH2, cyano, nitro, C1-C5alkyl, C1-C5haloalkyl; and R3 is independently selected from -OH, CN, NH2, NO2, F, Cl, C14alkoxy, -C(O)(C14alkoxy), -In a further most preferred embodiment R1 is halogen, methyl, trifluoromethyl, cyano, ethynyl, even more preferably F or Cl.

R2 is hydrogen or C(O)phenyl which can be substituted by one or more substituents R, C(O)Cr C4alkyl which can be substituted by one or more substituents R; R5 and R5are both hydrogen; W is hydrogen, C1-C5alkyl which can be substituted by one or more substituents R3; mislandnis0,1,2,or3; R7 is independently selected from the group consisting of F, Cl; and R3 is independently selected from -OH, C14alkoxy, -C(O)(C14alkoxy).

In one embodiment the compounds of compounds of formula (I) have the formula (Ila) N B' OH (Ila) Wherein R2 is hydrogen, C1-C5alkyl which can be substituted by one or more substituents R3, C(O)aryl which can be substituted by one or more substituents R7, C(O)C1-C4alkyl, C(O)OC1-C4alkyl, C3-C5cycloalkyl, C1-C6haloalkyl, C2-C6alkenyl which can be substituted by one or more substituents R3, C3-C5alkinyl which can be substituted by one or more substituents R8, C(O)H, C(O)O(C1-C4)alkyl which can be substituted by one or more substituents R8 preferably hydrogen or C1-C6alkyl which can be substituted by one or more substituents R6 and R1, R3, R4, R5, R3, R7, R5, W, n and m are as defined above.

In one embodiment the compounds of compounds of formula (I) have the formula (lIb) [ [w]4fi 2 OH Wherein R1, R3, R4, R5, R6, R7, R8, W, n and mare as defined above.

The invention further relates to a process for the preparation of a compound of formula (I) and to compounds obtainable by this process OH (I) wherein R1, R2, R3, R4, R5, R5, and Ware as defined under formula (I) comprising reacting a compound of formula (Ill) H:N (Ill), with a compound of formula (IV) (IV), in which X is Cl, Br, I, OS(O)2Me, OS(O)2-C6H4-Me; preferably Bromo.

The invention further relates to a process for the preparation of a compound of formula (I) and to S compounds obtainable by this process B' OH (I) wherein R2 is C(O)aryl, C(O)C1-C4alkyl, C(O)0C1-C4alkyl and R1, R3, R4, R5, R5, and Ware as defined under formula (I); comprising reacting a compound of formula (Ill) (Ill), with a compound of formula (VI) (VI), wherein U is aryl, C1-C4alkyl, 0C1-C4alkyl to obtain a compound of formula (V) and reacting the compound of formula (\/) with a compound of formula (IV) [wSn (IV) The compounds of the invention may be made by a variety of methods. In all compounds S shown in the schemes below R1, R2, R3, R4, R5, R5, and Wand the meaning of n and m are as defined above.

The compounds of formula (I) N'' B" (I) may be prepared by reacting a compound of formula (Ill) (Ill), wherein R1 are as defined under formula (I); with a compound of formula (IV) [wSn (IV), in which X is Cl, Br, I, OS(O)2Me, OS(O)2-C6H4-Me; preferably Bromo.

Some compounds of formula (IV) are known and commercially available.

When R2 is C(O)aryl, C(O)C1-C4alkyl, C(O)0C1-C4alkyl, the compounds of formula (I) may be prepared by reacting a compound of formula (O un wherein U is aryl, C1-C4alkyl, 0C1-C4alkyl; with a compound of formula (IV) (IV), The compounds of formula (V) may be prepared by reacting a compound of formula (Ill) H2N (Ill), wherein R1 are as defined under formula (I); with a compound of formula (VI) (VI), Wherein U is aryl, C1-C4alkyl, 0C1-C4alkyl and R* is halogen, hydroxy or °16 alkoxy, preferably chloro. Some compounds of formula (VI) are known and commercially available.

The reactions for the preparation of compounds of formula (V) are advantageously carried out in aprotic inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran ordioxane, nitriles such as acetonitrile or propionitrile, amides such as N,N-dimethylformamide, diethylformamide or N-methylpyrrolidinone.

The reaction temperatures are advantageously between -20°C and +120°C. In general, the reactions are slightly exothermic and, as a rule, they can be carried out at ambient temperature. To shorten the reaction time, or else to start the reaction, the mixture may be heated briefly to the boiling point of the reaction mixture. The reaction times can also be shortened by adding a few drops of base as reaction catalyst. Suitable bases are, in particular, tertiary amines such as trimethylamine, S triethylamine, quinuclidine, 1,4-diazabicyclo[2.2.2]octane, 1,S-diazabicyclo[4.3.0]non-S-ene or 1,5-diazabicyclo[5.4.0]undec-7-ene. However, inorganic bases such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate may also be used as bases. The bases can be used as such or else with catalytic amounts of a phase-transfer catalyst, for example a crown ether, in particular I 8-crown-6, or a tetraalkylammonium salt.

When R* is hydroxy, a coupling agent, such as benzotriazol-1-yloxytris(dimethylamino) phosphoniumhexafluorophosphate, bis-(2-oxo-3-oxazolidinyl)-phosphinic acid chloride (BOP-CI), N,N'-dicyclohexylcarbodiimide (DCC) orl,1'-carbonyl-diimidazole (CDI), may be used.

The reactions for the preparation of compounds of formula (I) are advantageously carried out in aprotic inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran ordioxane, nitriles such as acetonitrile or propionitrile, amides such as N,N-dimethylformamide, diethylformamide or N-methylpyrrolidinone.

The reaction temperatures are advantageously between -20°C and +120°C. In general, the reactions are slightly exothermic and, as a rule, they can be carried out at ambient temperature. To shorten the reaction time, or else to start the reaction, the mixture may be heated briefly to the boiling point of the reaction mixture. The reaction times can also be shortened by adding a few drops of base as reaction catalyst. Suitable bases are, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,5-diazabicyclo[5.4.0]undec-7-ene. However, inorganic bases such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate may also be used as bases. The bases can be used as such or else with catalytic amounts of a phase-transfer catalyst, for example a crown ether, in particular 1 8-crown-6, or a tetraalkylammonium salt.

The intermediates of formula (Ill) (Ill), HN B'

OH

wherein R1 is defined under formula (I), preferably wherein R1 is F (CAS Registry Number: 943311- 50-0), R1 is Cl (CAS Registry Number: 947165-43-7), are known, and described in the literature, for example in Bioorganic & Medicinal Chemistry Letters, 20(24), 731 7-7322; 2010, or Journal of Molecular Biology, 390(2), 196-207; 2009 or Bioorganic & Medicinal Chemistry Letters, 21(7), 2048- 2054; 2011.

The compounds of formula (I) of this invention are useful as plant disease control agents. The present invention therefore further comprises a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, or to the plant seed to be protected, an effective amount of a compound of the invention or a fungicidal composition containing said compound.

Compounds of formula (I) and fungicidal compositions containing them may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and/or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and/or Mucoromycete classes.

They are effective in controlling a broad spectrum of plant diseases, such as foliar pathogens of ornamental, turf, vegetable, field, cereal, and fruit crops.

These pathogens may include: Oomycetes, including Phytophthora diseases such as those caused by Phytophthora caps/cl, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora c/fr/cola, Phytophthora citrophthora and Phytoplithora erythroseptica; Pythium diseases such as those caused by Pytli/um aplianidermaturn, Pythium arrhenomanes, Pythium graminicola, Pythium irregu/are and Pythium ultimum; diseases caused by Peronosporales such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara haistedli, Pseudoperonospora cubensis, Albugo candida, Sclerophthora macrospora and Bremia Iactucae; and others such as Aphanomyces cochlioides, Labyrinthula zosterae, Peronoscierospora sorghi and.Sc/erospora graminicola.

