DD264842A5 - SCHAEDLINGSBEKAEMPFUNGSMITTEL - Google Patents

Abstract

The invention relates to pesticides which contain substituted N-methylisoxazolidines of the formula (I) in which R 1, R 2 and R 3 have the meanings given in the description, their acid addition salts and their geometrical and optical isomers as active ingredients. Formula (I)

Description

Berlin, the 21 · 12 * 1987 69 441/18

pesticide Field of application of the invention

The invention relates to pesticides containing novel substituted N-Methyllsoxazolldine as active ingredients ·

Characteristic of the known state of Teohni.k

It is ready known that certain Isoxazolidone, such as the 5-benzyl-5-ethoxyoarbony1-2-t-butylisoxazolidin, insecticidal and ^fungicidal> effectiveness (cf., "z" B · DE-OS 34 18 935) ·

The effectiveness of these compounds vorbekann ^ s 1st jedooh especially at low application rates and concentrations \\ not in all areas entirely satisfactory ·

O Furthermore, certain substituted N-Methyllsoxazolidlne, such as the 2-methyl-3-phenyl-5- (1-piperidinylmethyD-isoxazolidin or 2-methyl-3-phenyl-5 "(4-morpholinylmothyD-isoxazolidin known (see * Japan · Fat · JP 43/14 2i5 of 15 * 06.1968), It is not yet known about the efficacy of these prior known deposits against Sohädlinge

Object of the invention Surprisingly, the N-methyl-

isoxazolidone a significantly better efficacy against insects and piIzHohe Sohaderreger than the known from the state of Teohnlk isoxazolidines, such as the 5- benzyl-5-ethoxycarbonyl-2-t-butyl-is-oxazolldln, which are ohemisoh and effectively obvious connections ·

Explanation of the essence of the invention

There have been novel substituted N-methylisoxazolidines of the general formula (1),

(I)

in which each represents alkyl, aryl or heteroaryl,

Each R ¹ is optionally substituted alkyl, Oyolo

Each R 2 and R 4 'independently of one another represent hydrogen, in each case optionally substituted alkyl, alkenyl, cycloalkyl and aryl, or together with the nitrogen atom to which they are bonded represent an optionally substituted, saturated hetero-oxyl, optionally may contain further heteroatoms, and their acid addition salts, except the compounds 2-methyl-3-phenyl-5- (plperidin-1-yl-methyl) isoxazolidine and 2-methyl-3-phenyl-5- (morpholine-4 ylmethyl) -lsoxazolldin ·

The compounds of the formula (I) may optionally be used as geometric and / or optical isomers or isomeric mixtures of different composition.

Both the pure isomers "1" and the mixtures of isomers are claimed according to the invention under the formula (I). In the following, the formula (I) is always used, all forms being included. "

Furthermore, it has been found that the novel substituted N-methylisoxazolidines of the general formula (I) *

_cS ^ ch ₂ -n < _r3 cn

in which

R * is in each case optionally substituted alkyl, Cycloalkyl, aryl or heteroaryl is and

R ² and R ³ are each independently hydrogen, each optionally substituted alkyl, alkenyl, cyc) alkyl or aryl, or optionally together with the nitrogen atom to which they are attached, represent an optionally substituted, saturated heterocycle Further

Heteros-tome r can hold, except those Compounds 2-methyl-3-pheny1-5- (piperidine-1 ·

yl-methyl) -isoxazolidine and 2-methyl-3-phenyl-5- (morpholin-4-ylmethyl) -isoxazolidine,

as well as their acid addition salts, when one gets 35

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(a) nitrones of formula (II), 6

"nC

(II) CH ₃

in which

K ^{1 has} the abovementioned meaning, with allylamines of the formula (III)

R ^{z 1} CH ₂ OH-CH ₂ -N <(III)

in which

R ^ and r3 have the meaning given above »

25 optionally in the presence of a diluent, or if

(b) oxazolidines of the formula (IV),

(IV)

CH ₃ CH ₂ -X ¹

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in which

R ^{1 has} the meaning given above and X * for an electron attracting leaving group

stands "10 with amines of the formula (V) ,

HN < _m (V) R ³

in which

R ² and R ^{3 have} the meaning given above ι

optionally in the presence of a diluent, and optionally in the presence of an acid binder and optionally in the presence of a catalyst umuetzt or if

(C) the obtainable by process (a) or (b) substituted N-methylisoxazolidines of the formula (Ia) ι

I I there)

CH ₃ CH ₂ -NH-R ² in which

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1 2 R and R have the meaning given above, with

Alkylating agents of the formula (VX),

(VI) in which

Br is in each case optionally substituted alkyl, alkenyl or oxyalkyl and

O ₂

X is an electron attracting leaving group,

if appropriate in the presence of a diluent, and if appropriate in the presence of an acid binder and, if appropriate, in the presence of a catalyst and, if appropriate, subsequently adding an acid.

Sohließlioh was found that the new substituted N-methylisoxazolidines have good activity against pests «

The erf indungsgemaflen substituted N-Methylisoxazoli-S dine are generally defined by the formula (I) "Preferred are compounds of formula (I) ₁ in which

R ^{1 represents} straight-chain or branched alkyl having 1 to 18 carbon atoms "for optionally mono- to polysubstituted by identical or different alkyl having 1 to 6 carbon atoms cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to β carbon atoms in the straight-chain or branched alkyl moiety or if appropriate in the aryl moiety monosubstituted to polysubstituted by identical or different substituents aralkyl having 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and 6 to 10 carbon atoms in the aryl moiety, suitable aryl substituents being: halogen * in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkoximinoalkyl , Halogenoalkyl, haloalkoxy or haloalkylthio having in each case 1 to 4 carbon atoms in the individual alkyl moieties and optionally 1 to 9 identical or different halogen atoms; also represents optionally mono- to polysubstituted, identically or differently by alkyl having 1 to 6 carbon atoms substituted cycloalkyl having 3 to 7 carbon atoms or optionally mono- to polysubstituted by identical or different substituents phenyl, being suitable as substituents: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkyl

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Halogenoalkyl, haloalkoxy or haloalkylihio having in each case 1 to 6 carbon atoms and optionally 1 to 9 identical or different halogen atoms, amino «in each case straight-chain or branched alkylamino, dialkylamino or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties;

furthermore, in each case optionally monosubstituted to polysubstituted or differently substituted oc-naphthyl or ft-naphthyl, suitable substituents being in each case: halogen each being straight-chain or branched alkyl or alkoxy y ) having in each case 1 to 4 carbon atoms; and close

