3-Phenyl-5-trifluoromethyl-1,2,4-oxadiazole compounds which are useful pesticides

• US 4,871,753 A
• Filed: 12/09/1987
• Issued: 10/03/1989
• Est. Priority Date: 12/12/1986
• Status: Expired due to Fees

• Current Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Rohr, Otto
• Primary Examiner(s): Lee, Mary C.
• Assistant Examiner(s): NORTHINGTON DAVIS, ZINNA
• Application Number:
  US07/130,833
• Time in Patent Office: 664 Days
• Field of Search: 548/131, 514/364
• US Class Current: 514/364
• CPC Class Codes: A01N 43/82 five-membered rings with three ring hetero atoms
• CPC Class Codes: A01N 47/06 containing —O—CO—O— groups; Thio analogues thereof
• CPC Class Codes: A01N 47/20 N-Aryl derivatives thereof
• CPC Class Codes: A01N 47/22 O-Aryl or S-Aryl esters thereof
• CPC Class Codes: A01N 47/30 Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
• CPC Class Codes: C07D 271/06 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles

Abstract

Compositions containing as active component a compound of the formula ##STR1## in which Y represents OR'"'"' or HNR" and Z represents hydrogen or (R₄)_n, and which covers, as sub-groups, the compounds of the formulae I'"'"' and I" ##STR2## in which: R'"'"' represents hydrogen, C₁ -C₄ -alkyl, aryl, substituted aryl, C(X)NR₁ '"'"'(R₂ '"'"'), C(O)XR₃ '"'"' or COR₃ '"'"';

R₁ '"'"' represents C₁ -C₉ -alkyl, C₁ -C₄ -alkoxy, C₂ -C₄ -alkenyl, aryl or substituted aryl;

R₂ '"'"' represents hydrogen or C₁ -C₄ -alkyl;

R₃ '"'"' represents C₁ -C₁₅ -alkyl, C₂ -C₄ -alkenyl or aryl;

R₄ represents halogen, C₁ -C₄ -alkoxy or nitro; and

n represents 0, 1 or 2;

X represents oxygen or sulphur;

R" represents C(O)NR₁ "(R₂ "), C(S)NR₁ "(R₂ "), COOR₃ ", COSR₃ " or COR₃ ";

R₁ " represents C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or aryl;

R₂ " represents hydrogen or C₁ -C₄ -alkyl and

R₃ " represents C₁ -C₉ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₄ -alkenyl or aryl;

including their acid addition salts.

The active ingredients have microbicidal properties and are suitable especially for controlling phytopathogenic microorganisms.

Claims

1. A composition for controlling phytopathogenic microorganisms or for preventing plants from being attacked by phytopathogenic microorganisms, which composition contains as active component at least one compound of the formula ##STR33## in which Y represents OR'"'"' or HNR"

R'"'"' represents hydrogen, C₁ -C₄ -alkyl, phenyl, naphthyl, halophenyl, halonaphthyl, C₁ -C₄ -alkyl-phenyl, C₁ -C₄ -alkyl-naphthyl, mono-, di- or trihalomethylphenyl, mono-, di- or trihalomethylnaphthyl, mono-, di- or trihaloethylphenyl, mono-, di- or trihaloethylnaphthyl, C(X)NR₁ '"'"'(R₂ '"'"'), C(O)XR₃ '"'"' or COR₃ '"'"';

R₁ '"'"' represents C₁ -C₉ -alkyl, C₁ -C₄ -alkoxy, C₂ -C₄ -alkenyl, phenyl, naphthyl, halophenyl, halonaphthyl, C₁ -C₄ -alkyl-phenyl, C₁ -C₄ -alkyl-naphthyl, mono-, di- or trihalomethylphenyl, mono-, di- or trihalomethylnaphthyl, mono-, di- or trihaloethylphenyl, or mono-, di- or trihaloethylnaphthyl,

R₂ '"'"' represents hydrogen or C₁ -C₄ -alkyl;

R₃ '"'"' represents C₁ -C₁₅ -alkyl, C₂ -C₄ -alkyl, phenyl or naphthyl;

R₄ represents halogen, C₁ -C₄ -alkoxy or nitro; and

n represents 0, 1 or 2;

X represents oxygen or sulfur;

R" represents C(O)NR₁ "(R₂ "), C(S)NR₁ "(R₂ "), COOR₃ ", COSR₃ " or COR₃ ";

R₁ " represents C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl or naphthyl;

R₂ " represents hydrogen or C₁ -C₄ -alkyl and

R₃ " represents C₁ -C₉ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₄ -alkenyl, phenyl or naphthyl;

provided that the radical ##STR34## is in the 4-position of the phenyl ring when Y is HNR";

or an acid addition salt thereof, together with a carrier.

