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Title:
1,2-DITHIOLONE COMPOUNDS AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2020/035826
Kind Code:
A1
Abstract:
The present invention discloses 1,2-dithiolone compounds of the formula (I), wherein, A, Cy, R, R1, R2a and R2b have the same meanings as defined in the description. The present invention further discloses methods for their preparation and the use of 1,2-dithiolone compounds of formula (I) and/or composition thereof for the protection of crops against undesired phytopathogenic microorganisms.

Inventors:
PUJARI SANDIP APPAJI (IN)
SAXENA ROHIT (IN)
THOK SAMBHAJI SHIVNATH (IN)
DEBNATH SANKHA (IN)
MISHRA RUPESH KUMAR (IN)
GARG RUCHI (IN)
AUTKAR SANTOSH SHRIDHAR (IN)
VENKATESHA HAGALAVADI M (IN)
KLAUSENER ALEXANDER G M (DE)
Application Number:
PCT/IB2019/056944
Publication Date:
February 20, 2020
Filing Date:
August 16, 2019
Export Citation:
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Assignee:
PI INDUSTRIES LTD (IN)
International Classes:
C07D339/04; A01N43/26; A01N43/34; C07D409/12
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Attorney, Agent or Firm:
VUTTS, Vaibhav et al. (IN)
Download PDF:
Claims:
CLAIMS:

1. A compound of formula (I),

Formula (I)

wherein,

R is selected from the group consisting of halogen, hydroxyl, cyano, nitro, CVCr, -alkyl, Ci-Ce- haloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, C(=0)R3, C(=0)0R3 and S(0)nR3;

R1 is selected from the group consisting of hydrogen, hydroxyl, CVCValkyl, C2-C6- alkenyl, C2- CValkynyl, C2-C6-alkenyl-Ci-C3-alkyl, C2-C6-alkynyl-Ci-C3-alkyl, Ci-Ce-haloalkyl, C2-C8- haloalkenyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C i-Cr, -cycloalky I, C 3 -C r, - h a I oc y c I o a I k y I , C3-C6- cycloalkyl-Ci-Cs-alkyl, benzyl, C(=0)R3, C(=0)0R3 and S(0)„R3;

A represents O, NR 1 " or S;

R l is selected from the group consisting of hydrogen, hydroxyl, CVCValkyl, Ci- Ce-alkoxy, C i-O, -cycloalkyl, C3-C6-cycloalkyl-Ci-C3-alkyl, benzyl, C(=0)R3, C(=0)0R3 and S(0)„R3;

R2" and R2b are independently selected from the group consisting of hydrogen, halogen, hydroxyl, Ci-CValkyl. Ci-Ce-alkoxy, CVCr, -cycloalkyl. C3-C6-cycloalkyl-Ci-C3-alkyl, C(=0)R3, C(=0)0R3 and S(0)„R3; or

R2" and R2b together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O and S, may form a 3- to 5 -member ed ring, which for its part may be substituted by one or more R3;

R3 is selected from the group consisting of hydrogen, hydroxyl, Ci-CValkyl, C 1 -CV haloalkyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl and N(R6R7);

R6 and R7 are independently selected from the group consisting of hydrogen, hydroxyl, CVCr, -alkyl, CVCVhaloalkyl, C3-Cio-cycloalkyl and S(0)„R3; All of the above mentioned groups defined in R1, R2 and R3 may carry one, two, three or four identical or different substituents selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, CVCValkyl, CVCVhaloalkyl, Ci-Ce-alkoxy and Ci-Ce-haloalkoxy;

Cy represents fused or non-fused C3-Cio-carbocyclyl or C3-Cio-heterocyclyl group which may optionally be substituted with one or more group of R4;

R4 is independently selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, nitro, Ci-CValkyl, CVCValkenyl, CVCValkynyl, CVCVhaloalkyl, C2-C8- haloalkenyl, CVCValkoxy, CVCValkenyloxy, CVCValkynyloxy, Ci-Ce-haloalkoxy, C2- CValkenyloxy, CVCVhaloalkynyloxy, Ci-Ce-alkylthio, C2-C8-alkenylthio, C2-C8- alkynylthio, Ci-Ce-haloalkylthio, C2-C8-haloalkenylthio, C3-Cio-cycloalkyl, C4-C10- cycloalkenyl, C3-Cio-cycloalkyloxy, C4-Cio-cycloalkenyloxy, C3-Cio-cycloalkylthio, C4- Cio-cycloalkenylthio, C3-Cio-cycloalkyl-Ci-C6-alkyl, C3-Cio-cycloalkyl-Ci-C6-alkyloxy, C3-Cio-cycloalkyl-Ci-C6-alkylthio, Ci-C8-alkyl-S(0)nR3, N(R6R7), C(=0)R3, C(=0)OR3, S(0)„R3, OS(0)„R3, S(0)„-C6-Cio-aryl, S(0)„-C7-Ci9-aralkyl, Ce-Cio-aryloxy, Ce-Cio-aryl and C3-Cio-heterocyclyl; all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of halogen R", OR", SR", N(R")2, Si(R")3, COOR", CN, and CON(R")2; or

two R4 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)n and Si(R')2, may form a 3- to 7-membered ring, which for its part may be substituted by one or more R5;

R5 is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, CVCValkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-CVhaloalkyl, C2-C8- haloalkenyl, C2-C8-haloalkynyl, C3-C6-cycloalkyl, C(=0)R", C(=0)OR", OR", N(R")2 and S(0)nR";

R" is selected from the group consisting of hydrogen, C CValkyl, Ci-Ce- haloalkyl, C3-Cs-cycloalkyl and N(R')2; wherein said groups are optionally substituted by one or more groups selected from the group consisting of halogen, R', OR', SR', NR'2, Si(R')3, COOR', CN, CONR'2 and CVCi 2-aryl which is optionally substituted by one or more R';

R' is selected from the group consisting of hydrogen, halogen, C CValkyl and C3-C6-cycloalkyl; n and m represent integers wherein n= 0-2, m= 1-2;

or agriculturally acceptable salts, isomer s/structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, polymorphs, metal complexes, S-oxide or N-oxides thereof;

provided that said compound of formula (I) is not 5-(benzylamino)-4-chloro-3H-l,2-dithiole-3- thione.

2. The compound of formula (I) as claimed in claim 1, wherein

A is O;

R is halogen;

R2a and R2b are independently selected from the group consisting of hydrogen, halogen, C i -Ch alky I, C3-Ce-cycloalkyl and C3-C6-cycloalkyl-Ci-C3-alkyl; or

Cy is aryl which may optionally be substituted with one or more group of R4;

R4 is independently selected from the group consisting of halogen, hydroxyl, cyano, nitro, Ci-CValkyl, CVCValkenyl, CVCValkynyk Ci-CVhaloalkyk CVCVhaloalkenyk Ci-CV alkoxy, CVCValkenyloxy, CVCValkynyloxy, Ci-Ce-haloalkoxy, CVCValkenyloxy, C2- CVhaloalkynyloxy, Ci-Ce-alkylthio, CVCValkenylthio, C2-C8-alkynylthio, Ci CV haloalkylthio, C2-Cs-haloalkenylthio, C3-Cio-cycloalkyl, C4-Cio-cycloalkenyl, C3-C10- cycloalkyloxy, C4-Cio-cycloalkenyloxy, C3-Cio-cycloalkylthio, C4-Cio-cycloalkenylthio, C3-Cio-cycloalkyl-Ci-C6-alkyl, C3-Cio-cycloalkyl-Ci-C6-alkyloxy, C3-Cio-cycloalkyl-Ci- Ce-alkylthio, Ci-C8-alkyl-S(0)nR3, N(R6R7), C(=0)R3, C(=0)OR3, S(0)nR3, OS(0)„R3, S(0)„-C6-C 10-aryl, S(0)„.C7-Ci9-aralkyl, Ce-Cio-aryloxy, Ce-Cio-aryl and C3-C10- heterocyclyl; or

two R4 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S, may form a 3- to 5-membered ring, which for its part may be substituted by one or more R5;

m is 1.

3. The compound of formula (I) as claimed in claim 1, wherein

A is O;

R is halogen;

R2' and R2b are independently selected from the group consisting of hydrogen, halogen, C 1 -Ch alky I, C3-Ce-cycloalkyl and C3-C6-cycloalkyl-Ci-C3-alkyl; or Cy is Cs-Ce-heterocyclyl group which may optionally be substituted with one or more group of R4;

R4 is independently selected from the group consisting of halogen, hydroxyl, cyano, nitro, Ci-Ce-alkyl, CVCValkenyl, CVCValkynyl, Ci-Ce-haloalkyl, CVCVhaloalkenyk Ci-Ce- alkoxy, CVCValkenyloxy, CVCValkynyloxy, Ci-Ce-haloalkoxy, CVCValkenyloxy, C2- CVhaloalkynyloxy, Ci-Ce-alkylthio, CVCValkenylthio, C2-C8-alkynylthio, Ci CV haloalkylthio, C2-C8-haloalkenylthio, C3-Cio-cycloalkyl, C4-Cio-cycloalkenyl, C3-C10- cycloalkyloxy, C4-Cio-cycloalkenyloxy, C3-Cio-cycloalkylthio, C4-Cio-cycloalkenylthio, C3-Cio-cycloalkyl-Ci-C6-alkyl, C3-Cio-cycloalkyl-Ci-C6-alkyloxy, C3-Cio-cycloalkyl-Ci- Ce-alkylthio, Ci-C8-alkyl-S(0)nR3, N(R6R7), C(=0)R3, C(=0)OR3, S(0)nR3, OS(0)„R3, S(0)„-C6-C 10-aryl, S(0)„-C7-Ci9-aralkyl, Ce-Cio-aryloxy, Ce-Cio-aryl and C3-C10- heterocyclyl; or

two R4 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S, may form a 3- to 5-membered ring, which for its part may be substituted by one or more R5;

m is 1.

4. The compound of formula (I) as claimed in claim 1, wherein said compound of formula (I) is selected from 4-chloro-5-((3,4-dimethylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5- ((3,5-dimethylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,5- difhiorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3-ethoxy-4- methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(2-

(trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl((3-methylthiophen-2- yl)methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(4-phenoxybenzyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((2-fhioro-4-methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 5- (((3-bromothiophen-2-yl)methyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5- (methyl(naphthalen-l-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(naphthalen-2- ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(3-methylbenzyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((2-ethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5- ((2,4-dimethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 5-(benzyl(methyl)amino)-4-chloro- 3H-l,2-dithiol-3-one, 4-chloro-5-((4-methoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5- ((3,4-dichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 5-(benzylamino)-4-chloro-3H-l,2-dithiol-3- one, 4-chloro-5-((l-(p-tolyl)ethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4- chlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3-(trifluoromethoxy)benzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-(methyl(2,4,6-trichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-((4-hydroxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-chloro-5- nitrobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(2-nitrobenzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-(methyl(3-nitrobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5- (methyl(4-(methylthio)benzyl)amino)-3H-l,2-dithiol-3-one, 5-((3-bromobenzyl)(methyl)amino)- 4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((2-chlorobenzyl)(methyl)amino)-3H-l,2-dithiol-3- one, 5-((4-bromobenzyl)(methyl)amino)-4-chloro-3H-l ,2-dithiol-3-one, 5-((2-bromo-4- fluorobenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((4- methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4- ethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3-chloro-4- methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-(2- hydroxyethoxy)benzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-methoxy-3- methylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-hydroxy-3- methylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4- isopropoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 5-((3-bromo-4- methoxybenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((4-hydroxy-3- methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 5-((4-butoxybenzyl)(methyl)amino)-4- chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((4-hydroxy-3,5-dimethylbenzyl)(methyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((3-chloro-4-hydroxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-(((4-chloro-3-oxo-3H-l,2-dithiol-5 -yl)(methyl)amino)methyl)-2-methoxyphenyl

methanesulfonate, 2-chloro-4-(((4-chloro-3-oxo-3H-l,2-dithiol-5- yl)(methyl)amino)methyl)phenyl methanesulfonate, 4-chloro-5 -((3,4- dimethoxybenzyl)(methyl)amino)-3H- 1 ,2-dithiol-3-one, 4-chloro-5 -((4-ethoxy-3- methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,5-dimethylbenzyl)amino)- 3H-l,2-dithiol-3-one, 5-(benzyl(isobutyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-(benzyl(prop- 2-yn-l-yl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-(benzyl(cyclopropylmethyl)amino)-4-chloro- 3H-l,2-dithiol-3-one, 5-(benzyl(cyclopropyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5- (benzyl(ethyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-(benzyl(isopropyl)amino)-4-chloro-3H- l,2-dithiol-3-one, 4-chloro-5-((3-fluoro-4-methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(4-methylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-

(dimethylamino)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,6- difluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-

(dimethylamino)benzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 5-(allyl(benzyl)amino)-4-chloro- 3H-l,2-dithiol-3-one, 4-chloro-5-((pyridin-2-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5- ((pyridin-3-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((pyridin-4-ylmethyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-(methyl(pyridin-2-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro- 5-(methyl(pyridin-3-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(pyridin-4- ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(((6-chloropyridin-3-yl)methyl)(prop-2-yn-l- yl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(((3-chloropyridin-4-yl)methyl)(methyl)amino)-3H-

1.2-dithiol-3-one, 4-chloro-5-(((3,5-dichloropyridin-4-yl)methyl)(methyl)amino)-3H-l,2-dithiol-

3-one, 4-chloro-5-(((2-chloropyridin-4-yl)methyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro- 5-((3-chlorobenzyl)amino)-3H-l,2-dithiol-3-one, 5-((3-bromobenzyl)amino)-4-chloro-3H-l,2- dithiol-3-one, 4-chloro-5-((3-chloro-4-lluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5- ((3,5-difluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(((6-chloropyridin-3- yl)methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,5-dichlorobenzyl)amino)-3H-l,2-dithiol- 3-one, 4-chloro-5-((3-lluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3- fluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-chloro-3- fluorobenzyl)amino)-3H- 1 ,2-dithiol-3-one, 4-chloro-5 -((3 ,4-difluorobenzyl)amino)-3H- 1 ,2- dithiol-3-one, 4-chloro-5-((3,4,5-trilluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3- (trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,6-difluorobenzyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-((3-chlorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-((2-chloro-6-(trifluoromethyl)benzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5- ((3,5-difluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,5- dibromobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,5- dichlorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(3-

(trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(pyrimidin-5- ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(thiophen-2-ylmethyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((pyrazin-2-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((l-(2,4- dichlorophenyl)ethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((l-phenylethyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((2-hydroxy-2-phenylethyl)amino)-3H-l,2-dithiol-3-one, 5-((2-bromo- 5-fluorobenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((3- hydroxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 5-((2-bromo-3- hydroxybenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 3-(((4-chloro-3-oxo-3H-l,2- dithiol-5-yl)(methyl)amino)methyl)phenyl methanesulfonate, 2-bromo-3-(((4-chloro-3-oxo-3H-

1.2-dithiol-5-yl)(methyl)amino)methyl)phenyl methanesulfonate, 3-(((4-chloro-3-oxo-3H- 1 ,2- dithiol-5-yl)amino)methyl)benzonitrile, 3-(((4-chloro-3-oxo-3H-l,2-dithiol-5- yl)(methyl)amino)methyl)benzonitrile, 4-(((4-chloro-3-oxo-3H-l,2-dithiol-5- yl)amino)methyl)benzonitrile, 4-(((4-chloro-3-oxo-3H-l,2-dithiol-5- yl)(methyl)ammo)methyl)benzonitrile, 4-chloro-5-((3-methoxybenzyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-((3-methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4- fluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3-methylbenzyl)amino)-3H-l,2-dithiol- 3-one, 4-chloro-5-((4-methylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,4- dimethylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-fluoro-2-methylbenzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((3,5-dimethylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2- fluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,3-dimethylbenzyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-(methyl(3-(trilluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-(ethyl(3-(trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(4- (trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(4-

(trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((cyclopropylmethyl)(3- (trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 5-(allyl(3-

(trifluoromethoxy)benzyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-((3- bromobenzyl)(cyclopropylmethyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-(allyl(3- bromobenzyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-((3-bromobenzyl)(cyclopropyl)amino)-4- chloro-3H-l,2-dithiol-3-one, 5-((l-(3-bromophenyl)ethyl)(methyl)amino)-4-chloro-3H-l,2- dithiol-3-one, 5-((l-(3-bromophenyl)ethyl)(ethyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5- (allyl( 1 -(3 -bromophenyl)ethyl)amino)-4-chloro-3H- 1 ,2-dithiol-3 -one, 5-((l-(3- bromophenyl)ethyl)(cyclopropylmethyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-

(methyl(3-((trifluoromethyl)thio)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(3-

((trifluoromethyl)thio)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(3- fluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,4-dimethoxybenzyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((2,4-difluorobenzyl)ammo)-3H-l,2-dithiol-3-one, 4-chloro-5-((4- (trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-one, 5-((4-bromobenzyl)amino)-4-chloro-3H- l,2-dithiol-3-one, 4-chloro-5-(ethyl(4-methoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5- ((4-(trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-chloro-4- fluorobenzyl)amino)-3H-l,2-dithiol-3-one, 5-((2-bromobenzyl)amino)-4-chloro-3H-l,2-dithiol-3- one, 4-chloro-5-((2-chlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,4- dimethoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,5-difluorobenzyl)ammo)-3H-l,2- dithiol-3-one, 4-chloro-5-((2,3-difluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,5- dimethoxybenzyl)amino)-3H-l ,2-dithiol-3-one, 5-((benzo[d] [1 ,3]dioxol-5-ylmethyl)amino)-4- chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((thiophen-2-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-((2-methylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,4- dichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-methoxybenzyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((2,3-dichlorobenzyl)amino)-3H-l,2-dithiol-3- 5-((4-bromo-2- fluorobenzyl)amino)-4-chloro-3H- 1 ,2-dithiol-3-one, 4-chloro-5-((2 methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(2 methoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,4-difluorobenzyl)(methyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-((2,4-difluorobenzyl)(ethyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-(methyl(4-((trifluoromethyl)thio)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,3- dimethoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-chloro-6-fluorobenzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((2,5-dichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,4- dimethylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-(methylthio)benzyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-(ethyl(4-((trifluoromethyl)thio)benzyl)amino)-3H-l ,2-dithiol-3-one, 4- chloro-5-((4-chlorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,4- dichlorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-isopropylbenzyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-((4-((trifluoromethyl)thio)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-ethoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-chloro-3- fluorobenzyl)amino)-3H-l,2-dithiol-3-one, 5-((2-bromobenzyl)(methyl)amino)-4-chloro-3H-l,2- dithiol-3-one, 4-chloro-5-(((5-chlorothiophen-2-yl)methyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,5-dimethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl((3- methylthiophen-2-yl)methyl)amino)-3H- 1 ,2-dithiol-3-one, 4-chloro-5-((2-fluoro-5- methoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3-chloro-5-fluorobenzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((3-ethoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,6- dimethylbenzyl)(ethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(2,3,6- trichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(2,3,6-trichlorobenzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((2,3-difluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-((4-fluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,3- dichlorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(4-

(trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-methoxy-2- methylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,4-dichlorobenzyl)(methyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((4-isopropylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-(methyl(2,4,6-trimethylbenzyl)amino)-3H-l,2-dithiol-3-one, 5-((3,5- bis(trifluoromethyl)benzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((4-chloro- 2-methylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-fluoro-5-methylbenzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((2,6-dimethylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-((2-chloro-6-fluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(4- (trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4- (ethylsulfonyl)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(3-

(trifluoromethyl)benzyl)amino)-3H- 1 ,2-dithiol-3 -one, 5 -(([ 1 , l'-biphenyl] -4- ylmethyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((2,3- difluorobenzyl)(ethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-ethylbenzyl)(methyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(4-lluorobenzyl)amino)-3H-l,2-dithiol-3-one, 5-((4-(tert- butyl)benzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((2,6- dimethoxybenzyl)(methyl)amino)-3H- 1 ,2-dithiol-3-one, 4-chloro-5-(methyl(2- methylbenzyl)amino)-3H-l,2-dithiol-3-one and 4-chloro-5-((2-fhiorobenzyl)(methyl)amino)-3H- l,2-dithiol-3-one.

5. A composition for controlling or preventing phytopathogenic microorganisms comprising a compound of general formula (I), N-oxide or S-oxide or agriculturally acceptable salts thereof as claimed in claim 1 and one or more inert carriers.

6. The composition as claimed in claim 5, wherein said composition may additionally comprises one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.

7. The composition as claimed in claims 5 or 6, wherein the concentration of the compound of formula (I) ranges from 10 to 90% by weight with respect to the total weight of the composition, preferably from 30 to 70% by weight with respect to the total weight of the composition.

