The present invention relates to novel anthranilic diamide derivatives of the general formula (I)in which R1, R2, R3, R4, R5, R6, A, Q and n have the meanings given in the description, to their use as insecticides and acaricides for controlling animal pests, also in combination with other agents for activity boosting, and a plurality of processes for their preparation.

BACKGROUND

1. Field of the Invention

The present invention relates to novel anthranilic diamide derivatives, to their use as insecticides and acaricides for controlling animal pests, also in combination with other agents for activity boosting, and to a plurality of processes for their preparation.

2. Description of Related Art

In their application, however, the active compounds already known in accordance with the specifications identified above have disadvantages in some respects, whether it be that they exhibit a narrow spectrum of application or whether it be that they do not have satisfactory insecticidal or acaricidal activity.

SUMMARY

Novel anthranilic diamide derivatives have now been found which have advantages over the compounds already known, examples being better biological or environmental properties, broader application methods, an improved insecticidal or acaricidal activity, and also high compatibility with crop plants. The anthranilic diamide derivatives can be used in combination with other agents for improving the efficacy in particular against insects which are difficult to control.

The present invention accordingly provides novel anthranilic diamide derivatives of the formula (I)

two radicals R4furthermore form, via adjacent carbon atoms, the fused rings below which are optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another may be selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-halocycloalkyl, halogen, C1-C6-alkoxy, C1-C4-alkylthio(C1-C6-alkyl), C1-C4-alkylsulphinyl(C1-C6-alkyl), C1-C4-alkylsulphonyl(C1-C6-alkyl), C1-C4-alkylamino, di-(C1-C4-alkyl)amino and C3-C6-cycloalkylamino,

where the substituents independently of one another may be selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-alkyoxy, halo-C1-C6-alkyl, amino, (C1-C6-alkyl)amino, di-(C1-C6-alkyl)amino, C3-C6-cyclo alkyl,

where —(C3-C6-cycloalkyl)- in the ring may optionally contain 1 or 2 heteroatoms selected from the group consisting of N, S, O,R8represents straight-chain or branched —(C1-C6-alkylene)- or represents a direct bond,

where a plurality of R8radicals independently of one another represent straight-chain or branched-(C1-C6-alkylene)- or represent a direct bond,

where R′ represents alkyl, alkylcarbonyl, alkenyl or alkynyl which may optionally be mono- or polysubstituted by halogen,Qz represents a 3- or 4-membered partially saturated or saturated or a 5- or 6-membered partially saturated, saturated or aromatic ring or represents a 6- to 10-membered bicyclic ring system,

where the ring or the bicyclic ring system may optionally contain 1-3 heteroatoms from the group consisting of N, S, O,

or where the substituents independently of one another may be selected from the group consisting of phenyl and a 5- or 6-membered heteroaromatic ring, where phenyl or the ring may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy,R6represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-cycloalkoxy or

the compounds of the general formula (I) furthermore comprise N-oxides and salts.

If appropriate, the compounds of the formula (I) may be present in various polymorphic forms or as mixtures of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are provided by the invention and can be used according to the invention.

The compounds of the formula (I) optionally include diastereomers or enantiomers.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

where the substituents independently of one another may be selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-alkyoxy and halo-C1-C6-alkyl,

where Qz may have the general meanings given above or the preferred or particularly preferred meanings given below,A particularly preferably represents —CH2—, —CH2O—, —CH2OCH2—, —CH2S—, —CH2SCH2—, —CH2N(C1-C4-alkyl)-, —CH2N(C1-C4-alkyl)CH2—, —CH(Hal)-, —C(Hal)2-, —CH(CN)—, CH2(CO)—, CH2(CS)—, CH2CH(OH)—, -cyclopropyl-, CH2(CO)CH2—, —CH(C1-C4-alkyl)-, —C(di-C1-C6-alkyl)-, —CH2CH2—, —CH═CH—, —C≡C—, —C═NO(C1-C6-alkyl), —C(═O)(C1-C4-alkyl)-,A very particularly preferably represents —CH2—, —CH(CH3), C(CH3)2, —CH2CH2—, —CH(CN)—, —CH2O— or —C(═O)—CH2—,A especially preferably represents CH2, CH(CH3), —CH2O— or —C(═O)—CH2—,Qz preferably represents a 3- or 4-membered partially saturated or saturated ring or represents a 5- or 6-membered partially saturated, saturated or aromatic ring, where the ring may optionally contain 1-3 heteroatoms from the group consisting of N, S, O,

