# US 2017/0283405 A1 · Pyrazoline derivatives as insecticidal compounds

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- Number: US 2017/0283405 A1
- Document ID: US20170283405A1
- Status: Published application
- Kind: A1
- Application number: 15/628,804
- Filed: 2017-06-21
- Published: 2017-10-05
- Earliest claimed: 2013-01-23
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Long Lu; Jerome Yves Cassayre; Guillaume Berthon; Myriem El Qacemi; Yaming Wu
- Web page: https://patentgrep.com/patent/US20170283405A1

## CPC

- C07D 413/12: linked by a chain containing hetero atoms as chain links
- A01N 43/16: with oxygen as the ring hetero atom
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- 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 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 53/00: Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- C07D 231/06: having one double bond between ring members or between a ring member and a non-ring member
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- 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

The present invention relates to compounds of formula I wherein P is selected from P1 and P2, or P and R5 together are P3 or P is a heterocycle H, selected from H1 to H9 wherein Y1, Y2, and Y3 are independently of each other C—H, C—R5, or nitrogen; and G1, G2, G3, Z, R1, R2, R3, R4, R5, R6a, R6b, R7, R8, R9, R10, R11, p, n and k are as defined in the claims. The invention also relates to methods of controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I.

## Claims

### Claim 1 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10)

A compound of formula Int-I
wherein Y1, Y2, Y3, G1, R3, R4, R5 are as defined for compounds of formula I in any one of claims 1 to 10, and R is hydroxy, C1-C15alkoxy or halogen; or a salt or N-oxide thereof; or
a compound of formula Int-II
wherein Y1, Y2, Y3, R3, R4, R5, R6a and R6b are as defined for compounds of formula I in any one of claims 1 to 10 and Ra and Rb are independently selected from hydrogen, C1-C8carbonyl, C1-C8alkoxycarbonyl, or Ra and Rb together are —C(═O)—(CH2)r—C(═O)— wherein r is 1 to 4, —C(C1-C3alkyl)=C—C═(C1-C3alkyl)C—, or group D
or a salt or N-oxide thereof; or
a compound of formula Int-III
wherein Y1, Y2, Y3, R3, R4, R11 and n are as defined for compounds of formula I in any one of claims 1 to 10 and Ra and Rb, are as defined for the compounds of formula Int-II, or a salt or N-oxide thereof; or
a compound of formula Int-IV
wherein R3 and R4 are as defined for compounds of formula I in any one of claims 1 to 10, and Rc is hydrogenor a salt or N-oxide thereof; or
a compound of formula Int-V
wherein R3 and R4 are as defined for compounds of formula I in any one of claims 1 to 10, or a salt or N-oxide thereof.

