WO2007017231A1

WO2007017231A1 - Use of arylanilides for seed treatment

Info

Publication number: WO2007017231A1
Application number: PCT/EP2006/007801
Authority: WO
Inventors: Jochen Dietz; Siegfried Strathmann; Reinhard Stierl; Peter Dombo; Markus Gewehr; Wassilios Grammenos; Thomas Grote; Bernd Müller; Jan Klaas Lohmann
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 2005-08-05
Filing date: 2006-08-07
Publication date: 2007-02-15
Anticipated expiration: 2008-02-05
Also published as: PE20070595A1; TW200738143A; UY29723A1; AR056447A1

Abstract

The invention relates to the use of arylanilides of the formula (I) wherein the variables are as defined in the description, for seed treatment and corresponding methods of seed treatment for controlling phytopathogenic fungi. The invention also relates to seed treatment formulations comprising the arylanilides of formula I and to seeds treated therewith.

Description

Use of arylanilides for seed treatment

Description

The invention relates to a method of seed treatment, which comprises treating a seed with an effective amount of an arylanilide of the formula I

wherein

X is halogen;

Y is oxygen or sulfur; n is zero, 1 , 2, 3 or 4;

R is d-Cβ-alkyl, Ci-C₈-haloalkyl, C₂-C₈-alkenyl, C₂-C₈-haloalkenyl, C₃-C₈-cycloalkyl or C₃-C₈-cycloalkenyl;

Ar is an aryl radical of the formula Ma, lib or Hc

wherein R¹ is hydrogen, halogen, Ci-C4-alkyl or Ci-C4-haloalkyl;

R² is CrC₄-alkyl; R³ is hydrogen, halogen or methyl; R⁴ is hydrogen, halogen, Ci-C4-alkyl, or CrC4-haloalkyl; R⁵ is CrC₄-alkyl or CrC₄-haloalkyl; Z is CH or N and

R⁶ is halogen, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy, Ci-C₄-alkylthio, Ci- C4-alkylsulfinyl or Ci-C4-alkylsulfonyl.

The invention also relates to seed treatment formulations and to seeds.

During the time period before and during germination and sprouting plants tend to be especially vulnerable to an attack of phytopathogenic fungi, not only because of the low size of the developing plant organs which makes them incapable of coping with much damage, but also because some of the natural plant defense mechanisms are not yet developed at that stage of development. Protection of plants in the pre- and post- germination stage is therefore instrumental in reducing damage.

However, the conventional application of fungicides to plants and their environment can suffer from a large number of disadvantages: Resistance to a given fungicide often develops quickly, especially if usage is very widespread, so new agents will have to be developed continually. The possible detrimental effects of fungicides on public health and on the environment are a matter of public concern. More specifically, lavish use of fungicides is not only expensive but also poses a serious health hazard to agricultural laborers; this is a particular concern for dusts or dustable powders. It is therefore advisable to use as low dosages as possible. Moreover, the efficacy of fungicides against soil-borne fungi, especially against subterraneous species, leaves much to be desired. Proper management of the fungi requires good timing and much hands-on work and may, depending on the formulation used, be very sensitive to abiotic factors which are difficult to control, such as wind, temperature, and rain fall. There is always the generally undesirable possibility of fungicides diffusing away from the desired site of action ("fungicide drift").

Ideally, the fungicide should therefore be effective in comparatively low dosages, not liable to large-scale diffusion into the environment and away from the crops to be protected (thereby leading to undesired "bystander effects"), and suitable for such procedures as minimize both exposure of humans and hands-on time. Furthermore, it should be active against a broad spectrum of phytogathogenic fungi and preferably combine immediate effects ("knock-down") with prolonged control.

Until recently, in the most important regions for the cultivation of leguminous plants (in particular soybeans) there were no infections with harmful fungi that were of economic significance. However, over recent years, there has been an increase in severe rust infections of soybean crops in South America by the harmful fungi Phakopsora pachyrh/zi and Phakopsora meibomiae. Further, an increased occurrence of pathogenic fungi, such as Rhizoctonia in rice, is observed. There have been considerable harvest and yield losses.

Most customary fungicides are unsuitable or unsatisfactory for controlling such pathogenic fungi.

An object of the present invention was to provide a method for the protection of crops from damage by phytopathogenic fungi. Preferably, it should also solve the problem of reducing the dosage rate, combine knock-down activity with prolonged control and/or be suitable for resistance management. Surprisingly, it has now been found that treatment of unsown plant seeds with the arylanilides I not only protects the seeds themselves, but also provides post- emergence control of phytopathogenic fungi that damage the seeds or the plants that grow from the seeds.

The invention therefore relates to the use of the arylanilides I for seed treatment and to a method of seed treatment, which comprises treatment of seed with an effective amount of an arylanilide I.

The invention offers several advantages: It focuses fungicide effects on crops and the fungi, thereby minimizing human exposure and environmental side-effects as well as the total dosage required, is effective against underground plant diseases, less dependant on abiotic factors and conveniently applied.

The arylanilides I are known, for example, from EP-A 545099, EP-A 589301 and earlier German application no. 102005039785.9, or can be prepared according to the methods described therein.

Suitable compounds of the formula I encompass all possible stereoisomers (cis/trans isomers, enantiomers) which may occur and mixtures thereof. The present invention provides both the use of the pure enantiomes or diastereomers or of the mixtures thereof, of the pure cis- and trans-isomers and of the mixtures thereof. The compounds of the general formula I may also exist in the form of different tautomers. The invention comprises the use of the single tautomers, if seperable, as well as of the tautomer mixtures.

The compounds of the formula I may be present in various crystal modifications which may differ in their biological activity. Their use also forms part of the subject matter of the present invention.

The term halogen denotes in each case fluorine, bromine, chlorine or iodine.

The term "Ci-C₄-alkyl" (also in groups such as CrC₄-alkoxy, Ci-C₄-alkylthio, CrC₄- sulfinyl or Ci-C₄-sulfonyl etc.) as used herein refers to a branched or unbranched saturated hydrocarbon group having 1 to 4 carbon atoms, for example methyl, ethyl, n- propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl and 1 ,1-dimethylethyl.

The term "d-Cβ-alkyl" as used herein refers to a branched or unbranched saturated hydrocarbon group having 1 to 8 carbon atoms, for example methyl, ethyl, n-propyl, 1- methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1 ,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methyl- pentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-di- methylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1 ,2-tri- methylpropyl, 1 ,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n- heptyl, 1-ethyl-2,2-dimethylpropyl, 1 ,3,3-trimethylbutyl, n-octyl, 1 ,1 ,3,3-tetramethylbutyl, 2,4,4-trimethylpentyl or 2-etylhexyl, preferably Ci-C4-alkyl as outlined above, or n-propyl, n-butyl, 1-methyl-propyl, 2-methylpropyl, n-pentyl, n-hexyl, 2-ethylbutyl, 1 ,3-dimethylbutyl or 1 ,3,3-t6ri-methylbutyl, in particular 1 ,3-dimethylbutyl or 1 ,3,3-trimethylbutyl.

The term "Ci-C4-haloalkyl" as used herein refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, for example C₁-C2 haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2- difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl, or C3-C₄ haloalkyl, such as 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1 -(fluoromethyl)-2-fluoroethyl, 1 -(chloromethyl)-2-chlorethyl, 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl, heptafluoro-2-propyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.

The term "d-Cβ-haloalkyl" as used herein refers to a straight-chain or branched alkyl group having 1 to 8 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, for example chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2- chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 2,2,2-trifluoroethyl, 2- chloro-1 ,1 ,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2-bromo-2,2-difluoroethyl, 2,2- dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1 , 1 ,2,2-tetrafluoroethyl, 1 , 1 ,2,2- tetrachloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3- difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3- bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2, 3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoropropyl, 1 , 1 ,2,3,3,3-hexafluoro-1 -propyl, 1 ,1 ,1 ,3,3,3-hexafluoro-2- propyl, heptafluoro-1 -propyl, heptafluoro-2-propyl, 1-(fluoro-methyl)-2-fluoroethyl, 1- (chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-biOmoethyl, 4-fluoro-butyl, 4-chlorobutyl, 4-bromobutyl, 2,2,3,3,4,4,4-heptafluoro-i -butyl, nonafluoro-1 -butyl, 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5,5,5-trichloropentyl, undecafluoropentyl, 6-fluoro-hexyl, 6- chlorohexyl, 6-bromohexyl, 6,6,6-trichlorohexyl, dodecafluorohexyl or 7-chloro-hept-1-yl, preferably Ci-C₄-haloalkyl.

The term "C₂-C8-alkenyl" as used herein refers to an unsaturated straight-chain or branched hydrocarbon radical having 2 to 8 carbon atoms and one or two double bonds in any position, for example ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1- butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl- 1-propenyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-me- thyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-1 -butenyl, 1-methyl-2-butenyl, 2-methyl-2- butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-bu- tenyl, 1 ,1-dimethyl-2-propenyl, 1 ,2-dimethyl-1-propenyl, 1 ,2-dimethyl-2-propenyl, 1- ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5- hexenyl, 1 -methyl- 1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1- pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2- pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3- pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4- pentenyl, 1 ,1-dimethyl-2-butenyl, 1 ,1-dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-di- methyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1-butenyl, 1 ,3-dimethyl-2-bu- tenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2, 3-dimethyl-1 -butenyl, 2,3-di- methyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1 -butenyl, 3,3-dimethyl-2-bu- tenyl, 1-ethyl-1 -butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1 -butenyl, 2-ethyl- 2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1- ethyl-2-methyl- 1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term "C2-C8-haloalkenyl" as used herein refers to an unsaturated straight-chain or branched hydrocarbon radical having 2 to 8 carbon atoms and one or two double bonds in any position (as mentioned above), where in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, in particular by fluorine, chlorine and/or bromine.