Lich for an optionally mono- to polysubstituted, identically or differently by alkyl having 1 to 6 carbon atoms and / or halogen-substituted 5-membered ring or 6-membered heteroaryl having 1 or 2

Heteroatoms, in particular nitrogen, oxygen or sulfur is and

^! R ² and R ³ are each independently hydrogen

fabric, for each straight-chain or ver

branched alkyl having 1 to θ carbon atoms, hydroxyalkyl having 2 to β carbon atoms or alkoxyalkyl having 3 to θ carbon atoms

for straight-chain or branched alkenyl having 3 to β carbon atoms, for ge

optionally monosubstituted to polysubstituted by identical or different alkyls with i Hs 6 carbon atoms and / or halogen

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Cycloalkyl having 3 to 7 Kohlanstoffatomen or for each optionally in the aryl moiety simple

to multiply, identically or differently substituted aralkyl or aryl having 6 to 10 carbon atoms in the aryl moiety and optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety "being as

Substituents in each case come into question: halogen, cyano, nitro, and in each case straight-chain or branched alkyl, alkoxy, alkylthio, haloalky I, haloalkoxy, haloalkylthio or

Alkoximinoalkyl each having 1 to 4 carbon atoms

atoms in the individual alkyl moieties and optionally 1 to 9 same öler different halogen atoms or

R ² and B ^3, together with the nitrogen atom to which they are attached, represent an optionally mono- to polysubstituted, identically or differently substituted, saturated 5- to 7-membered heterocycle which may contain further heteroatoms, in particular nitrogen,

May contain oxygen and / or sulfur, wherein suitable substituents are: in each case straight-chain or branched alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms, and also their acid addition salts,

excluding the compounds 2-methyl-3-phenyl-5- (piperidin-1-yl-met-ethyl) isoxazolidine and 2-methyl-3-phenyl-5- (morpholin-4-ylmethyl) -isoxazolidine »

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»64 842

Particular preference is given to compounds of the formula (I) in which

R ^{1 is} in each case optionally one to three times,

identically or differently substituted cyclopentyl or cyclohexyl stands "being suitable as substituents JJ straight or branched alkyl having 1 to S carbon atoms; in addition, if appropriate in the phenyl moiety, it is triply, identically or differently substituted phenylalkyl having 1 to 6 carbon atoms in the branched or branched alkyl moiety, suitable phenyl substituents being: fluoro, chloro, bromo, methyl, ethyl, η- or i -Propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoromethoxy or methoximinomethylj furthermore represents optionally mono- to trisubstituted by identical or different substituents phenyl, wherein suitable substituents are: fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms, methoxy, bthoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or methoximinomethyl;

and in each case optionally monosubstituted to trisubstituted by identical or different substituents.

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Naphthyl or 0-naphthyl, with suitable substituents being: fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxyj and also in each case optionally mono- to trisubstituted by identical or different substituents by chlorine, bromine, methyl and / or tert-butyl. Butyl substituted 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl or 3-thienyl and

R ² and R ³ are each independently hydrogen, methyl, ethyl, η- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, allyl , η- or i-butenyl, n- or i-

Pentenyl, hydroxypropyl, methoxyethyl, ethoxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, for cyelopropylmethyl, dichlorocyclopropylmethyl, for dichlorodimethylcyclopropylmethyl, for dimethylcyclopropylmethyl or cy

clohexyl or optionally mono- to trisubstituted by identical or different chlorine or methyl-substituted phenyl or

R ² and R ^3, together with the nitrogen atom to which they are bonded, represent an optionally mono- or trisubstituted, heterogeneously or differently substituted heterocycle of the formula

-Ό * -O ' -O ^οά " - ^n:

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stand »with al · substituents in each case come into question? Methyl, ethyl, hydroxymethyl; such as

their acid addition salts, excluding the compounds 2-methyl-3-phenyl-5- (piperidin-1-ylmethyl) isoxazolidine and 2-methyl-3-phenyl-5- (morpholin-4-ylmethyl) -isoxazolidine · 10

Preferred compounds according to the invention are also addition products of acids and those of aminomethylicoxazolidines of the formula (I) in which the substituents R ¹ , R ² and R ^{3 have} the meanings which have already been mentioned as preferred for these substituents.

Acids which may be added preferably include hydrogen halides, e.g. Hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, mono-, bi- and trifunctional carboxylic acids and hydroxycarboxylic acids, such as e.g. Acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, furthermore sulfonic acids, such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid, and saccharin *

₍ In particular, except for the compounds mentioned in the preparation examples, the following substituted N-methylisoxazolidines of general formula (I) may be mentioned

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CH

(X)

r2 ⁽ r3

(CHg) ₃ C- ^ y-

15 (CH ₃ );

(CH ₃ )

(CH ₃₎ 3 (CH ₃₎ a (CHg) ₃

CF / CH ₃ -NH-CH ₂ -CH

-NH-CH ₉ -CH

/ C ₂ H ₅

-NH-C (CHg) ₃

OH NH-CH ₂ -CH-CH ₃

-NH- (CH ₂ ) ₃ -O- (CH ₂ ) ₂ -CH ₃

Γ ³

-NH-CH ₂ -CH ₂ -Ch ₂ -O-CH ₂ -CH ₂

CH.

-NO

CH.

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10

20 25 30

P ¹ H ₃ JUX Cl " ^{N <} a F ³ CIF " , CH ₃ -0 CH ₃ Cl O -O -NH-CH ₂ -CH ₂ -CH ₂ -OC ₂ H ₅ Cl Cl -NHH ^) - Cl CH ₃ CH ₃ -NH-CH ₂ -CH ₂ -CH ₂ -CH ₃ CH ₃ -N 0 CH ₃ -NH-CH ₂ -CH ₂ -CH ₃

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264 642

CH.

-ν

-NH-CH ₂ -CH ₂ -OCH ₃

, CH ₃

 0

CH ₃

If, for example, N-methyl-4-t-butylbenzylnitrone and N-allylpiperidine are used as starting materials, the course of the reaction of process (a) according to the invention can be represented by the following formula:

(CH ₃ ) ₃

HN? 4 H ₂ C-CH-CH ₂ -N) CH ₃ ^N '

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CH ₃

For example, using 5-bromomethyl-2-methyl ~ 3 ~ (2-

mothylphenyl) -isoxazolidine and 3-methylpiperidine as starting materials, so IiH represent the reaction sequence of the process according to the invention · (b) by the following formulas?

