Dihydrothiophene derivatives as insecticidal compounds

Patent metadata

Field	Value
Publication number	US-10517294-B2
Application number	US-201314441304-A
Country	US
Kind code	B2
Filing date	Nov 8, 2013
Priority date	Nov 9, 2012
Publication date	Dec 31, 2019
Grant date	Dec 31, 2019

Abstract

The present invention provides compounds of formula (I) wherein Q is Q1 or Q2 P is P0, heterocyclyl or heterocyclyl substituted by one to five Z; Y 1 , Y 2 , Y 3 and Y 4 are independently of each other C—H, C—R 5 , or nitrogen; G 1 is oxygen or sulfur; R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy-, C 1 -C 8 alkylcarbonyl-, or C 1 -C 8 alkoxycarbonyl-; X 4 is C 1 -C 8 haloalkyl; R 4 is aryl or aryl substituted by one to five R 9 , or heteroaryl or heteroaryl substituted by one to five R 9 ; n is 0, 1 or 2; and Z, R 2 , R 5 and R 9 are as defined in the claims. The invention also provides methods of controlling insects, acarines, nematodes or molluscs comprising 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).

First claim

The invention claimed is:

1. A compound of formula (I)

wherein Q is Q1 or Q2

wherein
P is P0, heterocyclyl or heterocyclyl substituted by one to five Z;

Y 2 , Y 3 and Y are independently of each other C—H, C—R 5 , or nitrogen;
G 1 is oxygen or sulfur;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy-, C 1 -C 8 alkylcarbonyl-, or C 1 -C 8 alkoxycarbonyl-;
R 2 is C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 6 , C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to five R 6 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 6 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 7 , C 3 -C 10 cycloalkyl-C 1 -C 4 alkanediyl or C 3 -C 10 cycloalkyl-C 1 -C 4 alkanediyl substituted by one to five R 7 , C 3 -C 10 cycloalkenyl or C 3 -C 10 cycloalkenyl substituted by one to five R 7 , C 3 -C 10 cycloalkenyl-C 1 -C 4 alkanediyl or C 3 -C 3 -C 10 cycloalkenyl-C 1 -C 4 alkanediyl substituted by one to five R 7 , aryl-C 1 -C 4 alkanediyl or aryl-C 1 -C 4 alkanediyl in which the aryl moiety is substituted by one to five R 8 , heterocyclyl-C 1 -C 4 alkanediyl or heterocyclyl-C 1 -C 4 alkanediyl in which the heterocyclyl moiety is substituted by one to five R 8 , aryl-N(R 20 )— or aryl-N(R 20 )— in which the aryl moiety is substituted by one to five R 8 , heterocyclyl-N(R 20 )— or heterocyclyl-N(R 20 )— in which the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , C 1 -C 8 alkylaminocarbonyl-C 1 -C 4 alkanediyl, C 1 -C 8 haloalkylaminocarbonyl-C 1 -C 4 alkanediyl, C 3 -C 8 cycloalkyl-aminocarbonyl-C 1 -C 4 alkanediyl, C 1 -C 8 alkylaminocarbonyl-, C 1 -C 8 haloalkylaminocarbonyl, C 3 -C 8 cycloalkyl-aminocarbonyl, C 1 -C 8 alkyl-O—N═CH—, or C 1 -C 6 haloalkyl-O—N═CH—, and in which a bridging alkanediyl moiety optionally includes a —C(R 21 )(R 22 )— unit as bridge member;
or R 1 and R 2 together represent group A

