# US 7,612,105 B2 · 3-arylphenyl sulfide derivative and insecticide and miticide

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- Number: US 7,612,105 B2
- Document ID: US7612105B2
- Status: Granted
- Kind: B2
- Application number: 11/098,440
- Filed: 2005-04-05
- Published: 2005-08-04
- Granted: 2009-11-03
- Earliest claimed: 1998-04-27
- Assignees: Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.
- Inventors: Keiji Toriyabe; Nobuo Takefuji; Minoru Itou; Tetsuya Hirade; Kiyotoshi Nishiyama; Mitsuharu Asahida; Yasunobu Maeda; Nobuhide Wada; Toyokazu Fujisawa; Hiroyuki Yano; Masaaki Komatsu; Osamu Tada
- Web page: https://patentgrep.com/patent/US7612105B2

## CPC

- C07D 213/12: from unsaturated compounds
- A01N 31/08: Oxygen or sulfur directly attached to an aromatic ring system
- A01N 31/14: Ethers
- A01N 33/10: having at least one oxygen or sulfur atom directly attached to an aromatic ring system
- A01N 37/08: containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
- A01N 37/34: Nitriles
- A01N 41/10: Sulfones; Sulfoxides
- A01N 43/08: with oxygen as the ring hetero atom
- A01N 43/10: with sulfur as the ring hetero atom
- A01N 43/40: six-membered rings
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 47/18: containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- C07C 317/32: with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C 317/48: the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C 323/18: having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C 323/20: with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C 323/36: the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
- C07C 323/63: the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07D 213/32: Sulfur atoms
- C07D 213/48: Aldehydo radicals
- C07D 213/57: Nitriles
- C07D 213/64: attached in position 2 or 6
- C07D 239/36: as doubly bound oxygen atom or as unsubstituted hydroxy radical
- C07D 239/38: One sulfur atom
- C07D 239/40: as doubly bound sulfur atom or as unsubstituted mercapto radical
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D 333/24: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

3-Arylphenyl sulfide derivatives represented by general formula (I): (wherein R is a C2-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group or the like, B0 to B2 and B3 are hydrogen atoms, halogen atoms, cyano groups, C1-C4 haloalkyl groups or the like, n is 0, 1 or 2, and Ar is a phenyl ring, a pyridine ring, a thiophene ring, a pyrazole ring or the like), and insecticides and miticides containing the 3-arylphenyl sulfide derivatives as an active ingredient.

## Claims

### Claim 1

A compound represented by formula (I):
wherein R is
a C2-C6 alkyl group which may be mono- or poly-substituted by halogen atoms or cyano groups,
a C2-C6 alkenyl group which maybe mono- or poly-substituted by halogen atoms or cyano groups,
a C2-C6 alkynyl group which may be mono- or poly-substituted by halogen atoms or cyano groups,
a C3-C6 cycloalkyl group which may be mono- or poly-substituted by halogen atoms or cyano groups or
a C4-C9 cycloalkylalkyl group, which may be mono- or poly-substituted by halogen atoms or cyano groups, and
n is an integer of from 0 to 2;
Ar is a group represented by formula (Ar-1):
wherein Q1, Q2, Q3, Q4 and Q5 are, respectively, a nitrogen atom or C-A1, a nitrogen atom or C-A2, a nitrogen atom or C-A3, a nitrogen atom or C-A4, and a nitrogen atom or C-A5, with the proviso that one of Q1-Q5 is a nitrogen atom, and
A1, A5, and B0 are selected from the group consisting of a hydrogen atom, a halogen atom, an amino group, a cyano group, a nitro group, a C1-C6 alkyl group, a C1-C4 haloalkyl group, a C1-C6 alkylthio group, which may be mono- or poly-substituted by halogen atoms, or a C1-C6 alkoxy group; and
A2, A3, A4, B1, B2 and B3 are selected from the group consisting of
a hydrogen atom, a halogen atom, a cyano group, a nitro group,
a C1-C6 alkyl group, which may be mono- or poly-substituted by halogen atoms, hydroxyl groups, cyano groups, C2-C7 alkoxycarbonyl groups or C1-C6 alkoxy groups,
a C2-C6 alkenyl group, which may be mono- or poly-substituted by halogen atoms or cyano groups,
a C2-C6 alkynyl group, which may be mono- or poly-substituted by halogen atoms or cyano groups,
a C1-C6 alkoxy group, which may be mono- or poly-substituted by halogen atoms, cyano groups, C2-C5 alkoxycarbonyl groups or C1-C3 alkoxy groups,
a C1-C6 alkylthio group, which may be mono- or poly-substituted by halogen atoms or C1-C3 alkoxy groups,
a C1-C6 alkylsulfinyl group, which may be mono- or poly-substituted by halogen atoms or C1-C3 alkoxy groups,
a C1-C6 alkylsulfonyl group which may be mono- or poly-substituted by halogen atoms or C1-C3 alkoxy groups,
a C1-C7 acyl group, a C2-C5 haloalkylcarbonyl group, a carboxyl group, and a C2-C7 alkoxycarbonyl group or
NR1R2, wherein R1 and R2 are independently a hydrogen atom,
a C1-C6 alkyl group which may be mono- or poly-substituted by halogen atoms, cyano groups, hydroxyl groups, C1-C6 alkoxy groups or C1-C6 alkylthio groups,
a C2-C6 alkenyl group, which may be mono- or poly-substituted by halogen atoms or cyano groups,
a C2-C6 alkynyl group, which may be mono- or poly-substituted by halogen atoms or cyano groups,
a C1-C7 acyl group, or
a C2-C7 alkoxycarbonyl group,
or may form a 5 to 6-membered ring together with the nitrogen atom attached thereto.