Ascomycetes, including blotch, spot, blast or blight diseases and/or rots for example those caused by Pleosporales such as Stemphylium solani, Stagonospora tainanensis, Spiocaea oleag/nea, Setosphaeria turcica, Pyrenochaeta lycoperis/ci, Pleospora herbarum, Phoma destructiva, Phaeosphaer/a herpotr/cho/des, Phaeociyptocus gaeumann//, Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaer/a macu/ens, Henderson/a creberrima, Helminthospor/um trit/cirepentis, Setosphaer/a turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Cotynespora cassllcola, Coch/lobo/us sat/vus, B/polaris cact/vora, Ventur/a mae qua/is, Pyrenophora teres, Pyrenophora tr/t/c/-repent/s, Alternaria alternata, Alternaria brassic/cola, A/ternaria so/ani and Alternaria tomatophila, Capnodiales such as Septoria fritici, Septor/a nodorum, Septoila glycines, Cercospora arach/d/co/a, Cercospora soj/na, Cercospora zeae-maydis, Cercosporella capsellae and Cercosporella herpotr/choides, C/ado sporium carpophilum, Cladospor/um effusum, Passa/ora fulva, Cladospor/um oxysporum, Dothistroma septosporum, Isar/opsis clavispora, Mycosphaere//a fjjiensis, Mycosphaerella graminicola, Mycove/losiella koepke/i, Phaeoisario ps/s bataticola, Pseudocercospora vitis, Pseudocercosporella herpotrichoides, Ramu/aria beticola, Ramularia collo-cygni, Magnaporthales such as Gaeumannomyces graminis, Magnaporthe grisea, Pyricularia oryzae, Diaporthales such as Anisogramma anomala, Apiognornonia errabunda, Cytospora platani, Diaporthe phaseolorurn, Discula destruct/va, Gnomonia fructicola, Gre eneria uvico/a, Melanconium jugfandThurn, Phomopsis vitico/a, Sirococcus c/avigignenti-juglandacearum, Tubakia dry/na, Dicarpella spp., Valsa ceratosperma, and others such as Actinothyrium graminis, Ascochyta p15/, Asperg/iIus flavus, Aspergil/us fumigatus, Asperg/iIus nidulans, Asperisporium caricae, Blumerie/lajaap//, Cand/da spp., Capnodium ramosum, Cephaloascus spp., Cephalospor/urn gram/ne urn, Cerato cyst/s paradoxa, Chaetornium spp., 1-/ymenoscyphus pseudoalbidus, Coccidioides spp. Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestr/s, EIsThoe ampelma, Ep/coccurn nigrurn, Epiderrnophyton spp., Eutypa Jata, Geotrichurn candidurn, GibelITha cerealis, Gloeocercospora sorghi, Gloeodes pom/gena, Gfoeospor/um perennans; Gloeot/nia temufenta, Gr/phospaer/a corticola, Kabat/e//a //n/, Lepto graph/urn microsporum, Leptosphaeru//nia crass/asca, Lophoderm/um seditiosum, Marssonina gram/n/co/a, M/crodoch/um niva/e, Mon//in/a fructicola, Monographella a/bescens, Monosporascus cannonba/lus, Naernacyc/us spp., Oph/ostoma no vo-ulmi, Paracoccid/o/des bras/Jiensis, Penicil//urn expansum, Pesta/otia rhododendri, Petriell/dium spp., Pez/cula spp., Phialophora gregata, Phyllachora porn/gena, Phymatotrichum omnivora, Physa/ospora abdita, P/ectosporium tabacThum, Po/yscyta/um pustu/ans, Pseudopeziza rnedicag/nis, Pyrenopeziza bra ssicae, Ramul/spora sorghi, Rhabdoci The pseudotsugac, Rhynchosporiurn secalis, Sacroc/ad/um oryzae, Scedospor/um spp., Sch/zothyr/um pom/, Sc/erotin/a scierotiorum, Sclerotmia rn/nor; Sclerot/um spp. Typhu/a ish/kariensis, Seimatosporium mar/ae, Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phac/d/o/des, Stigm/na palm/vora, Tapes/a yailundae, Taphrina bu/lata, Th/e/viops/s basicola, Trichoseptoria fructigena, Zygophia/ajarna/censis; powdery mildew diseases for example those caused by Erysiphales such as B/urneria gramin/s, Erysiphe po/ygoni, Uncinu/a necator, Sphaerotheca fu//gena, Podosphaera /eucotr/cha, Podospaera macu/ar/s Go/ov/nomyces c/choracearum, Levei//u/a taurica, Micro sphaera diffusa, Oidio ps/s gossypii, Phy//actinia guttata and O/d/um arach/dis; molds for example those caused by Botryosphaeriales such as Dothiorella ammatica, Diplod/a seriata, Gu/gnard/a b/dwell/i, Botnjt/s cinema, Botryot/nia a/I/i, Botryotinia fabae, Fus/coccum amygda/i, Lasiod/p/odia theobrornae, Macro phorna the/co/a, Macrophornina phaseolma, Phy//osticta cucurbitacearurn; anthracnoses for example those caused by Glommerelales such as Co//etotr/ch urn g/oeosporioides, Col/etotrichum /agenar/um, Co//etotrichum gossyp//, Glornerel/a cingulata, and Co//etotrichurn graminicola; and wilts or blights for example those caused by F-lypocreales such as Acrernon/um strictum, Claviceps purpurea, Fusarium cu/morurn, Fusariurn graminearum, Fusariurn virgu/iforme, Fusarium oxysporum, Fusarium sub glutinans, Fusariurn oxysporum fsp. cubense, Ger/achia n/vale, Gibbere//a fuj/kuro/, Gibbere/la zeae, Giloc/adiurn spp., Myrothe c/urn verrucaria, Nectria ramu/ariae, Tr/choderma v/ride, Trichothe c/urn mseum, and Ven'iciI/ium theobrornae.

Basidiomycetes, including smuts for example those caused by Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Usti/ago tritici, Usti/ago zeae, rusts for example those caused by Pucciniales such as Cerotelium f/cl, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorg/ii, Puccinia hordei, Puccinia striiforrnis f.sp. Hordei, Puccinia stri/formis f.sp. Secalis, Pucciniastrum Gory/i, or Uredinales such as Cronartium ribicola, Gymnosporangiumjuniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physope//a ampe/osidis, Tranzsche/ia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmie/fus inoderma, Mycena spp., Sphace/ot/ieca re//lana, Typh u/a /sh/kariensis, Uro cyst/s agropyil, Itersonifia perp/exans, Coflic/um mv/sum, Laetisaria fuciformis, Wa/tea circinata, Rhizoctonia so/ani, Thanetephorus cucurmeris, 1 0 Entyfoma dah/iae, Entyfome//a microspora, Neovossia moliniae and Ti//etia caries.

Blastocladiomycetes, such as Physoderma maydis.

Mucoromycetes, such as Choanephora cucurbitarum.; Mucorspp.; Rhizopus arrhizus, As well as diseases caused by other species and genera closely related to those listed above.

In addition to their fungicidal activity, the compounds and compositions comprising them may also have activity against bacteria such as Erwinia amy/ovora, Erwin/a caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scab/es and other related species as well as certain protozoa.

Compounds of formula (I) may be mixed with one or more of compounds selected from those in the following chemical or functional classes:-1,2,4-thiadiazoles, 2,6-dinitroanilines, acylalanines, aliphatic nitrogenous compounds, amidines, aminopyrimidinols, anilides, anilino-pyrimidines, anthraquinones, antibiotics, aryl-phenylketones, benzamides, benzene-sulfonamides, benzimidazoles, benzothiazoles, benzothiodiazoles, benzothiophenes, benzoylpyridines, benzthiadiazoles, benzylcarbamates, butylamines, carbamates, carboxamides, carpropamids, chloronitriles, cinnamic acid amides, copper containing compounds, cyanoacetamideoximes, cyanoacrylates, cyanoimidazoles, cyanomethylene-thiazolidines, dicarbonitriles, dicarboxamides, dicarboximides, dimethylsulphamates, dinitrophenol carbonates, dinitrophenysl, dinitrophenyl crotonates, diphenyl phosphates, dithiino compounds, dithiocarbamates, dithioethers, dithiolanes, ethyl-amino-thiazole carboxamides, ethyl-phosphonates, furan carboxamides, glucopyranosyls, glucopyranoxyls, glutaronitriles, guanidines, herbicides/plant growth regulatosr, hexopyranosyl antibiotics, hydroxy(2-amino)pyrimidines, hydroxyanilides, hydroxyisoxazoles, imidazoles, imidazolinones, insecticides/plant growth regulators, isobenzofuranones, isoxazolidinyl-pyridines, isoxazolines, maleimides, mandelic acid amides, mectin derivatives, morpholines, norpholines, n-phenyl carbamates, organotin compounds, oxathiin carboxamides, oxazoles, oxazolidine-diones, phenols, phenoxy quinolines, phenyl-acetamides, phenylamides, phenylbenzamides, phenyl-oxo-ethyl-thiophenes amides, phenylpyrroles, phenylureas, phosphorothiolates, phosphorus acids, phthalamic acids, phthalimides, picolinamides, piperazines, piperidines, plant extracts, polyoxins, propionamides, pthalimides, pyrazole-4-carboxamides, pyrazolinones, pyridazinones, pyridines, pyridine carboxamides, pyridinyl-ethyl benzamides, pyrimdinamines, pyrimidines, pyrimidine-amines, pyrimidione-hydrazone, pyrrolidines, pyrrolquinoliones, quinazolinones, quinolines, quinoline derivatives, quinoline-7-carboxylic acids, quinoxalines, spiroketalamines, strobilurins, sulfamoyl triazoles, suiphamides, tetrazolyloximes, thiadiazines, thiadiazole carboxamides, thiazole carboxanides, thiocyanates, thiophene carboxamides, toluamides, triazines, triazobenthiazoles, triazoles, triazole-thiones, triazolo-pyrimidylamine, valinamide carbamates, ammonium methyl phosphonates, arsenic-containing compounds, benyimidazolylcarbamates, carbonitriles, S carboxanilides, carboximidamides, carboxylic phenylamides, diphenyl pyridines, furanilides, hydrazine carboxamides, imidazoline acetates, isophthalates, isoxazolones, mercury salts, organomercury compounds, organophosphates, oxazolidinediones, pentylsulfonyl benzenes, phenyl benzamides, phosphonothionates, phosphorothioates, pyridyl carboxamides, pyridyl furturyl ethers, pyridyl methyl ethers, SDHIs, thiadiazinanethiones, thiazolidines.