2. A composition of claim 1, wherein Y is OR'"'"'.

10. A composition of claim 1, wherein Y is NHR" and n is 0.

12. A compound of claim 10, in which

R₁ " represents C₁ -C₂ -alkyl, C₁ -C₂ -alkoxy or phenyl;

R₂ " represents hydrogen or C₁ -C₂ -alkyl and

R₃ " represents C₁ -C₃ -alkyl, C₁ -C₂ -haloalkyl, C₃ -C₄ -alkenyl or phenyl.

13. A compound of claim 10 selected from the group consisting of:

3-[4-(3-methyl-3-methoxyureido)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-[4-(3,3-dimethylureido)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-(4-methoxycarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(4-ethoxycarbonylaminophenyl)-5-trifluoromethyl-1,2,4l -oxadiazole;

3-(4-isopropoxycarbonylaminophenyl)-5-trifluoromethyl-12,4-oxadiazole;

3-(4-phenyloxycarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(4-acetylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(4-allyloxycarbonylaminophenyl)-5-trifluoromethyl-1,24-oxadiazole;

3-[4-(2-chloroethoxycarbonylamino)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-[4-(3-methylthioureido)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-[4-(3,3-dimethylthioureido)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-[4-(3-methyl-3-methoxythioureido)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-(4-ethylthiocarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole; and

3-(4-chloromethylcarbonylaminophenyl)-5-trifluoromethyl-1,2,4,-oxadiazole.

14. The method of claim 2 wherein the applied compound is selected from the group consisting of:

3-[3-(3,3-dimethylureido)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-[3-(3-methyl-3-methoxyureido)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-[3-(3-methylureido)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-(3-ethoxycarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(3-chloromethoxycarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(3-methoxycarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(3-isopropoxycarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(3-phenoxycarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(3-allyloxycarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole; and

3-[3-(2-chloroethoxycarbonylamino)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

to said plants or to the locus thereof.

15. A composition of claim 1, which contains from 0.1 to 99% of the active component, from 99.9 to 1% solid or liquid adjuvant and from 0 to 25% surfactant.

16. A composition of claim 14, which contains from 0.1 to 95% of the active component, from 99.8 to 5% solid or liquid adjuvant and from 0.1 to 25% surfactant.

18. The method of controlling phytopathogenic microorganisms on plants or of preventing cultivated plants from being attacked by said microorganisms which comprises applying a compound of claim 10 to said plants or to the locus thereof.

3. A compound of the formula ##STR35## in which R'"'"' represents hydrogen, C₁ -C₄ -alkyl, phenyl, naphthyl, halophenyl, halonaphthyl, C₁ -C₄ -alkyl-phenyl, C₁ -C₄ -alkyl-naphthyl, mono-, di- or trihalomethylphenyl, mono-, di- or trihalomethylnaphthyl, mono-, di- or trihaloethylphenyl, mono-, di- or trihaloethylnaphthyl, C(X)NR₁ '"'"'(R₂ '"'"'), C(O)XR₃ '"'"' or COR₃ '"'"';

R₁ '"'"' represents C₁ -C₉ -alkyl, C₁ -C₄ -alkoxy, C₂ -C₄ -alkenyl, phenyl, naphthyl, halophenyl, halonaphthyl, C₁ -C₄ -alkyl-phenyl, C₁ -C₄ -alkyl-naphthyl, mono-, di- or trihalomethylphenyl, mono-, di- or trihalomethylnaphthyl, mono-, di- or trihaloethylphenyl, or mono-, di- or trihaloethylnaphthyl;

R₂ '"'"' represents hydrogen or C₁ -C₄ -alkyl;

R₃ '"'"' represents C₁ -C₁₅ -alkyl, C₂ -C₄ -alkenyl, phenyl or naphthyl;

R₄ represents halogen, C₁ -C₄ -alkoxy or nitro;

n represents 0, 1 or 2; and

X represents oxygen or sulfur;

or an acid addition salt thereof.

4. A compound of claim 3, wherein n is 0.

5. A compound of claim 4, in which,

R'"'"' represents hydrogen, phenyl, halophenyl, C₁ -C₄ -alkyl-phenyl, mono-, di- or trihalomethylphenyl, mono-, di- or trihaloethylphenyl, C(X)NR₁ '"'"'(R₂ '"'"'), C(O)XR₃ '"'"' or COR₃ '"'"';

7. A compound of claim 4, in which the radical ##STR36## is in the 4-position of the phenyl ring, R'"'"' represents hydrogen, phenyl, phenyl substituted by halogen or by methyl, C(X)NR₁ '"'"'(R₂), C(O)XR₃ '"'"' or COR₃ '"'"', in which R₁ '"'"' represents C₁ -C₄ -alkyl, C₁ -C₂ -alkoxy, allyl or phenyl;

R₂ '"'"' represents hydrogen or C₁ -C₂ -alkyl; and

R₃ '"'"' represents C₁ -C₉ -alkyl, C₂ -C₄ -alkenyl or phenyl.

