FIELD OF THE INVENTION:
The present invention relates to compounds of formula (I). More particularly, the present invention relates
5 to an isoxazoline compound of formula (I) and a process for the preparation thereof. The present
invention further relates to the use of isoxazoline compounds of formula (I) as pest control agents.
BACKGROUND OF THE INVENTION:
Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and
insects can further attack wooden dwellings and commercial structures, thereby causing large economic
10 loss to the food supply and to property. Therefore, there is an ongoing need for new compounds for
combating invertebrate pests such as insects, arachnids and nematodes. The currently available modern
insecticides and acaricides have to satisfy many requirements, for example regarding level of efficacy,
spectrum of activity and long lasting effects, and possible use thereof. Efforts have been made during the
past decades to develop selective insecticides that are acting specifically on biochemical modes of action
15 being present only in insects or mites, but additionally showing properties that differ from known
insecticides in an advantageous way.
Isoxazoline compounds with pesticidal activity are known and described, for example, in
WO2008154528, WO2009022746, WO2009112275, WO2010020522, WO2012060317 and WO
2020018610. These documents disclose a substituted isoxazolin ring and a substituted aryl or heteroaryl
20 ring which is attached through a carbon-carbon bond, whereas the present invention discloses the
substituted isoxazolin ring and a substituted heterocyclyl ring which is attached through a carbon-nitrogen
bond.
WO2010020522 discloses the following class of comounds:
however, according to the invention, this patent does not disclose an
25 isoxazolin group attached to a substituted isoindoline group.
Further, by applying such pesticides in a conventional way over several years, many pests develop a
resistance and are no longer sufficiently controlled, and this difficult situation has been even increasing
during recent years. Furthermore, some of those existing pesticides are highly toxic, or remain for a long
3
PI External
time in the environment because of their residual properties, which may become a growing problem due
to the disruption of ecosystems.
Therefore, there is a continuous need for new compounds which are more effective in combating
invertebrate pests, less toxic, and environmentally safer and/or have different modes of action.
5 In view of the above, the present invention envisages such compounds that satisfy or overcome
drawbacks associated with the prior art. It has now surprisingly been found that certain novel, pesticidally
active isoxazoline rings, attached to isoindiline ring compounds being subject of this invention, have
favorable properties as pesticides, as desired

WE CLAIM:
1. A compound of formula (I),
Formula (I)
5 wherein,
R
1
is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl and C3-C6-
halocycloalkyl;
Cy is selected from the group consisting of phenyl and C5-C6-heterocyclyl group, which may optionally
be substituted with one or more groups of R2
;
wherein R2 10 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C2-
C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl and C3-C8-cycloalkyl;
R
3
is selected from the group consisting of hydrogen, halogen, cyano, nitro, C1-C4-alkyl, C2-C4-alkenyl,
C2-C6-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C5-
heterocyclyl, -OC3-C4-heterocyclyl, SCN, SF5, NR′R′′, OR′, S(O)nR′, and CR′=NR″;
A represents a radical selected from the group consisting of direct bond, -CRaR
b 15 -, -C(=W)- or -
CR4aR
4bC(=W)-;
W represents O or S;
R
a and Rb
is independently selected from the group consisting of hydrogen, halogen, cyano, C1-
C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- haloalkyl, C3-C8-cycloalkyl;
D is selected from the group consisting of NR5R
6
, N=S(O)0-1R
8aR
8b
, OR4
, S(O)nR
5 20 , C6-C10-aryl, and C3-
C10-heterocyclyl; wherein cyclic group aryl and heterocyclyl may optionally be substituted with one or
more groups RD
;
R
D
is selected from the group consisting of halogen, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-
alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, OR4
, C1-C6-alkyl-OR4
, C(=O)-
25 R″, C1-C6-alkyl-C(=O)-R″, NR′R″, C1-C6-alkyl-NR′R″, C(=O)-NR′R″, C1-C6-alkyl-C(=O)-