Particularly preferred fungicidal combinations include the following where "I" designates compounds of formula (I): I + (.+/-.)-cis-1 -(4-chlorophenyl)-2-(1 H-i,2,4-triazol-1 -yl)-cycloheptanol (huanjunzuo), I + (2RS)-2-bromo-2-(bromomethyl)glutaronitrile (bromothalonil), I + (E)-N-methyl-2- [2-(2, 5-dimethylphenoxymethyl) phenyl]-2-methoxy-iminoacetamide, (mandestrobin), I + 1-(5- bromo-2-pyridyl)-2-(2,4-difiuorophenyl)-i,1-difluoro-3-(1,2, 4-triazol-i-yl)propan-2-ol, I + 1- methylcyclopropene, I + 2-methyl-, [4-methoxy-2-[[(3S,7R,BR,9S)-9-methyl-8-(2-methyl-1 -oxopropoxy)-2,6-dioxo-7-(phenylmethyl)-i,5-dioxonan-3-yl]amino]carbonyl] -3-pyridinyl]oxy]propanoic acid methyl ester, I + 2-(i-tert-butyl)-i-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-oI (TCDP), I + 2,4-D, I + 2,4-DB, I + 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, I + 2,6-dimethyl- [i,4]dithiino[2,3-c:5,6-c']dipyrrole-l,3,5,7(2H,6H)-tetraone, I + 2-[(i R,5S)-5-[(4-fluorophenyl)methyl]- 1 -hydroxy-2,2-dimethyl-cyclopentyl]methyl]-4H-1,2,4-triazole-3-thione I + 2-[3-(2-chlorophenyl)-2- (2,4-difluorophenyl)oxiran-2-yI]methyl]-4H-1,2,4-triazole-3-thione I + ametoctradin (imidium), I + 2-[2- [(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol I + 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol I + cyflufenamid, I + 2-benzyl-4-chlorophenol (Chlorophene), I + 3-(difluoromethyl)-N-(7-fluoro-i,1,3,3-tetramethyl-indan-4-yI)-1 -methyl-pyrazole- 4-carboxamide I + diclocymet, I + 3-(difiuoromethyl)-N-methoxy-1 -methyl-N-[1 -methyl-2-(2,4,6- trichlorophenyl)ethyl]pyrazole-4-carboxamide, I + 3'-chloro-2-methoxy-N-[(3RS)-tetrahydro-2-oxofuran-3-yl]acet-2', 6'-xylidide (clozylacon), I + 3-iodo-2-propinyl n-butylcarbamate (IPBC), I + 4,4,5-trifluoro-3,3-dimethyl-1 -(3-quinolyl)isoquinoline I + 4,4-difluoro-3,3-dimethyl-1 -(3- quinolyl)isoquinoline I + 5-fluoro-3,3,4,4-tetramethyl-1-(3-quinolyl)isoquinoline I + 9-fluoro-2,2- dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine I + tebufloquin, I + 4-CPA, I + 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine I + ferimzone, I + acibenzolar, I + acibenzolar-S-methyl, I + allyl alcohol, I + ametoctradin, I + amisulbrom, I + anilazine, I + aureofungin, I + azaconazole, I + azafenidin, I + azithiram, I + azoxystrobin, I + benalaxyl, I + benalaxyl-M, I + benalaxyl-M (kiralaxyl), I + benomyl, I + benthiavalicarb, I + benthiazole (TCMTB), I + benzalkonium chloride, I + benzamorf, I + benzovindiflupyr (solatenol), I + bethoxazin, I + biphenyl, I + bitertanol (biloxazol), I + bixafen, I + BLAD, I + blasticidin-S, I + Bordeaux mixture, I + boscalid, I + bromuconazole, I + bupirimate, I + but-3-ynyl N-[6-[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl] -2-pyridyl]carbamate I + dazomet, I + butylamine, I + calcium polysulfide, I + captafol, I + captan, I + carbaryl, I + carbendazim, I + carbendazim chlorhydrate, I + carboxin, I + CAS 517875-34-2 (DAS777), I + chinomethionate, I + chinomethionate (oxythioquinox, quinoxymethionate), I + chitosan, I ÷ chiobenthiazone, I + chiorfenazole, I + chiormequat, I + chioroneb, I + chioropicrin, I + chiorothalonil, I + chiozolinate, I + climbazole, I + clofencet, I + copper acetate, I + copper carbonate, I + copper hydroxide, I + copper naphthenate, I + copper oleate, I + copper oxychioride, I + copper oxyquinolate, I + coppersilicate, I + coppersuiphate, I + coppertallate, I + S coumoxystrobin, I + cresol, I + cuprous oxide, I + cyazofamid, I + cyclafuramid, I + cymoxanil, I + cyproconazole, I + cyprodinil, I + daracide, I + dichiofluanid, I + dichiorophen (dichiorophene), I + dichiorprop, I + diclomezine, I + dicloran, I + diethofencarb, I + difenoconazole, I + difenzoquat, I + diflumetorim, I + dimetachione (dimethaclone), I + dimetconazole, I + dimethipin, I + dimethirimol, I + dimethomorph, I + dimoxystrobin, I + dingjunezuo (Jun Si Qi), I + diniconazole, I + diniconazole-M, I + , I + dinobuton, I + dinocap, I + dinocton, I + dinopenton, I + diphenylamine, I + dipyrithione, I ÷ ditalimfos, I ÷ dithianon, I + dithioether, I + dodemorph, I ÷ dodicin, I + dodine, I + doguadine, I + drazoxolon, I + edifenphos, I + endothal, I + enestroburin, enoxastrobin I + fenamistrobin, I + epoxiconazole, I + etaconazole, I + etem, I + ethaboxam, I + ethephon, I + ethoxyquin, I + famoxadone, I + fenamidone, I + fenarimol, I + fenbuconazole, I + fenfuram, I + fenhexamid, I + fenoxanil, I + fenpiclonil, I + fenpropidin, I + fenpropimorph, I ÷ fenpyrazamine, I + fentin acetate, I + fentin hydroxide, I + ferbam, I + fluazinam, I + fludioxonil, I + flufenoxystrobin, I + flumetralin, I + flumorph, I + fluopicolide, I + fluopicolide (flupicolide), I + fluopyram, I + fluoroimide, I + fluoxastrobin, I + fluquinconazole, I + flusilazole, I + flusulfamide, I + flutianil, I + flutolanil, I + flutriafol, I + fluxapyroxad, I + folpet, I + forchiorfenuron, I + fosetyl, I + fuberidazole, I + furalaxyl, I + furametpyr, I + gibberellic acid, I ÷ gibberellins, I + guazatine, I + hexachlorobenzene, I + hexaconazole, I + hymexazol, I + hymexazole, hydroxyisoxazole I + imazalil, I + I + etridiazole, I + imazalil, I + imazalil sulphate, I + imibenconazole, I + iminoctadine, I + iminoctadine triacetate, I + iodocarb (isopropanyl butylcarbamate), I + ipconazole, I + iprobenfos, I + iprodione, I + iprovalicarb, I + isofetamid, I + isopropanyl butylcarbamate (iodocarb), I + isoprothiolane, I + isopyrazam, I ÷ isotianil, I ÷ kasugamycin, I ÷ kresoxim-methyl, I + KSF-1002, I + maleic hydrazide, I + mancozeb, I + mandestrobin, I + mandipropamid, I + maneb, I + mepanipyrim, I + mepiquat, I + mepronil, I + meptyldinocap, I + metalaxyl, I + metalaxyl-M (mefenoxam), I + metam, I + metaminostrobin, I + metconazole, I + methyl bromide, I + methyl iodide, I + methyl isothiocyanate, I + metiram (polyram), I + metiram-zinc, I + metominostrobin, I + metrafenone, I + m-phenylphenol, I + myclobutanil, I + N'-(2,5-Dimethyl-4- phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, I + N'-[4-(4,5-Dichloro-thiazol-2-yloxy)-2,5-dimethyl- phenyl]-N-ethyl-N-methyl-formamidine, I + N'-[4-[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5- yljoxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, I + ethirimol, I + N-(2-p- chlorobenzoylethyl)-hexaminium chloride, I + N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl- 3-(difluoromethyl)-5-fluoro-1 -methyl-pyrazole-4-carboxamide I + N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1 -methyl-pyrazole-4-carboxamide I + carpropamid, I + nabam, I + naphthalene acetamide, I + NNF-0721, I + ocihilinone, I + ofurace, I + orysastrobin, I + osthol, I + oxadixyl, I + oxasulfuron, I + oxathiapiprolin, I + oxine-copper, I + oxolinic acid, I + oxpoconazole, I + oxycarboxin, I + paclobutrazol, I + pefurazoate, I + penconazole, I + pencycuron, I + penflufen, I + penthiopyrad, I + phenamacril, I + phosdiphen, I + phosetyl-Al, I + phosetyl-Al (fosetyl-al), I + phosphorus acids, I + phthalide (fthalide), I + picarbutrazox, I + picoxystrobin, I + piperalin, I + polycarbamate, I + polyoxin D (polyoxrim), I + p-phenylphenol, I + probenazole, I + prochloraz, I + procymidone, I + prohexadione, I + prohexadione-calcium, I + propamidine, I + propamocarb, I + propiconazole, I + propineb, I + propionic acid, I + proquinazid, S I + prothioconazole, I + pyraclostrobin, I + pyrametostrobin, I + pyraoxystrobin, I + pyrazophos, I + pyribencarb (KIF-7767), I + pyrifenox, I + pyrimethanil, I + pyriofenone (IKF-309), I + pyroquilon, I + quinoxyfen, I + quintozene, I + sedaxane, I + silthiofam, I + simeconazole, I + spiroxamine, I + streptomycin, I + sulphur, I + tebuconazole, I + tebutioquin, I + teclottalam, I + tecnazene, (TCNB), I + tetraconazole, I + thiabendazole, I + thicyofen, I + thidiazuron, I + thifluzamide, I + thiophanate-methyl, I + thiram, I + tiadinil, I + tioxymid, I + tolciofos-methyl, I + tolprocarb, I + tolyifluanid, I ÷ triadimefon, I + triadimenol, I + triazoxide, I + tribromophenol (TBP), I ÷ tribufos (tributyl phosphorotrithioate), I + triclopyricarb, I + tricyclazole, I + tridemorph, I + trifloxystrobin, I + triflumizole, I + triforine, I + trinexapac, I + triticonazole, I + uniconazole, I + validamycin, I + valifenalate, I + vapam, I + vapam (metam sodium), I + vinclozolin, I + zineb, I + ziram, I + zoxamide, I + cz-naphthalene acetic acid.