8. A combination comprising the compound of formula (I), N-oxide, S-oxide, agriculturally acceptable salts thereof as claimed in claim 1 and one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.

9. Use of compound of formula (I), N-oxide, S-oxide, agriculturally acceptable salt, composition or combination thereof as claimed in claim 1 or 5 or 8, for controlling or preventing agricultural crops and/or horticultural crops against phytopathogenic microorganisms.

10. The use of the compound of formula (I) as claimed in claim 9, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and other vegetables, and ornamentals.

11. A seed comprising compound of formula (I), N-oxide or S-oxide or agriculturally acceptable salt thereof as claimed in claim 1 , wherein the amount of the compound of general formula (I), or an N-oxide or S-oxide or an agriculturally acceptable salt thereof, is from 0.1 g to 1 kg per 100 kg of seed.

12. A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein said compound of formula (I), agriculturally acceptable salt, composition or combination thereof as claimed in claim 1 or 5 or 8, is applied to the plants, to parts thereof or a locus thereof.

13. A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein the compound of formula (I), agriculturally acceptable salt, composition or combination thereof as claimed in claim 1 or 5 or 8, is applied to the seeds of plants.

14. A method for controlling or preventing phytopathogenic microorganisms in agricultural crops and/or horticultural crops using the compound of formula (I), agriculturally acceptable salt, composition or combination thereof as claimed in claim 1 or 5 or 8, which comprises a step of applying an effective dosage of the compound or the composition or the combination, in amounts ranging from 100 g to 2.5 kg per hectare of agricultural and/or horticultural crops.

15. A method for combating phytopathogenic fungi, comprising treating plants, soil, seeds or materials to be protected with the compound of formula (I), agriculturally acceptable salt, composition or combination thereof as claimed in claim 1 or 5 or 8.

Description:
TITLE: 1,2-Dithiolone Compounds and use thereof

FIELD OF THE INVENTION:

The present invention relates to 1,2-dithiolone compounds of formula (I). More particularly, the present invention relates to a 1,2-dithiolone compound of formula (I) and to a process for the preparation thereof. The present invention further relates to the use of 1,2-dithiolone compounds of formula (I) as disease control agents.

BACKGROUND OF THE INVENTION:

The control of damages to crops caused by phytopathogenic microorganisms is extremely important in order to achieve high crop efficiency/yield. For instance, plant disease damage to ornamental, vegetable, field, cereal and fruit crops can cause significant reduction in productivity and thereby result in increased costs for the consumer. Many products are commercially available to control such damages. But the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer and/or have different modes of action.

Certain 1,2-dithiolone compounds are disclosed in literature as microbicidal active ingredients in pesticides. For example, DE1278701, FR2541680, GB1136793, US3527867 disclose the use of 1,2- dithiolone compounds, either alone or as a part of compositions, as fungicides.

The drawback associated with prior art compounds is that the fungicidal activity of these compounds particularly at low application rates is unsatisfactory. Therefore, there is a continuous need for new compounds which are more effective, less costly, less toxic, and environmentally safer and/or have different modes of action.

In view of the above, the present invention envisages such compounds that satisfy or overcome drawbacks associated with the prior art.

It is an objective of the present invention to provide compounds having enhanced efficacy and/or a broader activity spectrum against phytopathogenic harmful fungi.

Surprisingly, this objective is achieved by the use of certain 1,2-dithiolone type compounds being disclosed in this invention, having favorable fungicidal activity against phytopathogenic fungi.

SUMMARY OF THE INVENTION:

Accordingly, the present invention provides a 1,2-dithiolone compound of formula (I),

Formula (I)

wherein, A, Cy, R, R 1 , R 2a and R 2b are as defined in the detailed description.

The present invention also relates to agriculturally acceptable salts, structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, S-oxides or N-oxides of the compound of formula (I).

The present invention further relates to a composition comprising at least one compound of formula (I) and optionally at least one other active compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and or mixtures thereof.

In one embodiment, the present invention provides the use of 1,2-dithiolone compounds of formula (I) or agriculturally acceptable salts thereof as crop protection agents for control of undesired phytopathogenic microorganisms, preferably fungal pathogens.

DETAILED DESCRIPTION OF THE INVENTION:

DEFINITIONS:

The definitions provided herein for the terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present invention disclosed in the present disclosure.

As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”,“containing”,“characterized by” or any other variation thereof, are intended to cover a non exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.

The transitional phrase“consisting of’ excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase“consisting of’ appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

The transitional phrase“consisting essentially of’ is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term“consisting essentially of’ occupies a middle ground between“comprising” and“consisting of’.

Further, unless expressly stated to the contrary,“or” refers to an inclusive“or” and not to an exclusive “or”. For example, a condition A“or” B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

Also, the indefinite articles“a” and“an” preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore“a” or“an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

As referred to in this disclosure, the term "pesticide" in each case always comprises the term "crop protection agent".

The term "undesired microorganisms" or "phytopathogenic microorganisms" such as fungal or bacterial pathogens includes namely Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae respectively.

The term“agronomic” refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).

The term“nonagronomic” refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.

Nonagronomic applications include protecting an animal from microorganisms by administering a biologically effective amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected.

In general, the term "substituted", whether preceded by the term "optionally" or not, means that at least one hydrogen present on a group (e.g., a carbon or nitrogen atom etc.) is replaced with a permissible substituent, e.g., a substituent which upon substitution results in a stable compound, e.g., a compound which does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, or other reaction under normal conditions (temperature, pressure, air etc.). Unless otherwise indicated, a "substituted" group has a substituent at one or more substitutable positions of the group, and when more than one position in any given structure is substituted, the substituent is either the same or different at each position.

The meaning of various terms used in the description as well as in claims shall now be illustrated.

The term“aliphatic compound/s” or“aliphatic group/s” used herein is an organic compound/s whose carbon atoms are linked in straight chains, branched chains, or non-aromatic rings.

The term“alkyl”, used either alone or in compound words such as“alkylthio” or“haloalkyl” or -N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched Ci to C24 alkyl, preferably Ci to C15 alkyl, more preferably Ci to C10 alkyl, most preferably Ci to Cr, alkyl. Representative examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1- ethylpropyl, hexyl, 1,1-dimethylpropyl, 1 ,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl- 1-methylpropyl and l-ethyl-2-methylpropyl or the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.

The term“alkenyl”, used either alone or in compound words includes straight-chain or branched C2 to C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to Ce alkenes. Representative examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl,

2-butenyl, 3-butenyl, 1 -methyl- 1-propenyl, 2-methyl-l-propenyl, 1-methyl -2 -propenyl, 2-methyl-2- propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl- 1-butenyl, 2-methyl- 1-butenyl, 3- methyl- 1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3 -methyl-2 -butenyl, l-methyl-3-butenyl, 2- methyl-3-butenyl, 3 -methyl-3 -butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl- 1-propenyl, l,2-dimethyl-2 -propenyl, 1 -ethyl- 1-propenyl, l-ethyl-2 -propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl- 1-pentenyl, 2-methyl- 1-pentenyl, 3-methyl-l-pentenyl, 4-methyl- 1-pentenyl, l-methyl-2- pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4 -methyl -2-pentenyl, l-methyl-3-pentenyl, 2-methyl-

3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3- methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1 -dimethyl -2 -butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-l- butenyl, 1,2-dimethyl -2 -butenyl, l,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2, 2-dimethy 1-3 -butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3- dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl- 1-butenyl, l-ethyl-2-butenyl,

1-ethyl-3-butenyl, 2-ethyl- 1-butenyl, 2-ethyl-2-butenyl, 2 -ethyl-3 -butenyl, l,l,2-trimethyl-2-propenyl, 1- ethyl-l-methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and l-ethyl-2-methyl-2 -propenyl and the different isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenyl and the like, unless defined specifically elsewhere.

The term“alkynyl”, used either alone or in compound words includes straight-chain or branched C2 to C24 alkynes, preferably C2 to C15 alkynes, more preferably C2 to C10 alkynes, most preferably C2 to Cr, alkynes. Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, l-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2- butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1 -dimethyl-2 -propynyl, 1-ethyl -

2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3- pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3 -methyl -1-pentynyl, 3- methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, l,l-dimethyl-2-butynyl, l,l-dimethyl-3- butynyl, l,2-dimethyl-3-butynyl, 2, 2-dimethy 1-3 -butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2 -butynyl, 1- ethyl-3-butynyl, 2-ethyl-3-butynyl and l-ethyl-l-methyl-2 -propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. The term“alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. The term“cycloalkyl” means alkyl closed to form a ring. Non-limiting examples include but are not limited to cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.

The term“cycloalkenyl” means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non-limiting examples include but are not limited to cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.

The term“cycloalkynyl” means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non-limiting examples include but are not limited to cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.

The term“cycloalkoxy”,“cycloalkenyloxy” and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc. , unless specifically defined elsewhere.

The term“halogen”, either alone or in compound words such as“haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as“haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Non-limiting examples of “haloalkyl” include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2- trichloroethyl, pentafluoroethyl, 1,1-di chi oro-2, 2, 2-triflu oroethyl, and l,l,l-trifluoroprop-2-yl. This definition also applies to haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere.

The terms“haloalkenyl”,“haloalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.

The term“haloalkoxy” means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-

2-fluoroethoxy, 2,2,2-trichloroethoxy, pentalluoroethoxy and l,l,l-trilluoroprop-2-oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example haloalkoxyalkyl etc., unless specifically defined elsewhere.

The term“haloalkylthio” means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and l,l,l-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.

Non-limiting examples of“haloalkylsulfinyl” include CF 3 S(0), CCUSiO), CF 3 CH 2 S(0) and CF 3 CF 2 S(0). Examples of“haloalkylsulfonyl” include CF 3 S(0) 2 , CC1 3 S(0) 2 , CF 3 CH 2 S(0) 2 and CF 3 CF 2 S(0) 2 .

The term“hydroxyl” means -OH, Amino means -NRR, wherein R can be H or any possible substituent such as alkyl. Carbonyl means -C(O)- , carbonyloxy means -OC(O)-, sulfinyl means SO, sulfonyl means S(0) 2 .

The term“alkoxy” used either alone or in compound words included Ci to C M alkoxy, preferably Ci to Cis alkoxy, more preferably Ci to Cio alkoxy, most preferably Ci to Cr, alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1- ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy,

3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1 ,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2- trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -ethyl- 1-methylpropoxy and l-ethyl-2-methylpropoxy and the different isomers. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.

The term“Alkoxyalkyl” denotes alkoxy substitution on alkyl. Non-limiting examples of “alkoxyalkyl” include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH3CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .

The term“alkoxyalkoxy” denotes alkoxy substitution on alkoxy. The term“CVCir, aryloxy group” includes, for example, a phenyloxy group, a 1-naphthyloxy group, a 2- naphthyloxy group, an 1-acenaphthyloxy group, a 1-phenanthryloxy group, an 9-anthryloxy group, and a 1-pyrenyloxy group.

The term“alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1- ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1- ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1 ,2,2-trimethylpropylthio, 1 -ethyl- 1- methylpropylthio and l-ethyl-2-methylpropylthio and the different isomers.

Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.

The term “alkylthioalkyl” denotes alkylthio substitution on alkyl. Representative examples of “alkylthioalkyl” include -CH 2 SCH 2 , -CH 2 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 . “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. The term “cycloalkylalkylamino” denotes cycloalkyl substitution on alkyl amino.

The terms alkoxyalkoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyl and the like, are defined analogously to “alkylthioalkyl” or cycloalkylalkylamino.

The term“alkoxycarbonyl” is an alkoxy group bonded to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.

The term “alkoxycarbonylalkylamino” denotes alkoxy carbonyl substitution on alkyl amino. “Alkylcarbonylalkylamino” denotes alkyl carbonyl substitution on alkyl amino. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.

Non-limiting examples of“alkylsulfinyl” include but are not limited to methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2- methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2- methylbutylsulphinyl, 3 -methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1 -ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1 ,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2- methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphinyl, 1 , 1 -dimethylbutylsulphinyl,

1.2-dimethylbutylsulphinyl, 1,3-dimethylbutylsulphinyl, 2,2-dimethylbutylsulphinyl, 2,3- dimethylbutylsulphinyl, 3, 3 -dimethylbutylsulphinyl, 1 -ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1,1,2- trimethylpropylsulphinyl, 1,2,2-trimethylpropylsulphinyl, 1 -ethyl- 1-methylpropylsulphinyl and l-ethyl-2- methylpropylsulphinyl and the different isomers. The term“arylsulfinyl” includes Ar-S(O), wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere.

Non-limiting examples of“alkylsulfonyl” include but are not limited to methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2- methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2- methylbutylsulphonyl, 3 -methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1 -ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1 ,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2- methylpentylsulphonyl, 3 -methylpentylsulphonyl, 4-methylpentylsulphonyl, 1 , 1 -dimethylbutylsulphonyl,

1.2-dimethylbutylsulphonyl, 1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3- dimethylbutylsulphonyl, 3 ,3 -dimethylbutylsulphonyl, 1 -ethylbutylsulphonyl, 2-ethylbutylsulphonyl,

1.1.2-trimethylpropylsulphonyl, 1,2,2-trimethylpropylsulphonyl, 1 -ethyl- 1-methylpropylsulphonyl and 1- ethyl-2-methylpropylsulphonyl and the different isomers. The term“arylsulfonyl” includes Ar-S(0) 2 , wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.

“Alkylamino”,“dialkylamino”, and the like, are defined analogously to the above examples.

The term "ring" or "ring system" or "Cy" as a component of formula (I) is carbocyclyl or heterocyclyl group. The term "ring system" denotes one or more rings. The term "bicyclic ring or ring system" denotes a ring system consisting of two or more common atom.

The term“carbocycle” or“carbocyclic” or“carbocyclyl” includes“aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not statisfied). Non limiting examples of non-aromatic carbocyclic ring system are cyclopropyl, cyclobutyl, cyclopentyl, norbornyl and the like. Non limiting examples of aromatic carbocyclic ring system are phenyl, naphthyl and the like.

The term "aryl" as used herein is a group that contains any carbon-based aromatic group including, but not limited to phenyl, naphthalene, biphenyl, anthracene, and the like. The aryl group can be substituted or unsubstituted. In addition, the aryl group can be a single ring structure or comprise multiple ring structures that are either fused ring structures or attached via one or more bridging groups such as a carbon-carbon bond.

The term "aralkyl" refers to aryl hydrocarbon radicals including an alkyl portion as defined above. Examples include benzyl, phenylethyl, and 6-napthylhexyl. As used herein, the term "aralkenyl" refers to aryl hydrocarbon radicals including an alkenyl portion, as defined above, and an aryl portion, as defined above. Examples include styryl, 3-(benzyl) prop-2-enyl, and 6-napthylhex-2-enyl.

The term“hetero” in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.

The term“aromatic” indicates that the Huckel rule is satisfied and the term“non-aromatic” indicates that the Huckel rule is not satisfied.

The term“heterocycle” or“heterocyclic” includes“aromatic heterocycle” or“heteroaryl ring system” and “nonaromatic heterocycle ring system” or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(0)o- 2 , and or C ring member of the heterocycle may be replaced by C(=0), C(=S), C(=CR*R*) and C=NR*, * indicates integers.

The term“non-aromatic heterocycle” or“non-aromatic heterocyclic” means three- to fifteen-membered, preferably three- to twelve-membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to) oxetanyl, oxiranyl, aziridinyl, 2- tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2- pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4- isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2- oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1- imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, l,2,4-oxadiazolidin-3-yl, l,2,4-oxadiazolidin-5-yl, l,2,4-thiadiazolidin-3-yl, l,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-l-yl, l,2,4-triazolidin-3-yl, 1,3,4- oxadiazolidin-2-yl, l,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-l-yl, l,3,4-triazolidin-2-yl, 2,3-dihydrofur- 2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3- dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3- yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin- 4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2- isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4- isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-l-yl, 2,3- dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4- dihydropyrazol-l-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5- dihydropyrazol-l-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3- dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4- dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4- dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, piperidinyl, 2-piperidinyl, 3- piperidinyl, 4-piperidinyl, pyrazynyl, morpholinyl, thiomorphlinyl, l,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2- hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5- hexahydrotriazin-2-yl, l,2,4-hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or -7- yl, 3,4,5,6-tetra-hydro[2H]azepin-2- or -3- or -4- or -5- or -6- or-7-yl, 2, 3,4,7- tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or-7- yl, 2,3,6,7-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[l H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,4,7-tetrahydro[lH]oxepin- 2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,6,7-tetrahydro[lH]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydro-l,3-diazepinyl, tetra- and hexahydro-1,4- diazepinyl, tetra- and hexahydro-l,3-oxazepinyl, tetra- and hexahydro-l,4-oxazepinyl, tetra- and hexahydro-1, 3-diox epinyl, tetra- and hexahydro-l,4-dioxepinyl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.

The term“heteroaryl” or“aromatic heterocyclic” means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5- membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms, or benzofused nitrogen-bonded 5-membered heteroaryl containing one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-l,3-diene-l,4-diyl group in which one or two carbon atoms may be replaced by nitrogen atoms, where these rings are attached to the skeleton via one of the nitrogen ring members, for example (but not limited to) 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-l- yl, 1- imidazolyl, 1,2,3-triazol-l-yl and 1,3,4-triazol-l-yl.

6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, l,3,5-triazin-2-yl, l,2,4-triazin-3-yl and l,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: for example (but not limited to) indol-l-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-l-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-l-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran-5-yl, 1- benzofuran- 6-yl, l-benzofuran-7-yl, l-benzothiophen-2-yl, l-benzothiophen-3-yl, l-benzothiophen-4-yl, 1- benzothiophen-5-yl, l-benzothiophen-6-yl, l-benzothiophen-7-yl, l,3-benzothiazol-2-yl, 1,3- benzothiazol- 4-yl, l,3-benzothiazol-5-yl, l,3-benzothiazol-6-yl, l,3-benzothiazol-7-yl, l,3-benzoxazol-2-yl, 1,3- benzoxazol-4-yl, l,3-benzoxazol-5-yl, l,3-benzoxazol-6-yl and l,3-benzoxazol-7-yl; benzofused 6- membered heteroaryl which contains one to three nitrogen atoms: for example (but not limited to) quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-l-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl.

Non-limiting examples of fused 6-5-membered heteroaryl include indolizinyl; pyrazolo[l,5-a]pyridinyl; imidazo[l,2-a]pyridinyl; pyrrolo[l,2-a]pyrimidinyl; pyrazolo[l,5-a]pyrimidinyl; imidazo[l,2- ajpyrimidinyl; pyrrolo[l,2-a]pyrazinyl; pyrazolo[l,5-a]pyrazinyl; imidazo[l,2-a]pyrazinyl and the like.

This definition also applies to heteroaryl as a part of a composite substituent, for example heteroarylalkyl etc., unless specifically defined elsewhere.

The term“Trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethyl sily 1 and t-butyl-dimethylsilyl.“Halotrialkylsilyl” denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different. The term“alkoxytrialkylsilyl” denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different. The term “trialkylsilyloxy” denotes a trialkylsilyl moiety attached through oxygen.

Non-limiting examples of“alkylcarbonyl” include C(0)CH 3 , C(0)CH 2 CH 2 CH 3 and C(0)CH(CH 3 ) 2 - Non limiting examples of “alkoxycarbonyl” include CH 3 0C(=0), CFFCFFOC^O), CFFCFFCFFOC^O), (CH 3 ) 2 CH0C(=0) and the different butoxy -or pentoxycarbonyl isomers. Non-limiting examples of ‘‘ alky laminoc arbony G’ include CH 3 NHC(=0), CH 3 CH 2 NHC(=0), CH 3 CH 2 CH 2 NHC(=0),

(CH 3 ) 2 CHNHC(=0) and the different butylamino -or pentylaminocarbonyl isomers. Non-limiting examples of“dialkylaminocarbonyl” include (CH 3 ) 2 NC(=0), (CH 3 CH 2 ) 2 NC(=0), CH 3 CH 2 (CH 3 )NC(=0), CH 3 CH 2 CH 2 (CH 3 )NC(=0) and (CH 3 ) 2 CHN(CH 3 )C(=0). Non-limiting examples of “alkoxyalkylcarbonyl” include CH 3 0CH 2 C(=0), CH 3 0CH 2 CH 2 C(=0), CH 3 CH 2 0CH 2 C(=0), CH 3 CH 2 CH 2 CH 2 0CH 2 C(=0) and CH 3 CH 2 0CH 2 CH 2 C(=0). Non-limiting examples of “alkylthioalkylcarbonyl” include CH 3 SCH 2 C(=0), CH 3 SCH 2 CH 2 C(=0), CH 3 CH 2 SCH 2 C(=0), CH 3 CH 2 CH 2 CH 2 SCH 2 C(=0) and CH 3 CH 2 SCH 2 CH 2 C(=0). The term haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously.