where the ring is optionally mono- or polysubstituted by identical or different substituents and where the substituents independently of one another may be selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl,Qz particularly preferably represents a 3- to 4-membered, partially saturated or saturated ring or represents a 5-membered partially saturated, saturated or aromatic ring, where the ring may optionally contain 1-2 heteroatoms from the group consisting of N, S, O,

which is optionally mono- or polysubstituted by identical or different substituents and where the substituents independently of one another may be selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl,R6preferably represents C1-C6-alkyl or represents the radical

R6particularly preferably represents methyl or represents the radical

R7independently preferably represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylsulphonyl or (C1-C4-alkyl)-C1-C4-alkoxyimino,R7independently particularly preferably represents hydrogen, halogen or C1-C4-haloalkyl,R7very particularly preferably represents fluorine, chlorine or bromine,R7especially preferably represents chlorine or bromine,p preferably represents 1, 2 or 3,p particularly preferably represents 1 or 2,p very particularly preferably represents 1,Z preferably represents N, CH, CF, CCl, CBr or CI,Z particularly preferably represents N, CH, CF, CCl or CBr,Z very particularly preferably represents N, CCl or CH,R8preferably represents straight-chain or branched —(C1-C4-alkylene)- or represents a direct bond,R8particularly preferably represents methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl or isobutyl or a direct bond,R8very particularly preferably represents methyl or ethyl or a direct bond,Q preferably represents a 5- or 6-membered partially saturated or saturated heterocyclic or heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system where the heteroatoms may be selected from the group consisting of N, S, O, where the ring or the ring system is optionally mono- or polysubstituted by identical or different substituents and where the substituents independently of one another may be selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, CO2H, CO2NH2, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl,

or where the substituents independently of one another may be selected from the group consisting of phenyl and a 5- or 6-membered heteroaromatic ring, where phenyl or the ring may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy,Q particularly preferably represents an optionally mono- or polysubstituted 5- or 6-membered heteroaromatic ring from the group consisting of Q-1 to Q-53 and Q-58 to Q-59, Q-62 to Q-63, an aromatic 9-membered fused heterobicyclic ring system Q-54 to Q-56 or a 5-membered heterocyclic ring Q-60 to Q-61 where the substituents independently of one another may be selected from the group consisting of C1-C3-alkyl, C1-C3-haloalkyl, C1-C2-alkoxy, halogen, cyano, hydroxyl, nitro and C1-C2-haloalkoxy,

or where the substituents independently of one another may be selected from the group consisting of phenyl and a 5- or 6-membered heteroaromatic ring, where phenyl or the ring may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy,Q very particularly preferably represents an optionally mono- or polysubstituted 5- or 6-membered heteroaromatic ring from the group consisting of Q-36 to Q-40, Q-43, Q-58 to Q-59, Q-62, Q-63, an aromatic 9-membered fused heterobicyclic ring system Q-54 to Q-56 or a 5-membered heterocyclic ring Q-60 to Q-61 where the substituents independently of one another may be selected from the group consisting of C1-C3-alkyl, C1-C3-haloalkyl, C1-C2-alkoxy, halogen, cyano, hydroxyl, nitro and C1-C2-haloalkoxy,

or where the substituents independently of one another may be selected from the group consisting of phenyl and a 5- or 6-membered heteroaromatic ring, where phenyl or the ring may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, NO2, C1-C4-alkoxy, C1-C4-haloalkoxy,Q especially preferably represents an optionally mono- or polysubstituted heteroaromatic ring from the group consisting of Q-37, Q-38, Q-39, Q-40, Q-43, Q-58, Q-59, Q-62 and Q-63 or a 5-membered heterocyclic ring Q-60 where the substituents independently of one another may be selected from the group consisting of chlorine, fluorine, iodine, bromine, cyano, trifluoromethyl and pentafluoroethyl,

or where the substituents independently of one another may be selected from the group consisting of phenyl and a 5- or 6-membered heteroaromatic ring, where phenyl or the ring may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, NO2, C1-C4-alkoxy, C1-C4-haloalkoxy,

The rings or ring systems listed above may optionally independently of one another be substituted by oxo, thioxo, (═O)═NH, (═O)═N—CN, (═O)2. Examples which may be mentioned are tetrahydrothiophene dioxide, imidazolidone.