Compounds of this invention can also be mixed with one or more further pesticides including insecticides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.

Examples of such agricultural protectants with which compounds of this invention can be formulated are: Insecticides such as abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, buprofezin, carbofuran, cartap, chlorantraniliprole (DPX-E2Y45), chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate, flufenerim (UR-50701), flufenoxuron, fonophos, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde. methamidophos, methidathion, methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, novifiumuron (XDE-007), oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, pymetrozine, pyrafluprole, pyrethrin, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen (BSN 2060), spirotetramat, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, trichlorfon and triflumuron; Bactericides such as streptomycin; Acaricides such as amitraz, chinomethionat, chlorobenzilate, cyenopyrafen, cyhexatin, dicofol, dienochior, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and Biological agents such as Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, S baculovirus, and entomopathogenic bacteria, virus and fungi.

Plant disease control is ordinarily accomplished by applying an effective amount of a compound of this invention either pre-or post-infection, to the portion of the plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing. The compounds may also be applied to seeds to protect the seeds and seedlings developing from the seeds. The compounds may also be applied through irrigation water to treat plants.

The present invention envisages application of the compounds of the invention to plant propagation material prior to, during, or after planting, or any combination of these.

Methods for applying or treating active ingredients on to plant propagation material are known in the art and include dressing, coating, pelleting and soaking application methods. Conventional treating techniques and machines can be used, such as fluidized beds, roller mills, rotostatic seed treaters, drum coaters, and spouted beds. Also, using commercially available equipment (Van der Ende PHYTO-DRIP BV, NL) it is possible to perform a precise seed soaking application at the time of planting.

Methods of applying to the soil can be via any suitable method which ensures that the compound of formula (I) or compositions comprising the compound of formula (I) penetrates the soil, for example, nursery tray application, in furrow application, soil drenching, soil injection, drip irrigation, application through sprinklers or central pivot, or incorporation into soil (broad cast or in band). Alternatively or in addition one or more materials may be applied on a suitable substrate, for example a seed which is not intended for germination but which is sown together with the plant propagation material.

Even distribution of ingredients and good adherence are particularly desirable. Treatment can vary from a thin film or dressing of a formulation, for example, a mixture of active ingredients and adjuvants, on a plant propagation material, such as a seed, where the original size and shape are recognisable, to an intermediary state and through to a thicker film such as pelleting with many layers of potentially different materials where the original shape andlor size of the seed is no longer recognisable.

Generally for soil treatments, application rates can vary from 0.05 to 3 kg per hectare (g/ha) of active ingredient(s). Generally for seed treatments, application rates can vary from 0.5 to 1 000g of active ingredient(s) /100kg of seeds.

Examples of seed treatment formulation types for pre-mix compositions include: WS: wettable powders for seed treatment slurry LS: solution for seed treatment ES: emulsions for seed treatment FS: suspension concentrate for seed treatment WG: water dispersible granules, and CS: aqueous capsule suspension.

S Although active ingredients can be applied to plant propagation material in any physiological state, a common approach is to use seeds in a sufficiently durable state to incurr no damage during the treatment process. Typically, seed would have been harvested from the field; removed from the plant; and separated from any cob, stalk, outer husk, and surrounding pulp or other non-seed plant material. Seed would preferably also be biologically stable to the extent that treatment would not cause biological damage to the seed. It is believed that treatment can be applied to seed at any time between seed harvest and sowing of seed including during the sowing process.

Methods for applying or treating active ingredients on to plant propagation material orto the locus of planting are known in the art and include dressing, coating, pelleting and soaking as well as nursery tray application, in furrow application, soil drenching, soil injection, drip irrigation, application through sprinklers or central pivot, or incorporation into soil (broad cast or in band).

Altematively or in addition active ingredients may be applied on a suitable substrate sown together with the plant propagation material.

Rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions. Foliage can normally be protected when treated at a rate of from less than about 1 g/ha to about 5,000 g/ha of active ingredient. Seed and seedlings can normally be protected when seed is treated at a rate of from about 0.1 to about lOg per kilogram of seed.

Crops of useful plants in which the composition according to the invention can be used include perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for

example grapes.

Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).

Crops are to be understood as also including those crops which have been rendered tolerant to herbicides like bromoxynil or classes of herbicides such as ALS-, EPSPS-, GS-, HPPD-and FF0-inhibitors. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer canola. Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate-and glutosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

Crops are also to be understood as being those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include 6-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.

An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds). An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification). For example, a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

The compounds according to the invention can be used as pesticidal agents in unmodified form, but they are generally formulated into compositions in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances. The formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil-fiowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can either be used directly or diluted prior to use. The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.

The formulations can be prepared e.g. by mixing the active ingredient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof The active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 S to 95% by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.

The formulation adjuvants that are suitable for the preparation of the compositions according to the invention are known per Se. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1 -trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octa-decanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone and the like.

Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.

A large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use.

Surface-active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide S addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sultosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono-and di-alkylphosphate esters; and also further substances described e.g. in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981).

Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.

The compositions according to the invention can include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10%, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise mineral oils oran oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of C5-C22 fatty acids, especially the methyl derivatives of C12-C13 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 101h Edition, Southern Illinois University, 2010.