GH, CH ₂ -Br CH ₃

^ N-0 CH ₃ 20 ³

♦ ^H -ö

-HBr 25 (base)

Roe

CH

For example, when 2-methyl-3-cyclohexyl-5- (N-cyclohexylaminomethyl) -oxazolidine and allyl bromide are used as starting materials, the reaction sequence of process (c) according to the present invention is represented by the following formula.

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10

CH ₉ -NH-K H

-HBr

(Bate)

4 CH ₂ ⁸ CH-CH ₂ -Br

CH ₉ -

/ CH ₂ -CH-CH ₂

15 20 25 30

Dia for carrying out the process according to the invention (a) all starting substances required nitrones are generally defined by the formula (II). In this formula (II), R * preferably represents those radicals which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention for this substituent.

The nitrones of formula (II) are largely known (see, for example, J. org. Chem., 3Jg, 261 [1969]; Cham. Ber. , 101, 2548 (1968); Synthesis 1974, 478; Tetrahedron Lett. »4331 [1985]) or can be obtained in analogy to known processes (see, for example, Houben-Weyl" Methoden der organischen Chemie "Volume X, 4, 4th Edition, Thieme Verlag Stuttgart 1968, p 328 or HeIv. Chim. Acta 5J5_, 2187 [1972.I] _1, for example, if aldehydes of the formula (VII),

R ^ CHO (VII)

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264 642

in which

R * di · given above meaning »with N-methylhydroxylamine of the formula (VIII), CH ₃ -NH-OH (VIII)

or the hydrochloride thereof in the presence of a base such as potassium hydroxide at temperatures between + 2U ⁰ C and 120 ⁰ C.

The N-methylhydroxylamine of the formula (VIII) as well as the aldehydes of the formula (VII) are generally known compounds of organic chemistry or obtainable in analogy to generally known processes (see also Liebigs Ann, Chem. 1979, 1565).

The allylamines which are furthermore required as starting materials for carrying out the process (a) according to the invention are generally defined by the formula (III). In this formula (III), R ² and R ^{3 are} preferably those radicals which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention for these substituents.

The allylamines of formula (III) are also well-known compounds of organic chemistry.

The isoxazolidines required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (IV). In this

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Formula (IV), R ¹ preferably represents those radicals δ which have already been mentioned in connection with the description of the inventive compound of formula (I) for these substituents.

X * is preferably halogen, "in particular chlorine or bromine" or optionally substituted AlKylsulfonyloxy or arylsulfonyloxy, such as methanesulfonyloxy or p-toluenesulfonyloxy.

The isoxazolidines of the formula (IV) are not yet used. They are obtained in analogy to the process (a) according to the invention, when nitrones of the formula (II) "

^CH 3

in which

R ^{1 has} the meaning given above «26

with allyl halides or allyl alcohol of the formula (IX)

CH ₂ CH-CH ₂ -X ³ <IX)

,.

in which

X ^{3 stands} for hydroxy or halogen «in particular for hydroxy, chlorine or bromine«

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if appropriate in the presence of a diluent, such as, for example, toluene at temperatures between 60 ^° C. and 140 ^° C., and in the cases where X ^{3 is} hydroxyl, the hydroxymethylfsoxazolidines of the formula (X) obtainable in this way

CH ₂ -OH

in which

R ^{1 has} the meaning given above,

2Q in a 2 x stage with sulfonyl halides of the formula (XI),

X ⁴ -SO ₂ -R ⁴ (XI) in which

X ⁴ represents halogen, in particular chlorine or bromine, and

₃ q R ^{4 is} optionally substituted alkyl or aryl, such as, for example, methyl or p-tolyl,

optionally in the presence of a diluent such as, for example, oichloromethane and optionally in _g . Presence of a Basic Reaction Aid

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For example, triethylamine at temperatures between 10 ⁰ C and 60 ⁰ C converts.

The allyl halides or the allyl alcohol of the formula (IX) and the sulfonyl halopgenides of the formula (XI) are generally known compounds of organic chemistry. 10

The methods for carrying out the method according to the invention

(b) Amines further required as starting materials are generally defined by the formula (V). In this formula (V), R ² and R ^{3 are} preferably those radicals which have been mentioned in connection with the description of the substances of the formula (I) according to the invention for these substituents.

The amines of formula (V) are also well known compounds of organic chemistry.

The for carrying out the method according to the invention

(c) Substituted N-methylisoxazolidines required as starting materials are generally defined by the formula (Ia). In this formula (Ia), R ¹ and R ² preferably represent those radicals which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention for these substituents.

The substituted N-methylisoxazolidines of the formula (Ia) are compounds according to the invention and can be obtained by means of the processes (a) according to the invention: md (b).

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The alkylating agents required for the preparation of the invention are generally defined by the formula (VI). In this formula (VI), R ³ "* is preferably each straight-chain or branched alkyl having 1 to β Carbon atoms, hydroxyalkyl having 2 to 8 carbon atoms or alkoxyalkyl having 3 to 8 carbon atoms »for straight-chain or branched alkenyl having 3 to 8 carbon atoms, optionally substituted once or more than once, identically or differently by alkyl having 1 to 6 carbon atoms and / or halogen substituted cycloalkyl with 3 to 7 carbon atoms or for each optionally in the aryl moiety mono- to polysubstituted, identically or differently substituted aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, in each case being mentioned as aryl substituents:

Halogen, cyano, nitro, and in each case straight-chain or branched alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, halogenoalkylthio or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties and optionally 1 to 9 identical or different halogen atoms.

R ³ ' ¹ is in particular methyl, ethyl, η- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, allyl, η- or i-butenyl, n- or i-

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Methoxypropyl, ethoxypropyl, propoxypropyl or cyclohexyl, cyclopropylmethyl, dichlorocyclopropylmethyl, dimethylcyclopropylmethyl or dichlorodimethylcyclopropylmethyl "X ² is preferably halogen, in particular chlorine or bromine or optionally substituted alkylsulfonyloxy or arylsulfunyloxy, such as lü example methaneulfonyloxy or p-ToAuolsulfonyloxy. \

The alkylating agents of the formula (VI) are generally known compounds of organic chemistry 15

Suitable diluents for carrying out the process according to the invention (a) are inert organic solvents,

These include in particular aliphatic or aromatic, optionally halogenated Kohlenwanseretoffe such as gasoline, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ether, win diethyl ether, dioxane, tetrahydrofuran or Ethyleng) ykoldimethyl- or diethyl ether, ketones, such as acetone or butanone, nitriles, such as acetonitrile or propionitrile, amides, such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide, esters, such as ethyl acetate or sulphoxides, such as dimethyl sulphoxide.

