N-substituted phenethylcarboxamides as fungicides

The present invention relates to the use of N-substituted phenethylcarboxamides for the control of phytopathogenic microorganisms in agriculture, wherein a compound of formula (I) is applied to the phytopathogenic microorganisms, their habitat, the plant, the seed thereof, plant parts, plant propagation material or the soil on which the plants are grown or intended to be grown in an effective amount.

The present invention further relates to compositions containing such compounds and methods for the control of phytopathogenic microorganisms on plants, the habitat of such microorganims, the plant, the seed thereof, plant parts, plant propagation material or the soil on which the plants are grown or intended to be grown.

Phytopathogenic microorganisms cause a substantial loss in agricultural production including food and industrial crops and are control with compounds having fungicidal activity. To be useful in agriculture these compounds should have a high activity against phytopathogenic microorganisms, a broad spectrum activity against different species of phytopathogenic microorganisms and should be able to be applied in an environmentally safe way.

In WO 201 1/147690 Al certain fungicidal pyrazole carboxamide derivatives are generically embraced in a broad disclosure of numerous compounds of the following formula:

wherein n can be 0 and R can represent hydrogen, Ci-C i-alkyl or Ci-C i-haloalkyl. However, this document only discloses compounds displaying pyrazole-4-carboxamides.

In WO 2010/063700 A2 certain fungicidal pyrazole carboxamide derivatives are generically embraced in a broad disclosure of numerous compounds of the following formula:

wherein X can represent a direct bond, an oxygen atom or a sulfur atom and wherein n can be 0, R can represent hydrogen, Ci-C i-alkyl or Ci-C i-haloalkyl and R ⁷ can represent hydrogen, halogen, C1 -C4- alkyl, C2-C6-alkenyl, C3-C6-alkynyl. However, this document only discloses pyrazole-4-carboxamides with a fungicidal activity.

Therefore there is a need to provide further compounds suitable to control phytopathogenic microorganisms in agriculture with a high activity.

The object of the invention, and further objects which are not stated explicitly but can be discerned or derived from the connections discussed herein, are achieved by the use of a compound of formula (I),

(I) or an N-oxide, or an optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture, wherein n represents 0, 1 , 2, 3, 4 or 5;

X independently from each other X represents halogen, nitro, cyano, isonitrile, hydroxy, amino, sulfanyl, pentafluoro^ ⁶ -sulfanyl, formyl, formyloxy, formylamino, (hydroxyimino)-Ci-C8-alkyl, (Ci-Cs- alkoxyimino)-Ci-C8-alkyl, (C ₂ -C8-alkenyloxyimino)-Ci-C8-alkyl, (C3-C8-alkynyloxyimino)-Ci-C8-alkyl, (benzyloxyimino)-Ci-C8-alkyl, carboxy, carbamoyl, thiocarbamoyl, N-hydroxycarbamoyl, carbamate, Ci-C8-alkyl, Ci-Cs-halogenoalkyl having 1 to 9 halogen atoms, C ₂ -C8-alkenyl, C ₂ -C8-halogenoalkenyl - - having 1 to 9 halogen atoms, C ₂ -C8-alkynyl, C ₂ -C8-halogenoalkynyl having 1 to 9 halogen atoms, Ci-Cs- alkoxy, Ci-Cs-halogenoalkoxy having 1 to 9 halogen atoms, Ci-Cs-alkylsulfanyl, Ci-Cs- halogenoalkylsulfanyl having 1 to 9 halogen atoms, Ci-Cs-alkylsulfinyl, Ci-Cs-halogenoalkylsulfinyl having 1 to 9 halogen atoms, Ci-Cs-alkylsulfonyl, Ci-Cs-halogenoalkylsulfonyl having 1 to 9 halogen atoms, Ci-C8-alkylamino, di-(Ci-C8-alkyl)-amino, C2-C8-alkenyloxy, C2-C8-halogenoalkenyloxy having 1 to 9 halogen atoms, C3-C8-alkynyloxy, C3-C8-halogenoalkynyloxy having 1 to 9 halogen atoms, C3-C7- cycloalkyl, C3-C7-halogenocycloalkyl having 1 to 9 halogen atoms, C3-C7-cycloalkoxy, C4-C7- cycloalkenyl, C4-C7-halogenocycloalkenyl having 1 to 9 halogen atoms, (C3-C7-cycloalkyl)-Ci-C8-alkyl, (C3-C ₇ -cycloalkyl)-C ₂ -C8-alkenyl, (C3-C ₇ -cycloalkyl)-C ₂ -C8-alkynyl, tri-(Ci-C ₈ -alkyl)-silyl, tri-(Ci-C ₈ - alkyl)-silyl-Ci-C8-alkyl, Ci-Cs-alkylcarbonyl, Ci-Cs-halogenoalkylcarbonyl having 1 to 9 halogen atoms, Ci-C8-alkylcarbonyloxy, Ci-Cs-halogenoalkylcarbonyloxy having 1 to 9 halogen atoms, Ci-Cs- alkylcarbonylamino, Ci-Cs-halogenoalkylcarbonylamino having 1 to 9 halogen atoms, Ci-Cs- alkoxycarbonyl, Ci-Cs-halogenoalkoxycarbonyl having 1 to 9 halogen atoms, Ci-Cs- alkyloxycarbonyloxy, Ci-Cs-halogenoalkoxycarbonyloxy having 1 to 9 halogen atoms, Ci-Cs- alkylcarbamoyl, di-Ci-Cs-alkylcarbamoyl, Ci-Cs-alkylaminocarbonyloxy, di-Ci-Cs- alkylaminocarbonyloxy, N-(Ci-C8-alkyl)-hydroxycarbamoyl, Ci-Cs-alkoxycarbamoyl, N-(Ci-Cs-alkyl)- Ci-C8-alkoxycarbamoyl, aryloxy optionally substituted by 1 to 6 groups Q which can be the same or different, arylsulfanyl optionally substituted by 1 to 6 groups Q which can be the same or different, arylamino optionally substituted by 1 to 6 groups Q which can be the same or different, aryl-Ci-Cs- alkyloxy optionally substituted by 1 to 6 groups Q which can be the same or different, aryl-Ci-Cs- alkylsulfanyl optionally substituted by 1 to 6 groups Q which can be the same or different, aryl-Ci-Cs- alkylamino optionally substituted by 1 to 6 groups Q which can be the same or different, pyridinyl which can be substituted by 1 to 4 groups Q, pyridinyloxy which is optionally substituted by 1 to 4 groups Q, or two substituents X together with the carbon atoms to which they are attached form a 5- or 6-membered, saturated carbocycle or saturated heterocycle, which is optionally substituted by 1 to 4 groups Q which can be the same or different;

Z ¹ and Z ² independently represent hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl having 1 to 5 halogen atoms, Ci-Cs-alkoxy, Ci-Cs-alkylsulfanyl, or Ci-Cs-alkoxycarbonyl;

Z ³ and Z ⁴ independently represent hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl having 1 to 5 halogen atoms, Ci-Cs-alkoxy, Ci-Cs-alkylsulfanyl, or Ci-Cs-alkoxycarbonyl, or

Z ³ and Z ⁴ form together with the carbon atom to which they are attached a 3- to 6-membered, saturated carbocycle or saturated heterocycle, which is optionally substituted by 1 to 6 groups Q which can be the same or different; Z ^a represents hydrogen, Ci-Cg-alkyl, C3-Cg-alkenyl, C3-Cg-alkynyl, Ci-Cg-halogenoalkyl comprising 1 to 9 halogen atoms, C3-C7-cycloalkyl or C3-C7-cycloalkyl substituted by 1 to 10 substituents that can be the same or different, selected from the list consisting of halogen, cyano, Ci-Cg- alkyl, Ci-Cg-halogenoalkyl comprising 1 to 9 halogen atoms;

Q represents halogen, cyano, nitro, Ci-Cg-alkyl, Ci-Cg-halogenoalkyl having 1 to 9 halogen atoms, Ci- C8-alkoxy, Ci-Cg-halogenoalkoxy having 1 to 9 halogen atoms, Ci-Cg-alkylsulfanyl, Ci-Cg- halogenoalkylsulfanyl having 1 to 9 halogen atoms, tri-(Ci-C8-alkyl)-silyl, tri-(Ci-Cg-alkyl)-silyl-Ci-Cg- alkyl, Ci-Cg-alkoxyimino-Ci-Cg-alkyl, (benzyloxyimino)-Ci-Cg-alkyl;

A represents phenyl of formula A ¹

(A ¹ ) wherein

* indicates the bond which connects A ¹ to the C=0 moiety of the compounds of formula (I),

Y ¹ represents halogen, nitro, SH, SF ₅ , CHO, OCHO, NHCHO, cyano, Ci-Cg-alkyl, Ci-Cg-halogenoalkyl having 1 to 5 halogen atoms, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl, C3-C6-cycloalkyl, C3-C6-halogenocycloalkyl having 1 to 9 halogen atoms, Ci-Cg-alkylsulfanyl, -Ci-Cg-halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-Cg-alkoxy, Ci-Cg-halogenoalkoxy having 1 to 5 halogen atoms, Ci-Cg-alkoxy-Ci-Cg-alkyl, C2- Cg-alkenyloxy-Ci-Cg-alkyl, C3-Cg-alkynyloxy-Ci-Cg-alkyl, C ₂ -Cg-alkenyloxy, C3-Cg-alkynyloxy, Ci-Cg- alkoxycarbonyl, Ci-Cg-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, Ci-Cg-alkylcarbonyloxy, Ci-Cg-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, Ci-Cg-alkylsulfinyl, Ci-Cg- halogenoalkylsulfinyl having 1 to 5 halogen atoms, Ci-Cg-alkylsulfonyl, Ci-Cg-halogenoalkylsulfonyl having 1 to 5 halogen atoms, Ci-Cg-alkylsulfonamide, tri-(Ci-Cg)-alkylsilyl, aryl and aryloxy;

Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ; or

A represents a heterocycle of formula (A )

(A ² ) wherein

R ¹ to R ³ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ³ )

(A ³ ) wherein

R ⁴ to R ⁶ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁴ )

(A ⁴ ) wherein

R ⁷ represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, and - -

R ⁸ represents hydrogen or Ci-Cs-alkyl; or

A represents a heterocycle of formula (A ⁵ )

(A ⁵ ) wherein

R ⁹ to R ¹¹ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, amino, Ci-Cs-alkoxy, Ci-Cs-alkylsulfanyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms or C1-C5- halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁶ )

(A ⁶ ) wherein

R and R independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, amino, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, and

R ¹⁴ represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, amino, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁷ )

wherein represents hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and

R and R independently from each other represent hydrogen, halogen, Ci-Cs-alkoxycarbonyl, C1-C5- alkyl, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and

R ¹⁷ represents hydrogen or Ci-Cs-alkyl; or

A represents a heterocycle of formula (A ⁸ )

(A ⁸ ) wherein

R represents hydrogen or substituted or unsubstitued Ci-Cs-alkyl, and

R to R independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C1-C5 halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁸ )

(A ⁸ ) wherein represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and R ²⁴ represents hydrogen or Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or A represents a heterocycle of formula (A ¹⁰ )

(A ¹⁰ ) wherein

R ²⁵ represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and

R ²⁶ represents hydrogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or A represents a heterocycle of formula (A ¹¹ )

(A ¹¹ ) wherein

R ²⁷ represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and

R ²⁸ represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-Cs-alkylamino or di-(Ci-Cs- alkyl)-amino; or

A represents a heterocycle of formula (A ¹² ) - -

wherein

R represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and

R ³⁰ represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-Cs-alkylamino or di-(Ci-Cs- alkyl)-amino; or

A represents a heterocycle of formula (A ¹³ )

(A ¹³ ) wherein

R ³¹ represents hydrogen or Ci-Cs-alkyl, and

R ³² represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and

R ³³ represents hydrogen, halogen, nitro, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ¹⁴ )

- -

(A ¹⁴ ) wherein

R ³⁷ and R ³⁸ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, C1-C5 halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy or a Ci-Cs-alkylsulfanyl, and R ³⁹ represents hydrogen or Ci-Cs-alkyl; or

A represents a heterocycle of formula (A ¹⁵ )

(A ¹⁵ ) wherein R and R independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C1-C5- halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A )

(A ¹⁶ ) wherein

R ⁴² and R ⁴³ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, C1-C5 halogenoalkyl comprising 1 to 9 halogen atoms or amino; or

A represents a heterocycle of formula (A ¹⁷ )

- -

(A ¹⁷ ) wherein

R ⁴⁴ and R ⁴⁵ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C1-C5 halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ¹⁸ )

(A ¹⁸ ) wherein

R ⁴⁷ represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and

R represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-Cs-alkylsulfanyl; or

A represents a heterocycle of formula (A ¹⁹ )

(A ¹⁹ ) wherein

R ⁴⁹ and R ⁴⁸ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci- C5-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ²⁰ )

- -

(A ²⁰ ) wherein

R ⁵⁰ and R ⁵¹ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci- C5-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms: or

A represents a heterocycle of formula (A ²¹ )

(A ²¹ ) wherein

R ⁵² represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ²² )

(A ²² ) wherein

R ⁵³ represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ²³ )

(A ²³ ) wherein

R ⁵⁴ and R ⁵⁶ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C halogenoalkyl comprising 1 to 9 halogen atoms, and

R ⁵⁵ represents hydrogen or Ci-Cs-alkyl; or

- -

A represents a heterocycle of formula (A )

(A ²⁴ ) wherein

R ⁵⁷ and R ⁵⁹ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C halogenoalkyl comprising 1 to 9 halogen atoms, and

R ⁵⁸ represents hydrogen or Ci-Cs-alkyl; or

A represents a heterocycle of formula (A ²⁵ )

*

(A ²⁵ ) wherein

R ⁶⁰ and R ⁶¹ independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C halogenoalkyl comprising 1 to 9 halogen atoms, and

R ⁶² represents a hydrogen atom or Ci-Cs-alkyl; or

A represents a heterocycle of formula (A ²⁶ )

(A ²⁶ ) - 5- wherein

R represents hydrogen, halogen, Ci-Cs-alkyl, cyano, Ci-Cs-alkoxy, Ci-Cs-alkylsulfanyl, C1-C5- halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-Cs-alkylamino or di(Ci-C5-alkyl)amino, and

R ⁶⁴ represents hydrogen or Ci-Cs-alkyl, and

R ⁶⁵ represents hydrogen, halogen, Ci-Cs-alkyl, C3-Cs-cycloalkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy, C3-Cs-alkynyloxy or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ²⁷ )

in which

R ⁶⁶ represents hydrogen, halogen, hydroxy, cyano, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms, Ci-C i-alkoxy, Ci-C i-alkylsulfanyl, Ci-C i-halogenoalkylsulfanyl having 1 to 5 halogen atoms and Ci-C i-halogenoalkoxy having 1 to 5 halogen atoms, and

R ⁶⁷ , R ⁶⁸ and R ⁶⁹ independently from each other represent hydrogen, halogen, cyano, Ci-C i-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, SCi-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl; or

A represents a heterocycle of formula (A ²⁸ )

in which

R ⁷⁰ represents hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-Cs-alkylsulfanyl, C2-C5-alkenylsulfanyl, C1-C4- - - halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C i-halogenoalkoxy having 1 to 5 halogen atoms and

R ⁷¹ , R ⁷² and R ⁷³ independently from each other represent hydrogen, halogen, cyano, Ci-C i-alkyl, C ₁ -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl; or

A represents a heterocycle of formula (A )

in which

R , R , R and R independently from each other represent hydrogen, halogen, hydroxy, cyano, Ci- C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl; or

A represents a heterocycle of formula (A ³⁰ )

in which

X ¹ represents -S-, -SO-, -SO2- and -CH ₂ -, and

R represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, and

R and R independently from each other represent hydrogen and Ci-C4-alkyl; or

A represents a heterocycle of formula (A ³¹ )

- 7- in which

R ⁸¹ represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms; A represents a heterocycle of formula (A ³² )

in which

R represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms; or

A represents a heterocycle of formula (A )

in which

R represents hydrogen, halogen, Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms;

Wherein the * in formulae A ¹ to A ³³ indicates the bond which connects A ¹ to A ³³ to the C=0 moiety of the compounds of formula (I).

In the above definitions, unless stated otherwise, carboxy means -C(=0)OH,

carbonyl means -C(=0)-,

carbamoyl means -C(=0)NH2, alkylcarbamoyl means -C(=0)NHalkyl dialkylcarbamoyl means -C(=0)N(alkyl)2

N-hydroxycarbamoyl means -C(=0)NHOH,

SO represents a sulfoxyde group,

SO2 represents a sulfone group, an alkyl group, an alkenyl group and an alkynyl group as well as moieties containing these terms, can be - - linear or branched.

The term "aryl", also in terms like arylalkyl, arylalkenyl, arylalkynyl, aryloxy means phenyl or naphthyl, wherein phenyl is optionally substituted by 1 to 5 groups Q, and naphtyl is optionally substituted by 1 to 6 groups Q.

The term "heterocyclyl" means a saturated, partially saturated or unsaturated 4-, 5-, 6-, 7-, 8-, 9-, or 10- membered ring comprising 1 to 4 heteroatoms selected from the list consisting of oxygen (O), nitrogen (N), and sulfur (S).

Heteroatom means an atom selected from the group consisting of O, N, and S.

Unless indicated otherwise, if more than one halogen atom is present in a halogenated radical, like e.g. halogenoalkyl, halogenoalkoxy, those halogen atoms can be the same or different.

In the definitions of the symbols given in the above formulae, collective terms were used which are generally representative of the following substituents:

The definition Ci-Cs-alkyl comprises the largest range defined here for an alkyl radical. Specifically, this definition comprises the meanings methyl, ethyl, n , isopropyl, n , iso , sec , tert-butyl, and also in each case all isomeric pentyls, hexyls, heptyls and octyls, such as methyl, ethyl, propyl, 1 -me-thylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3- methylbutyl, 1 ,2-dimethylpropyl, 1 , 1 -dimethylpropyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1 , 1 -di-me-thylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1 , 1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethylbutyl, 2-ethylbutyl, l-ethyl-3-methylpropyl, n-heptyl, 1 -methylhexyl, 1- ethylpentyl, 2-ethylpentyl, 1 -propylbutyl, octyl, 1 -me-thylheptyl, 2-methylheptyl, 1-ethylhexyl, 2- ethylhexyl, 1 -propylpentyl and 2-propylpentyl, in particular propyl, 1 -methylethyl, butyl, 1- me-'thyl-'bu-tyl, 2-methylbutyl, 3 -methylbutyl, 1,1-dimethylethyl, 1 ,2-dimethylbutyl, 1,3- dimethylbutyl, pentyl, 1 -methyHbu-tyl, 1 -ethylpropyl, hexyl, 3-methylpentyl, heptyl, 1 -methylhexyl, 1- ethyl-3 -methylbutyl, 1 -methylheptyl, 1 1,3-dimethyloctyl, 4-methyloctyl, 1,2,2,3- tetramethylbutyl, 1,3,3-trimethylbutyl, 1,2,3-trimethylbutyl, 1,3-dimethylpentyl, 1,3-dimethylhexyl, 5- methyl-3 -hexyl, 2-methyl-4-heptyl and 1 -methyl-2-cyclopropylethyl. A preferred range is Cl-C4-alkyl, such as methyl, ethyl, n , isopropyl, n , iso , sec , tert-butyl. The definition Cl-C3-alkyl comprises methyl, ethyl, n , isopropyl.

The definition halogen comprises fluorine, chlorine, bromine and iodine.

Halogen-substituted alkyl - referred to as Ci-Cs-halogenoalkyl - represents, for example, Ci-Cs-alkyl as defined above substituted by one or more halogen substituents which can be the same or different. - -

Preferably Ci-Cs-haloalkyl represents chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 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, pentafluoroethyl, 1 -fluoro-l -methylethyl, 2-fluoro-l , l -dimethylethyl, 2-chloro-l , l -dimethylethyl, 2-fluoro-l -fluoromethyl- 1 -methylethyl, 2- fluoro-l , l -di(fluoromethyl)-ethyl, 3-chloro-l -methylbutyl, 2-chloro-l -methylbutyl, 1 -chlorobutyl, 3,3- dichloro-l -methylbutyl, 3-chloro-l -methylbutyl, l -methyl-3-trifluoromethylbutyl, 3 -methyl- 1 - trifluoromethylbutyl.

The definition C2-C8-alkenyl comprises the largest range defined here for an alkenyl radical. Specifically, this definition comprises the meanings ethenyl, n , isopropenyl, n , iso , sec , tert-butenyl, and also in each case all isomeric pentenyls, hexenyls, heptenyls, octenyls, 1 -methyl- 1 -propenyl, 1 - ethyl-l -butenyl, 2,4-dimethyl-l -pentenyl, 2,4-dimethyl-2-pentenyl. Halogen-substituted alkenyl - referred to as C2-C8-halogenoalkenyl - represents, for example, C2-C8-alkenyl as defined above substituted by one or more halogen substituents which can be the same or different.

The definition C2-C8-alkynyl comprises the largest range defined here for an alkynyl radical. Specifically, this definition comprises the meanings ethynyl, n , isopropynyl, n , iso , sec , tert-butynyl, and also in each case all isomeric pentynyls, hexynyls, heptynyls, octynyls. Halogen-substituted alkynyl - referred to as C2-C8-halogenoalkynyl - represents, for example, C2-C8-alkynyl as defined above substituted by one or more halogen substituents which can be the same or different.

The definition C3-C7-cycloalkyl comprises monocyclic saturated hydrocarbyl groups having 3 to 7 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.

The definition halogen-substituted cycloalkyl and halocycloalkyl comprises monocyclic saturated hydrocarbyl groups having 3 to 7 carbon ring members, such as 1 -fluoro-cyclopropyl, 1 -chloro- cyclopropyl, 1 -bromo-cyclopropyl, 2,2-dichloro- 1 -methyl-cyclopropyl, 2,2-dibromo-l -methyl- cyclopropyl, 1 -fluoro-cyclobutyl, 1 -chloro-cyclobutyl, 1 -fluoro-cyclopentyl, 1 -chloro-cyclopentyl, 1 - fluoro-cyclohexyl or 1 -chloro-cyclohexyl.

Compounds of the present invention can exist in one or more optical or chiral isomer forms depending on the number of asymmetric centres in the compound. The invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic" denotes a mixture of enantiomers in different proportions) and to the mixtures of all the possible stereoisomers, in all proportions. The diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by the man ordinary skilled in the art.

Compounds of the present invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions. The geometric isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art.

Any of the compounds of formula (I) wherein X represents a hydroxy, a sulfanyl or an amino may be found in its tautomeric form resulting from the shift of the proton of said hydroxy, sulfanyl or amino group. Such tautomeric forms of such compounds are also part of the present invention. More generally speaking, all tautomeric forms of compounds of formula (I) wherein X represents a hydroxy, a sulfanyl group or an amino group, as well as the tautomeric forms of the compounds which can optionally be used as intermediates in the preparation processes and which will be defined in the description of these processes, are also part of the present invention.

Definitions

"Agriculture" shall encompass the production of food and feed crops, forestry, the protection of stored products including food, feed but also other materials of plant origin. Preferably agriculture shall encompass the production of food and feed crops, forestry, the protection of stored products being food, feed, and materials of plant origin.

"Plant product" mean any product derived from a plant.

In the context of the present invention, "control of phytopathogenic microorganisms" means a reduction in infestation by phytopathogenic microorganisms, compared with the untreated plant, the seed of a plant, the plant propagation material or the plant product, measured as efficacy, preferably a reduction by 25-50 %, compared with the untreated plant, the seed of a plant, the plant propagation material or the plant product (100 %), more preferably a reduction by 40-79 %, compared with the the untreated plant, the seed of a plant, the plant propagation material or the plant product (100 %); even more preferably, the infection by phytopathogenic microorganisms is entirely suppressed (by 70-100 %). The control may be curative, i.e. for treatment of the plant, the seed of a plant, the plant propagation material or the plant product or protective, for protection of the untreated plant, the seed of a plant, the plant propagation material or the plant product, which have not yet been infected.

An "effective amount" means an amount of the inventive compound which is sufficient to control the phytopathogenic microorganism in a satisfactory manner or to eradicate the phytopathogenic microorganism completely, and which, at the same time, does not cause any significant symptoms of phytotoxicity. In general, this application rate may vary within a relatively wide range. It depends on several factors, for example on the phytopathogenic microorganism to be controlled, the plant, the climatic conditions and the ingredients of the inventive compositions.

Phytopathogenic microorganisms mean fungi and bacteria capable of infecting a plant, a seed of a plant, a plant propagation material or a plant product. - -

Preferably phytopathogenic microorganism means phytopathogenic fungi.

Fungi means Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti).

Bacteria means species including Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae capable of infecting a plant, a seed of a plant, a plant propagation material or a plant product.

Preferably the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture, wherein A is a group of formula A ¹

(A1) wherein

* indicates the bond which connects A ¹ to the C=0 moiety of the compounds of formula (I),

Y ¹ represents halogen, nitro, SH, SF ₅ , CHO, OCHO, NHCHO, cyano, Ci-C ₄ -alk l, Ci-C ₄ -halogenoalkyl having 1 to 5 halogen atoms, C ₂ -C i-alkenyl, C ₂ -C ₄ -alkynyl, C3-C6-cycloalkyl, C3-C6-halogenocycloalkyl having 1 to 9 halogen atoms, Ci-C i-alkylsulfanyl, -Ci-C i-halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C i-alkoxy, Ci-C i-halogenoalkoxy having 1 to 5 halogen atoms, Ci-C i-alkoxy-Ci-C i-alkyl, C2- C i-alkenyloxy-Ci-C i-alkyl, C3-C4-alkynyloxy-Ci-C4-alkyl, C2-C4-alkenyloxy, C3-C4-alkynyloxy, C1-C4- alkoxycarbonyl, Ci-C ₄ -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, Ci-C ₄ -alkylcarbonyloxy, Ci-C4-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, Ci-C4-alkylsulfinyl, C1-C4- halogenoalkylsulfinyl having 1 to 5 halogen atoms, Ci-C ₄ -alkylsulfonyl, Ci-C ₄ -halogenoalkylsulfonyl having 1 to 5 halogen atoms, Ci-C4-alkylsulfonamide, tri-(Ci-C4)-alkylsilyl, aryl and aryloxy;

Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ; or

A represents a heterocycle of formula (A ² ) - -

(A ² ) wherein

R ¹ to R ³ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-alkoxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ³ )

(A ³ ) wherein

R ⁴ to R ⁶ independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-alkoxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁵ )

(A ⁵ ) wherein

R ⁹ to R ¹¹ independently from each other represent hydrogen, halogen, Ci-C4-alkyl, amino, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or C ₁ -C4- halogenoalkoxy comprising 1 to 9 halogen atoms; or - -

A represents a heterocycle of formula (A ⁶ )

(A ⁶ ) wherein

R ¹² and R ¹³ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-alkoxy, amino, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C i-halogenoalkoxy comprising 1 to 9 halogen atoms, and

R ¹⁴ represents hydrogen, halogen, Ci-C i-alkyl, Ci-C4-alkoxy, amino, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A is a heterocycle of formula (A ²⁷ )

in which

R represents hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-halogenoalkylsulfanyl having 1 to 5 halogen atoms and Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, and

R ⁶⁷ , R ⁶⁸ and R ⁶⁹ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C ₁ -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, SCi-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl; or

A is a heterocycle of formula (A ²⁸ )

- - in which

R represents hydrogen, halogen, hydroxy, cyano, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms, Ci-C i-alkoxy, Ci-C4-alkylsulfanyl, C2-C4-alkenylsulfanyl, C1-C4- halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms and

R ⁷¹ , R ⁷² and R ⁷³ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C ₁ -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl; or

A is a heterocycle of formula (A ³³ )

in which

R represents hydrogen, halogen, Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms; n represents 0, 1, 2, or 3;

X independently from each other X represents halogen, nitro, cyano, isonitrile, hydroxy, amino, sulfanyl, pentafluoro^ ⁶ -sulfanyl, formyl, formyloxy, formylamino, carboxy, carbamoyl, thiocarbamoyl, N-hydroxycarbamoyl, carbamate, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C2-C4- alkenyl, C ₂ -C4-halogenoalkenyl having 1 to 9 halogen atoms, C ₂ -C4-alkynyl, C ₂ -C4-halogenoalkynyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, C1-C4- alkylamino, di-(Ci-C4-alkyl)-amino, C2-C4-alkenyloxy, C2-C4-halogenoalkenyloxy having 1 to 9 halogen atoms, C3-C4-alkynyloxy, C3-C4-halogenoalkynyloxy having 1 to 9 halogen atoms, C3-C7-cycloalkyl, C3- C7-halogenocycloalkyl having 1 to 9 halogen atoms, C3-C7-cycloalkoxy, C4-C7-cycloalkenyl, C4-C7- halogenocycloalkenyl having 1 to 9 halogen atoms, (C3-C7-cycloalkyl)-Ci-C4-alkyl, (C3-C7-cycloalkyl)- C ₂ -C ₄ -alkenyl, (C ₃ -C7-cycloalkyl)-C2-C ₄ -alkynyl, tri-(Ci-C ₄ -alkyl)-silyl, tri-(Ci-C ₄ -alkyl)-silyl-Ci-C ₄ - alkyl, Ci-C4-alkylcarbonyl, Ci-C4-halogenoalkylcarbonyl having 1 to 9 halogen atoms, C ₁ -C4- alkylcarbonyloxy, Ci-C4-halogenoalkylcarbonyloxy having 1 to 9 halogen atoms, C1-C4- alkylcarbonylamino, Ci-C4-halogenoalkylcarbonylamino having 1 to 9 halogen atoms, C1-C4- alkoxycarbonyl, Ci-C4-halogenoalkoxycarbonyl having 1 to 9 halogen atoms, C ₁ -C4- alkyloxycarbonyloxy, Ci-C4-halogenoalkoxycarbonyloxy having 1 to 9 halogen atoms, C1-C4- alkylcarbamoyl, di-Ci-C4-alkylcarbamoyl, Ci-C4-alkylaminocarbonyloxy; - 5-

Z ¹ and Z ² independently represent hydrogen, halogen, cyano, Ci-C i-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, or Ci-C4-alkoxycarbonyl;

Z ³ and Z ⁴ independently represent hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, or Ci-C4-alkoxycarbonyl, or

Z ³ and Z ⁴ form together with the carbon atom to which they are attached a C ₂ -C4-cycloalkyl, which is optionally substituted by 1 to 6 groups Q which can be the same or different;

Z ^a represents hydrogen, Ci-C4-alkyl, C3-C4-alkenyl, C3-C4-alkynyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, C3-C7-cycloalkyl or C3-C7-cycloalkyl substituted by 1 to 10 substituents that can be the same or different, selected from the list consisting of halogen, cyano, C1-C4- alkyl, Ci-C4-halogenoalkyl comprising 1 to 5 halogen atoms;

Q represents halogen, cyano, nitro, Ci- C4-alkyl, Ci- C4-halogenoalkyl having 1 to 5 halogen atoms, Ci- C4-alkoxy, Ci- C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci- C4-alkylsulfanyl, C1-C4- halogenoalkylsulfanyl having 1 to 9 halogen atoms, tri-(Ci-C4-alkyl)-silyl, tri-(Ci-C4-alkyl)-silyl-Ci-C4- alkyl, Ci-C4-alkoxyimino-Ci-C4-alkyl, (benzyloxyimino)-Ci-C4-alkyl.