The inventive compositions generally comprise from 0.1 to 99% by weight, especially from 0.1 to 95 % by weight, of compounds of the present invention and from ito 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance. Whereas commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.

The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline compounds may be applied at a rate of from ito 2000 I/ha, especially from 10 to 1000 I/ha.

Preferred formulations can have the following compositions (weight %): Emulsifiable concentrates: active ingredient: ito 95 %, preferably 60 to 90 % surface-active agent: ito 30 %, preferably 5 to 20 % liquid carrier: ito 80 %, preferably ito 35 % S Dusts: active ingredient: 0.i to 10%, preferably 0.i to 5% solid carrier: 99.9 to 90 %, preferably 99.9 to 99 % Suspension concentrates: active ingredient: 5 to 75%, preferably 10 to 50% water: 94 to 24%, preferably 88 to 30% surface-active agent: ito 40 %, preferably 2 to 30 %

Wettable powders:

active ingredient: 0.5 to 90 %, preferably ito 80 % surface-active agent: 0.5 to 20%, preferably ito 15% iS solid carrier: 5 to 95%, preferably iS to 90% Granules: active ingredient: 0.i to 30%, preferably 0.i to is % solid carrier: 99.5 to 70 %, preferably 97 to 85 % The following Examples further illustrate, but do not limit, the invention.

Wettable powders a) b) c) active ingredients 25% 50 % 75 % sodium lignosulfonate 5 % 5 % -sodium lauryl sulfate 3 % -5% sodium dUsobutylnaphthalenesulfonate -6% iO % phenol polyethylene glycol ether -2 % - (7-8 mol of ethylene oxide) highly dispersed silicic acid 5% 10% iO % Kaolin 62% 27% -The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

Powders for dry seed treatment a) b) c) active ingredients 25% 50 % 75 % light mineral oil 5% 5% 5% highly dispersed silicic acid 5 % 5 % - Kaolin 65% 40% -Talcum I 201 The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

Emulsifiable concentrate active ingredients 10% octylphenol polyethylene glycol ether 3 % (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 % Cyclohexanone 30 % xylene mixture 50 % Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

Dusts a) b) c) Active ingredients 5 % 6 % 4 % Talcum 95% -- Kaolin -94 % -mineral filler --96 % Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

Extruder granules Active ingredients 15% sodium lignosulfonate 2 % carboxymethylcellulose 1 % Kaolin 82% The combination is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

Coated granules Active ingredients 8 % polyethylene glycol (mol. wt. 200) 3 % Kaolin 89% The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

Suspension concentrate active ingredients 40 % propylene glycol 10% nonyiphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 % Sodium lignosulfonate 10% carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 % Water 32 % The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.

Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

S

Flowable concentrate for seed treatment active ingredients 40 % propylene glycol 5 % copolymer butanol P0/EQ 2 % Tristyrenephenole with 10-20 moles EQ 2% 1,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium salt 5 % Silicone oil (in the form of a 75% emulsion in water) 0.2 % Water 45.3 % The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.

Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

Slow Release CaDsule Susrension 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene dUsocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

The Examples which follow serve to illustrate the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.8 ppm.

Preparation examples: The following examples describe the synthesis of compounds of formula (I) and intermediates thereof.

General procedure for alkylation of either lila or Ilib H2N OH lila OH Ilib To a solution of benzoxaborol-6-amine lila or IlIb in DMF (1M) at 0°C were successively added 2.0 equivalents of potassium carbonate and 1.0 equivalent of alkylating agent (propargyl bromide derivatives). The reaction mixture was stirred for lhr at 5°C then for l7hrs at RT and then poured onto a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted thrice with ethyl acetate. The organic layers were combined, washed once with water then with brine and dried over sodium sulfate. After filtration and concentration under reduced pressure, the crude was purified by chromatography (hexane/ethyl acetate) to give a mixture of a mono-alkylated and di-alkylated compounds. These two compounds were further separated by reversed phase chromatography (acetonitrile/water + 0.1% formic acid).

General procedure for acylation of either lila or IlIb To a solution of benzoxaborol-6-amine lila or Ilib in fl-IF at 10°C were added successively the acid chloride (1.05 eq.) and triethylamine (2.0 eq). The reaction mixture was stirred at 23°C for 4h. The reaction mixture was poured onto H20 and then acidified with 1M HCI until pH=3. The mixture was stirred at 45°C for 30mm and at RT for lh. The precipitate was filtered off, washed twice with water and once with cyclohexane/diethylether (111). The crude N-acylated benzoxaborol-6-amine Va orVb were dried in an oven under reduced pressure at 55°C for lh.

General procedure for alkylation of either Va or Vb

CI

U)1'NA) B U)LNc)B H bHv H OHVb To a solution of N-acylated benzoxaborol-6-amine Va or Vb in THF at 0°C were added 2.2 equivalents of sodium hydride (55 mass%). The reaction mixture was stirred at RT for lh and then, cooled down to 5°C prior to the addition of 1.0 equivalent of alkylating agent (propargyl bromide derivatives). The reaction mixture was further stirred at 5°C for 2hr then at RT for 1 8hrs. A saturated ammonium chloride aqueous solution was carefully added to the reaction mixture which was extracted thrice with ethyl acetate. The organic layers were combined, washed once with water then with brine and dried over sodium sulfate. After filtration and concentration under reduced pressure, the crude was purified by reversed phase chromatography (acetonitrile/water + 0.1% formic acid).

Throughout the description that follows, temperatures are given in degrees Celsius; "NMR" means S nuclear magnetic resonance spectrum; MS stands for mass spectrum; "%" is per cent by weight, unless corresponding concentrations are indicated in other units. The following abbreviations are

used throughout this description:

m.p. = melting point S = singlet br = broad d = doublet dd = doublet of doublets = triplet q = quartet m = Multiplet ppm = parts per million U PLC: ACQUITY SOD Mass Spectrometer from Waters (Single quadrupole mass spectrometer) lonisation method: Electrospray Polarity: positive ions Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 400, Cone Gas Flow (LJHr) 60, Desolvation Gas Flow (LJHr) 700 Mass range: 100 to 800 Da DAD Wavelength range (nm): 210 to 400 Method Waters ACQUITY UFLC with the following HPLC gradient conditions (Solvent A: Water/Methanol 9:1,0.1% formic acid and Solvent B: Acetonitrile,0. 1% formic acid) Time (minutes) A (%) B (%) Flow rate (mI/mm) 0 100 0 0.75 2.5 0 100 0.75 2.8 0 100 0.75 3.0 100 0 0.75 Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60°C.

Example P1: 4-[(S-chloro-1 -hydroxy-3H-2,1 -benzoxaborol-6-yl)amino]but-2-yn-1 -ol j OH

W

jpj288-291°C Example P2: 4-[(5-fluoro-1 -hydroxy-3H-2,1 -benzoxaborol-6-yI)amino]bul-2-yn-1 -ol

HQ

J OH

H

mp: 246-251°C Example P3: 5-chloro-1 -hydroxy-N-(4-methoxybut-2-ynyl)-3H-2,1 -benzoxaborol-6-amine :cc,o

J OH

mp: 103-105°C Example P4: 4-[(5-chloro-1 -hydroxy-3H-2,1 -benzoxaborol-6-yamino]but-2-ynyl acetate mp: 139-141°C Example PS: 5-fluoro-N,N-bis(hex-2-ynyl)-1 -hydroxy-3H-2,1 -benzoxaborol-6-amine

OH

1H NMR (Acetone) 3 ppm: 8.08 (1H, s bO; 7.54(1H, d); 7.14 (1H, d); 4.08 (2H, s); 4.0 (4H, 0; 2.17- 2.00 (4H. m); 1.50-1.4 (4H, m); 0.92 (6H, t).

Example P6: 4-[(5-fluoro-1 -hydroxy-3H-2,1 -benzoxaborol-6-yI)amino]but-2-ynyl acetate

HQ

mp:94-98°C Example PT: 5-fluoro-1 -hydroxy-N-(4-methoxybut-2-ynyl)-3H-2,1 -benzoxaborol-6-amine

J OH

mp: 105-107°C Example PB: 5-fluoro-N-hex-2-ynyl-1 -hydroxy-3H-2,1 -benzoxaborol-6-amine

HQC

J OH

mp: 120-122°C Example P9: 5-chloro-N-hex-2-ynyl-1 -hydroxy-3H-2,1 -benzoxaborol-6-amirie mp: 98-100°C Example P10: S-chloro-1 -hydroxy-N-prop-2-ynyl-3H-2,1 -benzoxaborol-6-amine H2 mp: 84-88°C

S

Example P11: 5-fluoro-1 -hydroxy-N,N-bis(pent-2-ynyl)-3H-2,1 -benzoxaborol-6-amine mp: 132-134°C Example P12: S-chloro-1 -hydroxy-N,N-bis(pent-2-ynyl)-3H-2,1 -benzoxaborol-6-amine 1H NMR (Acetone) 3 ppm: 8.16 (1H, S br); 7.54 (1H, s); 7.49 (1H, s); 5.00 (2H, s); 3.98 (4H, t); 2.21- 2.13 (4H, m); 1.09 (6H, t).

