US 6,645,984 B2Granted

Arylisoxazoline derivatives, processes for their preparation and their use as pesticides

AssigneeAventis CropScience GmbH

InventorsRalf Braun, Oswald Ort, Karl-Josef Haack, Matthias Eckhardt, Waltraud Hempel, Maria-Theresia Thönessen

Life of this patent

Estimating the term…

Loading patent…

Abstract

Compounds of the formula (I), are described in which X is halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio or (C1-C4)-alkylsulfinyl; R1 is halogen, (C1-C4)-haloalkyl, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy or cyano; m is 0 to 3; n is 1 to 5; Z is oxygen, sulfur, CH2 or NR2; R2 is CN, (C1-C4)-alkoxy-(C1-C4)-alkyl, CHO, (C1-C6)-alkylcarbonyl, (C1-C6)-alkoxycarbonyl or (CW)NR3R4; R3, R4 are H or (C1-C6)-alkyl; W is O or S; G is mono- to tetrasubstituted isoxazoline which is attached in the 3-, 4- or 5-position to the adjacent phenyl ring. The compounds are suitable for use as pesticides.

Claims20

Dependent claims

An arylisoxazoline of the formula (I):

in which:
X is identical or different and is:
a) halogen, cyano, nitro;
b) (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, or (C1-C4)-alkylsulfinyl, where the substituents of group b are unsubstituted or substituted by one or more halogen atoms;
R1 is identical or different and is halogen, (C1-C4)-haloalkyl, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy or cyano;
m is 0 to 4;
n is 1 to 5;
Z is oxygen, sulfur, CH2 or NR2;
R2 is CN, C1-C4-alkoxy-(C1-C4)-alkyl, CHO, (C1-C6)-alkylcarbonyl, (C1-C6)-alkoxycarbonyl or (CW)NR3R4;
R3, R4 are identical or different and are H or (C1-C6)-alkyl;
W is O or S;
G is mono- to tetrasubstituted isoxazoline
which is attached in the 3-, 4- or 5-position to the adjacent phenyl ring;
t is 0, 1, 2 or 3;
R5 is identical or different and is:
a) halogen, CN, NO2;
b) a straight or branched alkyl group having 1 to 12 carbon atoms, where one or more (CH2) groups are optionally replaced by —O—, —S(O)—0,1,2, —NH—, —NR—, —CO—, —CS—, —CH═CH—, —C═C—, unsubstituted or substituted aryldiyl, unsubstituted or substituted heterocyclyldiyl, unsubstituted or substituted (C3-C8)-cycoalkanediyl or unsubstituted or substituted (C3-C8)-cycoalkenediyl, with the proviso that chalcogens when present are not adjacent to one another, where individual hydrogen atoms are optionally replaced by halogen;
c) in the case of two radicals R5 located in the a-position, the radicals are also (═Y), where Y is (═O), (═S), (═NOR6) or (═CR26);
with the proviso that the radical(s) R5 together do not comprise more than one ring system having five or more members;
and
R6 is (C1-C4)-alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted benzyl;
or a pure optical or geometrical isomer, isomer mixture, N-oxide or salt thereof.

19 more elements

The compound having the formula:

wherein:
(a) X1 is F, X2 is F, R′ is H and R″ is methyl;
(b) X1 is F, X2 is F, R′ is H and R″ is isopropyl;
(c) X1 is F, X2 is F, R′ is H and R″ is tert-butyl;
(d) X1 is F, X2 is F, R′ is H and R″ is n-hexyl;
(e) X1 is F, X2 is F, R′ is H and R″ is chloromethyl;
(f) X1 is F, X2 is F, R′ is H and R″ is bromomethyl;
(g) X1 is F, X2 is F, R′ is methyl and R″ is tert-butyl;
(h) X1 is F, X2 is F, R′ is methyl and R″ is CH2-(tert-butyl);
(i) X1 is F, X2 is F, R′ is methyl and R″ is chloromebthyl;
(j) X1 is F, X2 is F, R′ is H and R″ is isobutoxy;
(k) X1 is F, X2 is F, R′ is H and R″ is cyano;
(l) X1 is F, X2 is F, R′ is H and R″ is ethoxymethyl;
(m) X1 is F, X2 is F, R′ is H and R″ is n-propoxymethyl;
(n) X1 is F, X2 is F, R′ is H and R″ is n-butoxymethyl;
(o) X1 is F, X2 is F, R′ is H and R″ is CH2OCF2CF2H;
(p) X1 is F, X2 is F, R′ is H and R″ is CH2OCH2CF3;
(q) X1 is F, X2 is F, R′ is H and R″ is phenoxymethyl;
(r) X1 is F, X2 is F, R′ is H and R″ is 2-pyridyloxymethyl;
(s) X1 is F, X2 is F, R′ is H and R″ is trifluoromethyl;
(t) X1 is F, X2 is F, R′ is H and R″ is n-C3F7;
(u) X1 is F, X2 is F, R′ is H and R″ is n-C4F9;
(v) X1 is F, X2 is F, R′ is H and R″ is n-C6F13;
(w) X1 is F, X2 is F, R′ is H and R″ is phenyl;
(x) X1 is F, X2 is F, R′ if H and R″ is 4-fluorophenyl;
(y) X1 is F, X2 is F, R′ is H and R″ is 4-trifluoromethylphenyl;
(z′) X1 is F, X2 is F, R′ is H and R″ is benzyl;
(a′) X1 is F, X2 is F, R′ is H and R″ is C2H4Br;
(b′) X1 is F, X2 is F, R′ is H and R″ is methylthiomethyl;
(c′) X1 is F, X2 is F, R′ is H and R″ is COOC2H4CF3;
(d′) X1 is F, X2 is F, R′ is H and R″ is CONHC2H5;
(e′) X1 is F, X2 is F, R′ is H and R″ is CON(CH3)2;
(f′) X1 is F, X2 is F, R′ is H and R″ is CON(C2H5)2;
(g′) X1 is F, X2 is F, R′ is H and R″ is CONH(n-C3H7);
(h′) X1 is F, X2 is F, R′ is H and R″ is CONHCH2C2F5;
(i′) X1 is F, X2 is F, R′ is H and R″ is CONHCH2C2H3;
(j′) X1 is F, X2 is F, R′ is H and R″ is CONH(tert-butyl);
(k′) X1 is F, X2 is F, R′ is H and R″ is CONH-(n-pentyl);
(l′) X1 is F, X2 is F, R′ is H and R″ is CONHC3H6OCH3;
(m′) X1 is F, X2 is F, R′ is H and R″ is CONHCH2C3F7;
(n′) X1 is F, X2 is F, R′ is H and R″ is CONHCH2-(2-tetrahydrofuranyl);
(o′) X1 is F, X2 is F, R′ is H and R″ is CONH(4-trifluoromethylphenyl);
(p′) X1 is F, X2 is F, R′ is H and R″ is CONHC2H4(1-piperidinyl);
(q′) X1 is F, X2 is F, R′ is H and R″ is CONHCH2CF3;
(r′) X1 is F, X2 is F, R′ is H and R″ is CONHCH2-(2,6-difluorophenyl);
(s′) X1 is F, X2 is F, R′ is H and R″ is CONHCH2-(3-trifluoromethylphenyl);
(t′) X1 is F, X2 is F, R′ is H and R″ is CH2NHCOCH3;
(u′) X1 is F, X2 is F, R′ is H and R″ is CH2NHCOC2H5;
(v′) X1 is F, X2 is F, R′ is H and R″ is CH2NHCOC2F5;
(w′) X1 is F, X2 is F, R′ is H and R″ is CH2NHCO-n-propyl;
(x′) X1 is F, X2 is F, R′ is H and R″ is CH2NHCOC2H4CF3;
(y′) X1 is F, X2 is F, R′ is H and R″ is CH2NHCO(4-chlorophenyl);
or
(z′) X1 is F, X2 is F, R′ is H and R″ is CH2NHCO(2-chloro-5-pyridyl).

51 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/102,789Filed 22 Mar 2002
Priority: DE 101 14 59723 Mar 2001
Published: US 2003/0114501 A119 Jun 2003
Granted: 11 Nov 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 413/10
Containing two hetero rings: linked by a carbon chain containing aromatic rings
A01N 43/80
Having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms: five-membered rings with one nitrogen atom and either one oxygen…
C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
C07D
Heterocyclic compounds