The term "Ca-Cs-cycloalkyl" as used herein refers to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, preferably cyclopentyl and cyclohexyl.

The term "Ca-Cβ-cycloalkenyl" as used herein refers to cycloprop-1-enyl, cycloprop-2- enyl, cyclobut-1-enyl, cyclobut-2-enyl, cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3- enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1-enyl, cyclohept-2- enyl, cyclohept-3-enyl, cyclohept-4-enyl, cyclooct-1-enyl, cyclooct-2-enyl, cyclooct-3- enyl and cyclooct-4-enyl, preferably cyclopent-2-enyl and cyclohex-2-enyl.

Among the arylanilides of formula I, preference is given to those in which the variables, both on their own and in any combination with one another, have the meanings given below: X fluorine or chlorine, in particular fluorine;

Y oxygen; Z nitrogen; n zero or one, in particular zero;

R Ci-C₄-alkyl, Ci-C₄-haloalkyl, C₃-Alkenyl, C₅-C₆-Cycloalkyl or Cs-Ce-Cycloalkenyl, in particular methyl, ethyl, 1 -propyl, 2-propyl, d-C^haloalkyl, allyl, cyclopentyl or cyclohexyl, with particular preference difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2,-tetrafluoroethyl, 2-chloro-1 ,1 ,2- trifluoromethyl, 2,2,3,3-tetrafluoropropyl or 1,1,2,3,3,3-hexafluoropropyl, very particularly preferred 1 ,1,2,2,-tetrafluoroethyl, 2-chloro-1 ,1 ,2-trifluoroethyl or 1 ,1 ,2,3,3,3-hexafluoropropyl; R¹ methyl or halomethyl, in particular methyl, difluoromethyl or trifluoromethyl, with particular preference difluoromethyl; R² methyl;

R³ hydrogen, fluorine or chlorine, in particular hydrogen;

R⁴ Ci-C₄-alkyl, in particular methyl;

R⁵ methyl or halomethyl, in particular methyl, difluoromethyl or trifluoromethyl, with particular preference difluoromethyl or trifluoromethyl; R⁶ halogen, methyl or halomethyl, in particular fluorine, chlorine, iodine, methyl, difluoromethyl or trifluoromethyl, with particular preference chlorine, iodine or trifluoromethyl.

Another embodiment of the present invention relates to compounds of the formula I, wherein n is one.

According to a preferred embodiment the compounds of formula I are used wherein

X is halogen;

Y is oxygen; n is zero, 1 , 2, 3 or 4;

R is d-Ce-haloalkyl or C2-C₆-haloalkenyl;

Ar is an aryl radical of the formula Ma, Mb or Mc

wherein

R¹ is Ci-C₄-alkyl or Ci-C₄-haloalkyl; R² is CH₃;

R³ is hydrogen or halogen;

R⁴ is Ci-C₄-alkyl or Ci-C₄-haloalkyl;

R⁵ is Ci-C₄-alkyl or Ci-C₄-haloalkyl;

R⁶ is halogen, Ci-C₄-alkyl or Ci-C₄-haloalkyl, Ci-C₄-alkoxy, CrC₄-alkylthio, Cr C₄-sulfinyl or Ci-C₄-alkylsulfonyl; and

Z is N.

According to a further preferred embodiment the compounds of formula I are used wherein

X is halogen;

Y is oxygen; n is 0 or 1 ;

R is C2-C₄-haloalkyl; Ar is an aryl radical of the formula Ha₁ lib or He

^llc-

wherein

R¹ is Ci-C₄-alkyl or Ci-C₄-haloalkyl;

R² is CH₃;

R³ is hydrogen or halogen;

R⁴ is Ci-C₄-alkyl

R⁵ is CrC₄-alkyl or Ci-C₄-haloalkyl;

R⁶ is halogen, C i-C₄-alkyl or Ci-C₄-haloalkyl; and

Z is N.

According to a further preferred embodiment the compounds of formula I are used wherein X is halogen;

Y is oxygen; n is zero or 1 ;

R is Ci-Ce-haloalkyl or C2-C₆-haloalkenyl; Ar is an aryl radical of the formula Ma, Mb or Mc

wherein R¹ is Ci-C₄-alkyl or Ci-C₄-haloalkyl;

R² is CH₃;

R³ is hydrogen or halogen;

R⁴ is CrC₄-alkyl;

R⁵ is CrC₄-alkyl or Ci-C₄-haloalkyl; R⁶ is halogen, Ci-C₄-alkyl, or Ci-C₄-haloalkyl; and

Z is N.

X is halogen;

Y is oxygen; n is zero or 1 ; R is C₂-C₄-haloalkyl; Ar is an aryl radical of the formula Ma, Mb or Mc

wherein R¹ is Ci-C₄-alkyl or d-C₄-haloalkyl;

R² is CH₃;

R³ is hydrogen or halogen;

R⁴ is CH₃;

R⁵ is CrC₄-alkyl or d-C₄-haloalkyl; R⁶ is halogen, Ci-C₄-alkyl or Ci-C₄-haloalkyl; Z is N.

From this embodiment the following compounds may be excluded: 1 ,3-dimethylpyrazol- 4-yl-carboxylic acid-N[2-(1 _I1 _I2,2,-tetrafluoroethoxy)-phenyl]amide and 3-trifluoromethyl- 5 i-methyl-pyrazol-4-yl-carboxylic acid-N[2-(1 ,1 ,2,2,-tetrafluoroethoxy)phenyl]amide.

X is halogen; O n is zero, 1 or 2, where in case that n is 2, the radicals X may have the same or different meanings; R is Ci-Cβ-alkyl, CrC₈-haloalkyl, C₂-C₈-alkenyl, C₂-C₈-haloalkenyl, C₃-C₈-cycloalkyl or C₃-C₈-cycloalkenyl;

Ar is an aryl radical of the formula Ma₁ Mb or Mc 5

wherein

R¹ is hydrogen, halogen, Ci-C₄-alkyl or Ci-C₄-haloalkyl;

R² is Ci-C₄-alkyl; 0 R³ is hydrogen, halogen or methyl;

R⁴ is hydrogen, halogen or Ci-C₄-alkyl;

R⁵ is CrC₄-alkyl or Ci-C₄-haloalkyl;

Z is CH or N and

R⁶ is halogen, Ci-C₄-alkyl or Ci-C₄-haloalkyl. 5

One embodiment of the present invention relates to compounds of the formula Ia

wherein X, n, R, R¹, R² and R³ are as defined herein. Amongst compounds Ia, preference is given to those, wherein n is zero or one. 0 Further preference is given to those compounds Ia, wherein R³ is fluorine. Further preference is given to those compounds Ia, wherein R³ is chlorine. Further preference is given to those compounds Ia, wherein R³ is hydrogen. Further preference is given to those compounds Ia, wherein R² is methyl. Further preference is given to those compounds Ia₁ wherein R¹ is Ci-C₄-alkyl or Ci-C₄-haloalkyl, in particular methyl, trifluoromethyl or difluoromethyl. Further preference is given to those compounds Ia, wherein X is fluoro or chloro, in particular fluoro. Further preference is given to those compounds Ia₁ wherein R is Ci-C₄-haloalkyl, in particular 1 , 1 ,2,2-tetrafluoroethyl, 2-chloro-1 ,1 ,2-trifluoroethyl or 1 ,1 ,2,3,3,3-hexafluoropropyl, in particular 2-chloro-1 ,1 ,2-trifluoroethyl or 1 , 1 ,2,3,3,3-hexafluoropropyl.

Compounds Ia with R² = CH3 depicted in the following Table 1 are very particularly preferred:

Table 1

The most preferred compounds are Ia.1 , la.2, la.23, Ia.24, la.25 and la.26.

A further embodiment of the present invention relates to compounds of the formula Ib

wherein X, n, R, R⁴ and R⁵ are as defined herein.

Amongst compounds Ib, preference is given to those, wherein n is zero or one.

Further preference is given to compounds Ib, wherein R⁴ is Ci-C4-alkyl, in particular methyl. Further preference is given to compounds Ib, wherein R⁵ is Ci-C4-alkyl or

Ci-C₄-haloalkyl, in particular CH₃, CF₃ or CHF₂.

Further preference is given to compounds Ib, wherein X is fluoro or chloro, in particular fluoro.

Further preference is given to compounds Ib, wherein n is zero. Further preference is given to compounds Ib, wherein R is Ci-C4-haloalkyl, in particular

1 , 1 ,2,2-tetrafluoroethyl, 2-chloro-1 , 1 ,2-trifluoroethyl or

1 ,1 ,2,3,3,3-hexafluoropropyl, preferably 2-chloro-1 ,1 ,2-trifluoroethyl or

1 , 1 ,2,3,3,3-hexafluoropropyl.

Compounds Ib depicted in the following Table 2 are very particularly preferred:

Table 2

A further embodiment of the present invention relates to compounds of the formula Ic

wherein X, n, R and R⁶ are as defined herein. Amongst compounds Ic, preference is given to those, wherein n is zero or one.