Example P13: S-fluoro-1 -hydroxy-N-pent-2-ynyl-3H-2,1-benzoxaborol-6-amine

F

mp: 132-134°C Example P14: 5-chloro-1 -hydioxy-N-pent-2-ynyl-3F-l-2,1 -benzoxaborol-6-amine I 0

H B

mp: 135-137°C Example P15: 5-fluoro-1 -hydroxy-N-prop-2-ynyl-3H-2,1 -benzoxaborol-6-amine mp:1 37-1 39°C Example P16: N,N-bis(but-2-ynyl)-5-chloro-l -hydroxy-3H-2,1 -benzoxaborol-6-amine

I C

B j bH

mp: 44-47°C Example P17: N-but-2-ynyl-5-chloro-1 -hydroxy-3H-2,1 -benzoxaborol-6-amine I 0

H -B J bH

mp: 131-134°C Example P18: N,N-bis(but-2-ynyl)-5-fiuoro-1 -hydroxy-3H-2,1 -benzoxaborol-6-amine

F

UPLC: observed mass: 253.33; retention time: 1.35 mm.

Example P19: N-but-2-ynyl-5-fluoro-1 -hydroxy-3H-2,1 -benzoxaborol-6-amine

F

mp: 143-147°C Example P20: N,N-bis(but-2-ynyl)-1 -hydroxy-3H-2,1 -benzoxaborol-6-amine UPLC: observed mass: 271.34; retention time: 1.41 mm.

Example P21: N-But-2-ynyl-N-(5-chloro-1-hydro'-1,3-dihydro-benzo[c][1,2]oxaborol-6-y-2, 6-d ifi U 0 ro-be nzam ide

DH

mp: 142-152°C Example P22: N-(5-Chloro-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2, 6-difluoro-N-pent-2-ynyl-benzamide )cC

F JH

mp: 170-180°C The following Tables ito 72 further illustrates the invention wherein each of the Tables ito 48 discloses 21 specific compounds according to the invention and each of the Tables 49 to 72 discloses 14 specific compounds according to the invention.

(El) ; -(F2) --2 Tab Compounds Formula R1, R2 are as defined in Table R3 R4 Q 1 OltoO2i (Fl) Ti H H H 2 1.ltol.21 (Fl) TI OH3 H H 3 2.lto2.21 (Fl) Ti H CF-I3 H 4 3.lto3.21 (Fl) Ti OH3 CH3 H S 4.lto4.2l (Fl) Ti H H CH3 6 5.ltoS.21 (Fl) TI OH3 H OH3 7 6.lto6.21 (Fl) Ti H CH3 OH3 8 7.1 to 7.21 (Fl) Ti CH3 CH3 CH3 9 8.ltoB.21 (Fl) Ti H H CH3CH2 9.1 to 9.21 (Fl) Ti CH3 H CH3CH2 ii lO.ltolO.21 (Fl) Ti H CH3 CH3CH2 12 li.ltoli.21 (Fl) Ti CH3 CH3 CH3CH2 13 12.ltol2.2i (Fl) Ti H H CF3 14 13.ltol3.21 (Fl) Ti CH3 H CF3 14.ltol4.21 (Fl) Ti H CH3 CF3 16 15.ltol5.21 (Fl) Ti CH3 CH3 CF3 17 16.ltol6.21 (Fl) Ti H H CF3CH2 18 17.ltol7.21 (Fl) Ti CH3 H CF3CH2 19 18.ltol8.21 (Fl) Ti H CF-I3 CF3CF-12 19.1 to 19.21 (Fl) Ti CH3 CH3 CF3CH2 2i 20.1 to 20.21 (Fl) Ti H H CF3CH2CH2 22 2i.lto2i.21 (Fl) Ti CH3 H CF3CF-I2CF-12 23 22.1 to 22.21 (Fl) Ti H CH3 CF3CH2CH2 24 23.1 to 23.21 (Fl) TI OH3 OH3 CF3CH2CH2 24.1 to 24.21 (Fl) Ti H H CH3CH2OCH2 26 25.1 to 25.21 (Fl) Ti CH3 H CH3CH2OCH2 27 26.1 to 26.21 (Fl) Ti H CH3 CH3CH2OCH2 28 27.1 to 27.21 (Fl) TI OH3 CH3 CH3CH2OCH2 29 28.1 to 28.21 (Fl) Ti H H (CHO2CH 29.1 to 29.21 (Fl) Ti CH3 H (CH3)2CH 3i 30.1 to 30.21 (Fl) Ti H CH3 (CH3)2CH 32 31.1 to 31.21 (Fl) Ti OH3 CH3 (CH3)2CH 33 32.1to32.21 (Fl) Ti H H HOCH2 34 33.1 to 33.21 (Fl) Ti CH3 H HOCH2 34.1 to 34.21 (Fl) TI H CH3 HOCH2 36 35.1 to 35.21 (Fl) Ti OH3 CH3 HOOH2 37 36.1 to 36.21 (Fl) Ti H H CH3OCH2 38 37.1 to 37.21 (Fl) TI CH3 H CH3OCH2 39 38.1 to 38.21 (Fl) Ti H CH3 CH3OCH2 39.1 to 39.21 (Fl) Ti CH3 CH3 CH3OCH2 4i 40.1 to 40.21 (Fl) Ti H H cyclopropyl 42 41.1 to 41.21 (Fl) Ti CH3 H cyclopropyl 43 42.1 to 42.21 (Fl) TI H CH3 cyclopropyl 44 43.1 to 43.21 (Fl) Ti CH3 CH3 cyclopropyl 44.1 to 44.21 (Fl) Ti H H CH3C(O)OCH2 46 45.1 to 45.21 (Fl) Ti CH3 H CH3C(O)OCH2 47 46.1 to 46.21 (Fl) Ti H CH3 CH3C(O)OCH2 48 47.1 to 47.21 (Fl) TI CH3 CH3 CH3C(O)OCH2

Table TI _______

____ R1 R2

I H H 2 F H

3 CI H 4 CH3 H CF3 H 6 ON H 7 ethynyl H 8 H CH3 9 F CH3 CI CH3 11 CH CH3 12 CF3 CF-I3 13 CN CH3 14 ethynyl CH3 H CH3CH2 16 F CH3CH2 17 CI CH3CH2 18 CH3 CH3CH2 19 CF3 CH3CH2 CN CH3CH2 21 ethynyl CH3CH2 Table Compounds Formula R1, R3 are as defined in Table R4 Q *H4YH 48.1 to 48.14 (F2) T2 H H 49.1 to 49.14 (F2) T2 CH3 H 51 50.1 to 50.14 (F2) T2 H CH3 52 51.ltoSl.14 (F2) T2 CH3 CH3 53 52.1 to 52.14 (F2) T2 H CH3CH2 54 53.1 to 53.14 (F2) T2 CH3 CH3CH2 54.1 to 54.14 (F2) T2 H CF3 56 55.1 to 55.14 (F2) T2 CH3 CF3 57 56.1 to 56.14 (F2) T2 H CF3CH2 58 57.1 to 57.14 (F2) T2 CH3 CF3CH2 59 58.1 to 58.14 (F2) T2 H CF3CH2CH2 59.1 to 59.14 (F2) T2 CH3 CF3CH2CH2 61 60.1 to 60.14 (F2) T2 H CH3CH2OCH2 62 61.1 to 61.14 (F2) T2 CH3 CH3CH2OCH2 63 62.1 to 62.14 (F2) T2 H (CH3)2CH 64 63.1 to 63.14 (F2) T2 CH3 (CH3)2CH 64.1 to 64.14 (F2) T2 H HOCH2 66 65.1 to 65.14 (F2) T2 CH3 HOCH2 67 66.1 to 66.14 (F2) T2 H CH3OCH2 68 67.1 to 67.14 (F2) T2 CH3 CH3OCH2 69 68.1 to 68.14 (F2) T2 H cyclopropyl 69.1 to 69.14 (F2) T2 CH3 cyclopropyl 71 70.1 to 70.14 (F2) T2 H CH3C(O)OCH2 72 71.1 to 71.14 (F2) T2 CH3 CH3C(O)OCH2

Table T2

____ R1 R3 1 H H 2 F H 3 CI H 4 CH3 H CF3 H 6 CN H 7 ethynyl H 8 H CF-I3 9 F CH3 Cl CH3 11 CH3 CF-I3 12 CF3 CF-I3 13 CN CH3 14 ethynyl CH3 BIOLOGICAL EXAMPLES: FUNGICIDAL ACTION: I Phvtophthora infestans / tomato / leaf disc preventative (late blight) Tomato leaf disks were placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200ppm. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf disks were incubated at 16°C and 75% relative humidity under a light regime of 24 h darkness followed by 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (5-7 days after application).

