AU2008202971A1 - Arylisoxazoline derviatives - Google Patents

Description

P001 Section 29 Regulation 3.2(2)

AUSTRALIA

Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT Application Number: Lodged: Invention Title: Arylisoxazoline derviatives The following statement is a full description of this invention, including the best method of performing it known to us: P111AHAU/1107 r 00 5

O

a oo 0 1o Description Arylisoxazoline derivatives, processes for their preparation and their use as pesticides The invention relates to arylisoxazoline derivatives, to processes for their preparation, to compositions comprising them and to their use for controlling animal pests, in particular arthropods, such as insects and Acarina, and helminths.

Owing to their biological activity, certain 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines are suitable for controlling animal pests (see, for example, WO-A- 93/24470, WO-A-95/04726 and WO-A-96/22283).

However, owing to the multifarious requirements that modem pesticides have to meet, for example with respect to efficacy, persistency, activity spectrum, use spectrum, toxicity, combination with other active compounds, combination with formulating agents or synthesis, and owing to the possible occurrence of resistance, the development of such substances can never be considered to be concluded, and there is a constant great need for novel compounds which, at least in some aspects, offer advantages compared to the known compounds.

It was an object of the present invention to provide compounds which, under various aspects, widen the spectrum of pesticides.

This object and other objects which have not been explicitly mentioned, which can be derived or deduced from the contexts discussed here, are achieved by arylisoxazoline derivatives of the formula J^ 00

O

0

O

0 t'-

O

01 0

(N

00 in which the symbols and indices are as defined below: X is identical or different a) halogen, cyano, nitro; b) (C 1

-C

4 )-alkyl, (C 1

-C

4 )-alkoxy, (C 1 -C4)-alkylthio, (Ci-C4)-alkylsulfinyl, where the radicals of group b are unsubstituted or substituted by one or more, preferably one, two or three, radicals selected from the group consisting of halogen; 0 R' is identical or different halogen, (C 1

-C

4 )-haloalkyl,

(C

1

-C

4 )-alkyl, (Ci-C4)-alkoxy, (C-C4)-haloalkoxy or cyano; m is 0, 1, 2, 3 or 4; n is 1,2, 3, 4 or Z is oxygen, sulfur, CH2 or NR 2

R

2 is CN, (C 1 -C4)-alkoxy-(C1-C4)-alkyl, CHO, (C 1

-C

6 )-alkylcarbonyl, (CI-C 6 alkoxycarbonyl or (CW)NR3R4;

R

3

R

4 are identical or different H, (Ci-C 6 )-alkyl; W is O or S; G is mono- to tetrasubstituted, preferably mono- or disubstituted, isoxazoline !0 which is attached in the 4- or 5-position to the adjacent phenyl ring; their pure isomers (optical and geometrical isomers), isomer mixtures, N-oxides and salts suitable for use as pesticides.

Surprisingly, compounds of the formula have, with respect to the activity spectrum and the potency, better acaricidal and insecticidal action than known 1,3-oxazoline, 1,3-thiazoline, pyrroline or imidazoline derivatives.

The symbols and indices in formula preferably have the following meanings: X is preferably halogen, in particular CI, Br or F, cyano, nitro, (Ci-C4)-alkyl,

(C

1

-C

3 )-haloalkyl, (C 1 C4)-alkoxy or (C 1

-C

3 )-haloalkoxy.

00 X is particularly preferably halogen, in particular Cl, Br or F, (Cl-C4)-alkyl, 0 (C 3 )haloalkyl, (Cl-04)-alkoxy or (Cl-0 3 )-haloalkoxy.

NI m is preferably 0 or 1.

n is preferably1, 2 or3.

5 Z is preferably oxygen or OH 2 R1 is preferably H, halogen, (0 1

-C

4 )-haloalkyl, (0-0 4 )alkyl, (0 1

-C

4 )-alkoxy, (0 1

-C

4 )-haloalkoxy.

C\ G is preferably

(N

00

R

5 ,particularly preferably

(R

5 5 t R I or very particularlyrpreferabl

R

5 is ideticlircdffeen substitutor3, reeayldy unusiu0 or susiuedhtrcy.li usubstituted-, NR6_ orO_ subtitte (0 -C-cycoakaed or= unsubstituted or substituted (0 3

-C

8 )-cycloalkenediyl, with the proviso that chalcogens may not be adjacent to one another, where two radicals R 5 together with the atoms of the isoxazoline ring optionally form a 3- to 8- 00 0 membered ring system and where individual hydrogen atoms are 0 CN optionally replaced by halogen; Z c) in the case of two radicals R 5 located in the a-position, the radicals are 5 also where Y is (=NOR 6 or (=CR 2 6 Swith the proviso that the radical(s) R 5 together do not comprise more than one ring system having five or more members.

(N 6 oo 0 R 6 is (C 1

-C

4 )-alkyl, unsubstituted or substituted phenyl or unsubstituted or Ssubstituted benzyl.

As substituents on the isoxazoline radical, the radicals R 5 preferably have the following meanings:

R

5 is identical or different D-R 7 or two radicals R 5 together with the atoms to which they are attached form a three to eight-membered saturated or unsaturated ring system which is unsubstituted or substituted by one or more radicals R 7 and which optionally also contains further heteroatoms, preferably ;0 O, N, S, SO and/or SO 2 D is a direct bond or (C1-C 6 )-alkanediyl, unsubstituted or substituted by one or more halogen atoms;

R

7 is identical or different R 8

R

9

-C(W)R

8

-C(=NOR

8

)R

8 -C(=NNR82)R 8

-C(=W)NR

8 2

-OC(=W)R

8

-OC(=W)OR

8

-NR

8

C(=W)R

8

-N[C(=W)R

8 2

-NR

8

C(=W)OR

8

-C(=W)NR

8 -NR 2, -C(=W)NR 8

-NR

8

[C(=W)R

8 -NR -C(=W)NR82,

-NR

8

-NR

8

C(=W)R

8 -NR -N[C(=W)R 8 2 -N[(C=W)R"]-NR82,

-NR

8

-NR

8

[(C=W)NR

8 2 -N R(C=NR 8

)R

8

-NR"(C=NR

8

)NR

8 2

-O-NR

8 2

-O-NR

8

(C=W)R

8 -S0 2 NR 2

-NR"SO

2

R

8 -S0 2 0R 8 -OS0 2

R

8

-OR

8

-NR

8 2

-SR

8 -SiR 8 3

-PR

2

-P(=W)R

8 2, -SOR', -SO2R 8 -PW2R82, -PW 3

R

8 2 or two radicals R 7 together are (=N-R 8

CR

2 8 or CHR 8 W is O or S;

R

8 is identical or different H, (C-C 6 )-alkyl, (C 2

-C

6 )-alkenyl, (C 2

-C

6 )-alkynyl, (03- 00 0 C 8 )-cycloalkyl, (C 4 -CB)-cycloalkenyl, (C 3

-C

8 )-CYCloalkyl-(0 1

-C

4 )-alkyl, (0 4 -0 8 cycloalkenyl-(C 1

-C

4 )-alkyl, (C3-CB)-cycloalkyl-(C 2

-C

4 )-alkenyl, (C4-C8)cycloalkenyl-(C 2 -C4)-alkenyl, (C 1

-C

6 )-alkyl-(C 3 -C8)-cycloalkyl, (C 2

-C

6 )-alkenyl- 5 (C 3 -C8)-cycloalkyl, (C 2

-C

6 )-alkynyl-(C 3 -C8)-cycloalkyl, -0 6 )-alkyl-(C 4 -C8)cycloalkenyl, (C 2 -Cr 6 )-alkenyl-(C 4 -CB)-cycloalkenyl, aryl, heterocyclyl; where the radicals mentioned are unsubstituted or substituted by one or more radicals R 9 and optionally two radicals R3 together form a ring system; R 9 is identical or different halogen, cyano, nitro, hydroxyl, thio, amino, (01-06)- 00 0 alkanoyl, (C 2

-C

6 )-haloalkanoyl, (C 1

-C

6 )-alkoxy, (C 3

-C

6 )-alkenyloxy, (03-06)alkynyloxy, (Ci -C 6 )-haloalkyloxy, (C 3

-C

6 )-haloalkenyloxy, (03-06)haloalkynyloxy, (C 3

-C

8 )-cycloalkoxy, (0 4 -0 8 )-cycloalkenyloxy, (0 3

-C

8 halocycloalkoxy, (C 4 -0 8 )-halocycloalkenyloxy, (C 3 -C8)-cycloalkyl-(C9 -04)alkoxy, (C 4 -C8)-cycloalkenyl-(C, -0 4 )-alkoxy, (0 3 -C8)-cycloalkyl-(02-04)alkenyloxy, (C 4

-C

8 )-cycloalkenyl-(Cl -C 4 )-alkenyloxy, -C 6 )-alkyl-(C 3

-C

8 cycloalkoxy, (0 2

-C

6 )-alkenyl-(C 3 -C8)-cycloalkoxy, (C 2

-C

6 )-alkynyl-(C 3 -0 8 cycloalkoxy, (C 1

-C

6 )-alkyl-(C 4 -C8)-cycloalkenyloxy, (C 2

-C

6 )-alkenyl-(C 4 -C8)cycloalkenyloxy, -C 4 )-alkoxy-(C, -C 6 )-alkoxy, (C 1 -C4)-alkoxy-(C3-C 6 alkenyloxy, carbamoyl, (0,-C 6 )-mono- or dialkylcarbamoyl, (C,-C 6 )-mono- or ?0dihaloalkylcarbamoyl, (C 3

-C

8 )-mono- or dicycloalkylcarbamoyl, (0-06) alkoxycarbonyl, (C 3 -C8)-cycloalkoxycarbonyl, (C 1

-C

6 )-alkanoyloxy, (C3-CB)cycloalkanoyloxy, (Ci -C 6 )-haloalkoxycarbonyl, (Cl-C 6 )-haloalkanoyloxy,

(C

1

-C

6 )-alkaneamido, (C 1

-C

6 )-haloalkaneamido, C(O)N H(C, -C 6 )-alkyl, 0(0) NH(0 1

-C

6 )-haloalkyl, C(0)NII(C, -C 6 )-alkyl] 2

-C

6 )-haloalkyl] 2 (0 2 -0 6 )-alkeneamido, (C 3

-C

8 )-cycloalkaneamido, (C 3 -C8)-CYCloalkyl-(C,-C 4 alkaneamido, (C 1

-C

6 )-alkylthio, (C 3

-C

6 )-alkenylthio, (C 3

-C

6 )-alkynylthio,

C

6 )-haloalkylthio, (C 3

-C

6 )-haloalkenylthio, (C 3

-C

6 )-haloalkynylthio, (03-08)cycloalkylthio, (C 4 -CB)-cycloalkenylthio, (C 3 -CB)-halocycloalkylthio, (C 4

-C

8 halocycloalkenylthio, (C 3

-C

8 )-cycloalkyl-(C, -C 4 )-alkylthio, (C 4

-C

8 )-cycloalkenyl- (Cl-C4)-alkylthio, (0 3

-C

8 )-CYCloalkyl-(C 3

-C

4 )-alkenylth io, (C 4 -C8)-cycloalkenyl-

(C

3

-C

4 )-alkenylthio, (Ci -C 6 )-alkyl-(C 3

-C

8 )-cycloalkylthio, (C 2

-C

6 )-alkenyl-(0 3

C

8 )-CYCloalkylth io, (C 2

-C

6 )-alkynyl-(C 3 -C8)-cycloalkylthio, (Ci -C 6 )-alkyl-(C 4

-CB)-

cycloalkenylthio, (C 2

-C

6 )-alkenyl-(C 4 -C8)-cycloalkenylthio, -C6)-alkylsu Ifinyl,

(C

3

-C

6 )-alkenylsulfinyl, (C 3

-C

6 )-alkynylsulfinyl, (C 1

-C

6 )-haloalkylsulfinyl, (C3- 00 0 6 )-haloalkenylsulfinyl,

(C

3

-C

6 )-haloalkynylsulfinyl,

(C

3

-C

8 )-cycloalkylsulfinyl,

(C

4

-C

8 )-cycloalkenylsulfinyl,

(C

3

-C

8 )-halocycloalkylsulfinyl, (C4-08)halocycloalkenylsulfinyl, (C: 3

-C

8 )-cycloalkyl-(Cl-C 4 )-alkylsulfiflyl, (04-08)- 5 cycloalkenyl-(Cl -C 4 )-alkylsulfinyl, (C 3

-C

8 )-cycloalkyl-(C3-C 4 )-alkenylsulfiflyl, (0 4 -0 8 )-cycloalkenyl-(C 3

-C

4 )-alkenysu Ifinyl, (C 1 -0 6 )-atkyl-(C3-CB)cycloalkylsulfinyl, (C 2

.C

6 )-alkenyl-(C 3 -C)-cycloalkylsulfilyl, (C 2 -0 6 )-alkynyl- (0 3 -0 8 )-cycloalkylsuIf inyl, (CI -C 6 )-alkyl-(C 4 -0 8 )-cycloalkenylsu Ifinyl, (C 2

-C

6 alkenYl-(C 4 -C8)-cycloalkelulfinyl, (CI -0 6 )-alkylsulf onyl, (03-06)- 00 0 alkenylsulfonyl, (C 3 -0 6 )-alkynylsulfoflyl, (0 1

-C

6 )-haloalkylsulfonyl, (C 3

-C

6 C) haloalkenylsulfonyl, (C 3

-C

6 )-haloalkynylsulfonyt, (C 3 -CB)-cycloalkylsulfonyl, N (C 4 -0 8 )-cycloalkenylsulfoflyl, (0 3

-C

8 )-halocycloalkylsulfonyl, (0 4

-C

8 halocycloalkenylsulfonyl, (C 3 -0 8 )-cycloalkyl-(C 1

-C

4 )-alkylsulfonyl, (04-CB)cycloalkenyl-(Ci -C 4 )-alkylsulfonyl, (C 3 -C8)-cycloalkyl-(C 3