Non-limiting examples of“alkylaminoalkylcarbonyl” include CFFNFICFFC^O), CThNHCThCThC^O), CH 3 CH 2 NHCH 2 C(=0), CH 3 CH 2 CH 2 CH 2 NHCH 2 C(=0) and CH 3 CH 2 NHCH 2 CH 2 C(=0).

The term“amide” means A-R'C=ONR"-B, wherein R' and R" indicates substituents and A and B indicate any group.

The term“thioamide” means A-R'C=SNR"-B, wherein R' and R" indicates substituents and A and B indicate any group.

The total number of carbon atoms in a substituent group is indicated by the“Ci-C j ” prefix where i and j are numbers from 1 to 21. For example, C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C 2 alkoxyalkyl designates CH 3 OCH 2 ; C 3 alkoxyalkyl designates, for example, CFFCF^OCFF), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2 ; and C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . In the above recitations, when a compound of formula (I) is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript m in (R) m indicates an integer ranging from for example 0 to 4 then the number of substituents may be selected from the integers between 0 and 4 inclusive.

When a group contains a substituent which can be hydrogen, then, when this substituent is taken as hydrogen, it is recognized that said group is being un-substituted.

The embodiments herein and the various features and advantageous details thereof are explained with reference to the non-limiting embodiments in the description. Descriptions of well-known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.

The description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and/or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.

Any discussion of documents, acts, materials, devices, articles and the like that has been included in this specification is solely for the purpose of providing a context for the disclosure. It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this application.

The numerical values mentioned in the description and the description/claims though might form a critical part of the present invention of the present invention, any deviation from such numerical values shall still fall within the scope of the present invention if that deviation follows the same scientific principle as that of the present invention disclosed in the present invention. The inventive compound of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.

The term “pest” for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents. Also pest is an animal or plant detrimental to humans or human concerns including crops, livestock, and forestry.

The term“plant” is 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.

For the purpose of the present disclosure the term“plant” includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.

Examples of “plant” for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, corn, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea; cacao; bananas; peppers; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e.g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.

Preferably, the plant for the purpose of the present invention include but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for use of human and animals. The term“plant parts” is understood to mean all parts and organs of plants above and below the ground. For the purpose of the present disclosure the term plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxiliary buds, meristems, nodes and internodes.

The term“locus thereof’ includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.

Application of the compounds of the present invention or the compounds of the present invention in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which includes but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.

The term“applied” means adhered to a plant or plant part either physically or chemically including impregnation.

In view of the above, the present invention provides a 1,2-dithiolone compound of formula (I),

Formula (I)

wherein,

R is selected from the group consisting of halogen, hydroxyl, cyano, nitro, Ci-CValkyl, Ci-CVhaloalkyl, Ci-Ce-alkoxy, C 3 -C 6 -cycloalkyl, C(=0)R 3 , C(=0)OR 3 and S(0) n R 3 ;

R 1 is selected from the group consisting of hydrogen, hydroxyl, C CValkyl, C 2 -Ce-alkenyl, C 2 C alkynyl, C 2 -C 6 -alkenyl-Ci-C 3 -alkyl, C 2 -C 6 -alkynyl-Ci-C 3 -alkyl, Ci-CVhaloalkyl, CVCVhaloalkenyl, Ci- CValkoxy. CVCVhaloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C 3 -alkyl, benzyl, C(=0)R 3 , C(=0)OR 3 and S(0) n R 3 ;

A represents O, NR l or S;

R l is selected from the group consisting of hydrogen, hydroxyl, Ci-Ce-alkyl, Ci-Ce-alkoxy, C 3 - CVcycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C 3 -alkyl, benzyl, C(=0)R 3 , C(=0)OR 3 and S(0)„R 3 ; R 2a and R 2b are independently selected from the group consisting of hydrogen, halogen, hydroxyl, C i -C h alky I . Ci-Ce-alkoxy, CVCVcycloalkyl. C 3 -C 6 -cycloalkyl-Ci-C 3 -alkyl, C(=0)R 3 , C(=0)OR 3 and S(0)„R 3 ; or

R 2a and R 2b together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O and S, may form a 3- to 5-membered ring, which for its part may be substituted by one or more R 3 ;

R 3 is selected from the group consisting of hydrogen, hydroxyl, C i -Co-alkyl, Ci-Ce-haloalkyl, C 3 - Cio-cycloalkyl, C 3 -Cio-halocycloalkyl and N(R 6 R 7 );

R 6 and R 7 are independently selected from the group consisting of hydrogen, hydroxyl, Ci-CValkyl, Ci-CVhaloalkyl, C3-C 10 -cycloalkyl and S(0)„R 3 ;

All of the above mentioned groups defined in R 1 , R 2 and R 3 may carry one, two, three or four identical or different substituents selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, C 1 -Co al ky I, Ci-CVhaloalkyl, CVCValkoxy and CVCVhaloalkoxy;

Cy represents fused or non-fused C 3 -Cio-carbocyclyl or C 3 -Cio-heterocyclyl group which may optionally be substituted with one or more R 4 ;

R 4 is independently selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, nitro, Ci-CValkyl, CVCValkenyl, CVCValkynyl, Ci-CVhaloalkyl, CVCVhaloalkenyl, Ci-Ce- alkoxy, CVCValkenyloxy, CVCValkynyloxy, Ci-Ce-haloalkoxy, CVCValkenyloxy, C 2 -C 8 - haloalkynyloxy, Ci-CValkylthio, C 2 -C 8 -alkenylthio, C 2 -C 8 -alkynylthio, Ci-Ce-haloalkylthio, C2- C 8 -haloalkenylthio, C 3 -Cio-cycloalkyl, C 4 -Cio-cycloalkenyl, C 3 -Cio-cycloalkyloxy, C 4 -C 10 - cycloalkenyloxy, C 3 -Cio-cycloalkylthio, C 4 -Cio-cycloalkenylthio, C 3 -Cio-cycloalkyl-Ci-C 6 -alkyl, C 3 -Cio-cycloalkyl-Ci-C 6 -alkyloxy, C 3 -Cio-cycloalkyl-Ci-C 6 -alkylthio, Ci-C 8 -alkyl-S(0)„R 3 , N(R 6 R 7 ), C(=0)R 3 , C(=0)OR 3 , S(0)„R 3 , OS(0)„R 3 , S(0) n -C 6 -Cio-aryl, S(0) n -C 7 -Ci 9 -aralkyl, C 6 - Cio-aryloxy, Ce-Cio-aryl and C 3 -Cio-heterocyclyl; all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of halogen R", CN, OR", SR", N(R") 2 , Si(R") 3 , COOR", and CON(R") 2 ; or

two R 4 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0) m and Si(R') 2 , may form a 3- to 7-membered ring, which for its part may be substituted by one or more R 5 ; R 5 is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-Cr, -alkyl, CVCValkenyl, CVCValkynyl, Ci-Ce-haloalkyl, CVCVhaloalkenyl, C 2 - Cs-haloalkynyl, C 3 -C 6 -cycloalkyl, C(=0)R", C(=0)OR", OR", N(R") 2 and S(0) n R";

R" is selected from the group consisting of hydrogen, Ci-Cr, -alkyl, Ci CV haloalkyl, CVCVcycloalkyl and N(R') 2 ; wherein said groups are optionally substituted by one or more groups selected from the group consisting of halogen, R', CN, OR', SR', NR' 2 , Si(R') 3 , COOR', CONR' 2 and C 5 -Ci 2 -aryl which is optionally substituted by one or more R';

R' is selected from the group consisting of hydrogen, halogen, C 1 -C h alky I and C 3 -C 6 -cycloalkyl;

n and m represent integers wherein n= 0-2, m= 1-2;

or agriculturally acceptable salts, isomers/structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, polymorphs, metal complexes, S-oxide or N-oxides thereof;

provided that said compound of formula (I) is not 5-(benzylamino)-4-chloro-3H-l,2-dithiole-3-thione.

In one embodiment, the present invention provides a 1,2-dithiolone compound of formula (I), wherein

A is O;

R is halogen;

R 2 " and R 2b are independently selected from the group consisting of hydrogen, halogen, Ci-CValkyl, C 3 - Cr, -cycloalkyl and C 3 -C 6 -cycloalkyl-Ci-C 3 -alkyl; or

Cy is aryl which may optionally be substituted with one or more group of R 4 ;

R 4 is independently selected from the group consisting of halogen, hydroxyl, cyano, nitro, C 1 -Co-alkyl, C 2 -C 8 -alkenyl, CVCs-alkynyl, Ci-Cr, -haloalkyl, C 2 -C 8 -haloalkenyl, C CValkoxy, C 2 -C 8 -alkenyloxy, C 2 - Cs-alkynyloxy, Ci-Cr, -haloalkoxy, C 2 -C 8 -alkenyloxy, C 2 -C 8 -haloalkynyloxy, Ci-Ce-alkylthio, C 2 -Cs- alkenylthio, C 2 -C 8 -alkynylthio, Ci-Cr, -haloalkylthio, C 2 -C 8 -haloalkenylthio, C 3 -Cio-cycloalkyl, C4-C10- cycloalkenyl, C 3 -Cio-cycloalkyloxy, C4-Cio-cycloalkenyloxy, C 3 -Cio-cycloalkylthio, C4-C10- cycloalkenylthio, C 3 -Cio-cycloalkyl-Ci-C 6 -alkyl, C 3 -Cio-cycloalkyl-Ci-C 6 -alkyloxy, C 3 -Cio-cycloalkyl- Ci-Ce-alkylthio, Ci-C 8 -alkyl-S(0) n R 3 , N(R 6 R 7 ), C(=0)R 3 , C(=0)OR 3 , S(0) n R 3 , OS(0)„R 3 , OS(0)„R 3 , S(0)„-C 6 -Cio-aryl, S(0)„.C 7 -Ci 9 -aralkyl, Ce-Cio-aryloxy, Ce-Cio-aryl and C 3 -Cio-heterocyclyl; or two R 4 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S, may form a 3- to 5-membered ring, which for its part may be substituted by one or more R 5 ;

m is 1.

In another embodiment, the present invention provides a 1,2-dithiolone compound of formula (I), wherein A is O;

R is halogen;

R 2 " and R 2b are independently selected from the group consisting of hydrogen, halogen, Ci-CValkyl, C3- Cr, -cycloalkyl and C3-C6-cycloalkyl-Ci-C3-alkyl; or

Cy is CVCVheterocyclyl group which may optionally be substituted with one or more group of R 4 ;

R 4 is independently selected from the group consisting of halogen, hydroxyl, cyano, nitro, Ci-CValkyl, C2-C8-alkenyl, CVCValkynyl, Ci-CVhaloalkyl, CVCVhaloalkenyl, CVCValkoxy, CVCValkenyloxy, C2- CValkynyloxy, Ci-Ce-haloalkoxy, CVCValkenyloxy, CVCVhaloalkynyloxy, Ci-Ce-alkylthio, C2-C8- alkenylthio, C2-C8-alkynylthio, Ci-Ce-haloalkylthio, C2-Cs-haloalkenylthio, C3-Cio-cycloalkyl, C4-C10- cycloalkenyl, C3-Cio-cycloalkyloxy, C4-Cio-cycloalkenyloxy, C3-Cio-cycloalkylthio, C4-C10- cycloalkenylthio, C3-Cio-cycloalkyl-Ci-C6-alkyl, C3-Cio-cycloalkyl-Ci-C6-alkyloxy, C3-Cio-cycloalkyl- Ci-Ce-alkylthio, Ci-C 8 -alkyl-S(0)„R 3 , N(R 6 R 7 ), C(=0)R 3 , C(=0)OR 3 , S(0) n R 3 , OS(0)„R 3 , OS(0)„R 3 , S(0)„-C 6 -Cio-aryl, S(0)„.C 7 -Ci 9 -aralkyl, Ce-Cio-aryloxy, Ce-Cio-aryl and C3-Cio-heterocyclyl; or two R 4 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S, may form a 3- to 5-membered ring, which for its part may be substituted by one or more R 5 ;

m is 1.

In a preferred embodiment, the 1,2-dithiolone compound of formula (I) is selected from the group consisting of 4-chloro-5-((3,4-dimethylbenzyl)(methyl)amino)-3H-l,2-dithio l-3-one, 4-chloro-5-((3,5- dimethylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,5-difluorobenzyl)(methyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-((3-ethoxy-4-methoxybenzyl)(methyl)amino)-3H-l,2- dithiol-3-one, 4- chloro-5 -(ethyl (2-(trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3 -one, 4-chloro-5-(ethyl((3- methylthiophen-2-yl)methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(4-phenoxybenzyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-((2-fluoro-4-methoxybenzyl)(methyl)amino)-3H-l,2- dithiol-3-one, 5- (((3-bromothiophen-2-yl)methyl)(methyl)amino)-4-chloro-3H-l, 2-dithiol-3-one, 4-chloro-5-

(methyl(naphthalen-l-ylmethyl)amino)-3H-l,2-dithiol-3-one , 4-chloro-5-(methyl(naphthalen-2- ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(3-methylbenzyl)amino)-3H-l,2-dithiol-3-on e, 4-chloro-5-((2-ethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-((2,4- dimethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 5-(benzyl(methyl)amino)-4-chloro-3H-l,2- dithiol-3-one, 4-chloro-5-((4-methoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,4- dichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 5-(benzylamino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5- ((l-(p-tolyl)ethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-chlorobenzyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-((3-(trifluoromethoxy)benzyl)amino)-3H-l,2-dithio l-3-one, 4-chloro-5-(methyl(2,4,6- trichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-hydroxybenzyl)(methyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((2-chloro-5-nitrobenzyl)(methyl)amino)-3H-l,2-di thiol-3-one, 4-chloro-5- (methyl(2-nitrobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(3-nitrobenzyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-(methyl(4-(methylthio)benzyl)amino)-3H-l ,2-dithiol-3-one, 5-((3- bromobenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((2- chlorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 5-((4-bromobenzyl)(methyl)amino)-4-chloro-3H-l,2- dithiol-3-one, 5-((2-bromo-4-lluorobenzyl)(methyl)amino)-4-chloro-3H-l,2-di thiol-3-one, 4-chloro-5-((4- methoxybenzyl)(methyl)amino)-3H- 1 ,2-dithiol-3 -one, 4-chloro-5 -((4-ethoxybenzyl)(methyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((3-chloro-4-methoxybenzyl)(methyl)amino)-3H-l,2- dithiol-3-one, 4- chloro-5-((4-(2-hydroxyethoxy)benzyl)(methyl)amino)-3H-l,2-d ithiol-3-one, 4-chloro-5-((4-methoxy-3- methylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-hydroxy-3- methylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-isopropoxybenzyl)(methyl)amino)- 3H-l,2-dithiol-3-one, 5-((3-bromo-4-methoxybenzyl)(methyl)amino)-4-chloro-3H-l,2-d ithiol-3-one, 4- chloro-5-((4-hydroxy-3-methoxybenzyl)(methyl)amino)-3H-l,2-d ithiol-3-one, 5-((4- butoxybenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((4-hydroxy-3,5- dimethylbenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3-chloro-4- hydroxybenzyl)(methyl)amino)-3H-l ,2-dithiol-3-one, 4-(((4-chloro-3-oxo-3H-l ,2-dithiol-5- yl)(methyl)amino)methyl)-2-methoxyphenyl methanesulfonate, 2-chloro-4-(((4-chloro-3-oxo-3H- 1 ,2- dithiol-5-yl)(methyl)amino)methyl)phenyl methanesulfonate, 4-chloro-5-((3,4- dimethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-ethoxy-3- methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,5-dimethylbenzyl)amino)-3H-l,2- dithiol-3-one, 5-(benzyl(isobutyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-(benzyl(prop-2-yn-l- yl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-(benzyl(cyclopropylmethyl)amino)-4-chloro-3H-l,2-dithiol- 3-one, 5-(benzyl(cyclopropyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-(benzyl(ethyl)amino)-4-chloro- 3H-l,2-dithiol-3-one, 5-(benzyl(isopropyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((3-fluoro-4- methoxybenzyl)(methyl)amino)-3H- 1 ,2-dithiol-3 -one, 4-chloro-5 -(methyl(4-methylbenzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((4-(dimethylamino)benzyl)amino)-3H-l,2-dithiol-3 -one, 4-chloro-5-((2,6- difluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-

(dimethylamino)benzyl)(methyl)amino)-3H-l,2-dithiol-3-one , 5-(allyl(benzyl)amino)-4-chloro-3H-l,2- dithiol-3-one, 4-chloro-5-((pyridin-2-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((pyridin-3- ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((pyridin-4-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-(methyl(pyridin-2-ylmethyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-(methyl(pyridin-3- ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(pyridin-4-ylmethyl)amino)-3H-l,2-dithiol- 3- one, 4-chloro-5-(((6-chloropyridin-3-yl)methyl)(prop-2-yn-l-yl)am ino)-3H-l,2-dithiol-3-one, 4-chloro-5- (((3-chloropyridin-4-yl)methyl)(methyl)amino)-3H-l,2-dithiol -3-one, 4-chloro-5-(((3,5-dichloropyridin- 4-yl)methyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(((2-chloropyridin-4- yl)methyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3-chlorobenzyl)amino)-3H-l,2-dithiol-3- one, 5-((3-bromobenzyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((3-chloro-4- fluorobenzyl)amino)-3H- 1 ,2-dithiol-3-one, 4-chloro-5 -((3 ,5 -difluorobenzyl)amino)-3H- 1 ,2-dithiol-3-one, 4-chloro-5-(((6-chloropyridin-3-yl)methyl)amino)-3H-l,2-dith iol-3-one, 4-chloro-5-((3,5- dichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3-fluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3-fluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-((4-chloro-3- fluorobenzyl)amino)-3H- 1 ,2-dithiol-3-one, 4-chloro-5 -((3 ,4-difluorobenzyl)amino)-3H- 1 ,2-dithiol-3-one, 4-chloro-5-((3,4,5-trilluorobenzyl)amino)-3H-l,2-dithiol-3-o ne, 4-chloro-5-((3-

(trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,6-difluorobenzyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((3-chlorobenzyl)(methyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-((2-chloro- 6-(trifluoromethyl)benzyl)(methyl)amino)-3H-l,2-dithiol-3-on e, 4-chloro-5-((3,5- difluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,5-dibromobenzyl)(methyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-((3,5-dichlorobenzyl)(methyl)amino)-3H-l,2-dithio l-3-one, 4-chloro-5- (methyl(3-(trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-on e, 4-chloro-5-(methyl(pyrimidin-5- ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(thiophen-2-ylmethyl)amino)-3H-l,2-dithiol -3- one, 4-chloro-5-((pyrazin-2-ylmethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((l-(2,4- dichlorophenyl)ethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((l-phenylethyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-((2 -hydroxy-2 -phenylethyl)amino)-3H-l,2-dithiol-3-one, 5-((2-bromo-5- fluorobenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((3- hydroxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 5-((2-bromo-3-hydroxybenzyl)(methyl)amino)-4- chloro-3H-l,2-dithiol-3-one, 3-(((4-chloro-3-oxo-3H-l,2-dithiol-5-yl)(methyl)amino)methyl )phenyl methanesulfonate, 2-bromo-3-(((4-chloro-3-oxo-3H-l,2-dithiol-5-yl)(methyl)amin o)methyl)phenyl methanesulfonate, 3 -(((4-chloro-3-oxo-3H- 1,2-dithiol -5 -yl)amino)methyl)benzonitrile, 3-(((4-chloro-3- oxo-3H-l,2-dithiol-5-yl)(methyl)amino)methyl)benzonitrile, 4-(((4-chloro-3-oxo-3H-l,2-dithiol-5- yl)amino)methyl)benzonitrile, 4-(((4-chloro-3-oxo-3H-l,2-dithiol-5- yl)(methyl)amino)methyl)benzonitrile, 4-chloro-5-((3-methoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4- chloro-5-((3-methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-o ne, 4-chloro-5-((4-fluorobenzyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-((3-methylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4- methylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,4-dimethylbenzyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-((4-fluoro-2-methylbenzyl)amino)-3H-l,2-dithiol-3 -one, 4-chloro-5-((3,5- dimethylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-fluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,3-dimethylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(3-

(trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(3-

(trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(4-

(trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(4-

(trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((cyclopropylmethyl)(3-

(trifluoromethoxy)benzyl)amino)-3H-l,2-dithiol-3-one, 5-(allyl(3-(trifluoromethoxy)benzyl)amino)-4- chloro-3H-l,2-dithiol-3-one, 5-((3-bromobenzyl)(cyclopropylmethyl)amino)-4-chloro-3H-l,2- dithiol-3- one, 5-(allyl(3-bromobenzyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-((3- bromobenzyl)(cyclopropyl)amino)-4-chloro-3H-l,2-dithiol-3-on e, 5-((l-(3- bromophenyl)ethyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-o ne, 5-((l-(3- bromophenyl)ethyl)(ethyl)amino)-4-chloro-3H-l,2-dithiol-3-on e, 5-(allyl(l-(3- bromophenyl)ethyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 5-((l-(3- bromophenyl)ethyl)(cyclopropylmethyl)amino)-4-chloro-3H-l,2- dithiol-3-one, 4-chloro-5-(methyl(3- ((trifbioromethyl)thio)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(3-