Further preference is given to compounds Ic, wherein X is fluoro or chloro, in particular fluoro.

Further preference is given to compounds Ic, wherein R⁶ is halogen or C1-C4- haloalkyl, in particular chloro, iodo, trifluoromethyl or difluoromethyl.

Further preference is given to compounds Ic, wherein R is Ci-C4-haloalkyl, in particular 1 ,1 ,2,2-tetrafluoroethyl, 2-chloro-1 ,1 ,2-trifluoroethyl or 1 ,1 ,2,3,3,3-hexafluoropropyl, preferably 2-chloro-1 ,1 ,2-trifluoroethyl or 1 ,1 ,2,3,3,3-hexafluoropropyl.

Compounds Ic depicted in the following Table 3 are very particularly preferred:

Table 3

A further embodiment of the present invention relates to compounds of the formula Id

wherein X, n, R and R⁶ are as defined herein. Amongst compounds Id, preference is given to those, wherein n is zero or one.

Further preference is given to compounds Id, wherein R⁶ is halogen, in particular chloro.

Further preference is given to compounds Id, wherein X is fluoro or chloro, in particular fluoro.

Further preference is given to compounds Id, wherein R is Ci-C4-haloalkyl, in particular 1 ,1 ,2,2-tetrafluoroethyl, 2-chloro-1 ,1 ,2-trifluoroethyl or 1,1 ,2,3,3,3-hexafluoropropyl, preferably 2-chloro-1 ,1,2-trifluoroethyl or 1 ,1 ,2,3,3,3-hexafluoropropyl.

Compounds Id depicted in the following Table 4 are very particularly preferred:

Table 4

As used herein, the term "seed" denotes any resting stage of a plant that is physically detached from the vegetative stage of a plant and/or may be stored for prolonged periods of time and/or can be used to re-grow another plant individual of the same species.

Here, the term "resting" refers to a state wherein the plant retains viability, within reasonable limits, in spite of the absence of light, water and/or nutrients essential for the vegetative (i.e. non-seed) state. In particular, the term refers to true seeds but does not embrace plant propagules such as suckers, corms, bulbs, fruit, tubers, cuttings and cut shoots.

As used herein, the term "plant" means an entire plant or parts thereof. The term "entire plant" refers to a complete plant individual in its vegetative, i.e. non-seed stage, characterized by the presence of an arrangement of roots, shoots and foliage, depending on the developmental stage of the plant also flowers and/or fruits, all of which are physically connected to form an individual which is, under reasonable conditions, viable without the need for artificial measures. The term may also refer to an entire plant harvested as such.

The term "plant parts" refers to roots, shoots, foliage, flowers or other parts of the vegetative stage of the plant, which, when dislodged and disconnected from the rest, are incapable of survival, unless supported by artificial measures or able to re-grow the missing parts to form an entire plant. As used herein, fruits are also considered as plant parts.

As used herein, the term "root" refers to parts of a plant which are normally, in order to fulfill their physiological functions, located beneath the soil surface. Preferably, the term denotes the parts of a plant which are below the seed and have directly emerged from the latter, or from other roots, but not from shoots or foliage.

As used herein, the "shoots and foliage" of a plant are to be understood to be the shoots, stems, branches, leaves and other appendages of the stems and branches of the plant after the seed has sprouted, but not including the roots of the plant. It is preferable that the shoots and foliage of a plant be understood to be those non-root parts of the plant that have grown from the seed and are located a distance of at least one inch away from the seed from which they emerged (outside the region of the seed), and more preferably, to be the non-root parts of the plant that are at or above the surface of the soil.

As used herein, "fruits" are considered to be the parts of a plant which contain seeds and/or serve to spread seeds, and/or which may be removed from a plant without impairing its viability.

According to the present invention, the seed treatment comprises applying an arylanilide of the formula I to a seed. The seed may be from naturally occuring plants, from plants obtained by means of classical breeding or from genetically modified plants, for example glyphosate tolerant soybean plants.

Although the present method can be applied to a seed in any physiological state, it is preferred that the seed be in a sufficiently durable state that it incurs no significant damage during the treatment process. Typically, the seed is a seed that has been harvested from the field; removed from the plant; and/or separated from the fruit and any cob, pod, stalk, outer husk, and surrounding pulp or other non-seed plant material. The seed is preferably also biologically stable to the extent that the treatment would cause no biological damage to the seed. In one embodiment, for example, the treatment can be applied to seed that has been harvested, cleaned and dried to a moisture content below about 15% by weight. In an alternative embodiment, the seed can be one that has been dried and then primed with water and/or another material and then re-dried before or during the treatment with the arylanilide of formula I.

In a further embodiment, the seed can be one from genetically modified plants, in particular soybean plants, or rice plants.

The term seed treatment comprises all suitable seed treatment and especially seed dressing techniques known in the art, such as seed coating (e.g. seed pelleting), seed dusting and seed imbibition (e.g. seed soaking). Here, "seed treatment" refers to all methods that bring seeds and the arylanilide of formula I into contact with each other, and "seed dressing" to methods of seed treatment which provide the seeds with an amount of the arylanilide of formula I, i.e. which generate a seed comprising the arylanilide of formula I. In principle, the treatment can be applied to the seed at any time from the harvest of the seed to the sowing of the seed. The seed can be treated immediately before, or during the planting of the seed, for example using the "planter's box" method. However, the treatment may also be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed.

Expediently, the treatment is applied to unsown seed. As used herein, the term "unsown seed" is meant to include seed at any period from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant.

When it is said that unsown seed is "treated", such treatment is not meant to include those practices in which the fungicide is applied to the soil, rather than directly to the seed.

By applying the treatment to the seed prior to the sowing of the seed the operation is simplified. In this manner, seeds can be treated, for example, at a central location and then dispersed for planting. This permits the person who plants the seeds to avoid the handling and use of the arylanilide of formula I and to merely handle and plant the treated seeds in a manner that is conventional for regular untreated seeds, which reduces human exposure. In each embodiment of the invention, it is preferred that the arylanilide of formula I is applied to a seed in an effective amount, that is, an amount sufficient to provide protection against phytopathogenic fungi to the seed and/or the plant that grows from the seed. As used herein, "protection" is achieved if the percent of damage to the seed and/or the plant at 10 days after infestation (DAI) with the fungus is significantly reduced for treated seeds or plants grown from treated seeds as compared to untreated seeds or plants grown from untreated seeds. In order to be effective, the arylanilide of formula I is generally employed in an amount of from 1 to 500 g, preferably 10 to 200 g, per 100 kilograms of seed.

According to the present invention one purpose of said seed treatment is to control phytopathogenic fungi. Such a seed treatment thus involves a fungicidal effect or a fungicidal activity providing protection against damage done by the fungus to a seed and/or a plant grown from the seed.

As used herein, the terms "fungicidal effect" and "fungicidal activity" mean any direct or indirect action on the target pathogen (which may be any fungus, but includes according to the invention rust infections on leguminous plants and their seed) that results in reduction of damage on the treated seeds as well as on the fruits, roots, shoots and/or foliage of plants grown from treated seeds as compared untreated seeds or to plants grown from untreated seeds, respectively. The terms "active against a (first or second) pathogen" also have the same meaning. Such direct or indirect actions include killing of the fungal pathogen, inhibiting infestation of the fungal pathogen on the plant seeds, fruits, roots, shoots and/or foliage, and inhibiting or preventing reproduction of the fungal pathogen.

The target organisms for the present invention are preferably fungal diseases in leguminous plants, in particular soybeans. The most important fungal pathogens are:

Altemaria, in particular in vegetable, rape, sugar beets, fruits and rice; Sclerotinia, especially Sclerotinia sclerotiorum, in particular in rape and sunflowers;

Sclerotium, especially Sclerotium rolfsii;

Cercospora, especially Cercospora kikuchi and Cercospora sojina, in particular in corn, soy beans, rice and sugar beets;

Colletotrichum, especially Colletotrichum truncatum, in particular in soy beans and cotton;

Corynespora, especially Corynespora casiicola;

Diaporthe, especially Diaporthe phaseolorum;

Microsphaera, especially Microsphaera diffusa;

Phakopsora, especially Phakopsora pachyrhizi and Phakopsora meibomiae, in particular in soy beans; Pyrenophora, especially Pyrenophora graminea, Pyrenophora teres, Pyrenophora, in particular in cereals;

Rhizoctonia, especially Rhizoctonia solani, in particular in rice, cotton, potatoes, lawn, corn, rape, sugar beets and vegetables; Septoria, especially Septoria glycines and Septoria tritici, in particular in wheat;

Tilletia, especially Tilletia caries, Tilletia controversa, and Tilletia indica, in particular in cereals;

Ustilago, especially Ustilago hordei and Ustilago nuda, in particular in cereals such as corn, and sugar beets.

Phakopsora pachyrhizi and Phakopsora meibomiae are particular target pathogens of the present invention, especially in the treatment of soy beans.

Pyrenophora, Rhizoctonia, Tilletia and Ustilago are particular target pathogens of the present invention, especially in the treatment of cereals, preferably rice.

The present seed treatment can be used to control said target pests and/or to protect the seeds, roots and/or the above-ground parts of field, forage, plantation, glasshouse, orchard or vineyard crops, ornamentals, plantation or forest trees and/or any other plant(s) of interest. The seeds that are useful in the present invention can be the seeds of any plant species.

As used herein, ingredients comprise active ingredients and auxiliary agents.