-C

4 )-alkenysulfonyl,

(C

4

-C

8 )-cycloalkenyl-(C 3

-C

4 )-alkenylsulfonyl, (C 1

-C

6 )-alkyl-(C 3 -C8)cycloalkylsulfonyl, (C 2

-C

6 )-alkenyl-(C 3

-C

8 )-cycloalkylsu Ifonyl, (C 2

-C

6 )-alkynyl-

(C

3 -CB)-cycloalkylsuIf onyl, (Cl -C 6 )-alkyl-(C 4

-C

8 )-cycloalkenylsulfonyl, (C 2

-C

6 alkenyl-(C 4

-C

8 )-cycloalkenysulfoflyl,

(C

1

-C

6 )-dialkylamino, (C 1

-C

6 )-alkylamino,

(C

3

-C

6 )-alkenylamino, (C 3

-C

6 )-alkynylamino, (C 1 -0 6 )-haloalkylamino, (0 3

-C

6 !0 haloalkenylamino, (C 3

-C

6 )-haloalkynylamino, (C 3

-C

8 )-cycloalkylamino, (C 4

-C

8 cycloalkenylamino, (C: 3

-C

8 )-halocycloalkamino, (C 4

-C

8 halocycloalkenylamino, (C 3 -C8)-cycloalkyl-(Ci -C 4 )-alkylamino, (C 4

-C

8 cycloalkenyl-(Cl-C4)-alkylamiflo,

(C

3

-C

8 )-cycloalkyl-(C 3 -C4)-alkenylamilo, (0 4 -0 8 )-cycloalkenyl-(0 3

-C

4 )-alkenylamilo, (C 1 -0 6 )-alkyl-(C 3 -0 8 cycloalkylamino, (C 2

-C

6 )-alkenyl-(C 3 -C8)-cycloalkylamilo, (C 2

-C

6 )-alkynyl-

(C

3 -0 8 )-cycloalkylamino, (Cl-C 6 )-alkyl-(C 4 -CB)-cycloalkenylamiflo, (C 2

-C

6 alkenyl-(C 4 -C8)-cycloalkenylamilo,

(C

1

-C

6 )-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C 1

-C

4 )-alkoxy, aryl-(C 1

-C

6 )-alkanoyl, aryl-(C 3 -0 4 )-alkenyloxy, aryl-(Ci -C 4 )-alkylthio, aryl-(C 2

-C

4 )-alkenylthio, aryl-(Cl-C 4 )-alkylamino, aryl-

(C

3 -C4-alkenylamino, aryl-(C 1

-C

6 )-dialkylsilyl, diaryl-(C, -C 6 )-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl, where the cyclic radicals are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, thio, (Cl-C4)-alkyl, 00 0010

(C

1 -C4)-haloalkyl, (C 3 -CB)-cycloalk-yl, (Cl-C4)-alkoxy, (Ci -C 4 )-haloalkoxy(,

(C

1 -C4)-alkythio, (Ci -C4)-haloalkylthio, (CI -C 4 )-alkylamino, (Ci -04)haloalkylamino and (Cl-C 4 )-alkanoyl.

Particularly preferably, R 5 is CN, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, (Cl-C 6 )-alkyl, (Cl -C 6 )-alkenyl, (Ci -C 6 )-haloalkyl, (Cl~-C 6 )-haloalkenyl, -(Cl-C 6 )-alkanediyl-aryl, where the aryl group is unsubstituted or substituted and where one -CH 2 unit is optionally replaced by -C(O)-NR 0

,NR'

0

NR

1 0 or 0.

R

1 0 is H, (C-C 6 )-alkyl, (C 1

-C

6 )-haloalkyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl.

Particularly preferred forQ Xn are the groups

F

and

CI

CH

3

F

andy Cl

CH

3 Br

CH

3 Particularly preferred groups of compounds of the formula are those of the formulae (11) to (128): 00

F

c-I 0 R 5 (i F RIm

F

0 R 5 (2 00

NQ

F

0

R

5 (3

CRI

I (14)

RIM

Br 0 R5

RIM

OH

3

\R

5 (16)

RIM

CH

3

RIM

(1)

RIM

RIM

00 00 (110) Rlm (111) Rlm Rlm (113)

CH

3 Rlm (114)

CH

3 .'Rim (115) (116) Rim (117) Rlm Rlm Rim (120) (121) Rlm

OH

3 Rlm 00

R

(122) Rim (123) Rlm 00 (~KI

R

(124) Rlm (125) Rm

R

6 (126) Rm 0 In the above formula, "halogen" is to be understood as meaning a fluorine, chlorine, c bromine or iodine atom; the term "(CI-C4)-alkyl" is to be understood as meaning an unbranched or branched 5 hydrocarbon radical having 1 to 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical; the term "(C 1

-C

6 )-alkyl" is to be understood as meaning the abovementioned alkyl radicals and also, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl or the hexyl radical; 00 3 the term "(Ci-C 6 )-alkanediyl" is to be understood as meaning an unbranched or branched alkanediyl radical having 1 to 6 carbon atoms, such as methylene, ethane- 1,2-diyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, butane-1,3-diyl or 2-methylpropane-1,3-diyl; the term "(C 1

-C

4 )-haloalkyl" is to be understood as meaning an alkyl group mentioned under the term "(Ci-C 4 )-alkyl" in which one or more hydrogen atoms are replaced by the abovementioned halogen atoms, preferably chlorine or fluorine, such as, for example, the trifluoromethyl group, the 1-fluoroethyl group, the 2,2,2-trifluoroethyl group, the chloromethyl or fluoromethyl group, the difluoromethyl group or the 1,1,2,2-tetrafluoroethyl group; 0 the term "(C 3 -C)-cycloalkyl" is to be understood as meaning, for example, the cyclopropyl, cyclobutyl or cyclopentyl group; and also the cyclohexyl, cycloheptyl or cyclooctyl radical; the term "(C 3 -Cs)-halocycloalkyl" is to be understood as meaning one of the (C 3

-C

8 cycloalkyl radicals listed above, in which one or more, in the case of fluorine optionally also all, hydrogen atoms are replaced by halogen, preferably fluorine or chlorine, such as, for example, the 2,2-difluoro- or 2,2-dichlorocyclopropane group or the fluorocyclopentane radical; the term "(C 2

-C

4 )-alkenyl" is to be understood as meaning, for example, the vinyl, allyl, 2-methyl-2-propenyl or 2-butenyl group; the term "(C 2 -C4)-haloalkenyl" is to be understood as meaning a (C 2

-C

4 )-alkenyl group in which some of, or in the case of fluorine also all, the hydrogen atoms are replaced by halogen, preferably fluorine or chlorine; the term "(C 2 -C4)-alkynyl" is to be understood as meaning, for example, the ethynyl, oo 0 propargyl, 2-methyl-2-propynyl or 2-butynyl group; c the term "(C2-C 6 )-alkynyl" is to be understood as meaning, for example, the abovementioned radicals and also, for example, the 1-pentynyl, 2-pentynyl, 3-pentynyl, or the 4-pentynyl group; the term "haloalkynyl" is to be understood as meaning an alkynyl group in which some of, in the case of fluorine also all, the hydrogen atoms are replaced by halogen Satoms, preferably fluorine or chlorine; the term "(C1-C4)-alkanoyl-(C 1 -C4)-alkyl" is to be understood as meaning, for 00 example, an acetylmethyl, propionylmethyl, 2-acetylethyl or a butyrylmethyl group; the term "(C 1 -C4)-alkanoyl" is to be understood as meaning, for example, the formyl, acetyl, propionyl, 2-methylpropionyl or butyryl group; the term "(C1-C 6 )-alkanoyl" is to be understood as meaning the abovementioned radicals and also, for example, the valeroyl, pivaloyl or hexanoyl group; the term "(C 2

-C

6 )-haloalkanoyl" is to be understood as meaning a (C 2

-C

6 )-alkanoyl group in which some of, in the case of fluorine also all, the hydrogen atoms are replaced by halogen atoms, preferably fluorine or chlorine; the term "(C 1

-C

6 )-alkoxycarbonyl" is to be understood as meaning, for example, the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, Stert-butoxycarbonyl, pentyloxycarbonyl or hexyloxycarbonyl group; the term "(Ci-C 6 )-haloalkoxycarbonyl" is to be understood as meaning a (C1-C6)alkoxycarbonyl group in which one or more, in the case of fluorine optionally also all, hydrogen atoms are replaced by halogen, preferably fluorine or chlorine; the term "(C1-C 6 )-alkylthio" is to be understood as meaning an alkylthio group whose hydrocarbon radical has the meaning given under the term 6 )-alkyl"; the term "(C1-C 6 )-haloalkylthio" is to be understood as meaning a (C-C 6 )-alkylthio group in which one or more, in the case of fluorine optionally also all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine; the term "(C1-C 6 )-alkylsulfinyl" is to be understood as meaning, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl-, tert-butyl-, pentyl-, 2-methylbutyl- or hexylsulfinyl group; the term "(C 1

-C

6 )-alkylsulfonyl" is to be understood as meaning, for example, the 00oo S methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl-, tert-butyl-, pentyl-,

O

c- 2-methylbutyl- or hexylsulfonyl group; the terms "(C 1

-C

6 )-haloalkylsulfinyl" and "(C 1

-C

6 )-haloalkylsulfonyl" are to be 5 understood as meaning (C1-C6)-alkylsulfinyl and -sulfonyl radicals having the meanings given above in which one or more, in the case of fluorine optionally also all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine; the term "(C1-C 6 )-alkoxy" is to be understood as meaning an alkoxy group whose 00oo 0 hydrocarbon radical has the meaning given under the term "(Ci-Cs)-alkyl"; the term "(C1-C 6 )-alkylamino" is to be understood as meaning, for example, the methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, tert-butylamino, pentylamino or the hexylamino group; the term "(Ci-C s )-dialkylamino" is to be understood as meaning, for example, the dimethylamino, methylethylamino, diethylamino, dipropylamino, dibutylamino, dipentylamino or the dihexylamino group; but also cyclic systems, such as, for example, the pyrrolidino or piperidino group, the term "(C1-C 6 )-haloalkoxy" is to be understood as meaning a haloalkoxy group whose halohydrocarbon radical has the meaning given under the term "(C1-C6)- ?0 haloalkyl"; the term "aryl" is to be understood as meaning a carbocyclic aromatic radical having preferably 6 to 14, in particular 6 to 12, carbon atoms, such as phenyl or naphthyl, preferably phenyl; the term "heterocyclyl" is to be understood as meaning a heteroaromatic or heteroaliphatic ring system, where "heteroaromatic ring system" is to be understood as meaning an aryl radical in which at least one CH group is replaced by N and/or at least two adjacent CH groups are replaced by S, NH or 0, for example a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene', carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 0 1,2,4,5-triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, c 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine or 4H-quinolizine radical; and the term "heteroaliphatic ring system" is to be understood as meaning a (C3-Ce)cycloalkyl radical in which at least one carbon unit is replaced by O, S or a group

NR

11 and R 11 is hydrogen, (Ci-C4)-alkyl, (C 1 -C4)-alkoxy or aryl; the term "arylthio" is to be understood as meaning, for example, the phenylthio group; 0 0 the term "aryloxy" is to be understood as meaning, for example, the phenoxy group; the term "heterocyclyloxy" or "heterocyclylthio" is to be understood as meaning one of the heterocyclic radicals mentioned above which is attached via an oxygen or sulfur atom; the term "(C 3 -Ce)-cycloalkoxy" or "(C 3 -Cs)-cycloalkylthio" is to be understood as meaning one of the (C 3

-C

8 )-cycloalkyl radicals listed above which is attached via an oxygen or sulfur atom; the term "(C 3 -Ce)-cycloalkoxycarbonyl" is to be understood as meaning, for example, the cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or the cycloheptyloxycarbonyl group; !0 and the,term "unsubstituted or substituted aryl, heterocyclyl, phenyl, etc." is to be understood as meaning, preferably, substitution by one or more, preferably 1 to 3, in the case of halogen also up to the maximum number of, radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, thio, (Ci-C4)-alkyl, (C1-C 4 )-haloalkyl, (Cs-Ce)-cycloalkyl, (C1-C 4 )-haloalkylthio, (C1-C 4 )-alkylamino, (C1-

C

4 )-haloalkylamino, formyl or (Cl-C4)-alkanoyl.

The explanation given above applies correspondingly to homologs and radicals derived therefrom.

The present invention relates to the compounds of the formula in the form of the free base or an acid addition salt. Acids which can be used for salt formation are, for example, inorganic acids, such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, or organic acids, such as formic acid, acetic acid, propionic acid, malonic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic 0 acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid.

In some cases, the compounds of the formula contain one or more chiral carbon 5 atoms or stereoisomers on double bonds. Enantiomers or diastereomers can therefore occur. The invention relates both to the pure isomers and to mixtures thereof. The mixtures of diastereomers can be separated into the components by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by 0 customary methods, thus, for example, by salt formation with a chiral, enantiomerically pure acid, separation of the diastereomeric salts and liberation of the pure enantiomers by means of a base.

The compounds according to the invention are prepared by methods which are known per se from the literature, as described in standard works on organic synthesis, for example Houben-Weyl, Methoden der Organischen Chemie [Methods in Organic Chemistry], Georg-Thieme-Verlag, Stuttgart.

The preparation is carried out under reaction conditions which are known and 0 suitable for the abovementioned reactions. Other variants which are known per se, but not illustrated here in greater detail, may also be used.

If desired, the starting materials may also be formed in situ, in such a way that they are not isolated from the reaction mixture but immediately reacted further to give the compounds of the formula The general chemistry of 1,3-oxazolines is described, for example, in Tetrahedron, 1994, 50, 2297-2360 and in Nachr. Chem. Tech. Lab. 1996, 44, 744-750.

