# US 5,700,460 A · Methods of attracting and combatting insects

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- Number: US 5,700,460 A
- Document ID: US5700460A
- Status: Granted
- Kind: A
- Application number: 08/731,132
- Filed: 1996-10-10
- Granted: 1997-12-23
- Earliest claimed: 1995-04-10
- Assignees: Rhone-Poulenc Inc.
- Inventors: Thomas Charles Davidson; Georgina M. Werner
- Web page: https://patentgrep.com/patent/US5700460A

## CPC

- A01N 47/02: the carbon atom having no bond to a nitrogen atom
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- 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

A method for attracting and controlling insects comprising offering to said insects for ingestion an effective amount of a compound of the formula: ##STR1## wherein the structural variables are as defined in the specification.

## Claims

### Claim 1

A method for attracting insects, said method comprising offering to said insects for ingestion an effective attractant amount of a compound having the formula: ##STR4## wherein R.sub.1 is CN or methyl;
R.sub.2 is --S(O).sub.n R.sub.3 ;
R.sub.3 is alkyl or haloalkyl;
R.sub.4 is hydrogen, halogen, --NR.sub.5 R.sub.6, --S(O).sub.m R.sub.7, alkyl, haloalkyl, --OR.sub.8 or --N=C(R.sub.9)(R.sub.10);
each of R.sub.5 and R.sub.6, which are the same or different, is hydrogen, alkyl, haloalkyl, --C(O)alkyl or --S(O).sub.r CF.sub.3 ; or R.sub.5 and R.sub.6 together form a divalent lower alkylene radical which is optionally interrupted by one or more heteroatoms selected from O, S and N;
R.sub.7 is alkyl or haloalkyl;
R.sub.8 is alkyl, haloalkyl or hydrogen;
R.sub.9 is hydrogen or alkyl;
R.sub.10 is phenyl or heteroaryl, each of which is unsubstituted or is substituted with one or more substituents selected from the group consisting of hydroxy, halogen, --O--alkyl, --S--alkyl, cyano and alkyl;
each of R.sub.11 and R.sub.12, which are the same or different, is halogen or hydrogen;
R.sub.13 is halogen, haloalkyl, haloalkoxy, --S(O).sub.q CF.sub.3 or --SF.sub.5 ;
each of m, n, q and r, which are the same or different, is 0, 1 or 2; and
X is nitrogen or C--R.sub.12 ;
provided that when R.sub.1 is methyl, R.sub.3 is haloalkyl, R.sub.4 is NH.sub.2, R.sub.11 is Cl, R.sub.13 is CF.sub.3, and X is N.

### Claim 2 (depends on 1)

A method according to claim 1, having at least one feature selected from the group consisting of:
(a) R.sub.1 is CN;
(b) R.sub.3 is haloalkyl;
(c) R.sub.4 is NH.sub.2 ;
(d) each of R.sub.11 and R.sub.12, which are the same or different, is halogen; and
(e) R.sub.13 is haloalkyl.

### Claim 3 (depends on 1)

A method according to claim 1, wherein said insects are insects which are able to enter or inhabit buildings.

### Claim 4 (depends on 3)

A method according to claim 3, wherein said compound of formula (I) is offered to said insects as an alternative food source at a locus which is in or near an area in which other food is present.

### Claim 5 (depends on 4)

A method according to claim 4, wherein the food source comprising said compound of formula (I) is in solid, liquid or gel form.

### Claim 6 (depends on 5)

A method according to claim 5, wherein said solid, liquid or gel form is a solid, liquid or gel bait.

### Claim 7 (depends on 1)

A method according to claim 1, wherein said insects belong to the family Blatidae or Formacidae.

### Claim 8 (depends on 4)

A method according to claim 4, wherein said insects are cockroaches.

### Claim 9 (depends on 1)

A method according to claim 1, wherein said insects are American cockroaches (Periplanipa americana) or German cockroaches (Blatella germanica).