In this case, the oxo group as substituent at a ring carbon atom means, for example, a carbonyl group in the heterocyclic ring. This also preferably comprises lactones and lactams. The oxo group may also be present at the hetero ring atoms, which may exist in various oxidation levels, for example in the case of nitrogen and sulphur, in which case they form, for example, the divalent groups —N(O)—, —S(O)— (also abbreviated as SO) and —S(O)2— (also abbreviated as SO2) in the heterocyclic ring. In the case of —N(O)— and —S(O)— groups, in each case both enantiomers are included.

In a heterocyclic ring, substituents other than the oxo group can also be attached to a heteroatom, for example a nitrogen atom, if a hydrogen atom at the nitrogen atom of the skeleton is replaced in the process. In the case of the nitrogen atom and also other heteroatoms such as, for example, the sulphur atom, there may also be further substitution with formation of quarternary ammonium compounds or sulfonium compounds.

The above-recited general radical definitions and elucidations or those recited in preference ranges may be combined arbitrarily with one another, in other words including combinations between the respective ranges and preference ranges. They apply both to the end products and, correspondingly, to precursors and intermediates.

Preference in accordance with the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferably).

Particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.

Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.

The compounds of the formula (I) may be present more particularly in the form of different regioisomers: for example in the form of mixtures of compounds having the definition Q-62 or Q-63 or in the form of mixtures of Q-58 and 59. The invention therefore also comprises mixtures of compounds of the formula (I) where Q has the meanings Q-62 and Q-63 and also Q-58 and Q-59 and the compounds may be present in various mixing ratios. Preference in this context is given to mixing ratios of the compounds of the formula (I) in which the radical Q is Q-62 or Q-58 to compounds of the formula (I) in which the radical Q is Q-63 or Q-59, of 60:40 to 99:1, particularly preferably of 70:30 to 98:2, very particularly preferably of 80:20 to 97:3. Especially preferred are the following mixing ratios for a compound of the formula (I) where Q has the definition Q-62 or Q-58 to the compound of the formula (I) where Q has the definition Q-63 or Q-59: 80:20; 81:19; 82:18; 83:17; 84:16; 85:15, 86:14; 87:13; 88:12; 89:11; 90:10, 91:9; 92:8; 93:7; 94:6; 95:5; 96:4; 97:3.

Preparation Processes

Anthranilamides of the formula (I)

in which A, R1, R2, R3, R4, R5, R6, Q and n have the meanings given above are obtained when benzoxazinones of the formula (II)

in which R4, R5, R6, A, Q and n have the meanings given above
are reacted with an amine of the formula (III)

in which R2and R3have the meanings given above
in the presence of a diluent.

The active compounds according to the invention, in combination with good plant tolerance and favourable toxicity to warm-blooded animals and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in animal husbandry, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector. They can preferably be used as crop protection compositions. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include:

From the class of the Bivalva, for example,Dreissenaspp.

From the order of the Chilopoda, for example,Geophilusspp.,Scutigeraspp.

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

From the order of the Dermaptera, for example,Forficula auricularia.

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

From the class of the Gastropoda, for example,Anionspp.,Biomphalariaspp.,Bulinusspp.,Derocerasspp.,Galbaspp.,Lymnaeaspp.,Oncomelaniaspp.,Succineaspp.

It is furthermore possible to control protozoa, such asEimeria.

From the order of the Isoptera, for example,Reticulitermesspp. andOdontotermesspp.

From the order of the Siphonaptera, for example,Ceratophyllusspp. andXenopsylla cheopis.

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

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

The effectiveness of the compounds of the formula (I) can be increased by adding ammonium salts and phosphonium salts. The ammonium salts and phosphonium salts are defined by formula (XI)

The ammonium salts and phosphonium salts of the formula (XI) can be used in a wide concentration range for increasing the effect of crop protection compositions comprising compounds of the formula (I). In general, the ammonium salts or phosphonium salts are used in the ready-to-use crop protection composition in a concentration of from 0.5 to 80 mmol/l, preferably 0.75 to 37.5 mmol/l, particularly preferably 1.5 to 25 mmol/l. In the case of a formulated product, the concentration of ammonium salt and/or phosphonium salt in the formulation is selected such that it is within these stated general, preferred or particularly preferred ranges following dilution of the formulation to the desired active compound concentration. The concentration of the salt in the formulation here is usually 1-50% by weight.