The invention also provides a process for preparing compounds of the formula (I, G 3-isoxazinyl) by reacting 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines of the formula (II) (see, for example, WO-A-96/22283) (suitably substituted by Xn and R m) with a halogenating agent to give compounds of the 00 00 formula (III), and reacting these compounds with an olefin (IV) (suitably substituted by R5t), where initially an oxime of the formula (II), Z (II) in which X and Z have the meanings given in formula (I) is reacted with a halogenating agent, preferably a chlorinating agent, to give a compound of the formula (III) in which Hal is halogen, preferably Cl, and then reacted further with an olefin of the formula (IV), Rst

(IV)

R

5 t in which R 5 and t have the meanings given above.

The invention also provides a process for preparing compounds of the formula (II) by reacting 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines of the formula (suitably substituted by X and with hydroxylamine or its salts, if appropriate in the presence of a base, 00 n in which S Xn and Z have the meanings given in formula The invention also provides a process for preparing compounds of the formula (V) oo from 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines of the formula (VI) (suitably substituted by X and where compounds of the formula (VI) z N (VI) n 1 Y2

H

0 in which Y' and Y2 independently of one another are hydrogen, (C 1

-C

4 )-alkyl, (Ci-C4)alkoxycarbonyl or phenyl and Xn and Z have the meanings given in formula (I) are reacted with an oxidizing agent to give compounds of the formula Methods A to D are illustrated using the synthesis of different subgroups of compounds of the formula (G 3-isoxazinyl) as an example: The isoxazole ring is advantageously generated in the presence of a base, for example selected from the group of the alkali metal hydroxides, alkali metal carbonates, alkoxides and amines.

Method A R5 t 9W Using halogenating agents, oximes of the formula (II) are converted into the halooximes (111). Suitable halogenating agents are, for example, elemental halogen, hypohalites and N-haloimides: Method B halogenating agent

I'-,H

0i Oximes of the formula (II) are prepared by reacting aldehydes of the formula with hydroxylamine or hydroxylamine salts, if appropriate in the presence of a base: Method C z

N

Rlm

H

H

2

NOH

00 00

O

oo a>

(N

Aldehydes of the formula are generated by cleaving the olefins of the formula (VI) using an oxidizing agent. Suitable oxidizing agents are, for example, ruthenium or osmium compounds in combination with a periodate, or ozone: Method D oxidizing agent m

H

(VI)

Some compounds of the formula (VI) have been described (WO-A-95/04726) or 0 they can be prepared in a similar manner.

The invention also provides a process for preparing compounds of the formula (I) (G 5-isoxazinyl) by reacting 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines of the formula (VII) (see, for example, WO-A 95/04726), suitably substituted by Xn and R'm, with a halooxime, where an olefin of the formula (VII) N

(VII)

in which Z and R 5 t have the meanings given above, is reacted with a halooxime of the formula (VIII) Hal R IR

(VIII)

H ON where R 5 has the meanings given above.

oo 0 c Method E is illustrated using the synthesis of compounds of the formula (I) S (G 3-isoxazinyl) as an example: The isoxazole ring is generated in the presence of a base, selected, for example, from the group consisting of alkali metal hydroxides, alkali metal carbonates, alkoxides and amines.

0 00 0 Method E

O

YN

N

IN T H G

R'

1 t R'm (VII) (VIII)

(I)

Various esters and amides as radicals R 5 can be prepared, for example, from acid derivatives. These, for their part, are obtainable, for example, by ester hydrolysis, for example o

NN

O

z RS/NR8 N 0 Xn R'm Suitable for use as hydrolyzing agents are, for example, aqueous alkali metal hydroxide solutions.

During the preparation of the amides or esters, the acid can be activated using, for example, a carbodiimide, carbonyldiimidazole or an inorganic acid chloride, for example thionyl chloride.

Various esters and amides as radical R 5 can also be prepared, for example, from hydroxyl and amine derivatives. These, for their part, are obtainable, for example, by ester or amide hydrolysis, for example: 00 OR 8

/NR

8 Xn n

R

1 m

H/NHR

8 O N 00 Xn 0

N\

Xn m Suitable for use as hydrolyzing agents are, for example, aqueous alkali metal hydroxide solutions.

To prepare the amides or esters, the alcohol or the amine can be reacted, for example, with an activated acid, e.g. an acid chloride.

Collections of compounds of the formula which can be synthesized by the abovementioned scheme may also be prepared in a parallel manner and this may be effected manually or in a semiautomated or fully automated manner. In this case, it is possible, for example, to automate the procedure of the reaction, the work-up or the purification of the products or of the intermediates. In total, this is to be understood as meaning a procedure as is described, for example, by S.H. DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated synthesis", Volume 1, Verlag Escom 1997, pages 69 to 77.

A number of commercially available apparatuses as are offered by, for example, oo 0 Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H+P c Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleifheim, Germany, may be used for the parallel procedure of the reaction and work-up. For the parallel purification of compounds of the formula or of intermediates obtained during the preparation, use may be made, inter alia, of chromatography apparatuses, for example those from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

The apparatuses mentioned lead to a modular procedure in which the individual 00 0 process steps are automated, but manual operations have to be performed between the process steps. This can be avoided by employing semiintegrated or fully integrated automation systems where the automation modules in question are operated by, for example, robots. Such automation systems can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.

In addition to what has been described here, compounds of the formula may be prepared in part or fully by solid-phase-supported methods. For this purpose, individual intermediate steps or all intermediate steps of the synthesis or of a synthesis adapted to suit the procedure in question are bound to a synthetic resin.

!0 Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A. Bunin in "The Combinatorial Index", Verlag Academic Press, 1998.

The use of solid-phase-supported synthesis methods permits a series of protocols which are known from the literature and which, in turn, can be performed manually or in an automated manner. For example, the "tea-bag method" (Houghten, US 4,631,211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), in which products from IRORI, 11149 North Torrey Pines Road, La Jolla, CA 92037, USA, are employed, may be semiautomated. The automation of solid-phase-supported parallel syntheses is performed successfully, for example, by apparatuses from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

The preparation according to the processes described herein yields compounds of Sthe formula in the form of substance collections which are referred to as libraries.

The present invention also relates to libraries which comprise at least two S compounds of the formula The compounds of the formula are suitable for controlling animal pests, in particular insects, arachnids, helminths and molluscs, very especially preferably for controlling insects and arachnids, which are encountered in agriculture, in livestock breeding, in forests, in the protection of stored goods and materials and in the 0 hygiene sector, and have good plant tolerance and favorable toxicity to warmblooded species. They are active against normally sensitive and resistant species and against all or individual development stages. The abovementioned pests include: From the order of the Acarina, for example, Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.

0 From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeira, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., 00 Pediculus humanus corporis, Haemnatopinus spp. and Linognathus spp.

N- From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea sppD.

From the order of the Thysanoptera, for example, Hercinoth rips femoralis and Thrips tabaci.

__From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma 00 D From the order of the Homoptera., for example, Aleurodes brassicae, Bemnisia tabaci, 0 Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ci ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium comi, Saissetia oleae, Laodelphax stniatellus, Nilaparvata lugens, Aonidiella aurantil, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria 0 spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamnestra. brassicae, Panolis flammea, Prodenia litura, Spodloptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumniferana, Clysia ambiguella, Homona magnanima and Tortrix viridlana.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedlon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus su rinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera. postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, 00 Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and c Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., 5 Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio 00 0 hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Qesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola.

.0 From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bu inus spp. and Oncomelania spp.

From the class of Bivalva, for example, Dreissena spp.

The phytoparasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root gall nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cystforming nematodes, such as Globodera rostochiensis, Globodera pallida and Heterodera trifolii) and of the genera Radopholus, such as Radopholus similis, Pratylenchus, such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus, Tylenchulus, such as Tylenchulus semipenetrans, Tylenchorhynchus, such as 00 Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus, such as Rotylencus robustus, Heliocotylenchus, such as Heliocotylenchus multicinctus, S Belonoaimus, such as Belonoaimus longicaudatus, Longidorus, such as Longidorus elongatus, Trichodorus, such as Trichodorus primitivus and Xiphinema, such as Xiphinema index.

The nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides 0) 3 ritzemabosi) and Anguina (blossom nematodes, such as Anguina tritici) can furthermore be controlled with the compounds according to the invention.

The invention also relates to compositions, for example crop protection compositions, preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluscidal or fungicidal, particularly preferably insecticidal and acaricidal compositions, which comprise one or more compounds of the formula in addition to suitable formulation auxiliaries.

In general, the compositions according to the invention comprise from 1 to 95% by D weight of the active compounds of the formula For preparing the compositions according to the invention, the active compound and the other additives are combined and formulated as a suitable use form.

They can be formulated in various ways, depending on how this is predetermined by the biological and/or chemico-physical parameters. Suitable formulation possibilities are therefore: Wettable powders emulsifiable concentrates aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions dusting powders seed dressings, granules in the form of microgranules, sprayed granules, absorption granules and adsorption granules, water-dispersible granules ULV formulations, microcapsules, waxes or baits.

These individual types of formulation are known in principle and are described, for oo 0 example, in: Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], c- Volume 7, C. Hanser Verlag Munich, 4th Edition 1986; van Falkenberg, "Pesticides Z Formulations", Marcel Dekker 2nd Edition 1972-73; K. Martens, "Spray Drying 5 Handbook", 3rd Edition 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Edition, Darland 0 0 Books, Caldwell H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Edition, J. Wiley Sons, Marsden, "Solvents Guide", 2nd Edition, Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood Sisley and Wood, "Encyclopedia of Surface-Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Sch6nfeldt, "Grenzflichenaktive Athylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-KOchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hanser Verlag Munich, 4th Edition 1986.

Combinations with other substances having a pesticidal action, fertilizers and/or 0 growth regulators can be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, alongside the active compound, and in addition to a diluent or inert substance, also comprise wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2'-dinaphthylmethane-6,6'-disulfonate.

Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. Emulsifiers which can be used are, for example: calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,

I

propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan 00 0 fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene c sorbitol esters.

Dusting powders are obtained by grinding the active compound with finely divided solid substances, for example talc, naturally occurring clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, 00 0 such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules if desired as a mixture with fertilizers.

In wettable powders, the active compound concentration is for example about 10 to by weight, the remainder to make up 100% by weight comprising customary formulation constituents. In emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations usually comprise 5 to 20% by weight of active compound, and sprayable solutions about 2 .0 to 20% by weight. In granules, the content of active compound partly depends on whether the active compound is present in liquid or solid form and what granulating auxiliaries, fillers and the like are used.

In addition, the active compound formulations mentioned comprise, if appropriate, the particular customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetration agents, solvents, fillers or carrier substances.

For use, the concentrates in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also microgranules. Dust-like and granular formulations as well as sprayable solutions are usually not diluted further with additional inert substances before use.

The required amount applied varies with the extemrnal conditions, such as 00oo S temperature or humidity. It can vary within wide limits, for example between 0.0005 0 cN and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and kg/ha.

The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations (see the above mentioned compositions) as mixtures with other active compounds, such as insecticides, attractants, sterilizing agents, acaricides, oo 0 nematicides, fungicides, molluscides, growth-regulating substances or herbicides.

The pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds and substances produced by microorganisms.

Preferred partners for the mixtures are: 1. from the group of phosphorus compounds acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos- 0 ethyl, cadusafos (F-67825), chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, fosthiazate (ASC-66824), heptenophos, isazophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosphocarb (BAS-301), phosmet, phosphamidon, phoxim, pirimiphos, primiphosethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion; 2. from the group of carbamates alanycarb (OK-i 35), aldicarb, 2-sec-butyiphenyl methylcarbamate (BPMC), carbaryl, 0 801, isoprocarb, methomyl, 5-methyl-m-cumenyl b utyryl (methyl)carbam ate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1 -m ethylth io (ethyl ideneam ino) N-methyl- N-(morpholinothio)carbamate (UC 51717), triazamate; 3. from the group of carboxylic acid esters acrinathrin, allethrin, aiphametrin, 5-benzyl-3-f urylm ethyl 1 R)-cis-2,2-di-methylcI 3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, beta-cyfluthrin, beta- 00 cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, (RS)-i -cyano-i -(6-phenoxy-2-pyndyl)methyl (1 RS)-trans-3-(4-tertcI butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothnin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin (S-41 31 lambda-cyhalothrin, permethrin, pheothrin isomer), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin (TD-2344), tralometh rin, transfluthrin and zeta-cypermethnin (F-5670 1); 0 4. from the group of amidines amitraz, chiordimeform; from the group of tin compounds cyhexatin, fenbutatin oxide; 6. others abamnectin, ABG-9008, acetamiprid, Anagrapha falcitera, AKD-1 022, AKD-3059, ANS-1 18, Bacillus thuringiensis, Beauvenia bassianea, bensultap, bifenazate (D- 2341), binapacryl, BJL-932, bromopropylate, BTG-504, BTG-505, buprofezin, camphechlor, cartap, ch lo robenzi late, chiorfenapyr, chlorfluazuron, 2-(4- (U BI-T 930), chlorfentezine, chromnafenozide (ANS-1 18), CG-216, CG-217, CG-234, A-i 84699, 2-naphthylmethyl cyclopropanecarboxylate (Rol 2-0470), cyromazin, diacloden (thiamethoxam), diafenthiuron, N-(3,5-dichloro-4-(1 ,1 ,2,3,3,3-hexafluoro-1 00 propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboxamide acid ethyl ester, DDT, dicofol, diflubenzuron, N-(2,3-dihydro-3-methyl-1 ,3-thiazol-2-ylidene)-2,4-xylidine, dinobuton, dinocap, diofenolan, DPX-062, emamectin-benzoate (MK-244), endosulfan, ethiprole (sulfethiprole), ethofenprox, etoxazole (YI-5301), fenazaquin, fenoxycarb, fipronil, fluazuron, flumite (flufenzine, SZI-1 21), 2-f luoro-5-(4-(4ethoxyphenyl)-4-methyl-l1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenpyroximate, fenthiocarb, flubenzimine, flucycloxu ron, flufenoxu ron, flufenprox (ICI-A5683), fluproxyfen, gamma-HCH, halofenozide (RH- 00 0 0345), halofenprox (MTI-732), hexaflumuron hexythiazox, HOI-9004, hydramethylnon (AC 217300), IKI 220, imidacloprid, indoxacarb (DPX-MP062), kanemite (AKD-2023), M-020, MTI-446, ivermectin, lufenuron, M-020, methoxyfenozide (intrepid, RH-2485), milbemnectin, NC- 196, neemgard, nitenpyram (TI-304), 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4dihydrothiazole (SD 35651), 2-nitromethylene-1 ,2-thiazinan-3-ylcarbamaldehyde (WL 108477), pyriproxyfen (S-71639), NC-1 96, N-li111, NNI-9768, novaluron (MCW-275), OK-9701, OK-9601, OK-9602, propargite, pymnethrozine, pyridaben, pyrimidifen (SU-8801), RH-0345, RH-2485, RYI-210, S-i1283, S-1833, SB37242, SI- 8601, silafluofen, silomadine (CG-1 77), spinosad, SU-91 18, tebufenozide, 0 tebufenpyrad (MK-239), teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, TI-435, tolfenpyrad (OMI-88), triazamnate (RH-7988), triflumuron, verbutin, vertalec (Mykotal), YI-5301.