More preferably the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture, wherein A is a group of formula A ¹

(A ¹ ) wherein

* indicates the bond which connects A ¹ to the C=0 moiety of the compounds of formula (I),

Y ¹ represents halogen, nitro, SH, SF ₅ , CHO, OCHO, NHCHO, cyano, Ci-C ₄ -alkyl, Ci-C ₄ -halogenoalkyl having 1 to 5 halogen atoms, C ₂ -C ₄ -alkenyl, C3-C6-cycloalkyl, C3-C6-halogenocycloalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, Ci-C4-alkoxy-Ci-C4- alkyl, Ci-C i-alkoxycarbonyl, Ci-C4-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C4- alkylcarbonyloxy, Ci-C4-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms;

Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ; or

A represents a heterocycle of formula (A ² )

(A ² ) wherein

R ¹ to R ³ independently from each other represent hydrogen, halogen, C i-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-alkoxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ³ )

(A ³ ) wherein

R ⁴ to R ⁶ independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-alkoxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁵ )

(A ⁵ ) - 7- wherein

R ⁹ to R ¹¹ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, amino, Ci-C i-alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or C ₁ -C4- halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁶ )

(A ⁶ ) wherein

R ¹² and R ¹³ independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, amino, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, and

R ¹⁴ represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, amino, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A is a heterocycle of formula (A ²⁷ )

in which

R ⁶⁶ represents hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, and Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, and

R ⁶⁷ , R ⁶⁸ and R ⁶⁹ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C ₁ -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or

A is a heterocycle of formula (A ) - -

in which

R represents hydrogen, halogen, hydroxy, cyano, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms, Ci-C i-alkoxy, Ci-C i-halogenoalkoxy having 1 to 5 halogen atoms and

R ⁷¹ , R ⁷² and R ⁷³ independently from each other represent hydrogen, halogen, cyano, Ci-C i-alkyl, C ₁ -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or

A is a heterocycle of formula (A )

in which

R represents hydrogen, halogen, Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms; n represents 0, 1, 2, or 3;

X independently from each other X represents halogen, nitro, cyano, isonitrile, hydroxy, amino, carboxy, carbamoyl, thiocarbamoyl, N-hydroxycarbamoyl, carbamate, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C2-C4-alkenyl, C2-C4-halogenoalkenyl having 1 to 9 halogen atoms, C1-C4- alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkylamino, di-(Ci-C4-alkyl)-amino, C3-C7-cycloalkyl, C3-C7-halogenocycloalkyl having 1 to 9 halogen atoms, C3-C7-cycloalkoxy, (C3-C7- cycloalkyl)-Ci-C ₄ -alkyl, tri-(Ci-C ₄ -alkyl)-silyl, tri-(Ci-C ₄ -alkyl)-silyl-Ci-C ₄ -alkyl, Ci-C ₄ -alkylcarbonyl, Ci-C4-halogenoalkylcarbonyl having 1 to 9 halogen atoms, Ci-C4-alkylcarbonyloxy, C1-C4- halogenoalkylcarbonyloxy having 1 to 9 halogen atoms, Ci-C4-alkoxycarbonyl, C1-C4- halogenoalkoxycarbonyl having 1 to 9 halogen atoms, Ci-C4-alkyloxycarbonyloxy, C1-C4- halogenoalkoxycarbonyloxy having 1 to 9 halogen atoms;

Z ¹ and Z ² independently represent hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy; Z ³ and Z ⁴ independently represent hydrogen, halogen, cyano, Ci-C i-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy; or

Z ³ and Z ⁴ form together with the carbon atom to which they are attached a C3-cycloalkyl, which is optionally substituted by 1 to 2 groups Q which can be the same or different;

Z ^a represents hydrogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, C3-C7- cycloalkyl or C3-C7-cycloalkyl substituted by 1 to 10 substituents that can be the same or different, selected from the list consisting of halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 5 halogen atoms.

Even more preferably the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture, wherein A is a group of formula A ¹

(A ¹ ) wherein

* indicates the bond which connects A ¹ to the C=0 moiety of the compounds of formula (I),

Y ¹ represents halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, C3-C6- cycloalkyl, C3-C6-halogenocycloalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms;

Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ; or

A represents a heterocycle of formula (A )

- -

(A ² ) wherein

R ¹ to R ³ independently from each other represent hydrogen, halogen, Ci-C i-alkyl or C ₁ -C4- halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ³ )

(A ³ ) wherein

R ⁴ to R ⁶ independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁵ )

(A ⁵ ) wherein

R ⁹ to R ¹¹ independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁶ )

(A ⁶ ) - - wherein

R and R independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-alkoxy, Ci- C4-halogenoalkyl comprising 1 to 9 halogen atoms, and

R ¹⁴ represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxyor Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or

A is a heterocycle of formula (A ²⁷ )

in which

R ⁶⁶ represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, and Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, and

R ⁶⁷ , R ⁶⁸ and R ⁶⁹ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C ₁ -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or

A is a heterocycle of formula (A )

in which

R ⁷⁰ represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms and

R ⁷¹ , R ⁷² and R ⁷³ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C ₁ -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or

A is a heterocycle of formula (A ) - -

in which

R represents hydrogen, halogen, Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms; n represents 0, 1, 2, or 3;

X independently from each other X represents halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, C1-C4- alkylamino, di-(Ci-C4-alkyl)-amino, C3-C7-cycloalkyl, C3-C7-halogenocycloalkyl having 1 to 9 halogen atoms;

Z ¹ and Z ² independently represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy;

Z ³ and Z ⁴ independently represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy; or

Z ³ and Z ⁴ form together with the carbon atom to which they are attached a C3-cycloalkyl;

Z ^a represents hydrogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms.

Most preferably the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture, wherein A is a group of formula A ¹

(A ¹ ) wherein indicates the bond which connects A ¹ to the C=0 moiety of the compounds of formula (I), Y ¹ represents halogen, Ci-C ₂ -halogenoalkyl having 1 to 5 halogen atoms; Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ; or A represents a heterocycle of formula (A ² )

(A ² ) wherein

R ¹ to R ³ independently from each other represent hydrogen, halogen, Ci-C ₂ -alkyl or C ₁ -C ₂ - halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ³ )

wherein

R ⁴ to R ⁶ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁵ )

(A ⁵ ) wherein R ⁹ to R ¹¹ independently from each other represent hydrogen, halogen, Ci-C2-alkyl or Ci halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁶ )

(A ⁶ ) wherein

R ¹² and R ¹³ independently from each other represent hydrogen, halogen, Ci-C2-alkyl or C1-C2- halogenoalkyl comprising 1 to 9 halogen atoms, and

R ¹⁴ represents hydrogen, halogen, Ci-C2-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or

A is a heterocycle of formula (A ²⁷ )

in which

R ⁶⁶ represents hydrogen, halogen, Ci-C2-alkyl or Ci-C2-halogenoalkyl having 1 to 5 halogen atoms, and

R ⁶⁷ , R ⁶⁸ and R ⁶⁹ independently from each other represent hydrogen, halogen, Ci-C2-alkyl or C1-C2- halogenoalkyl having 1 to 5 halogen atoms; or

A is a heterocycle of formula (A ²⁸ )

- 5- in which

R ⁷⁰ represents hydrogen, halogen, Ci-C ₂ -alkyl or Ci-C ₂ -halogenoalkyl having 1 to 5 halogen atoms and

R ⁷¹ , R ⁷² and R ⁷³ independently from each other hydrogen, halogen, Ci-C ₂ -alkyl or Ci-C ₂ -halogenoalkyl having 1 to 5 halogen atoms; or

A is a heterocycle of formula (A ³³ )

in which

R ⁸³ represents hydrogen, halogen, Ci-C ₂ -alkyl or Ci-C ₂ -halogenoalkyl having 1 to 5 halogen atoms; n represents 0, 1 , 2, or 3;

X independently from each other X represents halogen, Ci-C ₂ -alkyl, Ci-C ₂ -halogenoalkyl having

1 to 5 halogen atoms, Ci-C ₂ -alkoxy, Ci-C ₂ -halogenoalkoxy having 1 to 9 halogen atoms; Z ¹ and Z ² independently represent hydrogen or halogen;

Z ³ and Z ⁴ independently represent hydrogen, halogen, Ci-C ₂ -alkyl, Ci-C ₂ -halogenoalkyl having 1 to 5 halogen atoms, Ci-C2-alkoxy;

Z ^■1 a represents hydrogen, Ci-C ₂ -alkyl, Ci-C ₂ -halogenoalkyl comprising 1 to 9 halogen atoms.

- -

Most particularly preferably the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture, wherein A is a group of formula A ¹

(A ¹ ) wherein

* indicates the bond which connects A ¹ to the C=0 moiety of the compounds of formula (I),

Y ¹ represents halogen, trifluoromethyl, difluoromethyl, fluoromethyl;

Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ; or

A represents a heterocycle of formula (A ² )

(A ² ) wherein

R to R independently from each other represent hydrogen, halogen; or

A represents a heterocycle of formula (A )

(A ³ ) wherein

R ⁴ to R ⁶ independently from each other represent hydrogen, halogen; or A represents a heterocycle of formula (A ⁵ )

(A ⁵ ) wherein

R ⁹ to R ¹¹ independently from each other represent hydrogen, halogen; or A represents a heterocycle of formula (A ⁶ )

(A ⁶ ) wherein

R ¹² and R ¹³ independently from each other represent hydrogen, halogen, and

R ¹⁴ represents hydrogen, halogen, Ci-C ₂ -alkyl or Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms; or

A is a heterocycle of formula (A ²⁷ )

in which

R ⁶⁶ represents hydrogen, halogen, trifluoromethyl, difluoromethyl, fluoromethyl, and - -

R , R and R independently from each other represent hydrogen, halogen, trifluoromethyl, difluoromethyl, fluoromethyl; or

A is a heterocycle of formula (A )

in which

R represents hydrogen, halogen, trifluoromethyl, difluoromethyl, fluoromethyl and

R ⁷¹ , R ⁷² and R ⁷³ independently from each other hydrogen, halogen, trifluoromethyl, difluoromethyl, fluoromethyl; or

A is a heterocycle of formula (A )

in which

R represents hydrogen, trifluoromethyl, difluoromethyl, fluoromethyl; n represents 0, 1 , 2, or 3;

X independently from each other X represents halogen, Ci-C ₂ -alkyl, trifluoromethyl, difluoromethyl, fluoromethyl, Ci-C ₂ -alkoxy;

Z ¹ and Z ² independently represent hydrogen or halogen;

Z and Z independently represent hydrogen, Ci-C ₂ -alkyl, trifluoromethyl, difluoromethyl, fluoromethyl; represents hydrogen, Ci-C ₂ -alkyl.

In one embodiment the compound of formula (I) as defined above is a compound, wherein A is a group of formula A ¹ - -

(Α ¹ ) wherein

* indicates the bond which connects A ¹ to the C=0 moiety of the compounds of formula (I),

Y ¹ represents halogen, Ci-C ₂ -halogenoalkyl having 1 to 5 halogen atoms;

Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ; n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound, wherein A is a roup of formula A ¹

(A ¹ )

wherein

* indicates the bond which connects A ¹ to the C=0 moiety of the compounds of formula (I),

Y ¹ represents halogen, Ci-C ₂ -halogenoalkyl having 1 to 5 halogen atoms;

Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the more preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound, wherein A is a group of formula A ¹ - -

(Α ¹ )

wherein

* indicates the bond which connects A ¹ to the C=0 moiety of the compounds of formula (I),

Y ¹ represents halogen, Ci-C2-halogenoalkyl having 1 to 5 halogen atoms;

Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the even more preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

wherein A represents a heterocycle of formula A ² )

(A ² )

wherein

R ¹ to R ³ independently from each other represent hydrogen, halogen, Ci-C2-alkyl or C1-C2- halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ³

(A ³ )

wherein

R ⁴ to R ⁶ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound, wherein A represents a heterocycle of formula A ² )

(A ² )

wherein

R ¹ to R ³ independently from each other represent hydrogen, halogen, Ci-C ₂ -alkyl or C ₁ -C ₂ - halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ³

wherein

R ⁴ to R ⁶ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the more preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

wherein A represents a heterocycle of formula A ² )

(A ² )

wherein

R ¹ to R ³ independently from each other represent hydrogen, halogen, Ci-C ₂ -alkyl or C ₁ -C ₂ - halogenoalkyl comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ³ )

- -

(A ³ )

wherein

R ⁴ to R ⁶ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the even more preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

wherein A represents a heterocycle of formula A ⁵ )

(A ⁵ )

wherein

R ⁹ to R ¹¹ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-alkoxy, Ci- C i-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C i-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁶

(A ⁶ )

wherein

R ¹² and R ¹³ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-alkoxy, Ci- C i-halogenoalkyl comprising 1 to 9 halogen atoms, and

R ¹⁴ represents hydrogen, halogen, Ci-C i-alkyl, Ci-C i-alkoxyor Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

wherein A represents a heterocycle of formula (A ⁵ ) - -

(A ⁵ )

wherein

R ⁹ to R ¹¹ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C4-alkoxy, Ci- C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁶

(A ⁶ )

wherein

R ¹² and R ¹³ independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-halogenoalkyl comprising 1 to 9 halogen atoms, and

R ¹⁴ represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxyor Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the more preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

wherein A represents a heterocycle of formula A ⁵ )

(A ⁵ )

wherein

R ⁹ to R ¹¹ independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or

A represents a heterocycle of formula (A ⁶ ) - -

(A ⁶ )

wherein

R ¹² and R ¹³ independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-alkoxy, Ci- C4-halogenoalkyl comprising 1 to 9 halogen atoms, and

R ¹⁴ represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxyor Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the even more preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

wherein A is a heterocycle of formula A ²⁷ )

in which

R ⁶⁶ represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, and Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, and

R ⁶⁷ , R ⁶⁸ and R ⁶⁹ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C ₁ -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or

A is a heterocycle of formula (A ²⁸ )

in which

R ⁷⁰ represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms and

R ⁷¹ , R ⁷² and R ⁷³ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C ₁ -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen - 5- atoms;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

wherein A is a heterocycle of formula A )

in which

R ⁶⁶ represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, and Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, and

R ⁶⁷ , R ⁶⁸ and R ⁶⁹ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or

A is a heterocycle of formula (A ²⁸ )

in which

R ⁷⁰ represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms and

R ⁷¹ , R ⁷² and R ⁷³ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms;

Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the more preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

wherein A is a heterocycle of formula (A ²⁷ ) - -

in which

R ⁶⁶ represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, and Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, and

R ⁶⁷ , R ⁶⁸ and R ⁶⁹ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or

A is a heterocycle of formula (A ²⁸ )

in which

R ⁷⁰ represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms and

R ⁷¹ , R ⁷² and R ⁷³ independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; Y ² , Y ³ , Y ⁴ and Y ⁵ independently from each other represent hydrogen or Y ¹ ;

n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the even more preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

wherein A is a heterocycle of formula (A ³³

in which

R ⁸³ represents hydrogen, halogen, Ci-C2-alkyl or Ci-C2-halogenoalkyl having 1 to 5 halogen atoms; n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound, - 7- wherein A is a heterocycle of formula (A

in which

R ⁸³ represents hydrogen, halogen, Ci-C ₂ -alkyl or Ci-C ₂ -halogenoalkyl having 1 to 5 halogen atoms; n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the more preferred meaning described above.

In one embodiment the compound of formula (I) as defined above is a compound,

Wherein A is a heterocycle of formula (A ³³

in which

R ⁸³ represents hydrogen, halogen, Ci-C ₂ -alkyl or Ci-C ₂ -halogenoalkyl having 1 to 5 halogen atoms; n, X, Z ¹ and Z ² , Z ³ and Z ⁴ , Z ^a and Q have the even more preferred meaning described above.

Any preferred embodiments of Q as shown below can be combined with the general, preferred, more preferred, even more preferred, most preferred or most particularly preferred definition for a compound according to formula (I).

More preferably Q represents halogen, cyano, nitro, Ci- C i-alkyl, Ci- C i-halogenoalkyl having 1 to 5 halogen atoms, Ci-C i-alkoxy, Ci- C i-halogenoalkoxy having 1 to 9 halogen atoms, tri-(Ci-C4-alkyl)- silyl, tri-(Ci-C4-alkyl)-silyl-Ci-C4-alkyl, Ci-C4-alkoxyimino-Ci-C4-alkyl, (benzyloxyimino)-Ci-C4-alkyl.

Even more preferred Q represents halogen, cyano, nitro, Ci- C4-alkyl, Ci- C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci- C4-halogenoalkoxy having 1 to 9 halogen atoms, tri-(Ci-C4-alkyl)- silyl, tri-(Ci-C ₄ -alkyl)-silyl-Ci-C ₄ -alkyl.

Most preferred Q represents halogen, cyano, Ci- C3-alkyl, Ci- C3-halogenoalkyl having 1 to 5 halogen atoms, Ci-C3-alkoxy, Ci- C3-halogenoalkoxy having 1 to 9 halogen atoms.

Most particularly preferred Q represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, fluoromethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy. Compounds mentioned in the invention can be prepared according to a process PI as herein-defined that comprises reaction of an amine of formula (II- 1) or one of its salts:

(11-1 ) in which Z ¹ , Z ² , Z ³ , Z ⁴ , Z ^a , X and n have the meanings mentioned above for the compounds of formula (I), with a carboxylic acid derivative of formula (III-l):

(MM ) wherein A ^b represents A ^a or represents a heterocycle selected from the group consisting of A ¹ to A ¹² and A ¹⁴ to A ³³ and

L ¹ represents a leaving group selected in the list consisting of a halogen atom, a hydroxyl group, -OR ^a , - OC(=0)R ^a , R ^a being substituted or non-substituted Ci-C6-alkyl, substituted or non-substituted C1-C6- haloalkyl, benzyl, 4-methoxybenzyl or pentafluorophenyl, or a group of formula 0-C(=0)A ^b , in the presence of a catalyst and in the presence of a condensing agent in case L ¹ represents a hydroxyl group, and in the presence of an acid binder in case L ¹ represents a halogen atom.

Amine derivatives of formula (II- 1) are known or can be prepared by known processes.

Carboxylic acid derivatives of formula (III-l) are known or can be prepared by known processes.

In case L ¹ represents a hydroxy group, process PI according to the present invention is conducted in the presence of condensing agent. Suitable condensing agent may be selected in the non limited list consisting of acid halide former, such as phosgene, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide or thionyl chloride; anhydride former, such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as Ν,Ν'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorous pentoxide, polyphosphoric acid, N,N'-carbonyl- - - diimidazole, 2-ethoxy-N-ethoxycarbonyl- 1 ,2-dihydroquinoline (EEDQ), triphenylphosphine/tetrachloro- methane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholiniuni chloride hydrate, bromotripyrrolidino-phosphoniumhexafluorophosphate or propanephosphonic anhydride (T3P). Process PI according to the present invention is conducted in the presence of a catalyst. Suitable catalyst may be selected in the list consisting of N,N-dimethylpyridin-4-amine, 1 -hydroxy-benzotriazole or N,N- dimethylformamide.

In case L ¹ represents a halogen atom, process PI according to the present invention is conducted in the presence of an acid binder. Suitable acid binders for carrying out process PI according to the invention are in each case all inorganic and organic bases that are customary for such reactions. Preference is given to using alkaline earth metal, alkali metal hydride, alkali metal hydroxides or alkali metal alkoxides, such as sodium hydroxide, sodium hydride, calcium hydroxide, potassium hydroxide, potassium tert-butoxide or other ammonium hydroxide, alkali metal carbonates, such as caesium carbonate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate and also tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N- dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylpyridin-4-amine, diazabicyclooctane (DABCO), diazabicyclo-nonene (DBN) or diazabicycloundecene (DBU).

It is also possible to work in the absence of an additional condensing agent or to employ an excess of the amine component, so that it simultaneously acts as acid binder agent.

Suitable solvents for carrying out process PI according to the invention can be customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichlorethane or trichlorethane; ethers, such as diethyl ether, diisopropyl ether, methyl t- butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1 ,2-dimethoxyethane, 1 ,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone, or hexamethylphosphoric triamide; alcohols such as methanol, ethanol, propanol, iso-propanol; esters, such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide, or sulfones, such as sulfolane.

When carrying out process PI according to the invention, the amine derivative of formula (II) can be employed as its salt, such as chlorhydrate or any other convenient salt. ₅

When carrying out process PI according to the invention, 1 mole or an excess of the amine derivative of formula (II) and from 1 to 3 moles of the acid binder can be employed per mole of the reagent of formula (III).

It is also possible to employ the reaction components in other ratios. Work-up is carried out by known methods.

Process PI is generally carried out under atmospheric pressure. It is also possible to operate under elevated or reduced pressure.

When carrying out process PI, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures from 0 °C to 200 °C, preferably from 10 °C to 160 °C. A way to control the temperature for the process according to the invention is to use microwave technology.

In general, the reaction mixture is concentrated under reduced pressure. The residue that remains can be freed by known methods, such as chromatography or crystallization, from any impurities that can still be present.

The compound can be prepared according to the general processes of preparation described above. It will nevertheless be understood that, on the basis of his general knowledge and of available publications, the skilled worker will be able to adapt this method according to the specifics of each of the compounds, which it is desired to synthesize.

Methods and uses

The invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to the microorganisms and/or in their habitat.

The invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to the plant or plant parts.

The invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to plant propagation material.

The invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to the seed.

The invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied the soil on which the plants are grown or intended to be grown. ₅

The invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to the microorganisms and/or in their habitat.

The invention also relates to a method for controlling phytopathogenic fungi, characterized in that a compound of the formula (I) is applied to the plant or plant parts.

The invention also relates to a method for controlling phytopathogenic fungi, characterized in that a compound of the formula (I) is applied to plant propagation material.

The invention also relates to a method for controlling phytopathogenic fungi, characterized in that a compound of the formula (I) is applied to the seed.

The invention also relates to a method for controlling phytopathogenic fungi, characterized in a compound of the formula (I) is applied the soil on which the plants are grown or intended to be grown.

The invention also relates to a method for controlling phytopathogenic bacteria, characterized in that a compound of the formula (I) is applied to the plant or plant parts.

The invention also relates to a method for controlling phytopathogenic bacteria, characterized in that a compound of the formula (I) is applied to plant propagation material.

The invention also relates to a method for controlling phytopathogenic bacteria, characterized in that a compound of the formula (I) is are applied to the seed.

The invention also relates to a method for controlling phytopathogenic bacteria, characterized in that a compound of the formula (I) is applied the soil on which the plants are grown or intended to be grown.

The invention further relates to seed which has been treated with at least one compound of the formula (I).

The invention finally provides a method for protecting seed against phytopathogenic microorganisms by using seed treated with at least one compound of the formula (I).

The compounds of the formula (I) have potent microbicidal activity and can be used for control of phytopathogenic microorganisms in agriculture.

In one embodiment a compound of the formula (I) can be used for control of phytopathogenic microorganisms in crop protection and in the protection of materials.

The compounds of the formula (I) have potent microbicidal activity and can be used for control of phytopathogenic fungi in agriculture. ₅

In one embodiment a compound of the formula (I) can be used for control of phytopathogenic fungi in crop protection and in the protection of materials.

The compounds of the formula (I) have potent microbicidal activity and can be used for control of phytopathogenic bacteria in agriculture.

In one embodiment a compound of the formula (I) can be used for control of phytopathogenic bacteria in crop protection and in the protection of materials.

The compounds of the formula (I) can be used for curative or protective control of phytopathogenic microorganisms. The invention therefore also relates to curative and protective methods for controlling phytopathogenic microorganisms by the use of the inventive active ingredients or compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.

The compounds of the formula (I) can be used for curative or protective control of phytopathogenic bacteria. The invention therefore also relates to curative and protective methods for controlling phytopathogenic bacteria by the use of the inventive active ingredients or compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.

The compounds of the formula (I) can be used for curative or protective control of phytopathogenic fungi. The invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the inventive active ingredients or compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.

Plants

All plants and plant parts can be treated in accordance with the invention. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders' rights. Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples of which include leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.

Plants which can be treated in accordance with the invention include the following plants from the group of the useful plants, ornamentals, turfs, generally used trees which are employed as ornamentals in the public ₅ and domestic sectors, and forestry trees. Forestry trees comprise trees for the production of timber, cellulose, paper and products made from parts of the trees.

The term useful plants as used in the present context refers to crop plants which are employed as plants for obtaining foodstuffs, feedstuffs, fuels or for industrial purposes.

The useful plants include for example the following types of plants: turf, vines, cereals, for example wheat, barley, rye, oats, rice, maize and millet/sorghum, corn, maize; beet, for example sugar beet and fodder beet; fruits, for example pome fruit, stone fruit and soft fruit, for example apples, pears, plums, peaches, almonds, cherries and berries, for example strawberries, raspberries, blackberries; legumes, for example beans, lentils, peas and soybeans; oil crops, for example oilseed rape, canola, mustard, poppies, olives, sunflowers, coconuts, castor oil plants, cacao and peanuts; cucurbits, for example pumpkin/squash, cucumbers and melons; fibre plants, for example cotton, flax, hemp and jute; citrus fruit, for example oranges, lemons, grapefruit and tangerines; vegetables, for example spinach, lettuce, asparagus, cabbage species, carrots, onions, tomatoes, potatoes and bell peppers; Lauraceae, for example avocado, Cinnamomum, camphor, or else plants such as tobacco, nuts, coffee, aubergine, sugar cane, tea, pepper, grapevines, hops, bananas, latex plants and ornamentals, for example flowers, shrubs, deciduous trees and coniferous trees. This enumeration is no limitation.

The following plants are considered to be particularly suitable target crops: cotton, aubergine, turf, pome fruit, stone fruit, soft fruit, maize, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, beans, soybeans, oilseed rape, tomato, bell pepper, melons, cabbage, potato and apple.

Examples of trees are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp..

Examples of turf grasses are including cool-season turf grasses and warm-season turf grasses.

