Pesticidal pyrazoles and derivatives

• US 6,835,743 B2
• Filed: 05/13/2002
• Issued: 12/28/2004
• Est. Priority Date: 11/29/1996
• Status: Expired due to Term

• Current Assignee: Bayer SAS (Bayer AG)
• Original Assignee: Bayer Cropscience SA (Bayer AG)
• Inventors: Kimura, Yasuo
• Primary Examiner(s): PAK, JOHN D
• Application Number:
  US10/145,077
• Publication Number:
  US 20020132831A1
• Time in Patent Office: 960 Days
• Field of Search: 514/222.2, 514/228.8, 514/277, 514/332, 514/333, 514/336-344, 514/397, 514/402, 514/403, 514/404, 514/405, 514/406, 514/407, 514/937, 424/DIG.11
• US Class Current: 514/407
• CPC Class Codes: A01M 1/245 for pesticide application or distribution, e.g. using a network of pipes
• CPC Class Codes: A01M 2200/011 Crawling insects
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/00 Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application , e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 47/02 the carbon atom having no bond to a nitrogen atom
• CPC Class Codes: Y10S 424/11 Termite treating

Abstract

Process for the protection of a building that has already been built or is going to be built, whereby an effective amount of an insecticidally active compound is spread around or under the said building at discrete locations. The insecticide may be an arylpyrazole.

Claims

1. Process for the protection of a building against damage caused by insects comprising the steps of:

a) forming a solution or suspension of an insecticidally active ingredient in a liquid, wherein the amount of the active ingredient in the solution or suspension is from about 0.01 to about 20% by weight and the active ingredient has no quick knock down effect and a secondary killing action;

b) forming treated and untreated locations along the perimeter of the building by applying an effective amount of said solution or suspension to discrete locations around or under said building along the perimeter of the building, wherein the treated locations are the discrete locations along the perimeter of the building where said solution or suspension has been applied and the untreated locations are the remaining portions of the perimeter where the solution or suspension was not applied;

wherein the combination of said treated locations and said untreated locations along the perimeter of the building equal the total perimeter of the building and further wherein said treated locations make up 0.5 to 7.5 meter per 10 meter of the total perimeter of the building, and said active ingredient is an insecticide of the formula (I);

in which;

X represents a trivalent nitrogen atom or a C—

R₁₂ radical, wherein the other three valences of the carbon atom are part of the aromatic ring,

R₁ is CN or methyl or a halogen atom,

R₂ is S(O)_nR₃ or 4,5-dicyanoimidazol 2-yl or haloalkyl,

R₃ is alkyl or haloalkyl;

R₄ represents a hydrogen or halogen atom or a member of the group consisting of NR₅R₆, S(O)_mR₇, C(O)R₇, C(O)O—

R₇, alkyl, haloalkyl, OR₈ and —

N═

C(R₉)(R₁₀);

R₅ and R₆ are both hydrogen or together form a divalent alkylene radical which is interrupted by one or two divalent heteroatoms, said divalent heteroatoms being independently selected from the group consisting of oxygen and sulfur;

R₇ represents an alkyl or haloalkyl radical;

R₈ represents an alkyl or haloalkyl radical or a hydrogen atom;

R₉ represents an alkyl radical or a hydrogen atom;

R₁₀ represents a phenyl or heteroaryl group which may optionally be unsubstituted or substituted by one or more halogen atoms or a member of the group consisting of OH, —

O-alkyl, —

S-alkyl, cyano, and alkyl;

R₁₁ and R₁₂ represent, independently of one another, a hydrogen or halogen atom, or CN or NO₂,

R₁₃ represents a halogen atom or a haloalkyl, haloalkoxy, S(O)_qCF₃ or SF₅ group,

m, n, and q represent, independently of one another, an integer equal to 0, 1 or 2,

provided that, when R₁ is methyl, then either R₃ is haloalkyl, R₄ is NH₂, R₁₁ is Cl, R₁₃ is CF₃ and X is N;

or R₂ is 4,5-dicyanoimidazol 2-yl, R₄ is Cl, R₁₁ is Cl, R₁₃ is CF₃, and X is —

C—

Cl.

2. Process according to claim 1, wherein the active ingredient is an insecticide with contact effect, and no repellent action against the insects.

3. Process according to claim 1, wherein the active ingredient is an insecticide which is able to kill termites in a nest that is located outside of the perimeter of the building when the insecticide is brought back to the nest by termites which have contacted the treated locations.

4. Process according to claim 1, wherein the solution or suspension does no contain an attractant for termites.

5. Process according to claim 1, wherein said process is used in a preventive way.

6. Process according to claim 1, wherein said process is used in a curative way.

7. Process according to claim 1, wherein the solution or suspension is applied to soil.

8. Process according to claim 7, wherein the solution or suspension is applied by spraying on the soil or mixing with the soil.

9. Process according to claim 1, wherein the treated locations are at corners and/or crossing walls of the building.

10. Process according to claim 1, wherein the treated locations are at places which have a greater humidity level than the untreated locations.

11. Process according to claim 7, wherein the amount of active ingredient at the treated locations is within the range of 0.05 g/m² to 0.0001 g/m² per surface of the soil.

12. Process according to claim 1, wherein each of said treated locations has a width of from 1 to 50 cm.

13. Process according to claim 1, wherein at least a portion of said untreated locations either contain none of said insecticidally active ingredient or do not contain an effective amount of said insecticidally active ingredient.