The reaction temporations can be carried out in the implementation of the process according to the invention (a) in a larger process

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842

Range are varied "In general, one works at δ temperatures between 20 ⁰ C and 150 ⁰ C, preferably at temperatures between 40 ⁰ C and 140 ⁰ C *

To carry out the process (a) according to the invention, in each case from 0.8 to 1.3 mol of preferably 1 to 10 equivalents of allylamine of the formula (III) are employed per mole of nitrone of the formula (II).

It is also possible «the nitrone required as precursors« of the formula (II) in an upstream reaction »us the aldehydes of the formula (VII) with N-methylhydroxylamine of formula (VIII) directly in the reaction vessel and in a" one-pot reaction "without isolation according to the process (a) further to implement «

20

The ReaktionsdurchfUhrung, workup and isolation of the reaction products of the formula (I) by means of conventional methods in analogy to known methods «

Suitable diluents for carrying out processes (b) and "c) according to the invention are inert organic solvents or aqueous systems."

,. These include, in particular, aliphatic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzene, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimer.

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ethyl or diethyl ether, ketones such as acetone or buta-β-non, nitriles such as acetonitrile or propionitrile, amides such as dimethylformamide, dimethylacetamide, N-methylfermanilide, N-methylpyrrolidone or hexamethylphosphoric triamide, esters such as ethyl acetate or sulfoxides such as dimethyl sulfoxide

 10

It is also possible to carry out the processes (b) and (c) according to the invention without addition of a solvent.

The processes (b) and (c) according to the invention can also be carried out in a two-phase system, such as, for example, water / toluene or water / dichloromethane, if appropriate in the presence of a phase transfer catalyst. Examples of such catalysts are: tetrabutylammonium iodide, tetrabutylammonium bromide, tributylmethylphosphonium bromide, trimethyl-C 1 -C -alkylammonium chloride, dibenzyldimethylammonium methylsulfate, dimethyl C ₁₂ ^{/ C} 14 'alkylbenzylammonium chloride, tetrabutylammonium hydroxide, 15N-crown-5, 18 crown-6, triethylbenzylammonium chloride or trimethylbenzylammonium chloride.

Suitable acid binders for carrying out the processes (b) and (c) according to the invention are all customary inorganic and organic bases. Preference is given to using alkali metal hydroxides, carbonates or bicarbonates, such as, for example, sodium hydroxide, sodium carbonate or sodium bicarbonate, or tertiary amines such as, for example, triethylamine, Ν, Ν-dimethylaniline, pyridine, 4- (N ₁ N-

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Dimethylamino) pyridine, Diazab J cyclooctane (DABCO) * diazabicyclononene (OBN) or diazabicycloundecene (DBU) *

It is also possible to use the acid-binding agents used simultaneously in the amines of the formulas (V) and / or (Xa) in a corresponding excess.

· Cm, the reaction temperatures can in the practice of the inventive process (b) and (c) varies in a relatively wide range generally carried out at temperatures between x 20 ⁰ C and + ISO ⁰ C, preferably at temperatures between ⁰ ° C and ♦ 120 ⁰ C.

For carrying out the process (b) according to the invention, in general 1.0 to 3.0 mol, preferably 1.0 to 1.5 mol, of the amine of the formula (V) and, if appropriate, 1 are added per mole of isoxazolidine of the formula (IV) 0 to 3.0 mol, preferably 1.0 to 1.5 mol of Slurebindemittftl, and optionally 0.1 to 1.0 mol of phase-2P transfer catalyst ein ·

For carrying out the process (c) according to the invention, in general 1.0 to 5.0 mol, preferably 1.0 to 2.0 mol, of alkylating agent and 1.0 to 1.0 mol per mole of substituted N-methylisoxazolidine of the formula (Ia) 5.0 mol, preferably 1.0 to 2.0 mol of Slurebindemittel, and optionally 0.1 to 1.0 mol of Phasehtransferkatalysator ein «

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Di · Reaction Procedure, Work-Up and Analysis B of Reaction Products Formal (I) is Carried out in both Fl uences by Conventional Methods ·

For the preparation of 8iureadditionasalien the compounds of formula (I) are preferably the following

tO acidic hydrogen halide acids «such. Hydrochloric acid and hydrobromic acid, especially hydrochloric acid, further phosphoric acid, nitric acid, sulfuric acid, mono-, bi- and trifunctional carboxylic acids and hydroxycarboxylic acids, e.g. Acetic, maleic, succinic, fumaric, tartaric, citric, salicylic, sorbic, lactic and sulfonic acids, e.g. p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid and saccharin.

The acid addition salts of the compounds of the formula (I) can be prepared in a simple manner by customary salting methods, such as e.g. by dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrochloric acid, and in a known manner, e.g. by filtration, isolated and optionally purified by washing with an inert organic solvent.

The active compounds according to the invention have a strong action against pests and can be used practically for controlling unwanted harmful organisms

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The active ingredient is for use i.a. al. β pesticides especially suitable as fungicides «

Fungicide agents in the patch protection are used to combat Plasmodiophoromycete, "Oomycetes, Chytridiomycetes, Zygomycetes" Ascomycetes, Basidiomycetes, Deuteromycetes.

By way of example, but not by way of limitation, some pathogens of fungal diseases are named "the generic concepts mentioned under the practice":

Pythium species such as Pythium ultimumj Phytophthora species * such as Phytophthora

infestansj Pseudoperonospora species »such as

Peeudoperonospora humuli or Pseudoperonospora

cubensis;

Plasmopara species such as Plasmopara

viticolaj peronospora species such as, for example, Peronospora pisi or P. brassicae;

Erysiphe species such as Erysiphe graminisj Sphaerotheca species »such as Sphaerotheca

fuliginea; Podosphaera species »such as Podosphaera leucotricha;

Venturia species »such as Venturis inaequalis; Pyrenophora species, such as Pyrenophora teres

or P. graminwa 35

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2 * 4

(Conidia form, Drechslera, Synt Helminthosporium); Cochliobolus species »such as Cochliobolus sativus (conidia form: Drechsler · Syn! Helminthosporium);

Uromycee species, such as Uromycos

sppendiculatue; Puccinia species, such as Puccinia recondite;

Tilletia species, such as Tilleia caries; Ustilago species, such as Usiilago nuda or Ustilago avenae;

Pellicularia species »such as Pellicularia IS sasakii;

Pyricularia species, such as Pyricularia

oryzae;

Fuearium species such as Fusarium culinorum;

Botrytis species, such as Botrytis cinerea; ^ Septoria species, such as Sepioria nodorum;

Leptosphaeria species , such as Leptosphaeria

nodorum;

Cercospora species, such as Cercospora

canescens; Alternaria species, such as Alternaria brassicae;

Pseudocercosporella species »such as Pseudocercosporella herpotrichoides «

The good plant tolerance of the active ingredients in the concentrations necessary for the control of plant diseases allows a treatment of aboveground plant parts "of plant and seed" and the soil.