In the present invention, an "active ingredient" is a compound or a combination of compounds which directly exerts a biologically relevant effect, preferably a fungicidal effect as described above.

To widen the spectrum of action, the active ingredient, i.e. the arylanilide of formula I, can also be employed together with other active ingredients which are useful in seed treatment, for example together with fungicides, insecticides, moiluscicides, nematicides, herbicides, algicides, bactericides, rodenticides, bird/mammal repellents, growth regulators, or also fertilizers.

The following list of active ingredients with which the arylanilide of formula I can be used in accordance with the invention is intended to illustrate the possible combinations, but not to impose any limitation: • Fungicides:

• azoles such as bromoconazole, cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, and triticonazole;

• acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace and oxadixyl; • amine derivatives such as guazatine;

• anilinopyrimidines such as pyrimethanil, mepanipyrim and cyprodinil;

• dicarboximides such as iprodione, procymidone, vinclozolin;

• dithiocarba mates such as mancozeb, metiram and thiram;

• heterocylic compounds such as benomyl, carbendazim, carboxin, oxycarboxin, fuberidazole, picobenzamid, penthiopyrad, proquinazid, thiabendazole and thiophanate-methyl;

• phenylpyrroles such as fenpiclonil and fludioxonil;

• other fungicides, for example benthiavalicarb, cyflufenamid, fosetyl, fosetyl- aluminum, phosphorous acid and its salts, iprovalicarb and metrafenone; • strobilurins such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxastrobin, kresoxim-methyl, rπetominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)- ethyl]benzyl)carbamate, methyl (2-chloro-5-[1 -(6-methylpyridin-2-ylmethoxy- imino)ethyl]benzyl)carbamate and methyl 2-ortho-[(2,5-dimethylphenyloxy- methylene)phenyl]-3-methoxyacrylate;

• cinnamides and analogous compounds such as dimethomorph, flumetover and flumorph;

• Insecticides/acaricides: • organo(thio)phosphates such as acephate, diazinon, malathion, methyl- parathion, profenofos, sulprofos and terbufos;

• carbamates such as methomyl, thiodicarb and fenothiocarb;

• pyrethroids such as cyfluthrin, cyhalothrin, cypermethrin, ethofenprox, permethrin and silafluofen; • nicotinic receptor agonists/antagonists such as imidacloprid, thiamethoxam, nitenpyram and acetamiprid;

• GABA antagonists such as endosulfan and fipronil;

• macrocyclic lactone insecticides such as abamectin, emamectin, milbemectin, nemamectin, moxidectin and spinosad; • formamides such as amitraz, chlordimeform, hydramethylnon and chlorfenamidine;

• uncouplers such as chlorfenapyr;

• Molluscicides; Nematicides; • Herbicides, for example imidazolinone herbicides such as imazethapyr, imazamox, imazapyr and imazapic, or dimethenamid-p;

• Algicides;

• Bactericides; • Biologicals (natural products);

• Bird / mammal repellents;

• Fertilizers;

• Fumigants;

• Growth regulators; • Rodenticides.

Molluscicides, nematicides, herbicides, algicides, bactericides, biologicals, bird / mammal repellents, fertilizers, fumigants, growth regulators and rodenticides are well known to a person skilled in the art.

According to a particular embodiment, the arylanilides of formula I are used in combination with an azole fungicide. Azole fungicides include triazole and imidazole fungicides including the conazole fungicides or triazolopyrimidine fungicides. Triazole and imidazole fungicides , their preparation and their action against harmful fungi are generally known (cf.: http://www.alanwood.net/pesticides/class_fungicides.html). They are commercially available. Examples of triazole fungicides include: Amisulbrom, bitertanol, fluotrimazole, triazbutil and the conazole fungicides azaconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole including diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinazole, flusilazole, furconazole including furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, penconazole, propiconazole, prothioconazole, quinconazole, simeconazole, tebuconazole, tetraconazole, triticonazole, uniconazole, including uniconazole P.

Examples of imidazole fungicides are cyazofamide, fenamidone, fenapanil, glyodin, iprodione, isovaledione, pefurazoate, triazoxide, prochloraz, and triflumizol.

Suitable triazolopyrimidine fungicides are for example disclosed in WO 02/15697, the content of which is being made part of the present invention.

Preferred azole fungicides are epoxiconazole, metconazole, fluquinconazole, flutriafole, ipconazole, prothioconazole or triticonazole. In combination with azole fungicides the use of compounds Ia.1 , Ia.2, Ia.23, Ia.24, Ia.25 and Ia.26 is particularly preferred. According to another particular embodiment, the arylanilides of formula I are used in combination with an insecticide, in particular fipronil, or a neonicotinoid such as acetamiprid, clothianidine, dinotefuran, imidaclobrid, nitenpyram, tiacloprid or thiamethoxam.

According to a further embodiment, the arylanilides of formula I are used in combination with a strobilurin as defined above, in particular pyraclostrobin and an azole fungicide as defined above, in particular epoxiconazole or triticonazole.

According to another particular embodiment , the arylanilides of formula I are used in combination with a triazolopyrimidine as defined above, in particular 5-chloro-7-(4- methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo-[1 ,5-a]pyrimidine and a triazole fungicide as defined above, in particular epoxiconazole or triticonazole.

If the arylanilides of formula I are employed jointly with a further active ingredient, especially with an azole fungicide and/or an insecticide, in particular fipronil, the ratio by weight of the arylanilides of formula I to the amount of the further active ingredient(s) is usually in the range of 1 :100 to 100:1 , preferably in the range of 1 :50 to 50:1 , and in particular in the range of 1 : 10 to 10: 1.

If an arylanilide of formula I is employed jointly with a further active ingredient, the latter can be applied simultaneously with the arylanilide of formula I or after a short time interval, for example within a few days before or after the treatment with the arylanilide of formula I. In the case of simultaneous application, the treatment of the seed can be effected in one pass where a composition comprising the arylanilides of formula I and the further active ingredient is applied, or else in separate passes where different formulations of the individual active ingredients are applied.

The active ingredient concentrations in ready-to-use preparation can be varied within substantial ranges. In general, they are between in the range from 0.01 and 80% by weight, frequently in the range from 0.1 to 50 % by weight, preferably in the range from 0.5 and 20% by weight, based on the total weight of the preparation. The active ingredients can also successfully be used in concentrated form, it being possible to apply, to the seed, preparations with more than 80% by weight of active ingredient, or even the active ingredient without additions. The amount of additives will generally not exceed 30% by weight, preferably 20% by weight, and is, in particular, in the range of from 0.1 to 20% by weight, in each case based on the total weight of the preparation.

In principle, all customary methods of treating and in particular dressing such as coating (e.g. pelleting) and imbibing (e.g. soaking) seeds can be employed. Specifically, the seed treatment follows a procedure in which the seed is exposed to the specifically desired amount of a preparation comprising the arylanilide of formula I. The preparation may be a formulation that is applied as such or after previously diluting it, e.g. with water; for instance, it may be expedient to dilute seed treatment formulations 2-10 fold leading to concentrations in the ready-to-use compositions of 0.01 to 60% by weight active compound by weight, preferably 0.1 to 40% by weight. Usually, a device which is suitable for this purpose, for example a mixer for solid or solid/liquid components, is employed until the preparation is distributed uniformly on the seed. Thus, the preparation can be applied to seeds by any standard seed treatment methodology, including but not limited to mixing in a container (e.g., a bottle, bag or tumbler), mechanical application, tumbling, spraying, and immersion. If appropriate, this is followed by drying.

Particular embodiments of the present invention comprise seed coating and imbibition (e.g. soaking). "Coating" denotes any process that endows the outer surfaces of the seeds partially or completely with a layer or layers of non-plant material, and "imbibition" any process that results in penetration of the active ingredient(s) into the germinable parts of the seed and/or its natural sheath, (inner) husk, hull, shell, pod and/or integument. The invention therefore also relates to a treatment of seeds which comprises providing seeds with a coating that comprises an arylanilide of formula I, and to a treatment of seeds which comprises imbibition of seeds with an arylanilide of formula I.

Coating is particularly effective in accommodating high loads of the arylanilide of formula I, as may be required to treat typically refractory fungal pathogens, while at the same time preventing unacceptable phytotoxicity due to the increased load of the arylanilide of formula I.

Coating may be applied to the seeds using conventional coating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods such as the spouted beds technique may also be useful. The seeds may be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing.

Such procedures are known in the art. Seed coating methods and apparatus for their application are disclosed in, for example, US 5,918,413, US 5,891,246, US 5,554,445, US 5,389,399, US 5,107,787, US 5,080,925, US 4,759,945 and US 4,465,017.

In another particular embodiment, the solid the arylcarboxylic acid biphenylamide of formula I, for instance as a solid fine particulate formulation, e.g. a powder or dust, can be mixed directly with seeds. Optionally, a sticking agent can be used to adhere the solid, e.g. the powder, to the seed surface. For example, a quantity of seed can be mixed with a sticking agent (which increases adhesion of the particles on the surface of the seed) and optionally agitated to encourage uniform coating of the seed with the sticking agent. For example, the seed can be mixed with a sufficient amount of sticking agent, which leads to a partial or complete coating of the seed with sticking agent. The seed pretreated in this way is then mixed with a solid formulation containing the arylanilide of formula I to achieve adhesion of the solid formulation on the surface of the seed material. The mixture can be agitated, for example by tumbling, to encourage contact of the sticking agent with the solid arylanilide, thereby causing the solid arylanilide I to stick to the seed.