2 Plasmopara viticola / grape / leaf disc preventative (late blight) Grape vine leaf disks were placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200ppm. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf disks were incubated at 19°C and 80% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (6 -8 days after application).

3 BlumerIa gramInIs f. sp. trIticI (Erysiphe praminis f. sp. tritici) / wheat / leaf disc preventative (Powdery mildew on wheat): Wheat leaf segments cv. Kanzler were placed on agar in a 24-well plate and sprayed with the formulated test compound diluted in water at an application rate of 200ppm. The leaf disks were inoculated by shaking powdery mildew infected plants above the test plates I day after application.

The inoculated leaf disks were incubated at 20°C and 60% relative humidity under a light regime of 24 h darkness followed by 12h/12h (darkllight) in a climate chamber and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6-8 days after application).

4 PuccInIa recondita 1. sp. tirItIcI / wheat I leaf disc preventative (Brown rust): Wieat leaf segments cultivated variety (cv) Kanzler were placed on agar in 24-well plates and sprayed with formulated test compound diluted in water at an application rate of 200ppm. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated S leaf segments were incubated at 19°C and 75% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 -9 days after application).

Phaeosphaeria nodorum (Seytoria nodorum) /wheat / leaf disc preventative (Glume blotch): tieat leaf segments cv Kanzler were placed on agar in a 24-well plate and sprayed with formulated test compound diluted in water at an application rate of 200ppm. The leaf disks were inoculated with a spore suspension of the fungus 2 days after application. The inoculated test leaf disks were incubated at 20°C and 75% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (5- 7 days after application).

6 Pvrenooliora teres / barley / leaf disc preventative (Net blotch): Barley leaf segments cv Hasso were placed on agar in a 24-well plate and sprayed with formulated test compound diluted in water at an application rate of 200ppm. The leaf segments were inoculated with a spore suspension of the fungus two days after application of the test solution. The inoculated leaf segments were incubated at 20°C and 65% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5 -7 days after application).

7 Alternaria soiani / tomato / leaf disc (early blight) Tomato leaf disks cultivated variety (cv.) Baby were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200ppm. The leaf disks were inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf disks were incubated at 23°C/21°C (day/night) and 80% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check disk leaf disks (5-7 days after application).

8 Magnaporthe grIsea (Pyricularia oryzae) / rice / leaf disc preventative (Rice Blast): Rice leaf segments cv. Ballila were placed on agar in multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200ppm. The leaf segments were inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments were incubated at 22°C and 80% rh under a light regime of 24 h darkness followed by 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5-7 days after application).

9 PythIum ultImum I liquid culture (seedling damping off) Mycelia fragments and oospores of a newly grown liquid culture of the fungus were directly mixed into nutrient broth (potato dextrose broth). After placing a DMSO solution of test compound into a 96-well format microtiter plate at an application rate of 2oppm, the nutrient broth containing the fungal mycelia/spore mixture was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 2-3 days after application.

Botryotinia fuckeliana (Botrytis cinerea) / liquid culture (Gray mould): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (Vogels broth). After placing a DM80 solution of test compound into a 96-well microtiter plate at an application rate of 20ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 3-4 days after application.

11 Glomerella IagenarIum (Co//etotrichum Iagenarium) / liquid culture (Anthracnose) Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 20ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was measured photometrically 3-4 days after application.

12 Mycosphaerella arachldIs (Cercospora arachidicola) I liquid culture (early leaf spot): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DM80 solution of test compound into a 96-well microtiter plate at an application rate of 2Oppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application.

13 Mycosøhaerella Qramlnicola (Septoria tritici) / liquid culture (Septoria blotch): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DM50 solution of test compound into a 96-well microtiter plate at an application rate of 20ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application.

14 Gaeumannomyces graminis I liquid culture (Take-all of cereals): Mycelial fragments of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DM50 solution of test compound into a 96-well microtiter plate at an application rate of 2oppm, the nutrient broth Cp.33, containing the fungal spores is added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application.

Monographella nivalis (Micmdochium n/vale) / liquid culture (foot rot cereals): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DM50 solution of test compound into a 96-well microtiter plate at an application rate of 2Oppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application.

16 Fusarium culmorumi liquid culture (Head blight): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) at an application rate of 20ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined visually 3-4 days after application.

17 Thanatephorus cucumeris (Rhizoctonia so/ani) / liquid culture (foot rot, dampinq-offi: Mycelia fragments of a newly grown liquid culture of the fungus were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compounds into a 96-well microtiter plate at an application rate of 20ppm, the nutrient broth containing the fungal material was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 3-4 days after application.

18 Sclerotinia scierotlorum / liquid culture (cottony rot) Mycelia fragments of a newly grown liquid culture of the fungus were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) at an application rate of 2oppm, the nutrient broth containing the fungal material was added. The test plates were incubated at 24°C and the inhibition of growth was determined visually 3-4 days after application.

19 Fusagrium culmorum (Head blight! spikelet) Fusarium culmorum (Head blight): Wheat spikelets are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the spikelets are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed 6 dpi (days after inoculation) as preventative fungicidal activity.

Gibberelia zeae (Head blightl spikelet) Fusarium graminearum, syn. Gibberella zeae, (Head blight): Wheat spikelets are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the spikelets are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed 6 dpi (days after inoculation) as preventative fungicidal activity.

The following compounds gave at least 60% control of the following fungal infection at 200ppm: Plasmopara viticola. compounds: P8, P9, P12, P14, P19, P21.

Erysiphe praminis tsp. tritici, compounds: P8, P10, P13, P18.

Puccinia recondita f. sp. tnt/cl, compounds: P8, P12, P13, P14, P15, P16, P17, P21.

Phaeosphaerianodorum, compounds: P8, P12, P13, P14, P16, P17.

Pyrenophora teres, compounds: P5, P8, P9.

Alternaria solani, compounds: P5, P7, P8, P10, P13, P14, P17.

Pyricu/aria oryzac, compounds: P8, P10, P13, P14, P17.

The following compounds gave at least 60% control of the following fungal infection at 2oppm: Pythium ultimum, compounds: P1, P2, P3, P4, P6, P7, P9, P10, P13, P14, P15, P17, P18, P19, P20, P21, P22.

Botrytiscinerea, compounds: P2, P6, P7, P8, P9, P10, P11, P12, P13, P14, P15, P16, P17, P18, P19.

Glomerella Iagenarium compounds: P11, P12, P13, P14, P15, P16, P17, P18, P19, P20, P21, P22.

Mycosphaerella arachidis, compounds: P2, P3, P5, P6, P7, P8, P9, P10, P11, P12, P13, P14, P15, P16, P17, p18, P19, P20.

Mycosphaerellapraminicola, compounds: P2, P3, P5, P8, P9, P10, P12, P13, P14, P15, P16, P17, P19.

Gaeumannomycesczraminis, compounds: P2, P3, P5, P6, P7, P8, P9, P10, P11, P12, P13, P14, P15, P16, P17, P18, P20, P21, P22.

Monographelfanivalis, compounds: P2, P3, P5, P6, P7, P8, P9, P10, P11, P12, P13, P14, P15, P16, P17, P18, P19, P20, P21, P22.

Fusariumcu/morum, compounds: P2, P5, P6, P7, P10, P11, P12, P13, P14, P15, P16, P17, P18, P19,P21,P22.

Thanatephoruscucumeris, compounds: P10, P14, P15, P17.

Sclerotiniascierotiorum, compounds: P2, P4, P6, P7, P10, P11, P12, P13, P14, P15, P16, P17, P18, P19.

The following compounds gave at least 60% control of the following fungal infection at 200ppm: Fusarium culmorum (Head bliciht/ spikelet), compounds: P13, P15.

Gibberella zeae (Head bliciht/ spikelet), compound: P15.