Le A 24 945 - Au3la0d

- 30 -

The active compounds according to the invention show a particularly broad fungicidal activity and can be used particularly successfully for combating cereal diseases such as, for example, the causative agent of the wheat barley wheatblood (Leptosphaeria nodorum) or the causative agent of the true barley powdery mildew (Erysiphe graminis) against the causative agent of Blattfleckenkr.nkheit on rice (Pyricularia oryzae) or to combat diseases in fruit growing ι such as against the causative agent of apple scab (Venturi · ihaequalis) use «It should be emphasized» that the active compounds of the invention not only protective but also curative properties have"

In addition, the active substances are suitable for combating animal pests "preferably arthropods", in particular insects and arachnids, which are found in agriculture "in forestry" in the protection of stored products, materials and the hygiene sector "They are against normally sensitive and resistant species and against all or individual stages of development are effective «The pests mentioned above include:

From the order of isopods e.g. Oniscus asellus »Arma. , dillidium vulgare »Porcellio scaber» From the order of Diplopoda z «B« Blaniulus guttulatue.

From the order of the Chilopoda z «B« Oeophilus carpopha-

gusj Scutigera spec.

From the order of Symphyla e.g. Scutigerella immacu-

lata

 35

L »a 24 945 . foreign countries

- 31 -

From the order of Thysanura e.g. Lepisma saccharina. From the order of Collembola e.g. Onychiurus armatue.

Except the order of Orthoptara, for example "Blatta oriental is, Periplaneta americana, Leucophaea maderae, Blattella

germanica, Acheta domesticus · Oryllotalpa spp, Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria,

From the order of the Dermaptera e.g. Forficula auricula

ria.

From the order of Isoptera e.g. Reticulitis spp. «

From the order of the Anoplura e.g. Phylloxera vastatrix, Pemphigus spp «» Pediculus humanus corporis, Haematopinus spp.i Linognathus spp.

From the order of Mallophaga e.g. Trichodectes spp. " Dentalinea spp «

From the order of Thysanoptera e.g. Hercinothrips femoral ie, Thrips tabaci.

From the order of the Heteroptera for example "Eurygastsr spp", Dysdercus intermedius, Piesnta quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp "From the order of Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne braosicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum ovenae, Myzuβ spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psyl'a spp «

A 24? 4E decency

- 32 -

2 * 4 842

From the order of Lepidoptera e.g. Pectinophora goeey piella, Bupalue piniarius, Cheimatobia brumata, Lithocolletia blancardella, Hyponomeuta padella, Plutella maculipennia, Malacoeoma neuetria, Euproctis chryeorrhoea, Lymantria epp, Bucculatrix thurberiella, Phyllocnistis citrella, Agrotie epp. Euxoa epp., Feltia epp., Eariae ineulana, Heliothie epp, Spodoptera exigua, Mameetra braesicae, Panolie flame, Prodenia litura, Spodoptera epp., Trichoplueia ni, Carpocapea pomunella, Pierie epp., Chilo epp., Pyraueta nubilalie, Epheetia kuehniella, Oelleria mellonella, Tineola bieelliella, Tinea pellionella, Hofmannophila peeudoeprebella, Cacoecia podana, Capua reticulana, Chorietoneura furoiferanb, Clyeia ambiguella, Homona magnanima, Tortrix viridana

 Order of Coleoptera order e.g. Anobiuro punctatutn,

Rhizopertha dominica, Acanthoecelidee obtectue,

Hylotrupee bajulue, Agelaetica alni, Leptinotarea decemlineata, Phaedon cochleariae, Diabrotica epp., Peylliodee chryeocephala, Epilachna variveeiie, Atomar! A epp., Oryzaephilue eurinameneie, Anthonoroue epp., Sitophilus epp., Otiorrhynchue eulcatus, Coemopolitee eordidue, Ceuthorrhynchue aeeimilie, Hypera poetica , Dermetee epp. "Trogoderma epp", Anthrenue βρρ.ι Attagenue epp., Lyctue epp., Meligethee aeneue, Ptinue epp., Niptue hololeucue, Oibbium peylloidee,

30. Tribolium epp., Tenebrio molitor, Agriotee epp., Cono deru epp., Melolontha melolontha, Amphimallon eoletitialia, Coetelytra zealandica.

Aue of the order Hymenoptera, for example, Diprion epp., Hoplocampa epp, Laeiue epp., Monomorium pharaonie, Veepa epp.

Le A 24 945 - abroad

- 33 -

From the order of Diptera e.g. Aedes spp <«Anopheles spp.» Culex spp., Drosophila melanogaster, Muse · spp. «Fannia spp» «Calliphor * erythrocephala, Lucilia spp., Chryeomyia spp ·» Cuterebra spp «« Gastrophilus spp · «Hyppobosca spp« «Stomoxys spp «Oestrus spp ·« Hypoderma spp · «Tabanus spp« «Tannia spp» «Bibio hortulanus» Oecinella frit «Phorbia spp ·« Pegomyia hyoscyami «Ceratitis capitata» Dacus oleae «Tipula paludoea«

From the order of siphonaptera e.g. Xenopsylla cheopis «Ceratophyllus spp ··

IS From the Order of the Arachnids ζ «Β« Scorpio maurus «Latrodectus roactans»

From the order of Acarina ζ.Β «Acarus siro« Argas spp «« Ornithodoros spp · «Dermanyssus gallinae« Eriophyee ribis «Phyllocoptruta oleivora« Boophilus spp «« Rhipicephalus spp «« Amblyonuna spp · «Hyalomma spp ·» Ixodes spp «« Psoroptes spp «« Chorioptes spp. «Sarcoptes spp« «Tareonemu ß spp« «Bryobia praetiosa» Panonychus spp · «Tetranychus spp« «

The active compounds according to the invention not only act against plant "hygiene and storage pests" but also in the veterinary medical sector in livestock "such. Cattle »Sheep« Pig «Horse« Goat «