Another particular method of treating seed with the arylanilide of formula I is imbibition. For example, seed can be combined for a period of time with an aqueous solution comprising from about 1 % by weight to about 75% by weight of the arylanilide of formula I in a solvent such as water.

Preferably the concentration of the solution is from about 5% by weight to about 50% by weight, more preferably from about 10% by weight to about 25% by weight. During the period in which the seed is combined with the solution, the seed takes up (imbibes) at least a portion of the arylanilide of formula I.

Optionally, the mixture of seed and solution can be agitated, for example by shaking, rolling, tumbling, or other means. After the imbibition process, the seed can be separated from the solution and optionally dried in a suitable manner, for example by patting or air-drying.

In yet another particular embodiment of the present invention, the arylanilide of formula I can be introduced onto or into a seed by use of solid matrix priming. For example, a quantity of the arylanilide of formula I can be mixed with a solid matrix material, and then the seed can be placed into contact with the solid matrix material for a period to allow the arylanilide of formula I to be introduced to the seed. The seed can then optionally be separated from the solid matrix material and stored or used, or, preferably, the mixture of solid matrix material plus seed can be stored or planted/sown directly.

As described above, the arylanilide of formula I and optionally the further active ingredient(s) can be used as such, that is, without any auxiliary agents present. However, the arylanilide of formula I and the further active ingredient(s) are typically applied to the seeds in the form of a composition. As used herein, a "composition" comprises at least one active ingredient and at least one auxiliary agent.

The term "auxiliary agent" refers to a compound or combination of compounds which do not exert a biologically relevant effect of their own, but support the effects of the active ingredient(s). When auxiliary agents are used, their choice will depend on the active ingredients and on the procedures selected for seed treatment.

Usually, the compositions thus comprise an active ingredient component ("A") and an auxiliary agent component ("B"). The active ingredient component ("A") of the composition comprises the arylanilide of formula I ("A1") and optionally one or more further active ingredient(s) ("A2"). The auxiliary agent component ("B") comprises one or more auxiliary agent(s).

In general, the compositions comprise from 0.005% by weight to 95% by weight, preferably from 0.1 % by weight to 90% by weight, in particular from 5% by weight to 50% by weight, of the active ingredient component "A", the balance being formed by component "B". In this context, the active ingredients are employed in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum). According to a particular embodiment, component "A" essentially consists of the arylanilide of formula I, i.e. the active ingredient of the composition is the arylanilide of formula I.

In a particular embodiment of the invention, the composition may additionally comprise one or more repellents for warm-blooded animals, e.g. birds, dogs and hedgehogs, for example nonanoic acid vanillyl amide. The amount of repellent will preferably range from 0.1 to 5 % by weight, based on the total weight of the composition.

According to a particular embodiment, the composition is a seed treatment formulation. A seed treatment formulation according to the present invention comprises at least one auxiliary agent that is specifically suited for the seed treatment, i.e. an auxiliary agent which in particular promotes adhesion of the arylanilide of formula I to and/or penetration into the seeds and/or otherwise improves stability and/or manageability of the composition or the seeds treated therewith. Thus, the present invention also relates to a seed treatment formulation, which comprises the arylanilide of formula I, at least one seed treatment auxiliary agent(s), and optionally one or more further auxiliary agents.

In particular, seed treatment auxiliary agents are selected from the group consisting of agents suitable for seed coating materials, agents suitable for solid matrix priming materials, penetration enhancers suitable for promoting seed imbibition, colorants, antifreezes, and gelling agents.

According to a preferred embodiment, the seed coating material comprises a binder (or sticker). Optionally, the coating material also comprises one or more additional seed treatment auxiliary agents selected from the group consisting of fillers and plasticizers.

Binders (or stickers) are all customary binders (or stickers) which can be employed in seed treatment formulations. Binders (or stickers) that are useful in the present invention preferably comprise an adhesive polymer that may be natural or partly or wholly synthetic and is without phytotoxic effect on the seed to be coated. Preferably, the binder (or sticker) is biodegradable. Preferably the binder or sticker is chosen to act as a matrix for the arylanilide of formula I.

The binder (or sticker) may be selected from polyesters, polyether esters, polyanhydrides, polyester urethanes, polyester amides; polyvinyl acetates; polyvinyl acetate copolymers; polyvinyl alcohols and tylose; polyvinyl alcohol copolymers; polyvinylpyrolidones; polysaccharides, including starches, modified starches and starch derivatives, dextrins, maltodextrins, alginates, chitosanes and celluloses, cellulose esters, cellulose ethers and cellulose ether esters including ethylcelluloses, methylcelluloses, hydroxymethylcelluloses, hydroxypropylcelluloses and carboxymethylcellulose; fats; oils; proteins, including casein, gelatin and zeins; gum arabics; shellacs; vinylidene chloride and vinylidene chloride copolymers; lignosulfonates, in particular calcium lignosulfonates; polyacrylates, polymethacrylates and acrylic copolymers; polyvinylacrylates; polyethylene oxide; polybutenes, polyisobutenes, polystyrene, polyethyleneamines, polyethylenamides; acrylamide polymers and copolymers; polyhydroxyethyl acrylate, methylacrylamide monomers; and polychloroprene. In a particular embodiment, the binder is a thermoplastic polymer.

In a particular embodiment of the invention the seed treatment formulation contains at least one polyester, which, in particular, is selected from polylactides, partially aromatic polyesters (copolymers of terephthalic acid, adipic acid and aliphatic diols), polyglycolides, polyhydroxyalkanoates and polytartrates.

The amount of binder (or sticker) in the formulation can vary, but will be in the range of about 0.01 to about 25% of the total weight, more preferably from about 1 to about 15%, and even more preferably from about 5 % to about 10%.

As mentioned above, the coating material can optionally also comprise a filler. The filler can be an absorbent or an inert filler, such as are known in the art, and may include wood flours, cereal flours, tree bark mill, wood meal and nut shell meal, sugars, in particular polysaccharides, activated carbon, fine-grain inorganic solids, silica gels, silicates, clays, chalk, diatomaceous earth, calcium carbonate, magnesium carbonate, dolomite, magnesium oxide, calcium sulfate and the like. Clays and inorganic solids which may be used include calcium bentonite, kaolin, china clay, talc, perlite, mica, vermiculite, silicates, quartz powder, montmorillonite, attapulgite, bole, loess, limestone, lime and mixtures thereof. Sugars which may be useful include dextrin and maltodextrin. Cereal flours include wheat flour, oat flour and barley flour. The filler may also comprise fertilizer substances such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and mixtures thereof.

The filler is selected so that it will provide a proper microclimate for the seed, for example the filler is used to increase the loading rate of the active ingredients and to adjust the control-release of the active ingredients. The filler can aid in the production or process of coating the seed. The amount of filler can vary, but generally the weight of the filler components will be in the range of about 0.05 to about 75% of the total weight, more preferably about 0.1 to about 50%, and even more preferably about 0.5% to 15%.

It is preferred that the binder (or sticker) be selected so that it can serve as a matrix for the arylanilide of formula I. While the binders disclosed above may all be useful as a matrix, it is preferred that a continuous solid phase of one or more binder compounds is formed throughout which is distributed as a discontinuous phase the arylanilide of formula I. Optionally, a filler and/or other components can also be present in the matrix. The term "matrix" is to be understood to include what may be viewed as a matrix system, a reservoir system or a microencapsulated system. In general, a matrix system consists of the arylanilide of formula I and a filler uniformly dispersed within a polymer, while a reservoir system consists of a separate phase comprising the arylanilide of formula I or its salt that is physically dispersed within a surrounding, rate-limiting, polymeric phase. Microencapsulation includes the coating of small particles or droplets of liquid, but also to dispersions in a solid matrix.

Especially if the arylanilide of formula I used in the coating is an oily type composition and little or no inert filler is present, it may be useful to hasten the drying process by drying the composition. This optional step may be accomplished by means well known in the art and can include the addition of calcium carbonate, kaolin or bentonite clay, perlite, diatomaceous earth, or any absorbent material that is added preferably concurrently with the arylanilide of formula I coating layer to absorb the oil or excess moisture. The amount of absorbent necessary to effectively provide a dry coating will be in the range of about 0.5 to about 10% of the weight of the seed. Optionally, the coating material comprises a plasticizer. Plasticizers are typically used to make the film that is formed by the coating layer more flexible, to improve adhesion and spreadability, and to improve the speed of processing. Improved film flexibility is important to minimize chipping, breakage or flaking during storage, handling or sowing processes. Many plasticizers may be used; however, useful plasticizers include polyethylene glycol, oligomeric polyalkylene glycols, glycerol, alkylbenzylphthalates, in particular butylbenzylphthalate, glycol benzoates and related compounds. The amount of plasticizer in the coating layer will be in the range of from about 0.1 % by weight to about 20% by weight.

Agents suitable for solid matrix priming materials which are useful in the present invention include polyacrylamide, starch, clay, silica, alumina, soil, sand, polyurea, polyacrylate, or any other material capable of absorbing or adsorbing the arylanilide of formula I for a time and releasing that arylanilide of formula I into or onto the seed. It is useful to make sure that the arylanilide of formula I and the solid matrix material are compatible with each other. For example, the solid matrix material should be chosen so that it can release the arylanilide of formula I at a reasonable rate, for example over a period of minutes, hours, or days.