Claims (14)

1. Claims: 1. Compounds of formula (I) B' (I) wherein R1 is hydrogen, halogen, cyano, C1-C5alkyI which can be substituted by one or more substituents R3, C3-C5cycloalkyl which can be substituted by one or more substituents R8, C2-C5alkenyl which can be substituted by one or more substituents R3, C2-C5alkynyl which can be substituted by one or more substituents R8, C1-C5haloalkyl, C(O)(C1-C4)alkyl which can be substituted by one or more substituents R, C(O)O(C1-C4)alkyl which can be substituted by one or more substituents RB; R2 is hydrogen, C1-C5alkyI which can be substituted by one or more substituents R3, C3-C5cycloalkyl which can be substituted by one or more substituents R5, C1-C6haloalkyl, C2-C6alkenyl which can be substituted by one or more substituents R5, C2-C6alkynyl which can be substituted by one or more substituents R3, C(O)H, C(O)(C1-C4)alkyl which can be substituted by one or more substituents R3, C(O)phenyl which can be substituted by one or more substituents R7, C(O)O(C1-C4)alkyl which can be substituted by one or more substituents R8; or R2 is a moiety of the following structure [w R3 and R4 are, independently from each other hydrogen, C1-C6alkyl which can be substituted by one or more substituents R8, C1-C6haloalkyl, C2-C3alkenyl which can be substituted by one or more substituents R3, C2-C5alkynyl which can be substituted by one or more substituents R3, C3-C5cycloalkyl which can be substituted by one or more substituents R8, phenyl which can be substituted by one or more substituents R7 or R3 and R4 may form together with the carbon atom to which they are attached an aliphatic 3 to B membered ring which can be substituted by one or more R5 and R5 are, independently from each other hydrogen, halogen, C1-C5alkyl which can be substituted by one or more substituents R5, C1-C6haloalkyl C2-C5alkenyl which can be substituted by one or more substituents R5, C2-C6alkynyl which can be substituted by one or more substituents R5, C3-C5cycloalkyl which can be substituted by one or more substituents R3, C3-C6alkynyl which can be S substituted by one or more substituents R3, phenyl which can be substituted by one or more substituents R7 or R5 and R6 may form together with the carbon atom to which they are attached an aliphatic 3 to 8 membered ring which can be substituted by one or more substituents R7; W is hydrogen, OH, SH, NH2, C1-C3alkylamino which can be substituted by one or more substituents R3, di(C1-C5alkyl)amino which can be substituted by one or more substituents R5, C1-C6alkoxy which can be substituted by one or more substituents R8, C1-C5haloalkoxy, C1-C6alkylthio which can be substituted by one or more substituents R3, OC(O)(C1-C4)alkyl which can be substituted by one or more substituents R8, OC(O)(C1-C4)haloalkyl, C1-C4alkyl-O-N=CH-which can be substituted by one or more substituents R3, HO-N=CH-, -O-N=C-(C1-C4alkyl) which can be substituted by one or more substituents R3, C1-C5alkyl which can be substituted by one or more substituents R8, C1-C6haloalkyl, C2-C5alkenyl which can be substituted by one or more substituents R8, C2-C5alkynyl, C3-C5cycloalkyl which can be substituted by one or more substituents Ra, mono-or bi-cyclic six-to ten-membered aryl which can be substituted by one or more substituents R7, five-to ten-memberd heteroaryl contains 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms and the heteroaryl can be substituted by one or more substituents R7; n is 0,1,2,3,4,5 or6; m is 1; R7 is independently selected from the group consisting of halogen, OH, NH2, cyano, nitro, C1-C5alkyl, C1-C5haloalkyl, C1-C5alkylamino, di(C1-C3alkyl)amino, C1-C6alkoxy, C1-C5alkoxy-C1-C5alkyl, C1- C3haloalkoxy, C1-C6alkoximino and C1-C5alkylendioxy, C(O)(C14 alkoxy), -C(O)(C14 alkyl), -OC(O)(C1-4 alkyl), -C(O)-NH-(C14 alkyl), -C(O)-N(C14 alkyl)2, -C(O)H, -C(O)OH; R3 is independently selected from -OH, CN, NH2, NO2, F, Cl, C14alkoxy, -C(O)(C14alkoxy), -OC(O)(C1-4 alkyl), -C(O)(C1-4 alkyl), -C(O)-NH-(C14 alkyl), -C(O)-N(C14 alkyl)2 and C14alkylamino; and agronomically acceptable salts, stereoisomers, diastereoisomers, enantiomers, tautomers, atropisomers and N-oxides of those compounds.
2. 2. Compounds of formula (I) according to claim 1 wherein R1 is hydrogen, halogen, CN, C1-C5alkyl which can be substituted by one or more substituents R3, C1-C5haloalkyl, C2-C4alkynyl which can be substituted by one or more substituents R3.
3. 3. Compounds of formula (I) according to claim 1 or 2 wherein R2 is hydrogen, C1-C6alkyl which can be substituted by one or more substituents R8, C1-C5haloalkyl, C(O)aryl which can be substituted by one or more substituents R7, C(O)C1-C4alkyl which can be substituted by one or more substituents R3, C(O)0C1-C4alkyl which can be substituted by one or or R2 isa moiety of the following structure [w
4. 4. Compounds of formula (I) according to any of the claims ito 3 wherein R5 and R5 are independently from each other hydrogen, halogen, C1-C5alkyl which can be substituted by one or more substituents R8, C1-C5haloalkyl; and m is I and n isO, i, 2, 3, or 4.
5. 5. Compounds of formula (I) according to any of the claims i to 4 wherein W is hydrogen, OH, SH, C1-C5alkylamino which can be substituted by one or more substituents R8, di(C1-C5alkyl)amino which can be substituted by one or more substituents R3, C1-C5alkoxy which can be substituted by one or more substituents Ra, C1-C6haloalkoxy which can be substituted by one or more substituents R3, C1-C6alkylthio which can be substituted by one or more substituents R5, C1-C5alkyl; OC(O)(C1-C4)alkyl which can be substituted by one or more substituents R8.
6. 6. Compounds of formula (I) according to any of the claims i to 5 wherein R1 is halogen, methyl, trifluoromethyl, cyano, ethynyl.
7. 7. Compounds of formula (I) according to any of the claims ito 6 wherein R2 is hydrogen or C(O)aryl which can be substituted by one or more substituents R7, C(O)C1-C4alkyl which can be substituted
8. 8. Compounds of formula (I) according to any of the claims i to 7 wherein R7 is independently selected from the group consisting of halogen, OH, NH2, cyano, nitro, C1-C5alkyl, C1-C5haloalkyl; and R8 is independently selected from -OH, CN, NH2, NO2, F, Cl, C1.4alkoxy, -C(O)(C14alKoxy), -OC(O)(C1-4 alkyl) -C(O)(C1-4 alkyl).
9. 9. A method for controlling or preventing infestation of plants or plant propagation material and/or harvested crops susceptible to microbial attack, characterized in that an effective amount a compound of formula (I) as defined in anyone of the claims ito 8 is applied to the plants or plant propagation material and/or harvested food, or to pads thereof or the locus thereof.
10. 10. A method of controlling phytopathogenic diseases on plants or plant propagation material and/or harvested crops susceptible to microbial attack, characterized in that an effective amount a compound of formula (I) as defined in anyone of the claims ito 8 is applied to the plants or plant propagation material and/or harvested food, or to parts thereof or the locus thereof
11. 11. A composition comprising a fungicidally effective amount of a compound of formula (I) as defined in anyone of the claims ito 8.
12. 12. A process for the preparation of a compound of formula (I) io N B' OH (I) wherein R1, R2, R3, R4, R5, R5, and Ware as defined in any of the claims ito 8 comprising reacting a compound of formula (Ill) i5 H:N (Ill), with a compound of formula (IV) (IV), in which X is Cl, Br, I, OS(O)2Me, OS(O)2-C6H4-Me; preferably Bromo.
13. 13. A process for the preparation of a compound of formula (I) N' B"OHwherein R2 is C(O)aryl, C(O)C1-C4aIkyl, C(O)0C1-C4alkyI and R1, R3, R4, R5, R5, and Ware as defined in any of the claims ito 8 comprising reacting a compound of formula (Ill) H:N':JIzIIIIL'I; (Ill), with a compound of formula WI) (VI), wherein U is aryl, C1-C4alkyl, 0C1-C4alkyl to obtain a compound of formula (V)H OHand reacting the compound of formula (V) with a compound of formula (IV) (IV)
14. 14. Compounds obtainable by a process according to claim 12 or 13. i5