The active compound content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active compound, preferably between 0.0000 1 and 1 by weight. The active compounds are used in a customary manner appropriate for the use forms.

The invention also provides a method for controlling harmful insects, Acarina, molluscs and/or nematodes, in which an effective amount of a compound according to the invention or a composition according to the invention is applied to these organisms or the plants, areas or substrates infested with them.

The invention also provides the use of a compound according to the invention or a 00 S composition according to the invention for controlling harmful insects, Acarina, c- molluscs and/or nematodes.

The active substances according to the invention are also suitable for the field of veterinary medicine, preferably for controlling endo- and ectoparasites, and for the field of animal husbandry.

N' The active substances according to the invention can preferably be applied in a N 0 known manner, such as by oral application in the form of, for example, tablets, 00 capsules, potions or granules, by dermal application in the form of, for example, S dipping, spraying, pouring-on and spotting-on and dusting, and also by parenteral application in the form of, for example, injection.

The compounds of the formula according to the invention can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese etc.). In a preferred embodiment of the invention, the novel compounds, if appropriate in suitable formulations (cf.

above) and if appropriate with the drinking water or feed, are administered orally to '0 the animals. Since excretion in the feces occurs in an effective fashion, the development of insects in the animal feces can be prevented very simply in this fashion. The dosages and formulations suitable in each case, in particular, depend on the type and developmental stage of the productive animals and also on the severity of infestation and can easily be determined and fixed by conventional methods. In the case of cattle, the compounds can be employed, for example, in dosages of 0.01 to 1 mg/kg of body weight.

Accordingly, the invention also provides the use of a compound of the formula or one of the abovementioned compositions for preparing a veterinary medicament.

In addition, the compounds according to the invention are also suitable for use in industrial fields, for example as wood preservative, as preservative in paints, in cooling lubricants for metal working or as preservative in drilling and cutting oils.

00 Compounds of the formula in their commercially available formulations can be used either alone or in combination with other fungicides known from the literature.

Examples of fungicides which are known from the literature and which can be combined in accordance with the invention with the compounds of the formula are the following products: aldimorph, andoprim, anilazine, BAS 480F, BAS 450F, benalaxyl, benodanil, cl benomyl, binapacryl, bitertanol, bromuconazole, buthiobate, captafol, captan, c 0 carbendazim, carboxin, OGA 173506, cyprofuram, dichlofluanid, dichlomezin, 00 diclobutrazol, diethofencarb, difenconazole (CGA 169374), difluconazole, N dimethirimol, dimethomorph, diniconazole, dinocap, dithianon, dodemorph, dodine, edifenfos, ethirimol, etridiazol, fenarimol, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferimzone (TF164), fluazinam, fluobenzimine, fluquinconazole, fluorimide, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, fuberidazole, fulsulfamide (MT-F 651), furalaxyl, furconazole, furmecyclox, guazatine, hexaconazole, ICI A5504, imazalil, imibenconazole, iprobenfos, iprodione, isoprothiolane, KNF 317, copper compounds such as copper oxychloride, oxine-copper, copper oxide, mancozeb, maneb, mepanipyrim (KIF 0 3535), metconazole, mepronil, metalaxyl, methasulfocarb, methfuroxam, MON 24000, myclobutanil, nabam, nitrothalidopropyl, nuarimol, ofurac&, oxadixyl, oxycarboxin, penconazole, pencycuron, PP 969, probenazole, propineb, prochloraz, procymidon, propamocarb, propiconazole, prothiocarb, pyracarbolid, pyrazophos, pyrifenox, pyroquilon, rabenzazole, RH7592, sulfur, tebuconazole, TF 167, thiabendazole, thicyofen, thiofanate-methyl, thiram, toiclofos-methyl, tolyifluanid, triadimefon, triadimenol, tricyclazole, tridemorph, triflumizole, triforine, validamycin, vinchlozolin, XRD 563, zineb, sodium dodecylsulfonate, sodium dodecyl sulfate, sodium C13/Cl 5-alcohol ether sulfonate, sodium cetostearyl phosphate ester, sodium dioctylsulfosuccinate, sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, cetyltrimethylammonium chloride, salts of longchain primary, secondary or tertiary amines, alkylpropyleneamines, laurylpyrimidinium bromide, ethoxylated quatemized fatty amines, alkyldimethylbenzylammonium chloride and 1 -hyd roxylethyl-2-alkylim idazoline.

00 The abovementioned components are known active substances, many of which are described in C.D.S. Tomlin, S.B. Walker, The Pesticide Manual, 12th Edition, British Crop Protection Council, Famham 2000.

The invention also provides seed, comprising or coated with an effective amount of a compound according to the invention or of a composition according to the invention.

0 The compounds of the formula can also be employed for controlling harmful 00 organisms in crops of known or genetically engineered plants yet to be developed.

As a rule, the transgenic plants are distinguished by particular advantageous properties, for example by resistances to certain crop protection agents, resistances to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storage properties, composition and specific constituents. Thus, transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid spectrum of the harvested material, are known.

,0 The use in economically important transgenic crops of useful plants and ornamentals, for example, cereals such as wheat, barley, rye, oats, millet and sorghum, rice, cassava and maize or else crops of sugar beet, cotton, soya, oilseed rape, potatoes, tomatoes, peas and other vegetables is preferred.

When being use in transgenic crops, in particular those in which the plants express an insecticide, effects are frequently found (in addition to the pesticidal effects which can be observed in other crops) which are specific to application in the transgenic crop in question, for example an altered or specifically widened spectrum of pests which can be controlled, or altered application rates which can be used for application.

The invention therefore also provides the use of compounds of the formula for S controlling harmful organisms in transgenic crop plants.

The use according to the invention of compounds of the formula or compositions comprising them, for example an insecticide, acaricide, molluscide or nematicide, includes the case where the compound of the formula or its salt is formed from a precursory substance only after application, for example in the insect, in a plant or in the soil.

0 The contents of German patent application 101 14 597.7, whose priority is claimed 00oo by the present application, and the contents of the appended summary are incorporated herein specifically by way of reference; they are considered to be part of the present description by way of citation.

The examples which follow serve to illustrate the invention without restricting it thereto.

SA. Preparation examples 3-Arylisoxazolines SIntermediate 12: 2-(2,6-difluorophenyl)-4-(4-(2-phenylethenyl)phenyl)oxazoline 2-(2,6-Difluorophenyl)-4-(4-bromophenyl)oxazoline (33.8 g, 0.1 mol) and styrene C (22.9 ml, 0.2 mol) in 300 ml of DMF were heated at reflux with sodium carbonate (11.66 g, 0.11 mol), tris(2,4-di-tert-butylphenyl)phosphite (6.47 g, 10 mmol) and palladium acetate (0.45 g, 2 mmol) for 20 h. Following extractive work-up with ethyl acetate, the residue was triturated with heptane/dichloromethane This gave 27 g of crystals, m.p. 141 C.

Intermediate 12: 2-(2,6-difluorophenyl)-4-(4-formylphenyl)oxazoline At 0°C, 2-(2,6-difluorophenyl)-4-(4-(2-phenylethenyl)phenyl)oxazoline (7.22 g, mmol) and sodium metaperiodate (8.55 g, 20 mmol) were suspended in acetonitrile/acetone/water 180 ml), and a catalytic amount of ruthenium 0 trichloride hydrate was added. Following extractive work-up with ethyl acetate and column chromatography, 5.6 g of the aldehyde were obtained as a viscous oil.

Intermediate 13: 2-(2,6-difluorophenyl)-4-(4-(hydroxyiminomethyl)phenyl)oxazoline At room temperature, 2-(2,6-difluorophenyl)-4-(4-formylphenyl)oxazoline (5.6 g), hydroxylamine hydrochloride (1.53 g, 1.1 equivalents) and sodium acetate (4.9 g, 3 equivalents) were stirred in 50 ml of ethanol for 24 h. Following extractive work-up with ethyl acetate and column chromatography, 4.2 g of crystals were obtained, m.p.

1590C.

2-(2,6-Difluorophenyl)-4-(4-(5-tert-butylisoxazolin-3-yl)phenyl)oxazoline (Ex. No. 9) 00

O

c At 50°C, 2-(2,6-difluorophenyl)-4-(4-(hydroxyiminomethyl)phenyl)oxazoline (40 mg, 0.13 mmol) and N-chlorosuccinimide (19 mg, 1.1 equivalents) in 2 ml of DMF were heated for 4 h. After cooling to room temperature, 3,3-dimethylbutene (33 mg, 0.4 mmol) and triethylamine (41 mg, 0.4 mmol) were added. After 16 h of stirring, the mixture was worked up by extraction with ethyl acetate and the residue was purified by column chromatography. This gave 19 mg of product.

OO 0 2-(2,6-Difluorophenyl)-4-(4-(5-trifluoromethylisoxazolin-3-yl)phenyl)oxazoline (Ex. No. 43) At 50°C, 2-(2,6-difluorophenyl)-4-(4-(hydroxyiminomethyl)phenyl)oxazoline (40 mg, 0.13 mmol) and N-chlorosuccinimide (19 mg, 1.1 equivalents) in 2 ml of DMF were heated for 4 h. After cooling to room temperature, 2 ml of a DMF solution saturated with 3,3,3-trifluoropropene, and triethylamine (41 mg, 0.4 mmol) were added. After 16 h of stirring, the mixture was worked up by extraction with ethyl acetate and the residue was purified by column chromatography. This gave 37 mg of product.

!0 2-(2,6-Difluorophenyl)-4-(4-(5-(trifluoroacetamidomethyl)isoxazolin- 3-yl)phenyl)oxazoline (Ex. No. 115) At 50°C, 2-(2,6-difluorophenyl)-4-(4-(hydroxyiminomethyl)phenyl)oxazoline (1.2 g, 4 mmol) and N-chlorosuccinimide (560 mg, 1.05 equivalents) in 6 ml of DMF were heated for 4 h. After cooling to room temperature, N-allyltrifluoroacetamide (2.75 g, 3 equivalents) and triethylamine (1.66 ml, 3 equivalents) were added. After 16 h of stirring, the mixture was worked up by extraction with ethyl acetate and the residue was purified by column chromatography. This gave 920 mg of product.

2-(2,6-Difluorophenyl)-4-(4-(5-(propionylaminomethyl)isoxazolin-3-yl)phenyl)- 0 oxazoline (Ex. No. 116)

O

2-(2,6-Difluorophenyl)-4-(4-(5-(trifluoroacetamidomethyl)isoxazolin-3-yl)phenyl)oxazoline (43 mg) in 2 ml of methanol was admixed with 0.5 ml of 2N aqueous sodium hydroxide solution, and the mixture was stirred for 16 h. Following extractive work-up with dichloromethane, triethylamine (0.05 ml) and propionyl chloride (50 mg) S were added at 0°C to the crude amine in 2 ml of dichlromethane. After 2 h of stirring, Nc the mixture was worked up by extraction with ethyl acetate and the residue was c 0 purified by column chromatography. This gave 40 mg of product.

0oo S Intermediate 14: 2-(2,6-difluorophenyl)-4-(4-ethenylphenyl)oxazoline In an autoclave, 2-(2,6-difluorophenyl)-4-(4-bromophenyl)oxazoline (6.0 g, 18 mmol), sodium carbonate (2.9 g, 21 mmol), tris(2,4-di-tert-butylphenyl) phosphite (1.2 g, 1.8 mmol) and palladium acetate (64 mg, 2% equivalents) in 100 ml of DMF were heated under 20 bar of ethylene at 150°C for 44 h. Extractive work-up with ethyl ?0 acetate and column chromatography gave 3.75 g of crystals, m.p. 760C.

2-(2,6-Difluorophenyl)-4-(4-(3-methylisoxazolin-5-yl)phenyl)oxazoline (Ex. No. 566) At room temperature, acetaldoxime (30 mg, 0.5 mmol) and N-chlorosuccinimide (67 mg, 1 equivalent) in 3 ml of DMF were stirred for 3 h. 2-(2,6-Difluorophenyl)- 4-(4-ethenylphenyl)oxazoline (43 mg, 0.15 mmol) and triethylamine (46 mg, 0.45 mmol) were then added, and the mixture was stirred for 16 h. Extractive workup with ethyl acetate and column chromatography gave 32 mg of product.