### Claim 10 (depends on 6)

A method according to claim 6, wherein said insects are American cockroaches (Periplanipa americana) or German cockroaches (Blatella germanica).

### Claim 11 (depends on 4)

A method according to claim 4, wherein said compound of formula (I) is offered in an mount of from about 0.00001 g to about 20 g per 100 square meters.

### Claim 12 (depends on 11)

A method according to claim 11, wherein said compound of formula (I) is offered in an mount of from about 0.001 g to about 1 g per 100 square meters.

### Claim 13 (depends on 4)

A method according to claim 4, wherein the food source comprising said compound of formula (I) comprises from about 0.001 to about 15 % w/w of compound of formula (I).

### Claim 14 (depends on 13)

A method according to claim 13, wherein the food source comprising said compound of formula (I) comprises from about 0.1 to about 6 % w/w of compound of formula (I).

### Claim 15

A method for attracting and killing insects comprising offering to said insects for ingestion a compound having the formula: ##STR5## wherein: R.sub.1 is CN or methyl;
R.sub.2 is S(O).sub.n R.sub.3 ;
R.sub.3 is alkyl or haloallcyl;
R.sub.4 is hydrogen, halogen, --NR.sub.5 R.sub.6, --S(O).sub.m R.sub.7, alkyl, haloalkyl, --OR.sub.8 or --N=C(R.sub.9)(R.sub.10);
each of R.sub.5 and R.sub.6, which are the same or different, is hydrogen, alkyl, haloalkyl, -C(O)alkyl or -S(O).sub.r CF.sub.3 ; or R.sub.5 and R.sub.6 together form a divalent lower alkylene radical which is optionally interrupted by one or more heteroatoms selected from O, S and N;
R.sub.7 is alkyl or haloalkyl;
R.sub.8 is alkyl, haloalkyl or hydrogen;
R.sub.9 is hydrogen or alkyl;
R.sub.10 is phenyl or heteroaryl, each of which is unsubstituted or is substituted with one or more substituents selected from the group consisting of hydroxy, halogen, --O--alkyl, --S--alkyl, cyano and alkyl;
each of R.sub.11 and R.sub.12, which are the same or different, is halogen or hydrogen;
R.sub.13 is halogen, haloalkyl, haloalkoxy, --S(O).sub.q CF.sub.3 or --SF.sub.5 ;
each of m, n, q and r, which are the same or different, is 0, 1 or 2; and
X is nitrogen or C--R.sub.12 ;
provided that when R.sub.1 is methyl, R.sub.3 is haloalkyl, R.sub.4 is NH.sub.2, R.sub.11 is C.sub.1, R.sub.13 is CF.sub.3, and X is N;
wherein said compound of formula (I) is offered in an amount which is effective both as an attractant and as an insecticide.

### Claim 16 (depends on 15)

A method according to claim 15, having at least one feature selected from the group consisting of:
(a) R.sub.1 is CN;
(b) R.sub.3 is haloalkyl;
(c) R.sub.4 is NH.sub.2 ;
(d) each of R.sub.11 and R.sub.12, which are the same or different, is halogen; and
(e) R.sub.13 is haloalkyl.

### Claim 17 (depends on 15)

A method according to claim 15, wherein said compound of formula (I) is offered to said insects as an alternative food source at a locus which is in or near an area in which other food is offered.

### Claim 18 (depends on 17)

A method according to claim 17, wherein the food source comprising said compound of formula (I) is in solid, liquid or gel form.

### Claim 19 (depends on 18)

A method according to claim 18, wherein said solid, liquid or gel form is a solid, liquid or gel bait.

### Claim 20 (depends on 15)

A method according to claim 15, wherein said insects belong to the family Blatidae or Formacidae.

### Claim 21 (depends on 17)

A method according to claim 17, wherein said insects are cockroaches.

### Claim 22 (depends on 15)

A method according to claim 15, wherein said insects are American cockroaches (Periplanipa americana) or German cockroaches (Blatella germanica).

