Benzocyclobutane(thio) carboxamides

1. Benzocyclobutane(thio) carboxamide of formula (I)

in which

Ar represents a radical selected from the group Ar1 to Ar15:

X 1 , X 2 , X 3 , X 4 and X 5 independently represent hydrogen; halogen; cyano; nitro, hydroxyl; C 1 -C 16 -alkyl, C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; or C 1 -C 6 -haloalkoxy having 1 to 9 identical or different halogen atoms;

T represents an oxygen or sulfur atom;

Q represents hydrogen, C 1 -C 6 -alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkylsulfonyl, or halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;

X represents halogen, nitro, cyano, C 1 -C 12 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfanyl; C 1 -C 6 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfinyl; C 1 -C 6 -haloalkylsulfinyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfonyl; C 1 -C 6 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 12 -alkenyl; C 2 -C 12 -alkynyl; C 3 -C 7 -cycloalkyl; phenyl; or tri(C 1 -C 8 )alkylsilyl; tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl;

m represents 0, 1, 2 or 3;

R 1 , R 2 , R 3 and R 4 independently one to another represent hydrogen; halogen; C 1 -C 16 -alkyl; C 2 -C 16 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 8 -cycloalkyl; C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyl; (C 3 -C 8 -cycloalkyl)-C 3 -C 8 -cycloalkyl; C 2 -C 16 -alkenyl; C 2 -C 16 -alkynyl; C 2 -C 16 -alkenyl-C 1 -C 16 -alkyl; C 2 -C 16 -alkynyl-C 1 -C 16 -alkyl; C 1 -C 16 -alkoxy; C 3 -C 8 -cycloalkyloxy; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyloxy; C 1 -C 8 -alkylsulfanyl; C 3 -C 8 -cycloalkylsulfanyl; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkylsulfanyl; C 2 -C 16 -alkenyloxy; C 3 -C 8 -alkynyloxy; aryl which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 1 -C 8 -alkyloxy which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 1 -C 8 -alkylsulfanyl which is optionally substituted by up to 6 identical or different groups R b ; aryloxy which is optionally substituted by up to 6 identical or different groups R b ; arylsulfanyl which is optionally substituted by up to 6 identical or different groups R b ; (C 3 -C 8 -cycloalkyl)-C 2 -C 8 -alkenyl; (C 3 -C 8 -cycloalkyl)-C 2 -C 8 -alkynyl; tri(C 1 -C 8 )alkylsilyl; tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; aryl-C 1 -C 8 -alkyl which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 2 -C 8 -alkenyl which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 2 -C 8 -alkynyl which is optionally substituted by up to 6 identical or different groups R b ;

provided that R 1 , R 2 , R 3 and R 4 do not simultaneously represent hydrogen or

R 1 and R 2 represent together with the carbon to which they are attached a C 3 -C 8 -cycloalkyl; C 3 -C 8 -cycloalkenyl, each of which is optionally substituted or

R 1 and R 2 represent a group ═C(Y 1 )Y 2 or

R 1 and R 2 represent a 5 or 6 membered ring containing 1 or 2 heteroatoms or

R 3 and R 4 represent together with the carbon to which they are attached a C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl each of which is optionally substituted or

R 3 and R 4 represent a group ═C(Y 1 )Y 2 or

R 3 and R 4 represent a 5 or 6 membered ring containing 1 or 2 heteroatoms or

R 1 and R 3 represent with the carbons to which they are attached a C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl each of which is optionally substituted;

R b represents halogen; nitro, cyano, C 1 -C 12 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfanyl; C 1 -C 6 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfonyl; C 1 -C 6 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 12 -alkenyl; C 2 -C 12 -alkynyl; C 3 -C 7 -cycloalkyl; phenyl; tri(C 1 -C 8 )alkylsilyl; or tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl;

Y 1 and Y 2 independently of one another represent hydrogen, halogen, C 1 -C 12 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 8 -alkylsulfanyl; phenyl; each of which is optionally substituted or Y 1 and Y 2 can form together with the carbon to which they are attached a C 3 -C 8 -cycloalkyl or a C 3 -C 8 -cycloalkenyl or a saturated 5, 6 or 7 membered heterocycle; each of which is optionally substituted.

2. Benzocyclobutane(thio) carboxamide of formula (I) according to claim 1

in which

Ar represents a radical selected from the group Ar1, Ar2, Ar4, Ar7, Ar8, Ar10 and Ar13;

X 1 represents halogen; C 1 -C 16 -alkyl, C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 7 -cycloalkyl, or C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms;

X 2 , X 3 , X 4 and X 5 independently from each other represent hydrogen, halogen, C 1 -C 16 -alkyl, C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 7 -cycloalkyl, or C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms;

T represents an oxygen atom;

Q represents hydrogen, C 1 -C 4 -alkylsulfonyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -haloalkylsulfonyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl having in each case 1 to 9 fluorine, chlorine or bromine atoms;

X represents fluorine, chlorine, methyl or trifluoromethyl;

m represents 0, 1 or 2;