Cold-season turf grasses are bluegrasses (Poa spp.), such as Kentucky bluegrass (Poa pratensis L.), rough bluegrass (Poa trivialis L.), Canada bluegrass (Poa compressa L.), annual bluegrass (Poa annua L.), upland bluegrass (Poa glaucantha Gaudin), wood bluegrass (Poa nemoralis L.) and bulbous bluegrass (Poa bulbosa L.); bentgrasses (Agrostis spp.) such as creeping bentgrass (Agrostis palustris Huds.), colonial bentgrass (Agrostis tenuis Sibth.), velvet bentgrass (Agrostis canina L.), South German mixed bentgrass (Agrostis spp. including Agrostis tenuis Sibth., Agrostis canina L., and Agrostis palustris Huds.), and redtop (Agrostis alba L.); fescues (Festuca spp.), such as red fescue (Festuca rubra L. spp. rubra), creeping fescue (Festuca rubra L.), chewings fescue (Festuca rubra commutata Gaud.), sheep fescue (Festuca ovina L.), hard fescue (Festuca ₅ longifolia Thuill.), hair fescue (Festucu capillata Lara), tall fescue (Festuca arundinacea Schreb.) and meadow fescue (Festuca elanor L.); ryegrasses (Lolium spp.), such as annual ryegrass (Lolium multiflorum Lara), perennial ryegrass (Lolium perenne L.) and Italian ryegrass (Lolium multiflorum Lam.); and wheatgrasses (Agropyron spp.), such as fairway wheatgrass (Agropyron cristatum (L.) Gaertn.), crested wheatgrass (Agropyron desertorum (Fisch.) Schult.) and western wheatgrass (Agropyron smithii Rydb.); and further cool-season turf grasses like beachgrass (Ammophila breviligulata Fern.), smooth bromegrass (Bromus inermis Leyss.), cattails such as timothy (Phleum pratense L.), sand cattail (Phleum subulatum L.), orchardgrass (Dactylis glomerata L.), weeping alkaligrass (Puccinellia distans (L.) Pari.) and crested dog's- tail (Cynosurus cristatus L.).

Warm-season turf grasses are Bermuda grass (Cynodon spp. L. C. Rich), zoysia grass (Zoysia spp. Willd.), St. Augustine grass (Stenotaphrum secundatum Walt Kuntze), centipede grass (Eremochloa ophiuroides Munro Hack.), carpetgrass (Axonopus affinis Chase), Bahia grass (Paspalum notatum Flugge), Kikuyu grass (Pennisetum clandestinum Hochst. ex Chiov.), buffalo grass (Buchloe dactyloids (Nutt.) Engelm.), blue grama (Bouteloua gracilis (H.B.K.) Lag. ex Griffiths), seashore paspalum (Paspalum vaginatum Swartz) and sideoats grama (Bouteloua curtipendula (Michx. Torr.).

Pathogens

Non-limiting examples of phytopathogenic microorganisms, in particular phytopathogenic fungi which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis; Uromyces species, for example Uromyces appendiculatus; diseases caused by pathogens from the group of the Oomycetes, for example Albugo species, for example Albugo Candida; Bremia species, for example Bremia lactucae; Peronospora species, for example Peronospora pisi or P. brassicae; Phytophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum; leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe cirri; Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignardia bidwelli; Leptosphaeria species, for example Leptosphaeria maculans; Magnaporthe species, for example Magnaporthe grisea; Microdochium species, for example Microdochium nivale; Mycosphaerella species, for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis; Phaeosphaeria species, for example Phaeosphaeria nodorum; Pyrenophora species, for example Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species, for example Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii or Septoria lycopersici; Stagonospora species, for example Stagonospora nodorum; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis; root and stem diseases caused, for example, by Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Plasmodiophora species, for example Plasmodiophora brassicae; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae; Sclerotium species, for example Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; Thielaviopsis species, for example Thielaviopsis basicola; ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, for example Alternaria spp.; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium cladosporioides; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Stagnospora species, for example Stagnospora nodorum; diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries or Tilletia controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Ustilago nuda; fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicillium expansum or Penicillium -5 - purpurogenum; Rhizopus species, for example Rhizopus stolonifer; Sclerotinia species, for example Sclerotinia sclerotiorum; Verticilium species, for example Verticilium alboatrum; seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Macrophomina species, for example Macrophomina phaseolina; Microdochium species, for example Microdochium nivale; Monographella species, for example Monographella nivalis; Penicillium species, for example Penicillium expansum; Phoma species, for example Phoma lingam; Phomopsis species, for example Phomopsis sojae; Phytophthora species, for example Phytophthora cactoram; Pyrenophora species, for example Pyrenophora graminea; Pyricularia species, for example Pyricularia oryzae; Pythium species, for example Pythium ultimum; Rhizoctonia species, for example Rhizoctonia solani; Rhizopus species, for example Rhizopus oryzae; Sclerotium species, for example Sclerotium rolfsii; Septoria species, for example Septoria nodoram; Typhula species, for example Typhula incarnata; Verticillium species, for example Verticillium dahliae; cancers, galls and witches' broom caused, for example, by Nectria species, for example Nectria galligena; wilt diseases caused, for example, by Monilinia species, for example Monilinia laxa; deformations of leaves, flowers and fruits caused, for example, by Exobasidium species, for example Exobasidium vexans; Taphrina species, for example Taphrina deformans; degenerative diseases in woody plants, caused, for example, by Esca species, for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, for example Ganoderma boninense; diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea; diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani; diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas campestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae pv. lachrymans; Erwinia species, for example Erwinia amylovora. Preference is given to controlling the following diseases of soya beans:

Fungal diseases on leaves, stems, pods and seeds caused, for example, by Alternaria leaf spot (Alternaria spec, atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).

Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).

Mycotoxins

In addition, the compounds of the formula (I) can reduce the mycotoxin content in the plant products, in particular harvested material and the foods and feeds prepared therefrom. Mycotoxins include particularly, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac- DON, T2- and HT2 -toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec, such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae),

F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides etc., and also by Aspergillus spec, such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec, such as C.

purpurea, C.fusiformis, C. paspali, C. africana, Stachybotrys spec, and others. ₅

Material Protection

The compounds of the formula (I) can also be used in the protection of materials, for protection of industrial materials against attack and destruction by phytopathogenic microorganisms, in particular phytopathogenic fungi .

In addition, the compounds of the formula (I) can be used as antifouling compositions, alone or in combinations with other active ingredients.

Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry. For example, industrial materials which are to be protected by inventive compositions from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms. Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.

The compounds of the formula (I) may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.

In the case of treatment of wood the compounds of the formula (I) may also be used against fungal diseases liable to grow on or inside timber. The term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.

In addition, the compounds of the formula (I) can be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.

The compounds of the formula (I) can also be employed for protecting storage goods. Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired. Storage goods of vegetable origin, for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting. Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture. Storage goods of animal origin are, for example, hides, leather, furs and hairs. The inventive compositions may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.

Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The compounds of the formula (I) preferably act against fungi, especially ₅ moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp. and Saccharomyces spp., such as Saccharomyces cerevisae.

Formulations

The present invention further relates to a composition for controlling phytopathogenic microorganisms, in particular phytopathogenic fungi comprising at least one of the compounds of the formula (I). These are preferably fungicidal compositions which comprise agriculturally suitable auxiliaries, solvents, carriers, surfactants or extenders.

According to the invention, a carrier is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, in particular for application to plants or plant parts or seed. The carrier, which may be solid or liquid, is generally inert and should be suitable for use in agriculture.

Useful solid carriers include: for example ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates; useful solid carriers for granules include: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic flours, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/or foam-formers include: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP ethers, acid and/or POP POE esters, alkylaryl and/or POP POE ethers, fat and/or POP POE adducts, POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl or aryl phosphates or the corresponding PO-ether adducts. Additionally suitable are oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly)alcohols or (poly)amines. It is also possible to use lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and also their adducts with formaldehyde.

The active ingredients can be converted to the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with active ingredient, synthetic substances impregnated with active ingredient, fertilizers and also microencapsulations in polymeric substances.

The active ingredients can be applied as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with active ingredient, synthetic substances impregnated with active ingredient, fertilizers and also microencapsulations in polymeric substances. Application is accomplished in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation/the active ingredient itself into the soil. It is also possible to treat the seed of the plants.

The formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one customary extender, solvent or diluent, emulsifier, dispersant and/or binder or fixing agent, wetting agent, a water repellent, if appropriate siccatives and UV stabilizers and if appropriate dyes and pigments, antifoams, preservatives, secondary thickeners, stickers, gibberellins and also other processing auxiliaries.

The present invention includes not only formulations which are already ready for use and can be deployed with a suitable apparatus to the plant or the seed, but also commercial concentrates which have to be diluted with water prior to use.

The compounds of the formula (I) may be present as such or in their (commercial) formulations and in the use forms prepared from these formulations as a mixture with other (known) active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and/or semiochemicals.

The auxiliaries used may be those substances which are suitable for imparting particular properties to the composition itself or and/or to preparations derived therefrom (for example spray liquors, seed dressings), such as certain technical properties and/or also particular biological properties. Typical auxiliaries include: extenders, solvents and carriers.

Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the - - classes of the aromatic and nonaromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which may optionally also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).

Liquefied gaseous extenders or carriers are understood to mean liquids which are gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, or else butane, propane, nitrogen and carbon dioxide.

In the formulations it is possible to use tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Further additives may be mineral and vegetable oils.

If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.

Compositions comprising compounds of the formula (I) may additionally comprise further components, for example surfactants. Suitable surfactants are emulsifiers and/or foam formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants. Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignosulphite waste liquors and methylcellulose. The presence of a surfactant is necessary if one of the active ingredients and/or one of the inert carriers is insoluble in water and when application is effected in water. The proportion of surfactants is between 5 and 40 per cent by weight of the inventive composition.

It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Further additives may be perfumes, mineral or vegetable, optionally modified oils, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Additional components may be stabilizers, such as cold stabilizers, preservatives, antioxidants, light stabilizers, or other agents which improve chemical and/or physical stability.

If appropriate, other additional components may also be present, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complex formers. In general, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.

The formulations contain generally between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, more preferably between 0.5 and 90%> of active ingredient, most preferably between 10 and 70 per cent by weight.

The formulations described above can be used for controlling phytopathogenic microorganisms, in which the compositions comprising compounds of the formula (I) are applied to the phytopathogenic microorganisms and/or in their habitat.

Seed Treatment

The invention furthermore includes a method for treating seed.

A further aspect of the present invention relates in particular to seeds (dormant, primed, pregerminated or even with emerged roots and leaves) treated with at least one of the compounds of the formula (I). The inventive seeds are used in methods for protection of seeds and emerged plants from the seeds from phytopathogenic microorganisms, in particular phytopathogenic fungi. In these methods, seed treated with at least one inventive active ingredient is used.

The compounds of the formula (I) are also suitable for the treatment of seeds and young seedlings. A large part of the damage to crop plants caused by harmful organisms is triggered by the infection of the seeds before sowing or after germination of the plant. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive, and even small damage may result in the death of the plant. Accordingly, there is great interest in protecting the seed and the germinating plant by using appropriate compositions.

It is also desirable to optimize the amount of the active ingredient used so as to provide the best possible protection for the seeds, the germinating plants and emerged seedlings from attack by phytopathogenic fungi, but without damaging the plants themselves by the active ingredient used. In particular, methods for the treatment of seed should also take into consideration the intrinsic phenotypes of transgenic plants -oi- in order to achieve optimum protection of the seed and the germinating plant with a minimum of crop protection compositions being employed.

The present invention therefore also relates to a method for protecting seeds, germinating plants and emerged seedlings against attack by animal pests and/or phytopathogenic microorganisms, in particular phytopathogenic fungi by treating the seeds with an inventive composition. The invention also relates to the use of the compositions according to the invention for treating seeds for protecting the seeds, the germinating plants and emerged seedlings against animal pests and/or phytopathogenic microorganisms, in particular phytopathogenic fungimicro. The invention further relates to seeds which has been treated with an inventive composition for protection from animal pests and/or phytopathogenic microorganisms, in particular phytopathogenic fungi.

One of the advantages of the present invention is thatthe treatment of the seeds with these compositions not only protects the seed itself, but also the resulting plants after emergence, from animal pests and/or phytopathogenic harmful microorganisms. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter protect plants as well as seed treatment in prior to sowing.lt is likewise considered to be advantageous that the inventive active ingredients or compositions can be used especially also for transgenic seed, in which case the plant which grows from this seed is capable of expressing a protein which acts against pests, herbicidal damage or abiotic stress. The treatment of such seeds with the inventive active ingredients or compositions, for example an insecticidal protein, can result in control of certain pests. Surprisingly, a further synergistic effect can be observed in this case, which additionally increases the effectiveness for protection against attack by pests., microorganisms, weeds or abiotic stress.

The compounds of the formula (I) are suitable for protection of seed of any plant variety which is used in agriculture, in the greenhouse, in forests or in horticulture. More particularly, the seed is that of cereals (such as wheat, barley, rye, millet and oats), oilseed rape, maize, cotton, soybeen, rice, potatoes, sunflower, beans, coffee, beet (e.g. sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onions and lettuce), lawns and ornamental plants. Of particular significance is the treatment of the seed ofwheat, soybean, oilseed rape, maize and rice.

As also described below, the treatment of transgenic seed with the inventive active ingredients or compositions is of particular significance. This refers to the seed of plants containing at least one heterologous gene which allows the expression of a polypeptide or protein, e.g. having insecticidal properties. These heterologous genes in transgenic seeds may originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. These heterologous genes preferably originates from Bacillus sp., in which case the gene product is effective against the European corn borer and/or the Western corn rootworm. Particularly preferably, the heterologous genes originate from Bacillus thuringiensis. In the context of the present invention, the inventive composition is applied to seeds either alone or in a suitable formulation. Preferably, the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment. In general, seeds can be treated at any time between harvest and some time after sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seed which, after drying, for example, has been treated with water and then dried again, or seeds just after priming, or seeds stored in primed conditions or pre- germinated seeds, or seeds sown on nursery trays, tapes or paper.

When treating the seeds, it generally has to be ensured that the amount of the inventive composition applied to the seed and/or the amount of further additives is selected such that the germination of the seed is not impaired, or that the resulting plant is not damaged. This must be ensured particularly in the case of active ingredients which can exhibit phytotoxic effects at certain application rates.

The compounds of the formula (I) can be applied directly, i.e. without containing any other components and without having been diluted. In general, it is preferable to apply the compositions to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art. The compounds of the formula (I) can be converted to the customary formulations relevant to on-seed applications, such as solutions, emulsions, suspensions, powders, foams, slurries or combined with other coating compositions for seed, such as film forming materials, pelleting materials, fine iron or other metal powders, granules, coating material for inactivated seeds, and also ULV formulations.

These formulations are prepared in a known manner, by mixing the active ingredients or active ingredient combinations with customary additives, for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins, and also water.

Useful dyes which may be present in the seed dressing formulations usable in accordance with the invention are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting and which are conventionally used for the formulation of active agrochemical ingredients. Usable with preference are alkylnaphthalenesulphonates, such as diisopropyl- or diisobutylnaphthalenesulphonates. Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Useful nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulphated derivatives thereof. Suitable anionic dispersants are especially lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates.

Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.

Adhesives which may be present in the seed dressing formulations usable in accordance with the invention are all customary binders usable in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The formulations for on-seed applications usable in accordance with the invention can be used to treat a wide variety of different kinds of seed either directly or after prior dilution with water. For instance, the concentrates or the preparations obtainable therefrom by dilution with water can be used to dress the seed of cereals, such as wheat, barley, rye, oats, and triticale, and also seeds of maize, soybean, rice, oilseed rape, peas, beans, cotton, sunflowers, and beets, or else a wide variety of different vegetable seeds. The formulations usable in accordance with the invention, or the dilute preparations thereof, can also be used for seeds of transgenic plants. In this case, additional synergistic effects may also occur in interaction with the substances formed by expression.

For treatment of seeds with the formulations usable in accordance with the invention, or the preparations prepared therefrom by adding water, all mixing units usable customarily for on-seed applications are useful. Specifically, the procedure in on-seed applications is to place the seeds into a mixer, to add the particular desired amount of the formulations, either as such or after prior dilution with water, and to -comix everything until all applied formulations are distributed homogeneously on the seeds. If appropriate, this is followed by a drying operation.

The application rate of the formulations usable in accordance with the invention can be varied within a relatively wide range. It is guided by the particular content of the active ingredients in the formulations and by the seeds. The application rates of each single active ingredient is generally between 0.001 and 15 g per kilogram of seed, preferably between 0.01 and 5 g per kilogram of seed.

GMO

As already mentioned above, it is possible to treat all plants and their parts in accordance with the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms "parts" or "parts of plants" or "plant parts" have been explained above. More preferably, plants of the plant cultivars which are commercially available or are in use are treated in accordance with the invention. Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.

The method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants of which a heterologous gene has been stably integrated into genome. The expression "heterologous gene" essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference - RNAi - technology or microRNA - miRNA - technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids. _n

-67-

Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to the invention, are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content and composition for example cotton or starch, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.

Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. - -

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as Tobacco plants, with altered post-translational protein modification patterns.

Application Rates

When using the compounds of the formula (I) as fungicides, the application rates can be varied within a relatively wide range, depending on the kind of application. The application rate of the inventive active ingredients is

• in the case of treatment of plant parts, for example leaves: from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 50 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used);

• in the case of seed treatment: from 0.1 to 200 g per 100 kg of seed, preferably from 1 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12.5 g per 100 kg of seed;

• in the case of soil treatment: from 0.1 to 10 000 g/ha, preferably from 1 to 5000 g/ha. - -

These application rates are merely by way of example and are not limiting for the purposes of the invention.

-7 -

The preferred and exemplary compounds according to the invention listed in Table 1 can be synthesized analogous to the above mentioned processes.

The examples shown below further illustrate the invention without limiting it.

Preferred compounds of formula (I) according to the present invention are listed in the following table 1.

Table 1

Ex

N° X ¹ X ² X ³ X ⁴ X ^s z ¹ Z ² Z ³ Z ⁴ Z ^a A LogP

1 H H CI H H H H H H CH ₃ 2 -fluorophenyl 3,32^

2 H H CI H H H H H H CH ₃ 3-iodo-2-thienyl 3,85M

3 H H CI H CI H H H H CH ₃ 3-iodo-2-thienyl 4,45 M

4 CI H CI H CI H H H H CH ₃ 3-iodo-2-thienyl 5,02^

5 H H CI H H H H H H CH ₃ 3-bromo-2-furyl 3,32^

6 H H CI H CI H H H H CH ₃ 3-bromo-2-furyl 3,85M

7 CI H CI H CI H H H H CH ₃ 3-bromo-2-furyl 4 _; 40M

8 H H CI H CI H H H H CH ₃ 2-iodophenyl 4,28^

9 CI H CI H CI H H H H CH ₃ 2-bromophenyl 4j4M

10 H H CI H H H H H H CH ₃ 2-bromophenyl 3,61M

11 H H CI H CI H H H H CH ₃ 2-bromophenyl 4, 11 ^[a]

12 CI H CI H CI H H H H CH ₃ 3 -chloro -2 -thienyl 4,80^

13 H H CI H H H H H H CH ₃ 3 -chloro -2 -thienyl 3,61M

14 H H CI H CI H H H H CH ₃ 3 -chloro -2 -thienyl 4,17 ^[a]

15 H H CI H CI H H H H CH ₃ 2-(trifluoromethyl)phenyl 4,34^

16 CI H CI H CI H H H H CH ₃ 2-(trifluoromethyl)phenyl 4,91 ^[a]

17 CI H CI H CI H H H H CH ₃ 2-iodophenyl 4,85^

18 H H CI H H H H H H CH ₃ 2-(trifluoromethyl)phenyl 3,80^

19 H H CI H H H H H H CH ₃ 2-chlorophenyl 3,56^

20 CI H CI H CI H H H H CH ₃ 2 ,6 -difluorophenyl 4,57 ^[a]

21 H H CI H CI H H H H CH ₃ 2 ,6 -difluorophenyl 4,00^

22 H H CI H H H H H H CH ₃ 2 ,6 -difluorophenyl 3,46^ -7 -

-7 -

-7 -

Measurement of LogP values was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following method:

^[a] LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

Calibration was done with straight-chain alkan2-ones (with 3 to 16 carbon atoms) with known LogP values (measurement of LogP values using retention times with linear interpolation between successive alkanones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.

NMR-Peak lists

1H-NMR data of selected examples are written in form of lH-NMR-peak lists. To each signal peak are listed the δ-value in ppm and the signal intensity in round brackets. Between the δ-value - signal intensity pairs are semicolons as delimiters.

The peak list of an example has therefore the form: δι (intensityi); 82 (intensity2); ; δ; (intensity); ; δ _η (intensity^

Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.

For calibrating chemical shift for 1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.

The 1H-NMR peak lists are similar to classical 1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation. Additionally they can show like classical IH-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.

To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D6 and the peak of water are shown in our IH-NMR peak lists and have usually on average a high intensity .

The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90 %).

Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via "side-products-fingerprints".

An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD- simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical IH-NMR interpretation.

Further details of NMR-data description with peak lists you find in the publication "Citation of NMR Peaklist Data within Patent Applications" of the Research Disclosure Database Number 564025.

Example 1 : ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.517 (2.6); 7.503 (3.9); 7.496 (5.8); 7.481 (5.9); 7.473 (5.1); 7.460 (3.5); 7.364 (9.8); 7.345 (16.0); 7.313 (4.8); 7.286 (12.8); 7.261 (15.0); 7.240 (13.2); 7.077 (0.3); 3.954 (2.7); 3.739 (0.5); 3.682 (0.5); 3.665 (1.0); 3.438 (6.7); 3.327 (221.3); 2.928 (5.8); 2.913 (9.5); 2.897 (5.7); 2.800 (0.4); 2.780 (0.4); 2.676 (0.9); 2.671 (1.2); 2.667 (0.9); 2.541 (2.7); 2.511 (74.9); 2.507 (139.9); 2.502 (176.4); 2.498 (126.7); 2.493 (61.5); 2.333 (0.8); 2.329 (1.1);

2.324 (0.8); 1.258 (0.3); 1.235 (0.7); 0.008 (1.3); 0.000 (29.4); -0.008 (1.1)

Example 2: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.778 (3.1); 7.765 (3.3); 7.356 (0.3); 7.350 (2.6); 7.345 (1.0); 7.334 (1.5); 7.329 (5.3); 7.323 (0.8); 7.313 (0.5); 7.283 (4.4); 7.262 (2.4); 7.231 (3.4); 7.218 (3.2); 3.935 (1.6); 3.918 (2.9); 3.900 (1.7); 3.611 (16.0); 3.437 (1.4); 3.382 (0.6); 3.341 (264.1); 3.308 (0.8); 2.934 (1.6); 2.917 (2.8); 2.899 (1.5); 2.676 (0.3); 2.671 (0.5); 2.667 (0.3); 2.542 (0.5); 2.525 (1.4); 2.511 (26.3); 2.507 (52.4); 2.502 (68.8); 2.498 (50.1); 2.493 (24.3); 2.329 (0.4)

Example 3: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.789 (3.3); 7.777 (3.4); 7.579 (2.4); 7.575 (2.4); 7.400 (0.9); 7.379 (3.9); 7.371 (2.9); 7.366 (2.6); 7.350 (0.6); 7.345 (0.6); 7.236 (3.6); 7.224 (3.4); 3.962 (1.5); 3.944 (3.0); 3.927 (1.6); 3.616 (16.0); 3.447 (0.4); 3.373 (0.5); 3.336 (233.6); 3.055 (1.7); 3.037 (3.0); 3.020 (1.5); 2.676 (0.4); 2.671 (0.5); 2.667 (0.4); 2.542 (0.9); 2.525 (1.5); 2.511 (28.7); 2.507 (56.7); 2.502 (73.9); 2.498 (53.1); 2.493 (25.4); 2.334 (0.4); 2.329 (0.5); 2.325 (0.4); 0.000

(2.0)

Example 4: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.813 (3.6); 7.800 (3.7); 7.670 (11.4); 7.258 (3.9); 7.245 (3.7); 3.922 (1.4); 3.904 (2.5); 3.886 (1.5); 3.617 (16.0); 3.332 (201.7); 3.237 (1.6); 3.219 (2.5); 3.202 (1.4); 2.676 (0.3); 2.671 (0.5); 2.667 (0.3); 2.542 (1.0); 2.525 (1.4); 2.520 (2.2); 2.511 (26.9); 2.507 (54.0); 2.502 (70.9); 2.498 (50.7); 2.493 (24.0); 2.329 (0.5); 2.324 (0.3);

0.000 (6.0)

Example 5: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.880 (2.9); 7.875 (2.9); 7.332 (2.4); 7.327 (0.9); 7.316 (1.2); 7.311 (4.5); 7.305 (0.6); 7.259 (3.5); 7.238 (1.9); 6.830 (3.1); 6.825 (3.1); 3.919 (1.6); 3.902 (2.8); 3.884 (1.7); 3.686 (16.0); 3.438 (0.4); 3.331 (40.5); 2.917 (1.4); 2.900 (2.4); 2.882 (1.3); 2.542 (0.4); 2.525 (0.4); 2.520 (0.6); 2.512 (7.3); 2.507 (14.6); 2.503 (19.2); 2.498 (13.7);

2.493 (6.4); 0.000 (2.7)

Example 6: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.874 (2.8); 7.869 (2.8); 7.546 (2.3); 7.343 (6.5); 7.341 (5.2); 6.829 (3.1); 6.824 (3.0); 3.955 (1.7); 3.938 (3.5); 3.921 (1.8); 3.698 (16.0); 3.330 (25.3); 3.035 (1.7); 3.017 (3.3); 3.000 (1.6); 2.543 (0.4); 2.512 (6.0); 2.508 (11.8);

2.503 (15.4); 2.499 (11.2); 2.495 (5.4); 0.000 (2.0)

Example 7: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.896 (3.0); 7.891 (3.0); 7.644 (7.7); 6.853 (3.1); 6.848 (3.1); 3.902 (1.6); 3.885 (3.0); 3.867 (1.7); 3.703 (16.0); 3.332 (23.2); 3.225 (1.7); 3.208 (2.9); 3.190 (1.5); 2.544 (0.4); 2.513 (5.2); 2.509 (10.2); 2.504 (13.3);

2.500 (9.7); 2.496 (4.7); 0.000 (1.3)

Example 8: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.874 (14.8); 7.872 (15.2); 7.854 (16.0); 7.853 (15.7); 7.627 (5.1); 7.564 (0.6); 7.559 (0.7); 7.517 (3.5); 7.497 (5.8); 7.473 (2.7); 7.453 (4.5); 7.436 (6.9); 7.414 (4.3); 7.392 (2.5); 7.362 (1.8); 7.357 (1.6); 7.341 (1.3); 7.336

(1.4) ; 7.322 (1.5); 7.265 (4.8); 7.248 (4.0); 7.193 (5.8); 7.190 (5.8); 7.173 (9.7); 7.171 (9.5); 7.155 (4.7); 7.151

(4.5) ; 6.711 (1.2); 3.968 (6.4); 3.952 (4.4); 3.853 (5.0); 3.692 (0.9); 3.666 (0.5); 3.646 (0.5); 3.627 (0.5); 3.585 (0.5); 3.549 (0.4); 3.497 (0.5); 3.449 (2.9); 3.406 (19.1); 3.362 (1.3); 3.330 (216.9); 3.290 (0.5); 3.136 (6.4); 2.952 (2.3); 2.908 (1.8); 2.677 (0.7); 2.672 (0.9); 2.668 (0.6); 2.542 (4.3); 2.526 (2.6); 2.512 (49.7); 2.508 (99.4); 2.503 (130.0); 2.499 (93.3); 2.494 (44.2); 2.334 (0.6); 2.330 (0.8); 2.325 (0.6); 1.258 (0.4); 1.249 (0.3); 1.234 (0.9);

0.008 (0.6); 0.000 (17.5); -0.009 (0.5)

Example 9: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.719 (16.0); 7.682 (8.3); 7.663 (8.1); 7.596 (4.2); 7.485 (1.5); 7.467 (4.3); 7.449 (4.5); 7.423 (6.3); 7.402 (10.6); 7.395 (6.9); 7.383 (9.5); 7.378 (7.4); 7.364 (3.2); 7.359 (2.5); 7.215 (1.5); 3.928 (4.3); 3.910 (6.6); 3.890 (5.0); 3.849 (7.4); 3.616 (0.4); 3.571 (0.6); 3.529 (0.7); 3.438 (27.6); 3.388 (1.0); 3.333 (343.1); 3.300 (7.1); 3.282 (4.7); 3.136 (2.6); 2.682 (0.4); 2.677 (0.7); 2.673 (1.0); 2.668 (0.7); 2.664 (0.3); 2.543 (4.1); 2.526 (3.2); 2.521 (5.0); 2.513 (59.0); 2.508 (117.0); 2.504 (152.1); 2.499 (108.0); 2.494 (50.4); 2.340 (0.3); 2.335 (0.7); 2.330 (1.0); 2.326 (0.7); 2.321 (0.3); 1.299 (0.4); 1.258 (0.5); 1.249 (0.4); 1.233 (1.0); 0.008 (0.6); 0.000 (16.9); -0.009 (0.5) Example 10: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.656 (9.1); 7.634 (10.7); 7.453 (1.4); 7.435 (3.1); 7.417 (2.7); 7.374 (15.8); 7.370 (16.0); 7.362 (12.6); 7.356 (13.8); 7.351 (12.4); 7.336 (6.8); 7.332 (6.0); 7.312 (2.2); 7.293 (4.1); 7.275 (3.0); 7.049 (1.0); 6.704 (0.5); 3.993 (3.2); 3.976 (5.5); 3.959 (3.5); 3.819 (2.0); 3.666 (0.3); 3.493 (0.3); 3.483 (0.4); 3.438 (1.1); 3.399 (17.5); 3.335 (361.4); 3.287 (0.5); 3.276 (0.4); 2.997 (3.4); 2.979 (5.6); 2.962 (3.5); 2.925 (0.4); 2.893 (0.4); 2.868 (0.5); 2.832 (0.9); 2.676 (0.6); 2.672 (0.9); 2.667 (0.6); 2.542 (3.2); 2.525 (2.4); 2.512 (49.3); 2.507 (98.4); 2.503 (128.8);