Penetration enhancers suitable for promoting seed imbibition include agriculturally acceptable surface active compounds. The amount of penetration enhancers will usually not exceed 20% by weight, based on the total weight of the formulation. Preferably, the amount of penetration enhancers will be in the range from 2% to 20% by weight.

Colorants according to the invention are all dyes and pigments which are customary for such purposes. In this context, both pigments, which are sparingly soluble in water, and dyes, which are soluble in water, may be used. Examples which may be mentioned are the colorants, dyes and pigments known under the names Rhodamin B, C. I. Pigment Red 112 and C. I. Solvent Red 1 , Pigment Blue 15:4, Pigment Blue 15:3, Pigment Blue 15:2, Pigment Blue 15:1 , Pigment Blue 80, Pigment Yellow 1 , Pigment Yellow 13, Pigment Red 48:2, Pigment Red 48:1 , Pigment Red 57:1 , Pigment Red 53:1 , Pigment Orange 43, Pigment Orange 34, Pigment Orange 5, Pigment Green 36, Pigment Green 7, Pigment White 6, Pigment Brown 25, Basic Violet 10, Basic Violet 49, Acid Red 51 , Acid Red 52, Acid Red 14, Acid Blue 9, Acid Yellow 23, Basic Red 10, Basic Red 108. The amount of colorants will usually not exceed 20 % by weight of the formulation and preferably ranges from 1 to 15 % by weight, based on the total weight of the formulation. It is generally preferred if the colorants are also active as repellents for warm-blooded animals, e. g. iron oxide, Tiθ2, Prussian blue, anthraquinone dyes, azo dyes and metal phtalocyanine dyes. Antifreezes which can be employed especially for aqueous formulations are in principle all those substances which lead to a depression of the melting point of water. Suitable antifreezes comprise alcohols such as methanol, ethanol, isopropanol, butanols, glycol, glycerine, diethylenglycol and the like. Typically, the amount of antifreeze will not exceed 20 % by weight and frequently ranges from 1 to 15 % by weight, based on the total weight of the formulation.

Gelling agents which are suitable are all substances which can be employed for such purposes in agrochemical compositions, for example cellulose derivatives, polyacrylic acid derivatives, xanthan, modified clays, in particular organically modified phyllosilicates and highly-dispersed silicates. A particularly suitable gelling agent is carrageen (Satiagel^®). Usually, the amount of gelling agent will not exceed 5 % by weight of the formulation and preferably ranges from 0.5 to 5 % by weight, based on the total weight of the formulation.

Further auxiliary agents that may be present in the seed treatment formulation include solvents, wetters, dispersants, emulsifiers, surfactants, stabilizers, protective colloids, antifoams, and preservatives.

Examples of suitable solvents are water or organic solvents such as aromatic solvents (for example Solvesso^® products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone, N- octyl-pyrrolidone), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used. However, according to a particular embodiment, the formulations of the present invention contain less than 10 % by weight and preferably less than 6 % by weight of said organic solvents.

Surface active compounds are all those surfactants which are suitable for formulating agrochemical actives, in particular for the arylanilide of formula I, and which may be nonionic, cationic, anionic or amphoteric. According to their action, surfactants - sometimes referred to as "additives" - may be divided into wetters, dispersants, emulsifiers or protective colloids; however, these particular groups may overlap and cannot be divided strictly. Typically, the amount of surfactants will not exceed 20 % by weight and frequently ranges from 1 to 15 % by weight, based on the total weight of the formulation. Suitable wetters are all those substances which promote wetting and which are conventionally used for formulating agrochemical active ingredients. Alkylnaphthalenesulfonat.es such as diisopropyl- or diisobutylnaphthalenesulfonat.es can be used preferably.

Dispersants and/or emulsifiers which are suitable are all nonionic, anionic and cationic dispersants or emulsifiers conventionally used for formulating agrochemical active ingredients. The following can preferably be used: nonionic or anionic dispersants and/or emulsifiers or mixtures of nonionic or anionic dispersants and/or emulsifiers.

Suitable nonionic dispersants and/or emulsifiers which may be employed are, in particular, ethylene oxide/alkylene oxide block copolymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers, for example polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl- polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters and methyl cellulose. However, according to a particular embodiment, the formulations of the present invention contain less than 10 % by weight and preferably less than 6 % by weight of ethylene oxide/alkylene oxide block copolymer, and, more particularly, less than 10 % by weight and preferably less than

6 % by weight of said nonionic dispersants and/or emulsifiers.

Suitable anionic dispersants which and/or emulsifiers which may be employed are, in particular, alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkyl- arylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore arylsulfonate/formaldehyde condensates, for example condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, ligninsulfonates, lignin-sulfite waste liquors, phosphated or sulfated derivatives of methylcellulose, and salts of polyacrylic acid.

Protective colloids are typically water soluble, amphiphilic polymers. Examples include proteins und denatured proteins such as casein, polysaccharides such as water soluble starch derivatives and cellulose derivatives, in particular hydrophobic modified starch and celluloses, furthermore polycarboxylates such as polyacrylic acid and acrylic acid copolymers, polyvinylalcohol, polyvinylpyrrolidone, vinylpyrrolidone copolymers, polyvinyl amines, polyethylene imines and polyalkylene ethers. Antifoams which can be employed are all those substances which inhibit the development of foam and which are conventionally used for formulating agrochemical active ingredients. Silicone antifoams, i.e. aqueous silicon emulsions (e.g. Silikon^® SRE by Wacker or Rhodorsil^® by Rhodia), long chain alcohols, fatty acids and salts thereof, e.g. and magnesium stearate are particularly suitable. Usually, the amount of antifoam will not exceed 3 % by weight of the formulation and preferably ranges from 0.1 to 2 % by weight, based on the total weight of the formulation.

Preservatives which can be employed are all preservatives used for such purposes in agrochemical compositions. Examples which may be mentioned are dichlorophene, isothiazolenes and isothiazolones such as 1 ,2-benzisothiazol-3(2H)-one, 2-methyl-2H- isothiazol-3-one-hydrochloride, 5-chloro-2-(4-chlorobenzyl)-3(2H)-isothiazolone, 5- chloro-2-methyl-2H-isothiazol-3-one, 5-chloro-2-methyl-2H-isothiazol-3-one, 5-chloro-2- methyl-2H-isothiazol-3-one-hydrochloride, 4,5-dichloro-2-cyclohexyl-4-isothiazolin-3- one, 4,5-dichloro-2-octyl-2H-isothiazol-3-one, 2-methyl-2H-isothiazol-3-one, 2-methyl- 2H-isothiazol-3-one-calcium chloride complex, 2-octyl-2H-isothiazol-3-one and benzyl alcohol hemiformal. Usually, the amount of preservatives will not exceed 2 % by weight of the formulation and preferably ranges from 0.01 to 1 % by weight, based on the total weight of the formulation.

The skilled person is essentially familiar with agricultural compositions of active ingredients. Examples include water-soluble concentrates (SL, LS), dispersible concentrates (DC), emulsifiable concentrates (EC), emulsions (EW, EO, ES), suspensions (SC, OD, FS), water-dispersible granules (WG, SG), water-dispersible or water-soluble powders (WP, SP, SS, WS), dusts or dustable powders (DP, DS), granules (GR, FG, GG, MG), ULV solutions (UL) and gel formualtions (GF). The skilled worker is familiar with such compositions, for example from Ullmann's Encyclopedia of Industrial Chemistry, Fungicides Chapter 4, 5th ed. on CD-ROM, Wiley- VCH, 1997 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH,

Weinheim (Federal Republic of Germany), 2001. For seed treatment purposes, such compositions may be applied as such or after addition of a suitable liquid, in particular water, in order to dissolve, emulsify, disperse, supend or dilute the composition. The type of the ready-to-use preparation applied to the seeds thus depends on the type of composition used and the method used for treating the seeds.

Such compositions can be prepared in the known manner (see e.g. for review US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and et seq. WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701 , US 5,208,030, GB 2,095,558, US 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961 , Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001 , 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8)), for example by extending the active ingredient component with one ore more auxiliary agents.

The folowing examples simply illustrate said compositions:

A Water-soluble concentrates, solutions (SL, LS)

10 parts by weight of an arylanilide I are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added to the arylanilide of formula I. The arylanilide of formula I dissolves upon dilution with water, whereby a formulation with 10 % (w/w) of the arylanilide I is obtained.

B Dispersible concentrates (DC)

20 parts by weight of an arylanilide I are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of the arylanilide I is obtained.

C Emulsifiable concentrates (EC) 15 parts by weight of an arylanilide I are dissolved in 7 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of the arylcarboxylic acid biphenylamide I is obtained.

D Emulsions (EW, EO, ES)

25 parts by weight of an arylanilide I are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of the arylanilide I is obtained.

E Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of an arylanilide I are comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the arylanilide I, whereby a formulation with 20% (w/w) of the arylanilide I is obtained.

F Water-dispersible granules (WG₁ SG)

50 parts by weight of an arylanilide I are ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 50% (w/w) of the arylanilide I is obtained.

G Water-dispersible and water-soluble powders (WP, SP, SS, WS) 75 parts by weight of an arylanilide I are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of the arylanilide I is obtained.

H Dusts and dustable powders (DP, DS)

5 parts by weight of an arylanilide I are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of the arylanilide I.

J Granules (GR, FG, GG, MG),

0.5 part by weight of an arylanilide I is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of the arylanilide I is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.