NR′R″, S(O)nR″, C1-C6-alkyl-S(O)nR″, CR′=NR″, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C8-
alkyl, , and Si(R′)3 ;
113
PI External
R
5a is selected from the group consisting of halogen, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-
C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, OR4
, C1-C6-alkylOR4
, C(=O)-R″, C1-C6-alkyl-C(=O)-R″, NR′R″, C1-C6-alkyl-NR′R″, C(=O)-NR′R″, C1-
C6-alkyl-C(=O)-NR′R″, S(O)nR″, C1-C6-alkyl-S(O)nR″, CR′=NR″, C3-C8-cycloalkyl, C3-
5 C8-cycloalkyl-C1-C6-alkyl, and Si(R′)3;
R
4
is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-
alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, C(=O)-R″, C1-C6-alkylC(=O)-R″, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl and C3-C8-heterocyclyl; wherein each
group of R
4 is optionally substituted with one or more groups consisting of halogen, CN,
10 R″, OR″, SR″, N(R′R″) and Si(R′)3;
R
5
is selected from the group consisting of C1-C8-alkyl, C1-C8-cyanoalkyl, C2-C8-alkenyl, C2-C8-
alkynyl, C1-C8-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, OR4
, C1-C8-alkyl-OR4
, C(=O)-
R″, C1-C8-alkyl-C(=O)-R″, NR′R″, C1-C6-alkyl-NR′R″, C(=O)-NR′R″, C1-C8-alkyl-C(=O)-
NR′R″, C2-C6-alkenyl-C(=O)-N(R′R″), C1-C8-alkyl-S(O)nR
4
, S(O)nR
4
, CR′=NR″, C3-C8-
15 cycloalkyl, C3-C8-cyanocycloalkyl, C3-C8-cycloalkyl-C1-C8-alkyl, C3-C8-cyanocycloalkyl-C1-C8-
alkyl, C4-C8-cycloalkenyl, C4-C8-cycloalkynyl, bicyclic C5-C12-alkyl, bicyclic C7-C12-alkenyl, C6-
C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl;
wherein cyclic group may optionally be substituted with one or more groups R5a;
R
5a is selected from the group consisting of halogen, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-
C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, OR4 20 , C1-C6-alkylOR4
, C(=O)-R″, C1-C6-alkyl-C(=O)-R″, NR′R″, C1-C6-alkyl-NR′R″, C(=O)-NR′R″, C1-
C6-alkyl-C(=O)-NR′R″, S(O)nR″, C1-C6-alkyl-S(O)nR″, CR′=NR″, C3-C8-cycloalkyl, C3-
C8-cycloalkyl-C1-C6-alkyl, and Si(R′)3;
R
6
is selected from the group consisting of hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl,
C1-C8-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, OR4
, C1-C6-alkyl-OR4 25 , C3-C8-cycloalkyl,
C3-C8-cycloalkyl-C1-C8-alkyl, Si(R′)3 and (C=O)-R″; or
R
5 and R6 substituents together with the atom to which they are attached may form N=S(O)0-
1R
8aR
8b group; or
R
5 and R6 substituents together with the atom to which they are attached or together with
30 further atoms selected from the group consisting of C, N, O, S and optionally including 1 to
3 ring members selected from the group consisting of C(=O), C(=S), S(O) 0-2 and Si(R′)2,
114
PI External
may form a 3- to 7-membered ring, which for its part is optionally substituted by one or
more groups of R
7
;
R
7 is selected from the group consisting of halogen, cyano, SCN, nitro, C1-C6-alkyl, C2-
C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, SF5,
OR4
, C1-C8-alkyl-OR4 5 , NR′R′′, C1-C8-alkyl-NR′R′′, Si(R′)3, (C=O)-R″, C1-C8-alkyl-
(C=O)-R″, S(O)nR″, C1-C8-alkyl-S(O)nR″, CR′=NR″, C3-C8-cycloalkyl and C3-C8-
cycloalkyl C1-C4-alkyl; or
two R7 substituents together with the atom to which they are attached or together
with further atoms selected from the group consisting of C, N, O, S and optionally
10 including 1 to 3 ring members selected from the group consisting of C(=O), C(=S),
S(O)0-2 and Si(R′)2, may form a 3- to 6-membered ring, which for its part may
optionally be substituted by one or more groups consisting of halogen, CN, R″, OR″,
SR″, NR′R″, Si(R′)3, COOR′ and CONR′R″;
R
8a is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-
15 haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, C1-C6-alkyl-C(=O)-R″, C6-C10-aryl, C6-C10-arylC1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; wherein each group of R
8a
is optionally substituted with one or more groups consisting of halogen, CN, R″, OR″, SR″,
NR′R″, Si(R′)3, COOR′ and CON(R′)2;
R
8b is selected from the group consisting of C1-C6-alkyl or C3-C6-cycloalkyl; or
R
8a and R
8b 20 substituents together with the atom to which they are attached or together
with further atoms selected from the group consisting of C, N, O, S and optionally
including 1 to 3 ring members selected from the group consisting of C(=O), C(=S),
S(O)0-2 and Si(R′)2, may form a 3- to 6-membered ring, which for its part may
optionally be substituted by one or more groups consisting of halogen, CN, R″, OR″,
25 SR″, NR′R″, Si(R′)3, COOR′ and CONR′R″;