### Claim 2 (depends on 1)

The compound of claim 1, wherein B0 is hydrogen.

### Claim 3 (depends on 1)

The compound of claim 1, wherein B0 is not hydrogen.

### Claim 4 (depends on 1)

The compound of claim 1, wherein B1 is hydrogen.

### Claim 5 (depends on 1)

The compound of claim 1, wherein B2 is CN.

### Claim 6 (depends on 1)

The compound of claim 1, wherein B2 is not CN.

### Claim 7 (depends on 1)

The compound of claim 1, wherein B2 is methyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein B2 is selected from the group consisting of —CHO, Cl, and —CHF2.

### Claim 9 (depends on 1)

The compound of claim 1, wherein n is 0.

### Claim 10 (depends on 1)

The compound of claim 1, wherein n is 1.

### Claim 11 (depends on 1)

The compound of claim 1, wherein n is 2.

### Claim 12 (depends on 1)

The compound of claim 1, wherein R is unsubstituted with halogen.

### Claim 13 (depends on 1)

The compound of claim 1, wherein R is polysubstituted with halogen atoms.

### Claim 14 (depends on 1)

The compound of claim 1, wherein R is selected from the group consisting of ethyl, n-propyl, i-propyl, cyclopropylmethyl, and 2,2,2-trifluoroethyl.

### Claim 15 (depends on 1)

The compound of claim 1, wherein Ar is (Ar-1) and Q4 is N.

### Claim 16 (depends on 15)

The compound of claim 15, wherein each of Q1, Q2, and Q5 is C—H and Q3 is C—CF3.

### Claim 17 (depends on 1)

The compound of claim 1, wherein each of Q1, Q2, and Q5 is C—H and Q3 is C—Cl.

### Claim 18 (depends on 1)

The compound of claim 1, wherein Ar is (Ar-1) and Q5 is nitrogen.

### Claim 19 (depends on 18)

The compound of claim 18, wherein each of Q1, Q2, Q3, and Q4 is C—H.

### Claim 20 (depends on 18)

The compound of claim 18, wherein both Q1 and Q4 is C—H and each of Q2 and Q3 is C—H or C—CF3.

### Claim 21 (depends on 1)

A composition comprising the compound of claim 1 and one or more compound(s) selected from the group consisting of an adjuvant, surfactant and carrier.

### Claim 22 (depends on 1)

A composition comprising the compound of claim 1 and one or more compound(s) selected from the group consisting of a fertilizer or plant growth regulator.

### Claim 23 (depends on 1)

A composition comprising the compound of claim 1 and one or more compound(s) selected from the group consisting of an antivirus agent or a fungicide.

### Claim 24 (depends on 1)

A composition comprising the compound of claim 1 and one or more compound(s) selected from the group consisting of an attractant, insecticide, miticide and a nematacide.

### Claim 25 (depends on 1)

A composition comprising the compound of claim 1 and one or more herbicide(s).

### Claim 26 (depends on 1)

A method of controlling or killing a mite comprising contacting said mite with an effective amount of the compound of claim 1.

### Claim 27 (depends on 1)

A method of controlling or killing a lepidopteran comprising contacting said lepidopteran with an effective amount of the compound of claim 1.

### Claim 28 (depends on 1)

A method of controlling or killing a hemipteran comprising contacting said hemipteran with an effective amount of the compound of claim 1.

### Claim 29 (depends on 1)

A method of controlling or killing a dipteran comprising contacting said dipteran with an effective amount of the compound of claim 1.

### Claim 30 (depends on 1)

A method of controlling or killing a hymenopteran comprising contacting said hymenopteran with an effective amount of sulfide compound of claim 1.

### Claim 31 (depends on 1)

A method of controlling or killing a orthopteran comprising contacting said orthopteran with an effective amount of the compound of claim 1.

### Claim 32 (depends on 1)

A method of controlling or killing a isopteran comprising contacting said isopteran with an effective amount of the compound of claim 1.