K ULV solution (UL) 10 parts by weight of an arylanilide I are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of the arylanilide I, which is applied undiluted for foliar use.

L Gel formulation (GF) In an agitated ball mill, 20 parts by weight of an arylanilide I are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the arylanilide I, whereby a formulation with 20% (w/w) of the arylanilide I is obtained. For the seed treatment according to the present invention, powders, such as water- dispersible, water-soluble and dustable powders, dusts and suspensions are preferred. Further, gel formulations are preferred. Also, water-soluble concentrates and emulsions may be expediently used. According to the present invention, the following formulations are particularly preferred: flowable concentrates (especially FS); solutions (especially LS); powders for dry treatment (especially DS); water dispersible powders for slurry treatment (especially WS); water-soluble powders (especially SS) and emulsions (especially ES). Also preferred are gel formulations (especially GF). These formulations can be applied to the seed diluted or undiluted.

According to a particular embodiment, a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1-800 g/l of an arylanilide I, 1-200 g/l surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a colorant and up to 1 liter of a solvent, preferably water.

According to a further particular embodiment, the seed treatment formulation of the present invention is a seed coating formulation.

Such seed coating formulations comprise an arylanilide I₁ at least one binder (or sticker) and optionally at least one further auxiliary agent that is selected from the group consisting of fillers and plasticizers.

Seed coating formulations comprising binders, fillers and/or plasticizers are well-known in the art. Seed coating formulations are disclosed, for example, in US 5,939,356, US 5,882,713, US 5,876,739, US 5,849,320, US 5,834,447, US 5,791 ,084, US 5,661,103, US 5,622,003, US 5,580,544, US 5,328,942, US 5,300,127, US 4,735,015, US 4,634,587, US 4,383,391 , US 4,372,080, US 4,339,456, US 4,272,417 and US 4,245,432, among others.

The amount of the arylanilide of formula I that is included in the coating formulation will vary depending upon the type of seed, but the coating formulation will contain an amount of arylanilide I that is fungicidally effective. In general, the amount of arylanilide I in the coating formulation will range from about 0.005 to about 75% of the total weight. A more preferred range for the arylanilide I is from about 0.01 to about 40%; more preferred is from about 0.05 to about 20%.

The exact amount of the arylanilide I that is included in the coating formulation is easily determined by one skilled in the art and will vary depending upon the size and other characteristics (surface structure etc.) of the seed to be coated. The arylanilide I of the coating formulation must not inhibit germination of the seed and should be efficacious in protecting the seed and/or the plant during that time in the target pathogen's life cycle in which it causes injury to the seed or plant. In general, the coating will be efficacious for approximately 0 to 120 days, preferably for approximately 0 to 60 days, after sowing. The coating formulations formed with the arylanilide I are capable of effecting a slow rate of release of the arylanilide I by diffusion or movement through the matrix into the seed or to the surrounding medium.

The present invention also provides a seed that has been treated by the method described above. It also provides a seed obtainable by the method described above.

Further, the present invention also provides a seed that has been treated with a seed treatment formulation described above, and in particular that is coated with the formulation or contains it. It also provides a seed obtainable by using the formulation described above.

The term "coated with and/or contains" here signifies that the arylanilide I is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the arylanilide I may penetrate into the seed, depending on the method of application. When the said seed is (re)planted, it may absorb the arylanilide I.

Still further, the present invention relates to a seed, especially an unsown seed, which comprises an arylanilide of formula I.

According to one embodiment, such a seed comprising an arylanilide of formula I has a coating, wherein the coating comprises the arylanilide I.

According to a further embodiment, such a seed comprising the arylanilide I is a seed whose germinable part and/or natural sheath, shell, pod and/or integument comprise(s) the arylanilide I. Also, the arylanilide I can be present in both the coating and the germinable part and/or natural sheath, shell, pod and/or integument of the seed.

Preferably, such seeds comprise an effective amount of the arylanilide I. Accordingly, the seeds are coated, impregnated or coated and impregnated in such a manner that damage during germination and emergence is reduced.

The seeds treated with an arylanilide of formula I may also be enveloped with a film overcoating to protect the arylanilide I coating. Such overcoatings are known in the art and may be applied using conventional fluidized bed and drum film coating techniques. The seeds of the present invention can be used for the propagation of plants. The seeds can be stored, handled, planted/sowed and tilled.

Unless indicated otherwise, all amounts in % by weight refer to the weight of the total composition (or formulation).

Example - Activity towards Rhizoctoπia solani\r\ vitro

The test compounds were dissolved in DMSO to give a stock solution of 10.000 ppm active substance. The stock solutions were diluted to the test concentrations with YBA (yeast extract-bacto peptone-sodium acetate) broth. Agar plugs of mycelium of Rhizoctonia so/an/were added as inoculum. Incubation followed at 23°C. Evaluation of mycelial growth was made after 72 hrs. with the aid of a dissecting microscope (x 100). The results are given in the following table:

Results of the application example

Table 5

Compound no. concentration inhibition of mycelial growth

(ppm) no weak strong complete

Control X

125 X la.2 32 X

8 X

0,25 X

125 X la.24 32 X

8 X

0,25 X

125 X la.27 35 X

8 X

0,25 X

Claims

A method of seed treatment, which comprises treating a seed with an effective amount of an arylanilide of the formula I

wherein

X is halogen; Y is oxygen or sulfur; n is zero, 1 , 2, 3 or 4;

R is Ci-Cβ-alkyl, CrC₈-haloalkyl, C₂-C8-alkenyl, C₂-C₈-haloalkenyl, C₃-C₈- cycloalkyl or C3-C₈-cycloalkenyl; Ar is an aryl radical of the formula Ha, Mb or Mc

"a: _R4A_Nk_R5 "b: l_zl_R6 Hc,

wherein

R¹ is hydrogen, halogen, CrC₄-alkyl or CrC₄-haloalkyl;

R² is Ci-C₄-alkyl;

R³ is hydrogen, halogen or methyl; R⁴ is hydrogen, halogen, CrC₄-alkyl, or Ci-C₄-haloalkyl;

R⁵ is CrC₄-alkyl or d-C₄-haloalkyl;

Z is CH or N and

R⁶ is halogen, CrC₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy, Ci-C₄-alkylthio,

Ci-C₄-alkylsulfinyl or Ci-C₄-alkylsulfonyl.

2. The method according to claim 1 , wherein in formula I

X is halogen;

Y is oxygen; n is zero, 1, 2, 3 or 4;

R is CrCe-haloalkyl or C₂-C6-haloalkenyl;

Ar is an aryl radical of the formula Ha, Mb or Mc

wherein

R¹ is CrC₄-alkyl or Ci-C₄-haloalkyl; R² is CH₃;

R³ is hydrogen or halogen;

R⁴ is Ci-C₄-alkyl or CrC₄-haloalkyl;

R⁵ is Ci-C₄-alkyl or Ci-C₄-haloalkyl;

R⁶ is halogen, Ci-C₄-alkyl or Ci-C₄-haloalkyl, CrC₄-alkoxy, CrC₄-alkylthio, Ci- C₄-sulfinyl or Ci-C₄-alkylsulfonyl; and

Z is N.

3. The method according to claim 1 , wherein in formula I

X is halogen;

Y is oxygen; n is 0 or 3;

R is C₂-C₄-haloalkyl;

Ar is an aryl radical of the formula Ma, Mb or Mc

wherein

R¹ is Ci-C₄-alkyl or Ci-C₄-haloalkyl; R² is CH₃;

R³ is hydrogen or halogen;

R⁴ is CrC₄-alkyl;

R⁵ is Ci-C₄-alkyl or Ci-C₄-haloalkyl;

R⁶ is halogen, Ci-C₄-alkyl or Ci-C₄-haloalkyl; and Z is N.

4. The method according to any one of claims 1 to 3, wherein Ar is an aryl radical of the formula Ha.

5. The method according to any one of claims 1 to 3, wherein Ar is an aryl radical of the formula lib.

6. The method according to any one of claims 1 to 3, wherein Ar is an aryl radical of the formula Mc with X being N.

7. The method according to any one of claims 1 to 3, wherein Ar is an aryl radical of the formula Hc with X being CH.

8. A method of seed treatment, which comprises treating a seed with an effective amount of an arylanilide of the formula I according to any one of claims 1 to 7, together with at least one fungicidal active ingredient, selected from

^• azoles such as bromoconazole, cyproconazole, difenoconazole, epoxyconazole, fluquinconazole, flusilazole, flutriafole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol and triticonazole;

• acylalanine such as benalaxyl, metalaxyl, mefenoxam, ofurace and oxadixyl;

• amine derivatives such as guazatine; • anilinopyrimidines such as pyrimethanil, mepanipyrim and cyprodinil;

• dicarboximides such as iprodione, procymidone and vinclozolin;

• dithiocarbamates such as mancozeb, metiram and thiram;

• heterocyclic compounds such as benomyl, carbendazim, carboxin, oxycarboxin, fuberidazole, picobenzamide, penthiopyrad, proquinazide, thiabendazole and thiophanate-methyl;

• phenylpyrroles such as fenpiclonil and fludioxonil;

• other fungicides, for example benthiavalicarb, cyflufenamide, fosetyl, fosetyl- aluminium, phosphoric acid and its salts, iprovalicarb, metrafenone and 5- chloro-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5- ajpyrimidine;

• strobilurines such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methyl-benzyloxy- imino)-ethyl]-benzyl)-carbamate, methyl (2-chloro-5-[1 -(6-methyl-pyridin-2- ylmethoxyimino)-ethyl]-benzyl)-carbamate and methyl 2-ortho-[(2,5-dimethyl- phenyl-oxymethylen)phenyl]-3-methoxy-acrylate;

• zinnamic acid amides and analogous such as dimethomorph, flumetover and flumorph.