8. A compound of claim 4, in which the radical is in the 4-position of the phenyl ring, R'"'"' represents hydrogen, C₁ -C₄ -alkyl, phenyl, halophenyl, C₁ -C₄ -alkyl-phenyl, mono-, di- or trihalomethylphenyl, mono-, di- trihaloethylphenyl, C(X)NR₁ '"'"'(R₁ '"'"'), C(O)XR₃ '"'"' or COR₃ '"'"';

R₁ '"'"' represents C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, allyl or phenyl; and

R₃ '"'"' represents C₁ -C₉ -alkyl, C₂ -C₄ -alkenyl or phenyl.

9. A compound of claim 4, selected from the group consisting of:

3-(4-methylaminocarbonyloxyphenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(4-isopropylaminocarbonyloxyphenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(4-ethylaminocarbonyloxyphenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-(4-allylaminocarbonyloxyphenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-[4-(2-chloro-4-trifluoromethylphenoxy)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-[methoxy-(methyl)-aminocarbonyloxyphenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-(4-hexanoyloxyphenyl)-5-trifluoromethyl-1,2,4-oxadiazole;

3-[4-(phenylaminocarboxy)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole;

3-[4-(2-methyl-3-chlorophenylaminocarboxy)-phenyl]-5-trifluoromethyl-1,2,4-oxadiazole; and

3-[4-(3-ethylphenylaminocarboxyphenyl)]-5-trifluoromethyl-1,2,4-oxadiazole.

17. The method of controlling phytopathogenic microorganisms on plants or of preventing cultivated plants from being attacked by said microorganisms which comprises applying a compound of claim 3 to said plants or to the locus thereof.

6. R₁ '"'"' represents C₁ -C₉ -alkyl, C₁ -C₄ -alkoxy, C₂ -C₄ -alkenyl or phenyl;

and

R₃ '"'"' represents C₁ -C₁₅ -alkyl, C₂ -C₄ -alkenyl or phenyl.

11. A compound of the formula ##STR37## in which R" represents C(O)NR₁ "(R₂ "), C(S)NR₁ "(R₂ "), COOR₃ ", COSR₃ " or COR₃ ";

R₁ " represents C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl or naphthyl;

R₂ " represents hydrogen or C₁ -C₄ -alkyl and

R₃ " represents C₁ -C₉ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₄ -alkenyl, phenyl or naphthyl.

19. A method of controlling phytopathogenic microorganisms on plants or of preventing cultivated plants from being attacked by said microorganisms, comprising the step of applying a compound of the formula ##STR38## in which Y represents OR'"'"' or HNR"

R'"'"' represents hydrogen, C₁ -C₄ -alkyl, phenyl, naphthyl, halophenyl, halonaphthyl, C₁ -C₄ -alkyl-phenyl, C₁ -C₄ -alkyl-naphthyl, mono-, di- or trihalomethylphenyl, mono-, di- or trihalomethylnaphthyl, mono-, di- or trihaloethylphenyl, mono-, di- or trihaloethylnaphthyl, C(X)NR₁ '"'"'(R₂ '"'"'), C(O)XR₃ '"'"' or COR₃ '"'"';

R₁ '"'"' represents C₁ -C₉ -alkyl, C₁ -C₄ -alkoxy, C₂ -C₄ -alkenyl, phenyl, naphthyl, halophenyl, halonaphthyl, C₁ -C₄ alkyl-phenyl, C₁ -C₄ alkyl-naphthyl, mono-, di- or trihalomethylphenyl, mono-, di- or trihalomethylnaphthyl, mono-, di- or trihalomethylethylphenyl, or mono-, di- or trihalomethylnaphthyl,

R₂ '"'"' represents hydrogen or C₁ -C₄ -alkyl;

R₃ '"'"' represents C₁ -C₁₅ -alkyl, C₂ -C₄ -alkyl, phenyl or naphthyl;

R₄ represents halogen, C₁ -C₄ -alkoxy or nitro; and

n represents 0, 1 or 2;

X represents oxygen or sulfur;

R" represents C(O)NR₁ "(R₂ "), C(S)NR₁ "(R₂ "), COOR₃ ", COSR₃ " or COR₃ ";

R₁ " represents C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl or naphthyl;

R₂ " represents hydrogen or C₁ -C₄ -alkyl and

R₃ " represents C₁ -C₉ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₄ -alkenyl, phenyl or naphthyl;

or an acid addition salt thereof.