2-(2,6-Difluorophenyl)-4-(4-(3-tert-butylisoxazolin-5-yl)phenyl)oxazoline (Ex. No. 573) 00

O

N At room temperature, pivalaldehyde oxime (51 mg, 0.5 mmol) and N-chlorosuccinimide (67 mg, 1 equivalent) in 3 ml of DMF were stirred for 3 h. 2-(2,6- 5 Difluorophenyl)-4-(4-ethenylphenyl)oxazoline (43 mg, 0.15 mmol) and triethylamine (46 mg, 0.45 mmol) were then added, and the mixture was stirred for 16 h.

Extractive work-up with ethyl acetate and column chromatography gave 30 mg of product.

o 0 2-(2,6-Difluorophenyl)-4-(4-(3-ethoxycarbonylisoxazolin-5-yl)phenyl)oxazoline (Ex. No. 614) At 0°C, triethylamine (0.33 ml, 1.05 equivalents) was added to 2-(2,6-difluorophenyl)-4-(4-ethenylphenyl)oxazoline (570 mg, 2 mmol) and ethyl 2-chloro- 2-hydroxyimino acetate (320 mg, 1.05 equivalents) in 10 ml of dichloroethane, and the mixture was stirred at room temperature for 16 h. Extractive work-up with ethyl acetate and column chromatography gave 420 mg of product.

2-(2,6-Difluorophenyl)-4-(4-(3-(2,2,2-trifluoroethylaminocarbonyl)isoxazolin- ?0 5-yl)phenyl)oxazoline (Ex. No. 628) 2-(2,6-Difluorophenyl)-4-(4-(3-ethoxycarbonylisoxazolin-5-yl)phenyl)oxazoline (769 mg, 1.9 mmol) in 20 ml of ethanol and 6.5 ml of 2N aqueous sodium hydroxide solution was stirred at room temperature for 3 h. The mixture was acidified with 2N hydrochloric acid and then worked up by extraction with dichloromethane. This gave 715 mg of crude acid which could be directly employed further.

47 mg (0.13 mmol) of the crude acid in 2 ml of DMF were admixed with hydroxybenzotriazole (18 mg, 1 equivalent) and N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (25 mg, 1 equivalent). Ethyldiisopropylamine (17 mg, 1 equivalent) in 1 ml of THF and 2,2,2-trifluoroethylamine (0.015 ml) in 1 ml of THF were then added. The mixture was stirred at 50°C for 16 h, and then worked up by extraction with ethyl acetate and column chromatography, giving 41 mg of product.

00 00 43 B. Chemical examples (Tables 1 4) Table 1 Oxazolines of the formula Z= 0, G 3-isoxazolinyl xi 0

N

2 1 Ex. No. X1 TX R6' R Physical data 1 IF F H H

NMR

2 IF IF H OH 3

NMR

3 9 9C 2

H

4 n-C 3

H

7 i-C 3

H

7

NMR

6 n-0 4 Hq 7 i-C 4 Hq 8 S-0 4 Hq 9 t-C 4 H9

NMR

n-C 6

H

13

NMR

11 0H 2 -t-Bu

NMR

12

CH

2 CI

NMR

13

CH

2 B3r

NMR

14 IF IF OH 3

OH

3

C

2

H

16 n-C 3

H

7 1 7 i-C 3

H

7 18

S-C

4

H

9

NMR

19 i-04119

NMR

t-0 4 Hq

NMR

21 n-0 6

HI

3 Ex. No. X' X2 R' RAPhysical data 22 19 1CH 2 t-BU NMR 23 CH 2 CI NMR 24 F F H OCH 3 09 9 g C 2

H

26 O-n-C 3

H

7 27 91O-n-C 4

H

9 28 991,O-i-C 4

H

9

NMR

29 1 9 CN NMR 9 ItCH 2 CN NMR 31 99 g 1CH 2 00H 3 32 11 i 9 CH 2

OC

2

H

5

NMR

33 Tis CH 2 O-n-C 3

H

7

NMR

34 1 9CH 2 O-i-0 3

H

7 91 g 1CH 2 O-n-C 4

H

9

NMR

36 9 11CH 2 O-i-C 4

H

9 37 i 99CH 2

O-S-C

4

H

9 38 T 1CH 2 O-t-C 4

H

9 39 19 i 9CH 2

OCF

2

CF

2 H NMR 97 9 1CH 2 00H 2

CF

3

NMR

41 91 g 1CH 2 O-phenyl NMR 42 01 i H 2 0-2-pyridyl NMR 43 t isCF 3

NMR

44 9 itC 2

F

-t 9 n-C 3

F

7

NMR

46 if t 1n-C 4

F

9

NMR

47 to 1 on-C 5

F

11 48 19 1 1n-C 6

F

13

NMR

49 1 phenyl NMR It2-F-phenyl

NMR

51 293-F-phenyl

NMR

52 9 994-F-phenyl

NMR

Ex. No. X' X% R6'' Physical data 53 2-CI-phenyl

NMR

54 3-CI-phenyl 4-CI-phenyl

NMR

56 2,4-C[ 2 -phenyl 7 'I3,4-C1 2 -phenyl 58 2,6-C1 2 -phenyl

NMR

59 4-Br-phenyl

NMR

2-CF 3 -phenyl

NMR

61 3-CF 3 -phenyl 62 3,5-(CF 3 2 -phenyl

NMR

63 1, TV4-CF 3 -phenyl

NMR

64 2-CH 3 -phenyl

NMR

4-CH 3 -phenyl

NMR

66 2,4-(CH 3 2 -phenyl

NMR

67 2,6-(CH 3 2 -phenyl 68 2,4,6-(CH 3 3 -phenyl

NMR

69 2-CH 3 O-phenyl 4-CH 3 O-phenyl

NMR

71 4-C 2

H

5 0-phenyl 72 4-CF 3 O-phenyl

NMR

73 4-CN-phenyl

NMR

74 4-t-Bu-phenyl

NMR

4-N0 2 -phenyl 76

CH

2 -phenyl

NMR

77 1

CH

2 -(4-F-phenyl) 78

C

2

H

4 Br

NMR

79

CH

2

SCH

3

NMR

CH

2

SOCH

3 81

CH

2

SO

2

CH

3 82

CH

2

SC

2

H

83

CH

2 S-n-C 3

H

7 Ex. No. X7 I- R' RoPhysical data 84

COOCH

3

NMR

COOC

2

H

86

COOCH

2 CF3

NMR

87

COOC

2

H

4

CF

3

NMR

88

C

2

F

4 Br

NMR

89

CONHCH

3 9 TOCONHC 2

H

5

NMR

91

CON(CH

3 2

NMR

92

CON(C

2

H

5 2

NMR

93 99CONH(n-C 3

H

7

NMR

94 9 goCONHCH 2

C

2

F

5

NMR

g goCONHCH 2

C

2

H

3

NMR

96 o goCONH+tC 4 Hq

NMR

97 92CONH-n-C 5

H

1

NMR

98

CONHC

3

H

6

OCH

3

NMR

99

CONHCH

2

C

3

F

7

NMR

100 k oCON

HCH

2 -(2-tetrahydrof uraflyl) NMR 101 goCONH-phenyl 102 11CON H(4-F-phenyl) 103 1, g goCONH(4-CF3 -phenyl)

NMR

104

CONCH

3 (phenyl) 105

CONCH

3 (4-F-phenyl) 106 CON H(4-CI-phenyl) 107 9 9CON

HC

2

H

4 (1 -piperidinyl)

NMR

108 11CONHCH 2

CF

3

NMR

109 11CON

HCH

2 phenyl 110 CON HCH 2 (2,6-F 2 -phenyl)

NMR

go11

CONHCH

2 (4-F-phenyl) 112 CON HC H 2 (4-CF 3 -phenyl) 113 go 9 9CON

HCH

2 (3-C F 3 -phenyl)

NMR

114

CH

2

NHCOCH

3

NMR

Ex. No. X' Xz R Rf Physical data 115 99 o 9CH 2

NHCOCF

3

NMR

116 of 9 oCH 2

NHCOC

2

H

5

NMR

117 99CH 2

NHCOC

2

F

5

NMR

118 91 i 9CH 2 NHCO-n-C 3

H

7 11 o 9 CH 2 NHCO-i-C 3

H

7 120 T itCH 2 NHCO-n-C 3

F

7

NMR

121 to 1 9CH 2

NHCOC

2

H

4

CF

3

NMR

122 9 CH 2 NHCO-t-0 4

H

9 123 91CH 2 NHCOphenyl 124.1

CH

2 NHCO(4-CI-phenyl)

NMR

125

OH

2 NHCO(2-CI-5-pyridy1)

NMR

126 F H H OH 3 127

C

2

H

128 il itf 1 n-C 3

H-

7 1 29 I' 1 1i-C 3

H

7 130 9 91n-0 4

H

9 131 1 i-C 4 H9 1 32 1 S-0 4 Hq 1 33 if t-C 4 Hq 134 go o tn-C 6

H

13 135

CH

2 -t-Bu 136

CF

3 137 C 2

F

1 38 n-0 3

F

7 139 199n-0 4

F

9

NMR

140 if n-C 5 F, 1 141 9 1n-C 6

F

13

NMR

142 phenyl 143 to2-F-phenyl 144 to tof 3-F-phenyt 145 13 t o4-F-phenyl Ex. No. X' 1 2 R R's Physical data 146 1 2-CI-phenyl 147 3-CI-phenyl 148 4-CI-phenyl

NMR

149 12,4-01 2 -phenyl 150 3,4-C1 2 -phenyl 151 2,5-C1 2 -phenyl 152 2,6-C1 2 -phenyl 153 2-CF 3 -phenyl 154 3-CF 3 -phenyl 155 3,5-(0F 3 2 -phenyl 156 4-0F 3 -phenyl 157 2-0H 3 -phenyl 158 4-0H 3 -phenyl 159 2,4-(CH 3 2 -phenyl 160 2,6-(0H 3 2 -phenyl 161 2,4,6-(CH 3 3 -phenyl 162 2-0H 3 0-phenyl 163 4-0H 3 0-phenyl 164 4-C 2 H1 5 0-phenyl 165 4-0F 3 0-phenyl 166 4-ON-phenyl 167 3-N0 2 -phenyl 168 4-N0 2 -phenyl 169 F C1 H OH 3 170 1, C 2

H

1 71 l 9n-C 3

H

7 1 72 i 1i-C 3

H

7 1 73 79n-C 4

H

9 1 74 92i-0 4

H

9 1 75 13S-0 4

H

9 1 76 t-C 4 H9 Ex. No. X' X R Physical data 177 n-C 6

H

13 178 CH 2 -t-Bu 179 CF 3 180

C

2

F

181 Hn-C 3

F

7 182 n-C 4

F

9

NMR

1 83 n-C 5

F

1 184 n-0 6

F

13

NMR

185 phenyl 186 2-F-phenyl 187 3-F-phenyl 188 4-F-phenyl 189 2-CI-phenyl 190 3,3-CI-phenyl 191 4-CI-phenyl NMR 192 2,4-C1 2 -phenyl 193 3,4-C1 2 -phenyl 194 2,5-C1 2 -phenyl 195 2,6-C1 2 -phenyl 196 2-CF 3 -phenyl 197 3-CF 3 -phenyl 198 3,5-(CF3) 2 -phenyl 199 4-CF 3 -phenyl 200 2-C H 3 -phenyl 201 4-CH 3 -phenyl 202 2,4-(CH 3 2 -phenyl 203 H2,6-(CH 3 2 -phenyl 204 2,4,6-(CH 3 3 -phenyl 205 2-0H 3 0-phenyl NMR 206 4-C H 3 0-phenyl 207 4-C 2

H-

5 0-phenyl Ex. No. XY I T R' R" Physical data 208 it 9 s4-0F 3 0-phenyl 209 i 94-ON-phenyl 210 9 3-N0 2 -phenyl 211 9 f4-N0 2 -phenyl 212 Cl H H OH 3 213 990 2

H-

214 99n-C 3

H

7 215 Iti-C 3

H

7 216 79n-C 4 Hg9 217 iti-C 4 H9 218 IS-C 4 H1 9 219 1t-C 4

H.