9. A method of seed treatment, which comprises treating a seed with an effective amount of an arylanilide of the formula I according to any one of claims 1 to 7, together with at least one insecticidal active ingredient, selected from fipronil, imidacloprid, acetamipird, nitenpyram, carbofuran, carbosulfan, benfuracarb, thiacloprid, clothianidin, MTI 446 and CGA 293343.

10. The method according to any one of claims 1 to 9, wherein the treatment is for controlling phytopathogenic fungi.

11. The method according to claim 10, wherein the phytopathogenic fungus is of the genus Alternaria, Sclerotinia, Sclerotium, Cercospora, Colletrichum, Corynespora, Diaporthe, Microsphaera, Phakopsora or Septoria.

12. The method according to claim 10, wherein the phytopathogenic fungus is of the genus Pyrenophora, Rhizoctonia, Tilletia or Ustilago.

13. The method according to claim 12, wherein the phytopathogenic fungus is

Pyrenophora graminea, Pyrenophora teres, Rhizoctonia solani, Tilletia caries, Tilletia controversa, Tilletia indica, Ustilago hordei or Ustilago nuda.

14. The method according to any one of claims 1 to 13, wherein the seed is of a tuberous or corn vegetable, a leafy vegetable, a leafy brassica green, or a fruiting vegetable.

15. The method according to any one of claims 1 to 13, wherein the seed is of a leguminous plant.

16. The method according to claim 15, wherein soy seed is treated to provide protection against Phakopsora pachyrhizi or Phakopsora meibomiae.

17. The method according to anyone of claims 1 to 13, wherein the seed is of a cereals plant.

18. The method according to claim 16, wherein the cereals plant is rice or wheat plant.

19. The method according to claim 16, wherein rice seed is treated to provide protection against Rhizoctonia solani.

20. The method according to any one of claims 1 to 19, wherein the effective amount of arylanilide of formula I is from 1 to 500 g per 100 kilograms of seed.

21. The method according to any one of claims 1 to 20, where the treatment is seed dressing.

22. A seed treatment formulation comprising an arylanilide of the formula I according to any one of claims 1 to 7 and at least one seed treatment auxiliary agent.

23. The formulation according to claim 22, which comprises between 0.005% by weight and 95% by weight of the arylanilide I.

24. The formulation according to claim 22 or 23, wherein the formulation comprises at least one fungicidal active ingredient, selected from the group

• azoles such as bromoconazole, cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol and

Miconazole;

• acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace and oxadixyl;

• aminderivates such as guazatine;

• anilinopyrimidines such as pyrimethanil, mepanipyrim and cyprodinil; • dicarboximides such as iprodione, procymidon and vinclozolin;

• dithiocarbamates such as mancozeb, metiram and thiram;

• heterocyclic compounds such as benomyl, boscalide, carbendazim, carboxin, oxycarboxin, fuberidazol, picobenzamid, penthiopyrad, proquinazid, thiabendazole and thiophanate-methyl; • phenylpyrroles such as fenpiclonil and fludioxonil;

• other fungicides, for example benthiavalicarb, cyflufenamide, fosetyl, fosetyl- aluminium, phosphoric acid and its salts, iprovalicarb, metrafenone and 5- chloro-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5- ajpyrimidine; • strobilurines such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methyl-benzyloxy- imino)-ethyl]-benzyl)-carbamate, methyl (2-chloro-5-[1 -(6-methyl-pyridin-2- ylmethoxyimino)-ethyl]-benzyl)-carbamate and methyl 2-ortho-[(2,5-dimethyl- phenyl-oxymethylen)phenyl]-3-methoxy-acrylate;

• cinnamic acid amides and analogous such as dimethomorph, flumetover and flumorph.

25. The formulation according to claim 22 or 23, wherein the formulation comprises at least one insecticidal active ingredient, selected from the group fipronil, imidacloprid, acetamipird, nitenpyram, carbofuran, carbosulfan, benfuracarb, thiacloprid, clothianidin, MTI 446 and CGA 293343.

26. The formulation according to any one of claims 22 to 25, wherein the formulation comprises a mammal/bird repellent.

27. The formulation according to claim 22, wherein the seed treatment auxiliary agent is a seed coating auxiliary agent, a solid matrix material, a penetration enhancer, a colorant, an antifreeze, or a gelling agent.

28. The formulation according to claim 27, wherein the seed coating auxiliary agent is a binder.

29. A seed treated with the method according to any one of claims 1 to 21 or with the formulation according to any one of claims 22 to 28.

30. A seed comprising an arylanilide of the formula I according to any one of claims 1 to 7, and optionally at least one fungicidal active ingredient, selected from the group • azoles such as bromoconazole, cyproconazole, difenoconazole, epoxyconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol and triticonazole; • acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace and oxadixyl;

• amine derivates such as guazatine;

• anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil;

• dicarboximides such as iprodione, procymidon and vinclozolin;

• dithiocarbamates such as mancozeb, metiram and thiram; • heterocyclic compounds such as benomyl, boscalide, carbendazim, carboxin, oxycarboxin, fuberidazole, picobenzamide, penthiopyrad, proquinazid, thiabendazol and thiophanate-methyl;

• phenylpyrroles such as fenpiclonil and fludioxonil;

• other fungicides, for example benthiavalicarb, cyflufenamide, fosetyl, fosetyl- aluminium, phosphoric acid and its salts, iprovalicarb, metrafenone and 5- chloro-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidine;

• strobilurines such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methyl- benzyloxyimino)-ethyl]-benzyl)-carbamate, methyl (2-chloro-5-[1 -(6-methyl- pyridin-2-ylmethoxyimino)-ethyl]-benzyl)-carbamate and 2-ortho-[(2,5- dimethylphenyl-oxymethylen)phenyl]-3-methoxy-acrylate;

• cinnamic acid amides and analogous such as dimethomorph, flumetover and flumorph,

• and/or at least one insecticidal active ingredient, selected from the group fipronil, imidacloprid, acetamipird, nitenpyram, carbofuran, carbosulfan, benfuracarb, thiacloprid, clothianidin, MTI 446 and CGA 293343.

31. A seed according to claim 29 or 30, wherein the seed has a coating, the coating comprising an arylanilide of the formula I according to any one of claims 1 to 7, and optionally at least one fungicidal active ingredient, selected from the group

• Azoles such as bromoconazole, cyproconazole, difenoconazole, epoxyconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazol, tetraconazole, triadimefon, triadimenol and triticonazole;

• acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace and oxadixyl;

• amine derivatives such as guazatine; • anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil;

• dicarboximides such as iprodione, procymidon and vinclozolin;

• dithiocarbamates such as mancozeb, metiram and thiram;

• heterocyclic compounds such as benomyl, boscalide, carbendazim, carboxin, oxycarboxin, fuberidazol, picobenzamide, penthiopyrad, proquinazid, thiabendazole and thiophanate-methyl;

• phenylpyrroles such as fenpiclonil and fludioxonil;

• strobilurines such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methyl-benzyloxy- imino)-ethyl]-benzyl)-carbamate, methyl (2-chloro-5-[1 -(6-methyl-pyridin-2- ylmethoxyimino)-ethyl]-benzyl)-carbamate and methyl 2-ortho-[(2,5- dimethylphenyl-oxymethylen)phenyl]-3-methoxy-acrylate;

• cinnamic acid amides and analogous compounds, such as dimethomorph, flumetover and flumorph,

32. The use of an arylanilide of the formula I according to any one of claims 1 to 7, optionally together with at least one fungicidal active ingredient, selected from the group

• azoles such as bromoconazole, cyproconazole, difenoconazole, epoxyconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol and triticonazole;

• acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace and oxadixyl;

• amine derivatives such as guazatine;

• anilinopyrimidines such as pyrimethanil, mepanipyrim and cyprodinil;

• dicarboximides such as iprodione, procymidon and vinclozolin; • dithiocarbamates such as mancozeb, metiram and thiram;

• heterocyclic compounds such as benomyl, boscalide, carbendazim, carboxin, oxycarboxin, fuberidazole, picobenzamide, penthiopyrad, proquinazid, thiabendazol and thiophanate-methyl;

• phenylpyrroles such as fenpiclonil and fludioxonil; • other fundicides, for example benthiavalicarb, cyflufenamide, fosetyl, fosetyl- aluminium, phosphoric acid and its salts, iprovalicarb, metrafenone and 5- chloro-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidin;

• strobilurines such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methyl-benzyloxy- imino)-ethyl]-benzyl)-carbamate, methyl (2-chloro-5-[1 -(6-methyl-pyridin-2- ylmethoxyimino)-ethyl]-benzyl)-carbarnate and methyl 2-ortho-[(2,5-dimethyl- phenyl-oxymethylen)phenyl]-3-methoxy-acrylate; • cinnamic acid amides and analogous compounds, such as dimethomorph, flumetover and flumorph, and/or at least one insecticidal active ingredient, selected from the group fipronil, imidacloprid, acetamipird, nitenpyram, carbofuran, carbosulfan, benfuracarb, thiacloprid, clothianidin, MTI 446 and CGA 293343, for seed treatment.