### Claim 23 (depends on 19)

A method according to claim 19, wherein said insects are American cockroaches (Periplanipa americana) or German cockroaches (Blatella germanica).

### Claim 24 (depends on 15)

A method according to claim 15, wherein said compound of formula (I) is offered in combination with a carrier or surface-active agent.

### Claim 25 (depends on 15)

A method according to claim 15, wherein said compound of formula (I) is offered in combination with another pesticide.

### Claim 26 (depends on 15)

A method according to claim 15, wherein said compound of formula (I) is offered in an amount of from about 0.00001 g to about 20 g per 100 square meters.

### Claim 27 (depends on 26)

A method according to claim 26, wherein said compound of formula (I) is offered in an amount of from about 0.001 g to about 1 g per 100 square meters.

### Claim 28 (depends on 17)

A method according to claim 17, wherein the food source comprising said compound of formula (I) comprises from about 0.001 to about 15 % w/w of compound of formula (I).

### Claim 29 (depends on 28)

A method according to claim 28, wherein the food source comprising said compound of formula (I) comprises from about 0.1 to about 6 % w/w of compound of formula (I).

### Claim 30

A method for controlling a population of insects at a locus which is in or near a food storage, preparation, serving or eating area, said method comprising offering to said insects as an alternative food source an amount of a compound having the formula: ##STR6## wherein: R.sub.1 is CN or methyl;
R.sub.2 is --S(O).sub.n R.sub.3 ;
R.sub.3 is alkyl or haloalkyl;
R.sub.4 is hydrogen, halogen, --NR.sub.5 R.sub.6, --S(O).sub.m R.sub.7, alkyl, haloalkyl, --OR.sub.8 or each of R.sub.5 and R.sub.6, which are the same or different, is hydrogen, alkyl, haloalkyl, --C(O)alkyl or --S(O).sub.r CF.sub.3 ; or R.sub.5 and R.sub.6 together form a divalent lower alkylene radical which is optionally interrupted by one or more heteroatoms selected from O, S and N;
R.sub.7 is alkyl or haloalkyl;
R.sub.8 is alkyl, haloalkyl or hydrogen;
R.sub.9 is hydrogen or alkyl;
R.sub.10 is phenyl or heteroaryl, each of which is unsubstituted or is substituted with one or more substituents selected from the group consisting of hydroxy, halogen, --O--alkyl, --S--alkyl, cyano and alkyl;
each of R.sub.11 and R.sub.12, which are the same or different, is halogen or hydrogen;
R.sub.13 is halogen, haloalkyl, haloalkoxy, --S(O).sub.q CF.sub.3 or --SF.sub.5 ;
each of m, n, q and r, which are the same or different, is 0, 1 or 2; and
X is nitrogen or C--R.sub.12 ;
provided that when R.sub.1 is methyl, R.sub.3 is haloalkyl, R.sub.4 is NH.sub.2, R.sub.11 is Cl, R.sub.13 is CF.sub.3, and X is N;
which is effective both as an attractant and as an insecticide.

### Claim 31 (depends on 30)

A method according to claim 30, having at least one feature selected from the group consisting of:
(a) R.sub.1 is CN;
(b) R.sub.3 is haloalkyl;
(c) R.sub.4 is NH.sub.2 ;
(d) each of R.sub.11 and R.sub.12, which are the same or different, is halogen; and
(e) R.sub.13 is haloalkyl.

### Claim 32 (depends on 30)

A method according to claim 30, wherein the food source comprising said compound of formula (I) is in solid form.

### Claim 33 (depends on 32)

A method according to claim 32, wherein said solid form is a solid bait.

### Claim 34 (depends on 30)

A method according to claim 30, wherein said insects are cockroaches.

### Claim 35 (depends on 30)

A method according to claim 30, wherein said compound of formula (I) is offered in an amount of from about 0.00001 g to about 20 g per 100 square meters.

### Claim 36 (depends on 35)

A method according to claim 35, wherein said compound of formula (I) is offered in an amount of from about 0.001 g to about 1 g per 100 square meters.