SUBSTITUTED N-BENZOYL-N'(TETRAZOLYLPHENYL)-UREAS AND THEIR USE AS PEST CONTROL AGENTS

• US 20030187043A1
• Filed: 11/08/2002
• Published: 10/02/2003
• Est. Priority Date: 05/12/2000
• Status: Active Grant

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Erdelen, Christoph, Maurer, Fritz
• Granted Patent: US 6,911,416 B2
• Time in Patent Office: Days
• US Class Current: 514/381
• CPC Class Codes: A01N 47/34 containing the groups , e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
• CPC Class Codes: C07D 257/04 Five-membered rings
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/06 linked by a carbon chain containing only aliphatic carbon atoms

Abstract

The present invention relates to new substituted N-benzoyl-N′-(tetrazolylphenyl)-ureas of the formula (I)

in which

R¹, R², R³, R⁴ and n are as stated in the description, to processes for their preparation, and to their use as pesticides.

Claims

1. Compounds of the formula (I)

2. Compounds of the formula (I) according to claim 1

in which

R¹ represents fluorine or chlorine,

R² represents hydrogen, fluorine or chlorine,

R³ represents fluorine, chlorine, bromine, C₁-C₄-alkyl or C₁-C₄-halogenoalkyl,

n represents 0, 1 or 2,

R⁴ represents hydrogen, C₁-C₆-alkyl, C₁-C₄-halogenoalkyl, C₂-C₄-alkenyl, C₂-C₄-halogenoalkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-carbonyl-C₁-C₄-alkyl, C₁-C₄-alkyl-carbonyloxy-C₁-C₄-alkyl;

C₁-C₄-alkylsulphonyl, di-(C₁-C₄-alkyl)-aminocarbonyl, or represents phenyl, benzyl or phenylsulphonyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl and C₁-C₄-halogenoalkoxy;

or represents cyclopentyl, cyclohexyl or cyclohexyl-C₁-C₂-alkyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy, or represents five- or six-membered heterocyclyl or five- or six-membered heterocyclyl-C₁-C₂-alkyl, each of which has one or two hetero atoms, such as N, O or S atoms, and each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy.

3. Compounds of the formula (I) according to claim 1

in which

R¹ represents fluorine or chlorine,

R² represents hydrogen, fluorine or chlorine,

R³ represents fluorine, chlorine, methyl or trifluoromethyl,

n represents 0, 1 or 2,

R⁴ represents hydrogen, C₁-C₆-alkyl, C₂-C₄-alkenyl, C₁-C₂-halogenoalkyl or C₂-C₄-halogenoalkenyl having in each case 1 to 3 identical or different halogen atoms from the series consisting of fluorine, chlorine and bromine;

C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkoxy-carbonyl-C₁-C₂-alkyl, C₁-C₄-alkyl-carbonyloxy-C₁-C₂-alkyl, C₁-C₂-alkylsulfonyl, di-(C₁-C₂-alkyl)-aminocarbonyl;

or represents phenyl, benzyl or phenylsulphonyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl and C₁-C₂-halogenoalkoxy having in each case 1 to 3 identical or different halogen atoms;

or represents cyclopentyl, cyclohexyl or cyclohexylmethyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;

or represents tetrahydrofuranyl, tetrahydrofuranylmethyl, tetrahydropyranyl or tetrahydropyranylmethyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy.

4. Compounds of the formula (I) according to claim 1

in which

R¹ represents fluorine or chlorine,

R² represents hydrogen, fluorine or chlorine,

R³ represents fluorine, chlorine or trifluoromethyl,

n represents 0, 1 or 2,

R⁴ represents hydrogen;

methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;

1-ethyl-1-methyl-propyl, 1,1 -dimethylpropyl, 2-methyl-2-propenyl, fluoromethyl, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2,2,2-trifluoroethyl, 3,4,4-trifluoro-3-butenyl, 4,4-difluoro-3-butenyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, methylcarbonyloxyethyl, ethylcarbonyloxyethyl, methylsulphonyl, ethylsulphonyl, dimethylaminocarbonyl, methylethylaminocarbonyl, diethylaminocarbonyl;

represents phenyl, benzyl or phenylsulphonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents from the series consisting of fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy;

or represents cyclohexyl, tetrahydropyranyl or tetrahydropyranylmethyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents from the series consisting of methyl, ethyl, methoxy or ethoxy.

5. Process for the preparation of compounds of the formula (I) according to claim 1, characterized in that

a) compounds of the formula (II)

in which

R¹ and R² are as stated above

are reacted with compounds of the formula (III)

in which

R³, n and R⁴ are as stated above

in the presence of a diluent;

and,

b) if appropriate, the resulting compounds of the formula (Ia)

in which

R¹, R², R³ and n are as stated above

are reacted with compounds of the formula (IV)

E-R^4-1  

 

(IV)

in which

R^4-1 is as stated above for R⁴, with the exception of hydrogen, and

E represents an anionic leaving group

in the presence of a diluent and, if appropriate, in the presence of an acid acceptor.

8. Pesticides and herbicides, characterized in that they contain at least one compound of the formula (I) according to claim 1.

9. Method of controlling animal pests and undesired vegetation cover, characterized in that, compounds of the formula (I) according to claim 1 are allowed to act on pests and/or their environment.

10. Use of compounds of the formula (I) according to claim 1 for controlling animal pests and undesired vegetation cover.

11. Process for the preparation of pesticides and herbicides, characterized in that compounds of the formula (I) according to claim 1 are mixed with extenders and/or surfactants.

12. Use of compounds of the formula (I) according to claim 1 for the preparation of pesticides and herbicides.

6. Compounds of the formula (III)

7. Compounds of the formula (III) according to claim 6

in which

n represents 0 and

R⁴ and the position of the substitution of the tetrazole on the phenyl ring are as stated in the table.

Position of substitution of theR⁴tetrazole on the phenyl ring4 4 2-CHF₂3 or 41-CHF₂3 or 4H3 or 42-C₄H₉-t3 or 4