# US 2014/0194480 A1 · Methods for the control of termites and ants

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- Number: US 2014/0194480 A1
- Document ID: US20140194480A1
- Status: Published application
- Kind: A1
- Application number: 14/240,140
- Filed: 2012-08-27
- Published: 2014-07-10
- Earliest claimed: 2011-08-25
- Assignees: Syngenta Participations AG
- Inventors: Mark Hoppe; Myriem El Qacemi; Jerome Yves Cassayre
- Web page: https://patentgrep.com/patent/US20140194480A1

## CPC

- A01N 43/36: five-membered rings
- A01N 43/713: having rings with four or more nitrogen atoms as the only ring hetero atoms
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

The present invention provides a method for controlling termites comprising applying a liquid formulation comprising a compound of formula I to a location where termite control is needed or is expected to be needed, wherein the compound of formula (I) is wherein X is optionally substituted aryl, optionally substituted heterocyclyl, or a group selected from X1 to X5 cycle A is aryl or heteroaryl; cycle B is a saturated or partially unsaturated heterocyclyl; cycle C is aryl or heteroaryl; R1, R2, R3, R4, R5, R6 and R8 are independently hydrogen or an organic radical; R7 is haloalkyl; G is oxygen or sulfur; L is O, NH, NR1, CR3R4; n is 0, 1, 2, 3, 4 or 5; o is 0, 1, 2, 3, 4 or 5; p is 1, 2, 3, 4 or 5. The invention also relates to methods for protecting man-made structures from termites using the compounds of formula I as well as termite baits comprising the compound of formula I. The invention also provides a method for controlling ants comprising applying a liquid formulation comprising a compound of formula I to a location where ant control is needed or is expected to be needed.

## Claims

### Claim 1

A method for controlling termites comprising applying a liquid formulation comprising a compound of formula I to a location where termite control is needed or is expected to be needed, wherein the compound of formula I is
wherein
X is optionally substituted aryl, optionally substituted heterocyclyl, or a group selected from X1 to X5
cycle A is aryl or heteroaryl;
cycle B is a saturated or partially unsaturated heterocyclyl;
cycle C is aryl or heteroaryl;
R1, R2, R3, R4, R5, R6 and R8 are independently hydrogen or an organic radical;
R7 is haloalkyl;
G is oxygen or sulfur;
L is O, NH, NR1, CR3R4;
n is 0, 1, 2, 3, 4 or 5;
o is 0, 1, 2, 3, 4 or 5;
p is 1, 2, 3, 4 or 5.

### Claim 2 (depends on 1)

A method according to claim 1, wherein the compound of formula I is a compound of formula IA
wherein P is P0
or P is selected from P1 to P54
G1 is oxygen;
G2 is O or CH2;
L is a bond, methylene or ethylene;
one of A1 and A2 is S, SO or SO2 and the other is —C(R4)R4—;
R3 is hydrogen or methyl;
each R4 is independently hydrogen or methyl;
Y1 is C—R6, CH or nitrogen;
Y2 and Y3 are independently CH or nitrogen;
wherein no more than two of Y1, Y2 and Y3 are nitrogen and wherein Y2 and Y3 are not both nitrogen;
R5 is hydrogen, halogen, cyano, nitro, NH2, C1-C2alkyl, C1-C2haloalkyl, C3-C5cycloalkyl, C3-C5halocycloalkyl, C1-C2alkoxy, C1-C2haloalkoxy;
R6 together with R5 forms a —CH═CH—CH═CH— bridge;
X2 is C—X6 or nitrogen;
X1, X3 and X6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X1, X3 and X6 are not hydrogen;
X4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.

### Claim 3 (depends on 1)

A method according to claim 1, wherein the compound of formula I is a compound of formula IB
wherein —B1-B2-B3— is —C═N—O—, —C═N—CH2—, or —N—CH2—CH2—;
R1 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl;
R2 is group X
X2 is C—X6 or nitrogen;
X1, X3 and X6 are independently hydrogen, halogen or trihalomethyl, wherein at least one of X1, X3 and X6 is not hydrogen;
A is selected from group A1 to A5
Y1 is C—R6, CH or nitrogen;
Y2 and Y3 are independently CH or nitrogen;
wherein no more than two of Y1, Y2 and Y3 are nitrogen and wherein Y2 and Y3 are not both nitrogen;
R5 is hydrogen, halogen, cyano, nitro, NH2, C1-C4alkyl, C1-C4haloalkyl, C3-C5cycloalkyl, C3-C5halocycloalkyl, C1-C2alkoxy, or C1-C2haloalkoxy;
R6 when present together with R5 forms a —CH═CH—CH═CH— bridge;
R7 is C1-C4alkyl;
R8 is C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy(C1-C4)alkyl, C1-C4alkylthio(C1-C4)alkyl, C1-C4alkylsulfinyl(C1-C4)alkyl, C1-C4alkylsulfonyl(C1-C4)alkyl, C3-C6cycloalkyl, C3-C6cycloalkyl(C1-C4)alkyl-, or tetrahydrofuranyl;
R9 is C1-C4alkyl, C1-C4haloalkyl, C1-C4alkyl-O—CH2—, C1-C4haloalkyl-O—CH2—, C3-C6cycloalkyl, or C3-C6cycloalkyl-CH2—, C1-C4alkyl-S—CH2—, C1-C4alkyl-S(O)—CH2—, C1-C4alkyl-S(O2)—CH2;
each Z is independently halogen, C1-C12alkyl or C1-C12alkyl substituted by one to five R12, nitro, C1-C12alkoxy or C1-C12alkoxy substituted by one to five R12, cyano, C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C12haloalkylsulfinyl, C1-C12haloalkylsulfonyl, hydroxyl or thiol;
each R12 is halogen, cyano, nitro, hydroxy, C1-C8alkoxy-, C1-C8haloalkoxy-, mercapto, C1-C8alkylthio-, or C1-C8haloalkylthio; and
k is 0, 1, 2 or 3.