Buffalo «Camels; for pets «like« dogs «

cats; in so-called laboratory animals such as rats, mice, hamsters, rabbits and bees; against animal parasites (ectoparasites), such as ticks, leather tokens, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hairy creatures, feathers, fleas

L? A? 4 for foreign countries

- 34 -

264 8 * 2

resistant · Species and voice · as well as to all paratitized and non-parasitic stages of development of ectopaxrasites effective «In particular, the active substances according to the invention are suitable in this field for combating mange mites (Psoroptes ovis)«

Depending on their physical and / or chemical properties, the active ingredients can be converted into conventional formulations »such as solutions» emulsions »suspensions» powders «foams» pastes »granules» aerosols »active ingredient-impregnated natural and synthetic substances» ultra-fine encapsulation in polymeric substances and in aggregates for seeds »also in formulations with fuel additives» such as smoking cartridges »cans» spirals, etc., as well as ULV-KaIt and warm mist formulations «

These formulations are prepared in a known manner »z« B. by mixing the active compounds with diluents, ie liquid solvents, with pressurized liquefied gases and / or solid triggers, if appropriate with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foaming agents. In the case of using water as diluent eg It is also possible to use organic solvents as auxiliary solvents. "Liquid solvents are essentially suitable. Aromatics »such as xylene» toluene »or alkynaphthalenes» chlorinated aromatics or chlorinated aliphatic hydrocarbons »such as chlorobenzenes» chloroethylenes or methylene chloride »aliphatic hydrocarbons such as cyclohexane or paraffins» z «B, petroleum

Le a 24 945. Abroad

- 35 - Z64 842

Fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, or water; By liquefied gaseous diluents or carriers are meant liquids which are gaseous at normal temperature and under normal pressure "z" B "aerosol propellants" such as halogenated hydrocarbons as well as butane »propane, nitrogen and carbon dioxide; as solid carriers come into question! z "B. ground natural minerals, such as kaolins, clays, talc, chalk »Quartz» Attapulgite »Montmorillonite or diatomaceous earth and ground synthetic minerals, such as fumed silica» Aluminum oxide and silicates; solid carriers for granules are: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice »sepiolite» dolomite and synthetic granules of inorganic and organic flours, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam-formers are: z "B" non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters "polyoxyethylene fatty alcohol ethers" e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; as dispersants come into question:

3ϋ 2 «B« lignin sulphite waste liquors and methylcellulose.

Ee can be used in the formulations adhesives such as carboxymethylcellulose »natural and synthetic powdery» granular or latex-like polymers »such as 35

Le A 24 945 - abroad

Gummiarabicumι Polyvinylalcohol »Polyvinylacetate, and of course · Phospholipids, such as cephalin · and lecithin · and synthetic phospholipids« Other additives may be mineral and vegetable oils ».

Et can dyes such as inorganic pigments ι z «B« iron oxide, titanium oxide ι Ferrocyanblau and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used

The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90% by weight.

When used as fungicides, the active compounds according to the invention can be present in the formulations in a mixture with other known active compounds such as fungicides, bactericides, insecticides, acaricides, herbicides, bird repellents, growth substances, plant nutrients and soil conditioners.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. The application is carried out in a customary manner, for example by casting, spraying, Spraying, scattering, dusting, foaming, brushing etc. "" It is also possible to use the active ingredients after the ultra-low

Le A 24 945 . foreign countries

Volume method or inject the Wirketoff-uberei-B tion or Wirkatoff itself into the ground tu. Ea, the seeds of the plants can be treated ·

In the treatment of plant parts, the active compound concentration in the forms of application can be varied within a wide range. They are generally between 1 and 0.0001 parts by weight, and between 0.5 and 0.001 ×

In seed treatment, effective weight fractions of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.

When treating the soil, effector concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02 X, are required at the site of action.

When used as insecticides and acaricides, the active compounds of the invention may also be present in their commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides. The insecticides include, for example, phosphoric acid esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, microorganism-produced substances and the like.

Le A 24 945 - abroad

- 38 -

The active ingredient according to the invention can also be present in its commercial formulations as well as in the formulations prepared for these formulations in admixture with synergists. Synergists are compounds "by which the action of the active ingredients is increased" without the added synergist itself being actively active got to"

The active ingredient content of the use forms prepared from the commercial formulations can vary widely. The active ingredient concentration of the application forms can range from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.

The application is done in a custom forms adapted to the application forms.

When used against hygienic and storage bugs, the active ingredients are characterized by an excellent residual effect on wood and clay as well as a good alkali resistance on limed substrates «

The active substances which can be used according to the invention are also suitable for the control of insects, mites, ticks, etc. in the field of livestock and livestock breeding, whereby better results, for example higher milk yields, higher weight, better animal fur, longer life span, etc «Can be achieved.

Le A 24 945

- 39 -

642

The application of the active compound usable according to the invention is effected in the known manner by oral application in the form of, for example, tablets, capsules, »drinking» granules, dermal biw. daily use in the form of, for example, dipping, spraying, pour-on and spot-on, and inserting, as well as by parenteral application in the form of, for example, injection, and also by the feed-through method "In addition, it can also be used as a shaped body (collar, ear tag)"

Le a 24 945 - foreign countries

- 40 -

Production Examples 6

Example: It

CH

(Method a)

To a solution of 17.5 g (0.14 mol) of N-Allylpiperidin in 120 ml of toluene is added dropwise at 100 ⁰ C "ine solution of 14.9 g (0.1 mol) of 2-Methylbenialdehyd-N-methyl nitrone in 100 ml of toluene "After completion of the addition the mixture is stirred for a further 16 8tunden at 110 ⁰ C, the cooled Resktionsmischung wash with water, dried over sodium sulfate, concentrated in vacuo and the residue is Kieeelgel chromatoyraphiert (Laufmitteli petroleum ether / Essigester 2JL)

This gives 12.5 g (45 K of theory) of 2-methyl-3-O-methylphenyl) -5- (piperidin-1-ylmethyl) -ieoxazolidine of refractive index ηB ⁰ 1.5222.

i "

Le A 24 945. foreign countries

- 41 -

842

H ere creation of the Ausaana connection

To a solution of 84 g (1.5 mol) of potassium hydroxide in 600 ml of methanol are added with stirring and cooling in portions 12!>, 25 g (1.5 mol) of N-methylhydroxylamine hydrochloride and filtered after 30 minutes, the precipitate from « The filtrate is added to 120 g (1 mol) of 2-methylbenzaldehyde in 500 ml of toluene »sets 400 g of sodium sulfate and stirred for 16 hours at 80 ⁰ C. For workup is filtered, the filtrate concentrated in vacuo, the residue taken up in ethyl acetate, Dried over sodium sulfate and freed from the solvent in vacuo.

