# US 7,608,631 B2 · 4-(3,3-dihalo-allyloxy) phenol derivatives having pesticidal properties

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- Number: US 7,608,631 B2
- Document ID: US7608631B2
- Status: Granted
- Kind: B2
- Application number: 10/525,891
- Filed: 2003-08-29
- Published: 2005-12-29
- Granted: 2009-10-27
- Earliest claimed: 2002-08-30
- Assignees: Syngenta Crop Protection AG
- Inventors: Wemer Zambach; Arthur Steiger; Peter Renold; Stephan Trah; Roger Graham Hall
- Web page: https://patentgrep.com/patent/US7608631B2

## CPC

- C07D 207/325: with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- A01N 43/36: five-membered rings
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/713: having rings with four or more nitrogen atoms as the only ring hetero atoms
- A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 47/18: containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- A01N 47/20: N-Aryl derivatives thereof
- C07D 207/333: Radicals substituted by oxygen or sulfur atoms
- C07D 207/34: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 231/22: with aryl radicals attached to ring nitrogen atoms
- C07D 231/38: Nitrogen atoms (nitro radicals C07D231/16)
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D 249/10: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 257/04: Five-membered rings
- C07D 261/08: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 261/10: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 261/18: Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
- C07D 263/32: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 263/34: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D 271/07: with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D 277/24: Radicals substituted by oxygen atoms
- C07D 277/30: 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 277/40: Unsubstituted amino or imino radicals
- C07D 277/48: by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
- C07D 277/56: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 285/08: 1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
- C07D 285/12: 1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D 333/16: by oxygen atoms
- C07D 333/38: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 471/04: Ortho-condensed systems
- 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

## Abstract

Compounds of formula (I) wherein Ao is a bond or a C1-C6alkylene bridge; A1, A2 and A3 are a C1-C6alkylene bridge; D is CH or N; W is, for example, O, S, SO, S02, —C(═O)—O— or —O—C(═O)—; T is a bond or, for example, O, NH, S, SO or SR2; Q is, for example, O, S, SO or SO2; Y is, for example, O, S, SO or SO2; X1 and X2 are each independently of the other fluorine, chlorine or bromine; R1, R2 and R3 are, for example, H, halogen, OH, SH, CN or nitro; R4 is, for example, H, halogen, OH, SH, CN, nitro or C1-C6alkyl; R5 is, for example, H, CN, OH, C1-C6alkyl or C3-C8cycloalkyl; k is 1, 2 or 3 when D is nitrogen; or is 1, 2, 3 or 4 when D is CH; m is 1 or 2; E is heteroaryl which is unsubstituted or substituted—depending upon the substitutions possible on the ring—by from one to four identical or different substituents selected from R10; and R10 is, for example, halogen, CN, NO2, OH, SH or C1-C6alkyl; and, where applicable, their possible E/Z isomers, E/Z isomeric mixtures and/or tautomers, in each case in free form or in salt form, a process for the preparation of those compounds and their use, pesticidal compositions in which the active ingredient has been selected from those compounds or an agrochemically acceptable salt thereof, a process for the preparation of those compositions and their use, plant propagation material treated with those compositions, and a method of controlling pests.

## Claims

### Claim 1

A compound of formula
wherein
A0, A1 and A2 are each independently of the other a bond or a C1-C6alkylene group which is unsubstituted or substituted by from one to six identical or different substituents selected from C3-C8cycloalkyl, C3-C8cycloalkyl-C1-C6alkyl and C1-C3haloalkyl;
A3 is a C1-C6alkylene group which is unsubstituted or substituted by from one to six identical or different substituents selected from C3-C8cycloalkyl, C3-C8cycloalkyl-C1-C6alkyl and C1-C3haloalkyl;
D is CH;
X1 and X2 are each independently of the other fluorine, chlorine or bromine;
R1, R2 and R3 are each independently of the others H, halogen, OH, SH, CN, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, —S(═O)—C1-C6alkyl, —S(O)2—C1-C6alkyl, C1-C6alkoxycarbonyl or C3-C6haloalkynyloxy; the substituents R3 being independent of one another when m is 2;
R4 is H, halogen, OH, SH, CN, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C2-C6-alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, —S(═O)—C1-C6alkyl, —S(═O)2—C1-C6alkyl or C1-C6alkoxycarbonyl; the substituents R4 being independent of one another when k is greater than 1; or N(R5)2 wherein the two substituents R5 are independent of one another;
R5 is H, CN, OH, C1-C6alkyl, C3-C8cycloalkyl, C3-C8cycloalkyl-C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, —C(═O)R8, —C(═S)R8, phenyl, benzyl; or phenyl or benzyl each of which is substituted in the aromatic ring by from one to five identical or different substituents selected from the group consisting of halogen, C1-C6alkyl, halo-C1-C6alkyl, C1-C6alkoxy, halo-C1-C6-alkoxy, hydroxy, cyano and nitro;
or the two substituents R5 together form a four- to eight-membered, straight-chain or branched alkylene bridge wherein a CH2 group may have been replaced by O, S or NR9, and the alkylene bridge is unsubstituted or substituted by from one to four identical or different substituents selected from C3-C8cycloalkyl, C3-C8cycloalkyl-C1-C6alkyl and C1-C3haloalkyl;
W is O, NR6, S, SO, SO2, —C(═O)—O—, —O—C(═O)—, —C(═O)—NR7— or —NR7—C(═O)—;
T is a bond;
Q is O, NR6, S, SO or SO2;
Y is O, NR6, S, SO or SO2;
R6 and R7 are independently of each other H, C1-C6alkyl, C1-C3haloalkyl, C1-C6alkylcarbonyl, C1-C3haloalkylcarbonyl, C1-C6alkoxyalkyl, C3-C8cycloalkyl or benzyl;
R8 is C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, C3-C6cycloalkyl, phenyl, benzyl; or phenyl or benzyl each of which is unsubstituted or substituted by from one to three identical or different substituents selected from halogen, CN, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkoxycarbonyl, C1-C3haloalkoxycarbonyl and C2-C6haloalkenyloxy;
R9 is H, C1-C6alkyl, C1-C3haloalkyl, C1-C6-alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxyalkyl, C3-C8cycloalkyl or benzyl;
k is 1, 2, 3 or 4 when D is CH;
m is 1 or 2;
E is 1,2,4-oxadiazol-3-yl which is unsubstituted or monosubstituted by CN, halogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6cycloalkyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl or by C1-C6alkoxycarbonyl;
and, where applicable, their possible E/Z isomers, E/Z isomeric mixtures and/or tautomers, in each case in free form or in salt form.

### Claim 2 (depends on 1)

The compound according to claim 1 of formula (I) in free form.

### Claim 3 (depends on 1)

The compound according to claim 1, of formula (I), wherein X1 and X2 are chlorine or bromine.

### Claim 4 (depends on 1)

A pesticidal composition which comprises as active ingredient at least one compound according to claim 1 of formula (I), in free form or in agrochemically acceptable salt form, and at least one adjuvant.

### Claim 5 (depends on 4)

A process for the preparation of a composition as described in claim 4, which comprises mixing the active ingredient with the adjuvant(s).

### Claim 6 (depends on 4)

A method of controlling pests, which comprises applying a pesticidal composition as described in claim 4 to the pests or to the locus thereof.