((trifluoromethyl)thio)benzyl)amino)-3H-l,2-dithiol-3-one , 4-chloro-5-(ethyl(3-fluorobenzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((2,4-dimethoxybenzyl)amino)-3H-l,2-dithiol-3-one , 4-chloro-5-((2,4- difluorobenzyl)amino)-3H- 1 ,2-dithiol-3-one, 4-chloro-5-((4-(trifluoromethyl)benzyl)amino)-3H- 1 ,2- dithiol-3-one, 5-((4-bromobenzyl)amino)-4-chloro-3H-l ,2-dithiol-3-one, 4-chloro-5-(ethyl(4- methoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-(trifluoromethoxy)benzyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((2-chloro-4-fluorobenzyl)amino)-3H-l ,2-dithiol-3-one, 5-((2- bromobenzyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((2-chlorobenzyl)amino)-3H-l,2-dithiol- 3-one, 4-chloro-5-((3,4-dimethoxybenzyl)amino)-3H-l,2-dithiol-3-one , 4-chloro-5-((2,5- difluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,3-difluorobenzyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-((3,5-dimethoxybenzyl)amino)-3H-l,2-dithiol-3-one , 5-((benzo[d][l,3]dioxol-5- ylmethyl)amino)-4-chloro-3H- 1 ,2-dithiol-3 -one, 4-chloro-5-((thiophen-2-ylmethyl)amino)-3H- 1 ,2- dithiol-3-one, 4-chloro-5-((2-methylbenzyl)amino)-3H-l ,2-dithiol-3-one, 4-chloro-5-((2,4- dichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-methoxybenzyl)amino)-3H-l,2-dithiol-3- one, 4-chloro-5-((2,3-dichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 5-((4-bromo-2-fluorobenzyl)amino)- 4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((2-methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3 -one, 4- chloro-5-(ethyl(2-methoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,4- difluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,4-difbiorobenzyl)(ethyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-(methyl(4-((trilluoromethyl)thio)benzyl)amino)-3H -l,2-dithiol-3-one, 4- chloro-5-((2,3-dimethoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-chloro-6- fluorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,5-dichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,4-dimethylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-

(methylthio)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(ethyl(4-

((trifluoromethyl)thio)benzyl)amino)-3H-l,2-dithiol-3-one , 4-chloro-5-((4-chlorobenzyl)(methyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-((2,4-dichlorobenzyl)(methyl)amino)-3H-l,2-dithio l-3-one, 4-chloro-5- ((4-isopropylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-((trifluoromethyl)thio)benzyl)amino)- 3H-l,2-dithiol-3-one, 4-chloro-5-((4-ethoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-chloro-3- fluorobenzyl)amino)-3H-l,2-dithiol-3-one, 5-((2-bromobenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol- 3-one, 4-chloro-5-(((5-chlorothiophen-2-yl)methyl)(methyl)amino)-3H -l,2-dithiol-3-one, 4-chloro-5- ((2,5-dimethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl((3-methylthiophen-2- yl)methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-lluoro-5-methoxybenzyl)amino)-3H-l,2-dithiol- 3- one, 4-chloro-5-((3-chloro-5-fluorobenzyl)amino)-3H-l,2-dithiol-3 -one, 4-chloro-5-((3- ethoxybenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,6-dimethylbenzyl)(ethyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-(methyl(2,3,6-trichlorobenzyl)amino)-3H-l,2-dithi ol-3-one, 4-chloro-5-

(ethyl(2,3,6-trichlorobenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2,3- difluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-lluorobenzyl)(methyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-((2,3-dichlorobenzyl)(methyl)amino)-3H-l,2-dithio l-3-one, 4-chloro-5- (ethyl(4-(trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-one , 4-chloro-5-((4-methoxy-2- methylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((3,4-dichlorobenzyl)(methyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-((4-isopropylbenzyl)(methyl)amino)-3H-l,2-dithiol -3-one, 4-chloro-5-

(methyl(2,4,6-trimethylbenzyl)amino)-3H-l,2-dithiol-3-one , 5-((3,5- bis(trifluoromethyl)benzyl)(methyl)amino)-4-chloro-3H-l,2-di thiol-3-one, 4-chloro-5-((4-chloro-2- methylbenzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((2-fluoro-5-methylbenzyl)amino)-3H-l,2-dithiol- 3-one, 4-chloro-5-((2,6-dimethylbenzyl)(methyl)amino)-3H-l,2-dithio l-3-one, 4-chloro-5-((2-chloro-6- fluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(4-

(trifluoromethyl)benzyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-(ethylsulfonyl)benzyl)amino)-3H- l,2-dithiol-3-one, 4-chloro-5-(ethyl(3-(trifluoromethyl)benzyl)amino)-3H-l,2-di thiol-3-one, 5-(([1,G- biphenyl]-4-ylmethyl)(methyl)amino)-4-chloro-3H-l,2-dithiol- 3-one, 4-chloro-5-((2,3- difluorobenzyl)(ethyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-((4-ethylbenzyl)(methyl)amino)-3H-l,2- dithiol-3-one, 4-chloro-5-(ethyl(4-fluorobenzyl)amino)-3H-l,2-dithiol-3-one , 5-((4-(tert- butyl)benzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one, 4-chloro-5-((2,6- dimethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one, 4-chloro-5-(methyl(2-methylbenzyl)amino)-3H- l,2-dithiol-3-one and 4-chloro-5-((2-lluorobenzyl)(methyl)amino)-3H-l,2-dithiol-3- one.

The compounds of the present invention may be used either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.

Any of the compounds according to the 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 a person ordinary skilled in the art.

It can be advantageous to isolate or synthesize in each case the biologically more effective isomer, for example specific enantiomers or diastereomers, or isomeric mixture, for example enantiomeric mixtures or diastereomeric mixtures, if the individual components have a different biological activity. The compounds of formula (I) and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.

Any of the compounds according to the invention, can also exist in one or more amorphic or isomorphic or polymorphic forms, depending on their preparation, purification storage and various other influencing factors. The invention thus relates all the possible amorphic, isomorphic and polymorphic forms, in all proportions. The amorphic, isomorphic and polymorphic forms can be prepared and/or separated and/or purified according to general methods, which are known per se by a person ordinary skilled in the art.

In an embodiment, the present invention provides a process for preparing the compound of formula (I) or agriculturally acceptable salts thereof.

There are a large number of suitable known standard methods, such as alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction. The choice of the preparation methods which are suitable are depending on the properties (reactivity) of the substituents in the intermediates. These reactions can be conveniently performed in a solvent. These reactions can be conveniently performed at various temperatures. These reactions can be conveniently performed in an inert atmosphere. The reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialky lamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N- dimethylamine, /V,/V-diethylaniline, pyridine, 4-(/V,/V-dimethylamino)pyridine, quinuclidine, N- methylmorpholine, benzyltrimethylammonium hydroxide and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

The reaction according to scheme- 1 is preferably carried out in a solvent selected from standard solvents which are inert under the prevailing reaction conditions. Preference is given to aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, toluene; halogenated hydrocarbons such as chlorobenzene, dichloromethane, chloroform, carbon tetrachloride or dichloroethane; ethers such as diethyl ether, diisopropyl ether, methyl /-butyl ether (MTBE), dioxane, tetrahydrofuran or 1,2- dimethoxyethane; nitriles such as acetonitrile or propionitrile, or amides such as A/ZV-dimethylformamide (DMF), /V,/V-dimethylacetamide, N- m et hy I for m anilide, /V-methylpyrrolidone (NMP) or hexamethylenephosphoric triamide; esters such as methyl acetate or ethyl acetate; sulfoxides such as dimethyl sulfoxide (DMSO); sulfones such as sulfolane; alcohols such as methanol, ethanol, nor isopropanol, 1,1-, iso-, sec- or tert-butanol, ethanediol, propane- 1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether or mixtures thereof.

The reactants can be reacted with each other as such, i.e. without adding a solvent or diluent. The reaction is advantageously carried out in a temperature range from approximately -80 °C to approximately +140 °C, preferably from approximately -30 °C to approximately +100 °C, in many cases in the range between ambient temperature and approximately +80 °C.

A compound of formula (I) can be converted in a manner known per se into another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) in the customary manner by (an)other substituent(s) according to the invention. Depending on the choice of the reaction conditions and starting materials which are suitable in each case, it is possible, for example, in one reaction step only to replace one substituent by another substituent according to the invention, or a plurality of substituents can be replaced by other substituents according to the invention in the same reaction step. Salts of compounds of formula (I) can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion exchange reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchange reagent. A salt is chosen depending on its tolerances for compound's use, such as agricultural or physiological tolerance. Salts of compounds of formula (I) can be converted in the customary manner into the free compounds of formula (I), acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchange reagent. Salts of compounds of formula (I) can be converted in a manner known per se into other salts of compounds of formula (I), acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.

According to a feature of the present invention, the compounds of formula (I) can be prepared by method given in scheme 1 or examples. Representative procedures are shown below, however; the disclosure should not be construed to limit the scope of the invention arriving at compound of formula (I) as disclosed hereinabove.

Compounds of the present invention can be made as shown in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).

The compounds of the present invention as defined by formula (I) and/or in table 1 and 2 may be prepared, in known manner, by using the processes as described in general scheme 1.

Scheme: 1

The compound of formula (I) can be prepared by reacting compound 1 (1,2 dithilone derivative) and compound 2 (amine derivative) in solvent such as tetrahydrofuran, and base like triethylamine at temperature ranging from 0-100 °C.

In one embodiment, the compounds of the present invention as defined by formula (I A) and/or in table 1 and 2 may be prepared, in known manner, by using the processes as described in general scheme 2.

Scheme: 2

Formula (IA)

The step 1 is carried out by using the analogous procedure as disclosed in Antimicrobial Agents and Chemotherapy, 2004, 48(8), 3093-3102. The step 2 has been performed reacting compound 1 (1,2 dithilone derivative) and compound 2 (amine derivative) in a solvent such as tetrahydrofuran, and a base like triethylamine at a temperature ranging from 0-100 °C.

In one embodiment, the compounds of the present invention can be used for controlling undesired phytopathogenic microorganisms preferably fungal pathogens which occur in particular on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers, seeds or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these microorganisms.

The compounds of the formula (I) can possess potent microbicidal activity and can be used for the control of unwanted microorganisms, such as fungi, and bacteria, in agricultural or horticultural crop protection and in the protection of such materials. The compounds of the formula (I) possess very good fungicidal properties and can be used in crop protection, for example for control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

The compounds of the formula (I) can be used as bactericides in crop protection, for example, for control of Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

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

The compounds of the formula (I) can be used for controlling or preventing agricultural crops and/or horticultural crops against phytopathogenic microorganisms. The compounds of formula (I) can be used in crop protection, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and other vegetables, and ornamentals.

In one embodiment, the present invention provides an agrochemical composition, comprising at least one compound of formula (I) or an agriculturally acceptable salt thereof.

In another embodiment, the present invention provides a method for combating phytopathogenic fungi, comprising treating plants, soil, seeds or materials to be protected with the compound of formula (I), agriculturally acceptable salt, composition or combination thereof.

In yet another embodiment, the present invention provides a method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein said compound of formula (I), agriculturally acceptable salt, composition or combination thereof, is applied to the plants, to parts thereof, to the seeds of plants or a locus thereof.

In yet another embodiment, the present invention provides a method for controlling or preventing phytopathogenic microorganisms in agricultural crops and/or horticultural crops using the compound of formula (I), agriculturally acceptable salt, composition or combination thereof, which comprises a step of applying an effective dosage of the compound or the composition or the combination, in amounts ranging from 50 g to 5 kg per hectare of agricultural and/or horticultural crops.

In yet another embodiment, the present invention provides seed, coated with at least one compound of the formula (I) and/or an agriculturally acceptable salt thereof or with a composition in an amount of from 0.1 to 10 kg per 100 kg of seed.

The compound of formula (I) and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials.

The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coni ophora spp., Corio/us spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Ser pula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Altemaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.

The compounds of formula (I) and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:

Albugo spp. (white rust) on ornamentals, vegetables (e. g. A Candida ) and sunflowers (e. g. A tragopogonis); Alternaria spp.(Alternaria leaf spot) on vegetables, rape (A brassicola or brassi cae), sugar beets (A tenuis ), fruits, rice, soybeans, potatoes (e. g. A solani or A alternata), tomatoes (e. g. A solani or A alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A tritici (anthracnose) on wheat and A hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokiniana) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e.g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e.g. strawberries), vegetables (e.g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophio stoma) spp. (rot or wilt) on broad leaved trees and evergreens, e.g. C. ulmi (Dutch elm disease) on elms ; Cercospora spp. (Cercospora leaf spots) on corn (e.g. Gray leaf spot: C. zeaemaydis), rice, sugar beets (e.g. C. beticola), sugar cane, vegetables, coffee, soybeans (e.g. C. sojina or C. kikuchil) and rice; Cladosporium spp. on tomatoes (e.g. C. fulvum: leaf mold) and cereals, e.g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helmin thosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e.g. C. sativus, anamorph: B. sorokiniana ) and rice (e.g. C. miyabeanus, anamorph: H. oryzae ); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypit), corn (e.g. C. gramini cola: Anthracnose stalk rot), fruits, potatoes (e. g. C. coccodes: black dot), vegetables like beans (e.g. C. lindemuthianum) and soybeans (e.g. C. truncatum or C. gloeosporioides ); Corticium spp., e.g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e.g. C. oleaginum on olive trees; Cylindrocarpon spp. (e.g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e.g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e.g. D. teres, net blotch) and wheat (e.g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyn), soft fruits (E. veneta: anthracnose) and vines (E.ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pist), such as cucurbits (e.g. E. cichoracearum), cabbages, rape (e.g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e.g. E. turcicum) Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e.g. wheat or barley), F. oxysporum on tomatoes, F. solani (f. sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e.g. wheat or barley) and corn; Gib berella spp. on cereals (e. g. G. zeae ) and rice (e.g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining com plex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e.g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoft) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. jructigena( bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e.g. P. brassicae ), rape (e. g. P. parasitica), onions (e.g. P. destructor), tobacco (P. tabacina) and soybeans (e.g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e.g. on vines (e.g. P. tracheiphila and P. tetraspora) and soybeans (e.g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e.g. stem rot: P . phaseoli, teleomorph: Diaporthe phaseolorum); Phy soderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e.g. P. capsid), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad leaved trees (e.g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e.g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers ; Podosphaera spp. (powdery mildew) on rosa ceous plants, hop, pome and soft fruits, e.g. P. leucotricha on apples; Polymyxa spp., e.g. on cereals, such as barley and wheat (P. graminis ) and sugar beets (P. betae ) and thereby trans mitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e.g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e.g. P. cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila (red fire disease or, rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e.g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus ; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum ); Ramu/aria spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sa rocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soy beans (e.g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn.

Stagonospora) no dorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tucken ) on vines; Setospaeria spp. (leaf blight) on corn (e.g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e.g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Lepto sphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (po tato wart disease); Taphrina spp., e.g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e.g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incamata (grey snow mold) on barley or wheat; Urocystis spp., e.g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e.g. U. appendiculatus, syn. U. phaseoft) and sugar beets (e.g. U. betae ); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e.g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e.g. V. dahliae on strawberries, rape, potatoes and tomatoes.

In one embodiment, the present invention provides the use of compounds of formula (I) and compositions thereof, for controlling and/or preventing plant diseases caused by pathogens such as: Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea, Alternaria solani, Colletotrichum capsici, Corynespora cassicola, Septoria lycopersici, Fusarium culmorum, Phytophthora infestans, Phakopsora pachyrhizi, Sphaerotheca fuliginea, Pseudoperonospora cubensis, Puccinia triticina, Septoria tritici, Phytopthora infestans, Plasmopara viticola and Uncinula necator.

The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms.

According to the present invention, the term "stored products" is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in a processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according to the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably "stored products" is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.

The compound of formula (I) and compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds of formula (I) and compositions thereof, respectively.

The term "plant health" is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e.g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.

The term "seed" embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corns, bulbs, fruits, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.

The present invention also comprises seeds coated or treated with or containing a compound of formula (I). The term "coated or treated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate into the seed material, depending on the method of application. When the said seed product is (re)planted, it may absorb the active ingredient. In an embodiment, the present invention makes available a plant propagation material adhered thereto with a compound of formula (I). Further, it is hereby made available, a composition comprising a plant propagation material treated with a compound of formula (I).

Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. The seed treatment application of the compound formula I, which is a preferred application method, can be carried out by any known methods, such as spraying or by dusting the seeds before sowing or during the sowing/planting of the seeds.

Suitable target plants are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pome fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas or soya; oil plants, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, the plantain family, latex plants and ornamentals (such as flowers, and lawn grass or turf). In an embodiment, the plant is selected from cereals, corn, soybean, rice, sugarcane, vegetables and oil plants.

The term "plant" is to be understood as including also plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus and also plants which have been selected or hybridised to preserve and/or attain a desired trait, such as insect, fungi and /or nematode resistance. Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae or insecticidal proteins from Bacillus thuringiensis, such as 8-endotoxins, e.g. CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vipl, Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize- RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the context of the present invention there are to be understood by 8-endotoxins, for example CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C, or vegetative insecticidal proteins (Vip), for example Vipl, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinant by a new combination of different domains of those proteins (see, for example, WO 02/15701). Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WO 03/018810). Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073. The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367474, EP-A-0 401 979 and WO 90/13651. The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera). Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bbl toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bbl toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculexl® (maize variety that expresses a CrylFa2 toxin and the enzyme phosphinothricine N-acetyltransferase(PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylAc toxin); Bollgard I® (cotton variety that expresses a CrylAc toxin); Bollgard II® (cotton variety that expresses a CrylAc and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a CrylAb toxin); Newleaf® (potato variety that expresses a Cry3A toxin); NatureGard®, 25Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Btl l corn borer (CB) trait) and Protecta®. Further examples of such transgenic plants are: i) Btl l Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubi/alis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. Btl l maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium; ii)Btl76 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which have been rendered resistant to attack by the European corn borer (Ostrinia nubi/alis and Sesamia nonagrioides) by transgenic expression of a CrylAb toxin. Btl76 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium; iii) MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G- protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810; iv)MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bbl toxin and has resistance to certain Coleoptera insects; v) IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02; vi) 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NF/00/10. Genetically modified maize for the expression of the protein CrylF for achieving resistance to certain Fepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium; vii) NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 invention Brussels, Belgium, registration number C/GB/02/M3/03 consists of conventionally breed hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, including the European corn borer.

The compounds of formula (I) can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.

The compounds of formula (I) are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.

Plant propagation materials may be treated with compounds of formula (I) as such or a composition comprising at least one compound of formula (I) protectively either at or before planting or transplanting.

The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of formula (I) according to the invention.

In one embodiment, the present invention provides an agrochemical composition comprising a fungicidally effective amount of a compound of formula (I). The term "effective amount" denotes an amount of the composition or of the compounds of formula (I), which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound of formula (I) used.

The compounds of formula (I), their oxides and salts can be converted into customary types of agrochemical compositions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 61h Ed. May 2008, Croplife International.

The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F lnforma, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti- freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; dimethyl sulfoxide; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, poly electrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol. l: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar- based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.

Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines. Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound of formula (I) on the target. Examples are surfactants, minerals or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F lnforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones .

Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin. Suitable anti foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin, azo and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS) 10-60 wt% of a compound of formula (I) and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) up to 100 wt%. The active substance dissolves upon dilution with water.

ii) Dispersible concentrates (DC)

5-25 wt% of a compound of formula (I) and 1-10 wt% dispersant (e.g. polyvinyl pyrrolidone) are dissolved in up to 100 wt% organic solvent (e. g. cyclohexanone). Dilution with water gives dispersion. iii) Emulsifiable concentrates (EC)

15-70 wt% of a compound of formula (I) and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e. g. aromatic hydrocarbon). Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt% of a compound of formula (I) and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt% of a compound of formula (I) are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.