2.498 (93.0); 2.494 (44.6); 2.334 (0.6); 2.329 (0.8); 2.325 (0.6); 1.258 (0.4); 1.235 (0.6); 0.000 (6.1)

Example 11 : ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.666 (12.8); 7.644 (16.0); 7.623 (6.9); 7.565 (0.7); 7.560 (0.7); 7.503 (4.8); 7.483 (7.4); 7.467 (3.1); 7.447

(5.6) ; 7.430 (9.6); 7.413 (5.1); 7.386 (8.5); 7.382 (10.4); 7.367 (11.6); 7.363 (14.1); 7.348 (8.5); 7.343 (10.5); 7.321 (4.9); 7.275 (1.5); 6.817 (1.2); 4.008 (5.0); 3.991 (8.5); 3.973 (5.4); 3.837 (5.4); 3.692 (0.9); 3.662 (0.6); 3.653 (0.6); 3.639 (0.5); 3.608 (0.4); 3.591 (0.5); 3.566 (0.4); 3.535 (0.4); 3.498 (0.6); 3.449 (3.5); 3.412 (28.4); 3.334 (446.2); 3.281 (0.5); 3.273 (0.4); 3.261 (0.3); 3.122 (5.3); 3.105 (8.6); 3.088 (5.3); 2.946 (2.4); 2.908 (2.3); 2.681 (0.4); 2.677 (0.9); 2.672 (1.1); 2.668 (0.8); 2.663 (0.4); 2.542 (4.6); 2.526 (3.6); 2.521 (5.7); 2.512 (65.9); 2.508 (130.9); 2.503 (170.8); 2.499 (122.5); 2.494 (58.2); 2.339 (0.4); 2.334 (0.8); 2.330 (1.1); 2.325 (0.8); 2.321

(0.4); 1.299 (0.4); 1.258 (0.7); 1.249 (0.5); 1.234 (1.0); 0.008 (0.5); 0.000 (14.7); -0.008 (0.4)

Example 12: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.915 (4.0); 7.902 (4.1); 7.665 (11.2); 7.160 (4.1); 7.146 (4.0); 3.939 (1.5); 3.922 (2.7); 3.904 (1.6); 3.627 (16.0); 3.337 (49.4); 3.227 (1.6); 3.210 (2.6); 3.192 (1.4); 2.543 (0.5); 2.526 (0.3); 2.522 (0.5); 2.513 (6.1); 2.509

(12.3); 2.504 (16.1); 2.499 (11.5); 2.495 (5.4); 0.000 (1.0)

Example 13: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.881 (3.1); 7.868 (3.2); 7.344 (2.6); 7.339 (1.0); 7.328 (1.3); 7.323 (5.1); 7.317 (0.8); 7.279 (4.3); 7.274 (1.2); 7.262 (0.9); 7.258 (2.2); 7.134 (3.3); 7.121 (3.2); 3.951 (1.7); 3.934 (3.2); 3.916 (1.8); 3.620 (16.0); 3.331 (43.9); 2.926 (1.6); 2.908 (2.9); 2.891 (1.5); 2.542 (0.4); 2.525 (0.5); 2.511 (8.6); 2.507 (16.9); 2.502 (21.9); 2.498 (15.6);

2.493 (7.4); 0.000 (1.8)

Example 14: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.891 (3.1); 7.878 (3.2); 7.577 (2.2); 7.572 (2.2); 7.388 (0.7); 7.367 (4.0); 7.362 (3.1); 7.357 (2.6); 7.341 (0.4); 7.337 (0.5); 7.139 (3.3); 7.126 (3.2); 3.979 (1.6); 3.961 (3.4); 3.944 (1.7); 3.626 (16.0); 3.334 (162.2); 3.046 (1.7); 3.029 (3.3); 3.012 (1.6); 2.671 (0.4); 2.542 (0.5); 2.524 (1.3); 2.511 (22.0); 2.507 (42.2); 2.502 (54.2); 2.498 (39.0); 2.493 (18.7); 2.329 (0.4); 0.000 (2.0)

Example 15: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.815 (8.8); 7.795 (11.7); 7.769 (2.7); 7.751 (6.5); 7.732 (4.7); 7.689 (7.8); 7.670 (10.9); 7.651 (5.6); 7.635 (10.3); 7.631 (10.5); 7.566 (0.7); 7.561 (0.8); 7.505 (12.9); 7.484 (16.0); 7.437 (7.6); 7.433 (7.7); 7.412 (5.3); 7.393 (2.0); 7.380 (1.4); 7.363 (0.8); 7.358 (0.7); 7.343 (0.4); 7.338 (0.4); 7.299 (1.3); 7.279 (1.0); 6.952 (1.1); 6.936 (1.0); 3.978 (6.8); 3.960 (10.6); 3.941 (7.3); 3.804 (5.5); 3.691 (0.7); 3.604 (0.5); 3.555 (0.7); 3.509 (0.4); 3.497 (0.5); 3.448 (3.2); 3.437 (0.7); 3.376 (49.1); 3.329 (856.0); 3.277 (0.8); 3.250 (0.4); 3.193 (0.4); 3.074 (7.1); 3.056 (10.9); 3.037 (7.0); 2.947 (1.5); 2.907 (2.7); 2.680 (1.0); 2.676 (2.1); 2.671 (2.8); 2.667 (2.0); 2.662 (0.9); 2.542 (5.4); 2.525 (9.2); 2.511 (165.5); 2.507 (325.6); 2.502 (422.6); 2.498 (301.7); 2.493 (142.5); 2.338 (1.0); -7 -

2.334 (2.0); 2.329 (2.7); 2.325 (2.0); 2.320 (0.9); 1.336 (0.4); 1.298 (0.6); 1.258 (0.9); 1.249 (0.8); 1.235 (1.7);

0.008 (1.8); 0.000 (50.7); -0.009 (1.5)

Example 16: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.828 (3.8); 7.808 (4.2); 7.788 (1.4); 7.769 (3.4); 7.750 (2.8); 7.728 (16.0); 7.702 (4.6); 7.684 (4.0); 7.665

(1.5) ; 7.608 (2.3); 7.586 (3.7); 7.567 (3.1); 7.433 (0.7); 3.900 (3.1); 3.881 (4.4); 3.861 (3.5); 3.818 (3.7); 3.455 (0.8); 3.408 (25.9); 3.329 (436.8); 3.260 (3.7); 3.241 (4.7); 3.222 (3.5); 3.137 (0.8); 2.676 (1.1); 2.672 (1.5); 2.667

(1.1) ; 2.542 (4.6); 2.525 (7.3); 2.511 (86.9); 2.507 (169.8); 2.502 (221.5); 2.498 (161.2); 2.493 (78.7); 2.334 (1.0); 2.329 (1.4); 2.325 (1.0); 2.320 (0.5); 1.259 (0.4); 1.249 (0.4); 1.234 (0.9); 0.008 (1.0); 0.000 (25.6); -0.009 (0.9) Example 17: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.889 (11.0); 7.869 (11.4); 7.722 (16.0); 7.659 (0.6); 7.595 (5.6); 7.489 (2.4); 7.472 (5.1); 7.453 (3.8); 7.394 (2.3); 7.351 (5.4); 7.333 (4.4); 7.210 (9.0); 7.206 (9.3); 7.190 (14.9); 7.187 (14.9); 7.171 (8.0); 7.167 (7.9); 7.144

(2.2) ; 7.128 (1.9); 3.891 (8.8); 3.867 (12.7); 3.650 (0.5); 3.615 (0.5); 3.512 (1.1); 3.436 (28.1); 3.331 (171.7); 3.253 (0.7); 3.144 (3.7); 2.677 (0.6); 2.673 (0.8); 2.669 (0.6); 2.543 (5.3); 2.508 (97.8); 2.504 (124.2); 2.500 (93.1); 2.335 (0.6); 2.331 (0.8); 2.327 (0.6); 1.258 (0.4); 1.249 (0.4); 1.232 (1.0); 0.000 (13.5); -0.008 (0.6) Example 18: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.806 (8.1); 7.786 (10.7); 7.754 (1.9); 7.736 (4.5); 7.717 (3.4); 7.677 (5.1); 7.658 (6.8); 7.639 (2.9); 7.622 (0.5); 7.600 (0.5); 7.575 (0.6); 7.448 (4.9); 7.429 (4.5); 7.400 (5.5); 7.380 (15.8); 7.360 (16.0); 7.340 (6.2); 7.318

(1.6) ; 7.313 (2.8); 7.295 (0.5); 7.274 (0.4); 7.260 (2.0); 7.239 (1.2); 7.080 (1.1); 6.773 (0.6); 3.969 (5.0); 3.951 (8.0); 3.932 (5.4); 3.786 (2.6); 3.664 (1.7); 3.605 (0.3); 3.538 (0.5); 3.512 (0.4); 3.492 (0.4); 3.481 (0.4); 3.438 (7.2); 3.359 (35.4); 3.329 (918.3); 3.246 (0.4); 3.229 (0.3); 3.175 (0.4); 2.949 (5.2); 2.930 (8.2); 2.912 (5.4); 2.892 (1.6); 2.873 (1.4); 2.846 (0.8); 2.832 (0.9); 2.799 (1.2); 2.780 (1.1); 2.763 (0.5); 2.680 (1.2); 2.675 (2.2); 2.671 (3.0); 2.666 (2.2); 2.662 (1.1); 2.541 (2.9); 2.524 (11.3); 2.511 (180.3); 2.506 (348.1); 2.502 (447.8); 2.497 (320.7); 2.493 (153.1); 2.338 (1.0); 2.333 (2.1); 2.329 (2.9); 2.324 (2.0); 1.336 (0.3); 1.298 (0.6); 1.258 (0.9); 1.249 (0.7); 1.244 (0.6); 1.235 (1.7); 0.008 (1.9); 0.000 (47.3); -0.009 (1.5)

Example 19: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.505 (7.5); 7.501 (7.4); 7.484 (13.9); 7.482 (16.0); 7.457 (7.0); 7.452 (7.7); 7.439 (11.6); 7.434 (12.9); 7.419 (7.0); 7.414 (8.8); 7.387 (8.1); 7.367 (15.9); 7.355 (14.8); 7.317 (6.3); 7.043 (1.0); 6.762 (0.5); 3.988 (6.7); 3.811 (1.8); 3.679 (0.3); 3.656 (0.3); 3.645 (0.3); 3.579 (0.4); 3.527 (0.4); 3.513 (0.4); 3.495 (0.5); 3.481 (0.5); 3.398 (18.8); 3.331 (341.1); 3.282 (0.3); 2.962 (7.0); 2.829 (0.9); 2.680 (0.4); 2.676 (0.9); 2.671 (1.2); 2.667 (0.9); 2.662 (0.4); 2.542 (4.1); 2.525 (3.3); 2.520 (5.1); 2.511 (66.4); 2.507 (133.8); 2.502 (176.1); 2.498 (126.5); 2.493 (60.3); 2.338 (0.4); 2.334 (0.8); 2.329 (1.1); 2.324 (0.8); 2.320 (0.4); 1.258 (0.3); 1.234 (0.8); 0.008 (0.5); 0.000 (16.6); - 0.009 (0.5)

Example 20: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.707 (10.7); 7.599 (1.8); 7.588 (1.0); 7.584 (0.9); 7.567 (1.5); 7.550 (0.8); 7.546 (0.9); 7.529 (0.4); 7.245 (2.6); 7.225 (4.0); 7.205 (2.2); 7.198 (0.8); 3.986 (1.9); 3.967 (2.5); 3.948 (2.1); 3.839 (2.5); 3.605 (0.4); 3.587 (0.6); 3.569 (0.4); 3.501 (16.0); 3.330 (109.8); 3.261 (2.0); 3.241 (2.4); 3.223 (1.8); 3.150 (0.4); 3.131 (0.5); 3.113 (0.3); 2.672 (0.4); 2.542 (1.3); 2.525 (1.3); 2.520 (2.0); 2.512 (22.0); 2.507 (43.1); 2.503 (55.7); 2.498 (39.5);

2.494 (18.4); 2.330 (0.4); 0.000 (5.6)

Example 21 : ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.615 (2.8); 7.610 (3.2); 7.587 (0.5); 7.571 (0.9); 7.566 (1.0); 7.549 (1.6); 7.533 (0.9); 7.528 (1.0); 7.512 (0.4); 7.468 (0.4); 7.441 (1.5); 7.420 (3.5); 7.394 (2.5); 7.389 (2.5); 7.374 (1.1); 7.369 (1.2); 7.293 (0.4); 7.226 (2.3); 7.205 (3.7); 7.185 (2.2); 4.064 (2.0); 4.046 (3.6); 4.028 (2.2); 3.822 (1.6); 3.668 (0.5); 3.466 (16.0); 3.448 (0.8); 3.351 (0.7); 3.328 (185.6); 3.073 (2.0); 3.055 (3.5); 3.037 (1.9); 2.942 (0.5); 2.907 (0.4); 2.676 (0.4); 2.671 (0.5); 2.667 (0.4); 2.541 (0.8); 2.525 (1.7); 2.511 (28.6); 2.507 (58.7); 2.502 (79.3); 2.498 (61.3); 2.493 (33.8); 2.333

(0.3); 2.329 (0.5); 2.324 (0.4); 0.000 (7.3); -0.006 (0.7)

Example 22: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.582 (0.9); 7.565 (2.1); 7.561 (1.9); 7.544 (3.6); 7.527 (2.0); 7.523 (2.0); 7.506 (0.9); 7.371 (4.4); 7.365 (2.3); 7.349 (16.0); 7.333 (14.8); 7.312 (4.5); 7.281 (0.7); 7.260 (1.3); 7.239 (0.5); 7.221 (5.2); 7.201 (8.1); 7.181 (4.7); 7.144 (0.4); 7.067 (0.7); 7.048 (0.6); 4.037 (4.8); 4.019 (8.6); 4.001 (5.0); 3.794 (2.1); 3.665 (0.8); 3.654 (0.7); 3.637 (0.4); 3.627 (0.3); 3.448 (37.0); 3.438 (3.6); 3.368 (0.4); 3.328 (197.4); 2.950 (4.7); 2.932 (8.1); 2.915 (4.4); 2.893 (0.4); 2.872 (0.4); 2.836 (0.4); 2.819 (0.7); 2.801 (0.6); 2.780 (0.4); 2.676 (0.6); 2.671 (0.8); 2.667 (0.6); 2.541 (1.3); 2.524 (3.4); 2.511 (52.5); 2.507 (99.1); 2.502 (125.9); 2.498 (90.8); 2.493 (44.1); 2.333 (0.6); 2.329 (0.8); 2.324 (0.6); 1.235 (0.5); 0.008 (0.6); 0.000 (14.0); -0.009 (0.5)

Example 23: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.679 (6.8); 7.544 (2.7); 7.540 (3.0); 7.530 (3.3); 7.526 (6.3); 7.523 (5.4); 7.521 (5.4); 7.519 (4.5); 7.507 (6.0); 7.505 (6.9); 7.500 (4.4); 7.491 (3.5); 7.486 (3.9); 7.407 (2.5); 7.312 (8.8); 7.287 (15.2); 7.267 (16.0); 7.248 (3.5); 3.937 (2.5); 3.755 (1.0); 3.741 (0.9); 3.732 (0.9); 3.709 (0.9); 3.678 (0.9); 3.456 (4.0); 3.376 (1.0); 3.328 (286.5); 3.295 (0.8); 3.225 (5.5); 2.681 (0.4); 2.677 (0.9); 2.672 (1.3); 2.667 (0.9); 2.663 (0.5); 2.542 (5.0); 2.525 (4.1); 2.520 (6.3); 2.512 (73.7); 2.507 (147.7); 2.503 (193.7); 2.498 (138.1); 2.494 (64.6); 2.339 (0.4); 2.334 (0.9); 2.330 (1.2); 2.325 (0.9); 2.321 (0.4); 1.258 (0.4); 1.234 (0.9); 0.008 (0.9); 0.000 (28.4); -0.009 (0.8) Example 24: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.585 (3.6); 7.526 (3.9); 7.521 (2.3); 7.512 (5.0); 7.505 (7.3); 7.504 (7.2); 7.490 (7.7); 7.482 (6.4); 7.474 (2.5); 7.468 (5.1); 7.394 (13.8); 7.358 (1.8); 7.342 (1.7); 7.337 (1.7); 7.290 (11.9); 7.265 (16.0); 7.244 (14.9); 3.988 (2.9); 3.807 (0.7); 3.784 (0.7); 3.732 (0.8); 3.692 (1.0); 3.677 (0.8); 3.448 (5.6); 3.366 (1.2); 3.327 (314.5); 3.286 (0.4); 3.280 (0.4); 3.032 (8.0); 2.908 (0.9); 2.681 (0.5); 2.676 (1.0); 2.671 (1.4); 2.667 (1.0); 2.662 (0.5); 2.542 (4.5); 2.525 (4.7); 2.520 (7.5); 2.512 (82.5); 2.507 (162.7); 2.502 (210.9); 2.498 (149.3); 2.493 (69.7); 2.338 (0.5); 2.334 (1.0); 2.329 (1.4); 2.325 (1.0); 2.320 (0.4); 1.258 (0.4); 1.234 (0.9); 0.008 (1.3); 0.000 (37.7); -0.009 (1.1) Example 25: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.512 (2.9); 8.508 (2.9); 8.500 (2.7); 7.990 (1.9); 7.975 (2.1); 7.972 (2.1); 7.718 (9.4); 7.609 (0.9); 7.558 (1.7); 7.545 (2.0); 7.539 (2.0); 7.527 (1.8); 7.503 (0.4); 3.959 (2.2); 3.940 (3.3); 3.921 (2.4); 3.857 (1.6); 3.467 (16.0); 3.371 (0.3); 3.335 (124.7); 3.306 (2.6); 3.286 (3.4); 3.268 (2.2); 3.150 (0.6); 2.674 (0.3); 2.544 (3.0); 2.527 (1.1); 2.522 (1.7); 2.513 (19.8); 2.509 (39.4); 2.504 (51.3); 2.500 (36.9); 2.495 (17.6); 0.000 (3.2)

Example 26: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.496 (13.5); 8.491 (15.5); 8.483 (12.3); 8.479 (13.8); 7.911 (7.6); 7.895 (8.3); 7.621 (12.6); 7.565 (0.6); 7.560 (0.7); 7.538 (6.8); 7.526 (8.1); 7.520 (8.3); 7.507 (8.8); 7.499 (10.2); 7.478 (13.8); 7.429 (11.3); 7.425 (11.2); 7.408 (7.0); 7.405 (7.0); 7.363 (1.3); 7.342 (0.5); 7.337 (0.5); 7.305 (1.1); 4.039 (9.0); 4.021 (15.9); 4.003 (9.7); 3.840 (4.2); 3.692 (0.6); 3.620 (0.8); 3.595 (0.6); 3.554 (0.6); 3.533 (0.7); 3.441 (60.6); 3.334 (751.7); 3.286 (0.5); 3.277 (0.5); 3.258 (0.6); 3.114 (9.4); 3.096 (16.0); 3.078 (9.2); 2.964 (1.9); 2.908 (1.0); 2.681 (0.6); 2.677 (1.3); 2.672 (1.7); 2.668 (1.3); 2.663 (0.6); 2.543 (8.8); 2.526 (5.5); 2.521 (8.5); 2.512 (99.6); 2.508 (199.5); 2.503 (261.8); 2.499 (188.7); 2.494 (90.6); 2.339 (0.6); 2.335 (1.2); 2.330 (1.7); 2.326 (1.2); 2.321 (0.6); 1.299 (0.4); 1.258 (0.5); 1.249 (0.4); 1.244 (0.3); 1.234 (1.2); 0.008 (0.5); 0.000 (14.1); -0.009 (0.5)

Example 27: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.484 (7.2); 8.479 (7.6); 8.472 (7.7); 8.467 (7.6); 7.868 (3.5); 7.851 (3.9); 7.527 (3.0); 7.515 (3.5); 7.509 (3.4); 7.497 (2.8); 7.393 (4.1); 7.372 (16.0); 7.360 (15.4); 7.339 (4.4); 7.313 (1.1); 7.260 (0.4); 7.184 (0.4); 7.083 (0.6); 4.022 (4.3); 4.004 (7.6); 3.986 (4.6); 3.822 (1.2); 3.665 (0.4); 3.607 (0.3); 3.428 (28.0); 3.384 (0.5); 3.334 (379.5); 2.989 (4.5); 2.971 (7.7); 2.953 (4.4); 2.893 (0.4); 2.872 (0.4); 2.833 (0.6); 2.681 (0.3); 2.676 (0.7); 2.672 (0.9); 2.667 (0.7); 2.663 (0.3); 2.542 (4.6); 2.525 (2.8); 2.520 (4.1); 2.512 (53.6); 2.507 (108.7); 2.503 (143.1); 2.498 (102.2); 2.494 (48.0); 2.334 (0.7); 2.329 (0.9); 2.325 (0.6); 1.235 (0.5); 0.000 (4.7)

Example 28: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.715 (16.0); 7.662 (0.8); 7.596 (3.5); 7.535 (6.3); 7.516 (11.2); 7.488 (4.6); 7.466 (8.5); 7.445 (10.0); 7.434 (12.8); 7.373 (1.8); 7.255 (1.5); 3.944 (5.2); 3.928 (8.1); 3.910 (5.9); 3.842 (6.1); 3.610 (0.5); 3.570 (0.7); 3.473

(2.1) ; 3.432 (27.7); 3.332 (539.8); 3.297 (6.2); 3.279 (8.6); 3.262 (5.9); 3.201 (0.7); 3.128 (2.6); 2.681 (0.6); 2.677

(1.2) ; 2.672 (1.6); 2.668 (1.2); 2.663 (0.6); 2.543 (6.1); 2.526 (5.4); 2.512 (93.0); 2.508 (182.3); 2.503 (236.6); 2.499 (170.9); 2.494 (83.0); 2.339 (0.5); 2.335 (1.1); 2.330 (1.5); 2.325 (1.1); 2.321 (0.5); 1.299 (0.3); 1.258 (0.5); 1.249 (0.5); 1.234 (1.2); 0.008 (0.7); 0.000 (17.9); -0.008 (0.7)

Example 29: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.619 (4.8); 7.565 (0.5); 7.560 (0.5); 7.514 (6.7); 7.511 (6.7); 7.492 (16.0); 7.469 (10.0); 7.464 (8.5); 7.450 (9.8); 7.446 (10.8); 7.431 (7.7); 7.426 (10.8); 7.401 (7.1); 7.358 (5.2); 7.342 (3.3); 7.299 (1.2); 7.280 (1.2); 6.872 (0.7); 4.007 (6.2); 3.992 (4.1); 3.830 (2.7); 3.691 (0.6); 3.643 (0.4); 3.631 (0.4); 3.616 (0.4); 3.589 (0.5); 3.535 (0.5); 3.507 (0.5); 3.487 (0.6); 3.448 (2.4); 3.409 (18.1); 3.331 (424.1); 3.291 (0.5); 3.087 (6.3); 3.071 (4.1); 3.011 (0.5); 2.941 (1.4); 2.908 (1.5); 2.676 (1.0); 2.672 (1.3); 2.667 (1.0); 2.662 (0.5); 2.542 (4.9); 2.525 (3.8); 2.520 (6.1); 2.512 (77.0); 2.507 (154.8); 2.503 (203.3); 2.498 (146.0); 2.493 (69.4); 2.338 (0.5); 2.334 (1.0); 2.329 (1.3); 2.325 (0.9); 2.320 (0.4); 1.258 (0.4); 1.234 (0.8); 0.008 (0.7); 0.000 (22.6); -0.009 (0.7)

Example 30: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.748 (12.9); 8.738 (13.1); 8.315 (1.0); 7.954 (0.4); 7.713 (4.1); 7.628 (4.3); 7.512 (1.1); 7.451 (1.0); 7.381 (16.0); 7.344 (10.5); 7.231 (0.9); 7.206 (0.8); 7.190 (0.8); 7.171 (0.8); 7.142 (0.8); 7.080 (2.0); 6.971 (0.3); 6.887 (0.4); 6.826 (2.2); 6.691 (4.2); 6.556 (2.2); 4.685 (2.9); 4.023 (0.4); 3.918 (3.0); 3.823 (0.5); 3.770 (0.6); 3.745 (0.4); 3.733 (0.5); 3.720 (0.4); 3.690 (0.3); 3.610 (1.0); 3.589 (1.0); 3.523 (0.5); 3.492 (0.8); 3.454 (0.6); 3.433 (0.5); 3.427 (0.5); 3.421 (0.6); 3.397 (0.7); 3.387 (0.9); 3.379 (1.0); 3.369 (1.3); 3.327 (877.5); 3.276 (17.0); 3.175 (0.6); 3.165 (0.6); 3.089 (3.3); 3.070 (2.9); 2.949 (3.8); 2.891 (3.1); 2.827 (0.4); 2.818 (0.4); 2.786 (0.4); 2.763 (0.4); 2.731 (2.2); 2.676 (2.5); 2.671 (3.2); 2.667 (2.5); 2.541 (1.3); 2.525 (6.4); 2.511 (154.2); 2.507 (311.1); 2.502 (408.0); 2.498 (290.7); 2.493 (137.5); 2.334 (1.9); 2.329 (2.6); 2.324 (1.9); 1.339 (16.0); 1.235 (2.4); 1.192

(0.4); 1.173 (0.4); 1.145 (0.4); 0.855 (0.4); 0.000 (2.5)

Example 31 : ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.748 (12.4); 8.736 (12.5); 8.315 (1.3); 7.680 (4.5); 7.625 (4.3); 7.460 (1.2); 7.451 (1.2); 7.441 (1.2); 7.387 (7.8); 7.366 (8.4); 7.349 (11.5); 7.332 (14.1); 7.291 (5.4); 7.213 (1.0); 7.192 (1.0); 7.129 (1.6); 7.047 (1.3); 7.035

(1.3) ; 6.971 (0.4); 6.828 (2.6); 6.693 (5.1); 6.558 (2.7); 4.715 (2.9); 4.021 (0.4); 3.924 (3.7); 3.789 (0.5); 3.770 (0.4); 3.755 (0.4); 3.738 (0.4); 3.704 (0.4); 3.694 (0.4); 3.611 (1.1); 3.580 (3.1); 3.577 (2.2); 3.550 (0.5); 3.524 (0.5); 3.506 (0.4); 3.488 (0.4); 3.470 (0.5); 3.455 (0.5); 3.424 (0.5); 3.414 (0.6); 3.397 (0.7); 3.387 (0.7); 3.372 (0.8); 3.361 (1.3); 3.350 (1.9); 3.325 (647.7); 3.284 (17.5); 3.237 (1.5); 3.190 (0.5); 3.182 (0.5); 3.100 (3.5); 2.975 -7 -

(3.9); 2.891 (2.7); 2.790 (0.3); 2.772 (0.4); 2.731 (2.2); 2.680 (1.8); 2.676 (2.7); 2.671 (3.5); 2.667 (2.7); 2.596 (0.3); 2.541 (1.5); 2.525 (6.3); 2.520 (10.2); 2.511 (155.2); 2.507 (318.8); 2.502 (421.6); 2.498 (299.9); 2.493 (141.5); 2.333 (1.9); 2.329 (2.7); 2.324 (1.9); 1.465 (0.8); 1.456 (1.1); 1.448 (0.9); 1.439 (1.0); 1.351 (16.0); 1.236

(1.9); 1.164 (0.3); 1.145 (0.4); 1.004 (0.6); 0.988 (0.7); 0.929 (0.6); 0.912 (0.7); 0.853 (0.4); 0.000 (3.2)

Example 32: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.728 (6.2); 8.316 (0.7); 7.656 (3.4); 7.611 (3.3); 7.534 (0.5); 7.512 (0.6); 7.482 (0.5); 7.465 (0.6); 7.312 (16.0); 7.276 (8.1); 7.053 (2.1); 6.817 (0.4); 6.789 (1.6); 6.714 (0.4); 6.655 (3.1); 6.598 (0.4); 6.592 (0.4); 6.520 (1.7); 4.715 (2.1); 3.988 (0.6); 3.929 (3.4); 3.822 (0.4); 3.627 (0.4); 3.621 (0.4); 3.577 (0.9); 3.551 (0.9); 3.487 (0.4); 3.469 (0.4); 3.455 (0.4); 3.439 (0.4); 3.414 (0.4); 3.385 (0.6); 3.377 (0.7); 3.362 (0.9); 3.324 (369.4); 3.278