### Claim 4 (depends on 1)

A method according to claim 1, wherein the method is for controlling termites at the location of a termite nest by applying the compound at a location remote from the termite nest.

### Claim 5 (depends on 1)

A method according to claim 1, wherein the compound of formula I is applied as a non-repellent termiticide.

### Claim 6 (depends on 1)

A method according to claim 1, comprising controlling termites at a second location by applying a compound of formula I to a first location, wherein the second location is remote from the first location.

### Claim 7 (depends on 6)

A method according to claim 6, wherein the second location is a termite nest.

### Claim 8 (depends on 1)

A method according to claim 1, wherein the location where termite control is needed or is expected to be needed is treated with a compound of formula I such that the concentration of compound at the location is sufficient to kill termites whilst allowing the termites to carry the compound of formula I away from the location of application.

### Claim 9 (depends on 1)

A method according to claim 1, wherein the compound of formula I is applied as a liquid formulation to soil and wherein the liquid formulation applied to the soil contains less than 1% of the compound of formula I.

### Claim 10 (depends on 1)

A method according to claim 1, wherein the compound of formula I is applied as a liquid formulation to soil and wherein the liquid formulation applied to the soil contains from 0.01 to 1% by weight of the compound of formula I.

### Claim 11 (depends on 1)

A method according to claim 1, wherein the location is a man-made structure or in and/or around the area where the man-made structure is to be located.

### Claim 12 (depends on 11)

A method according to claim 11, wherein the structure is a building.

### Claim 13 (depends on 1)

A method according to claim 1, wherein the liquid formulation is included with a termite bait.

### Claim 14 (depends on 1)

A termite and/or ant bait comprising a compound of formula I as defined in claim 1.

### Claim 15

(canceled)

### Claim 16 (depends on 1)

A method according to claim 1, wherein P is selected from P1, P2 and P55 to P64

### Claim 17 (depends on 1)

A method according to claim 1, wherein P is selected from P2, P56, P57 and P58.

### Claim 18 (depends on 1)

A method according to claim 1, wherein P is P57.

### Claim 19 (depends on 1)

A method according to claim 1, wherein X2 is C—X6, Y1, Y2 and Y3 are C—H, G1 is oxygen, G2 is oxygen, A1 is CH2, A2 is S, SO or SO2, L is a bond, R3 and each R4 is hydrogen, R5 is chloro, bromo, methyl or trifluoro methyl, Y1 is CH, Y2 is CH, and Y3 is CH, X4 is trifluoromethyl.

### Claim 20 (depends on 1)

A method for controlling ants comprising applying a liquid formulation comprising a compound of formula I to a location where ant control is needed or is expected to be needed, wherein the compound of formula I is a compound as defined in claim 1.

### Claim 21 (depends on 20)

A method according to claim 20, wherein the method is for controlling ants at the location of an ant nest by applying the compound at a location remote from the ant nest.

### Claim 22 (depends on 20)

A method according to claim 20, wherein the compound of formula I is applied as a non-repellent formicide.

### Claim 23 (depends on 20)

A method according to claim 20, comprising controlling ants at a second location by applying a compound of formula I to a first location, wherein the second location is remote from the first location.

### Claim 24 (depends on 20)

A method according to claim 20, wherein the location where ant control is needed or is expected to be needed is treated with a compound of formula I such that the concentration of compound at the location is sufficient to kill ants whilst allowing the ants to carry the compound of formula I away from the location of application.

### Claim 25 (depends on 20)

A method according to claim 20, wherein the compound of formula I is applied as a residual liquid formulation comprising a compound of formula I to a surface where ant activity occurs is expected to occur at a rate of up to 500 mg/m2, preferably 25 to 200 mg/m2.

### Claim 26 (depends on 20)

A method according to claim 20, wherein applying is to a man-made structure and/or around the man-made structure.

### Claim 27 (depends on 26)

A method according to claim 26, wherein the man-made structure is a building.

### Claim 28 (depends on 20)

A method according to claim 20, wherein the liquid formulation is included with an ant bait.

### Claim 29

(canceled)

### Claim 30

(canceled)

### Claim 31 (depends on 1, 20)

A method according to claim 20, wherein controlling includes protecting a eucalyptus tree plantation from leaf cutter ants, and wherein applying includes locating a bait comprising the compound of formula I as defined in claim 1 to a location where leaf-cutter ant activity is occurring or is expected to occur.