# US 8,541,473 B2 · 3-aminoxalyl-aminobenzamide derivatives and insecticidal and miticidal agents containing same as active ingredient

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- Number: US 8,541,473 B2
- Document ID: US8541473B2
- Status: Granted
- Kind: B2
- Application number: 13/148,159
- Filed: 2010-02-05
- Published: 2012-01-26
- Granted: 2013-09-24
- Earliest claimed: 2009-02-06
- Assignees: Agro-Kanesho Co., Ltd.
- Applicants: Shuichi Usui; Toshiki Fukuchi; Sachiko Kinoshita
- Inventors: Shuichi Usui; Toshiki Fukuchi; Sachiko Kinoshita
- Web page: https://patentgrep.com/patent/US8541473B2

## CPC

- C07C 237/42: having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
- A01N 37/46: N-acyl derivatives
- C07C 2601/02: with a three-membered ring
- C07C 2601/04: with a four-membered ring
- C07C 2601/08: the ring being saturated
- C07C 2601/14: The ring being saturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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 3-aminooxalylaminobenzamide compound is used as an insecticide or miticide. The 3-aminooxalylaminobenzamide compound is represented by formula [1]: in which, for instance, R1 and R2 each represent a C1 to C3 alkoxy group or a C1 to C3 haloalkoxy group; R3 and R4 each represent a C1 to C8 alkyl group or a C1 to C8 haloalkyl group; R5 represents a C1 to C5 haloalkyl group; R6 and R7 each represent a hydrogen atom or a C1 to C5 alkyl group; Y represents a hydrogen atom or a halogen atom; Z represents a hydrogen atom; n is an integer ranging from 0 to 4; and m is an integer ranging from 0 to 2.

## Claims

### Claim 1

A 3-aminoxalylaminobenzamide compound of formula [1]:
wherein
R1 and R2 are each independently a hydrogen atom, a C1 to C3 alkoxy group, a C1 to C3 haloalkoxy group, a halogen atom or a C1 to C5 alkyl group;
R3 and R4 are each independently a hydrogen atom, a C1 to C8 alkyl group, a C1 to C8 haloalkyl group, an allyl group, a C3 to C8 cycloalkyl group or a C3 to C6 cycloalkyl C1 to C4 alkyl group, provided that R3 and R4 may be bonded together to form a C3 to C8 alkylene bond;
R5 is a C1 to C5 haloalkyl group;
R6 and R7 are each independently a hydrogen atom, a C1 to C5 alkyl group, a C3 to C8 cycloalkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkoxy C1 to C4 alkyl group, a C2 to C6 alkenyl group, a C2 to C6 haloalkenyl group, a C1 to C4 alkylcarbonyl group, a C1 to C4 haloalkylcarbonyl group, a C1 to C4 alkylsulfonyl group, a C1 to C4 haloalkylsulfonyl group, a C1 to C3 alkoxycarbonyl group or a C1 to C3 haloalkoxy carbonyl group;
Y is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C1 to C5 alkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkylamino group, a di-(C1 to C3)alkylamino group, a C1 to C3 alkoxy group or a C1 to C3 haloalkoxy group;
Z is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C1 to C5 alkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkoxy group or a C1 to C3 haloalkoxy group;
n is an integer of from 0 to 4; and
m is an integer of from 0 to 2.

### Claim 2 (depends on 1)

The 3-aminoxalylaminobenzamide compound of claim 1, wherein R1 and R2 are each independently a C1 to C3 alkoxy group, a C1 to C3 haloalkoxy group, a halogen atom or a C1 to C5 alkyl group;
R3 and R4 are each independently a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, an allyl group, a C3 to C6 cycloalkyl group or a C3 to C6 cycloalkyl C1 to C4 alkyl group, provided that R3 and R4 may be bonded together to form a C3 to C6 alkylene bond;
R6 and R7 are each independently a hydrogen atom or a C1 to C5 alkyl group;
Y is a hydrogen atom, a halogen atom, a cyano group, a C1 to C3 alkyl group or a C1 to C3 haloalkyl group; and
Z is a hydrogen atom, a halogen atom or a C1 to C3 alkyl group.

### Claim 3 (depends on 2)

The 3-aminoxalylaminobenzamide compound of claim 2, wherein R1 is a methoxy group, a trifluoromethoxy group, a methyl group, an ethyl group or an isopropyl group; and R2 is a chlorine atom, a bromine atom, an iodine atom, a methyl group or an ethyl group.

### Claim 4 (depends on 2)

The 3-aminoxalylaminobenzamide compound of claim 2, wherein R3 is a methyl group or an ethyl group and R4 is a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, an allyl group, a C3 to C6 cycloalkyl group or a C3 to C6 cycloalkyl C1 to C4 alkyl group, provided that R3 and R4 may be bonded together to form a C3 to C6 alkylene bond.