9 220 n-C 6

HI

3 221 CH 2 -t-Bu 222 CF 3 223 C 2

F

224 n-C 3

F

7 225 n-C 4

F

9

NMR

226 n-0 5

F

11 227 n-C 6

F

13

NMR

228 phenyl 229 2-F-phenyl 230 3-F-phenyl 231 4-F-phenyl 232 2-CI-phenyl 233 3-CI-phenyl 234 4-CI-phenyl

NMR

235 2,4-C1 2 -phenyl 236 3,4-C1 2 -phenyl 237 2,5-C1 2 -phenyl 238 2,6-C1 2 -phenyl Ex. No. X' X2 R' R' Physical data 239 t To2-CF 3 -phenyl 240 1 It3-0F 3 -phenyl 241 11 t t3,5-(CF 3 2 -phenyl 242 99 T t4-0F 3 -phenyl 2 43 to2-0H 3 -phenyl 244 To t 14-0H 3 -phenyl 245 i 12,4-(0H 3 2 -phenyl 246 T 12,6-(0H 3 2 -phenyl 247 2,4,6-(CH 3 3 -phenyl 248 2-CH 3 O-phenyl 249 4-0H 3 0-phenyl 250 to4-0 2

H

5 0-phenyl 251 114-0F 3 0-phenyl 252 914-ON-phenyl 253 3-N0 2 -phenyl 254 to 1 t4-N0 2 -phenyl 255 OH 3 H H OH 3 256 TitC 2

H

257 t 9n-0 3

H

7 25851 i-0 3

H-

7 259 n-C 4

H

9 260 i-C 4 Hq 261 toS-0 4

H

9 262 t-0 4

H

9 263 19 9 9n-0 6

H

13 264

CH

2 -t-Bu 265 CF 3 266

O

2

F

5

NMR

267 ton-C 3

F

7 268 Itn-0 4

F

9 269 191n-0 5

F

11 Ex. No. X1 X? R' R" Physical data 270 2n-0 6

F

13 271 phenyl 272 2-F-phenyl 273 3-F-phenyl 274 4-F-phenyl 275 2-CI-phenyl 276 3-CI-phenyl 277 4-CI-phenyl 278 2,4-C1 2 -phenyl 279 3,4-C1 2 -phenyl 280 2,5-C1 2 -phenyl 261 2,6-C1 2 -phenyl 282 2-CF 3 -phenyl 283 3-CF 3 -phenyl 284 3,5-(CF 3 2 -phenyl 285 4-0F 3 -phenyl 286 2-CH 3 -phenyl 287 4-C H 3 -phenyl 288 2,4-(CH 3 2 -phenyl 289 2,6-(CH 3 2 -phenyl 290 2,4,6-(CH 3 3 -phenyl 291 2-CH 3 O-phenyl 292 4-CH 3 O-phenyl 293 4-C 2

H-

5 0-phenyl 294 4-CF 3 O-phenyl 295 4-ON-phenyl 296 3-N0 2 -phenyl 297 4-N0 2 -phenyl 298 Br H H OH 3 299 i 99C 2 1- 300 99n-C 3

H

7 Ex. No. X2 R s Physical data 301 9 li-0 3

H

7 302 n-C 4

H-

9 303 i-C 4

H-

9 304

S-C

4

H-

9 305 t-C 4 Hg1

NMR

306 n-C 6

H-

13 307

CH

2 +tBu 308 CF 3 309

C

2

F

310 n-C 3

F

7 311 n-C 4 F9

NMR

312 n-0 5

F

1 313 n-C 6

F

13

NMR

314 phenyl 315 2-F-phenyl 316 3-F-phenyl 317 4-F-phenyl 318 2-CI-phenyl 319 3-CI-phenyl 320 4-CI-phenyl 321 2,4-C1 2 -phenyl 322 3,4-C1 2 -phenyl 323 IS2,5-C1 2 -phenyl 324 192,6-C1 2 -phenyl 325 992-CF 3 -phenyl 326 9 3-CF 3 -phenyl 327 113,5-(CF 3 2 -phenyl 328 194-CF 3 -phenyl

NMR

329 132-CH 3 -phenyl 330 4-CH 3 -phenyl 331 2,4-(CH 3 2 -phenyl 00 I00 Ex. No. X X i 2 s Physical data 332 it 1 t2,6-(CH 3 2 -phenyl 333 It I t2,4,6-(CH 3 3 -phenyl 334 1 It2-CH 3 O-phenyl NMR 335 It4-0H 3 0-phenyl 336 4-C 2

H-

5 0-phenyl 337 ~1It 4-C F 3 0-phenyl 338 It4-ON-phenyl 339 I t3-N0 2 -phenyl 340 4-N0 2 -phenyl 341 OH 3

OH

3 H CH 3 342 09 2 1- 343 9 tn-C 3

H-

7 344 i-C 3

H-

7 345 n-0 4

H-

9 346 I iti-C 4

H-

9 347 92 1 tS-C 4

H-

9 348 19 I 9t-0 4

H-

9 349 It i 1n-0 6

H-

13 350 It0H 2 -tBu 351 ofCF 3 352 19 1 tC 2

F

353 It 1 1n-C 3

F

7 354 91n-C 4

F

9

NMR

355 22 n-C 5

F

11 356 I 9n-C 6 F1 3

NMR

357 It 11 9 phenyl 358 i 12-F-phenyl 359 913-F-phenyl 360 if4-F-phenyl 361 992-CI-phenyl 362 i 33-CI-phenyl 00 00 Ex. No. X' X2 R d Physical data 363 I IF4-CI-phenyl

NMR

364 19 9 F2,4-C1 2 -phenyl 365 IF 13,4-01 2 -phenyl 366 I, 1 IF2,5-C1 2 -phenyl 367 I, 1 IF2,6-C1 2 -phenyl 368 2-CF 3 -phenyl 369 3-CF 3 -phenyl 370 3,5-(CF 3 2 -phenyl -371 91 9 94-CF 3 -phenyl 372 19 S 92-CH 3 -phenyl 373 1$ It 1 4-CH 3 -phenyl 374 99 I F2,4-(CH 3 2 -phenyl 375 99 I 92,6-(CH 3 2 -phenyl 376 IF I 92,4,6-(CH 3 3 -phenyl 378 992-CH 3 O-phenyl 379 4-GH 3 O-phenyl 380 11 I 14-C 2

H.

5 0-phenyl 381 IF F -4-CF 3 O-phenyl 382 1, 4-ON-phenyl 383 it 1 F3-N0 2 -phenyl 384 it 9 1 14-N0 2 -phenyl Table 2 Oxazolines, pyrrolines and imidazolines of the formula G 3-isoxazolinyl Ex. No. X2 Z R5Physical data 385 F F OH 2

OH

3 386 19 I, C 2 1- 387 it IT n-0 3

H-

7 388 IT is ,,311 389 IT is, n-C 4 Hg1 390 IT,, i-C 4

H-

9 400 ,S-O 4 H9 401 IT,, t-C 4

H-

9 402 ,n-C 6

H-

13 403 H 2 -t-Bu 404 ,CF 3 405 ,C 2

F

406 ,n-0 3

F

7 407 ,n-0 4

F

9 408 ,n-C 5

F

1 409 9, 1, IT n-C 6

F

13 410 phenyl 411 1, IT IT 2-F-phenyl 412 3-F-phenyl 413 IT 4-F-phenyl 414 1, IT ,9 2-CI-phenyl 415 99 it IT 3-CI-phenyl 416 9, 99 4-Ol-phenyl 417 99 2,4-C[ 2 -phenyl 418 IT 3,4-01 2 -phenyl 00 00 Ex. No. W' 2 zR: Physical data 419 iso2,5-C1 2 -phenyl 420 of g 12,6-C1 2 -phenyl 421 It2-0F 3 -phenyl 422 To3-OF3-phenyl 423 3,5-(CF 3 2 -phenyl 424 4-CF 3 -phenyl 425 2-CH3-phenyl 426 4-CH3-phenyl 427 992,4-(CH 3 2 -phenyl 428 go s 92,6-(CH 3 2 -phenyl 429 go o 92,4,6-(CH 3 3 -phenyl 430 i 9 2-CH 3 O-phenyl 431 91 o 94-CH 3 O-phenyl 432 11 I I4-C 2

H

5 0-phenyl 433 19 9 4-CF3O-phenyl 434 99 9 94-CN-phenyl 435 79 o 3-N0 2 -phenyl 436 9 14-N0 2 -phenyl 437 F H CH 2

OH

3 438 90T 9 2 Hs 439 19 1 9n-C 3

H

7 440 I 9i-C 3

H-

7 441 of 99 1 n-C 4

H

9 442 of 1 1i-C 4

H

9 443 it T oS-C 4 Hq 444 11 1 ot-C 4 Hq 445 99 1 on-C 6

H

13 446 It 1 1CH 2 -t-BU 447 go 1 1CF 3 448 go 1 1C 2 1= 449 is 9 on-C 3

F

7 Ex. No. X' X2 z Physical data 450 n-C 4 F9 451 n-C 5

F

11 452 n-0 6

F

13 453 phenyl 454 3 12-F-phenyl 455 3-F-phenyl 456 4-F-phenyl 457 3,2-CI-phenyl 458 3-CI-phenyl 459 14-CI-phenyt 460 2,4-C1 2 -phenyl 461 313,4-C1 2 -phenyl 462 2,5-C1 2 -phenyl 463 2,6-C1 2 -phenyl 464 2-CF 3 -phenyl 465 3-CF 3 -phenyl 466 3,5-(CF 3 2 -phenyl 467 4-CF 3 -phenyl 468 2-C H 3 -phenyl 469 1 14-C H 3 -phenyl 470 2,4-(CH 3 2 -phenyl 471 2,6-(CH 3 2 -phenyl 472 2,4,6-(CH 3 3 -phenyl 473 2-C H 3 0-phenyl 474 4-C H 3 0-phenyl 475 4-C 2

H-

5 0-phenyl 476 4-CF 3 O-phenyl 477 II4-CN-phenyl 478 3-N0 2 -phenyl 479 4-N0 2 -phenyl 480 F l H 2

CH

3 Ex. No. X' 2 Z R Physical data 481 o 9C 2 1- 482 99n-C 3

H-

7 483 91i-C 3

H

7 484 n-0 4

H-

9 485 I, t 1i-C 4 Hg1 486 1, 1 S-0 4

H-

9 487 99 t ot-C 4

H-

9 488 99 I 9n-0 6 1 1 3 489 09 o t H 2 -tBu 490 11CF 3 491 t 9,C 2 Fs 492 n-C 3

F

7 493 99 1 on-C 4 F9 494 n-C 5

F

11 495 Titn-C 6

F

13 496 9 9phenyl 497 91 1 o2-F-phenyl 498 193-F-phenyl 499 4-F-phenyl 500 19 9 92-CI-phenyl 501 11 1, 9 3-CI-phenyl 502 11 1 94-CI-phenyl 503 99 1 t2,4-C1 2 -phenyl 504 To 0 93,4-C1 2 -phenyl 505 To 1 22,5-C1 2 -phenyl 506 712,6-C1 2 -phenyl 507 9 2-CF 3 -phenyl 508 19 7 13-CF 3 -phenyl 509 9 13,5-(CF 3 )2-phenyl 510 11 t 94-CF 3 -phenyl 511 It 9 92-CH 3 -phenyl Ex. No. X z R Physical data 512 1 it4-CH 3 -phenyl 513 9 12,4-(CH 3 2 -phenyl 514 i 992,6-(CH 3 2 -phenyl 515 2,4,6-(CH 3 3 -phenyl 516 2-0H 3 0-phenyl 517 4-0H 3 0-phenyl 518 4-C 2 H1 5 0-phenyl 519 4-CF 3 O-phenyl 520 4-ON-phenyl 521 3-N0 2 -phenyl 522 4-N0 2 -phenyl 523 F F NCOOEt CH 3 524 9 TyC 2

H

525 9 99n-C 3

H

7 526 2 1iCH 527 Y9n-C 4

H

9 528 i-C 4 Hg9 529 S-C 4 Hq 530 t-C 4

H-

9 531 n-C 6

HI

3 532 CH 2 +tBu 533 CF 3 534 C 2

F

535 n-C 3

F

7 536 n-C 4

F

9 537 n-C 5

F

1 538 n-0 6

F,

3 539 phenyl 540 2-F-phenyl 541 3-F-phenyl 542 4-F-phenyl Ex. No. X Z R 5 Physical data 543 II2-CI-phenyl 544 I,3-CI-phenyl 545 4-CI-phenyl 546 2,4-C1 2 -phenyl 547 9,3,4-C1 2 -phenyl 548 2,5-C1 2 -phenyl 549 II2,6-C1 2 -phenyl 550 2-CF 3 -phenyl 551 3-CF 3 -phenyl 552 3,5-(CF3) 2 -phenyl 553 9,4-CF 3 -phenyl 554 2-CH 3 -phenyl 555 9, 9 ,4-CH 3 -phenyl 556 ,2,4-(CH 3 2 -phenyl 557 ,2,6-(CH3) 2 -phenyl 558 ,2,4,6-(CH 3 3 -phenyl 559 ,2-CH 3 O-phenyl 560 ,4-CH 3 O-phenyl 561 ,4-C 2

H

5 0-phenyl 562 ,4-CF 3 O-phenyl 563 ,4-CN-phenyl 564 ,3-N0 2 -phenyl 565 ,4-N0 2 -phenyl 00 00 Table 3 Oxazolines of the formula Z= 0, G Ex. No. X' X2 R Physical data 566 F F OH 3

NMR

567 01 I 2 1- 5

NMR

568 1 is n-C 3

H-

7

NMR

569 2 o i-C 3

H

7

NMR

570 T 9 n-C 4

H-

9

NMR

571 99 i-C 4

H-

9 572 S-C 4

H-

9 573 t-0 4

H-

9

NMR

574 9 to n-0 5 H,1 1

NMR

575 n-0 6

H-

13 576 1 To CH(0 2

H

5 2

NMR

577 09 H 2 -t-Bu 578 t 92 CH 2

CF

3

NMR

579 9 9 C 2

H-

4 0F 3

NMR

580 9 CF 3 581 09 g 2

F

582 9 9 n-C 3

F

7 583 9 9 n-C 4

F

9 584 1 n-C 5

F

11 585 n-C 6

FI

3 586 phenyl 587 2-F-phenyl 588 t 9 3-F-phenyl 589 1 7 4-F-phenyl NMR Ex. No. X' XZ R Physical data 590 i 99 2-CI-phenyl 591 is 3-CI-phenyl 592 4-CI-phenyl

NMR

593 2,4-C1 2 -phenyl 594 3,4-C1 2 -phenyl 595 2,5-C1 2 -phenyl 596 2,6-C1 2 -phenyl 597 2-CF 3 -phenyl 598 3-CF 3 -phenyl 599 3,5-(CF3) 2 -phenyl 600 4-CF 3 -phenyl

NMR

601 2-CH 3 -phenyl 602 4-CH 3 -phenyl 603 2,4-(CH 3 2 -phenyl 604 2,6-(CH 3 2 -phenyl 605 2,4,6-(CH 3 3 -phenyl

NMR

606 2-CH 3 O-phenyl 607 4-CH 3 O-phenyl 608 4-C 2

H

5 0-phenyl 609 4-CF 3 O-phenyl 610 4-ON-phenyl 611 3-N0 2 -phenyl 612 4-N0 2 -phenyl 613 COOH