(12.4) ; 3.237 (1.4); 3.201 (0.4); 3.091 (2.4); 2.948 (3.1); 2.890 (2.3); 2.731 (1.6); 2.676 (2.3); 2.671 (2.9); 2.666

(2.3) ; 2.662 (1.5); 2.567 (0.4); 2.541 (1.2); 2.524 (5.3); 2.511 (121.5); 2.506 (246.2); 2.502 (321.8); 2.497 (227.2); 2.493 (105.6); 2.333 (1.5); 2.329 (2.0); 2.324 (1.4); 1.342 (11.7); 1.235 (1.6); 0.000 (3.2)

Example 33: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.316 (0.7); 7.789 (4.5); 7.769 (6.3); 7.715 (2.0); 7.696 (4.3); 7.678 (3.5); 7.656 (3.8); 7.637 (4.5); 7.618 (2.3); 7.593 (1.3); 7.397 (1.2); 7.366 (3.2); 7.348 (8.6); 7.329 (10.3); 7.309 (16.0); 7.291 (7.5); 7.268 (4.4); 7.250 (5.2); 7.231 (4.1); 7.211 (2.9); 7.055 (2.4); 5.920 (1.0); 4.589 (1.4); 4.546 (0.6); 3.912 (12.7); 3.488 (0.5); 3.446 (1.1); 3.405 (0.4); 3.362 (0.6); 3.348 (0.5); 3.324 (310.0); 3.303 (1.3); 3.288 (0.5); 3.274 (0.6); 3.253 (0.8); 3.213 (14.3); 3.144 (2.0); 3.124 (2.2); 3.110 (2.7); 3.091 (2.5); 2.994 (0.8); 2.943 (3.4); 2.924 (3.1); 2.909 (2.4); 2.891 (3.3); 2.732 (1.2); 2.676 (2.2); 2.671 (2.6); 2.667 (2.0); 2.654 (0.8); 2.541 (0.9); 2.524 (4.4); 2.511 (114.7); 2.507 (229.8); 2.502 (298.6); 2.497 (210.7); 2.493 (98.4); 2.443 (0.5); 2.427 (0.4); 2.338 (0.8); 2.333 (1.5); 2.329 (1.9); 2.324 (1.3); 2.319 (0.7); 1.304 (13.5); 1.288 (13.8); 1.235 (2.0); 1.194 (4.7); 1.176 (2.5); 1.158 (1.2); 1.145 (0.8);

1.128 (0.6); 1.109 (0.4); 0.000 (3.1)

Example 34: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.574 (0.7); 7.557 (1.7); 7.553 (1.5); 7.541 (1.6); 7.536 (2.9); 7.519 (1.8); 7.515 (1.6); 7.498 (0.7); 7.376 (4.6); 7.371 (1.9); 7.360 (2.8); 7.355 (11.1); 7.324 (9.9); 7.302 (4.3); 7.271 (2.0); 7.250 (2.5); 7.220 (1.9); 7.199 (5.1); 7.178 (4.5); 7.157 (1.4); 7.087 (0.4); 7.066 (0.6); 7.037 (2.3); 7.016 (1.9); 4.657 (1.0); 4.639 (1.8); 4.620 (1.8); 4.602 (1.0); 3.899 (8.8); 3.822 (0.4); 3.801 (0.4); 3.338 (29.9); 3.325 (139.8); 3.118 (1.5); 3.098 (1.5); 3.084 (2.2); 3.063 (2.2); 2.944 (2.2); 2.927 (2.2); 2.910 (1.6); 2.892 (2.0); 2.866 (0.4); 2.855 (0.7); 2.832 (0.6); 2.745 (0.7); 2.732 (1.0); 2.712 (0.4); 2.698 (0.4); 2.676 (0.4); 2.671 (0.6); 2.667 (0.4); 2.541 (0.4); 2.524 (1.4); 2.511 (34.9); 2.507 (69.9); 2.502 (90.9); 2.498 (64.4); 2.493 (30.2); 2.333 (0.4); 2.329 (0.5); 2.324 (0.4); 1.323 (12.9); 1.306

(16.0); 1.290 (3.5); 1.235 (0.4); 0.000 (0.8)

Example 35: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.6); 7.953 (0.4); 7.854 (4.1); 7.835 (4.8); 7.409 (4.2); 7.392 (3.0); 7.309 (15.4); 7.294 (15.8); 7.243 (5.9); 7.165 (3.4); 7.147 (4.9); 7.128 (3.9); 7.088 (5.2); 7.027 (10.5); 5.675 (2.2); 4.637 (2.1); 4.620 (2.1); 3.986 (16.0); 3.472 (2.5); 3.415 (0.4); 3.405 (0.3); 3.389 (0.3); 3.369 (0.4); 3.354 (0.5); 3.324 (239.8); 3.286 (15.5); 3.236 (1.0); 3.199 (2.2); 3.180 (2.5); 3.166 (2.9); 3.148 (2.7); 2.940 (3.3); 2.912 (4.1); 2.890 (4.3); 2.732 (1.1); 2.675 (1.4); 2.671 (1.9); 2.666 (1.6); 2.662 (1.2); 2.635 (1.7); 2.612 (1.5); 2.541 (0.4); 2.524 (2.8); 2.520 (4.6); 2.511 (85.1); 2.506 (176.3); 2.502 (233.6); 2.497 (167.2); 2.493 (79.6); 2.455 (0.8); 2.333 (1.2); 2.329 (1.6); 2.324

(1.2) ; 2.320 (0.6); 1.463 (0.4); 1.385 (8.0); 1.349 (12.7); 1.335 (11.7); 1.289 (1.3); 1.259 (1.0); 1.235 (2.1); 1.195 (0.7); 1.177 (1.0); 1.159 (0.7); 1.145 (0.6); 1.126 (0.6); 1.121 (0.6); 1.112 (0.6); 1.101 (0.7); 1.063 (0.7); 1.027

(0.5); 1.012 (0.6); 1.005 (0.5); 0.994 (0.8); 0.976 (0.4); 0.000 (2.5)

Example 36: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.5); 7.954 (0.5); 7.915 (0.4); 7.857 (6.7); 7.839 (7.5); 7.526 (0.3); 7.512 (0.4); 7.491 (0.5); 7.389

(12.5) ; 7.350 (15.4); 7.266 (0.9); 7.250 (0.9); 7.241 (1.0); 7.231 (1.0); 7.215 (1.4); 7.153 (7.6); 7.137 (5.5); 7.059

(9.4) ; 5.854 (1.6); 4.618 (2.4); 4.607 (2.4); 3.976 (11.5); 3.857 (0.4); 3.848 (0.4); 3.771 (0.4); 3.590 (0.3); 3.489 (2.0); 3.452 (1.5); 3.415 (1.5); 3.406 (0.4); 3.386 (0.4); 3.381 (0.3); 3.359 (0.6); 3.324 (211.4); 3.283 (18.0); 3.238 (1.0); 3.224 (0.7); 3.184 (2.1); 3.162 (2.7); 3.151 (3.1); 3.131 (2.8); 3.005 (0.3); 2.949 (2.9); 2.931 (3.6); 2.916 (3.6); 2.891 (4.4); 2.838 (0.6); 2.831 (0.5); 2.805 (0.4); 2.732 (1.6); 2.715 (0.4); 2.675 (2.1); 2.671 (2.6); 2.667

(2.3) ; 2.542 (0.5); 2.525 (2.8); 2.507 (164.3); 2.502 (211.0); 2.498 (151.4); 2.494 (72.8); 2.453 (0.6); 2.441 (0.5); 2.334 (1.1); 2.329 (1.4); 2.324 (1.0); 1.464 (0.3); 1.356 (16.0); 1.341 (14.4); 1.275 (0.9); 1.258 (1.0); 1.235 (2.2);

1.194 (0.7); 1.177 (0.8); 1.159 (0.7); 1.146 (0.7); 1.135 (0.7); 1.119 (0.7); 1.080 (0.6); 1.062 (0.7); 1.044 (0.5); 1.025 (0.3); 0.995 (0.3); 0.891 (0.4); 0.874 (0.8); 0.858 (0.6); 0.000 (1.8)

Example 37: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.578 (1.2); 7.561 (2.0); 7.557 (2.5); 7.540 (3.6); 7.523 (1.8); 7.519 (2.0); 7.502 (0.8); 7.339 (1.9); 7.320 (6.6); 7.303 (9.4); 7.293 (10.9); 7.276 (3.4); 7.250 (1.8); 7.246 (2.3); 7.241 (1.4); 7.229 (4.5); 7.212 (3.9); 7.203 (6.4);

7.195 (4.5); 7.183 (5.5); 7.162 (1.8); 7.123 (0.4); 7.100 (0.8); 7.079 (0.4); 6.988 (1.6); 6.984 (1.6); 6.969 (1.5); 4.642 (1.3); 4.624 (2.6); 4.606 (2.7); 4.588 (1.3); 3.905 (10.0); 3.816 (0.6); 3.799 (0.6); 3.782 (0.3); 3.355 (0.5); 3.340 (2.4); 3.324 (145.1); 3.301 (0.5); 3.283 (0.5); 3.134 (2.0); 3.115 (2.0); 3.100 (2.7); 3.081 (2.6); 2.933 (2.8); 2.914 (2.8); 2.899 (2.5); 2.891 (0.8); 2.880 (2.4); 2.866 (0.9); 2.847 (0.8); 2.776 (0.8); 2.760 (0.8); 2.742 (0.5); 2.732 (0.6); 2.726 (0.5); 2.675 (0.6); 2.671 (0.8); 2.666 (0.6); 2.541 (0.3); 2.506 (90.8); 2.502 (116.8); 2.497 -7 -

(84.3); 2.493 (40.7); 2.461 (0.4); 2.333 (0.5); 2.329 (0.7); 2.324 (0.5); 1.305 (16.0); 1.288 (15.7); 1.271 (4.2);

1.255 (4.0); 1.235 (0.5); 0.000 (1.0)

Example 38: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.316 (0.7); 8.182 (0.6); 7.792 (5.9); 7.773 (7.5); 7.730 (2.1); 7.712 (4.5); 7.694 (3.4); 7.663 (4.2); 7.643 (5.4); 7.625 (2.6); 7.468 (0.8); 7.454 (0.8); 7.447 (0.8); 7.414 (6.9); 7.394 (12.7); 7.343 (11.3); 7.323 (6.7); 7.302 (1.9); 7.281 (3.1); 7.261 (3.4); 7.243 (4.7); 7.221 (1.4); 7.182 (0.4); 7.123 (0.6); 7.079 (1.5); 6.987 (0.4); 6.142 (0.6); 4.582 (1.6); 4.571 (1.6); 3.961 (0.4); 3.919 (5.8); 3.905 (7.8); 3.640 (6.3); 3.496 (0.4); 3.488 (0.6); 3.475 (0.7); 3.470 (0.7); 3.455 (0.7); 3.415 (0.4); 3.399 (0.4); 3.386 (0.4); 3.363 (0.5); 3.324 (287.9); 3.276 (0.5); 3.217 (16.0); 3.134 (1.9); 3.114 (2.1); 3.100 (2.6); 3.080 (2.4); 3.037 (0.5); 3.016 (0.5); 3.003 (0.6); 2.983 (0.9); 2.949 (3.2); 2.931 (3.3); 2.915 (2.5); 2.896 (2.1); 2.891 (2.3); 2.872 (0.3); 2.858 (0.5); 2.841 (0.5); 2.824 (0.4); 2.807 (0.4); 2.731 (1.4); 2.710 (0.7); 2.680 (1.0); 2.676 (1.6); 2.671 (2.0); 2.667 (1.4); 2.542 (0.7); 2.525 (3.5); 2.511 (93.8); 2.507 (191.6); 2.502 (252.2); 2.498 (179.3); 2.493 (84.3); 2.338 (0.6); 2.334 (1.2); 2.329 (1.6); 2.324 (1.2); 1.351 (0.4); 1.307 (14.1); 1.291 (14.2); 1.259 (0.9); 1.235 (1.5); 1.191 (4.1); 1.178 (4.0); 1.129 (0.3); 0.000 (2.4) Example 39: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.713 (11.9); 7.606 (0.7); 7.601 (0.8); 7.590 (8.9); 7.569 (1.7); 7.553 (0.9); 7.548 (1.0); 7.532 (0.4); 7.251 (1.3); 7.239 (1.2); 7.230 (2.4); 7.219 (1.9); 7.209 (1.3); 7.197 (0.9); 7.161 (0.5); 7.139 (0.8); 7.118 (0.4); 4.871 (0.5); 4.855 (0.7); 4.848 (0.6); 4.838 (0.7); 4.832 (0.7); 4.816 (0.5); 4.108 (0.3); 4.090 (0.7); 4.073 (0.7); 4.056 (0.3); 3.943 (12.2); 3.500 (16.0); 3.402 (0.9); 3.379 (0.9); 3.368 (1.6); 3.345 (2.2); 3.328 (124.2); 3.282 (1.4); 3.268 (1.4); 3.249 (0.9); 3.234 (0.8); 3.205 (0.5); 3.185 (0.5); 3.171 (1.1); 3.151 (1.1); 3.122 (1.1); 3.106 (1.1); 3.088 (0.5); 3.072 (0.5); 2.892 (0.4); 2.672 (0.4); 2.525 (1.1); 2.512 (23.8); 2.508 (48.0); 2.503 (62.7); 2.498

(44.6); 2.494 (20.9); 2.330 (0.4); 1.299 (6.4); 1.282 (6.4); 1.262 (4.4); 1.246 (4.2)

Example 40: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.572 (1.0); 7.565 (0.7); 7.555 (1.8); 7.551 (2.1); 7.534 (3.2); 7.517 (1.8); 7.513 (1.9); 7.496 (0.8); 7.364 (6.0); 7.343 (4.4); 7.324 (5.1); 7.300 (4.2); 7.295 (3.1); 7.283 (1.7); 7.274 (3.7); 7.271 (4.3); 7.249 (4.6); 7.234 (1.8); 7.220 (2.1); 7.197 (5.2); 7.175 (4.8); 7.152 (1.6); 7.059 (0.5); 7.044 (2.2); 7.016 (0.5); 6.991 (1.0); 6.976 (0.8); 4.662 (1.1); 4.645 (2.0); 4.625 (2.0); 4.608 (1.2); 3.897 (11.7); 3.861 (0.5); 3.580 (0.5); 3.323 (125.8); 3.144 (1.8); 3.123 (1.8); 3.110 (2.6); 3.089 (2.5); 2.965 (2.4); 2.948 (2.5); 2.931 (1.8); 2.914 (1.7); 2.895 (0.7); 2.891 (0.7); 2.872 (0.6); 2.861 (0.9); 2.837 (0.8); 2.751 (0.8); 2.738 (0.9); 2.732 (0.6); 2.717 (0.6); 2.704 (0.5); 2.675 (0.5); 2.671 (0.7); 2.667 (0.5); 2.541 (0.3); 2.511 (42.8); 2.506 (84.4); 2.502 (109.3); 2.497 (78.4); 2.493 (37.4); 2.333

(0.5); 2.329 (0.7); 2.324 (0.5); 1.339 (15.0); 1.323 (16.0); 1.311 (4.7); 1.234 (0.5); 0.000 (0.9)

Example 41 : ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.317 (0.5); 7.821 (4.8); 7.801 (4.8); 7.789 (2.4); 7.769 (4.7); 7.750 (4.1); 7.729 (16.0); 7.699 (5.2); 7.681 (5.3); 7.662 (2.6); 7.648 (2.7); 7.616 (4.0); 7.551 (4.0); 7.532 (3.3); 7.106 (0.6); 4.724 (1.6); 4.710 (1.6); 3.932 (7.9); 3.820 (0.6); 3.813 (0.6); 3.416 (0.7); 3.406 (3.1); 3.393 (2.1); 3.360 (22.7); 3.326 (213.7); 3.301 (1.8); 3.286 (1.3); 3.256 (0.4); 3.238 (0.5); 3.223 (0.7); 3.188 (1.4); 3.131 (0.4); 2.892 (1.8); 2.733 (1.2); 2.682 (0.4); 2.677 (0.8); 2.673 (1.0); 2.668 (0.8); 2.543 (0.5); 2.526 (2.5); 2.521 (4.1); 2.513 (63.5); 2.508 (129.3); 2.504 (169.8); 2.499 (120.6); 2.495 (56.8); 2.335 (0.8); 2.331 (1.1); 2.326 (0.8); 2.322 (0.4); 1.303 (11.0); 1.286 (11.2); 1.234

(1.3); 1.201 (0.5); 1.142 (4.9); 0.910 (0.8); 0.894 (0.8); 0.000 (1.6)

Example 42: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.6); 7.859 (6.8); 7.840 (8.3); 7.511 (0.4); 7.496 (0.4); 7.432 (3.2); 7.416 (5.6); 7.380 (10.2); 7.355 (11.3); 7.321 (11.5); 7.300 (9.1); 7.212 (1.3); 7.169 (4.8); 7.151 (8.0); 7.133 (7.5); 7.081 (7.4); 7.020 (7.2); 5.713

(2.2) ; 4.646 (2.5); 4.632 (2.5); 3.978 (16.0); 3.900 (0.7); 3.581 (3.2); 3.577 (2.4); 3.524 (2.5); 3.509 (2.4); 3.455 (1.1); 3.434 (0.5); 3.415 (0.5); 3.406 (0.4); 3.390 (0.6); 3.375 (0.4); 3.368 (0.4); 3.325 (249.0); 3.291 (19.2); 3.237 (0.9); 3.223 (0.8); 3.191 (2.1); 3.158 (3.3); 3.138 (2.9); 3.100 (0.9); 3.076 (0.5); 2.978 (3.0); 2.959 (3.4); 2.944

(3.3) ; 2.927 (3.5); 2.891 (3.4); 2.767 (0.3); 2.732 (1.4); 2.676 (2.7); 2.671 (3.2); 2.667 (2.9); 2.542 (0.6); 2.525 (3.5); 2.511 (82.0); 2.507 (166.5); 2.502 (218.3); 2.498 (155.3); 2.493 (73.5); 2.334 (1.1); 2.329 (1.5); 2.325 (1.1); 1.481 (0.5); 1.465 (1.4); 1.456 (1.9); 1.448 (2.1); 1.439 (3.3); 1.406 (8.2); 1.371 (15.6); 1.356 (14.5); 1.306 (1.5); 1.290 (1.1); 1.270 (0.8); 1.259 (1.1); 1.234 (2.4); 1.195 (0.9); 1.177 (1.1); 1.160 (0.9); 1.145 (0.8); 1.105 (0.6); 1.083 (0.6); 1.065 (0.6); 1.047 (0.4); 1.013 (0.4); 1.004 (0.8); 0.995 (0.7); 0.988 (0.8); 0.977 (0.4); 0.929 (0.9); 0.912 (0.9); 0.900 (0.5); 0.883 (0.4); 0.853 (0.3); 0.000 (2.2)

Example 43: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.315 (0.3); 7.955 (1.5); 7.882 (5.0); 7.864 (4.7); 7.720 (5.8); 7.663 (0.7); 7.643 (4.7); 7.602 (9.0); 7.472 (3.3); 7.454 (2.6); 7.322 (2.7); 7.306 (2.5); 7.200 (3.4); 7.183 (5.4); 6.728 (1.2); 6.547 (0.8); 6.532 (0.8); 4.773 (1.4); 3.978 (16.0); 3.919 (0.8); 3.869 (1.2); 3.407 (20.9); 3.331 (226.7); 3.294 (0.8); 3.286 (0.8); 3.272 (0.7); 3.257 (0.5); 3.239 (0.4); 3.223 (0.4); 3.162 (1.7); 3.149 (2.1); 3.129 (2.9); 3.117 (2.9); 2.893 (8.7); 2.836 (0.7); 2.813 (0.6); 2.804 (0.6); 2.781 (0.5); 2.734 (7.6); 2.674 (0.6); 2.509 (80.4); 2.505 (103.8); 2.500 (75.9); 2.331 (0.7); 2.327 (0.5); 1.347 (11.1); 1.259 (0.8); 1.233 (1.5); 1.214 (0.5); 1.197 (0.6); 1.179 (0.7); 1.161 (0.7); 1.151 (0.7); 1.102 (1.3); 0.911 (3.4); 0.894 (3.3); 0.000 (0.9)

Example 44: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.5); 7.795 (6.2); 7.775 (7.9); 7.724 (1.9); 7.706 (4.4); 7.688 (3.4); 7.662 (4.4); 7.643 (5.5); 7.625 (2.6); - -

7.589 (0.4); 7.436 (1.0); 7.381 (11.9); 7.362 (6.4); 7.330 (6.1); 7.310 (3.5); 7.292 (5.4); 7.274 (3.7); 7.224 (3.2); 7.206 (3.0); 7.121 (1.3); 7.050 (1.1); 7.045 (1.1); 5.963 (0.8); 4.598 (1.5); 3.905 (9.8); 3.580 (1.3); 3.577 (0.9); 3.488 (0.8); 3.477 (0.8); 3.463 (0.6); 3.455 (0.5); 3.405 (0.4); 3.395 (0.3); 3.324 (306.1); 3.296 (0.5); 3.283 (0.6); 3.268 (0.5); 3.218 (16.0); 3.149 (1.9); 3.128 (2.1); 3.115 (2.8); 3.095 (2.5); 2.978 (3.2); 2.960 (3.5); 2.944 (2.8); 2.926 (2.5); 2.891 (1.4); 2.732 (1.3); 2.704 (0.8); 2.676 (1.7); 2.671 (2.1); 2.667 (1.6); 2.542 (0.7); 2.525 (4.1); 2.511 (93.9); 2.507 (189.3); 2.502 (247.0); 2.498 (176.4); 2.493 (83.9); 2.461 (0.5); 2.439 (0.3); 2.333 (1.1); 2.329 (1.6); 2.324 (1.1); 1.465 (0.5); 1.457 (0.5); 1.448 (0.4); 1.439 (0.4); 1.324 (13.3); 1.307 (13.6); 1.259 (0.8); 1.235

(2.2); 1.218 (5.2); 1.203 (5.0); 1.163 (0.4); 1.145 (0.4); 0.928 (0.3); 0.913 (0.4); 0.000 (2.1)

Example 45: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 9.066 (5.4); 9.060 (6.4); 8.999 (6.8); 8.993 (10.4); 7.404 (6.1); 7.399 (2.5); 7.388 (3.7); 7.383 (16.0); 7.356

(14.1) ; 7.339 (2.3); 7.335 (5.5); 7.283 (1.9); 7.262 (2.4); 7.100 (2.1); 7.079 (1.8); 4.570 (1.1); 4.552 (2.1); 4.534

(2.2) ; 4.516 (1.1); 3.922 (0.7); 3.907 (8.4); 3.888 (0.3); 3.328 (104.3); 3.176 (2.1); 3.156 (2.1); 3.141 (3.1); 3.121 (2.8); 3.011 (0.5); 2.991 (3.2); 2.973 (3.1); 2.957 (2.5); 2.938 (2.0); 2.892 (0.5); 2.824 (0.6); 2.805 (0.6); 2.790 (0.4); 2.771 (0.4); 2.733 (0.4); 2.673 (0.4); 2.526 (1.1); 2.512 (24.5); 2.508 (49.5); 2.503 (65.0); 2.499 (46.5);

2.494 (22.1); 2.330 (0.4); 1.328 (15.3); 1.311 (15.0); 1.195 (3.2); 1.179 (3.2); 0.000 (7.9)

Example 46: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 9.063 (5.5); 9.058 (6.5); 8.997 (7.6); 8.992 (7.7); 8.983 (2.2); 8.977 (1.1); 7.408 (6.5); 7.386 (2.0); 7.367 (5.3); 7.348 (6.3); 7.322 (5.1); 7.318 (3.8); 7.299 (6.1); 7.281 (3.0); 7.258 (2.0); 7.245 (2.2); 7.148 (1.4); 7.057 (0.5); 7.054 (0.5); 7.043 (0.8); 7.036 (0.5); 4.598 (1.1); 4.581 (2.2); 4.562 (2.2); 4.544 (1.2); 3.987 (0.6); 3.970 (0.6); 3.953 (0.3); 3.908 (8.9); 3.582 (0.8); 3.578 (0.5); 3.332 (48.8); 3.328 (79.1); 3.193 (2.1); 3.172 (2.1); 3.159 (3.0); 3.147 (0.5); 3.138 (2.9); 3.026 (0.6); 3.013 (3.0); 2.995 (3.3); 2.978 (2.3); 2.960 (2.0); 2.830 (0.7); 2.812 (0.6); 2.796 (0.5); 2.778 (0.5); 2.673 (0.4); 2.526 (1.0); 2.513 (22.0); 2.508 (44.6); 2.504 (58.6); 2.499 (41.7); 2.495

(19.7) ; 2.330 (0.4); 1.342 (16.0); 1.325 (15.7); 1.210 (3.6); 1.194 (3.5); 0.000 (7.4)

Example 47: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 9.069 (5.6); 9.064 (6.5); 9.035 (1.1); 9.029 (1.4); 9.001 (7.5); 8.996 (6.3); 7.361 (2.1); 7.342 (7.4); 7.324

(15.8) ; 7.318 (13.6); 7.302 (3.4); 7.269 (1.8); 7.265 (2.4); 7.259 (1.5); 7.248 (3.6); 7.241 (1.4); 7.237 (1.4); 7.231

(1.6) ; 7.226 (1.1); 7.221 (1.5); 7.203 (1.6); 7.192 (0.9); 7.175 (0.7); 7.051 (1.5); 7.034 (1.3); 4.563 (1.2); 4.545

(2.3) ; 4.527 (2.4); 4.510 (1.2); 3.914 (7.8); 3.900 (0.6); 3.879 (0.5); 3.327 (99.7); 3.318 (38.2); 3.187 (2.2); 3.168

(2.2) ; 3.153 (3.0); 3.134 (3.1); 3.040 (0.4); 3.025 (0.4); 3.007 (0.6); 2.992 (0.6); 2.979 (3.1); 2.959 (3.0); 2.945

(2.3) ; 2.925 (2.2); 2.891 (0.5); 2.846 (0.6); 2.825 (0.6); 2.813 (0.5); 2.792 (0.4); 2.732 (0.4); 2.676 (0.4); 2.672 (0.5); 2.667 (0.4); 2.512 (29.6); 2.507 (59.5); 2.503 (78.8); 2.498 (58.4); 2.494 (29.3); 2.334 (0.4); 2.330 (0.5);

2.325 (0.4); 1.318 (16.0); 1.301 (15.7); 1.167 (3.2); 1.151 (3.1); 0.008 (0.3); 0.000 (8.9); -0.009 (0.3)

Example 48: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 9.107 (2.2); 9.102 (2.5); 9.032 (2.6); 9.025 (2.8); 9.019 (0.9); 8.978 (0.8); 8.972 (0.6); 7.738 (11.9); 7.647 (0.4); 7.618 (3.2); 4.709 (0.4); 4.694 (0.6); 4.691 (0.6); 4.685 (0.6); 4.677 (0.6); 4.671 (0.6); 4.668 (0.6); 4.654 (0.4); 3.979 (4.5); 3.495 (16.0); 3.478 (1.0); 3.454 (0.9); 3.444 (1.3); 3.420 (1.3); 3.407 (0.7); 3.329 (32.1); 3.308

(1.3) ; 3.288 (0.9); 3.281 (0.4); 3.275 (0.9); 3.269 (0.5); 3.247 (0.4); 3.145 (0.4); 3.131 (0.4); 2.894 (1.5); 2.734 (1.2); 2.527 (0.4); 2.514 (8.8); 2.510 (17.7); 2.505 (23.3); 2.500 (16.5); 2.496 (7.8); 1.324 (5.4); 1.307 (5.3); 1.214

(1.7) ; 1.198 (1.6); 0.000 (3.0)

Example 49: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.788 (15.9); 8.778 (16.0); 8.317 (0.4); 7.966 (4.1); 7.717 (10.6); 7.677 (7.6); 7.075 (3.6); 6.940 (7.1); 6.805

(3.4) ; 4.801 (2.8); 3.940 (5.1); 3.709 (0.3); 3.553 (0.4); 3.520 (0.4); 3.376 (16.1); 3.329 (246.4); 3.171 (0.8); 3.104 (1.1); 2.893 (3.0); 2.734 (2.6); 2.678 (0.9); 2.673 (1.2); 2.669 (0.9); 2.544 (0.6); 2.527 (3.0); 2.513 (69.6); 2.509 (139.4); 2.504 (182.8); 2.500 (132.8); 2.335 (0.9); 2.331 (1.2); 2.327 (0.9); 1.322 (12.5); 1.205 (4.4); 0.008 (0.8);

0.000 (22.5); -0.009 (0.8)