14. Process according to claim 1, wherein said liquid consists essentially of water.

15. Process for the protection of a future building against damage caused by insects, said future building having a proposed outline which includes at least the location of the outer walls of the building, said process comprising the steps of:

a) forming a solution or suspension of an insecticidally active ingredient in a liquid, wherein the amount of the active ingredient in the solution or suspension is from about 0.01 to about 20% by weight and the active ingredient has no quick knock down effect and a secondary killing action;

b) forming treated and untreated locations along the outline of the future building by applying an effective amount of said solution or suspension to discrete locations around or under said future building along the outline of the future building, wherein the treated locations are the discrete locations along the outline of the future building where said solution or suspension has been applied and the untreated locations are the remaining portions of the outline where the solution or suspension was not applied;

further wherein at least a portion of said untreated locations either contain none of said insecticidally active ingredient or do not contain an effective amount of said insecticidally active ingredient and said active ingredient is an insecticide of the formula (I);

in which;

X represents a trivalent nitrogen atom or a C—

R₁₂ radical, wherein the other three valences of the carbon atom are part of the aromatic ring,

R₁ is CN or methyl or a halogen atom,

R₂ is S(O)_nR₃ or 4,5-dicyanoimidazol 2-yl or haloalkyl,

R₃ is alkyl or haloalkyl;

R₄ represents a hydrogen or halogen atom or a member of the group consisting of NR₅R₆, S(O)_mR₇, C(O)R₇, C(O)O—

R₇, alkyl, haloalkyl, OR₈ and —

N═

C(R₉)(R₁₀);

R₅ and R₆ are both hydrogen or together form a divalent alkylene radical which is interrupted by one or two divalent heteroatoms, said divalent heteroatoms being independently selected from the group consisting of oxygen and sulfur;

R₇ represents an alkyl or haloalkyl radical;

R₈ represents an alkyl or haloalkyl radical or a hydrogen atom;

R₉ represents an alkyl radical or a hydrogen atom;

R₁₀ represents a phenyl or heteroaryl group which may optionally be unsubstituted or substituted by one or more halogen atoms or a member of the group consisting of OH, —

O-alkyl, —

S-alkyl, cyano, and alkyl;

R₁₁, and R₁₂ represent, independently of one another, a hydrogen or halogen atom, or CN or NO₂,

R₁₃ represents a halogen atom or a haloalkyl, haloalkoxy, S(O)_qCF₃ or SF₅ group,

m, n, and q represent, independently of one another, an integer equal to 0, 1 or 2,

provided that, when R₁ is methyl, then either R₃ is haloalkyl, R₄ is NH₂, R₁₁ is Cl, R₁₃ is CF₃ and X

is N;

or R₂ is 4,5-dicyanoimidazol 2-yl, R₄ is Cl, R₁₁ is Cl, R₁₃ is CF₃, and X is —

C—

Cl.

16. Process according to claim 15, wherein the proposed outline includes the location of the outer walls and inner walls of the ground floor of the future building and said treated locations are areas along the outline of the future building where corners of the outer walls and/or intersections of the outer walls and crossing walls of the ground floor of the future building will be located.

17. Process according to claim 15, wherein said liquid consists essentially of water.

18. Process for the protection of a future building against damage caused by insects, said future building having a proposed outline which includes at least the location of the outer walls of the building, said process comprising the steps of:

a) forming a solution or suspension of an insecticidally active ingredient in a liquid, wherein the amount of the active ingredient in the solution or suspension is from about 0.01 to about 20% by weight and the active ingredient has no quick knock down effect and a secondary killing action;

b) forming treated and untreated locations inside the outline of the future building by applying an effective amount of said solution or suspension to discrete locations inside the outline of said future building, wherein the treated locations are the discrete locations inside the outline of the future building where said solution or suspension has been applied and the untreated locations are the remaining areas that are inside the outline where the solution or suspension was not applied;

further wherein at least a portion of said untreated locations either contain none of said insecticidally active ingredient or do not contain an effective amount of said insecticidally active ingredient and said active ingredient is an insecticide of the formula (I);

in which;

X represents a trivalent nitrogen atom or a C—

R₁₂ radical, wherein the other three valences of the carbon atom are part of the aromatic ring,

R₁ is CN or methyl or a halogen atom,

R₂ is S(O)_nR₃ or 4,5-dicyanoimidazol 2-yl or haloalkyl,

R₃ is alkyl or haloalkyl;

R₄ represents a hydrogen or halogen atom or a member of the group consisting of NR₅R₆, S(O)_mR₇, C(O)R₇, C(O)O—

R₇, alkyl, haloalkyl, OR₈ and —

N═

C(R₉)(R₁₀);

R₅ and R₆ are both hydrogen or together form a divalent alkylene radical which is interrupted by one or two divalent heteroatoms, said divalent heteroatoms being independently selected from the group consisting of oxygen and sulfur;

R₇ represents an alkyl or haloalkyl radical;

R₈ represents an alkyl or haloalkyl radical or a hydrogen atom;

R₉ represents an alkyl radical or a hydrogen atom;

R₁₀ represents a phenyl or heteroayl group which may optionally be unsubstituted or substituted by one or more halogen atoms or a member of the group consisting of OH, —

O-alkyl, —

S-alkyl, cyano, and alkyl;

R₁₁ and R₁₂ represent, independently of one another, a hydrogen or halogen atom, or CN or NO₂,

R₁₃ represents a halogen atom or a haloalkyl, haloalkoxy, S(O)_qCF₃ or SF₅ group,

m, n, and q represent, independently of one another, an integer equal to 0, 1 or 2,

provided that, when R₁ is methyl, then either R₃ is haloalkyl, R₄ is NH₂, R₁₁ is Cl, R₁₃ is CF₃ and X is N;

or R₂ is 4,5-dicyanoimidazol 2-yl, R₄ is Cl, R₁₁ is Cl, R₁₃ is CF₃, and X is —

C-Cl.

19. Process according to claim 18, wherein said liquid consists essentially of water.