NMR

614 COOC 2

H

5

NMR

615 COOCH 2

CF

3

NMR

616 COOC 2

H-

4

CF

3

NMR

617 CONH 2 618 CONHCH 3 619 CONHC 2

H

5

NMR

620 CON(CH 3 2 Ex. No. X1~ Xz R Physical data 621 1, 1 CON(C 2

H

5 2

NMR

622 itCONH(n-C 3

H

7

NMR

623

CONHCH

2

C

2

F

5

NMR

624 t to CONH-t-C 4 Hg

NMR

625 99 CONHCH 2

C

2

H

3

NMR

626

CONHCH

2

C

3

F

7

NMR

627 1 9 CONH-s-C 5 H11

NMR

628 1 CONHCH 2

CF

3

NMR

629 9 CONHC 3

H

6 00H 3

NMR

630 I 9 CON HCH 2 -(2-tetrahydrof uranyl) NMR 631 i to CONHCH 2 -(2,6-F 2 -phenyl)

NMR

632 99CON HCH 2 -(4-F-phenyl) 633 t of CON HCH 2 -(3-CF3-phenyl)

NMR

634 t 1 CON HCH 2 -(4-CF 3 -phenyl) 635 I 9 CONH(2,5-F 2 -phenyl) 636 I to CONH(4-F-phenyl) 637 9 CONH(3-CF 3 -phenyl) 638 1 CONH(4-CF3-phenyl) 639 F H OH 3 640 C 2 1- 641 n-0 3

H

7 642 99 i-C 3

H

7 643 n-C 4 Hq 644 19 i-C 4 Hg 645 t f S-C 4

H-

9 646 T 1 t-C 4 Hq 647 n-C 5

H

11 648 n-C 6

H

13 649 CH(0 2

H

5 2 650 o 1 CH 2 -tBu 651 CH 2

CF

3 Ex. No. X' X Physical data 652 C 2

H

4

CF

3 653 CF 3 654

C

2

F

655 n-C 3

F

7 656 n-C 4 F9 657 n-C!F 1 i 658 n-C 6

FI

3 659 phenyl 660 2-F-phenyl 661 3-F-phenyl 662 4-F-phenyl 663 2-CI-phenyl 664 3-CI-phenyl 665. 4-CI-phenyl 666 2,4-C1 2 -phenyl 667 3,4-C1 2 -phenyl 668 2,5-C1 2 -phenyl 669 2,6-C1 2 -phenyl 670 2-C F 3 -phenyl 671 3-CF 3 -phenyl 672 3,5-(CF 3 2 -phenyl 673 4-CF 3 -phenyl 674 2-CH 3 -phenyl 675 4-C H 3 -phenyl 676 2,4-(CH 3 2 -phenyl 677 2,6-(CH 3 2 -phenyl 678 2,4,6-(CH 3 3 -phenyl 679 2-C H 3 0-phenyl 680 4-C H 3 0-phenyl 681 4-C 2

H

5 0-phenyl 682 4-C F 3 0-phenyl Ex. No. iV X2 R Physical data 683 4-C N-phenyl 684 3-N0 2 -phenyl 685 4-N0 2 -phenyl 686 F H OH 3 687 09 9 2

H-

688 91 n-C 3

H-

7 689 i-C 3

H

7 690 n-C 4

H-

9 691 i-C 4 Hg 692 S-C 4

H-

9 693 t-C 4 H9 694 n-C 5

H-

11 695 n-0 6 H1 3 696 CH(0 2

H

5 2 697 0H 2 -tBu 698 0H 2 0F 3 699 C 2

H-

4

CF

3 700 CF 3 701 0 2

F

702 n-0 3

F

7 703 n-0 4

F

9 704 n-C 5

F

1 705 -63 706 phenyl 707 2-F-phenyl 708 3-F-phenyl 709 4-F-phenyl 710 2-CI-phenyl 711 3-CI-phenyl 712 4-CI-phenyl 713 2,4-C1 2 -phenyl Ex. No. X' X2 R Physical data 714 3,4-C1 2 -phenyl 715 2,5-C1 2 -phenyl 716 2,6-C1 2 -phenyl 717 2-CF 3 -phenyl 718 3-0F 3 -phenyl 719 3,5-(CF 3 2 -phenyl 720 4-CF 3 -phenyl 721 2-CH 3 -phenyl 722 4-CH 3 -phenyl 723 2,4-(CH 3 2 -phenyl 724 2,6-(0H 3 2 -phenyl 725 2,4,6-(CH 3 3 -phenyl 726 2-CH 3 O-phenyl 727 4-0H 3 0-phenyl 728 1 f 4-0 2 H1 5 0-phenyl 729 194-0F 3 0-phenyl 730 11 4-ON-phenyl 731 3-N0 2 -phenyl 732 4-N0 2 -phenyl 733 C1 H OH 3 734 0 2

H

735 n-C 3

H

7 736 i-0 3

H

7 737 n-C 4 Hq 738 i-C 4 H9 739 S-C 4 Hg1 740 t-0 4

H

9 741 n-0 5

H

13 742 n-0 6

H

13 743 g 9 CH(C 2

H

5 2 744 1 9 CH 2 -t-Bu Ex. No. X1 X? Physical data 745 CH 2

CF

3 746 C 2

H-

4

CF

3 747 CF 3 748 C 2

F

749 t to n-C 3

F

7 750 9 n-0 4

F

9 751 9 To n-C 5

F

11 752 9 o n-C 6

F

1 3 753 t to phenyl 754 go t 2-F-phenyl 755 it T 3-F-phenyl 756 9 4-F-phenyl 757 11 It 2-CI-phenyl 758 9 1 3-CI-phenyl 759 t 9 4-CI-phenyl 760 9 It 2,4-C1 2 -phenyl 761 193,4-C1 2 -phenyl 762 is2,5-C1 2 -phenyl 763 992,6-C1 2 -phenyl 764 to2-CF 3 -phenyl 765 193-CF 3 -phenyl 767 1 It 3,5-(CF 3 2 -phenyl 768 4-CF 3 -phenyl 769 01 2-CH 3 -phenyl 770 t 9 4-CH 3 -phenyl 771 i 9 2,4-(CH 3 2 -phenyl 772 9 1 2,6-(CH 3 2 -phenyl 773 9 to 2,4,6-(CH 3 3 -phenyl 774 1 91 2-CH 3 O-phenyl 776 114-CH 3 O-phenyl 777 9, 4-C 2

H

5 0-phenyl Ex. No. X1 X2 R Physical data 778 4-CF 3 O-phenyl 779 1 4-CN-phenyl 780 3-N0 2 -phenyl 781 4-N0 2 -phenyl 782 OH 3 H OH 3 783 0 2

H

784 n-0 3

H

7 785 i-0 3

H

7 786 n-C 4

H

9 787 i-C 4

H-

9 788 S-C 4

H-

9 789 t-0 4

H-

9 790 n-C 5

H-

11 791 n-0 6

H-

13 792 OH(C 2

H

5 2 793 CH 2 -tBu 794 0H 2 0F 3 795 O 2

H-

4 0F 3 796 CF 3 797 C 2

F

798 n-0 3

F

7 799 n-0 4

F

9 800 n-C 5

F

1 801 n-0 6

F

13 802 phenyl 803 2-F-phenyl 804 3-F-phenyl 805 4-F-phenyl 806 2-CI-phenyl 807 3-CI-phenyl 808 4-Ol-phenyl Ex. No. X1 X2 R Physical data 809 2,4-C1 2 -phenyl 810 3,4-C1 2 -phenyl 811 2,5-C1 2 -phenyl 812 2,6-01 2 -phenyl 813 2-CF 3 -phenyl 814 3-C F 3 -phenyl 815 3,5-(0F 3 2 -phenyl 816 4-0F 3 -phenyl 817 2-0H 3 -phenyl 818 4-CH 3 -phenyl 819 2,4-(CH 3 2 -phenyl 820 2,6-(CH 3 2 -phenyl 821 2,4,6-(CH 3 3 -phenyl 822 2-C H 3 0-phenyl 823 4-CH 3 O-phenyl 824 4-C 2

H-

5 0-phenyl 825 4-0F 3 0-phenyl 826 4-CN-phenyl 827 3-N0 2 -phenyl 828 4-N0 2 -phenyl 829 Br H OH 3 830 29 C 2

H

831 19 n-C 3

H

7 832 i-0 3

H-

7 833 n-C 4

H

9 834 i-C 4

H

9 835

S-C

4 Hq 836 t-C 4

H

9 837 n-C 5

H-

11 838 n-C 6

H

13 839 CH(C 2 H5) 2 Ex. No. X' X2 R Physical data 840 19CH 2 -tBu 841 CH 2

CF

3 842 0 2

H

4

CF

3 843 CF 3 844 C 2 Fs 845 n-C 3

F

7 846 n-C 4 Fq 847 n-C 5

F

11 848 n-C 6

F

13 849 phenyl 850 2-F-phenyl 851 3-F-phenyl 852 4-F-phenyl 853 2-CI-phenyl 854 3-CI-phenyl 855 4-CI-phenyl 856 2,4-C1 2 -phenyl 857 3,4-C1 2 -phenyl 858 2,5-C1 2 -phenyl 859 2,6-C1 2 -phenyl 860 2-CF 3 -phenyl 861 3-CF 3 -phenyl 862 3,5-(CF3)2-phenyl 863 4-CF 3 -phenyl 864 2-CH 3 -phenyl 865 4-CH 3 -phenyl 866 2,4-(CH 3 2 -phenyl 867 2,6-(CH 3 2 -phenyl 868 2,4,6-(CH 3 3 -phenyl 869 2-C H 3 0-phenyl 870 4-CH 3 O-phenyl 871 9 1 4-C 2

H

5 0-phenyl 872 i 9 4-CF 3 O-phenyl 873 194-ON-phenyl 874 3-N0 2 -phenyl 875 4-N0 2 -phenyl Table 4 Pyrrolines and imidazolines of the formula G Ex. No. X1 x2 ZR5 Physical data 876 F F OH 2

OH

3 877 1-C 2

H

878 n-0 3

H

7 879 H Ni-0 3

H

7 880 n-0 4

H

9 881 i-C 4

H

9 882 HS-C 4

H

9 883 t-0 4 Hq 884 n-0 6

H

13 885 CH 2 -t-Bu 856 CF 3 887 C 2

F

888 n-C 3

F

7 889 n-0 4 F7 9 890 n-C 5 F~l 891 n-C 6

F

13 892 phenyl Ex. No. X ZR Physical data 893 11 I 72-F-phenyl 894 3,3-F-phenyl 895 4-F-phenyl 896 2-CI-phenyl 897 313-CI-phenyl 898 3,4-CI-phenyl 899 312,4-C1 2 -phenyl 900 3,4-C1 2 -phenyl 901 2,5-C1 2 -phenyl 902 2,6-C1 2 -phenyl 903 2-CF 3 -phenyl 904 313-CF 3 -phenyl 905 3,5-(CF 3 2 -phenyl 906 4-CF 3 -phenyl 907 ,32-CH 3 -phenyl 908 4-CH 3 -phenyl 909 2,4-(CH 3 2 -phenyl 910 2,6-(CH 3 2 -phenyl 911 2,4,6-(CH 3 3 -phenyl 912 2-CH 3 O-phenyl 913 4-CH 3 O-phenyl 914 4-C 2

H-

5 0-phenyl 915 4-CF 3 O-phenyl 916 4-ON-phenyl 917 3-N0 2 -phenyl 918 4-N0 2 -phenyl 919 F H OH 2

OH

3 920 C 2

H-

921 n-C 3

H-

7 922 i-0 3

H

7 923 n-0 4

H-

9 Ex. No. X2 z Physical data 924 i-C 4 Hg1 925

S-C

4 Hg1 926 t-0 4

H-

9 927 n-C 6

H-

13 928

CH

2 -tBu 929 CF 3 930

C

2

F

931 n-C 3

F

7 932 n-C 4 F9 933 n-C 5

F,

934 n-C 6

F

13 935 phenyl 936 2-F-phenyl 937 Ii3-F-phenyl 938 4-F-phenyl 939 52-CI-phenyl 940 ,,3-CI-phenyl 941 4-CI-phenyl 942 2,4-C1 2 -phenyl 943 3,4-01 2 -phenyl 944 2,5-C1 2 -phenyl 945 ,,2,6-C1 2 -phenyl 946 2-CF 3 -phenyl 947 II3-CF 3 -phenyl 948 ,,3,5-(CF 3 2 -phenyl 949 '54-CF 3 -phenyl 950 2-CH 3 -phenyl 951 4-CH 3 -phenyl 952 ,,2,4-(CH 3 2 -phenyl 953 5,2,6-(CH 3 2 -phenyl 954 ,2,4,6-(CH 3 3 -phenyl Ex. No. XT X2 ZR5 Physical data 955 19 o 2-0H 3 0-phenyl 956 3,4-CH 3 O-phenyl 957 1 19 I 4-C 2

H

5 0-phenyl 958 4-CF 3 O-phenyl 959 3,4-ON-phenyl 960 3 313-N0 2 -phenyl 961 19 1I 4-N0 2 -phenyl 962 F C1 OH 2

OH

3 963 1 I I 2 1-1 964 11n-C 3

H-

7 965 91 99 I i-C 3

H-

7 966 99 I Fn-C 4

H-

9 967 IF I 9i-C 4

H-

9 968 19 I 1S-C 4 Hg1 969 99 1 Ft-C 4

H-

9 970 IF 1 9n-0 6

H

13 971 91 1 FCH 2 -t-Bu 972 IF 9 tCF 3 973 C 2

F

974 19 I fn-C 3

F

7 975 IIFn-C 4

F

9 976 Is T sn-CsF 1 977 IF I Fn-C 6

F

13 978 9 91phenyl 979 9, 2-F-phenyl 980 1 IF3-F-phenyl 981 9 9 4-F-phenyl 982 it I 92-CI-phenyl 983 IF 3-CI-phenyl 984 1 IF 4-CI-phenyl 985 99 1" [,2,4-C1 2 -phenyl 00 00 Ex. No. X2 z R C2pe Physical data 986 ot4-to toh3,4 987 it 9 o2,5-01 2 -phenyl 988 t 12,6-01 2 -phenyl 989 2-0F 3 -phenyl 990 to 9 o3-CF 3 -phenyl 991 19 9 13,5-(0F 3 2 -phenyl 992 t o4-0F 3 -phenyl 993 I' to t 2-C H 3 -phenyl 994 It 1 -4-0H 3 -phenyl 995 11 19 t 2,4-(CH 3 2 -phenyl 996 go 9 12,6-(CH 3 2 -phenyl 997 9?T 9 ,4,6-(0H 3 3 -phenyI 998 112-0H 3 0-phenyl 999 99 I 4-CH 3 O-phenyl 1001 to 11 i 4-C 2 H1 5 0-phenyl 1002 99 g o4-CF 3 O-phenyl 1003 To 9 94-ON-phenyl 1004 91 to 1 3-N0 2 -phenyl 1005 71 0 94-N0 2 -phenyl 1006 F F NCOOEt OH 3 1007 0 9 T 2

H

1 008 99 91 I n-C 3

H-

7 1009 91 o 9i-C 3

H

7 1010 1TOn-C 4 Hq 1011 29i-0 4

H

9 1012 to i 9S-0 4

H-

9 1013 91 9 tt-C 4

H

9 1014 19 i on-0 6

H

13 1015 of 1 tCH 2 -t-Bu 1016 1ToCF 3 1017 C 2

F

Ex.No X2~ Physical data 1018 t ofn-C 3

F

7 1019 n-C 4 F9 1 020 n-C 5

F

11 1021 9 on-C 6 F1 3 10221hey 10232--pey 1024 3phenyl 10253--pey 1026 2-C-phenyl 1027 3-C-phenyl 1028 4-I-hey 1029 to4-C-phenyl 1030 too-C 2 -phenyl 1031 To,

-C

2 -phenyl 102 to-C 2 -phenyt 1033 2,-C 3 -phenyl.