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

50-80 wt% of a compound of formula (I) are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) up to 100 wt% and prepared as water- dispersible or water-soluble granules by means of technical appliances (e.g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

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

50-80 wt% of a compound of formula (I) are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up tolOO wt% solid carrier (e.g. silica gel). Dilution with water gives a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt% of a compound of formula (I) are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethyl cellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

ix) Microemulsion (ME)

5-20 wt% of a compound of formula (I) are added to 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt% of a compound of formula (I), 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or tri-acrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1- 10 wt%. The wt% relate to the total CS composition.

xi) Dustable powders (DP, DS)

1-10 wt% of a compound of formula (I) is ground finely and mixed intimately with up tolOO wt% solid carrier (e.g. finely divided kaolin).

xii) Granules (GR, FG)

0.5-30 wt% of a compound of formula (I) is ground finely and associated with up to 100 wt% solid carrier (e. g. silicate). Granulation is achieved by extrusion, spray-drying or fluidized bed.

xiii) Ultra-low volume liquids (UL)

1-50 wt% of a compound of formula (I) are dissolved in up to 100 wt% organic solvent (e.g. aromatic hydrocarbon).

The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants. The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance.

The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum). For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The com positions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound of formula (I) and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, compound of formula (I) or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e.g. by seed dressing, pelleting, coating and dusting.

When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 100 to 2500 g per ha, preferably from 500 to 1500 g per ha, more preferably from 350 to 1000 g per ha, and in particular from 0.200 to 750 g per ha.

In treatment of plant propagation materials such as seeds, e.g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 750 g, more preferably from 10 to 500 g and most preferably from 100 to 250 g, per 100 kg of plant propagation material (preferably seeds) are generally required.

When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.01 g to 2 kg, preferably 0.05 g to 1 kg, of active substance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1, preferably 1 :10 to 10:1.

A pesticide is generally a chemical or biological agent (such as pesticidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term pesticides includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.

Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides are typically created by growing and concentrating naturally occurring organisms and/or their metabolites including bacteria and other microbes, fungi, viruses, nematodes, proteins, etc. They are often considered to be important components of integrated pest management (IPM) programs.

Biopesticides fall into two major classes, microbial and biochemical pesticides:

1. Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce) entomopathogenic nematodes are also classed as microbial pesticides, even though they are multicellular.

2. Biochemical pesticides are naturally occurring substances that control pests or provide other crop protection uses as defined below but are relatively non-toxic to mammals.

The user applies the composition according to the invention usually from a pre dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 750 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

In one embodiment, the present invention provides a composition for controlling unwanted microorganisms comprising at least one of the compounds of the formula (I) and one or more inert carrier. The inert carrier further comprises agriculturally suitable auxiliaries, solvents, diluents, surfactants and/or extenders and the like.

In another embodiment, the concentration of the compound of formula (I) ranges from 10 to 90% by weight with respect to the total weight of the composition, preferably from 30 to 70% by weight with respect to the total weight of the composition. In yet another embodiment, the present invention provides to a combination for controlling unwanted microorganisms, comprising at least one of the compounds of the formula (I) and/or one or more active compatible compound selected from fungicides, bactericides, acaricides, insecticides, nematicides, herbicides, biopesticides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof.

Generally, a compound of the present invention is used in the form of a composition (e.g. formulation) containing a carrier. A compound of the invention and compositions thereof can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra-low volume (ulv) liquid, ultra-low volume (ulv) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.

A formulation typically comprises a liquid or solid carrier and optionally one or more customary formulation auxiliaries, which may be solid or liquid auxiliaries, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and/or tackifiers. The composition may also further comprise a fertilizer, a micronutrient donor or other preparations which influence the growth of plants as well as comprising a combination containing the compound of the invention with one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.

Accordingly, the present invention also makes available a composition comprising a compound of the invention and an agronomical carrier and optionally one or more customary formulation auxiliaries.

The compositions are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid compound of the present invention and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the compound of the present invention with the auxiliary (auxiliaries). In the case of solid compounds of the invention, the grinding/milling of the compounds is to ensure specific particle size. These processes for the preparation of the compositions and the use of the compounds of the invention for the preparation of these compositions are also a subject of the invention. As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of compound according to the present invention and 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid carrier, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, of the composition to be surfactants (% in each case meaning percent by weight). Whereas concentrated compositions tend to be preferred for commercial goods, the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient.

Examples of foliar formulation types for pre-mix compositions are:

Whereas, examples of seed treatment formulation types for pre-mix compositions are:

Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.

As with the nature of the formulations, the methods of application, such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

The tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries. Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

Generally, a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15 %, of the desired ingredients, and 99.9 to 80 %, especially 99.9 to 85 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20 %, especially 0.1 to 15 %, based on the tank-mix formulation. Typically, a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95%, of the desired ingredients, and 99.9 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.

Normally, a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %, of the desired ingredients, and 99.75 to 20 %, especially 99 to 25 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.

Typically, a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.5 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation whereas commercial products will preferably be formulated as concentrates (e.g., pre-mix composition (formulation)), the end user will normally employ dilute formulations (e.g., tank mix composition).

Preferred seed treatment pre-mix formulations are aqueous suspension concentrates. The formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be pre sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compounds of the present invention are particularly suited for use in soil and seed treatment applications.

In general, the pre-mix compositions of the invention contain 0.5 to 99.9 especially 1 to 95, advantageously 1 to 50 %, by mass of the desired ingredients, and 99.5 to 0.1, especially 99 to 5%, by mass of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries (or adjuvant) can be a surfactant in an amount of 0 to 50, especially 0.5 to 40 %, by mass based on the mass of the pre-mix formulation.

A compound of the formula (I) in a preferred embodiment, independent of any other embodiments, is in the form of a plant propagation material treating (or protecting) composition, wherein said plant propagation material protecting composition may comprises additionally a colouring agent. The plant propagation material protecting composition or mixture may also comprise at least one polymer from water-soluble and water-dispersible film-forming polymers that improve the adherence of the active ingredients to the treated plant propagation material, which polymer generally has an average molecular weight of at least 10,000 to about 100,000. Examples of application methods for the compounds of the invention and compositions thereof, that is the methods of controlling pests in the agriculture, are spraying, atomizing, dusting, brushing on, dressing, scattering or pouring which are to be selected to suit the intended aims of the prevailing circumstances.

One method of application in agriculture is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest or fungi in question. Alternatively, the active ingredient can reach the plants via the root system (systemic action), by applying the compound to the locus of the plants, for example by application of a liquid composition of the compound into the soil (by drenching), or by applying a solid form of the compound in the form of granules to the soil (soil application). In the case of paddy rice plants, such granules can be metered into the flooded paddy-field. The application of the compounds of the present invention to the soil is a preferred application method.

Typical rates of application per hectare are generally 1 to 5000 g of active ingredient per hectare.

The compounds of the invention and compositions thereof are also suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the above mentioned type. The propagation material can be treated with the compound prior to planting, for example seeds can be treated prior to sowing. Alternatively, the compound can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention. Typical treatment rates would depend on the plant and pest/fungi to be controlled and are generally between 1 to 1000 grams per 100 kg of seeds, preferably between 10 to 500 grams per 100 kg of seeds, such as between 100 to 250 grams per 100 kg of seeds. The application of the compounds of the present invention to seeds is a preferred application method.

The activity of the compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding, for example, one or more insecticidally, acaricidally, nematicidally and/or fungicidally active agents. The combinations compounds of formula (I) with other insecticidally, acaricidally, nematicidally and/or fungicidally active agents may also have further surprising advantages which can also be described, in a wider sense, improved properties, for example, better tolerance by plants, reduced phytotoxicity, pests or fungi can be controlled in their different development stages or better behaviour during their production, for example during grinding or mixing, during their storage or during their use.

The following list of pesticides together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations by way of example.

The following combination of the compounds of formula (I) with other active compound is selected from the group of substances consisting of all named mixing partners of the classes (A) to (O) as described below can, if their functional groups enable this, optionally form salts with suitable bases or acids appear as stereoisomers, even if not specifically mentioned in each case, or as polymorphs. They are also understood as being included herein. These examples are:

A) Inhibitors of the ergosterol biosynthesis, for example (A01) aldimorph, (A02) azaconazole, (A03) bitertanol, (A04) bromuconazole, (A05) cyproconazole, (A06) diclobutrazole, (A07) difenoconazole, (A08) diniconazole, (A09) diniconazole-M, (A 10) dodemorph, (Al l) dodemorph acetate, (A12) epoxiconazole, (A13) etaconazole, (A14) fenarimol, (A15) fenbuconazole, (A16) fenhexamid, (A17) fenpropidin, (A18) fenpropimorph, (A19) fluquinconazole, (A20) flurprimidol, (A21) flusilazole, (A22) flutriafol, (A23) furconazole, (A24) furconazole-cis, (A25) hexaconazole, (A26) imazalil, (A27) imazalil sulfate, (A28) imibenconazole, (A29) ipconazole, (A30) metconazole, (A31) myclobutanil, (A32) naftifine, (A33) nuarimol, (A34) oxpoconazole, (A35) paclobutrazol, (A36) pefiirazoate, (A37) penconazole, (A38) piperalin, (A39) prochloraz, (A40) propiconazole, (A41) prothioconazole, (A42) pyributicarb, (A43) pyrifenox, (A44) quinconazole, (A45) simeconazole, (A46) spiroxamine, (A47) tebuconazole, (A48) terbinafine, (A49) tetraconazole, (A50) triadimefon, (A51) triadimenol, (A52) tridemorph, (A53) triflumizole, (A54) triforine, (A55) triticonazole, (A56) uniconazole, (A57) uniconazole-p, (A58) viniconazole, (A59) voriconazole, (A60) l-(4-chlorophenyl)-2-(lH-l,2,4-triazol-l- yl)cycloheptanol, (A61) methyl l-(2,2-dimethyl-2,3-dihydro-lH-inden-l-yl)-lH-imidazole-5-ca rboxylate, (A62) N'- { 5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl) propoxyjphenyl } -N-ethyl-N- methylimidoformamide, (A63) N-ethyl-N-methyl-N'- { 2-methyl-5-(trifluoromethyl)-4- [3-

(trimethylsilyl)propoxy]phenyl} imidoformamide, (A64) 0-[l-(4-methoxyphenoxy)-3,3-dimethylbutan- 2-yl]-lH-imidazole-l-carbothioate, (A65) Pyrisoxazole, (A66) 2-{ [3-(2-chlorophenyl)-2-(2,4- difhiorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l,2,4-tria zole-3-thione, (A67) l-{ [3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4-triazol-5 -yl thiocyanate, (A68) 5- (allylsulfanyl)- 1- { [3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4-triazole,

(A69) 2-[l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl]-2,4-dihydro-3H-l,2,4-triazole-3- thione, (A70) 2-{ [rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) oxiran-2-yl]methyl}-2,4-dihydro- 3H-l,2,4-triazole-3-thione, (A71) 2-{ [rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran- 2- yl]methyl}-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A72) l-{ [rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (A73) l-{ [rel(2R,3R)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4-triazol-5 -yl thiocyanate, (A74) 5 - (allylsulfanyl)- 1 - { [rel(2R,3 S)-3 -(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4- triazole, (A75) 5-(allylsulfanyl)-l-{ [rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) oxiran-2- yl]methyl}-lH- 1,2, 4-triazole, (A76) 2-[(2S,4S,5S)-l-(2,4- dichlorophenyl) -5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione , (A77) 2-[(2R,4S,5 S)-l-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-di hydro-3H-l,2,4-triazole-3-thione, (A78) 2- [(2R,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl heptan-4-yl]-2,4-dihydro-3H-l,2,4- triazole-3 -thione, (A79) 2-[(2S,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimeth ylheptan-4-yl]-

2,4-dihydro-3H-l,2,4-triazole-3-thione, (A80) 2-[(2S,4S,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazole-3-thione, (A81 ) 2- [(2R,4S ,5R)- 1 -(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-di hydro-3H-l,2,4-triazole-3-thione, (A82) 2- [(2R,4R,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl heptan-4-yl]-2,4-dihydro-3H-l,2,4- triazole-3 -thione, (A83) 2-[(2S,4R,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimeth ylheptan-4-yl]-

2.4-dihydro-3H-l,2,4-triazole-3-thione, (A84) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-

1.2.4-triazol-l-yl)propan-2-ol, (A85) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH- 1,2,4- triazol-l-yl)butan-2-ol, (A86) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-l,2, 4-triazol-l- yl)pentan-2-ol, (A87) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-l-(lH-l,2,4-triazol-l -yl)butan-2-ol, (A88) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-l-(lH-l,2,4-triaz ol-l-yl)propan-2-ol, (A89) (2R)-2-(l- chlorocyclopropyl)-4-[(lR)-2,2-dichlorocyclopropyl]-l-(lH-l, 2,4-triazol-l-yl)butan-2-ol, (A90) (2R)-2- ( 1 -chlorocyclopropyl)-4- [(1 S)-2,2-dichlorocyclopropyl] - 1 -(1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A91 ) (2S)- 2-(l -chlorocyclopropyl)-4- [( 1 S)-2,2-dichlorocyclopropyl] - 1 -(1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A92) (2S)-2-(l-chlorocyclopropyl)-4-[(lR)-2,2-dichlorocyclopropyl ]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (A93)jsh > lS ,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl- 1-(1H- 1 ,2,4-triazol- 1- ylmethyl)cyclopentanol, (A94) (lR,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(l H-l,2,4- triazol-l-ylmethyl)cyclopentanol, (A95) 5-(4-chlorobenzyl)-2- (chloromethyl)-2-methyl- 1-(1H- 1,2,4- triazol-l-ylmethyl)cyclopentanol, Other Sterol biosynthesis inhibitors: (A96)chlorphenomizole, (A97)Mefentrifluconazole.

B) Inhibitors of the respiratory chain at complex I or II, for example (B01) bixafen, (B02) boscalid, (B03) carboxin, (B04) cypropamide, (B05) diflumetorim, (B06) fenfuram, (B07) fluopyram, (B08) flutolanil, (B09) fluxapyroxad, (B10) furametpyr, (B 11) furmecyclox, (B 12) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B13) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B14) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B 15) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (B16) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (B17) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (B18) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (B19) mepronil, (B20) oxycarboxin, (B21) penflufen, (B22) penthiopyrad, (B23) pydiflumetofen, (B24) sedaxane, (B25) thifluzamide, (B26) l-methyl-N-[2-(l,l,2,2-tetrafluoroethoxy)phenyl]-3- (trifluoromethyl)-lH-pyrazole-4-carboxamide, (B27) 3-(difluoromethyl)-l-methyl-N-[2-(l, 1,2,2- tetrafluoroethoxy)phenyl]-lH-pyrazole-4-carboxamide, (B28) 3-(difluoromethyl)-N-[4-fluoro-2- (l,l,2,3,3,3-hexafluoropropoxy)phenyl]-l-methyl-lH-pyrazole- 4-carboxamide, (B29) N-[l-(2,4- dichlorophenyl)-l-methoxypropan-2-yl]-3-(difluoromethyl)-l-m ethyl-lH-pyrazole-4-carboxamide, (B30) 5 , 8-difluoro-N- [2-(2-fluoro-4- { [4-(trifluoromethyl)pyridin-2-yl] oxy }pyhenyl)ethyl] quinazolin-4-amine, (B31) benzovindiflupyr, (B32) N-[(lS,4R)-9-(dichloromethylene)-l,2,3,4-tetrahydro-l,4- methanonaphthalen-5-yl] -3 -(difluoromethyl)-l -methyl- lH-pyrazole-4-carboxamide, (B33) N-[(lR,4S)-9- (dichloromethylene)-l,2,3,4-tetrahydro-l,4-methanonaphthalen -5-yl]-3-(difluoromethyl)-l-methyl-lH- pyrazole-4-carboxamide, (B34) 3-(difluoromethyl)-l-methyl-N-(l,l,3-trimethyl-2,3-dihydro-l H-inden-4- yl)-lH-pyrazole-4-carboxamide, (B35) l,3,5-trimethyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl )- lH-pyrazole-4-carboxamide, (B36) l-methyl-3-(trifluoromethyl)-N-(l,l,3-trimethyl-2,3-dihydro- lH- inden-4-yl)- lH-pyrazole-4-carboxamide, (B37) 1 -methyl-3-(trifluoromethyl)-N-[(3R)- 1 , 1 , 3-trimethyl -

2.3-dihydro-lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (B38) l-methyl-3-(trifluoromethyl)-N- [(3S)-

1.1.3-bimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4-c arboxamide, (B39) 3-(difluoromethyl)-l- methyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH -pyrazole-4-carboxamide, (B40) 3-

(difluoromethyl)-l-methyl-N-[(3R)-l,l,3-trimethyl-2,3-dih ydro-lH-inden-4-yl]-lH-pyr azole-4- carboxamide, (B41) l,3,5-trimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden -4-yl]-lH-pyrazole-4- carboxamide, (B42) l,3,5-trimethyl-N-[(3S)-l,l,3- trimethyl-2, 3-dihydro-lH-inden-4-yl]-lH-pyrazole-4- carboxamide, (B43) benodanil, (B44) 2-chloro-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)pyridi ne-3- carboxamide, (B45) Isofetamid, (B46) l-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl -2- yl]-lH-pyrazole-4-carboxamide, (B47) N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-l-methyl-lH- pyrazole-4-carboxamide, (B48) N-(2',4'-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-l-methyl- lH- pyrazole-4-carboxamide, (B49) 3-(difluoromethyl)-l-methyl-N-[4'-(trifluoromethyl)biphenyl- 2-yl]-lH- pyrazole-4-carboxamide, (B50) N-(2',5 '-difluorobiphenyl-2-yl)-l-methyl-3-(trifluoromethyl)-lH- pyrazole-4-carboxamide, (B51) 3-(difluoromethyl)-l-methyl-N-[4'-(prop-l-yn-l-yl)biphenyl-2 -yl]-lH- pyrazole-4-carboxamide, (B52) 5-fluoro-l,3-dimethyl-N-[4'-(prop-l-yn-l-yl)biphenyl-2-yl]-l H-pyrazole- 4-carboxamide, (B53) 2-chloro-N-[4'-(prop-l-yn-l-yl)biphenyl-2-yl]nicotinamide, (B54) 3-

(difluoromethyl)-N- [4'-(3,3-dimethylbut-l-yn-l-yl)biphenyl-2-yl]-l-methyl-lH-py razole-4-carboxamide, (B55) N-[4'-(3,3-dimethylbut-l-yn-l-yl)biphenyl-2- yl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4- carboxamide, (B56) 3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-l-methyl-lH-p yrazole-4- carboxamide, (B57) N-(4‘-ethynylbiphenyl-2-yl)-5-fluoro-l,3-dimethyl-lH-pyraz ole-4-carboxamide, (B58) 2-chloro-N-(4'-ethynylbiphenyl-2-yl)nicotinamide, (B59) 2-chloro-N-[4'-(3,3-dimethylbut-l-yn-l- yl)biphenyl-2-yl] nicotinamide, (B60) 4-(difluoromethyl)-2-methyl-N-[4’-(trifluoromethyl)bipheny l-2-yl]-

1.3-thiazole-5-carboxamide, (B61) 5-fluoro-N-[4'-(3-hydroxy-3-methylbut-l-yn-l-yl)biphenyl-2-y l]-l,3- dimethyl- lH-pyrazole-4-carboxamide, (B62) 2-chloro-N-[4'-(3-hydroxy-3-methylbut-l-yn-l-yl)biphenyl- 2-yl]nicotinamide, (B63) 3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-l-yn-l-yl)bi phenyl-2-yl]-l- methyl- lH-pyrazole-4-carboxamide, (B64) 5 -fluoro-N - [4'-(3 -methoxy-3 -methylbut- 1 -yn- 1 -yl)biphenyl-2- yl]-l, 3-dimethyl- lH-pyrazole-4-carboxamide, (B65) 2-chloro-N-[4'-(3-methoxy-3-methylbut-l-yn-l- yl)biphenyl-2-yl] nicotinamide, (B66) l,3-dimethyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-l H- pyrazole-4-carboxamide, (B67) l,3-dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4- yl]-lH- pyrazole-4-carboxamide, (B68) l,3-dimethyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4- yl]-lH- pyrazole-4-carboxamide, (B69) 3-(difluoromethyl)-N-methoxy-l-methyl-N-[l-(2,4,6- trichlorophenyl)propan-2-yl]-lH-pyrazole-4-carboxamide, (B70) 3-(difluoromethyl)-N-(7-fluoro-l,l,3- trimethyl-2,3-dihydro-lH-inden-4-yl)-l-methyl-lH-pyrazole-4- carboxamide, (B71) 3-(difluoromethyl)- N-[(3,R)-7-fluoro-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl] -l-methyl-lH-pyrazole-4-carboxamide, (B72) 3-(difluoromethyl)-N-[(3S)-7-iluoro-l,l,3-trimethyl-2,3-dihy dro-lH-inden-4-yl]-l-methyl-lH- pyrazole-4-carboxamide.