### Claim 5 (depends on 1)

A method for preparing a compound of claim 1, the method comprising reacting a compound of formula [4]:
wherein
R1 and R2 are each independently a hydrogen atom, a C1 to C3 alkoxy group, a C1 to C3 haloalkoxy group, a halogen atom or a C1 to C5 alkyl group;
R5 is a C1 to C5 haloalkyl group;
R6 and R7 are each independently a hydrogen atom, a C1 to C5 alkyl group, a C3 to C8 cycloalkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkoxy C1 to C4 alkyl group, a C2 to C6 alkenyl group, a C1 to C6 haloalkenyl group, a C1 to C4 alkylcarbonyl group, a C1 to C4 haloalkylcarbonyl group, a C1 to C4 alkylsulfonyl group, a C1 to C4 haloalkylsulfonyl group, a C1 to C3 alkoxycarbonyl group or a C1 to C3 haloalkoxy carbonyl group;
R8 is a lower alkyl group;
Y is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C1 to C5 alkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkylamino group, a di-(C1 to C3)alkylamino group, a C1 to C3 alkoxy group or a C1 to C1 haloalkoxy group;
Z is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C1 to C5 alkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkoxy group or a C1 to haloalkoxy group;
n is an integer of from 0 to 4; and
m is an integer of from 0 to 2,
with a compound of formula [5]:
wherein R3 and R4 are each independently a hydrogen atom, a C1 to C8 alkyl group, a C1 to C8 haloalkyl group, an allyl group, a C3 to C8 cycloalkyl group or a C3 to C6 cycloalkyl C1 to C4 alkyl group, provided that R3 and R4 may be bonded together to form a C3 to C8 alkylene bond.

### Claim 6 (depends on 1)

A method for preparing a compound of claim 1, the method comprising reacting a compound of formula [3]:
wherein
R1 and R2 are each independently a hydrogen atom, a C1 to C3 alkoxy group, a C1 to C3 haloalkoxy group, a halogen atom or a C1 to C5 alkyl group;
R5 is a C1 to C5 haloalkyl group;
R6 and R7 are each independently a hydrogen atom, a C1 to C5 alkyl group, a C3 to C8 cycloalkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkoxy C1 to C4 alkyl group, a C1 to C6 alkenyl group, a C1 to C6 haloalkenyl group, a C1 to C4 alkylcarbonyl group, a C1 to C4 haloalkylcarbonyl group, a C1 to C4 alkylsulfonyl group, a C1 to C4 haloalkylsulfonyl group, a C1 to C3 alkoxycarbonyl group or a C1 to C3 haloalkoxy carbonyl group;
Y is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C1 to C5 alkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkylamino group, a di-(C1 to C3)alkylamino group, a C1 to C3 alkoxy group or a C1 to C3 haloalkoxy group;
Z is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C1 to C5 alkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkoxy group or a C1 to C3 haloalkoxy group;
n is an integer of from 0 to 4; and
m is an integer of from 0 to 2,
with a compound of formula [6]:
wherein R3 and R4 are each independently a hydrogen atom, a C1 to C8 alkyl group, a C1 to C8 haloalkyl group, an allyl group, a C3 to C8 cycloalkyl group or a C3 to C6 cycloalkyl C1 to C4 alkyl group, provided that R3 and R4 may be bonded together to form a C3 to C8 alkylene bond.

### Claim 7 (depends on 1)

A method for preparing a compound of claim 1, the method comprising the step of reacting a compound of formula [3]:
wherein
R1 and R2 are each independently a hydrogen atom, a C1 to C3 alkoxy group, a C1 to C3 haloalkoxy group, a halogen atom or a C1 to C5 alkyl group;
R5 is a C1 to C5 haloalkyl group;
R6 and R7 are each independently a hydrogen atom, a C1 to C5 alkyl group, a C3 to C8 cycloalkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkoxy C1 to C4 alkyl group, a C2 to C6 alkenyl group, a C9 to C6 haloalkenyl group, a C1 to C4 alkylcarbonyl group, a C1 to C4 haloalkylcarbonyl group, a C1 to C4 alkylsulfonyl group, a C1 to C4 haloalkylsulfonyl group, a C1 to C3 alkoxycarbonyl group or a C1 to C3 haloalkoxy carbonyl group;
Y is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C1 to C5 alkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkylamino group, a di-(C1 to C3)alkylamino group, a C1 to C3 alkoxy group or a C1 to C3 haloalkoxy group;
Z is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C1 to C5 alkyl group, a C1 to C5 haloalkyl group, a C1 to C3 alkoxy group or a C1 to C3 haloalkoxy group;
n is an integer of from 0 to 4; and
m is an integer of from 0 to 2,
with a compound of formula [7]:
wherein R3 and R4 are each independently a hydrogen atom, a C1 to C8 alkyl group, a C1 to C8 haloalkyl group, an allyl group, a C3 to C8 cycloalkyl group or a C3 to C6 cycloalkyl C1 to C4 alkyl group, provided that R3 and R4 may be bonded together to form a C3 to C8 alkylene bond; and
X is a halogen atom.

### Claim 8 (depends on 1, 2, 3, 4)

An insecticidal agent or a miticidal agent comprising, as an active ingredient, a 3-aminoxalylaminobenzamide compound as in any one of claims 1 to 4.