1034 o t 3,-C 3 -phenyl 1031 1,_to t3,5-(CF 2 -phenyl 1036 4, o t 3 -phenyl 1037 t o t 2-CH 3 -phenyl 1038 4-CH 3 -phenyl 1039 o 9 2,4-(CH 3 2 -phenyl 1040t 2,-C 3 -phenyl 10471,, o 9 2,-CH 3 3 -nyl 1042 1,_to t2-CH 3 -phenyl 103 1, o4-CH 3 -phenyl 1044 9 4,-CHH 5 -phenyl 1045 9 4-CF 3 O-phenyl 1046 914-C N-phenyl 1047 11 to 9 3-N0 2 -phenyl 1048 99 1 14-N0 2 -phenyl oo C. Formulation examples a) A dusting powder is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc, as inert substance, and 5 comminuting the mixture in an impact mill.

b) A wettable powder which is readily dispersible in water is obtained by mixing parts by weight of active compound, 65 parts by weight of kaolincontaining quartz, as the inert substance, 10 parts by weight of potassium 00 0 ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate, as wetting and dispersing agent, and grinding the mixture in a pinned disk mill.

c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture to a fineness of below microns in a grinding bead mill.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of !0 active compound, 75 parts by weight of cyclohexane, as the solvent, and parts by weight of ethoxylated nonylphenol (10 EO), as theemulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granule carrier material, such as attapulgite, pumice granules and/or quartz sand. A suspension of the wettable powder from Example b) having a solids content of 30% is expediently used, and this is sprayed onto the surface of attapulgite granules and the components are dried and mixed intimately. The weight content of the wettable powder is approximately and that of the inert carrier material is approximately 95% of the finished granules.

D. Biological examples Example 1: effect on the spider mite Tetranychus urticae Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into C) 5 brown glass bottles filled with tap water and subsequently populated with approximately 100 spider mites (Tetranychus urticae). Plant leaf and spider mites S are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, plants and animals are S stored in a climatized chamber (16 hours of light/day, 250C, 40-60% relative 00 S0 atmospheric humidity). After 6 days of storage, the mortality of the preparation on all stages of the spider mites is determined. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 1, 2, 5, 9, 12, 22, 23, 32, 33, 35, 39, 41,42, 43, 45, 46, 48, 49, 52, 63, 76, 79, 87, 90, 91,92, 96, 97, 99, 108, 110, 113, 117, 120, 569, 570, 573, 574, 576, 578, 579, 589, 600, 605, 619, 623, 624, 625, 626, 628, 629, 630, 631 effect a mortality of 80-100%.

Example 2: effect on the aphid Aphis fabae Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into !0 brown glass bottles filled with tap water and subsequently populated with approximately 100 aphids (Aphis fabae). Plant leaf and aphids are then dipped for seconds into an aqueous solution of the formulated preparation to be examined.

After the solution has run off, plants and animals are stored in a climatized chamber (16 hours of light/day, 250C, 40-60% relative atmospheric humidity). After 6 days of storage, the mortality of the preparation on all stages of the aphid is determined. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 96 and 103 effect a mortality of 80-100%.

Example 3: effect on the egg-larval stage of Heliothis virescens A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of nutrient medium is prepared. Filter paper sections containing approximately 0o 24-hour-old eggs of the tobacco budworm (Heliothis virescens) are dipped for seconds into an aqueous solution of the formulated preparation to be examined and subsequently placed into the Petri dish. A further 200 pI of the aqueous solution are distributed over the nutrient medium. After the Petri dish has been closed, it is C 5 stored in a climatized chamber at about 25°C. After 6 days of storage, the mortality of the preparation on the eggs and any larvae hatched from them is determined. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 1, 5, 9, 20, 22, 28, 39, 45, 46, 48, 49, 52, 63, 94, 103, S 116, 568, 567, 573, 579, 589, 619, 623 effect a mortality of 80-100%.

00 0 c Example 4: feeding effect on the butterfly larvae Heliothis virescens Nutrient medium (freeze-dried cube) is dipped into an aqueous solution of the formulated preparation to be examined and then placed into a Petri dish. Ten L2 larvae of the tobacco budworm (Heliothis virescens) are then added. The Petri dish is then closed with a lid. The effect of the preparation on the larvae is determined after 4 days of storage at about 23°C. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 2, 9, 13, 20, 22, 28, 29, 30, 32, 35, 39, 40, 41,42, 43, 45, 46, 48, 49, 52, 63, 76, 78, 91,93, 94, 95, 98, ?0 103, 114, 116, 117,120,121,124, 125,567,573,589,600,605,613,614,615, 619, 621, 623, 624, 629 effect a larvae mortality of 80-100%.

Example 5: feeding effect on the butterfly larvae Spodoptera litoralis Nutrient medium (freeze-dried cube) is dipped into an aqueous solution of the formulated preparation to be examined and then placed into a Petri dish. Ten L2 larvae of the Egyptian cotton leaf worm (Spodoptera litoralis) are then added. The Petri dish is then closed with a lid. The effect of the preparation on the larvae is determined after 4 days of storage at about 23°C. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 5, 9, 12, 28, 29, 30, 35, 39, 40, 41,42, 43, 45, 46, 48, 52, 63, 87, 90, 91,92, 94, 97, 98, 99, 100, 103, 107, 113, 117, 120, 125, 566, 567, 573, 574, 589, 600, 613, 614, 619, 626 effect a larvae mortality of 80-100

Claims (13)

1. 2. A compound of the formula as claimed in claim 1, where the symbols and indices are as defined below: 00 X is halogen, cyano, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 3 )-haloalkyl, (C1-C4)-alkoxy or (Cl-C 3 )-haloalkoxy, m is 0 or 1, n is 1,2 or 3, Z is oxygen or CH 2 R 1 is H, halogen, (C1-C 4 )-haloalkyl, (Cl-C4)-alkyl, (C1-C4-alkoxy or (Cl-C4)- haloalkoxy, O G is 00 (R)t R or t is 0,1, 2 or 3, R 5 is identical or different a) halogen, CN, NO 2 b) a straight-chain or branched alkyl group having 1 to 12 carbon atoms, where one or more (CH 2 groups are optionally replaced by -NR 6 -CH=CH-, aryldiyl, heterocyclyldiyl, (C3-C)-cycloalkyl or (C3-C 8 )-cycloalkenyl, with the proviso that chalcogens may not be adjacent to one another, where individual hydrogen atoms are optionally replaced by halogen; c) in the case of two radicals R 5 located in the c-position, the radicals are also where Y is (=NOR 6 or (=CR26); with the proviso that the radical(s) R 5 together do not comprise more than one ring system having five or more members; R 6 is (Ci-C 4 )-alkyl, phenyl or benzyl; Aryl is a carbocyclic aromatic radical having 6 to 14 carbon atoms; Heterocyclyl is a heteroaromatic or heteroaliphatic ring system, where "heteroaromatic ring system" is to be understood as meaning an aryl radical where at least one CH group is replaced by N and/or at least two adjacent CH 84 groups are replaced by S, NH or 0, and "heteroaliphatic ring system" is to be 00 0 understood as meaning a (C 3 -C 8 )-cycloalkyl radical in which at least one ci carbon unit is replaced by 0, S or a group NR"1 and R 11 is hydrogen, (01-04)- alkyl, (0 1 -C 4 )-alkoxy or aryl; where the cyclic radicals in the meaning of R 5 R 6 are optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, thio, (Cl-0 4 )-alkyl, (0 1 -0 4 )-haloalkyl, (0 3 -CB)-cycloalkyl, (C 1 -0 4 )-alkoxy, (0 1 -C4)-haloalkoxy, -C 4 )-alkylthio, (Ci -C4)-haloalkylthio, (Ci -C 4 )-alkylamino, 00 (Cl-C 4 )-haloalkylamino and (Cl-C 4 )-alkanoyl. R 6 is (C1-C 4 )-alkyl, unsubstituted-or substituted phenyl or unsubstituted-ef substituted benzyl. below A compound as claimed in claim 2, where the groups R 5 are as defined R' is CN, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, (C1-C6)-alkyl, (C1-C 6 )-alkenyl, (C 1 -C 6 )-haloalkyl, (Ci-C 6 )-haloalkenyl, -(C 1 -C 6 )-alkanediyl-aryl, where the aryl group is unsubstituted or substituted and where one -CH 2 unit is optionally replaced by -C(O)-NR 10 NRi'-(CO), NR 0 or O; R 1 i is H, (C1-C 6 )-alkyl, (Ci-Cs)-haloalkyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl.
2. 4. A compound as claimed in one or more of claims 1 to 3, where Qis X, F Br
3. 6- F CI' CH3 F CI CH 3 or A compound as claimed in one or more of claims 1 to 4, selected from the group consisting of (11) to (128): F 86 (11) (12) (13) Rlm cl 87 RIM RIM OH 3 (14) (1 6) RIM OH 3 IRI RIM RIM RIM (110) (112) RIM CH 3 (113) RIM (114) CH 3 IR'm (115) RIM F 89 00 00 Rlm (116) Rlm Rim Rim (120) (121) CH 3 Rlm OH 3 Rlm F 00 R (122) Rlm A 5 (123) 00 Rm R (124) Rlm R C (125) Rlm Br (126) CH, (127) Rm H 3 (128) CH, 9± where R'm and R 5 are as defined in claim 2. 6. A process for preparing compounds of the formula as claimed in one or more of claims 1 to 5, where a) to prepare compounds having a 3-isoxazinyl radical, an oxime of the formula (II), 'O H in which X and Z are as defined for formula (I) is reacted with a chlorinating agent to give a compound of the formula (1II) Sz Hal in which Hal is halogen and then reacted further with an olefin of the formula (IV), (IV) in which R 5 and t are as defined above; or b) (VII) 92 to prepare compounds having a 5-isoxazinyl radical, an olefin of the formula (VII) in which Z and R 5 are as defined in claim 2, is reacted with a halogenated oxime of the formula (VIII) Hal H l (VIII) H.oN where R 5 is as defined in claim 2.
4. 7. A pesticide, comprising at least one compound as claimed in any of claims 1 to 5 and at least one formulation auxiliary.
5. 8. An insecticidal, acaricidal and/or nematocidal composition as claimed in claim 7, comprising an effective amount of at least one compound as claimed in one or more of claims 1 to 5 together with additives or auxiliaries conventionally used for this application.
6. 9. A pesticide, comprising an insecticidally, acaricidally and/or nematicidally effective amount of at least one compound as claimed in one or more of claims 1 to and at least one further active compound, together with auxiliaries and additives conventionally used for this application.
7. 10. A composition for use in timber protection or as a preservative in sealants, in paints, in cooling lubricants for metal working or in drilling and cutting oils, comprising an effective amount of at least one compound as claimed in any of claims 1 to 5 together with the auxiliaries or additives conventionally used for this 00 application. 0
8. 11. The use of a compound as claimed in one or more of claims 1 to 5 or of a composition as claimed in claim 7, 8 or 9 for preparing a veterinary medicament.
9. 12. A process for preparing a composition as claimed in one or more of claims 7 to 11, which comprises combining the active compound and the other additives and formulating them to give a suitable use form. 0 13. The use of a compound as claimed in one or more of claims 1 to 5 or of a composition as claimed in one or more of claims 7, 8 and 9 as a timber preservative or as a preservative in sealants, in paints, in cooling lubricants for metal working and/or in drilling and cutting oils.
10. 14. The use of compounds as claimed in one or more of claims 1 to 5 or of a composition as claimed in one or more of claims 7, 8, 9 and 10 for controlling harmful insects, Acarina, molluscs and nematodes.
11. 15. A method for controlling harmful insects, Acarina, molluscs and/or nematodes, in which an effective amount of one or more compounds as claimed in one or more of claims 1 to 5 or of a composition as claimed in one or more of claims 7, 8, 9 and 10 is brought into contact with the organisms mentioned.
12. 16. A method for controlling harmful insects, Acarina, molluscs and/or nematodes as claimed in claim 15, in which an effective amount of a compound as claimed in any of claims 1 to 5 or of a composition as claimed in any of claims 7, 8 and 9 is applied to these organisms or to the plants, areas or substrates infested with them.
13. 17. Seed, comprising or coated with an effective amount of a compound as claimed in any of claims 1 to 5 or of a composition as claimed in any of claims 7, 8 or 9.