R 1 , R 2 , R 3 and R 4 independently of one another represent hydrogen; halogen; C 1 -C 16 -alkyl; C 2 -C 16 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 8 -cycloalkyl; C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyl; (C 3 -C 8 -cycloalkyl)-C 3 -C 8 -cycloalkyl; C 1 -C 16 -alkoxy; C 3 -C 8 -cycloalkyloxy; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyloxy; aryl which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 1 -C 8 -alkyloxy which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 1 -C 8 -alkyl which is optionally substituted by up to 6 identical or different groups R b ;

provided that R 1 , R 2 , R 3 and R 4 do not simultaneously represent hydrogen or

R 1 and R 2 represents together with the carbon to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl where the substituents can be chosen from halogen and C 1 -C 6 -alkyl or

R 3 and R 4 represents together with the carbon to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl where the substituents can be chosen from halogen and C 1 -C 6 -alkyl or

R 1 and R 3 represents together with the carbons to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl where the substituents can be chosen from halogen and C 1 -C 6 -alkyl;

R b represents halogen; nitro, cyano, C 1 -C 8 -alkyl; C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; C 1 -C 4 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfanyl; C 1 -C 4 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfonyl; C 1 -C 4 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; C 3 -C 6 -cycloalkyl; phenyl; tri(C 1 -C 6 )alkylsilyl; or tri(C 1 -C 6 )alkylsilyl-C 1 -C 6 -alkyl.

3. Benzocyclobutane(thio) carboxamide of formula (I) according to claim 1

in which

Ar represents a radical selected from the group Ar1, Ar2 and Ar4;

X 1 represents C 1 -C 12 -alkyl, C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms;

X 2 , X 3 , X 4 and X 5 independently from each other represent hydrogen, fluorine, chlorine, bromine, iodine; C 1 -C 12 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms;

T represents an oxygen atom;

Q represents hydrogen, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, trifluoromethylsulfonyl, or trifluoromethoxymethyl;

X represents fluorine

m represents 0 or 1;

R 1 , R 2 , R 3 and R 4 independently of one another represent hydrogen; halogen; C 1 -C 16 -alkyl; C 2 -C 16 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 8 -cycloalkyl; C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyl; (C 3 -C 8 -cycloalkyl)-C 3 -C 8 -cycloalkyl; C 1 -C 16 -alkoxy; aryl which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 1 -C 8 -alkyl which is optionally substituted by up to 6 identical or different groups R b ;

provided that R 1 , R 2 , R 3 and R 4 do not simultaneously represent hydrogen or

R 1 and R 2 represents together with the carbon to which they are attached an optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl where the substituents can be chosen from fluorine, chlorine, methyl and ethyl or

R 3 and R 4 represents together with the carbon to which they are attached an optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl where the substituents can be chosen from fluorine, chlorine, methyl and ethyl;

R b represents fluorine, chlorine, bromine; C 1 -C 6 -alkyl; C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 4 -alkoxy; C 1 -C 4 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 4 -alkylsulfanyl; C 1 -C 4 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 4 -alkylsulfonyl; C 1 -C 4 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 6 -alkenyl; C 2 -C 6 -alkynyl; C 3 -C 6 -cycloalkyl; phenyl; tri(C 1 -C 4 )alkylsilyl; or tri(C 1 -C 4 )alkylsilyl-C 1 -C 4 -alkyl.

4. Benzocyclobutane(thio) carboxamide of formula (I) according to claim 1

in which

Ar represents a radical selected from the groups Ar2 and Ar4;

X 1 represents difluoromethyl;

X 2 , X 3 and X 4 independently from each other represent fluorine or chlorine;

T represents an oxygen atom;

Q represents hydrogen;

m represents 0;

R 1 , R 2 , R 3 and R 4 independently of one another represent; hydrogen, phenyl, ethyl, methyl, or propan-2-yl;

provided that R 1 , R 2 , R 3 and R 4 do not simultaneously represent hydrogen or

R 3 and R 4 represents together with the carbon to which they are attached an optionally substituted cyclopentyl, or cyclohexyl.

5. A process for preparing one or more benzocyclobutane(thio) carboxamides of formula (I) according to claim 1 , comprising reacting a compound of formula (II)

wherein Z represents halogen, cyano, hydroxyl or an activated hydroxyl group,

with a compound of formula (III-a)

wherein the definitions are the same as those recited in claim 1 ,

to obtain one or more compounds of formula (I-a)

 and in case that for the compounds according to formula (I) T represents sulfur, reacting one or more compounds of formula (I-a) in the presence of a thionating agent to obtain a compound of formula (I-b)

6. Composition for controlling phytopathogenic harmful fungi, comprising a content of at least one compound of formula (I) according to claim 1 and one or more extenders and/or surfactants.

7. Method for controlling phytopathogenic harmful fungi, comprising applying one or more compounds of formula (I) according to claim 1 to the phytopathogenic harmful fungi and/or a habitat thereof.

8. Process for producing a composition for controlling phytopathogenic harmful fungi, comprising mixing one or more compounds of the formula (I) according to claim 1 with one or more extenders and/or surfactants.

9. A method according to claim 7 comprising treatment of transgenic plants, seed or of seed of transgenic plants.

10. Benzocyclobutane(thio) carboxamide of formula (I) according to claim 1 , wherein m represents 0.

11. Benzocyclobutane(thio) carboxamide of formula (I) according to claim 1 , wherein m represents 1, 2 or 3.

12. Method for controlling phytopathogenic harmful fungi, comprising applying one or more compounds of formula (I) according to claim 4 to the phytopathogenic harmful fungi and/or a habitat thereof.