This gives 134 g (90 X of theory) of 2-methylbenzaldehyde-N-methylnitrone of refractive index n $ ° 1.6053.

25 Example 2;

Le A 24 945 - abroad

- 42 -

To a solution of S 3 g (0.02 mol) of 2-methyl-3- (2-methylphenyl) -5- (1-piporidinylmethyl) -ieoxazolidine in 30 ml of acetone is added a solution of 3.6 g (0 , 02 mol) of saccharin in 50 ml of acetone, stirred for 10 minutes at room temperature and the solvent removed in vacuo. Preserves 8.9 g (100 % of theory) of 2-methyl-3- (2-methylphenyne-S-ipiperidin-1-ylmethyD-i-oxazolidine-saccharose salt as a neat oil.

¹ H-NMR (CDCl3 / TMS): & 4.9 - 5.0 (πι, IH); 4,7 - 4,8

(m, lH) ppm «

Xn corresponding manner and according to the general information on the preparation gives the following substituted N-methylisoxazolidines of the general formula (I)! 20

XTTO ^ S _x R ²

nt] ^ U _ .. M c

^{3 2} FS

Le a 24 945 - foreign countries

- 43 -

Ex. No phyical data

4 (CH ₃ ) ₃

5 (CH ₃ J ₃

CHi

25

Cf

-N

CH ₂

CH ₃ CH ₃ Ο CH ₃

-NO

CH

ng ⁰ 1.5272

ng ⁰ 1.5268

ng ⁰ 1.5167

¹ H NMR *>: 4.7-5.0 4.1-4.3 2.9-3.9

"W ng ⁰ 1.5147 CH ₃ -Q CH ₃ ¹ H-NMR **: 4.7-5.0} 3.9-4.2; 3.6-3.8 χ (Γ jT _χ ΝΗ CH ₃ -Q ng ⁰ 1.5148

CH,

Le A 24 945 - abroad

- 44 -

10 15 20 25 30 35

Bap. No ♦

10

CH ₅

11

12

Ö

13 (CHg) ₂ C

: i4 (CHg) ₂ C

Cl

R ³

15 cl

16 cl

L «a 24 945 - foreign countries χ

, CH

CH.

physically · data

¹ H NMR ** I 4.65-5.0; 3.0-4.0

-NO n ° 1.5192 ν '' ' I ' ¹ V Vv Λ \ N CH ₃ * ,; '*>~' \ - 1 CH ₃ ¹ H-NMR * ^ 4.65-5.05; 4.1-4.35; 3.0 -4.0 ?! * \ ccr * ^H , CH ₃ Ό CH ₃ n ° 1.4945 CH ₃ CH ₃ B ° 1.4960  <; CH ₃ nb ° 1.5660 Mp 38 ⁰ C

- 45 -

Eg, R ^J

No, physical data

Cl

17

n ° 1.5168

Cl

18 cl

-O

19 (CHg) ₂ C

20

Cl

21

22 (CH ₃ ) ₂ C

Cl

egg

CH ₃ -N 0

CH ₃ CH ₃

CH. n8 ° 1,5523

'S'

23 (CH ₃ ) ₂ C

24 (CHg) ₂ C

-O

CH

NOX

CHO

Le a 24 945 . foreign countries

- 46 -

Ex. R ¹ No. r2 r3

physical data

Cl

25 cl

-0

CH,

Mp 79 ⁰ C

26

27

CH-

CH

-O

ng ⁰ 1.5142

ng ⁰ 1.5291

28 cl

29 cl

Cl

Cl

, CH ₃

• Ν. Ο

CHr

CH ₃ 7.2-7.9 (in)

¹ H-NMR * * ί

0.9-l, 3 <m);

7.2-7.9 (m)

Le A 24 945 - abroad

Example no.

- 47 -

_χ 2 ) 3

physical data

30

31

¹ H-NMR * l, 2-l, 4 7,6-7,9 (m)

-O

¹ H NMR * ^ 7.6-7.9 <m)

The ¹ H NMR spectra were recorded in CDCl ₃ with tetramethylsilane (TMS) as the internal standard. "The chemical shift is given as {value in ppm."

Le A 24 945 - abroad

- 48 -

Application Example 5 In the following application examples, the following compound was used as the reference substance:

(CH ₃ ) ₃ C ^CH

5-benzyl-5'ethoxycarbonyl "2-t-butyl-isoxazolidine

(confesses from DE-OS 34 18 395).

Le A 24 945 - abroad

- 49 -

UA 842

Example A 5

Erysiphe test (barley) / protective

Solvent: 100 parts by weight of dimethylformamide ECmulgators 0.25 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective efficacy, young plants are dewy with the preparation of the active compound. »After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f.sp.hordei.

The plants are placed in a rewachshaus at a temperature of about "20 ⁰ C and a relative humidity of about" 80 X to the development of mildew pustules to Legunstigen "

7 days after the inoculation the evaluation takes place.

Clear superiority in efficacy over the prior art is demonstrated in this assay, e.g. the compounds according to preparation examples 3, 4 and 5

Le a 24 945 - foreign countries

- 50 -

Example B 5

Test with Peoroptee ovie

Solvent 35 parts by weight of ethylene glycol monomethyl ether

35 parts by weight of nonylphenol polyglycol ether

For the preparation of a suitable preparation of active ingredient

mixing three parts by weight of active compound with seven parts by weight of the abovementioned solvent mixture and diluting the concentrate thus obtained with water to the desired concentration

20 Approximately 10 - 25 Psoroptes ovis are placed in 1 ml of the active compound preparation to be tested * which have been pipetted into tablets * in a thermoformed packaging «After 24 hours the degree of mortality is determined«

25 In this test, the compounds of Preparation Examples 3 and 4 show a superior effect over the prior art.

30

36

Le A 24 945 . foreign countries

Claims (8)

