DE19827611A1 - Use of aryl-alkylamino-pyrimidine compounds - Google Patents

Abstract

Use of arylalkylamino-pyrimidine compounds of formula (I), as insecticides, is new: R1 = H, halo, T, T', 3-7C cycloalkyl, TO,NH2 (optionally substituted by T), or 6-14C aryl (optionally substituted by 1-3 halo, R, RO or R'O); R2, R3 = H, halo or T; or R2+R3 = a 5-6 membered saturated or unsaturated ring which contains 1-2 N or S atoms; R4 = H, T, 3-7C cycloalkyl or R'; n = 1 or 2; R6 = H, halo, T, R' or TO; R5 = (a) when R6 is H: a group O-A1-CN or O-S(O)2R7; or (b) when R6 is H, halo, T, R' or TO: a group S(O)mR8; or R5+R6 = O-A2-O at positions 3 and 4 of the phenyl ring; A1 = 1-6C alkylene; R7 = T, R', 6-14C aryl, benzyl, styryl, or NH2 (optionally substituted by T); R8 = T (optionally substituted by RS or TO) or CF2R9; R9 = H or halo; A2 = methylene or ethylene (optionally substituted by 1-4 halo); T, T', R, R' = 1-6C alkyl, 1-6C haloalkyl, 1-4C alkyl and 1-4C haloalkyl respectively; m =0-2; provided that R4 is not a group R if R5 and R6 = O-A2- O.

Description

The present invention relates to the use of arylalkylamino derivatives of the general formula I.

where the substituents have the following meanings:
R ^{1 is} hydrogen, halogen, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₇ cycloalkyl group, a C ₁ -C ₆ alkoxy group, an amino group, which may be linked to a C ₁ -C ₆ alkyl group may be substituted or a C ₆ -C ₁₄ aryl group which may optionally have one to three substituents selected from the group consisting of halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ - Alkoxy and C ₁ -C ₄ haloalkoxy;
R ² , R ^{3 are} hydrogen, halogen, a C ₁ -C ₆ alkyl group or R ² and R ³ together form a 5- or 6-membered saturated or unsaturated ring which contains one or two heteroatoms from the group consisting of N and S. may contain;
R ^{4 is} hydrogen, a C ₁ -C ₆ alkyl group, a C ₃ -C ₇ cycloalkyl group or a C ₁ -C ₄ haloalkyl group;
R ⁵ when R ^{6 is} hydrogen,
OA ₁ -CN or -OS (= O) ₂ R ⁷ , where A _{1 is} a C ₁ -C ₆ alkylene group and R ^{7 is} a C ₁ -C ₆ alkyl group, a C ₁ -C ₄ halo alkyl group C ₆ -C ₁₄ aryl group, a benzyl group, a styryl group or an amino group optionally substituted with a C ₁ -C ₄ alkyl group, or
when R ^{6 is} hydrogen, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₄ haloalkyl group or a C ₁ -C ₆ alkoxy group,
a radical -S (O) _m -R ^8, wherein R ⁸ represents a C ₁ -C ₆ alkyl group, a with a C ₁ -C ₄ alkylthio group or a C ₁ -C ₆ -alkyl koxygruppe substituted C ₁ -C ₆ alkyl group or a CF ₂ R ⁹ group, wherein R ^{9 is} a hydrogen or a halogen atom
or R ⁵ and R ⁶ together form a group -OA ₂ -O at positions 3 and 4 of the phenyl ring, where A _{2 is} a methylene or ethylene group which is optionally substituted by 1 to 4 halogen atoms,
with the proviso that R ^{4 and} C ^{6 are} not C ₁ -C ₄ alkyl when R ⁵ and R ^{6 form} a group -OA ₂ -O,
m the value 0, 1 or 2 and
n is 1 or 2,
as insecticides.

EP-A 424 125 describes compounds of the general formula I and their use as fungicides.

In JP-A 36666/1984 and 68382/1989 further aralkylamine Described derivatives that have insecticidal and fungicidal activity point.

The object of the present invention was to develop compounds from the Group of aralkylamine derivatives with particularly good insecticides To find effect.

Surprisingly, this task was accomplished by the fiction appropriate use of the compounds of formula I solved.

This is surprising because in EP-A 424 125 the fun gicidal action of the compounds of formula I very strongly emphasized a possible insecticidal effect but no mention finds. Only in embodiment 16 is EP-A 424 125 an insecticidal activity of those claimed in this document Connections mentioned. However, this is the insecticidal effect inferior to the compounds used according to the invention.