Example 50: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.4); 7.954 (0.7); 7.865 (6.5); 7.846 (7.0); 7.626 (4.5); 7.582 (0.5); 7.558 (1.6); 7.532 (3.4); 7.463

(11.2) ; 7.441 (7.8); 7.424 (5.8); 7.357 (2.1); 7.353 (3.2); 7.332 (0.9); 7.275 (4.0); 7.255 (3.3); 7.182 (4.7); 7.162 (8.0); 6.446 (0.5); 6.432 (0.5); 5.984 (1.7); 4.720 (1.9); 4.705 (1.9); 3.981 (16.0); 3.872 (0.4); 3.859 (0.4); 3.853 (0.4); 3.806 (0.4); 3.775 (0.3); 3.722 (0.6); 3.669 (1.5); 3.471 (0.6); 3.462 (0.6); 3.409 (6.5); 3.391 (0.3); 3.331 (345.4); 3.306 (15.8); 3.274 (2.8); 3.258 (2.7); 3.238 (2.2); 3.193 (0.6); 3.177 (0.6); 3.174 (0.6); 3.158 (0.6); 3.142 (0.5); 3.123 (0.6); 3.089 (2.2); 3.072 (2.4); 3.055 (2.2); 3.037 (2.0); 3.006 (1.7); 2.992 (1.8); 2.973 (2.1); 2.959

(1.8) ; 2.892 (4.9); 2.814 (1.5); 2.732 (3.9); 2.677 (0.8); 2.673 (1.1); 2.668 (0.8); 2.572 (0.4); 2.552 (0.5); 2.543 (0.4); 2.539 (0.5); 2.526 (2.3); 2.512 (60.6); 2.508 (123.6); 2.504 (163.4); 2.499 (117.6); 2.495 (56.2); 2.335 (0.8); 2.330 (1.1); 2.326 (0.8); 1.383 (13.8); 1.368 (11.6); 1.299 (0.8); 1.272 (0.5); 1.259 (0.8); 1.234 (2.1); 1.208 (0.5); 1.200 (0.5); 1.191 (0.5); 1.181 (0.5); 1.174 (0.5); 1.165 (0.6); 1.160 (0.6); 1.144 (0.7); 1.101 (0.8); 0.954 (0.3);

0.901 (2.4); 0.885 (2.4); 0.008 (0.4); 0.000 (12.5); -0.009 (0.4)

Example 51 : ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.4); 7.803 (4.9); 7.784 (5.5); 7.753 (1.9); 7.735 (4.4); 7.716 (3.3); 7.678 (4.4); 7.659 (5.6); 7.636 (7.8); 7.566 (1.2); 7.527 (1.0); 7.457 (16.0); 7.364 (3.5); 7.345 (3.2); 7.306 (1.7); 7.288 (1.3); 6.297 (0.7); 4.677 (1.4); - -

4.667 (1.4); 3.922 (10.3); 3.630 (0.6); 3.408 (0.6); 3.333 (515.3); 3.295 (1.0); 3.256 (16.8); 3.230 (2.6); 3.215 (2.7); 3.195 (2.4); 3.082 (2.7); 3.064 (3.0); 3.048 (2.4); 3.030 (2.4); 2.972 (0.4); 2.959 (0.4); 2.946 (0.4); 2.936 (0.4); 2.922 (0.4); 2.919 (0.4); 2.892 (1.1); 2.868 (0.8); 2.733 (0.6); 2.677 (0.8); 2.672 (1.2); 2.668 (0.9); 2.542 (0.6); 2.526 (2.7); 2.512 (67.4); 2.508 (138.1); 2.503 (183.3); 2.499 (134.4); 2.495 (67.2); 2.334 (0.9); 2.330 (1.2); 2.325 (0.9); 1.332 (11.5); 1.315 (11.6); 1.259 (0.5); 1.234 (1.2); 1.191 (4.8); 1.176 (4.8); 0.000 (6.0)

Example 52: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.316 (0.4); 7.821 (7.6); 7.801 (8.5); 7.768 (6.5); 7.749 (5.3); 7.696 (7.0); 7.678 (8.7); 7.659 (4.7); 7.552 (7.3); 7.532 (14.5); 7.511 (12.9); 7.398 (5.3); 7.358 (5.2); 7.338 (7.3); 7.318 (4.8); 6.903 (1.2); 4.725 (2.6); 3.932 (12.1); 3.843 (1.3); 3.811 (1.0); 3.525 (0.5); 3.436 (2.9); 3.403 (6.0); 3.379 (7.9); 3.332 (617.0); 3.232 (1.9); 3.195 (1.6); 2.892 (1.4); 2.732 (0.8); 2.672 (1.9); 2.507 (244.7); 2.503 (297.2); 2.499 (238.3); 2.330 (1.9); 1.298 (15.7); 1.281

(16.0) ; 1.234 (2.3); 1.152 (12.0); 1.137 (11.7); 0.000 (8.7)

Example 53: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.317 (0.3); 7.954 (1.5); 7.879 (3.6); 7.862 (3.8); 7.524 (3.2); 7.505 (4.1); 7.471 (3.6); 7.459 (2.9); 7.452 (2.9); 7.439 (2.2); 7.405 (5.5); 7.386 (7.0); 7.326 (5.3); 7.310 (4.8); 7.286 (2.2); 7.266 (1.4); 7.245 (1.4); 7.199 (2.8); 7.182 (3.6); 7.165 (2.9); 6.542 (1.3); 4.805 (1.1); 4.792 (1.1); 3.984 (16.0); 3.927 (1.1); 3.901 (1.1); 3.890 (1.2); 3.811 (1.0); 3.625 (0.6); 3.604 (0.3); 3.594 (0.4); 3.461 (1.5); 3.432 (4.5); 3.421 (6.8); 3.399 (8.9); 3.364 (1.2); 3.331 (301.6); 3.296 (0.7); 3.272 (0.4); 3.181 (1.6); 3.098 (1.1); 2.892 (9.8); 2.733 (8.0); 2.677 (0.7); 2.673 (0.9);

2.668 (0.6); 2.543 (0.4); 2.526 (2.2); 2.521 (3.6); 2.512 (53.0); 2.508 (107.8); 2.503 (141.7); 2.499 (100.8); 2.494

(47.1) ; 2.339 (0.3); 2.335 (0.7); 2.330 (0.9); 2.326 (0.7); 2.321 (0.3); 1.805 (0.4); 1.495 (0.7); 1.343 (8.5); 1.258 (0.7); 1.250 (0.6); 1.234 (1.7); 1.225 (1.0); 1.196 (0.5); 1.178 (0.6); 1.160 (0.6); 1.125 (0.6); 1.114 (0.8); 1.096

(1.1) ; 1.078 (1.2); 1.013 (0.3); 0.906 (0.6); 0.889 (0.6); 0.008 (0.4); 0.000 (12.4); -0.009 (0.4)

Example 54: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.611 (0.4); 7.600 (0.6); 7.595 (1.1); 7.590 (0.9); 7.579 (1.4); 7.573 (1.7); 7.563 (0.7); 7.557 (1.2); 7.552 (0.9); 7.541 (0.4); 7.535 (0.5); 7.521 (4.8); 7.501 (6.3); 7.393 (2.6); 7.373 (4.4); 7.357 (2.0); 7.337 (2.3); 7.316 (1.3); 7.292 (1.5); 7.273 (1.3); 7.270 (1.2); 7.252 (1.6); 7.245 (1.5); 7.233 (2.0); 7.224 (2.6); 7.212 (1.1); 7.202 (1.3); 7.169 (0.5); 7.147 (0.8); 7.125 (0.4); 4.875 (0.5); 4.861 (0.6); 4.851 (0.6); 4.844 (0.6); 4.837 (0.7); 4.820 (0.5); 4.139 (0.3); 4.123 (0.6); 4.104 (0.6); 4.087 (0.4); 3.955 (12.3); 3.499 (16.0); 3.464 (1.1); 3.440 (1.1); 3.431 (1.5); 3.407 (1.5); 3.362 (0.4); 3.333 (167.4); 3.297 (1.5); 3.285 (1.8); 3.265 (1.6); 3.252 (1.7); 3.232 (1.0); 3.124 (1.0); 3.109 (0.9); 3.090 (0.7); 3.075 (0.6); 2.673 (0.4); 2.526 (0.9); 2.512 (22.3); 2.508 (45.4); 2.503 (59.9); 2.499

(43.3); 2.495 (21.1); 2.330 (0.4); 1.283 (6.5); 1.265 (6.5); 1.236 (4.8); 1.219 (4.5); 0.000 (3.6)

Example 55: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.783 (14.9); 8.768 (16.0); 8.316 (0.6); 7.966 (3.5); 7.898 (0.4); 7.672 (4.0); 7.585 (2.0); 7.567 (2.0); 7.510 (7.7); 7.502 (7.8); 7.475 (4.2); 7.460 (4.2); 7.454 (3.5); 7.440 (4.4); 7.416 (3.5); 7.323 (7.2); 7.286 (2.3); 7.266

(1.2) ; 7.246 (0.6); 7.072 (3.0); 6.937 (5.8); 6.801 (2.8); 6.543 (0.5); 6.527 (0.5); 4.828 (2.5); 4.133 (0.4); 4.042 (0.5); 3.943 (5.9); 3.929 (5.8); 3.811 (2.1); 3.773 (1.0); 3.748 (0.4); 3.643 (0.3); 3.624 (1.8); 3.603 (1.4); 3.594 (1.5); 3.538 (0.4); 3.498 (0.6); 3.461 (1.1); 3.420 (7.3); 3.368 (20.7); 3.331 (876.8); 3.275 (2.1); 3.264 (2.0); 3.242 (1.9); 3.193 (1.8); 3.180 (1.7); 3.160 (2.0); 3.148 (1.8); 3.016 (0.7); 2.891 (1.8); 2.865 (0.4); 2.842 (0.4); 2.833 (0.4); 2.809 (0.4); 2.763 (0.6); 2.732 (1.6); 2.676 (1.7); 2.672 (2.3); 2.668 (1.8); 2.542 (0.9); 2.507 (274.7); 2.503 (362.8); 2.499 (281.8); 2.446 (0.5); 2.334 (1.8); 2.330 (2.4); 2.326 (1.9); 2.262 (0.5); 1.805 (1.3); 1.494 (1.4); 1.317 (11.9); 1.259 (3.5); 1.234 (6.1); 1.214 (5.3); 1.113 (0.4); 1.095 (0.4); 0.975 (0.7); 0.959 (0.7); 0.905 (2.0);

0.889 (2.0); 0.854 (0.4); 0.000 (23.8)

Example 56: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.753 (5.0); 8.744 (4.9); 7.867 (2.3); 7.854 (2.4); 7.639 (2.6); 7.471 (0.3); 7.455 (0.4); 7.320 (16.0); 7.270 (5.5); 7.265 (5.2); 7.249 (6.5); 7.210 (0.8); 7.191 (0.6); 7.178 (0.6); 7.159 (0.6); 7.141 (0.8); 7.123 (0.6); 7.104 (0.5); 7.090 (0.6); 7.071 (0.6); 7.048 (0.7); 7.030 (0.6); 6.797 (1.1); 6.662 (2.1); 6.528 (1.0); 4.023 (5.0); 3.823 (0.6); 3.797 (0.5); 3.728 (0.3); 3.722 (0.4); 3.710 (0.3); 3.561 (0.7); 3.531 (0.5); 3.515 (0.6); 3.499 (0.6); 3.483 (0.7); 3.446 (1.3); 3.434 (2.0); 3.428 (1.8); 3.388 (11.8); 3.329 (308.7); 3.281 (0.5); 3.266 (0.4); 3.244 (0.7); 2.968 (5.5); 2.891 (1.3); 2.863 (0.5); 2.844 (0.5); 2.732 (0.7); 2.671 (1.0); 2.506 (124.5); 2.502 (150.8); 2.498 (107.8);

2.329 (1.0); 1.236 (0.9); 0.000 (12.2)

Example 57: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.4); 7.805 (3.8); 7.785 (5.0); 7.750 (1.3); 7.732 (3.1); 7.713 (2.3); 7.676 (2.5); 7.657 (3.3); 7.638 (1.7); 7.519 (0.6); 7.440 (3.3); 7.421 (3.0); 7.358 (1.6); 7.339 (6.3); 7.323 (16.0); 7.288 (1.7); 7.267 (4.4); 7.262 (4.9); 7.254 (3.4); 7.245 (4.8); 7.237 (1.9); 7.229 (1.8); 7.224 (1.1); 7.140 (0.3); 7.044 (1.1); 7.028 (1.1); 6.595 (0.5); 6.582 (0.5); 3.966 (3.4); 3.947 (5.0); 3.928 (3.7); 3.797 (2.4); 3.561 (0.3); 3.446 (0.4); 3.434 (0.5); 3.428 (1.0); 3.401 (0.5); 3.364 (23.5); 3.332 (418.3); 3.300 (0.7); 3.295 (0.6); 3.275 (0.3); 3.266 (0.3); 3.244 (0.5); 3.181 (0.4); 2.954 (3.6); 2.935 (5.3); 2.916 (3.6); 2.891 (1.2); 2.853 (0.4); 2.849 (0.4); 2.834 (0.4); 2.817 (0.4); 2.798 (0.4); 2.732 (0.7); 2.676 (0.7); 2.671 (1.0); 2.667 (0.7); 2.542 (0.6); 2.525 (2.7); 2.511 (56.0); 2.507 (112.2); 2.502 (147.2); 2.498 (105.4); 2.493 (50.2); 2.338 (0.4); 2.334 (0.7); 2.329 (1.0); 2.325 (0.7); 1.235 (0.7); 0.008 (0.4); 0.000 (10.9); -0.009 (0.3)

Example 58: ^J H-NMR (400.0 MHz, d ₆ -DMSO): - - δ= 8.316 (0.4); 7.863 (8.1); 7.843 (8.6); 7.437 (3.1); 7.420 (2.2); 7.327 (16.0); 7.288 (3.3); 7.248 (8.1); 7.239 (8.0); 7.216 (4.9); 7.197 (3.6); 7.179 (3.4); 7.162 (4.8); 7.144 (3.5); 7.088 (0.5); 7.068 (0.5); 7.045 (0.9); 7.010 (1.8); 6.481 (0.8); 3.953 (5.2); 3.935 (3.7); 3.850 (3.5); 3.721 (0.4); 3.705 (0.4); 3.675 (0.5); 3.605 (0.3); 3.575 (0.4); 3.561 (0.6); 3.528 (0.3); 3.516 (0.4); 3.507 (0.3); 3.466 (0.8); 3.446 (1.0); 3.433 (1.6); 3.428 (2.8); 3.398 (15.8); 3.331 (620.9); 3.281 (0.7); 3.266 (0.7); 3.257 (0.5); 3.244 (1.0); 3.224 (0.5); 3.211 (0.5); 3.181 (0.4); 3.171 (0.4); 3.019 (5.3); 3.004 (3.7); 2.890 (1.6); 2.849 (1.5); 2.840 (1.5); 2.732 (0.9); 2.680 (0.6); 2.676 (1.1); 2.671

(1.5) ; 2.667 (1.1); 2.662 (0.5); 2.541 (0.9); 2.524 (3.6); 2.520 (5.8); 2.511 (85.2); 2.507 (171.3); 2.502 (223.0); 2.497 (157.9); 2.493 (73.6); 2.457 (0.5); 2.338 (0.6); 2.333 (1.1); 2.329 (1.5); 2.324 (1.1); 2.320 (0.5); 1.341 (0.5);

1.235 (1.1); 0.008 (0.4); 0.000 (12.0); -0.009 (0.4)

Example 59: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.587 (0.6); 7.570 (1.2); 7.566 (1.2); 7.549 (2.1); 7.532 (1.1); 7.528 (1.3); 7.511 (0.6); 7.336 (1.0); 7.317 (4.9); 7.307 (5.9); 7.301 (16.0); 7.287 (1.6); 7.264 (0.4); 7.249 (1.3); 7.243 (1.7); 7.234 (2.3); 7.227 (5.0); 7.206 (6.0); 7.186 (3.4); 7.026 (0.5); 7.009 (0.4); 4.020 (3.1); 4.001 (4.5); 3.983 (3.3); 3.802 (1.4); 3.636 (0.4); 3.445 (23.1); 3.428 (0.5); 3.332 (207.8); 3.311 (0.7); 2.956 (3.1); 2.937 (4.3); 2.919 (2.8); 2.891 (0.4); 2.831 (0.4); 2.676 (0.3);

2.671 (0.5); 2.667 (0.4); 2.511 (26.1); 2.507 (52.5); 2.502 (69.5); 2.498 (50.8); 2.493 (24.8); 2.333 (0.3); 2.329

(0.5); 2.325 (0.4); 0.000 (4.2)

Example 60: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.621 (4.7); 7.616 (4.7); 7.598 (0.4); 7.582 (1.1); 7.577 (0.8); 7.566 (1.7); 7.561 (2.3); 7.545 (3.0); 7.541 (1.6); 7.528 (1.5); 7.524 (1.7); 7.507 (0.7); 7.457 (2.6); 7.452 (2.8); 7.430 (1.2); 7.409 (7.8); 7.405 (6.3); 7.400 (5.3); 7.384 (0.8); 7.379 (1.0); 7.361 (1.3); 7.356 (1.1); 7.340 (2.1); 7.335 (2.0); 7.286 (3.2); 7.265 (1.8); 7.229 (2.1); 7.208 (5.3); 7.186 (4.5); 7.165 (1.3); 7.114 (0.6); 7.092 (1.1); 7.071 (0.5); 4.776 (1.0); 4.759 (1.8); 4.739 (1.8); 4.722 (1.0); 4.009 (0.4); 3.993 (0.7); 3.975 (0.8); 3.958 (0.5); 3.930 (16.0); 3.386 (27.9); 3.370 (0.5); 3.361 (0.9); 3.332 (296.7); 3.228 (1.6); 3.208 (1.6); 3.194 (2.4); 3.173 (2.3); 3.072 (2.3); 3.055 (2.3); 3.038 (1.6); 3.020 (1.6); 3.010 (0.8); 2.989 (0.8); 2.976 (1.2); 2.955 (1.1); 2.878 (1.2); 2.863 (1.2); 2.844 (0.8); 2.829 (0.7); 2.676 (0.5);

2.672 (0.6); 2.667 (0.5); 2.542 (0.4); 2.525 (2.3); 2.512 (36.4); 2.507 (72.9); 2.503 (96.2); 2.498 (69.4); 2.494 (33.3); 2.334 (0.4); 2.330 (0.6); 2.325 (0.5); 1.354 (12.0); 1.337 (11.8); 1.299 (5.9); 1.282 (5.8); 1.234 (0.4); 0.000

(4-5)

Example 62: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.316 (0.3); 7.970 (0.4); 7.952 (0.5); 7.857 (2.8); 7.837 (3.4); 7.486 (0.3); 7.479 (0.4); 7.467 (0.6); 7.458 (0.7); 7.414 (2.7); 7.396 (1.9); 7.360 (0.5); 7.342 (0.4); 7.251 (2.6); 7.230 (2.4); 7.197 (3.4); 7.173 (3.3); 7.151 (3.4); 7.130 (2.9); 7.099 (3.8); 7.064 (2.9); 6.867 (6.0); 6.823 (4.2); 6.803 (3.1); 6.750 (0.4); 6.609 (3.1); 6.591 (3.2); 6.563 (4.7); 5.787 (1.7); 4.656 (1.3); 4.642 (1.4); 3.980 (12.5); 3.752 (12.2); 3.718 (2.7); 3.685 (16.0); 3.482 (1.9); 3.383 (0.4); 3.373 (0.8); 3.333 (122.2); 3.305 (10.9); 3.168 (1.3); 3.149 (1.6); 3.135 (1.9); 3.118 (1.8); 2.912 (1.9); 2.891 (2.9); 2.882 (2.7); 2.732 (0.5); 2.677 (0.5); 2.672 (0.6); 2.668 (0.5); 2.606 (1.4); 2.578 (1.1); 2.549 (4.9); 2.526 (0.9); 2.512 (29.0); 2.508 (60.6); 2.503 (81.2); 2.499 (60.3); 2.495 (30.6); 2.334 (0.4); 2.330 (0.6); 2.325 (0.4); 1.380 (6.0); 1.343 (8.1); 1.328 (7.6); 1.258 (0.7); 1.234 (1.7); 1.196 (0.4); 1.178 (0.5); 1.160 (0.5); 1.143 (0.5); 1.122 (0.5); 1.104 (0.5); 1.090 (0.6); 0.008 (0.4); 0.000 (14.2); -0.009 (0.6)

Example 63: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (1.0); 7.797 (5.9); 7.778 (6.3); 7.741 (2.6); 7.723 (5.9); 7.704 (4.7); 7.671 (5.7); 7.652 (6.0); 7.634 (2.4);

7.588 (0.9); 7.468 (1.6); 7.447 (3.6); 7.429 (3.7); 7.408 (1.7); 7.303 (4.0); 7.285 (3.8); 7.256 (2.7); 7.232 (4.9); 7.212 (3.4); 7.207 (3.3); 7.109 (2.6); 7.088 (4.7); 7.070 (3.1); 6.533 (0.7); 4.612 (1.9); 4.601 (1.9); 3.904 (10.7); 3.761 (0.4); 3.664 (0.4); 3.641 (0.4); 3.636 (0.4); 3.617 (0.4); 3.596 (0.4); 3.588 (0.4); 3.518 (0.9); 3.443 (0.5); 3.433 (0.5); 3.422 (0.6); 3.389 (1.1); 3.335 (1219.7); 3.304 (1.9); 3.265 (23.8); 3.139 (1.9); 3.119 (2.1); 3.105 (3.0); 3.086 (2.9); 2.979 (3.5); 2.961 (3.9); 2.945 (3.1); 2.926 (2.7); 2.891 (1.5); 2.797 (1.0); 2.732 (1.0); 2.677

(1.6) ; 2.672 (2.2); 2.668 (1.7); 2.525 (4.5); 2.512 (121.2); 2.507 (251.7); 2.503 (335.7); 2.498 (245.9); 2.494 (121.2); 2.334 (1.5); 2.330 (2.1); 2.325 (1.6); 1.319 (15.6); 1.302 (16.0); 1.259 (1.2); 1.235 (2.4); 1.170 (6.0); 1.155 (5.9); 0.854 (0.3); 0.008 (1.0); 0.000 (36.8); -0.008 (1.4)

Example 64: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.9); 7.797 (6.4); 7.778 (7.6); 7.730 (2.6); 7.712 (5.6); 7.694 (4.5); 7.667 (6.0); 7.648 (7.3); 7.629 (3.2);

7.589 (0.5); 7.506 (1.1); 7.407 (2.6); 7.388 (5.1); 7.369 (3.6); 7.349 (2.4); 7.331 (4.0); 7.314 (4.4); 7.299 (2.9); 7.277 (3.9); 7.259 (3.7); 7.217 (6.9); 7.196 (11.0); 7.176 (6.8); 7.040 (0.4); 6.294 (0.9); 4.630 (1.9); 3.910 (13.6); 3.663 (0.5); 3.643 (0.4); 3.612 (0.3); 3.527 (1.1); 3.470 (0.5); 3.448 (0.5); 3.434 (0.6); 3.389 (1.6); 3.339 (1203.7); 3.258 (21.6); 3.164 (2.1); 3.145 (2.3); 3.131 (3.1); 3.112 (2.9); 3.006 (3.4); 2.988 (4.0); 2.972 (3.4); 2.953 (3.3); 2.891 (1.2); 2.815 (1.3); 2.732 (0.8); 2.677 (1.5); 2.672 (2.1); 2.668 (1.6); 2.537 (5.6); 2.526 (4.4); 2.512 (117.3); 2.508 (242.2); 2.503 (322.7); 2.499 (239.6); 2.494 (120.6); 2.376 (0.7); 2.334 (1.5); 2.330 (2.1); 2.325 (1.6); 1.318 (15.6); 1.301 (16.0); 1.258 (0.9); 1.235 (2.3); 1.175 (5.2); 1.102 (0.4); 0.008 (0.7); 0.000 (21.1); -0.008 (0.9) Example 65: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.954 (1.0); 7.858 (1.8); 7.839 (2.2); 7.417 (1.7); 7.151 (2.2); 7.129 (2.2); 7.104 (2.3); 7.066 (1.9); 6.894 (3.7); 6.869 (2.3); 6.850 (2.1); 6.814 (1.7); 6.798 (1.3); 6.559 (4.3); 6.533 (2.1); 5.802 (1.2); 4.646 (0.9); 4.632 (0.9); 3.980 (8.2); 3.748 (14.2); 3.735 (16.0); 3.687 (1.4); 3.629 (11.7); 3.454 (1.5); 3.335 (82.0); 3.308 (7.2); 3.121 - -

(0.9); 3.087 (1.2); 3.072 (1.1); 2.891 (5.9); 2.871 (1.1); 2.848 (1.6); 2.821 (1.6); 2.732 (5.1); 2.672 (0.4); 2.542 (4.2); 2.507 (41.6); 2.503 (52.0); 2.499 (39.8); 2.330 (0.4); 1.372 (4.1); 1.333 (5.1); 1.320 (4.7); 1.258 (0.5); 1.234 (0.9); 1.178 (0.3); 1.081 (0.4); 0.000 (6.0)

Example 66: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.317 (0.7); 7.806 (5.5); 7.786 (6.2); 7.757 (2.8); 7.739 (6.4); 7.720 (5.6); 7.682 (6.0); 7.663 (6.1); 7.645 (2.8); 7.419 (1.2); 7.400 (3.5); 7.380 (8.1); 7.362 (7.3); 7.143 (5.6); 7.124 (9.2); 7.104 (5.3); 7.038 (2.5); 6.911 (0.8); 4.625 (2.2); 4.617 (2.2); 3.905 (9.3); 3.688 (0.5); 3.611 (1.0); 3.606 (1.0); 3.427 (0.3); 3.409 (0.4); 3.389 (0.8); 3.334 (825.6); 3.320 (32.8); 3.267 (0.8); 3.221 (0.4); 3.173 (2.0); 3.155 (2.3); 3.140 (3.4); 3.123 (3.2); 3.031 (4.0); 3.011 (4.2); 2.999 (3.4); 2.978 (2.8); 2.891 (1.7); 2.860 (1.0); 2.732 (0.9); 2.677 (1.4); 2.672 (2.0); 2.668 (1.5); 2.526 (3.9); 2.512 (110.9); 2.508 (229.0); 2.503 (305.6); 2.499 (224.3); 2.494 (111.7); 2.334 (1.4); 2.330 (2.0); 2.325 (1.5); 1.351 (0.6); 1.316 (15.3); 1.299 (16.0); 1.259 (1.3); 1.235 (2.6); 1.148 (7.1); 1.134 (6.8); 0.854 (0.4); 0.008 (1.4); 0.000 (48.0); -0.008 (2.0)

Example 67: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.793 (2.4); 7.774 (3.5); 7.720 (1.1); 7.702 (2.3); 7.685 (1.8); 7.660 (2.0); 7.641 (2.5); 7.622 (1.4); 7.404 (0.7); 7.277 (1.4); 7.257 (3.2); 7.238 (3.1); 6.875 (5.6); 6.831 (2.3); 6.811 (2.0); 6.625 (0.8); 6.597 (1.1); 6.023 (0.6); 6.014 (0.6); 4.611 (0.8); 3.907 (8.0); 3.754 (16.0); 3.695 (4.3); 3.455 (0.7); 3.447 (0.7); 3.432 (0.6); 3.408 (0.4); 3.389 (0.6); 3.380 (0.6); 3.339 (433.9); 3.304 (1.0); 3.275 (0.5); 3.230 (8.3); 3.113 (1.0); 3.094 (1.1); 3.080 (1.4); 3.060 (1.3); 2.958 (0.4); 2.916 (1.7); 2.897 (1.7); 2.882 (1.3); 2.863 (1.1); 2.732 (0.4); 2.676 (0.7); 2.672 (0.9); 2.667 (0.8); 2.663 (0.6); 2.642 (0.6); 2.619 (0.5); 2.542 (1.8); 2.525 (1.6); 2.512 (40.4); 2.508 (81.1); 2.503 (107.0); 2.499 (79.6); 2.334 (0.5); 2.330 (0.7); 2.325 (0.5); 1.297 (6.9); 1.281 (6.9); 1.234 (1.0); 1.200 (2.7); 1.188

(2.8); 0.000 (5.5)