In one preferred embodiment of the invention, it is not an ammonium salt and/or phosphonium salt, but a penetrant, that is added to the crop protection compositions to increase the activity. An activity increase can be observed even in these cases. The present invention thus also provides the use of a penetrant, and also the use of a combination of penetrant and ammonium salts and/or phosphonium salts for increasing the activity of crop protection compositions which comprise acaricidally/insecticidally active compounds of the formula (I) as active compound. Finally, the invention also provides the use of these compositions for controlling harmful insects.

Suitable penetrants in the present context are all those substances which are usually used for improving the penetration of agrochemical active compounds into plants. Penetrants are defined in this context by their ability to penetrate from the aqueous spray liquor and/or from the spray coating into the cuticle of the plant and thereby increase the mobility of active compounds in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science51, 131-152) can be used for determining this property.

Suitable penetrants are, for example, alkanol alkoxylates. Penetrants according to the invention are alkanol alkoxylates of the formula
R—O-(-AO)v—R′  (XII)
in whichR represents straight-chain or branched alkyl having 4 to 20 carbon atoms,R′ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or n-hexyl,AO represents an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or represents mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals andv represents a number from 2 to 30.

A preferred group of penetrants are alkanol alkoxylates of the formula
R—O-(-EO—)n—R′  (XII-a)
in whichR has the meaning given above,R′ has the meaning given above,EO represents —CH2—CH2—O— andn represents a number from 2 to 20.

A further preferred group of penetrants are alkanol alkoxylates of the formula
R—O-(-EO—)p—(—PO—)q—R′  (XII-b)
in whichR has the meaning given above,R′ has the meaning given above,EO represents —CH2—CH2—O—,PO represents

p represents a number from 1 to 10 andq represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of the formula
R—O—(—PO—)r-(EO—)s—R′  (XII-c)
in whichR has the meaning given above,R′ has the meaning given above,EO represents —CH2—CH2—O—,PO represents

r represents a number from 1 to 10 ands represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of the formula
R—O-(-EO—)p—(—BO—)q—R′  (XII-d)
in whichR and R′ have the meanings given above,EO represents —CH2—CH2—O—,BO represents

p represents a number from 1 to 10 andq represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of the formula
R—O—(—BO—)r-(-EO—)s—R′  (XII-e)
in whichR and R′ have the meanings given above,BO represents

EO represents —CH2—CH2—O—,r represents a number from 1 to 10 ands represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of the formula
CH3—(CH2)t—CH2—O—(—CH2—CH2—O—)u—R′  (XII-f)
in whichR′ has the meaning given above,t represents a number from 8 to 13,u represents a number from 6 to 17.

As an example of an alkanol alkoxylate of the formula (XII-c), mention may be made of 2-ethylhexyl alkoxylate of the formula

in whichEO represents —CH2—CH2—O—,PO represents

andthe numbers 8 and 6 represent average values.

As an example of an alkanol alkoxylate of the formula (XII-d), mention may be made of the formula
CH3—(CH2)10—O-(-EO—)6—(BO—)2—CH3(XII-d-1)
in whichEO represents —CH2—CH2—O—,BO represents

Particularly preferred alkanol alkoxylates of the formula (XII-f) are compounds of this formula in whicht represents a number from 9 to 12 andu represents a number from 7 to 9.

With very particular preference, mention may be made of alkanol alkoxylate of the formula (XII-f-1)
CH3—(CH2)t—CH2—O—(—CH2—CH2—O—)u—R′  (XII-f-1)
in whicht represents the average value 10.5 andu represents the average value 8.4.

The above formulae provide general definitions of the alkanol alkoxylatyes. These substances are mixtures of substances of the stated type with different chain lengths. The indices are therefore average values which may also deviate from whole numbers.

The alkanol alkoxylates of the stated formulae are known, and some of them are commercially available or can be prepared by known methods (cf. WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).

Suitable penetrants also include, for example, substances which promote the solubility of the compounds of the formula (I) in the spray coating. These include, for example, mineral and vegetable oils. Suitable oils are all mineral or vegetable oils—modified or otherwise—which can usually be used in agrochemical compositions. By way of example, mention may be made of sunflower oil, rapeseed oil, olive oil, castor oil, colza oil, corn seed oil, cottonseed oil and soya bean oil or the esters of said oils. Preference is given to rapeseed oil, sunflower oil and their methyl or ethyl esters.