G 2 is O(R 13 ), N(R 14 )(R 15 ) or S(R 16 );
G 3 is N(R 17 )(R 18 ) or S(R 19 ));
X 4 is C 1 -C 8 haloalkyl;
R 4 is aryl or aryl substituted by one to five R 9 , or heteroaryl or heteroaryl substituted by one to five R 9 ;
each R 5 is independently hydrogen, halogen, cyano, nitro, NH 2 , C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -C 10 cycloalkyl, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, C 1 -C 8 alkylthio-, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl-, or C 1 -C 8 haloalkylsulfonyl-; or two R 5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge;
each R 6 is independently halogen, cyano, nitro, hydroxy, amino, C 1 -C 8 alkylamino, (C 1 -C 8 alkyl) 2 amino, C 1 -C 8 alkylcarbonylamino, C 1 -C 8 haloalkylcarbonylamino, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, aryloxy or aryloxy substituted by one to five R 10 , aryloxy-C1-C 4 alkanediyl or aryloxy-C1-C 4 alkanediyl in which the aryl moiety is substituted by one to five R 10 , C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxycarbonyl-, mercapto, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl-, C 1 -C 8 haloalkylsulfonyl-, aryl-C 1 -C 4 alkanediylthio or aryl-C 1 -C 4 alkanediylthio in which the aryl moiety is substituted by one to five R 10 ;
each R 7 is independently halogen, cyano, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 alkyl-O—N═, C 1 -C 8 haloalkyl-O—N═, C 1 -C 8 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, or C 1 -C 8 alkoxycarbonyl;
each R 8 is independently halogen, cyano, nitro, oxo, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 cyanoalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkyl-C 1 -C 4 alkanediyl, hydroxy, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, mercapto, C 1 -C 8 alkylthio-, C 1 -C 8 haloalkylthio-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl-, C 1 -C 8 haloalkylsulfonyl-, C 1 -C 8 alkylaminosulfonyl, (C 1 -C 8 alkyl) 2 aminosulfonyl-, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxycarbonyl-, aryl or aryl substituted by one to five R 10 , heterocyclyl or heterocyclyl substituted by one to five R 10 , aryl-C 1 -C 4 alkanediyl- or aryl-C 1 -C 4 alkanediyl- in which the aryl moiety is substituted by one to five R 10 , heterocyclyl-C 1 -C 4 alkanediyl or heterocyclyl-C 1 -C 4 alkanediyl in which the heterocyclyl moiety is substituted by one to five R 10 , aryloxy or aryloxy substituted by one to five R 10 , aryloxy-C 1 -C 4 alkanediyl or aryloxy-C 1 -C 4 alkanediyl in which the aryl moiety is substituted by one to five R 10 ;
each R 9 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, hydroxy, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, mercapto, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsufonyl-, C 1 -C 8 haloalkylsulfonyl-, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxycarbonyl-, aryl or aryl substituted by one to five R 10 , or heterocyclyl or heterocyclyl substituted by one to five R 10 ;
each R 10 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy-, or C 1 -C 4 haloalkoxy-;
each Z is independently halogen, C 1 -C 12 alkyl or C 1 -C 12 alkyl substituted by one to five R 6 , nitro, C 1 -C 12 alkoxy or C 1 -C 12 alkoxy substituted by one to five R 6 , cyano, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfinyl, C 1 -C 12 haloalkylsulfonyl, hydroxyl or thiol;
R 13 , R 16 and R 19 are independently C 1 -C 4 alkyl;
R 14 , R 15 , R 17 , and R 18 are independently hydrogen or C 1 -C 4 alkyl;
R 20 is hydrogen or C 1 -C 4 alkyl;
each R 21 and R 22 is independently halogen or C 1 -C 4 alkyl, or optionally together form a C 3 -C 4 alkanediyl bridge;
n is 0, 1 or 2;

or a salt or N-oxide thereof.

2. The compound according to claim 1 , wherein Q is Q1.

3. The compound according to claim 1 , wherein Y 1 is C—R 5 , C—H or nitrogen, Y 2 and Y 3 are independently C—H or nitrogen and Y 4 is C—R 5 ; in which no more than two of Y 1 , Y 2 and Y 3 are nitrogen and in which Y 2 and Y 3 are not both nitrogen, and wherein two R 5 when present on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge.

4. The compound according to claim 1 , wherein G 1 is oxygen.

5. The compound according to claim 1 , wherein P is P0 or a heterocycle selected from H1 to H9

k is 0, 1 or 2.

6. The compound according to claim 1 , wherein R 1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-.

7. The compound according to claim 1 , wherein R 2 is C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 6 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 7 , aryl-C 1 -C 4 alkanediyl or aryl-C 1 -C 4 alkanediyl in which the aryl moiety is substituted by one to five R 8 , heterocyclyl-C 1 -C 4 alkanediyl or hete

Assignees

• Syngenta Participations Ag

Inventors

• El Qacemi Myriem
• Cassayre Jerome Yves
• Berthon Guillaume
• Rawal Girish
• Patre Rupesh

Classifications

• C07D333/38

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D333/40

  Thiophene-2-carboxylic acid · CPC title

• C07D333/24

  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 · CPC title

• C07D333/32

  Oxygen atoms · CPC title

• A01N37/10

  Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof · CPC title