Example 68: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.317 (0.4); 7.969 (0.4); 7.949 (0.5); 7.859 (6.7); 7.841 (7.3); 7.668 (0.3); 7.476 (0.6); 7.419 (6.0); 7.400 (6.0); 7.322 (5.4); 7.308 (5.2); 7.155 (16.0); 7.081 (4.7); 5.948 (1.8); 4.688 (2.1); 4.677 (2.2); 3.976 (16.0); 3.718 (0.3); 3.649 (0.4); 3.565 (1.8); 3.455 (0.4); 3.375 (1.5); 3.337 (211.1); 3.271 (1.0); 3.205 (1.9); 3.174 (2.9); 3.156 (2.8); 3.017 (2.5); 2.997 (3.0); 2.985 (2.7); 2.966 (2.3); 2.891 (2.3); 2.826 (0.6); 2.774 (1.7); 2.738 (1.2); 2.733 (1.4); 2.678 (0.5); 2.673 (0.7); 2.669 (0.6); 2.550 (5.6); 2.526 (1.3); 2.509 (78.2); 2.504 (104.3); 2.500 (78.4); 2.379 (0.4); 2.335 (0.5); 2.331 (0.7); 2.326 (0.6); 1.363 (14.1); 1.349 (12.8); 1.301 (1.4); 1.269 (0.7); 1.259 (0.9); 1.234 (2.2); 1.206 (0.6); 1.196 (0.6); 1.178 (0.7); 1.161 (0.7); 1.143 (0.7); 1.122 (0.7); 1.104 (0.7); 1.087 (0.7); 1.012

(0.3); 0.995 (0.3); 0.008 (0.5); 0.000 (16.0); -0.008 (0.8)

Example 69: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.317 (0.4); 7.979 (0.6); 7.959 (0.7); 7.866 (7.6); 7.847 (7.5); 7.698 (0.5); 7.681 (0.6); 7.449 (5.0); 7.432 (6.8); 7.415 (4.4); 7.247 (3.3); 7.222 (5.0); 7.201 (5.2); 7.178 (8.4); 7.159 (11.0); 7.142 (6.6); 7.084 (6.8); 6.161 (1.3); 4.660 (2.1); 4.647 (2.2); 3.967 (12.0); 3.758 (0.3); 3.730 (0.4); 3.702 (0.3); 3.661 (0.3); 3.556 (1.5); 3.491 (0.5); 3.456 (0.4); 3.374 (2.1); 3.337 (226.9); 3.224 (0.5); 3.177 (1.7); 3.144 (2.8); 3.126 (2.6); 3.050 (0.4); 2.989 (2.4); 2.972 (2.8); 2.958 (2.5); 2.939 (2.3); 2.892 (2.2); 2.750 (1.4); 2.739 (1.6); 2.734 (1.8); 2.678 (0.7); 2.674 (0.9); 2.669 (0.7); 2.551 (4.8); 2.527 (1.3); 2.513 (42.0); 2.509 (86.6); 2.504 (115.7); 2.500 (87.4); 2.379 (0.7); 2.336 (0.6); 2.331 (0.8); 2.327 (0.6); 1.365 (16.0); 1.351 (14.7); 1.259 (1.0); 1.234 (2.1); 1.212 (0.7); 1.197 (0.7); 1.190 (0.7); 1.179 (0.8); 1.173 (0.8); 1.155 (0.9); 1.137 (0.8); 1.122 (0.7); 1.104 (0.7); 1.087 (0.6); 0.008 (0.4); 0.000

(13.9); -0.008 (0.7)

Example 70: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.5); 7.785 (6.4); 7.765 (8.0); 7.693 (2.4); 7.661 (9.5); 7.633 (10.8); 7.616 (8.1); 7.604 (7.1); 7.585 (4.7); 7.567 (2.0); 7.534 (0.5); 7.489 (0.3); 7.428 (1.5); 7.325 (0.8); 7.139 (2.5); 7.123 (2.3); 5.780 (0.6); 4.656 (1.4); 3.919 (8.9); 3.509 (0.7); 3.426 (0.5); 3.419 (0.4); 3.388 (0.8); 3.371 (1.7); 3.338 (728.6); 3.279 (0.5); 3.247 (2.0); 3.224 (2.7); 3.195 (16.0); 3.085 (2.8); 3.069 (3.0); 3.051 (2.5); 3.034 (2.3); 2.892 (0.8); 2.819 (0.7); 2.795 (0.6); 2.732 (0.6); 2.681 (0.5); 2.677 (0.9); 2.673 (1.3); 2.668 (1.0); 2.663 (0.5); 2.540 (3.8); 2.526 (2.7); 2.521 (4.2); 2.512 (72.5); 2.508 (151.1); 2.503 (202.3); 2.499 (146.6); 2.495 (70.7); 2.377 (0.4); 2.339 (0.5); 2.335 (0.9); 2.330 (1.3); 2.326 (1.0); 1.353 (12.6); 1.336 (12.9); 1.300 (0.8); 1.248 (4.8); 1.234 (5.3); 0.008 (0.6); 0.000 (20.5);

-0.008 (0.7)

Example 71 : ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.953 (0.5); 7.850 (1.4); 7.831 (2.0); 7.426 (0.8); 7.409 (1.3); 7.391 (0.9); 7.260 (1.8); 7.240 (2.1); 7.222 (2.5); 7.208 (2.4); 7.162 (1.5); 7.141 (1.9); 7.124 (1.8); 7.047 (3.1); 7.031 (3.1); 6.996 (1.1); 6.976 (1.1); 6.943 (0.8); 6.926 (1.4); 6.898 (2.8); 6.883 (3.0); 5.830 (1.0); 4.699 (0.6); 4.683 (0.6); 3.964 (14.0); 3.813 (5.4); 3.737 (0.4); 3.649 (0.8); 3.630 (0.9); 3.474 (16.0); 3.372 (0.5); 3.335 (117.2); 3.282 (4.8); 3.126 (0.6); 3.095 (0.8); 3.075 (0.7); 2.958 (0.7); 2.941 (0.7); 2.928 (0.6); 2.909 (0.5); 2.891 (2.9); 2.732 (3.5); 2.715 (1.4); 2.681 (0.7); 2.677 (0.8); 2.672 (0.8); 2.668 (0.6); 2.540 (3.4); 2.525 (0.7); 2.512 (20.9); 2.507 (42.5); 2.503 (56.1); 2.498 (41.2); 2.494 (20.4); 2.330 (0.4); 1.325 (5.1); 1.308 (3.9); 1.258 (0.5); 1.234 (0.9); 1.012 (0.4); 0.994 (0.5); 0.989 (0.4); 0.978 (0.4); 0.000 (5.8)

Example 72: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.794 (1.9); 7.775 (2.8); 7.725 (0.9); 7.707 (1.8); 7.689 (1.4); 7.661 (1.5); 7.642 (1.9); 7.623 (1.1); 7.599 (0.7); - -

7.412 (0.6); 7.252 (1.2); 7.234 (1.1); 6.922 (1.8); 6.897 (4.3); 6.809 (1.9); 6.789 (1.4); 6.598 (1.1); 6.023 (0.5); 6.008 (0.5); 4.593 (0.6); 3.906 (7.2); 3.750 (15.1); 3.738 (16.0); 3.714 (1.0); 3.706 (0.9); 3.686 (0.7); 3.633 (3.8); 3.419 (0.7); 3.378 (0.4); 3.336 (269.7); 3.310 (1.1); 3.290 (0.5); 3.284 (0.4); 3.236 (7.0); 3.070 (0.7); 3.051 (0.8); 3.036 (1.0); 3.016 (1.0); 2.891 (0.7); 2.870 (1.5); 2.850 (1.5); 2.837 (1.1); 2.816 (0.9); 2.732 (0.3); 2.676 (0.5); 2.672 (0.6); 2.668 (0.5); 2.590 (0.5); 2.564 (0.4); 2.546 (1.7); 2.525 (1.4); 2.507 (65.2); 2.503 (85.4); 2.499 (63.3); 2.334 (0.4); 2.330 (0.6); 2.325 (0.4); 1.287 (5.3); 1.271 (5.4); 1.235 (0.8); 1.194 (2.5); 1.182 (2.6); 0.000 (4.5) Example 73: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.318 (0.4); 7.974 (0.4); 7.955 (0.6); 7.853 (6.4); 7.834 (8.5); 7.764 (0.4); 7.664 (10.5); 7.640 (7.5); 7.606 (9.9); 7.582 (6.2); 7.561 (5.2); 7.480 (0.9); 7.463 (1.2); 7.443 (1.2); 7.389 (11.4); 7.370 (6.9); 7.258 (0.4); 7.230 (0.5); 7.210 (0.7); 7.163 (3.4); 7.145 (5.4); 7.126 (3.6); 7.085 (2.8); 7.025 (2.3); 6.941 (3.3); 6.925 (3.1); 5.514 (2.2); 4.702 (2.3); 4.689 (2.3); 3.996 (16.0); 3.921 (0.7); 3.912 (0.6); 3.798 (0.3); 3.531 (2.3); 3.456 (0.5); 3.375

(1.1) ; 3.334 (147.0); 3.277 (19.7); 3.227 (3.4); 3.149 (0.5); 3.123 (0.6); 3.087 (2.8); 3.071 (3.1); 3.054 (2.8); 3.036 (2.8); 2.997 (2.3); 2.991 (2.3); 2.892 (1.1); 2.779 (2.0); 2.754 (1.6); 2.734 (1.6); 2.678 (0.6); 2.674 (0.8); 2.669 (0.6); 2.551 (6.9); 2.527 (1.4); 2.509 (89.9); 2.505 (120.0); 2.500 (88.8); 2.380 (0.4); 2.336 (0.6); 2.331 (0.8); 2.327 (0.6); 1.437 (7.8); 1.396 (14.4); 1.381 (13.7); 1.320 (1.0); 1.300 (1.0); 1.276 (0.7); 1.259 (0.9); 1.234 (2.6); 1.196 (0.7); 1.190 (0.7); 1.179 (0.8); 1.162 (0.7); 1.146 (0.7); 1.129 (0.5); 1.105 (0.4); 0.008 (0.7); 0.000 (24.6); -

0.008 (1.1)

Example 74: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.792 (2.3); 7.772 (3.2); 7.742 (0.8); 7.725 (1.2); 7.707 (2.4); 7.688 (1.8); 7.660 (2.0); 7.641 (2.4); 7.622 (1.2); 7.596 (0.7); 7.592 (0.7); 7.417 (0.6); 7.261 (1.5); 7.245 (1.4); 7.189 (2.2); 7.169 (7.8); 7.157 (7.9); 7.136 (2.9); 6.929 (1.2); 6.008 (0.5); 5.999 (0.5); 4.559 (0.8); 3.901 (6.9); 3.420 (0.8); 3.405 (0.9); 3.396 (1.0); 3.388 (1.0); 3.377 (1.1); 3.340 (503.5); 3.291 (0.5); 3.279 (0.4); 3.264 (0.5); 3.224 (8.1); 3.092 (0.9); 3.074 (1.1); 3.059 (1.3); 3.040 (1.3); 2.941 (0.4); 2.912 (0.6); 2.891 (1.1); 2.881 (1.6); 2.862 (1.5); 2.847 (1.2); 2.829 (1.1); 2.732 (0.4); 2.677 (0.6); 2.672 (0.8); 2.668 (0.7); 2.624 (0.5); 2.603 (0.4); 2.542 (2.4); 2.525 (1.6); 2.512 (41.1); 2.508 (85.5); 2.503 (114.5); 2.499 (84.3); 2.494 (41.8); 2.320 (3.1); 2.290 (16.0); 1.279 (6.9); 1.262 (7.1); 1.235 (1.2); 1.182

(2.2) ; 1.172 (2.3); 0.000 (8.0)

Example 75: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.791 (1.9); 7.772 (2.7); 7.726 (0.9); 7.708 (1.8); 7.689 (1.4); 7.660 (1.5); 7.641 (1.9); 7.622 (1.1); 7.449 (0.5); 7.267 (1.2); 7.250 (1.1); 7.219 (3.2); 7.198 (3.6); 6.944 (1.1); 6.916 (3.9); 6.895 (4.0); 6.073 (0.4); 6.059 (0.4); 4.522 (0.6); 3.902 (5.5); 3.741 (16.0); 3.400 (0.6); 3.389 (0.5); 3.365 (0.5); 3.353 (1.4); 3.335 (226.8); 3.311 (0.8); 3.297 (0.4); 3.263 (0.3); 3.220 (6.0); 3.072 (0.7); 3.053 (0.8); 3.039 (1.0); 3.020 (0.9); 2.891 (0.7); 2.864 (1.3); 2.844 (1.2); 2.830 (1.0); 2.810 (0.8); 2.677 (0.4); 2.672 (0.5); 2.668 (0.4); 2.613 (0.4); 2.525 (1.0); 2.512 (27.7);

2.507 (56.9); 2.503 (75.7); 2.498 (55.6); 2.494 (27.4); 2.334 (0.4); 2.330 (0.5); 2.325 (0.4); 1.281 (5.3); 1.265

(5.4); 1.235 (0.8); 1.178 (1.8); 1.166 (1.8); 0.000 (9.3); -0.009 (0.3)

Example 76: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.954 (1.3); 7.865 (2.7); 7.845 (3.9); 7.626 (1.7); 7.611 (2.0); 7.571 (2.1); 7.554 (2.2); 7.514 (0.5); 7.510 (0.5); 7.489 (0.6); 7.431 (4.1); 7.402 (2.4); 7.380 (3.3); 7.361 (3.4); 7.314 (0.8); 7.296 (0.7); 7.277 (0.8); 7.244 (3.7); 7.227 (2.8); 7.179 (2.0); 7.161 (3.5); 7.135 (5.9); 5.680 (1.8); 4.765 (1.1); 4.750 (1.1); 3.987 (16.0); 3.902 (0.4); 3.781 (0.3); 3.762 (0.4); 3.724 (1.3); 3.711 (1.9); 3.454 (0.5); 3.390 (0.4); 3.333 (209.1); 3.314 (10.3); 3.246 (0.4); 3.242 (0.4); 3.228 (0.4); 3.217 (0.4); 3.206 (0.4); 3.164 (1.3); 3.146 (1.4); 3.129 (1.3); 3.112 (1.1); 3.056 (1.1); 3.026 (1.6); 2.996 (1.3); 2.892 (8.9); 2.860 (1.5); 2.831 (1.1); 2.732 (7.3); 2.677 (0.5); 2.673 (0.6); 2.668 (0.5);

2.508 (75.1); 2.504 (97.1); 2.499 (71.4); 2.335 (0.5); 2.331 (0.6); 2.326 (0.5); 1.451 (5.7); 1.393 (5.8); 1.378 (5.6); 1.337 (0.8); 1.319 (0.4); 1.299 (0.6); 1.263 (0.5); 1.259 (0.6); 1.247 (0.7); 1.234 (1.5); 1.195 (0.3); 1.189 (0.3); 1.178 (0.4); 1.160 (0.4); 1.122 (0.6); 1.112 (0.6); 1.089 (0.5); 1.071 (0.5); 0.008 (0.5); 0.000 (14.3); -0.008 (0.6) Example 77: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.952 (0.4); 7.865 (2.1); 7.846 (2.3); 7.798 (2.0); 7.442 (1.5); 7.425 (2.5); 7.408 (1.7); 7.220 (3.3); 7.174 (8.6); 7.158 (8.2); 7.135 (6.5); 7.120 (7.9); 7.073 (4.6); 7.007 (3.0); 6.989 (2.5); 5.534 (1.9); 4.652 (1.2); 4.639 (1.2); 3.989 (16.0); 3.504 (1.5); 3.452 (0.4); 3.373 (1.5); 3.340 (272.8); 3.321 (12.6); 3.251 (0.5); 3.233 (0.5); 3.208

(1.1) ; 3.193 (1.2); 3.177 (1.4); 3.162 (1.3); 2.995 (0.4); 2.940 (1.7); 2.918 (2.1); 2.906 (2.3); 2.891 (2.8); 2.885

(2.2) ; 2.845 (1.2); 2.737 (0.4); 2.732 (1.0); 2.677 (1.9); 2.672 (2.0); 2.648 (1.2); 2.548 (3.8); 2.526 (1.0); 2.512 (32.8); 2.508 (67.7); 2.503 (90.1); 2.499 (67.1); 2.357 (9.8); 2.330 (1.6); 2.299 (0.4); 1.886 (11.1); 1.439 (5.8); 1.426 (6.1); 1.348 (6.2); 1.333 (6.1); 1.258 (0.4); 1.234 (1.3); 1.054 (0.5); 1.047 (0.5); 1.043 (0.5); 1.012 (0.4); 0.000 (7.7)

Example 78: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.315 (0.4); 7.785 (2.8); 7.766 (3.6); 7.719 (1.3); 7.700 (2.4); 7.682 (1.9); 7.653 (2.4); 7.635 (3.1); 7.617 (1.6); 7.510 (0.8); 7.297 (0.9); 7.271 (1.7); 7.253 (3.7); 7.236 (2.8); 7.215 (2.2); 7.197 (2.3); 7.068 (1.2); 7.005 (2.6); 6.984 (2.3); 6.950 (1.7); 6.931 (3.5); 6.913 (2.7); 6.820 (0.3); 6.118 (0.8); 6.107 (0.7); 4.641 (0.6); 3.900 (16.0); 3.812 (15.5); 3.592 (0.7); 3.472 (3.9); 3.418 (0.9); 3.398 (1.1); 3.345 (679.4); 3.313 (2.0); 3.216 (6.7); 3.176 (0.4); 3.094 (0.8); 3.075 (0.9); 3.062 (1.3); 3.042 (1.2); 2.948 (1.5); 2.929 (1.5); 2.915 (1.2); 2.892 (1.2); 2.874 (0.8); 2.843 (1.1); 2.822 (0.8); 2.746 (1.7); 2.731 (1.7); 2.714 (1.2); 2.697 (1.0); 2.677 (0.7); 2.673 (0.9); 2.668 (0.6); - 5-

2.546 (1.9); 2.526 (1.6); 2.512 (46.3); 2.508 (96.3); 2.504 (128.7); 2.499 (94.8); 2.495 (47.0); 2.335 (0.6); 2.330

(0.8); 2.326 (0.6); 2.321 (0.3); 1.273 (6.3); 1.256 (6.5); 1.235 (1.2); 1.135 (3.1); 0.000 (3.7)

Example 79: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.978 (0.4); 7.958 (0.4); 7.856 (2.2); 7.837 (2.6); 7.812 (1.6); 7.465 (0.6); 7.434 (1.4); 7.419 (2.3); 7.402 (1.6); 7.171 (6.8); 7.150 (8.4); 7.132 (6.2); 7.097 (6.6); 7.083 (7.2); 6.898 (4.6); 6.881 (3.9); 5.776 (1.2); 4.600 (1.2); 4.585 (1.2); 3.973 (8.8); 3.453 (1.4); 3.442 (1.4); 3.372 (0.7); 3.331 (88.8); 3.295 (8.9); 3.152 (1.2); 3.135 (1.4); 3.120 (1.6); 3.103 (1.5); 2.995 (0.3); 2.890 (1.6); 2.880 (1.9); 2.860 (2.3); 2.830 (1.8); 2.737 (0.4); 2.732 (0.5); 2.672 (0.6); 2.667 (0.5); 2.588 (1.0); 2.549 (4.1); 2.525 (1.0); 2.507 (56.1); 2.503 (74.3); 2.498 (55.0); 2.285 (16.0); 1.361 (4.4); 1.324 (7.0); 1.310 (6.5); 1.259 (0.7); 1.234 (1.4); 1.194 (0.3); 1.177 (0.4); 1.160 (0.4); 1.151 (0.4); 1.121 (0.3); 1.103 (0.3); 1.064 (0.4); 1.056 (0.4); 1.048 (0.4); 0.008 (0.5); 0.000 (14.9); -0.009 (0.6) Example 80: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.316 (0.5); 7.794 (5.6); 7.775 (7.0); 7.724 (1.9); 7.706 (4.2); 7.688 (3.3); 7.661 (4.1); 7.642 (5.1); 7.624 (2.5); 7.443 (0.9); 7.416 (1.6); 7.397 (3.3); 7.380 (3.9); 7.362 (2.4); 7.295 (0.4); 7.227 (2.9); 7.210 (2.8); 7.161 (7.6); 7.141 (7.4); 7.103 (2.4); 7.082 (3.6); 7.060 (1.9); 6.899 (1.3); 6.035 (0.7); 4.626 (1.5); 3.909 (9.0); 3.499 (0.8); 3.495 (0.8); 3.478 (0.8); 3.445 (0.5); 3.434 (0.5); 3.338 (825.0); 3.225 (16.0); 3.162 (1.9); 3.141 (2.1); 3.128 (2.7); 3.108 (2.4); 2.985 (3.1); 2.968 (3.3); 2.952 (2.6); 2.933 (2.1); 2.891 (0.9); 2.732 (1.1); 2.716 (0.7); 2.677 (1.4); 2.672 (1.6); 2.668 (1.2); 2.542 (3.6); 2.512 (89.5); 2.508 (163.3); 2.503 (204.2); 2.499 (148.0); 2.495 (73.2); 2.376 (0.8); 2.334 (1.1); 2.330 (1.4); 2.325 (1.0); 1.318 (12.5); 1.302 (12.8); 1.264 (0.8); 1.259 (0.9); 1.234 (2.0); 1.211 (4.9); 1.196 (4.7); 0.008 (0.7); 0.000 (10.5); -0.008 (0.5)

Example 81 : ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.316 (0.4); 7.984 (0.3); 7.966 (0.4); 7.874 (6.8); 7.856 (6.5); 7.488 (0.5); 7.443 (4.7); 7.426 (3.5); 7.406 (2.4); 7.386 (4.6); 7.369 (6.7); 7.351 (5.5); 7.288 (1.7); 7.226 (1.0); 7.189 (7.2); 7.170 (12.8); 7.151 (9.2); 7.116 (6.5); 7.032 (5.4); 6.484 (1.3); 4.674 (2.1); 3.956 (13.5); 3.874 (0.4); 3.768 (0.4); 3.747 (0.5); 3.742 (0.5); 3.717 (0.6); 3.647 (1.7); 3.580 (0.4); 3.562 (0.4); 3.536 (0.3); 3.465 (0.5); 3.381 (14.4); 3.339 (344.4); 3.268 (0.7); 3.195 (2.5); 3.048 (3.4); 3.026 (4.5); 2.996 (3.8); 2.892 (1.0); 2.846 (0.4); 2.826 (0.8); 2.778 (1.1); 2.739 (1.1); 2.734 (1.2); 2.678 (0.7); 2.673 (0.9); 2.669 (0.7); 2.527 (1.7); 2.513 (46.5); 2.509 (95.6); 2.504 (127.2); 2.500 (93.9); 2.496 (47.0); 2.336 (0.6); 2.331 (0.8); 2.327 (0.6); 1.351 (16.0); 1.338 (16.0); 1.259 (1.6); 1.234 (2.9); 1.196 (0.8); 1.188 (0.8); 1.178 (0.9); 1.160 (0.8); 1.152 (0.8); 1.131 (0.8); 1.122 (0.8); 1.113 (0.8); 1.104 (0.9); 1.096 (0.8); 0.008

(0.5); 0.000 (16.2); -0.008 (0.7)

Example 82: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.802 (2.4); 7.782 (3.1); 7.752 (1.1); 7.734 (2.1); 7.716 (2.7); 7.697 (2.0); 7.669 (2.1); 7.650 (2.5); 7.631 (1.2); 7.603 (0.7); 7.585 (1.0); 7.347 (1.0); 7.314 (1.6); 7.298 (1.4); 7.228 (2.4); 7.214 (3.6); 7.179 (6.7); 7.163 (6.7); 7.044 (1.2); 7.031 (1.0); 5.730 (0.8); 5.714 (0.8); 4.602 (0.9); 3.913 (8.3); 3.462 (0.8); 3.454 (0.8); 3.414 (0.5); 3.395 (0.7); 3.370 (2.0); 3.341 (655.4); 3.252 (9.4); 3.133 (1.1); 3.115 (1.2); 3.099 (1.5); 3.081 (1.5); 2.959 (0.6); 2.936 (2.2); 2.916 (2.1); 2.902 (2.0); 2.891 (1.3); 2.882 (1.4); 2.732 (0.7); 2.716 (0.7); 2.677 (1.2); 2.672 (1.3); 2.668 (1.0); 2.544 (2.2); 2.525 (2.0); 2.508 (107.0); 2.503 (141.9); 2.499 (104.9); 2.376 (0.6); 2.344 (16.0); 1.907

(5.0) ; 1.310 (7.7); 1.293 (7.9); 1.243 (3.2); 1.234 (3.6); 1.147 (0.4); 1.133 (0.4); 0.000 (6.2)

Example 83: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.318 (0.6); 7.803 (5.7); 7.784 (7.1); 7.746 (2.0); 7.727 (4.4); 7.709 (3.4); 7.676 (4.9); 7.657 (6.9); 7.638 (3.9); 7.583 (3.6); 7.564 (4.1); 7.533 (0.6); 7.512 (0.5); 7.501 (0.6); 7.485 (0.9); 7.464 (1.1); 7.433 (3.3); 7.416 (6.3); 7.402 (6.3); 7.383 (6.6); 7.363 (3.5); 7.349 (3.9); 7.331 (3.3); 7.286 (2.6); 7.270 (2.3); 5.968 (1.1); 4.718 (1.4); 4.709 (1.4); 3.925 (16.0); 3.711 (0.5); 3.666 (1.1); 3.479 (0.3); 3.342 (191.1); 3.286 (5.7); 3.261 (18.2); 3.158 (2.8); 3.140 (3.0); 3.123 (2.7); 3.105 (2.7); 3.062 (1.4); 3.000 (0.6); 2.902 (1.2); 2.892 (1.3); 2.876 (0.9); 2.678 (0.7); 2.673 (0.9); 2.669 (0.7); 2.509 (107.6); 2.504 (140.0); 2.500 (106.1); 2.393 (0.4); 2.373 (0.5); 2.358 (0.4); 2.349 (0.4); 2.335 (0.9); 2.331 (1.2); 2.327 (1.0); 2.288 (1.2); 2.266 (0.4); 2.223 (0.3); 2.079 (1.4); 2.063 (0.5); 1.988 (0.4); 1.623 (0.5); 1.503 (0.4); 1.344 (11.7); 1.327 (12.1); 1.234 (8.4); 1.111 (1.2); 1.095 (1.0); 0.998 (0.3);

0.979 (0.4); 0.929 (0.3); 0.910 (0.3); 0.853 (0.8); 0.835 (0.6); 0.826 (0.5); 0.806 (0.5); 0.000 (11.1)

Example 84: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.316 (0.5); 7.978 (0.9); 7.958 (1.1); 7.858 (6.8); 7.839 (8.2); 7.697 (0.7); 7.678 (0.8); 7.501 (0.4); 7.484 (0.9); 7.467 (1.5); 7.434 (3.2); 7.416 (6.0); 7.396 (6.1); 7.374 (5.5); 7.355 (5.2); 7.235 (1.2); 7.215 (1.6); 7.164 (12.4); 7.148 (15.0); 7.096 (7.0); 7.071 (6.6); 7.043 (5.6); 6.885 (4.2); 6.865 (4.9); 6.831 (3.6); 5.768 (2.2); 4.667 (2.5); 4.651 (2.6); 3.982 (15.5); 3.870 (0.4); 3.792 (0.3); 3.513 (2.5); 3.455 (0.8); 3.435 (0.5); 3.373 (2.7); 3.336 (327.3); 3.298 (20.6); 3.208 (2.4); 3.175 (3.4); 3.155 (3.1); 3.056 (0.4); 2.995 (2.1); 2.985 (3.0); 2.967 (3.7); 2.953 (3.8); 2.934 (3.7); 2.891 (2.6); 2.829 (0.4); 2.749 (0.4); 2.738 (0.8); 2.733 (1.2); 2.677 (2.6); 2.673 (2.9); 2.668 (2.5); 2.550 (7.0); 2.526 (2.1); 2.512 (61.4); 2.508 (125.1); 2.504 (165.2); 2.499 (120.5); 2.378 (0.6); 2.335 (0.8); 2.330

(1.1) ; 2.326 (0.9); 1.398 (8.2); 1.364 (16.0); 1.349 (15.0); 1.300 (1.6); 1.274 (0.9); 1.258 (1.2); 1.234 (2.9); 1.196 (0.8); 1.188 (0.8); 1.178 (0.9); 1.171 (0.9); 1.160 (0.9); 1.153 (1.1); 1.135 (0.9); 1.121 (0.7); 1.103 (0.7); 1.086 (0.5); 0.853 (0.3); 0.008 (0.8); 0.000 (25.7); -0.009 (1.1)

Example 85: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.954 (2.3); 7.884 (8.5); 7.864 (9.0); 7.648 (6.0); 7.594 (0.6); 7.579 (0.6); 7.574 (0.6); 7.519 (2.3); 7.499 (6.9); - -