The concentration of penetrant can be varied within a wide range. In the case of a formulated crop protection composition, it is generally 1 to 95% by weight, preferably 1 to 55% by weight, particularly preferably 15-40% by weight. In the ready-to-use compositions (spray liquors), the concentrations are generally between 0.1 and 10 g/l, preferably between 0.5 and 5 g/l.

Inventively emphasized combinations of active compound, salt and penetrant are listed in the table below. Here, “according to test” means that any compound which acts as penetrant in the cuticle penetration test (Baur et al., 1997, Pesticide Science51, 131-152) is suitable.

If appropriate, the compounds according to the invention can, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural compounds impregnated with active compound, synthetic substances impregnated with active compound, fertilizers and also microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active ingredients with extenders, i.e. liquid solvents, and/or solid carriers, optionally with the use of surfactants, i.e. emulsifiers and/or dispersants, and/or foam formers. The formulations are produced either in suitable plants or else before or during application.

Suitable for use as auxiliaries are substances which are suitable for imparting to the composition itself and/or to preparations derived therefrom (for example spray liquors, seed dressings) particular properties such as certain technical properties and/or also particular biological properties. Typical auxiliaries include: extenders, solvents and carriers.

Suitable solid carriers are:

for example ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates; useful solid carriers for granules include: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic flours, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/or foam formers include: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or —POP ethers, acid and/or POP POE esters, alkylaryl and/or POP POE ethers, fat and/or POP POE adducts, POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl or aryl phosphates or the corresponding PO-ether adducts. Furthermore, suitable oligomers or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly)alcohols or (poly)amines. It is also possible to use lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and also their adducts with formaldehyde.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants such as alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Other possible additives are perfumes, mineral or vegetable oils which are optionally modified, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability, may also be present.

The formulations generally comprise between 0.01 and 98% by weight of active compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in its commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilizing agents, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.

A mixture with other known active ingredients, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or else with agents for improving the plant properties, is also possible.

When used as insecticides, the inventive active ingredients may also be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergists. Synergists are compounds which enhance the action of the active ingredients, without any need for the synergist added to be active itself.

When used as insecticides, the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with inhibitors which reduce degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in plant tissues.

The active ingredient content of the use forms prepared from the commercially available formulations may vary within wide limits. The active ingredient concentration of the application forms may be from 0.00000001 to 95% by weight of active ingredient, preferably between 0.00001 and 1% by weight.

The compounds are employed in a customary manner appropriate for the use forms.

All plants and plant parts can be treated in accordance with the invention. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can thus be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or cannot be protected by varietal property rights. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.

Treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on their surroundings, environment or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injection and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.

As already mentioned above, it is possible to treat all plants and their parts in accordance with the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms “parts” or “parts of plants” or “plant parts” have been explained above.

More preferably, plants of the plant cultivars which are each commercially available or in use are treated in accordance with the invention. Plant cultivars are to be understood as meaning plants having new properties (“traits”) and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They may be cultivars, biotypes and genotypes.

Depending on the plant species or plant cultivars, and the location and growth conditions (soils, climate, vegetation period, diet) thereof, the inventive treatment may also result in superadditive (“synergistic”) effects. For example, possibilities include reduced application rates and/or broadening of the activity spectrum and/or an increase in the activity of the compounds and compositions usable in accordance with the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or higher nutritional value of the harvested products, increased storage life and/or processibility of the harvested products, which exceed the effects normally to be expected.