C) Inhibitors of the respiratory chain at complex III, for example (C01) ametoctradin, (C02) amisulbrom,

(C03) azoxystrobin, (C04) cyazofamid, (C05) coumethoxystrobin, (C06) coumoxystrobin, (C07) dimoxystrobin, (CO 8) enoxastrobin, (C09) famoxadone, (CIO) fenamidone, (Cl l) fenaminstrobin, (C12) flufenoxystrobin, (C13) fluoxastrobin, (C14) kresoxim-methyl, (C15) metominostrobin, (C16) mandestrobin, (C17) orysastrobin, (C18) picoxystrobin, (C19) pyraclostrobin, (C20) pyrametostrobin, (C21) pyraoxystrobin, (C22) pyribencarb, (C23) triclop yricarb, (C24) trifloxystrobin, (C25) (2E)-2-(2- { [6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phe nyl)-2-(methoxyimino)-N- methylacetamide, (C26) (2E)-2-(methoxyimino)-N-methyl-2-(2-{ [({(lE)-l-[3-(trifluoromethyl)phenyl] ethybdene}amino)oxy] methyl }phenyl)acetamide, (C27) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({ 1- [3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}acetam ide, (C28) (2E)-2-{2-[({ [(lE)-l-(3-

{ [(E)-l-fluoro-2-phenylvinyl]oxy} phenyl)ethybdene] amino} oxy)methyl]phenyl} -2-(methoxyimino)-N- methylacetamide, (C29) Fenaminostrobin, (C30) 5-methoxy-2-methyl-4-(2-{ [({ (lE)-l-[3-

(trifluoromethyl)phenyl]ethybdene}amino)oxy]methyl}phenyl )-2,4-dihydro-3H- l,2,4-triazol-3-one, (C31) methyl (2E)-2- { 2- [( { cyclopropyl[(4-methoxyphenyl)imino] methyl } sulfanyl)methyl]phenyl } -3- methoxyacrylate, (C32) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxyb enzamide, (C33) 2- { 2- [(2,5 -dimethylphenoxy)methyl]phenyl } -2-methoxy-N-methylacetamide, (C34) 2- { 2-[(2,5- dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (C35) (2E,3Z)-5-{ [l-(4- chlorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dime thylpent-3-enamide.

D) Inhibitors of the mitosis and cell division, for example (D01) benomyl, (D02) carbendazim, (D03) chlorfenazole, (D04) diethofencarb, (D05) ethaboxam, (D06) fluopicobde, (D07) fiiberidazole, (D08) pencycuron, (D09) thiabendazole, (DIO) thiophanate- methyl, (Dl l) thiophanate, (D12) zoxamide, (D13)

5-chloro-7-(4-methylpiperidin-l-yl)-6-(2,4,6-trifluorophe nyl)[l,2,4]triazolo[l,5-a]pyrimidine, (D14) 3- chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6- trifluorophenyl) pyridazine, (D15) 3-chloro-4-(2,6- difluorophenyl)-6-methyl-5-phenyl-pyridazine , (D16) 3-chloro-6-methyl-5-phenyl-4-(2,4,6- trifluorophenyl)pyridazine, (D17) N-ethyl-2-[(3-thynyl-8-methyl-6-quinolyl)oxy]butanamide , (D18) N- ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfany l-acetamide , (D19) 2-[(3-ethynyl-

8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide, (D20) 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- N-(2-fluoroethyl)-2-methoxy-acetamide, (D21) 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl- butanamide, (D22) 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-ac etamide, (D23) 2-[(3- ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-a cetamide, (D24) 2-[(3-ethynyl-8-methyl-

6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetam ide, (D25) 4-(2-bromo-4-fluoro-phenyl)-N-(2- chloro-6-fluoro-phenyl)-2,5 -dimethyl -pyrazol-3 -amine, (D26) Aminopyrazole;

E) Compounds capable to have a multisite action, for example (E01) bordeaux mixture, (E02) captafol, (E03) captan, (E04) chlorothalonil, (E05) copper hydroxide, (E06) copper naphthenate, (E07) copper oxide, (E08) copper oxychloride, (E09) copper(2+) sulfate, (E10) dichlofluanid, (El l) dithianon, (E12) dodine, (E13) dodine free base, (E14) ferbam, (E15) fluorofolpet, (E16) folpet, (E17) guazatine, (E18) guazatine acetate, (E19) iminoctadine, (E20) iminoctadine albesilate, (E21) iminoctadine triacetate, (E22) mancopper, (E23) mancozeb, (E24) maneb, (E25) metiram, (E26) metiram zinc, (E27) oxine- copper, (E28) propamidine, (E29) propineb, (E30) sulfur and sulfur preparations including calcium polysulfide, (E31) thiram, (E32) tolylfluanid, (E33) zineb, (E34) ziram, (E35) anilazine, (E36) dipymetitrone.

F) Compounds capable to induce a host defence, for example (F01) acibenzolar-S -methyl, (F02) isotianil, (F03) probenazole, (F04) tiadinil, (F05) laminarin, (F06) 4-cyclopropyl-N-(2,4- dimethoxyphenyl)thiadiazole-5-carboxamide.

G) Inhibitors of the amino acid and/or protein biosynthesis, for example (G01) andoprim, (G02) blasticidin-S, (G03) cyprodinil, (G04) kasugamycin, (G05) kasugamycin hydrochloride hydrate, (G06) mepanipyrim, (G07) pyrimethanil, (G08) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l- yl)quinoline,(G09)oxytetracycline,(G10)streptomycin.

H) Inhibitors of the ATP production, for example (H01) fentin acetate, (H02) fentin chloride, (H03) fentinhydroxide, (H04) silthiofam.

I) Inhibitors of the cell wall synthesis, for example (101) benthiavalicarb, (102) dimethomorph, (103) flumorph, (104) iprovalicarb, (105) mandipropamid, (106) polyoxins, (107) polyoxorim, (108) validamycin A, (109) valifenalate, (110) polyoxin B, (Il l) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l- (morpholin-4-yl)prop-2-en-l-one, (P2) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l- (morpholin-4-yl)prop-2-en- 1 -one.

J) Inhibitors of the lipid and membrane synthesis, for example (J01) biphenyl, (J02) chloroneb, (J03) dicloran, (J04) edifenphos, (J05) etridiazole, (J06) iodocarb, (J07) iprobenfos, (J08) isoprothiolane, (J09) propamocarb, (J10) propamocarb hydrochloride, (Jl l) prothiocarb, (J12) pyrazophos, (J13) quintozene, (J14) tecnazene, (J15) toclof os-methyl.

K) Inhibitors of the melanin biosynthesis, for example (KOI) carpropamid, (K02) diclocymet, (K03) fenoxanil, (K04) phthalide, (K05) pyroquilon, (K06) tolprocarb, (K07)tricyclazole. Inhibitors of the nucleic acid synthesis, for example (L01) benalaxyl, (L02) benalaxyl-M (kiralaxyl),

L) (L03) bupirimate, (L04) clozylacon, (L05) dimethirimol, (L06) ethirimol, (L07) furalaxyl, (L08) hymexazol, (L09) metalaxyl, (L10) metalaxyl-M (mefenoxam), (LI 1) ofurace, (L12) oxadixyl, (L13) oxolinic acid, (L14)octhilinone.

M) Inhibitors of the signal transduction, for example (M01) chlozolinate, (M02) fenpiclonil, (M03) fludioxonil, (M04) iprodione, (M05) procymidone, (M06) quinoxyfen, (M07) vinclozolin, (M08) proquinazid.

N) Compounds capable to act as an uncoupler, for example (N01) binapacryl, (N02) dinocap, (N03) ferimzone, (N04) fluazinam, (N05) meptyldinocap.

O) Further compounds, for example (O01) benthiazole, (002) bethoxazin, (003) capsimycin, (004) carvone, (005) chinomethionat, (006) pyriofenone (chlazafenone), (007) cufraneb, (008) cyflufenamid, (009) cymoxanil, (OIO) cyprosulfamide, (Oi l) dazomet, (012) debacarb, (013) dichlorophen, (014) dichlobentiazox, (015) diclomezine, (016) difenzoquat, (017) difenzoquat metilsulfate, (018) diphenylamine, (019) ecomate, (020) fenpyrazamine, (021) fenhexamine, (022) flumetover, (023) fluoroimide, (024) flusulfamide, (025) flutianil, (026) fosetyl-aluminium, (027) fosetyl-calcium, (028) fosetyl-sodium, (029) hexachlorobenzene, (030) irumamycin, (031) isothianil, (032) methasulfocarb, (033) methyl isothiocyanate, (034) metrafenone, (035) mildiomycin, (036) natamycin, (037) nickel dimethyldithiocarbamate, (038) nitrothal-isopropyl, (039) oxamocarb, (040) oxyfenthiin, (041) pentachlorophenol and salts, (042) phenothrin, (043) picarbutrazox (044) phosphorous acid and its salts, (045) propamocarb-fosetylate, (046) propanosine-sodium, (047) pyrimorph, (048) pyraziflumid (049) pyrrolnitrine, (050) tebufloquin, (051) tecloftalam, (052) tolnifanide, (053) triazoxide, (054) trichlamide, (055) zarilamid, (056) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4- methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-l,5-d ioxonan-7-yl 2-methylpropanoate, (057) 1 -(4- { 4-[(5R)-5 -(2,6-difluorophenyl)-4,5 -dihydro- 1 ,2-oxazol-3 -yl] - 1 ,3 -thiazol-2-yl } piperidin- 1 -yl)-2- [5 - methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (058) l-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5- dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2- [5-methyl-3-(trifluoromethyl)-lH-pyrazol-l- yl]ethanone, (059) dichlobentiazox, (060) l-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl-lH-imidazole- 1-carboxylate, (061) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, (062) 2,3-dibutyl-6- chlorothieno[2,3-d]pyrimidin-4(3H)-one, (063) 2,6-dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrole- l,3,5,7(2H,6H)-tetrone, (064) 2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]-l-(4-{4-[(5 R)-5-phenyl-

4.5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l -yl)ethanone, (065) 2-[5-methyl-3-

(trifluoromethyl)- IH-pyrazol- 1 -yl] - 1 -(4- { 4-[(5 S)-5 -phenyl-4,5 -dihydro- 1 ,2-oxazol-3-yl] - 1 ,3 -thiazol-2- yl Jpiperidin- 1 -yl)ethanone, (066) 2- [5 -methyl-3 -(trifhioromethyl)- lH-pyrazol-]-yl] - 1 - { 4-[4-(5 -phenyl -

4.5-dihydro-l,2-oxazol-3-yl)-l,3- thiazol-2-yl]piperidin-l-yl}ethanone, (067) 2-butoxy-6-iodo-3-propyl-

4H-chromen-4-one, (068) 2-chloro-5- [2-chloro-l -(2,6-difluoro-4-methoxyphenyl)-4-methyl- 1H- imidazol-5-yl]pyridine, (069) 2-phenylphenol and salts, (070) 3-(4,4,5- triflu oro-3, 3 -dimethyl-3, 4- dihydroisoquinolin-l-yl)quinoline, (071) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (072) 3-chloro-5-(4- chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (073) 4-(4-chlorophenyl)-5-(2,6- difluorophenyl)-3,6-dimethylpyridazine, (074) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5- phenylpyridazine, (075) 5-amino-l,3,4-thiadiazole-2-thiol, (076) 5-chloro-N‘-phenyl-N'-(prop-2-yn-l- yl)thiophene-2-sulfonohydrazide, (077) 5-fluoro-2-[(4-lluorobenzyl)oxy]pyrimidin-4-amine, (078) 5- fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (079) 5-methyl-6-octyl[l,2,4]triazolo[l,5- a]pyrimidin-7-amine, (080) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (081) N'-(4-{ [3-(4- chlorobenzyl)-l,2,4-thiadiazol-5-yl]oxy} -2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (082) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-l-yloxy)phenyl] propanamide, (083) N-[(4- chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-l-ylox y)phenyl]propanamide, (084) N-[(5- bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide, (085) N-[l-(5-bromo-3-chloropyridin-2- yl)ethyl]-2,4-dichloronicotinamide, (086) N-[l-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4- iodonicotinamide, (087) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3- difluorophenyl] methyl } -2-phenylacetamide, (088) N- { (Z)-[(cyclopropylmethoxy)imino] [6-

(difluoromethoxy)-2,3-difluorophenyl] methyl} -2-phenylacetamide, (089) N'-{4-[(3-tert-butyl-4-cyano- l,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-met hylimidoformamide, (090) N-methyl-2- (1 - { [5 -methyl-3 -(trifhioromethyl)- IH-pyrazol- 1 -yl] acetyl } piperidin-4-yl)-N-( 1 ,2,3 ,4- tetrahydronaphthalen-l-yl)-l,3-thiazole-4-carboxamide, (091) N-methyl-2-(l-{ [5-methyl-3-

(trifluoromethyl)- IH-pyr azol-1 -yl] acetyl }piperidin-4-yl)-N-[(lR)- 1,2, 3, 4-tetrahydronaphthalen-l-yl]- 1,3- thiazole-4-carboxamide, (092) N-methyl-2-(l-{ [5-methyl-3-(trifluoromethyl)-lH-pyrazol-l- yl]acetyl]piperidin-4-yl)-N-[(lS)-l,2,3,4- tetrahydronaphthalen-l-yl]-l,3-thiazole-4-carboxamide, (093) pentyl {6-[({ [(l-methyl-lH-tetrazol-5-yl)(phenyl)methylene]amino}oxy)meth yl]pyridin-2-yl} carbamate, (094) phenazine-1 -carboxylic acid, (095) quinolin-8-ol, (096) quinolin-8-ol sulfate (2:1), (097) tert- butyl { 6-[({ [(l-methyl-lH-tetrazol-5-yl)(phenyl) methylene]amino}oxy)methyl]pyridin-2-yl} carbamate, (098) (5 -bromo-2-methoxy-4-methylpyridin-3 -yl)(2,3 ,4-trimethoxy-6-methylphenyl) methanone, (099) N-[2-(4-{ [3-(4-chlorophenyl)prop-2-yn-l-yl]oxy}-3-methoxyphenyl)thyl] -N2-

(methylsulfonyl)valinamide, (OIOO) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (O101) but-3-yn-l-yl { 6-[({ [(Z)-(l-methyl-lH-tetrazol-5-yl)(phenyl)methylene]amino}oxy) methyl]pyridin-2-yl} carbamate,

(0102) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(lH)-one), (0103) propyl 3,4,5-trihydroxybenzoate, (0104) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)- l,2-oxazol-4-yl](pyridin-3-yl)methanol, (0105) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)- l,2-oxazol-4-yl](pyridin-3-yl)methanol, (0106) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)- l,2-oxazol-4-yl](pyridin-3-yl)methanol, (0107) 2-fluoro-6-(trifluoromethyl)-N-(l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl)benzamide, (0108) 2-(6-benzylpyridin-2-yl)quinazoline, (0109) 2-[6-(3-fluoro-4- methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (0110) 3-(4,4-difluoro-3,3-dimethyl-3,4- dihydroisoquinolin-l-yl)quinoline, (0111) Abscisic acid, (0112) N'-[5-bromo-6-(2,3-dihydro-lH-inden- 2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamid e, (0113) N'-{5-bromo-6-[l-(3,5- difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methy limidoformamide, (0114) N'-{5-bromo- 6-[(lR)-l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}- N-ethyl-N-methylimidoformamide, (0115) N'-{5-bromo-6-[(lS)-l-(3,5-difluorophenyl)ethoxy]-2-methylpy ridin-3-yl}-N-ethyl-N- methylimidoformamide, (0116) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy] -2-methylpyridin-3- yl}-N-ethyl-N-methylimidoformamide, (0117) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2- methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (0118) N-cyclopropyl-3-(difluoromethyl)-5- fluoro-N-(2-isopropylbenzyl)-l -methyl- lH-pyrazole-4-carboxamide, (0119) N-cyclopropyl-N-(2- cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH-p yrazole-4-carboxamide, (0120) N-(2-tert- butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-met hyl-lH-pyrazole-4-carboxamide, (0121) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)- 5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (0122) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluorometh yl)-5-fluoro-l- methyl-lH-pyrazole-4-carboxamide, (0123) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5- fluorobenzyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (0124) N-cyclopropyl-3-(difluoromethyl)- 5-fluoro-N-(5-fluoro-2-isopropylbenzyl)- 1 -methyl- lH-pyrazole-4-carboxamide, (0125) N-cyclopropyl- N-(2-cyclopropyl-5 -fluorobenzyl)-3-(difluoromethyl)-5 -fluoro- 1 -methyl- 1 H-pyrazole-4-carboxamide, (0126) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropy-3-(difluoromet hyl)-5-fluoro-l-methyl-lH- pyrazole-4-carboxamide, (0127) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6- isopropylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (0128) N-cyclopropyl-3-(difluoromethyl)-N-(2- ethyl-5-methylbenzyl)-5-fluoro-l -methyl- lH-pyrazole-4-carboxamide, (0129) N-cyclopropyl-3-

(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)- l-methyl-lH-pyrazole-4-carboxamide, (0130) N-cycIopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluorome thyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (0131) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromet hyl)-5-fluoro-l- methyl- lH-pyrazole-4-carboxamide, (0132) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3- (difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide , (0133) N-cyclopropyl-3-

(difluoromethyl)-5-fluoro- 1 -methyl-N- [5 -methyl-2-(trifluoromethyl)benzyl] - 1 H-pyrazole-4-carboxamide, (0134) N-[2-chloro-6-(trifhioromethyl)benzyl]-N-cyclopropyl-3-(difh ioromethyl)-5-fluoro-l-methyl-lH- pyrazole-4-carboxamide, (0135) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropy l-3- (difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide , (0136) N-cyclopropyl-3-

(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro- 1 -methyl- lH-pyrazole-4-carboxamide, (0137) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenz yl)-l-methyl-lH-pyrazole-4- carbothioamide, (0138) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoforma mide, (0139) N'-{4-[(4,5-dichloro-l,3-thiazol-2-yl)oxy]-2,5-dimethylpheny l}-N-ethyl-N-methylimidoformamide, (0140) N-(4-chloro-2,6-difhiorophenyl)-4-(2-chloro-4-fhiorophenyl)- l,3-dimethyl-lH-pyrazol-5-amine, (0141) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-l,4-benz oxazepine, (0142) 2-{2-fluoro-6- [(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (0143) 2-{2-[(7,8-difluoro-2-methylquinolin- 3-yl)oxy]-6-fluorophenyl}propan-2-ol, (0144) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)- 1,3- dimethyl- lH-pyrazol-5 -amine, (0145) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-l,3-dimet hyl- lH-pyrazol-5 -amine, (0146) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-iluorophenyl)-l,3- dimethyl-lH- pyrazol-5-amine, (0147) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-iluorophenyl)-l,3-d imethyl-lH- pyrazol-5-amine, (0148) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-l,3-d imethyl-lH- pyrazol-5-amine, (0149) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)- 1,3-dimethyl- lH-pyrazol-5- amine, (0150) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-l, 3-dimethyl- lH-pyrazol-5- amine, (0151) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-l ,3-dimethyl-lH-pyrazol-5-amine, (0152) N -(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)- 1 ,3 -dimethyl- 1 H-pyrazol-5 -amine, (0153) 4-(2- chloro-4-fluorophenyl)-N-(2-chlorophenyl)-l,3-dimethyl-lH-py razol-5-amine, (0154) 4-(2-bromo-4- fluorophenyl)-N-(2,6-difluorophenyl)-l,3-dimethyl-lH-pyrazol -5-amine, (0155) 4-(2-bromo-4- fluorophenyl)-N-(2-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-a mine, (0156) N'-(4-{ 3-

[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N- ethyl-N-methylimidoformamide, (0157) N’- (2,5 -dimethyl-4- { 3- [( 1 , 1 ,2,2-tetrafluoroethyl)sulfanyl]phenoxy } phenyl)-N -ethyl-N - methylimidoformamide, (0158) N‘-(2,5-dimethyl-4-{ 3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)- N-ethyl-N-methylimidoformamide, (0159) N‘-(2,5-dimethyl-4-{3-[(2,2,3,3- tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyli midoformamide, (0160) N'-(2,5- dimethyl-4- { 3 - [(pentafluoroethyl)sulfanyl]phenoxy } phenyl)-N -ethyl -N-methylimidoformamide, (0161) N'-(4-{ [3-(dilluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-e thyl-N-methylimidoformamide, (0162) N'-(2,5-dimethyl-4-{ [3-(l,l,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethy l-N- methylimidoformamide, (0163) N'-(2,5-dimethyl-4-{ [3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)- N-ethyl-N-methylimidoformamide, (0164) N'-(2,5-dimethyl-4-{ [3-(2,2,3,3- tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methyli midoformamide, (0165) N'-(2,5- dimethyl-4-{ [3-(pentalluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-meth ylimidofomiamide, (0166) 2- [3 ,5 -bis(difluoromethyl)- IH-pyrazol- 1 -yl]- 1 - [4-(4- { 5 - [2-(prop-2-yn- 1 -yloxy)phenyl] -4,5-dihydro- 1,2- oxazol-3 -yl } - 1 ,3-thiazol-2-yl)piperidin- 1 -yl] ethanone, (0167) 2- [3 ,5 -bis(difluoromethyl)- IH-pyrazol- 1 - yl]- 1 - [4-(4- { 5 - [2-fluoro-6-(prop-2-yn- 1 -yloxy)phenyl] -4,5 -dihydro- 1 ,2-oxazol-3 -yl } - 1 ,3 -thiazol-2- yl)piperidin-l-yl] ethanone, (0168) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-ch loro-6- (prop-2-yn- l-yloxy)phenyl]-4, 5-dihydro- 1 ,2-oxazol-3-yl } - 1 ,3-thiazol-2-yl)piperidin-l -yl] ethanone, (0169) 2-{3-[2-(l-{ [3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4- yl)-l,3-thiazol-4-yl]-