### Claim 2

A method of controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I)
wherein
P is selected from P1 and P2, or P and R5 together are P3
or P is a heterocycle H, selected from H1 to H9
Y1, Y2, and Y3 are independently of each other C—H, C—R5, or nitrogen;
G1 is oxygen or sulfur;
G2 is oxygen or sulfur;
G3 is oxygen or sulfur;
R1 is hydrogen, C1-C8alkyl, C1-C8alkoxy, C1-C8alkylcarbonyl, or C1-C8alkoxycarbonyl;
R2 is C1-C8alkyl or C1-C8alkyl substituted by one to five R12, C3-C10cycloalkyl or C3-C10cycloalkyl substituted by one to five R13, C3-C10cycloalkyl-C1-C4alkylene or C3-C10cycloalkyl-C1-C4alkylene substituted by one to five R13, aryl-C1-C4alkylene- or aryl-C1-C4alkylene- substituted by one to five R14, heterocyclyl-C1-C4alkylene- or heterocyclyl-C1-C4alkylene- substituted by one to five R14, aryl or aryl substituted by one to five R14, heterocyclyl or heterocyclyl substituted by one to five R14, C1-C8alkylaminocarbonyl-C1-C4alkylene, C1-C8haloalkylaminocarbonyl-C1-C4alkylene, C3-C8cycloalkyl-aminocarbonyl-C1-C4 alkylene, aryl-CH2-aminocarbonyl-C1-C4alkylene or aryl-CH2-aminocarbonyl-C1-C4alkylene wherein the aryl is substituted by one to five R14, C1-C8alkylaminocarbonyl, C1-C8haloalkylaminocarbonyl, C3-C6cycloalkylaminocarbonyl, C1-C6alkyl-O—N═CH—, or C1-C6haloalkyl-O—N═CH—;
R3 is C1-C8haloalkyl;
R4 is aryl or aryl substituted by one to five R15, or heteroaryl or heteroaryl substituted by one to five R15;
each R5 is independently hydrogen, halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, C3-C10cycloalkyl, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, or C1-C8haloalkylsulfonyl, or two R5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;
R6a and R6b are each independently hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, or C3-C8cycloalkyl, or R6a and R6b together with the carbon atom to which they are attached may form a 3 to 6-membered carbocyclic ring;
R7 is hydrogen, C1-C8alkyl, C1-C8alkoxy, C1-C8alkylcarbonyl, or C1-C8alkoxycarbonyl;
R8 is C1-C8alkyl or C1-C8alkyl substituted by one to five R12, C3-C10cycloalkyl or C3-C10cycloalkyl substituted by one to five R13, C3-C10cycloalkyl-C1-C4alkylene or C3-C10cycloalkyl-C1-C4alkylene substituted by one to five R13, aryl-C1-C4alkylene- or aryl-C1-C4alkylene- substituted by one to five R14, heterocyclyl-C1-C4alkylene- or heterocyclyl-C1-C4alkylene- substituted by one to five R14, aryl or aryl substituted by one to five R14, or heterocyclyl or heterocyclyl substituted by one to five R14,
each R9 is independently hydrogen, C1-C8alkyl, C1-C8alkoxy, C1-C8alkylcarbonyl, or C1-C8alkoxycarbonyl;
R10 is C1-C8alkyl or C1-C8alkyl substituted by one to five R12, C3-C10cycloalkyl or C3-C10cycloalkyl substituted by one to five R13, C3-C10cycloalkyl-C1-C4alkylene or C3-C10cycloalkyl-C1-C4alkylene substituted by one to five R13, aryl-C1-C4alkylene- or aryl-C1-C4alkylene- substituted by one to five R14, heterocyclyl-C1-C4alkylene- or heterocyclyl-C1-C4alkylene- substituted by one to five R14, aryl or aryl substituted by one to five R14, heterocyclyl or heterocyclyl substituted by one to five R14;
each R11 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, hydroxy, C1-C8alkoxy, C1-C8haloalkoxy, mercapto, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylsulfonyl, C1-C8alkylcarbonyl, or C1-C8alkoxycarbonyl;
each R12 is independently halogen, cyano, nitro, hydroxy, amino, C1-C8alkylamino, (C1-C8alkyl)2amino, C1-C8alkylcarbonylamino, C1-C8haloalkylcarbonylamino, C1-C8alkoxy, C1-C8haloalkoxy, aryloxy or aryloxy substituted by one to five R16, aryloxy-C1-C4alkylene or aryloxy-C1-C4alkylene wherein the aryl moiety is substituted by one to five R16, C1-C8alkylcarbonyl, C1-C8alkoxycarbonyl, mercapto, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylsulfonyl, aryl-C1-C4alkylthio or aryl-C1-C4alkylthio wherein the aryl moiety is substituted by one to five R16;
each R13 is independently halogen, cyano, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, or C1-C8alkoxy, C1-C8akoxycarbonyl, or two R13 are together R19—O—N═;
each R14 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8cyanoalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, C3-C10cycloalkyl, C3-C10cycloalkyl-C1-C4alkylene, hydroxy, C1-C8alkoxy, C1-C8haloalkoxy, mercapto, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylsulfonyl, C1-C8alkylaminosulfonyl, (C1-C8alkyl)2aminosulfonyl, C1-C8alkylcarbonyl, C1-C8haloalkylcarbonyl, C1-C8alkoxycarbonyl, C8haloalkoxycarbonyl, aryl or aryl substituted by one to five R16, heterocyclyl or heterocyclyl substituted by one to five R16, aryl-C1-C4alkylene or aryl-C1-C4alkylene wherein the aryl moiety is substituted by one to five R16, heterocyclyl-C1-C4alkylene or heterocyclyl-C1-C4alkylene wherein the heterocyclyl moiety is substituted by one to five R16, aryloxy or aryloxy substituted by one to five R16, or aryloxy-C1-C4alkylene or aryloxy-C1-C4alkylene wherein the aryl moiety is substituted by one to five R16 or two R14 are together ═O;
each R15 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, hydroxy, C1-C8alkoxy, C1-C8haloalkoxy, mercapto, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylsulfonyl, C1-C8alkylcarbonyl, or C1-C8alkoxycarbonyl;
each R16 is independently halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, or C1-C4haloalkoxy;
each R19 is hydrogen, C1-C8alkyl or C1-C8haloalkyl;
each Z is independently halogen, cyano, C1-C8alkyl or C1-C8alkyl substituted by one to five R12, nitro, hydroxyl, C1-C8alkoxy, C1-C8haloalkoxy, mercapto, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, or C1-C8haloalkylsulfonyl;
k is 0, 1, or 2;
n is 1 or 2;
p is 0, 1, 2, 3, 4, or 5;
or a salt or N-oxide thereof.