The transgenic plants or plant cultivars (those obtained by genetic engineering) which are to be treated with preference in accordance with the invention include all plants which, through the genetic modification, received genetic material which imparts particular advantageous useful properties (“traits”) to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or a higher nutritional value of the harvested products, better storage life and/or processibility of the harvested products. Further and particularly emphasized examples of such properties are an improved defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active ingredients. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and other types of vegetable, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with particular emphasis being given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are emphasized in particular are increased defence of the plants against insects, arachnids, nematodes and slugs and snails by toxins formed in the plants, in particular those formed in the plants by the genetic material fromBacillus Thuringiensis(for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as “Bt plants”). Traits that are also particularly emphasized are the improved defence of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and correspondingly expressed proteins and toxins. Traits that are additionally particularly emphasized are the increased tolerance of the plants to certain active herbicidal ingredients, for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin (for example the “PAT” gene). The genes which impart the desired traits in question may also be present in combinations with one another in the transgenic plants. Examples of “Bt plants” include maize varieties, cotton varieties, soya varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance against glyphosate, for example maize, cotton, soya beans), Liberty Link® (tolerance against phosphinothricin, for example oilseed rape), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulphonylurea, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars which have these genetic traits or genetic traits which are still to be developed and will be developed and/or marketed in the future.

The plants stated can be treated particularly advantageously in accordance with the invention with the compounds of the general formula I or the active compound mixtures according to the invention. The preferred ranges stated above for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.

The active compounds according to the invention act not only against plant, hygiene and stored product pests, but also in the veterinary medicine sector against animal parasites (ecto- and endoparasites), such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas. These parasites include:

From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example,Trimenoponspp.,Menoponspp.,Trinotonspp.,Bovicolaspp.,Werneckiellaspp.,Lepikentronspp.,Damalinaspp.,Trichodectesspp. andFelicolaspp.

From the order of the Diptera and the suborders Nematocerina and Brachycerina, for example,Aedesspp.,Anophelesspp.,Culexspp.,Simuliumspp.,Eusimuliumspp.,Phlebotomusspp.,Lutzomyiaspp.,Culicoidesspp.,Chrysopsspp.,Hybomitraspp.,Atylotusspp.,Tabanusspp.,Haematopotaspp.,Philipomyiaspp.,Braulaspp.,Muscaspp.,Hydrotaeaspp.,Stomoxysspp.,Haematobiaspp.,Morelliaspp.,Fanniaspp.,Glossinaspp.,Calliphoraspp.,Luciliaspp.,Chrysomyiaspp.,Wohlfahrtiaspp.,Sarcophagaspp.,Oestrusspp.,Hypodermaspp.,Gasterophilusspp.,Hippoboscaspp.,Lipoptenaspp. andMelophagusspp.

From the order of the Heteropterida, for exampleCimexspp.,Triatomaspp. andRhodniusspp.,Panstrongylusspp.

From the order of the Blattarida, for exampleBlatta orientalis, Periplaneta americana, Blattella germanicaandSupellaspp.

From the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, for example,Argasspp.,Ornithodorusspp.,Otobiusspp.,Ixodesspp.,Amblyommaspp.,Boophilusspp.,Dermacentorspp.,Haemophysalisspp.,Hyalommaspp.,Rhipicephalusspp.,Dermanyssusspp.,Raillietiaspp.,Pneumonyssusspp.,Sternostomaspp. andVarroaspp.

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example,Acarapisspp.,Cheyletiellaspp.,Ornithocheyletiaspp.,Myobiaspp.,Psorergatesspp.,Demodexspp.,Trombiculaspp.,Listrophorusspp.,Acarusspp.,Tyrophagusspp.,Caloglyphusspp.,Hypodectesspp.,Pterolichusspp.,Psoroptesspp.,Chorioptesspp.,Otodectesspp.,Sarcoptesspp.,Notoedresspp.,Knemidocoptesspp.,Cytoditesspp. andLaminosioptesspp.

The inventive active ingredients of the formula (I) are also suitable for controlling arthropods which attack agricultural livestock, for example cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, honey-bees, other domestic animals such as, for example, dogs, cats, caged birds, aquarium fish, and experimental animals, for example hamsters, guinea pigs, rats and mice. The control of these arthropods is intended to reduce cases of death and reduced productivity (of meat, milk, wool, hides, eggs, honey etc.), and so more economic and easier animal husbandry is possible by use of the inventive active ingredients.

The active compounds according to the invention are used in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal administration, by dermal use in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active compound, such as collars, ear marks, tail marks, limb bands, halters, marking devices and the like.

When used for livestock, poultry, domestic animals and the like, the active ingredients of the formula (I) can be used as formulations (for example powders, emulsions, flowables) comprising the active ingredients in an amount of 1 to 80% by weight, either directly or after 100 to 10 000-fold dilution, or they may be used as a chemical bath.

It has also been found that the inventive compounds have strong insecticidal action against insects which destroy industrial materials.