7.486 (7.2); 7.456 (3.7); 7.436 (5.0); 7.418 (3.3); 7.334 (1.9); 7.273 (0.5); 7.249 (0.5); 7.193 (4.2); 7.174 (7.0); 7.156 (3.7); 7.068 (3.2); 7.050 (3.0); 4.994 (1.4); 4.983 (1.5); 4.971 (1.4); 4.875 (0.9); 4.851 (1.7); 4.832 (1.3); 4.758 (2.6); 4.734 (2.8); 4.714 (1.7); 4.654 (1.9); 4.645 (2.1); 4.631 (1.7); 4.621 (1.4); 4.575 (0.3); 3.971 (7.8); 3.330 (104.3); 3.264 (1.4); 3.227 (2.6); 3.204 (2.4); 3.145 (2.8); 3.131 (3.0); 3.110 (2.3); 3.095 (2.2); 3.061 (0.9); 2.977 (0.8); 2.891 (16.0); 2.732 (13.8); 2.677 (0.4); 2.672 (0.5); 2.668 (0.4); 2.507 (62.6); 2.503 (82.6); 2.499 (63.4); 2.334 (0.4); 2.330 (0.5); 2.326 (0.4); 1.234 (0.3); 0.007 (0.9); 0.000 (22.5); -0.001 (22.6); -0.008 (1.4) Example 86: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.953 (0.8); 7.857 (1.7); 7.837 (2.1); 7.436 (1.0); 7.419 (1.6); 7.402 (1.1); 7.221 (2.5); 7.202 (2.9); 7.166 (1.9); 7.150 (2.7); 7.087 (2.2); 6.930 (2.7); 6.910 (6.1); 6.893 (3.6); 6.859 (3.4); 5.835 (0.9); 4.569 (0.8); 4.557 (0.8); 3.974 (6.2); 3.737 (16.0); 3.431 (1.0); 3.330 (48.7); 3.289 (6.2); 3.128 (0.8); 3.111 (1.0); 3.096 (1.1); 3.079 (1.0);

2.890 (4.8); 2.862 (1.3); 2.842 (1.5); 2.831 (1.6); 2.812 (1.3); 2.731 (4.3); 2.671 (0.4); 2.575 (0.7); 2.546 (0.6); 2.525 (0.9); 2.511 (17.3); 2.507 (35.2); 2.502 (47.4); 2.498 (36.1); 1.353 (3.3); 1.327 (5.2); 1.312 (4.6); 1.234 (0.4); 0.008 (0.5); 0.000 (14.0); -0.008 (0.7)

Example 87: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.954 (0.4); 7.818 (8.0); 7.798 (10.8); 7.747 (2.5); 7.729 (6.2); 7.710 (5.2); 7.689 (6.3); 7.670 (7.3); 7.656 (11.9); 7.609 (0.4); 7.592 (0.3); 7.502 (2.8); 7.481 (16.0); 7.455 (2.6); 7.452 (2.7); 7.396 (0.5); 7.334 (0.8); 7.276 (4.0); 7.259 (3.7); 4.998 (1.7); 4.986 (1.7); 4.973 (1.7); 4.863 (1.5); 4.838 (2.7); 4.819 (2.0); 4.752 (2.7); 4.742

(3.8) ; 4.724 (3.2); 4.718 (4.1); 4.699 (2.4); 4.637 (2.4); 4.627 (2.6); 4.613 (1.9); 4.602 (1.7); 4.493 (0.4); 4.485 (0.4); 4.378 (0.4); 3.934 (7.4); 3.333 (132.4); 3.288 (37.9); 3.218 (2.1); 3.195 (2.2); 3.182 (4.7); 3.159 (4.7); 3.134

(4.9) ; 3.118 (5.1); 3.098 (2.5); 3.082 (2.2); 3.048 (0.4); 2.969 (1.1); 2.891 (2.4); 2.732 (2.2); 2.673 (0.5); 2.668 (0.4); 2.508 (60.2); 2.504 (80.9); 2.499 (61.5); 2.335 (0.4); 2.331 (0.5); 2.326 (0.4); 1.233 (0.4); 0.008 (0.6); 0.000

(18.0); -0.008 (1.0)

Example 88: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.953 (0.5); 7.805 (2.3); 7.786 (2.9); 7.743 (1.8); 7.725 (3.0); 7.706 (1.9); 7.671 (1.9); 7.652 (2.3); 7.633 (1.1); 7.603 (0.7); 7.587 (0.9); 7.352 (0.9); 7.311 (1.5); 7.294 (1.3); 7.071 (2.2); 7.052 (3.5); 7.031 (6.7); 6.971 (2.7); 6.952 (1.9); 6.814 (1.4); 5.782 (0.7); 5.766 (0.7); 5.327 (0.3); 4.589 (0.8); 4.581 (0.8); 3.903 (7.1); 3.436 (0.9); 3.371 (0.4); 3.353 (0.8); 3.332 (163.8); 3.250 (8.6); 3.079 (0.9); 3.062 (1.1); 3.046 (1.4); 3.028 (1.3); 2.931 (0.5);

2.891 (4.6); 2.874 (2.0); 2.861 (1.4); 2.841 (1.2); 2.732 (2.8); 2.676 (0.8); 2.672 (1.1); 2.667 (0.9); 2.652 (0.6); 2.619 (0.5); 2.525 (2.1); 2.507 (112.5); 2.503 (146.6); 2.498 (108.6); 2.333 (0.8); 2.329 (1.1); 2.325 (0.9); 2.286 (15.6); 2.276 (16.0); 2.213 (5.3); 2.129 (0.3); 1.894 (4.4); 1.307 (7.0); 1.290 (7.2); 1.235 (3.0); 1.230 (3.0); 1.224

(2.9); 1.144 (0.3); 1.135 (0.4); 1.124 (0.4); 0.008 (0.3); 0.000 (10.1); -0.008 (0.4)

Example 89: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.727 (4.1); 8.318 (0.4); 7.953 (0.7); 7.621 (3.7); 7.386 (0.8); 7.173 (9.7); 7.033 (0.4); 6.954 (2.1); 6.731 (1.2); 6.597 (2.2); 6.463 (1.2); 5.300 (0.9); 4.712 (1.6); 3.923 (3.7); 3.516 (0.8); 3.486 (0.7); 3.446 (0.4); 3.423 (0.5); 3.389 (0.7); 3.371 (1.6); 3.352 (2.6); 3.332 (277.3); 3.293 (10.5); 3.037 (1.8); 3.017 (1.7); 2.905 (2.6); 2.891 (6.9); 2.731 (4.3); 2.676 (1.4); 2.672 (1.8); 2.667 (1.4); 2.616 (4.7); 2.599 (10.0); 2.580 (9.8); 2.563 (4.0); 2.507 (202.7); 2.503 (249.8); 2.498 (180.6); 2.333 (1.3); 2.329 (1.7); 2.325 (1.2); 1.332 (9.5); 1.298 (4.9); 1.248 (1.9); 1.230

(2.8); 1.193 (10.3); 1.176 (16.0); 1.160 (8.8); 0.000 (13.6); -0.008 (0.6)

Example 90: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.318 (0.3); 7.953 (0.6); 7.788 (3.3); 7.769 (4.4); 7.734 (1.6); 7.704 (1.6); 7.686 (3.2); 7.667 (2.9); 7.654 (3.2); 7.635 (3.2); 7.616 (1.6); 7.599 (1.0); 7.581 (1.2); 7.360 (1.1); 7.190 (15.6); 7.184 (16.0); 7.163 (5.8); 6.962 (2.3); 6.947 (2.1); 5.830 (1.0); 5.815 (1.0); 5.300 (0.5); 4.580 (1.1); 3.905 (12.5); 3.389 (1.1); 3.371 (1.3); 3.332 (226.3); 3.235 (11.7); 3.088 (1.3); 3.069 (1.5); 3.055 (2.0); 3.036 (1.8); 2.947 (0.6); 2.919 (1.1); 2.891 (5.2); 2.877 (2.3); 2.863 (1.8); 2.843 (1.5); 2.731 (3.2); 2.671 (1.5); 2.668 (1.2); 2.617 (4.6); 2.599 (7.9); 2.580 (7.2); 2.561 (2.7); 2.507 (159.1); 2.503 (202.2); 2.498 (151.8); 2.429 (0.3); 2.329 (1.3); 1.285 (10.1); 1.269 (10.2); 1.248 (1.8); 1.229

(3.4); 1.193 (13.5); 1.174 (16.0); 1.155 (7.8); 0.000 (13.1)

Example 91 : ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.953 (0.5); 7.798 (1.4); 7.779 (2.1); 7.723 (0.6); 7.704 (1.2); 7.685 (0.9); 7.662 (1.0); 7.643 (1.2); 7.624 (0.8); 7.603 (0.5); 7.406 (0.3); 7.390 (0.4); 7.227 (0.7); 7.210 (0.7); 6.599 (5.0); 6.494 (0.4); 6.357 (1.5); 5.936 (0.4); 5.923 (0.4); 4.679 (0.4); 4.663 (0.4); 3.913 (6.1); 3.792 (0.5); 3.769 (16.0); 3.753 (2.0); 3.749 (2.2); 3.743 (1.1); 3.735 (1.0); 3.724 (0.5); 3.675 (7.1); 3.641 (10.1); 3.629 (1.6); 3.620 (1.3); 3.586 (0.4); 3.485 (0.4); 3.435 (1.0); 3.361 (0.4); 3.332 (70.6); 3.262 (5.4); 3.070 (0.5); 3.051 (0.5); 3.037 (0.7); 3.017 (0.7); 2.891 (4.2); 2.879 (1.1); 2.865 (0.8); 2.846 (0.7); 2.732 (3.1); 2.677 (0.4); 2.672 (0.5); 2.667 (0.4); 2.583 (0.4); 2.557 (0.4); 2.525 (1.3); 2.521 (1.8); 2.512 (28.2); 2.508 (59.5); 2.503 (79.6); 2.498 (58.4); 2.494 (28.9); 2.334 (0.4); 2.330 (0.5); 2.325

(0.4); 1.691 (0.4); 1.303 (3.5); 1.287 (3.5); 1.259 (0.4); 1.225 (2.8); 1.209 (2.6); 0.000 (9.5); -0.008 (0.4)

Example 92: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.737 (2.8); 7.953 (0.7); 7.691 (1.8); 7.626 (1.7); 7.393 (0.7); 6.738 (0.9); 6.603 (6.4); 6.495 (0.7); 6.468 (1.0); 6.359 (2.6); 4.812 (1.1); 4.802 (1.1); 3.938 (3.9); 3.757 (16.0); 3.669 (13.4); 3.639 (11.3); 3.572 (0.8); 3.551 (0.9); 3.378 (0.4); 3.336 (180.9); 3.310 (8.1); 3.024 (1.2); 3.005 (1.1); 2.892 (5.8); 2.732 (4.0); 2.672 (0.7); 2.573 (0.8); 2.545 (0.8); 2.507 (81.6); 2.503 (105.3); 2.500 (83.3); 2.330 (0.7); 1.691 (0.4); 1.346 (6.3); 1.307 (4.0); 0.000 - 7-

(5-9)

Example 93: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.743 (4.0); 8.704 (1.7); 8.318 (0.7); 7.953 (0.7); 7.739 (2.5); 7.725 (3.0); 7.639 (2.7); 7.568 (0.4); 7.432 (0.6); 7.354 (0.8); 7.297 (0.4); 7.238 (0.4); 7.128 (0.5); 7.100 (0.5); 7.031 (6.9); 6.974 (5.3); 6.856 (1.8); 6.797 (1.9); 6.721 (3.1); 6.587 (1.6); 6.544 (0.4); 5.359 (1.1); 4.718 (1.9); 4.704 (1.9); 3.922 (5.0); 3.545 (0.9); 3.394 (0.4);

3.336 (542.5); 3.309 (13.5); 3.045 (2.1); 3.028 (1.9); 2.891 (7.6); 2.732 (4.0); 2.677 (1.4); 2.672 (1.9); 2.668 (1.5); 2.663 (1.0); 2.632 (1.0); 2.525 (3.5); 2.521 (5.5); 2.512 (87.9); 2.508 (184.9); 2.503 (247.3); 2.499 (181.9); 2.494

(90.5) ; 2.401 (0.3); 2.334 (1.8); 2.330 (2.4); 2.325 (2.3); 2.315 (3.4); 2.289 (13.1); 2.275 (9.4); 2.257 (16.0); 2.206 (6.5); 2.096 (0.4); 1.881 (4.7); 1.337 (13.9); 1.236 (0.4); 0.008 (0.5); 0.000 (16.3); -0.009 (0.6)

Example 94: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 8.791 (9.2); 8.319 (0.4); 7.955 (2.0); 7.826 (7.8); 7.745 (11.2); 7.677 (9.9); 7.665 (10.7); 7.646 (7.4); 7.620 (14.4); 7.602 (9.6); 7.568 (1.3); 7.565 (1.3); 7.546 (0.8); 7.544 (0.8); 6.922 (2.4); 6.787 (4.7); 6.704 (0.8); 6.694 (1.0); 6.687 (0.9); 6.651 (2.3); 5.602 (2.5); 5.591 (2.5); 4.521 (0.3); 3.963 (0.6); 3.946 (0.9); 3.934 (1.2); 3.926

(1.5) ; 3.911 (1.7); 3.900 (1.8); 3.895 (1.8); 3.883 (1.5); 3.867 (1.1); 3.723 (0.5); 3.506 (0.4); 3.383 (24.5); 3.339 (282.2); 3.234 (0.4); 3.008 (12.3); 2.893 (12.8); 2.734 (10.9); 2.679 (0.8); 2.674 (1.0); 2.670 (0.8); 2.527 (2.9); 2.514 (61.9); 2.510 (125.9); 2.505 (166.6); 2.501 (124.3); 2.336 (0.8); 2.332 (1.1); 2.327 (0.8); 1.449 (15.3); 1.436 (16.0); 1.347 (1.2); 1.284 (1.6); 1.235 (1.1); 1.150 (3.7); 1.133 (3.6); 0.008 (0.5); 0.000 (14.0); -0.008 (0.6) Example 95: ^J H-NMR (400.0 MHz, de-DMSO):

δ= 7.956 (0.9); 7.821 (12.8); 7.798 (7.0); 7.762 (7.4); 7.741 (16.0); 7.721 (7.6); 7.701 (5.6); 7.682 (6.0); 7.664

(3.0) ; 7.632 (7.1); 7.610 (5.7); 7.263 (3.4); 7.248 (3.4); 5.647 (0.4); 5.630 (1.1); 5.611 (1.7); 5.594 (2.1); 5.575

(2.1) ; 5.557 (1.7); 5.538 (1.2); 5.522 (0.4); 3.899 (3.7); 3.380 (35.1); 3.339 (182.6); 2.893 (5.7); 2.734 (4.8); 2.679 (0.5); 2.674 (0.7); 2.670 (0.5); 2.528 (1.6); 2.514 (39.9); 2.510 (82.3); 2.505 (108.7); 2.501 (79.5); 2.497 (39.3);

2.337 (0.5); 2.332 (0.7); 2.328 (0.5); 1.408 (14.9); 1.390 (15.0); 1.337 (1.0); 1.234 (0.6); 1.167 (1.0); 0.000 (9.8); - 0.008 (0.3)

Example 96: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.798 (5.0); 8.789 (4.8); 7.955 (0.6); 7.773 (2.7); 7.753 (3.9); 7.737 (5.2); 7.686 (9.8); 7.675 (16.0); 7.656 (5.7); 7.602 (7.5); 6.919 (1.2); 6.784 (2.2); 6.738 (0.6); 6.730 (0.7); 6.727 (0.7); 6.720 (0.6); 6.648 (1.1); 5.631

(1.2) ; 5.616 (1.2); 3.964 (0.4); 3.947 (0.5); 3.927 (0.8); 3.911 (0.9); 3.899 (0.9); 3.883 (0.7); 3.393 (11.6); 3.340 (163.0); 3.308 (0.4); 3.003 (9.7); 2.893 (3.7); 2.734 (3.2); 2.679 (0.4); 2.674 (0.5); 2.670 (0.4); 2.528 (1.2); 2.514 (30.0); 2.510 (60.7); 2.505 (79.8); 2.501 (58.6); 2.337 (0.4); 2.332 (0.5); 2.328 (0.4); 1.459 (7.5); 1.446 (7.8); 1.347 (0.6); 1.302 (0.8); 1.234 (0.4); 1.161 (3.0); 1.144 (2.9); 0.000 (4.7)

Example 97: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.317 (0.8); 7.953 (0.4); 7.822 (5.2); 7.803 (6.4); 7.760 (3.6); 7.740 (13.2); 7.704 (7.4); 7.682 (14.1); 7.672

(16.0) ; 7.651 (3.4); 7.475 (0.6); 7.470 (0.6); 7.267 (3.1); 5.669 (0.4); 5.651 (1.1); 5.633 (1.6); 5.615 (2.2); 5.597

(2.2) ; 5.578 (1.7); 5.560 (1.1); 5.543 (0.4); 3.902 (3.0); 3.382 (34.3); 3.337 (685.3); 2.891 (2.5); 2.732 (2.1); 2.681 (0.6); 2.677 (1.4); 2.672 (1.9); 2.668 (1.4); 2.526 (4.5); 2.521 (7.5); 2.512 (114.6); 2.508 (239.3); 2.503 (318.7); 2.499 (232.9); 2.494 (114.8); 2.339 (0.8); 2.335 (1.5); 2.330 (2.1); 2.325 (1.5); 2.321 (0.8); 1.424 (13.3); 1.407

(13.6) ; 1.345 (0.9); 1.259 (0.5); 1.234 (0.7); 1.184 (0.9); 0.008 (0.6); 0.000 (18.5); -0.009 (0.7)

Example 98: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 7.955 (0.5); 7.845 (1.4); 7.815 (5.7); 7.796 (6.9); 7.750 (6.5); 7.730 (9.9); 7.722 (10.9); 7.703 (8.8); 7.675

(6.3) ; 7.657 (3.0); 7.629 (3.3); 7.608 (10.0); 7.585 (7.2); 7.564 (4.3); 7.554 (5.8); 7.535 (6.8); 7.518 (3.6); 7.426 (0.8); 7.422 (0.8); 7.196 (2.7); 7.109 (0.6); 5.706 (0.4); 5.690 (1.2); 5.671 (1.9); 5.652 (2.6); 5.634 (2.6); 5.616 (1.9); 5.598 (1.2); 5.580 (0.5); 3.908 (4.8); 3.469 (0.4); 3.381 (36.7); 3.340 (217.2); 3.305 (0.4); 2.892 (2.7); 2.734

(2.4) ; 2.678 (0.5); 2.674 (0.7); 2.670 (0.6); 2.527 (1.8); 2.509 (89.5); 2.505 (118.3); 2.501 (87.1); 2.336 (0.5); 2.332 (0.7); 2.327 (0.6); 1.389 (15.7); 1.372 (16.0); 1.293 (1.1); 1.234 (0.9); 1.186 (1.5); 1.171 (1.5); 0.000 (9.0); - 0.009 (0.3)

Example 99: ^J H-NMR (400.0 MHz, d ₆ -DMSO):

δ= 8.786 (9.8); 8.319 (0.5); 7.954 (1.3); 7.726 (8.0); 7.692 (8.3); 7.661 (12.8); 7.649 (13.7); 7.630 (10.0); 7.600 (9.3); 7.581 (10.5); 7.561 (7.1); 7.544 (9.9); 7.526 (10.7); 7.507 (5.1); 7.487 (1.4); 7.474 (1.3); 7.454 (1.3); 7.438

(1.0) ; 6.891 (2.3); 6.755 (4.4); 6.671 (0.6); 6.664 (0.7); 6.660 (0.7); 6.654 (0.7); 6.620 (2.1); 5.664 (2.6); 5.649

(2.6) ; 4.559 (0.4); 4.554 (0.4); 4.013 (0.5); 3.999 (0.4); 3.979 (0.5); 3.966 (0.7); 3.961 (0.7); 3.950 (1.0); 3.921

(2.1) ; 3.913 (2.1); 3.902 (2.1); 3.723 (0.6); 3.567 (0.3); 3.505 (0.4); 3.471 (0.7); 3.387 (23.4); 3.339 (349.4); 3.188 (0.4); 3.065 (0.4); 3.013 (7.8); 2.892 (8.6); 2.733 (7.3); 2.678 (0.8); 2.674 (1.1); 2.669 (0.8); 2.527 (2.6); 2.514

(66.1) ; 2.509 (136.4); 2.505 (180.3); 2.500 (131.0); 2.496 (64.1); 2.336 (0.8); 2.331 (1.2); 2.327 (0.9); 1.439 (15.3); 1.428 (16.0); 1.346 (1.6); 1.282 (2.1); 1.236 (1.3); 1.204 (0.5); 1.163 (0.3); 1.139 (2.5); 1.122 (2.5); 0.008 (0.4); 0.000 (14.0); -0.009 (0.5) Example A: Phytophthora infestans in vitro cell test

Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: sporocyste suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

A sporocyste suspension of P. infestans was prepared and diluted to the desired sporocyste density.

Fungicides were evaluated for their ability to inhibit sporocyste germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with sporocystes. After 8 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 66; 69; 75; 78; 80.

Example B: Pythium ultimum in vitro cell test Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: mycelial suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

Inoculum was prepared from a pre-culture of P. ultimum grown in liquid medium by homogenization using a blender. The concentration of ground mycelium in the inoculum was estimated and adjusted to the desired optical density (OD). Fungicides were evaluated for their ability to inhibit mycelium growth in liquid culture assay. The compounds were added in the desired concentrations to culture medium containing the mycelial suspension. After 4 days of incubation, the fungicidal efficacy of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 35.

Example C: Altemaria alternata in vitro cell test Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: spores suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

A spore suspension of A. alternata was prepared and diluted to the desired spore density.

Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 5 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 2; 6; 7; 14; 30; 31 ; 36; 42; 45; 48; 49; 50; 51 ; 55; 61 ; 64; 65; 66; 67; 69; 71 ; 73; 75; 76; 77; 78; 79; 80; 85; 87; 89; 90. Example D: Botrytis cinerea in vitro cell test

Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: spore suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

A spore suspension of B. cinerea was prepared and diluted to the desired spore density.

Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 5 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 2; 3; 30; 48; 49; 53; 55; 57; 61 ; 64; 94; 99.

Example E: Fusarium culmorum in vitro cell test Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: spore suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

A spore suspension of F. culmorum was prepared and diluted to the desired spore density.

Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 4 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 2; 6; 13; 14; 49; 61 ; 64; 65; 67; 68; 94.

Example F: Leptnosphaeria nodorum in vitro cell test Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: spore suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

A spore suspension of L. nodorum was prepared and diluted to the desired spore density.

Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 6 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 2; 3; 30; 49; 55; 61 ; 62; 64; 65; 67; 68; 94; 96; 99.

Example G: Phytophtora cryptogea in vitro cell test Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: mycelial suspension Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

Inoculum was prepared from a pre-culture of P. cryptogea grown in liquid medium by homogenization using a blender. The concentration of ground mycelium in the inoculum was estimated and adjusted to the desired optical density (OD).

Fungicides were evaluated for their ability to inhibit mycelium growth in liquid culture assay. The compounds were added in the desired concentrations to culture medium containing the mycelial suspension. After 6 days of incubation, the fungicidal efficacy of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 46; 66; 69; 75; 78.

Example H: Pyricularia oryzae in vitro cell test Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: spore suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

A spore suspension of P. oryzae was prepared and diluted to the desired spore density.

Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 5 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides. In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 3; 4; 5; 6; 9; 12; 13; 14; 16; 20; 23; 28; 34; 36; 38; 39; 41 ; 42; 43; 44; 45; 46; 48; 49; 50; 51 ; 54; 55; 64; 66; 68; 70; 73; 76; 83; 85; 87; 95; 97; 98.

Example I: Rhyzoctonia solani in vitro cell test Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: mycelial suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

Inoculum was prepared from a pre-culture of R. solani grown in liquid medium by homogenization using a blender. The concentration of ground mycelium in the inoculum was estimated and adjusted to the desired optical density (OD).

Fungicides were evaluated for their ability to inhibit mycelium growth in liquid culture assay. The compounds were added in the desired concentrations to culture medium containing the mycelial suspension. After 5 days of incubation, the fungicidal efficacy of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 52; 75; 76; 78; 81.

Example J: Septoria tritici in vitro cell test

Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Bacteriological Peptone (Oxoid),

1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: spore suspension Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

A spore suspension of S. tritici was prepared and diluted to the desired spore density.

Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 6 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 2; 3; 4; 13; 14; 30; 31 ; 41 ; 48; 49; 55; 61 ; 62; 65; 67; 80; 89; 94; 96; 99.

Example K: Ustttago avenue in vitro cell test Solvent: DMSO

Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: spore suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <□ 1%.

Inoculum was prepared from a pre-culture of U. avenae grown in liquid medium and diluted to the desired optical density (OD).

Fungicides were evaluated for their ability to inhibit mycelium growth in liquid culture assay. The compounds were added in the desired concentrations to culture medium containing the spore suspension. After 4 days of incubation, the fungicidal efficacy of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 20 ppm of active ingredient: 62; 64; 68; 69; 71 ; 75; 76; 77; 78; 79; 80. Example L: in vivo preventive test on Alternaria brassicae (leaf spot on radish)

Solvent: by volume of Dimethyl sulfoxide

by volume of Acetone

Emulsifier: of Tween ^® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ^® 80 and then diluted in water to the desired concentration.

The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ^® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Alternaria brassicae spores. The contaminated radish plants are incubated for 6 days at 20°C and at 100% relative humidity.

The test is evaluated 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: 3; 14; 30; 55; 61.

Example M: in vivo preventive test on Botrytis cinerea (grey mould)

Solvent: by volume of Dimethyl sulfoxide

10%) by volume of Acetone

Emulsifier: 1 μΐ of Tween ^® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ^® 80 and then diluted in water to the desired concentration.

The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ^® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Botrytis cinerea spores. The contaminated gherkin plants are incubated for 4 to 5 days at 17°C and at 90% relative humidity. The test is evaluated 4 to 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: 1 ; 2; 3; 4; 43; 49; 65.

Example N: in vivo preventive test on Phytoyhthora infestans (tomato late blight)

Solvent: by volume of Dimethyl sulfoxide

by volume of Acetone

Emulsifier: of Tween ^® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ^® 80 and then diluted in water to the desired concentration.

The young plants of tomato are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ^® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Phytophthora infestans spores. The contaminated tomato plants are incubated for 5 days at 16-18°C and at 100% relative humidity.

The test is evaluated 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: 78.

Example O: in vivo preventive test on Puccinia recondita (brown rust on wheat)

Solvent: 5% by volume of Dimethyl sulfoxide

10%) by volume of Acetone

Emulsifier: 1 μΐ of Tween ^® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ^® 80 and then diluted in water to the desired concentration.

The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ^® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants are incubated for 24 hours at 20°C and at 100%) relative humidity and then for 10 days at 20°C and at 70-80%) relative humidity. The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: 33; 54; 55; 63; 66; 69; 76; 80; 81 ; 88; 89.

Example P: in vivo preventive test on Pyrenoyhora teres (net blotch on barley)

Solvent: 5% by volume of Dimethyl sulfoxide

10%) by volume of Acetone

Emulsifier: 1 μΐ of Tween ^® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ^® 80 and then diluted in water to the desired concentration.

The young plants of barley are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ^® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Pyrenophora teres spores. The contaminated barley plants are incubated for 48 hours at 20°C and at 100%) relative humidity and then for 12 days at 20°C and at 70-80%) relative humidity.

The test is evaluated 14 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: 1 ; 2; 3; 14; 30; 31 ; 35; 38; 39; 43; 45; 46; 47; 48; 49; 50; 52; 53; 55; 56; 60; 61 ; 66; 69; 72; 75; 76; 80; 81 ; 83; 84; 92; 94; 95; 98; 99.

Example Q: in vivo preventive test on Septoria tritici (leaf spot on wheat)

Solvent: by volume of Dimethyl sulfoxide

10%) by volume of Acetone

Emulsifier: 1 μΐ of Tween ^® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ^® 80 and then diluted in water to the desired concentration. The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ^® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores. The contaminated wheat plants are incubated for 72 hours at 18°C and at 100% relative humidity and then for 21 days at 20°C and at 90%> relative humidity.

The test is evaluated 24 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: 2; 4; 27; 30; 35; 39; 41; 43; 45; 46; 48; 49; 50; 51; 53; 55; 60; 61 ; 66; 69; 72; 73; 80; 83; 84; 89; 94; 95; 96; 97; 98; 99.

Example Q: in vivo preventive test on Syhaerotheca fulisinea (powdery mildew on cucurbits)

Solvent: 5%> by volume of Dimethyl sulfoxide

10%> by volume of Acetone

Emulsifier: 1 μΐ of Tween ^® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ^® 80 and then diluted in water to the desired concentration.

The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ^® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores. The contaminated gherkin plants are incubated for 72 hours at 18°C and at 100%) relative humidity and then for 12 days at 20°C and at 70-80%) relative humidity.

The test is evaluated 15 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: 2; 3; 52; 55; 61; 76; 83; 94; 96; 99. Example R: in vivo preventive test on Uromyces appendiculatus (bean rust)

Solvent: by volume of Dimethyl sulfoxide

by volume of Acetone

Emulsifier: of Tween ^® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ^® 80 and then diluted in water to the desired concentration.

The young plants of bean are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ^® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants are incubated for 24 hours at 20°C and at 100% relative humidity and then for 10 days at 20°C and at 70-80% relative humidity.

The test is evaluated 11 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: 33; 53; 54; 55; 60; 75.