In which R is each optionally substituted AUsyl, cycloalkyl, aryl or heteroaryl, R and R ^ are each independently hydrogen, each optionally substituted alkyl, alkenyl, CyIoalkyl or aryl or together with the nitrogen atom to which they are attached , represents an optionally substituted, saturated hetero-olefin, which may optionally contain further heteroatoms, and their acid addition salts and their geometrical and optical isomers and mixtures of isomers, excluding the compounds 2-methyl-3-phenyl-5- (piperidin-1-yl-methyl ) -isoxaaolldine and 2-methyl-3-phenyl-5- (morpholin-4-ylmethyl) -lsoxazollin, in addition to extenders and / or surface-active agents « 1 to 4 carbon atoms in the individual alkyl moieties and optionally 1 to 9 identical or different halogen atoms; also for optionally mono- to polysubstituted by identical or different alkyl with 1 to 6 carbon atoms substituted cycloalkyl having 3 to 7 carbon atoms or for optionally mono- to polysubstituted by identical or different substituted phenyl »being suitable as sub-substituents? Halogen »Cyano» Nitro »in each case straight-chain or branched alkyl» alkoxy »alkylthio» Le A 24 945 abroad - 53 - Haloalkyl ι halogenoalkoxy or haloalkylthio each having 1 to 6 Carbon atoms and optionally 1 to 9 identical or different halogen atoms, amino «each straight-chain or branched alkylamino, dialkylamino or alkoximinoalkyl each having 1 to 4 carbon atoms in the individual alkyl parts; furthermore, in each case optionally monosubstituted to polysubstituted or differently substituted naphthyl or β-naphthyl, suitable substituents being in each case come! Halogen, in each case straight-chain or branched alkyl or alkoxy having in each case 1 to 4 carbon atoms and finally in an optionally mono- to polysubstituted by identical or different alkyl having 1 to 2. Composition according to claim 1, characterized in that in the formula (I) - 52 - R ^{1 is} straight-chain or branched alkyl with S I to 18 carbon atoms »for optionally mono- to polysubstituted by identical or different alkyl having 1 to 6 carbon atoms substituted cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 8 Carbon atoms in straight-chain or ver branched alkyl or for optionally in the aryl moiety mono- to polysubstituted or differently substituted aralkyl having 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and 6 to 10 carbon atoms atoms in the aryl part is "where as aryl substituents in question halogen" gsradkettiges or branched alkyl »alkoxy» alkylthio, alkoximinoalkyl, haloalkyl »haloalkoxy or haloalkylthio with each 3. Composition according to Anspruoh 1, characterized in that in the formula (I) R ^{1 is} in each case optionally monosubstituted to trisubstituted) identically or differently substituted cyolopentyl or cyclohexyl, suitable substituents being: straight-chain or branched alkyl having 1 to 5 carbon atoms; also represents optionally in the phenyl, mono- to trisubstituted by identical or different phenylalkyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl part, where as phenyl substituents come into question: fluorine, chlorine, bromine, methyl, ethyl, η- or i- Propyl, n-, i-, s- or t-butyl, trifluoromethyl, ÜPrifluormethoxy or methoximinomethyl; furthermore represents optionally monosubstituted to trisubstituted, disubstituted or differently substituted phenyl, where suitable substituents η are: fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms, methoxy, ethoxy, n- or i-propoxy, n -, i-, s- or t-butoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or methoximinomethyl; furthermore represents in each case optionally monosubstituted to trisubstituted, completely or differently substituted ot-naphthyl or .beta.-naphthyl, - 56 - all sub-substituents being suitable: fluorine, chlorine, bromine, mexhyl, ethyl, methoxy or ethoxy; and also in each case optionally mono- to trisubstituted by identical or different substituents from chlorine, bromine, methyl and / or t-butyl-substituted 2-pyridyl, 3-pyridyl, 4-pyridyl t 2-thienyl or 3-thienyl, and R ² and R ³ are each independently hydrogen, methyl, ethyl, η- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, Allyl, η- or i-butenyl, n- or i- Pentenyl, hydroxypropyl, methoxyethyl, ethoxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, cyclopropylmethyl, dichlorocyclopropylmethyl, dichlorodimethylcyclopentophenylmethyl, dimethyl eyepropropylmethyl or the like Cyclohexyl or phenyl optionally substituted once to three times identically or differently by chlorine or methyl or R ² and R ³ together with the nitrogen atom to which they are attached, for an optionally mono- to trisubstituted by identical or different substituted heterocycle of the formula Γ
-N ^or ' ^r ' which may be used as substituents. methyl, ethyl, hydroxymethyl, Le A 24 945 - AU8land - 57 - 264 042 and their acid addition salts and their geometrical and optical isomers and isonating mixtures, with the exception of the compounds 2-methyl-3-phenyl-5- (piperidin-1-yl-methyl) -isoxa-0-lidine and 2-methyl-3-phenyl-5-one (morpholin-4-yl - methyl) -isoxazolidin · Use of substituted N-methylisoxazalidins of the formula (I) according to Claim 1, characterized in that they are used for combating pests. 5 ancestors for combating Sohädlingen, characterized in that substituted N-methyl-isoxazolidine of the formula (I). According to claim 1 is allowed to act on pests or their living space Process for the preparation of pesticides, characterized in that substituted N-methylisoxazolidines of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active agents. 6 carbon atoms and / or halogen-substituted 5-membered or 6-membered heteroaryl group having 1 or 2 heteroatoms and R ² and R ³ are each independently Is hydrogen, in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, hydroxyalkyl having 2 to 8 carbon atoms or alkoxyalkyl having 3 to 8 carbon atoms for straight-chain or branched alkenyl having 3 to 8 carbon atoms, optionally mono- to polysubstituted, identically or differently, by lower alkyl having 1 to 6 carbon atoms and / or halogen sub- Le A 24 945 - abroad - 54 - substituted cycloalkyl having 3 to 7 carbon atoms or each optionally in the aryl part monosubstituted to polysubstituted or differently substituted aralkyl or aryl having 6 to 10 carbon atoms in the aryl moiety and optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety ι wherein as substituents in question are each: halogen »cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl moieties and optionally 1 to 9 identical or different halogen atoms or R ² and R ^3, together with the nitrogen atom to which they are bonded, represent an optionally mono- to polysubstituted, identically or differently substituted, saturated 5- to 7-membered heterocycle, which optionally contain further heteroatoms may, where suitable substituents are: in each case straight-chain or branched alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms; and their secondary addition salts and their geometrical and optical isomers and isomer mixtures, with the exception of the compounds 2-methyl-3-phenyl-5- (piperidin-1-ylmethyl) isoxazolidine and 2-methyl-3-phenyl-5- (mor- pholin-4-yl-methyl) -isoxazolidin " Le A 24 - 55 - Use of substituted N-methylisoxazolidines of the formula (I) according to Claim 4, characterized in that they are used to combat felting. « 8. Use of substituted N-Methylisoxaaolidinen of the formula (I) according to claim 4, characterized in that they are used for controlling animal pests ·