Preferred but nonlimiting examples include the following insects:

Industrial materials in the present connection are understood to mean inanimate materials, such as preferably plastics, adhesives, sizes, papers and cards, leather, wood, processed wood products and coating compositions.

The ready-to-use compositions may optionally also comprise other insecticides, and optionally one or more fungicides.

With respect to possible additional partners for mixing, reference is made to the insecticides and fungicides mentioned above.

Moreover, the compounds according to the invention can be employed for protecting objects which come into contact with saltwater or brackish water, in particular hulls, screens, nets, buildings, moorings and signalling systems, against fouling.

Furthermore, the compounds according to the invention can be used alone or in combinations with other active compounds as antifouling compositions.

The active ingredients are also suitable for controlling animal pests in the domestic sector, in the hygiene sector and in the protection of stored products, especially insects, arachnids and mites, which are found in enclosed spaces, for example homes, factory halls, offices, vehicle cabins and the like. They can be used to control these pests alone or in combination with other active ingredients and auxiliaries in domestic insecticide products. They are effective against sensitive and resistant species, and against all developmental stages. These pests include:

From the order of the Scorpionidea, for example,Buthus occitanus.

From the order of the Araneae, for example,Aviculariidae, Araneidae.

From the order of the Opiliones, for example,Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example,Oniscus asellus, Porcellio scaber.

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

From the order of the Chilopoda, for example,Geophilusspp.

From the order of the Zygentoma, for example,Ctenolepismaspp.,Lepisma saccharina, Lepismodes inquilinus.

From the order of the Saltatoria, for example,Acheta domesticus.

From the order of the Dermaptera, for example,Forficula auricularia.

From the order of the Isoptera, for example,Kalotermesspp.,Reticulitermesspp.

From the order of the Psocoptera, for example,Lepinatusspp.,Liposcelisspp.

From the order of the Heteroptera, for example,Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household insecticides, they are used alone or in combination with other suitable active compounds, such as phosphoric acid esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.

Description of the Preparation Processes and Intermediates

Benzoxazinones of the formula (II) are known (e.g. WO2007/144100) or can be prepared by known methods.

Anilines of the formula (III) are known (e.g. WO2007/144100) or can be prepared by known methods.

PREPARATION EXAMPLES

The preparation processes described above can be used to give the compounds of the formula (I)—for example the following compounds of the formula (I):

Synthesis of 1-(3-chloropyridin-2-yl)-N-{4-cyano-2-[(1,1-dioxidotetrahydrothiophen-3-yl)carbamoyl]-6-methylphenyl}-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide

An amount of 100 mg (0.17 mmol) of 2-[1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazol-5-yl]-8-methyl-4-oxo-4H-3,1-benzoxazine-6-carbonitrile was dissolved in 5 ml of tetrahydrofuran, and 69.5 mg (0.51 mmol) of tetrahydrothiophene-3-amine 1,1-dioxide was added. The mixture was initially stirred at room temperature for 3 h and then at 70° C. for 3.5 h.

The examples below can be obtained in an analogous manner, some of the compounds of the formula (I) being present as regioisomers. With respect to the NMR data, the table below states the chemical shifts and the corresponding signal intensities; for example, for compound 1:

The log P values reported in the table above and in the Preparation Examples were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed-phase columns (C 18), with the following methods:

The LC-MS determination in the acidic range is carried out at pH 2.7 using the mobile phases 0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid), linear gradient from 10% acetonitrile to 95% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (having from 3 to 16 carbon atoms) with known log P values (the log P values were determined by the retention times using linear interpolation between two successive alkanones).

The lambda max values were determined in the maxima of the chromatographic signals using the UV spectra from 200 nm to 400 nm.

The MH+ signals were determined using an Agilent MSD system with ESI and positive or negative ionization.

The NMR spectra were determined using a Bruker Avance 400 fitted with a flow probe head (volume 60 μl). The solvent used was d6-DMSO, with tetramethylsilane (0.00 ppm) being employed as reference. The examples in the table above were recorded in d6-DMSO as solvent, with the exception of Examples No. 39 (DMF), No. 51 (CDCl3) and No. 69, which were recorded in CD3CN as solvent. The measuring temperature is 303K when the solvent used is d6-DMSO and 298K when the solvent used is CD3CN.

In individual cases, the samples were measured using a Bruker Avance II 600 or III 600.