4,5-dihydro-l,2-oxazol-5-yl]phenyl methanesulfonate, (0170) 2-{3-[2-(l-{ [3,5-bis(difluoromethyl)-lH- pyr azol-1 -yl] acetyl }piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5- yl]-3-chlorophenyl methanesulfonate, (0171) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{ (5S)-5-[2-(prop-2-yn-l- yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl) piperidin-l-yl]ethanone, (0172) 2-[3,5- bis(difluoromethyl)- 1 H-pyrazol- 1 -yl] - 1 -[4-(4- { (5R)-5- [2-(prop-2-yn- 1 -yloxy)phenyl] -4,5-dihydro- 1,2- oxazo 1 -3-yl } - 1 ,3 -thiazol-2-yl)piperidin- 1 -yl] ethanone, (0173) 2- [3 ,5 -bis(difluoromethyl)- IH-pyrazol- 1 - yl]- 1 - [4-(4- { (5S)-5 - [2-flu oro-6-(prop-2-yn- 1 -yloxy)phenyl]-4,5-dihydro- 1 ,2-oxazol-3 -yl } - 1 ,3 -thiazol-2- yl)piperidin-l-yl] ethanone, (0174) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{ (5R)-5-[2- fluoro-6-(prop-2-yn- 1 -yloxy)phenyl] -4,5 -dihydro- 1 ,2-oxazol-3 -yl } - 1 ,3 -thiazol-2-yl)piperidin- 1 - yl]ethanone, (0175) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{(5S)-5- [2-chloro-6-(prop-2-yn-

1-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol- 2-yl)piperidin-l-yl]ethanone, (0176) 2-[3,5- bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{ (5R)-5-[2-chloro-6-(prop-2-yn-l-yloxy)phenyl]-4,5- dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl)piperidin-l-yl]eth anone, (0177) 2-{(5S)-3-[2-(l-{ [3,5- bis(difluoro methyl)- 1 H-pyrazol- 1 -yl] acetyl } piperidin-4-yl)- 1 ,3-thiazol-4-yl] -4,5 -dihydro- 1 ,2-oxazol-5- yljphenyl methanesulfonate, (0178) 2-{(5R)-3-[2-(l-{ [3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]acetyl]piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2- oxazol-5-yl {phenyl methanesulfonate, (0179)

2-{(5S)-3-[2-(l-{ [3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4- yl)-l,3-thiazol-4-yl]-4,5- dihydro-l,2-oxazol-5-yl]-3-chlorophenyl methanesulfonate, (0180) 2-{(5R)-3-[2-(l-{ [3,5- bis(difluoro methyl)- 1 H-pyrazol- 1 -yl] acetyl } piperidin-4-yl)- 1 ,3-thiazol-4-yl] -4,5 -dihydro- 1 ,2-oxazol-5- yl]-3-chlorophenyl methanesulfonate, (0181) (3S,6S,7R,8R)-8-benzyl-3-{3-[(isobutyryloxy)methoxy]-4- methoxypicolinamido] -6-methyl-4,9-dioxo-l, 5-diox onan-7-yl isobutyrate, (0182) N'-(4-(4-chloro-3- trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-meth yl formamidine, (0183) N'-(4-(4-fluoro-

3-trifhioromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N -methylformamidine, (0184)N'-[4-[[3-[(4- chi orophenyl)methyl]-l, 2, 4-thiadiazol-5-yl]oxy]-2, 5 -dimethyl -phenyl]-N-ethyl-N-methyl-formamidine, (0185) N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-me thyl-formamidine, (0186) N'-[5- bromo-6-[l-(3,5-difluorophenyl)ethoxy]-2 methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine, (0187) N'- [5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-et hyl-N-methyl-formamidine, (0188) N'- [5-bromo-2-methyl-6-(l-phenylethoxy)-3-pyridyl]-N-ethyl-N-me thylformamidine, (0189) N'-(2-methyl- 5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)phenyl)-N-et hyl-N-methyl formamidine, (0190) N'-(5- difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-pheny l)-N-ethyl-N-methyl formamidine,

(0191), (N-ethyl-N'-(4-(2-fluorophenoxy)-2,5-dimethylphenyl)-N-methy lformimidamide, (0192) N'-(2- chloro-4-(2-fluorophenoxy)-5-methylphenyl)-N-ethyl-N-methylf ormimidamide, (0193) 2-[2-[(7,8- difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-o l, (0194) 2-[2-fluoro-6-[(8-fluoro-2- methyl-3-quinolyl)oxy]-phen-yl]propan-2-ol, (0195) quinofumelin, (0196) 9-fluoro-2,2-dimethyl- 5-(3-quinolyl)-3H-l,4-benzoxazepine, (0197) 2-(6-benzyl-2-pyridyl)quinazoline, (0198) 2-[6-(3- fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline, (0199) Fluopimomide, (0200) florylpicoxamid, (0201) fluoxapiprolin.

P) Growth regulators, for example abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri- iodobenzoic acid , trinexapacethyl and uniconazole.

The active substances referred above, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141317, EP-A 152031, EP-A 226917, EP-A 243 970, EP-A 256503, EP-A 428941, EP-A 532022, EP-A 1028125, EP-A1035122, EP-A 1201648, EP-A 1122244, JP 2002316902, DE 19650197, DE 10021412, DE 102005009458, US 3,296,272, US 3,325,503, WO 98/46608, WO 99/14187, WO 99/24413, WO 99/27783, WO 00/29404, WO 00/46148, WO 00/65913, WO 01/54501, WO 01/56358, WO 02/22583, WO 02/40431, WO 03/10149, WO 03/11853, WO 03/14103, WO 03/16286, WO 03/53145, WO 03/61388, WO 03/66609, WO 03/74491, WO 04/49804, WO 04/83193, WO 05/120234, WO 05/123689, WO 05/123690, WO 05/63721, WO 05/87772, WO 05/87773, WO 06/15866, WO 06/87325, WO 06/87343, WO 07/82098, WO 07 /90624, WO 10/139271, WO 11 /028657, WO 12/168188, WO 07 /006670, WO 11/77514, WO 13/047749, WO 10/069882, WO 13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441, WO 13/162072, WO 13/092224, WO 11/135833, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/116251, WO 08/013622, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511, WO 11/081174, WO 13/47441).

As described above the compound of formula (I) can be mixed with one or more active compatible compounds selected from the insecticides/acaricides/nematicides class, which are specified herein by their common names that are known and described, for example in The Pesticide Manual 17th Ed. , or can be searched in the internet (e.g. under www.alanwood.net/pesticides ).

(1) Acetylcholinesterase (AChE) inhibitors such as carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb or organophosphates, such as acephate, azamethiphos, azinphos- ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S- methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion- methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel antagonists, such as cyclodiene organochlorines, for example chlordane and endosulfan or phenylpyrazoles (fiproles), for example ethiprole and fipronil.

(3) Sodium channel modulators/voltage-dependent sodium channel blockers, such as pyrethroids, for example acrinathrin, allethrin, d -cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta- cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin [( I R p/rans-isomers], deltamethrin, empenthrin [(EZ)- (lR)-isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau- fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R )-trans- isomer), prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(lR)-isomers)], tralomethrin and transfluthrin or DDT or methoxychlor. (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, such as neonicotinoids, for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.

(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosyns, for example spinetoram and spinosad.

(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins / milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone mimics such as juvenile hormone analogues, for example hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Active compounds with unknown or non-specific mechanisms of action, such as alkyl halides for example as methyl bromide and other alkyl halides or chloropicrin or fluorides or borates or tartar emetic or methyl isocyanate generators.

(9) Chordotonal organ TRPV channel modulators such as pyridine azomethine derivatives, for example pymetrozine and pyrifluquinazon or flonicamid.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox and diflovidazin or etoxazole.

(11) Microbial disruptors of insect gut midgut, for example Bacillus thuringiensis subspecies israelensis, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and Bacillus sphaericus and BT crop proteins: CrylAb, CrylAc, CrylFa, CrylA 105, Cry2Ab, Vip3a, mCry3A, Cry3Ab, Cry3Bb, Cry34Abl / Cry35Abl.

(12) Inhibitors of mitochondrial ATP synthase such as organotin miticides, for example azocyclotin, cyhexatin and fenbutatin oxide or diafenthiuron or propargite or tetradifon.

(13) Uncouplers of oxidative phosphorylation acting via disruption of the proton gradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinic acetylcholine receptor (nAChR) channel blockers, such as bensultap, cartap- hydrochloride, thiocyclam and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, such as bistrifluoron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, such as buprofezin.

(17) Molting disruptors (particularly in Dipteran), such as cyromazine.

(18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists, such as amitraz. (20) Mitochondrial complex III electron transport inhibitors such as hydramethylnon or acequinocyl or fluacrypyrim or bifenazate.

(21) Mitochondrial complex I electron transport inhibitors, for example, METI acaricides and insecticides, for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers such as indoxacarb or metaflumizone.

(23) Inhibitors of acetyl CoA carboxylase, such as tetronic and tetramic acid derivatives, for example spirodiclofen, spiromesifen and spirotetramat.

(24) Mitochondrial complex IV electron transport inhibitors, such as phosphides, for example aluminum phosphide, calcium phosphide, zinc phosphide and phosphine or cyanides.

(25) Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, for example cyenopyrafen and cyflumetofen or carboxanilides.

(26) Ryanodine receptor modulators such as diamides, for example chlorantraniliprole, cyantraniliprole, flubendiamide, tetraniliprole, (R)-3-chloro-N-l-{2-methyl-4-[l,2,2,2-tetrafluoro-l-

(trifluoromethyl)ethyl]phenyl}-N2-(l -methyl -2-methylsulfonylethyl)phthalamide, (S)-3-chloro-Nl-{2- methyl-4- [ 1 ,2,2,2-tetrafluoro- 1 -(trifluoromethyl)ethyl]phenyl } -N2-( 1 -methyl-2- methylsulfonylethyl)phthalamide, methyl-2- [3 ,5 -dibromo-2-({ [3-bromo-l-(3-chloropyridin-2-yl)-lH- pyrazol-5-yl]carbonyl}amino)benzoyl]-l,2-dimethylhydrazineca rboxylate, N-[4,6-dichloro-2-[(diethyl- lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyri dyl)-5-(trifluoromethyl)pyrazole-3- carboxamide, N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6- methyl-phenyl]-2-(3-chloro- 2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-2-[(di-2-propyl-lambda-4- sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3 -chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide, N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-su lfanylidene)carbamoyl]phenyl]-2-(3-chloro-2- pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, N-[4,6-dibromo-2-[(diethyl-lambda-4- sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(t rifluoromethyl)pyrazole-3-carboxamide, N- [2-(5-amino-l,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]- 3-bromo-l-(3-chloro-2-pyrid inyl)-lH- pyrazole-5-carboxamide;3-chloro-l-(3-chloro-2-pyridinyl)-N-[ 2,4-dichloro-6-[[(l-cyano-l- methylethyl)amino]carbonyl]phenyl]-lH-pyrazole-5-carboxamide , 3-bromo-N-[2,4-dich loro-6- (methylcarbamoyl)phenyl] - 1 -(3 ,5 -dichloro-2 -pyridyl)- 1 H-pyrazole-5 -carboxamide, N - [4-chloro-2- [[(1,1- dimethylethyl)amino]carbonyl]-6-methylphenyl]-l-(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-l H- pyrazole-5-carboxamide and cyhalodiamide.

(27) Chordotonal organ modulators on undefined target site such as flonicamid.

Further active ingredients with unknown or indeterminate mode of action, such as afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol, diflovidazin, llometoquin, lluazaindolizine, fluensulfone, llufenerim, llufenoxystrobin, llufiprole, lluhexafon, fluopyram, lluralaner, lluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, lotilaner, meperfluthrin, paichongding, pyflubumide, pyridalyl, pyrilluquinazon, pyriminostrobin, sarolaner, tetramethylfluthrin, tetrachlorantraniliprole, tioxazafen, trillumezopyrim and iodomethane; furthermore, preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following known active compounds: l-{2-fluoro-4-methyl-5-[(2,2,2-trifhioroethyl)sulfmyl]phenyl }-3- (trifluoromethyl)-lH-l,2,4-triazol-5-amine (known from W02006043635), { l'-[(2E)-3-(4- chlorophenyl)prop-2-ene-l-yl]-5-fhiorospiro[indole-3,4'-pipe ridine]-l(2H)-yl}(2-chloropyridin-4- yl)methanone (known from W02003106457), 2-chloro-N-[2-{ l-[(2E)-3-(4-chlorophenyl)prop-2-en-l- yl]piperidin-4-yl} -4-(trifhioromethyl)phenyl]isonicotinamide (known from W02006003494), 3-(2,5- dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3 -en-2-one (known from

W02009049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l,8-diazaspiro[4.5]de c-3-en-4-yl ethyl carbonate (known from W02009049851), 4-(but-2-in-l-yloxy)-6-(3,5-dimethylpiperidin-l-yl)-5- fluoropyrimidine (known from W02004099160), 4-(but-2-in-l-yloxy)-6-(3 -chi orophenyl)pyrimi dine (known from W02003076415), PF1364 (CAS-Reg.No. 1204776-60-2), [methyl-2-[2-({ [3-bromo-l-(3- chloropyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)-5-chloro -3-methylbenzoyl]-2- methylhydrazincarboxylate, methyl -2-[2-({ [3-bromo- 1 -(3-chloropyridin-2-yl)- lH-pyrazol-5- yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinc arboxylate, methyl-2-[2-({ [3-bromo-l- (3 -chi or o-pyridin-2 -y 1) - 1 H-pyr azol-5 -y 1] carbonyl } amino)-5 -cyano-3 -methylbenzoy 1] -2- methylhydrazincarboxylate and methyl-2-[3,5-dibromo-2-({ [3-bromo-l-(3-chloro-pyridin-2-yl)-lH- pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazincarboxyl ate (known from W02005085216)], N- [2-(5-amino-l,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]- 3-bromo-l-(3-chloropyridin-2-yl)-lH- pyrazole-5-carboxamide (known from CN102057925), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydro-l,2-oxazol-3-yl]-2-methyl-N-(l-oxidothietan-3-yl)ben zamide (known from W02009080250), N- [(2E)-l-[(6-chloropyridine-3-yl)methyl]pyridin-2(lH)-ylidene ]-2,2,2-trifluoroacetamide (known from WO2012029672), l-[(2-chloro-l,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyri do[l,2-a]pyrimidin-l- ium-2-olate (known from W02009099929), l-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H- pyrido[l,2-a]pyrimidin-l-ium-2-olate (known from W02009099929), 4-(3-{2,6-dichloro-4-[(3,3- dichloroprop-2-en-l-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(tri fhioromethyl)pyrimidine (known from CN101337940), N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-l-(3-chl oropyridin-2-yl)-3-

(fluoromethoxy)-lH-pyrazole-5-carboxamide (known from WO2008134969), butyl-[2-(2,4- dichlorophenyl)-3-oxo-4-oxaspiro[4.5]dec-l-en-l-yl]carbonate (disclosed in CN102060818), 3(E)-3-[l- [(6-chloro-3 -pyridyl) methyl] -2-pyridyliden] -1,1,1 -trifluoropropan-2-one (known from W 02013144213), N-(methylsulfonyl)-6-[2-(pyridin-3-yl)-l ,3-thiazol-5-yl]pyridine-2-carboxamide (known from W02012000896), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-l-methyl-3-(pentafluo roethyl)-4-

(trifluoromethyl)-lH-pyrazole-5-carboxamide (known from W02010051926).

Other active compounds of unknown or uncertain mode of action: l l-(4-chloro-2,6-dimethylphenyl)-12- hydroxy-l,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-l l-en-10-one, 3-(4' -fluoro-2,4-dimethylbiphenyl-3-yl)- 4-hydroxy-8-oxa-l-azaspbo[4.5]dec-3-en-2-one, l-[2-fluoro-4-methyl-5 -[(2,2,2- trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-l H-l,2,4-triazole-5-amine, Bacillus firmus;(E/Z)-N- [l-[ (6-ch loro-3 -pyridyl) methyl] -2-pyridybdene ]-2,2,2-trifluoro-acetamide; (E/Z)-N-[l-[(6-chloro-5- fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-ace tamide; (E/Z)-2,2,2-trifluoro-N-[l-[(6-fluoro- 3-pyridyl)methyl]-2-pyridybdene]acetamide; (E/Z)-N-[l-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]- 2,2,2-trifluoroacetamide; (£ Z)-N- [ 1 - [ 1 -(6-chloro-3 -pyridyl)ethyl]-2-pyridylidene] -2,2,2- trifluoroacetamide; (E/Z)-N- [ 1 - [(6-chloro-3 -pyridyl)methyl] -2-pyridylidene] -2, 2-difluoro- acetamide;

(£/Z)-2-chloro-N-[ l-[ ( 6-chloro-3 -pyridyl) methyl]-2-pyridylidene]-2,2-difluoro-acetamide; (E/Z)-N-[l- [(2-chloropyrimidin-5-yl)methyl]-2-pyridybdene]-2,2,2-triflu oro-acetamide; (E/Z)-N-[l-[(6-chloro-3- pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propan amide); N-[l-[ (6-chloro-3-pyridyl)methyl]- 2-pyridybdene]-2,2,2-trifluoro-thioacetamide; N-[l-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene] -2,2,2- trifluoro-N' -isoprop yl-acetamidine; fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H- isoxazol-3-yl]-2-methyl-N-(l-oxothietan-3-yl)benzamide; fluxametamide; 5-[3-[2,6-dichloro-4-(3,3- dichloroallyloxy)phenoxy]propoxy]-lH-pyrazole; 3-(benzoylmethylamino)-N-[2-bromo-4-[l,2,2,3,3,3- hexafluoro-l-(trifluoromethyl)propyl]-6-(trifluoromethyl)phe nyl]-2-fluoro-benzamide; 3-

(benzoylmethylamino)-2-fluoro-N- [2-iodo-4-[l,2,2,2-tetrailuoro-l-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; N-[3-[[[2-iodo-4-[l,2,2,2-tetrafluoro-l-(trifluoromethyl)eth yl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benz amide; N-[3-[[[2-bromo-4-[l,2,2,2- tetrafluoro- 1 -(trifluoromethyl)ethyl] -6-(trifluoromethyl)phenyl] amino]carbonyl]-2-llLiorophenyl]-4- fluoro-N-methylbenzamide; 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[l,2,2,2-tetrafluoro-l-

(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]c arbonyl]phenyl]-N-methyl-benzamide; 3- fluoroN-[2-fluoro-3-[[[2-iodo-4-[l,2,2,2-tetrafluoro-l-(trif luoromethyl)ethyl]-