USE EXAMPLES

Solvents:78parts by weight of acetone1.5parts by weight of dimethylformamideEmulsifier:0.5part by weight of alkylaryl polyglycol ether

Discs of Chinese cabbage (Brassica pekinensis) infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.

After 6 days, the activity in % is determined 100% means that all of the aphids have been killed; 0% means that none of the aphids have been killed.

In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g/ha, an activity of 100%: 10, 29, 30, 31, 37, 38, 39, 43, 57

In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 100 g/ha, an activity of 80%: 6, 27, 35, 41, 48, 54, 72, 87

In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 100 g/ha, an activity of 90%: 1, 7, 14, 20, 32, 44, 65, 97, 153, 193, 224, 231, 236

Solvents:78.0parts by weight of acetone1.5parts by weight of dimethylformamideEmulsifier:0.5part by weight of alkylaryl polyglycol ether

Discs of Chinese cabbage (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).

After 7 days, the activity in % is determined 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g/ha, an activity of 100%: 29, 30, 31, 32, 33, 37, 38, 39, 40

Solvents:78.0parts by weight of acetone1.5parts by weight of dimethylformamideEmulsifier:0.5part by weight of alkylaryl polyglycol ether

Discs of maize leaves (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with caterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the activity in % is determined 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g/ha, an activity of 100%: 29, 30, 31, 32, 33, 37, 38, 39, 40

In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 100 g/ha, an activity of 83%: 17, 178, 182

To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.

The active compound solution is injected into the abdomen (Boophilus microplus), and the animals are transferred into dishes and stored in a climate-controlled room.

After 7 days, the activity in % is determined. The activity is assessed by position of fertile eggs. 100% means that none of the ticks has laid any fertile eggs.

In this test, for example, the following compounds of the Preparation Examples show an activity of 100% at an application rate of 20 μg/animal: 24, 26, 27, 30, 31, 33, 36, 37, 38, 40, 42, 43, 44, 65, 69

To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulphoxide and the concentrate is diluted with water to the desired concentration.

Vessels containing horse meat treated with the active ingredient preparation of the desired concentration are populated with about 20Lucilia cuprinalarvae.

After 48 days, the kill in % is determined. 100% means that all of the larvae have been killed; 0% means that none of the larvae have been killed.

In this test, for example, the following compounds of the Preparation Examples show an activity of 100% at an application rate of 100 ppm: 24, 26, 27, 30, 31, 33, 36, 37, 38, 40, 42, 43, 44, 65, 69

To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulphoxide and the concentrate is diluted with water to the desired concentration.

Vessels containing a sponge treated with the active compound preparation of the desired concentration are populated with adultMusca domestica.

After 48 days, the kill in % is determined. 100% means that all of the flies have been killed; 0% means that none of the flies have been killed.

In this test, for example, the following compounds of the Preparation Examples show an activity of 80% at an application rate of 100 ppm: 26, 36, 37

In this test, for example, the following compounds of the Preparation Examples show an activity of 90% at an application rate of 100 ppm: 42

In this test, for example, the following compounds of the Preparation Examples show an activity of 100% at an application rate of 100 ppm: 38, 44

In this test, for example, the following compounds of the Preparation Examples show an activity of 100% at an application rate of 20 ppm: 27

In this test, for example, the following compounds of the Preparation Examples show an activity of 80% at an application rate of 20 ppm: 30, 65, 69

Solvents:78.0parts by weight of acetone1.5parts by weight of dimethylformamideEmulsifier:0.5part 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 amount of solvents and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. Discs of Chinese cabbage (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).

After the desired period of time, the activity in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy which is superior to the prior art: see table

Solvents:78.0parts by weight of acetone1.5parts by weight of dimethylformamideEmulsifier:0.5part 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 amount of solvents and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. Discs of maize leaves (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with caterpillars of the armyworm (Spodoptera frugiperda).

After the desired period of time, the activity in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy which is superior to the prior art: see table

Solvents:78.0parts by weight of acetone1.5parts by weight of dimethylformamideEmulsifier:0.5part by weight of alkylaryl polyglycol ether

Discs of Chinese cabbage (Brassica pekinensis) infected by all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.

After the desired period of time, the activity in % is determined. 100% means that all of the aphids have been killed; 0% means that none of the aphids have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy which is superior to the prior art: see table