6(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl- benzamide; 2-chloro-N-[3-[[[2-iodo-4- [l,2,2,2-tetrafluoro-l-(trifluoromethyl)ethyl]-6-(trifluorom ethyl)phenyl]amino]carbonyl]phenyl]-3- pyridinecarboxamide; 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[l,2,2,3,3,3-hexafluoro -l-(triiluoromethyl) propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;4-cyano-3 -[(4-cyano-2-methyl-benzoyl)amino]- N-[2,6-dichloro-4-[l,2,2,3,3,3-hexafluoro-l-(trifluoromethyl ) propyl]phenyl]-2-fluoro-benzamide; N-[5- [[2-chloro-6-cyano-4-[l,2,2,3,3,3-hexafluoro-l-(trifluoromet hyl)propyl]phenyl]carbamoyl]-2-cyano- phenyl]-4-cyano-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[2,2,2-triiluoro-l-hydroxy-l- (trifluoromethyl)ethyl]phenyl] carbamoyl] -2-cyano-phenyl] -4-cyano-2-methyl-benzamide;N-[5 -[ [2- bromo-6-chloro-4-[l,2,2,3,3,3-hexafluoro-l-(trifluoromethyl) propyl]phenyl]carbamoyl]-2-cyano- phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[l,2,2,3,3,3-hexafluor o-l- (trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-be nzamide; 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4- [ 1 ,2,2,2-tetrafluoro- 1 -(trifluoromethyl)ethyl] phenyl]carbamoyl] phenyl] -2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[ 1, 2, 2, 2-tetraf uoro-l -(triflu oromethyl)ethyl] phenyl]carbamoyl]-2-cyan o- phenyl]-4-cya no-2-methyl-benzamide; 2-(l,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine ; 2-[6- [2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl] -pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2- pyridinyl] -pyrimidine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2 -carboxamide; N- methylsLilfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carb oxamide; N-ethyl-N-[4-methyl-2-(3- pyridyl)thiazol-5-yl]-3-methylthio-propan amide; N-methyl-N-[ 4-methyl-2-( 3-pyridyl)thiazol-5-yl]-3- methylthio-propanamide; N,N-2-dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3- methylthiopropanamide; N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-me thylthio- propanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-me thylthio-propanamide; N-[ 4- chloro-2-(3-pyridyl )thiazol-5-yl]-N ,2-dimethyl-3-methylthio-propanamide; N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N- ethyl-3-methylthio-propanamide; l-[(6-chloro-3-pyridinyl)methyl]-l,2,3,5,6,7-hexahydro-5-met hoxy-7- methyl-8-nitro-imidazo[l,2-a]pyridine; l-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-l,2,3,5,6, 7- hexahydroimidazo[l,2-a]pyridin-5-ol; l-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; l-(l,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyr azole-4-carboxamide; N,N- 5-dimethyl-N-pyridazin-4-yl-l-(2,2,2-trifluoro-l-methyl-ethy l)pyrazole-4-carboxamide; 1-[1-(1- cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-py razole-4-carboxamide; N-ethyl-l-(2- fluoro-1 -methyl-prop yl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; l-(l,2-dimethylpropyl)- N,5 -dimethyl-N -pyridazin-4-yl-pyrazole-4-carboxamide; 1 - [ 1 -( 1 -cyanocyclopropyl)ethyl] -N,5-dimethyl- N-pyridazin-4-yl-pyrazole-4-carboxamide; N-methyl-l-(2-lluoro-l-methyl-propyl]-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; l-(4,4-dilluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl - pyrazole-4-carboxamide; l-(4,4-dilluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyr azole-4- carboxamide; N-( l-methylethyl)-2-(3-pyridinyl)-2 H-indazole-4-carboxamide; N-cyclopropyl-2-(3- pyridinyl)-2H-indazole-4-carboxamide; N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; 2-(3- pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamid e; 2-(3-pyridinyl)-N-[(tetrahydro-2- furanyl)methyl]-2H-indazole-5-carboxamide; methyl 2-[[2-(3-pyridinyl)-2H-indazol-5- yl]carbonyl]hydrazinecarboxylate; N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indaz ole-5- carboxamide; N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxa mide; 2-(3-pyridinyl)N-(2- pyrimidinylmethyl )-2H-indazole-5 -carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]-2-( 3-pyridinyl)-2H- indazole-5 -carboxamide, N-[3-chloro-l-(3-pyridyl) pyrazol-4-yl]N-ethyl-3-(3, 3 ,3- trifluoropropylsulfanyl) propanamide; N-[3-ch loro-l-( 3-pyridyl) pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfinyl)propanamide; N-[3-chloro-l-(3-pyridyl)pyrazol-4-yl]-3-[(2,2- difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; N-[3-chloro-l-(3-pyridyl)pyrazol-4-yl]-3- [(2,2-dif uorocyclopropyl) methylsulfinyl]-N-ethyl-propanamide; sarolaner, lotilaner, isocycloseram, dimpropyridaz.

The mass ratio of any two ingredients in each combination is selected as to give the desired effect. In general, the mass ratio would vary depending on the specific ingredient and how many ingredients are present in the combination. Generally, the mass ratio between any two ingredients in any combination of the present invention, independently of one another, is from 100:1 to 1 :100, including from 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 89:11, 88:12, 87:13, 86:14, 85:15, 84:16, 83:17, 82:18, 81:19, 80:20, 79:21, 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71:29, 70:30, 69:31, 68:32, 67 :33,

66:34, 65:45, 64:46, 63:47, 62:48, 61:49, 60:40, 59:41, 58:42, 57:43, 56:44, 55:45, 54:46, 53:47, 52:48,

51:49, 50:50, 49:51, 48:52, 47:53, 46:54, 45:55, 44:56, 43:57, 42:58, 41 :59, 40:60, 39:61, 38:62, 37:63,

36:64, 35:65, 34:66, 33:67, 32:68, 31:69, 30:70, 29:71, 28:72, 27:73, 26:74, 25:75, 24:76, 23:77, 22:78,

21:79, 20:80, 19:81, 18:82, 17:83, 16:84, 15:85, 14:86, 13:87, 12:88, 11:89, 10:90, 9:91, 8:92, 7:93, 6:94, 5:95, 4:96, 3:97, 2:98, to 1:99.

The combination of the present invention (i.e. those comprising a compound of the present invention and one more other biological active agent) may be applied simultaneously or sequentially.

In the event, the ingredients of a combination are applied sequentially (i.e., one after the other), the ingredients are applied sequentially within a reasonable period of each other to attain the biological performance, such as within a few hours or days. The order of applying the ingredients in the combination, i.e., whether the compounds of formula (I) should be applied first or not is not essential for working the present invention.

In the event ingredients of the combinations are applied simultaneously in the present invention, they may be applied as a composition containing the combination, in which case (A) the compound of formula (I) and the one or more other ingredients in the combinations can be obtained from separate formulation sources and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry), or (B) the compound of formula (I) and the one or more other ingredients can be obtained as single formulation mixture source (known as a pre-mix, ready-mix, concentrate, or formulated product).

In an embodiment, independent of other embodiments, a compound according to the present invention is applied as a combination. Accordingly, the present invention also provides a composition comprising a compound according to the invention as herein described and one or more other biological active agents, and optionally one or more customary formulation auxiliaries; which may be in the form of a tank-mix or pre-mix composition.

The mixtures of active substances according to the present invention are suitable as fungicides, as are the compounds of formula (I). They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). In addition, it is referred to the explanations regarding the fungicidal activity of the compounds and the compositions containing compounds of formula (I), respectively.

The invention is now illustrated in further details by the following examples, without imposing any limitation thereto.

CHEMISTRY EXAMPLES:

All 'H-NMR spectra were recorded in the respectively indicated solvents, and the chemical shifts are reported in d units downfield from the internal standard tetramethylsilane (TMS). Inter proton coupling constants are reported in Hertz (Hz).

Example 1: 5-(Benzyl(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one (R'= methyl) (Compound 1):

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (700 mg, 3.74 mmol) in tetrahydrofuran (7 mL), /V-benzylmethanamine (453 mg, 3.74 mmol) and triethylamine (0.63 mL, 4.49 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent- hexane to 30 % ethyl acetate in hexane) to obtain 5-(benzyl(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one (457 mg, 1.68 mmol, 45 % yield).

Example 2: 3-(((4-Chloro-3-oxo-3H-l,2-dithiol-5-yl)amino)methyl)benzoni trile (Compound 87):

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (500 mg, 2.67 mmol) in tetrahydrofuran (10 mL), 3-(aminomethyl)benzonitrile (353 mg, 2.67 mmol) and triethylamine (0.45 mL, 3.21 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. Water was added to the reaction mixture and the product was extracted twice with ethyl acetate (50 mL). The ethyl acetate layer was washed with brine (50 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was then purified by column chromatography on silica gel (eluent-hexane to 50 % ethyl acetate in hexane) to obtain 3-(((4-chloro-3-oxo-3H-l,2-dithiol-5- yl)amino)methyl)benzonitrile (205 mg, 0.72 mmol, 27 % yield). Example 3: 3-(((4-Chloro-3-oxo-3H-l,2-dithiol-5-yl)(methyl)amino)methyl )benzonitrile (Compound

88)

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (500 mg, 2.67 mmol) in tetrahydrofuran (10 mL), 3-((methylamino)methyl)benzonitrile (391 mg, 2.67 mmol) and triethylamine (0.45 mL, 3.21 mmol) were added at 0 °C. The reaction was allowed to stir at 25 °C for 3 h. Water was added to the reaction mixture and the product was extracted twice with ethyl acetate (50 mL). The ethyl acetate layer was washed with brine (50 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was then purified by column chromatography on silica gel (eluent-hexane to 30 % ethyl acetate in hexane) to obtain 3-(((4-chloro-3-oxo-3H-l,2-dithiol-5- yl)(methyl)amino)methyl)benzonitrile (455 mg, 1.53 mmol, 57 % yield).

Example 4: 5-((3-Bromobenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-o ne (Compound 14)

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (750 mg, 4.01 mmol) in tetrahydrofuran (20 mL), l-(3-bromophenyl)-/V-methylmethanamine (800 mg, 4.01 mmol) and triethylamine (0.67 mL, 4.81 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. Water was added to the reaction mixture and the product was extracted twice with ethyl acetate (50 mL). The ethyl acetate layer was washed with brine (50 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was then purified by column chromatography on silica gel (eluent-hexane to 50 % dichloromethane in hexane) to obtain 5-((3- bromobenzyl)(methyl)amino)-4-chloro-3H-l,2-dithiol-3-one (730 mg, 2.08 mmol, 52 % yield).

Example 5: 4-Chloro-5-((3,4-dimethoxybenzyl)(methyl)amino)-3H-l,2-dithi ol-3-one (Compound 32)

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (500 mg, 2.67 mmol) in tetrahydrofuran (5 mL), l-(3,4-dimethoxyphenyl)-/V-methylmethanamine (484 mg, 2.67 mmol) and triethylamine (0.56 mL, 4.01 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent-hexane to 50 % ethyl acetate in hexane) to obtain 4-chloro-5-((3,4- dimethoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one (280 mg, 0.84 mmol, 32 % yield).

Example 6: 4-Chloro-5-(methyl(2,4,6-trichlorobenzyl)amino)-3H-l,2-dithi ol-3-one (Compound 8)

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (400 mg, 2.14 mmol) in tetrahydrofuran (5 mL), /V-methyl- 1 -(2,4,6-trichlorophenyl jmethanamine (480 mg, 2.14 mmol) and triethylamine (0.45 mL, 3.21 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent-hexane to 20 % ethyl acetate in hexane) to obtain 4-chloro-5- (methyl(2,4,6-trichlorobenzyl)amino)-3H-l,2-dithiol-3-one (229 mg, 0.61 mmol, 29 % yield). Example 7: 4-Chloro-5-((l-(2,4-dichlorophenyl)ethyl)amino)-3H-l,2-dithi ol-3-one (Compound 79)

To a stirred solution of l-(2,4-dichlorophenyl)ethan-l -amine (508 mg, 2.67 mmol) and triethylamine (0.56 mL, 4.01 mmol) in tetrahydrofuran (10 mL), 4,5-dichloro-3H-l,2-dithiol-3-one (500 mg, 2.67 mmol) was added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent-hexane to 20 % ethyl acetate in hexane) to obtain 4-chloro-5-((l-(2,4- dichlorophenyl)ethyl)amino)-3H-l,2-dithiol-3-one (200 mg, 0.59 mmol, 22 % yield).

Example 8: 4-Chloro-5-((2-hydroxy-2-phenylethyl)amino)-3H-l,2-dithiol-3 -one (Compound 81)

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (500 mg, 2.67 mmol) and triethylamine (0.56 mL, 4.01 mmol) in tetrahydrofuran (200 mL), 2-Amino-l-phenylethanol (367 mg, 2.67 mmol) was added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent- hexane to 50 % ethyl acetate in hexane) to obtain 4-chloro-5-((2-hydroxy-2-phenylethyl)amino)-3H-l,2- dithiol-3-one (210 mg, 0.73 mmol, 27 % yield).

Example 9: 4-Chloro-5-(methyl(pyridin-2-ylmethyl)amino)-3H-l,2-dithiol- 3-one (Compound 52)

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (700 mg, 3.74 mmol) in tetrahydrofuran (10 mL), /V-methyl-l-(pyridin-4-yl)methanamine (457 mg, 3.74 mmol) and triethylamine (0.63 mL, 4.49 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent-hexane to 70 % ethyl acetate in hexane) to obtain 4-chloro-5-(methyl(pyridin-4- ylmethyl)amino)-3H-l,2-dithiol-3-one (370 mg, 1.36 mmol, 36 % yield).

Example 10: 4-Chloro-5-(methyl(thiophen-2-ylmethyl)amino)-3H-l,2-dithiol -3-one (Compound 77)

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (700 mg, 3.74 mmol) in tetrahydrofuran (12 mL), /V-methyl - 1 -(thiophen-2-yl jmethanamine (476 mg, 3.74 mmol) and triethylamine (0.63 mL, 4.49 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent-hexane to 30 % ethyl acetate in hexane) to obtain 4-chloro-5-(methyl(thiophen-2- ylmethyl)amino)-3H-l,2-dithiol-3-one (370 mg, 1.33 mmol, 36 % yield).

Example 11: 4-Chloro-5-(methyl(pyrimidin-5-ylmethyl)amino)-3H-l,2-dithio l-3-one (Compound 76)

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (650 mg, 3.47 mmol) in tetrahydrofuran (12 mL), /V-methyl-l-(pyrimidin-5-yl)methanamine (428 mg, 3.47 mmol) and triethylamine (0.58 mL, 4.17 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent-hexane to 60 % ethyl acetate in hexane) to obtain 4-chloro-5-(methyl(pyrimidin-5- ylmethyl)amino)-3H-l,2-dithiol-3-one (205 mg, 0.75 mmol, 22 % yield).

Example 12: 4-Chloro-5-((4-hydroxy-3-methoxybenzyl)(methyl)amino)-3H-l,2 -dithiol-3-one

(Compound 26)

To a stirred solution of 4,5-dichloro-3H-l,2-dithiol-3-one (1.0 g, 5.35 mmol) in tetrahydrofuran (20 mL), 2-methoxy-4-((methylamino)methyl)phenol (0.9 g, 5.35 mmol) and triethylamine (1.12 mL, 8.02 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent-hexane to 60 % ethyl acetate in hexane) to obtain 4-chloro-5-((4-hydroxy-3- methoxybenzyl)(methyl)amino)-3H-l,2-dithiol-3-one (650 mg, 2.04 mmol, 38 % yield).

Example 13: 4-(((4-Chloro-3-oxo-3H-l,2-dithiol-5-yl)(methyl)amino)methyl )-2-methoxyphenyl methanesulfonate (Compound 30)

To a stirred solution of 4-chloro-5-((4-hydroxy-3-methoxybenzyl)(methyl)amino)-3H-l,2 -dithiol-3-one (600 mg, 1.89 mmol) in dichloromethane (12 mL), triethylamine (0.58 mL, 4.15 mmol) and methanesulfonyl chloride (0.16 mL, 2.08 mmol) were added at 0 °C. The reaction mixture was allowed to stir at 25 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated and purified by combiflash chromatography on silica gel (eluent-hexane to 60 % ethyl acetate in hexane) to obtain 4- (((4-chloro-3-oxo-3H-l,2-dithiol-5-yl)(methyl)amino)methyl)- 2-methoxyphenyl methanesulfonate (650 mg, 1.64 mmol, 87 % yield).

The following table- 1 illustrates in a non- limiting manner examples of compounds according to the invention that were prepared using analogous procedures as mentioned in the examples above. In the following examples, H-NMR data of selected examples are written in the form of H-NMR-peak lists. To each signal peaks the d-value in ppm and the no of proton in round brackets are listed.

For calibrating chemical shift for 'H spectra, tetramethylsilane was used and/or the chemical shift of the respective solvent, especially in the case of spectra measured in dimethyl sulfoxide. Therefore, in NMR peak lists, tetramethylsilane peak can occur, but not necessarily.

The following compounds in table- 1 or table-2 were obtained using analogous procedures as described in the schemes 1-9 or in the examples.

Table: 1

* Compound names generated using Chemdraw Professional 17.1.

Table: 2

* Compound names generated using Chemdraw Professional 17.1.

As described herein the compounds of formula (I) show fungicidal activity which is exerted with respect to numerous phytopathogenic fungi which attack important agricultural crops. Compounds of the present invention were assessed for activity against one or more of the following:

Biological Test Examples

Example 1: Pyricularia oryzae (Rice blast): Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds, 1 2 4 5 7 16 18 19 20 21 22 23 24 26 27 29 31 33 35 37 38 39

40 41 42 45 46 47 48 49 50 51 52 55

56 57 58 60 63 64 68 70 76 77 78 80

81 82 83 84 86 87 88 90 92 93 94 96

101 102 103 104 105 106 107 108 109 110 111 112

113 114 116 117 118 119 121 122 123 124 125 126

127 129 131 132 133 134 135 136 139 140 141 142

144 145 146 147 148 150 152 154 155 156 157 158

160 163 164 165 166 167 168 169 170 173 177 178

180 181 182 183 184 186 187 at 300 ppm showed more than 70% control in these tests when compared to the untreated check which showed extensive disease development.

Example 2: Rhizoctonia solani (Rice sheath blight/Potato black scurf):

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds, 1 2 4 5 6 7 18 21 24 29

39 42 45 47 48 49 50 51 52 57 61 63

64 70 78 80 87 88 90 99 116 126 129 140

142 164 165 178 187 at 300 ppm showed more than 70% control in these tests when compared to the untreated check which showed extensive disease development.

Example 3: Botrytis cinerea (Gray mold):

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 22 °C temperature and 90% relative humidity for seven days and radial growth was measured. Compounds, 1 2 5 7 18 19 20 21 22 24

29 33 41 42 45 47 48 50 51 61 63 64

70 78 80 82 83 84 86 88 90 92 96 103

117 121 126 127 131 144 146 160 165 168 183 at 300 ppm showed more than 70% in these tests when compared to the untreated check which showed extensive disease development.

Example 4: Alternaria solani (early blight of tomato/potato):

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into Petri dishes. 5mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with 5mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds, 1 2 3 4 5 6 7 9 12 13 14 15 16 18 19 20 21 22 25 26 29 35

37 39 40 41 42 43 44 45 46 47 48 49

50 51 52 53 54 55 56 60 61 62 63 64

65 66 67 68 70 72 73 75 76 77 78 79

80 81 82 83 84 85 86 87 88 89 90 91

92 93 94 95 96 97 99 101 103 104 110 114

116 117 120 121 122 123 124 125 126 127 128 129

130 131 132 136 139 140 141 142 144 145 146 148

150 152 153 154 155 156 157 158 160 162 164 165

166 169 170 173 174 177 178 181 182 183 184 186

187 at 300 ppm showed more than 70% control in these tests when compared to the untreated check which showed extensive disease development.

Example 5: Colletotrichum capsici (anthracnose):

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds, 1 2 5 7 15 16 18 19 20 21 22 24 26 27 29 37 39 40 41 42 45 47

48 49 50 51 63 64 68 70 78 79 80 82

88 92 93 96 98 99 101 102 103 104 106 108

110 111 112 114 115 116 117 118 121 122 123 126

127 129 131 140 141 142 144 145 146 148 150 154

155 156 157 158 160 164 165 166 169 170 177 179

181 182 183 184 187 at 300 ppm showed more than 70% control in these tests when compared to the untreated check which showed extensive disease development.

Example 6: Corynespora cassicola (Leaf spot of tomato):

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25 °C temperature and 70% relative humidity for seven days and radial growth was measured. Compounds, 1 2 3 4 16 27 45 47 48 49

50 51 52 60 63 64 67 68 70 78 80 82

84 88 92 93 101 103 116 117 121 129 131 140

142 144 148 155 157 160 164 177 at 300 ppm showed more than 70% control in these tests when compared to the untreated check which showed extensive disease development.

Example 7: Fusarium culmorum (Foot rot of cereals):

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds, 1 5 18 21 29 47 48 50 51 52

64 at 300 ppm showed 70% control in these tests when compared to the untreated check which showed extensive disease development.

Example 8: Phytophthora infestans (Late blight of potato & tomato):

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to rye agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 18 °C temperature and 95% relative humidity for seven days and radial growth was measured.

Compounds, 1 2 4 6 7 21 23 26 29 32 34

43 45 47 48 49 50 51 52 53 54 55 56

57 58 59 60 61 62 63 64 65 66 67 68

69 70 72 75 76 77 78 80 81 83 84 87

88 89 90 91 92 93 94 95 98 99 116 117

118 119 120 121 122 123 124 125 126 127 128 129

130 131 132 133 134 136 139 142 144 145 146 151

152 153 154 155 156 158 159 160 164 165 168 173

174 178 187 at 300 ppm showed 70% control in these tests when compared to the untreated check which showed extensive disease development.

Having described the invention with reference to certain preferred aspects, other aspects will become apparent to one skilled in the art from consideration of the specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, may be practiced without departing from the scope of the invention.