Compounds of formula I in which the substituents have the following meanings are preferably used according to the invention:
R ^{1 is} hydrogen, C ₁ -C ₄ alkyl, C ₅ -C ₆ cycloalkyl, halogen, in particular hydrogen, methyl, ethyl or chlorine, especially hydrogen;
R ^{2 is} hydrogen, C ₁ -C ₆ alkyl, halogen, in particular methyl, ethyl, i- and n-propyl or chlorine, particularly preferably methyl, ethyl or isopropyl;
R ^{3 is} hydrogen, halogen, C ₁ -C ₆ -alkyl, in particular fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl, in particular chlorine, methyl, ethyl and i- and n-propyl, particularly preferably chlorine;
or
R ² and R ³ together form a 5- or 6-membered saturated or unsaturated ring which may contain one or two heteroatoms from the group consisting of N and S, particularly preferably a thiophene or a phenyl ring;
R ^{4 is} hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₇ cycloalkyl, C ₁ -C ₄ haloalkyl, preferably hydrogen, C ₁ -C ₃ alkyl and C ₃ -C ₆ cycloalkyl, be particularly preferred Hydrogen, methyl, ethyl, isopropyl, cyclopropyl, cyclopentyl and cyclohexyl;
R ⁵ when R ^{6 is} hydrogen:
OA ₁ -CN or -OS (= O) ₂ R ⁷ where
A _{1 is} a C ₁ -C ₆ alkylene group, in particular with 1 to 5 C atoms, such as methylene, 1-methylmethylene, ethylene, 1-methylene, 2-methylethylene, propylene, pentylene, preferably methylene, 1-methylmethylene, Ethylene and propylene and especially methylene, ethylene or propylene, and
R ^{7 is} a C ₁ -C ₆ alkyl group, in particular methyl, ethyl, propyl, isopropyl, n-, i-, tert. and sec. butyl, pentyl or isopentyl, a C ₁ -C ₄ haloalkyl group, in particular fluoromethyl, di fluoromethyl, trifluoromethyl or trichloromethyl, a C ₆ -C ₁₄ aryl group, in particular phenyl or benzyl, which may be with halogen , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxy may be substituted, or an amino group optionally substituted with a C ₁ -C ₄ alkyl group, such as amino, methylamino , Dimethylamino, ethylamino, diethylamino, propylamino, dipropylamino;
or if R ^{6 is} hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy:
S (O) _m -R ⁸ , where
R ^{8 is} C ₁ -C ₆ alkyl, especially methyl or ethyl, one with a C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio group substituted kylgruppe C ₁ -C ₄ -alkyl, z. B. 2-ethoxyethyl
or
CF ₂ -R ⁹ , where R ^{9 is} halogen or hydrogen, preferably what is hydrogen,
or if R ⁵ and R ^{6 form} a group OA ₂ -O-,
A ^{2 represents} fluoromethylene, difluoromethylene, fluorethylene, difluorethylene, trifluoroethylene or tetrafluoroethylene.

Exemplary are a number of preferred compounds in the Table 1 described below.

Table 1

Process for producing the verbin used according to the invention the formula I are known to the person skilled in the art and in the literature tur, z. B. described in EP-A 424 125. Because of closer individual Please refer to the explanations there.

According to the invention, the compounds of formula I are used to control animal pests from the class of insects, arachnids and nematodes. They can be used in plant protection as well as in the hygiene, storage protection and veterinary sectors to combat animal pests. They are particularly suitable for controlling the following animal pests:

• - Insects from the order of the butterflies (Lepidoptera) for example Agrotis ypsilon, Agrotis segetum, Alabama argilla cea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, cirphis unipuncta, cydia pomonella, dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insu lana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersi cella, Lambdina fiscellaria, Laphygma exigua, Leucoptera cof feella, Leucoptera scitella, Lithocolletis blancardella, lobe sia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseu doplusia includens, Rhyacionia frustrana, Scrobipalpula abso luta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumato poea pityocampa, Tortrix viridana, Trichoplusia ni and Zeira phera canadensis,
• - Beetles (Coleoptera), e.g. B. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Bla piniperda stophagus, Blitophaga undata, Bruchus rufimanus, Bru chus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebu losa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorr hynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc tata, Diabrotica virgifera, Epilachna varivestis, Epitrix hir tipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera fountain tennis, hypera postica, ips typographus, lema bilineata, Leina melanopus, Leptinotarsa decemlineata, Limonius californi cus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyl lopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria,
• - Two-winged (Diptera), e.g. B. Aedes aegypti, Aedes vexans, Anas trepha ludens, Anopheles maculipennis, Ceratitis capitata,  Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macella ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, fan nia canicularis, Gasterophilus intestinalis, glossina morsi tans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifo lii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lyco ria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagole tis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula ole racea and tipula paludosa,
• - Thrips (Thysanoptera), e.g. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
• - Hymenoptera, e.g. B. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testu dinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,
• Bugs (Heteroptera), e.g. B. Acrosternum hilare, Blissus leucop terus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus in termedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Ne zara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor,
• - Plant suckers (Homoptera), e.g. B. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce rosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopa lomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sap paphis mali, Schizaphis graminum, Schizoneura lanuginosa, Tria leurodes vaporariorum and viteus vitifolii,
• - Termites (Isoptera), e.g. B. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis,
• - Straight wing aircraft (Orthoptera), e.g. B. Acheta domestica, Blatta orien talis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melano  plus femur rubrum, Melanoplus mexicanus, Melanoplus sanguini pes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus,
• - Arachnoid such as arachnids (Acarina), e.g. B. Amblyomma america num, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoeni cis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius me Gnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllo coptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetra nychus pacificus, Tetranychus telarius and Tetranychus urticae,
• - Nematodes such as root gall nematodes, e.g. B. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming Nematodes, e.g. B. Globodera rostochiensis, Heterodera avenae, He terodera glycines, heterodera schachtii, heterodera trifolii, Stick and leaf flakes, e.g. B. Belonolaimus longicaudatus, Dity lenchus destructor, Ditylenchus dipsaci, Heliocotylenchus mul ticinctus, Longidorus elongatus, Radopholus similis, Rotylen chus robustus, Trichodorus primitivus, Tylenchorhynchus clay toni, Tylenchorhynchus dubius, Pratylenchus neglectus, Praty lenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.

The amount of active ingredient used to combat animal Pests are 0.1 to 2.0 in free field conditions preferably 0.2 to 1.0 kg / ha.

The compounds I can in the usual formulations leads, z. B. solutions, emulsions, suspensions, dusts, Powders, pastes and granules. The application form depends according to the respective purpose; in any case, it should be fine and uniform distribution of the Ver ensure loyalty.

The formulations are prepared in a known manner, e.g. B. by stretching the active ingredient with solvents and / or Carriers, if desired using emulsifier agents and dispersants, where in the case of water as Ver other organic solvents as auxiliary solvents can be used. As auxiliary agents come there for essentially: solvents such as aromatics (e.g.  Xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. Petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. Cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and what ser; Carriers such as natural rock powder (e.g. kaolins, Clays, talc, chalk) and synthetic stone powder (e.g. finely divided silica, silicates); Emulsifiers like not ionogenic and anionic emulsifiers (e.g. polyoxyethylene fatty al alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants agents such as lignin sulfite liquor and methyl cellulose.

Alkali, alkaline earth, ammonium come as surface-active substances salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsul fonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, Al kyl sulfates, alkyl sulfonates, fatty alcohol sulfates and fatty acids such as their alkali and alkaline earth salts, salts of sulfated Fatty alcohol glycol ether, condensation products of sulfonated Naphthalene and naphthalene derivatives with formaldehyde, condensate onproducts of naphthalene or naphthalene sulfonic acid Phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxy lated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl poly ether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates sate, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxy lated polyoxypropylene, lauryl alcohol polyglycol ether acetal, Sor bitester, lignin sulfite and methyl cellulose.

For the production of directly sprayable solutions, emulsions, Pastes or oil dispersions come from medium oil fractions rem to high boiling point, such as kerosene or diesel oil, further Coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. Benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated Naphthalenes or their derivatives, methanol, ethanol, propanol, Butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclo hexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. B. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, into consideration.

Powders, materials for spreading and dusts can be mixed or mixed joint grinding of the active substances with a solid Carrier are manufactured.

Granules, e.g. B. coating, impregnation and homogeneous granules te, can by binding the active ingredients to solid carriers getting produced. Solid carriers are e.g. B. mineral soils, such as silica gel, silicas, silica gels, silicates, talc, Kao lin, attackclay, limestone, lime, chalk, bolus, loess, clay, dolomite,  Diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ge ground plastics, fertilizers, such as. B. ammonium sulfate, ammo nium phosphate, ammonium nitrate, urea and herbal product such as cereal flour, tree bark, wood and nutshell flour, Cel Loose powder and other solid carriers.

The formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight of the active ingredient. The active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

Examples of formulations are:

• I. 5 parts by weight of a compound according to the invention 95 parts by weight of finely divided kaolin intimately mixed. Man he in this way holds a dusts that 5 wt .-% of Contains active ingredient.
• II. 30 parts by weight of a compound according to the invention are with a mixture of 92 parts by weight of powdered pebble acid gel and 8 parts by weight paraffin oil, which is on the surface this silica gel was sprayed, mixed intimately. Man receives a treatment of the active ingredient in this way good adhesion (active ingredient content 23% by weight).
• III. 10 parts by weight of a compound according to the invention are in dissolved a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mol of oleic acid-N-monoethanolamide, 2 parts by weight of calcium salt the dodecylbenzenesulfonic acid and 2 parts by weight of the plant approximately 40 moles of ethylene oxide to 1 mole of castor oil stands (active ingredient content 9 wt .-%).
• IV. 20 parts by weight of a compound according to the invention are in dissolved a mixture consisting of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the addition pro product of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 5 parts by weight of the adduct of 40 moles of ethylene oxide 1 mol of castor oil (active ingredient content 16% by weight).
• V. 80 parts by weight of a compound of the invention 3 parts by weight of the sodium salt of diisobutylnaphthalene-al pha-sulfonic acid, 10 parts by weight of the sodium salt Lignin sulfonic acid from a sulfite waste liquor and 7 parts by weight powdered silica gel well mixed and in one Hammer mill ground (active ingredient content 80% by weight).  
• VI. 90 parts by weight of a Ver according to the invention are mixed bond with 10 parts by weight of N-methyl-α-pyrrolidone and receives a solution that is used in the form of tiny drops is suitable (active ingredient content 90% by weight).
• VII. 20 parts by weight of a compound according to the invention are described in dissolved a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition pro product of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 Parts by weight of the adduct of 40 moles of ethylene oxide of 1 mole of castor oil. By pouring and fine Ver dividing the solution in 100,000 parts by weight of water is obtained an aqueous dispersion containing 0.02% by weight of the active ingredient contains.
• VIII. 20 parts by weight of a compound according to the invention are with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α sulfonic acid, 17 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight pul deformed silica gel well mixed and in a ham grind grinder. By finely distributing the mixture in 20,000 parts by weight of water are obtained from a spray mixture which Contains 0.1% by weight of the active ingredient.

The active ingredients as such, in the form of their formulations or the application forms prepared from it, e.g. B. in the form of di sprayable solutions, powders, suspensions or dispersers sions, emulsions, oil dispersions, pastes, dusts, litter averaging, granules by spraying, atomizing, dusting, ver sprinkle or pour. The application forms rich depending on the purposes; they should be in everyone If possible, the finest distribution of the active ingredient according to the invention ensure fabrics.

Aqueous application forms can be made from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) through Zu set of water to be prepared. For the production of emulsions, Pastes or oil dispersions can contain the substances as such or dissolved in an oil or solvent, using wetting, adhesive, Dispersants or emulsifiers can be homogenized in water. However, wetting, adhesive, Dispersing or emulsifying agent and possibly solvent or Oil existing concentrates are made for dilution are suitable with water.  

The drug concentrations in the ready-to-use Zu Preparations can be varied in larger areas. In all they are generally between 0.0001 and 10%, preferably between between 0.01 and 1%.

The active ingredients can also be used successfully in ultra-low-volume Procedure (ULV) can be used, where it is possible to form stungen with more than 95 wt .-% active ingredient or even the active ingredient without applying additives.

Oils of various types, herbicides, fun gicides, other pesticides, bactericides, given if necessary, only immediately before use (tank mix) be set. These agents can be used with the invention be mixed in a weight ratio of 1:10 to 10: 1.

The agents according to the invention can be used as Fungicides are also present together with other active ingredients e.g. B. with herbicides, insecticides, growth regulators, fungicides that or with fertilizers. When mixing the connections I or the agents containing it in the application form as fun In many cases, one obtains gicides with other fungicides Enlargement of the fungicidal spectrum of activity.

The following list of fungicides with which the compounds according to the invention can be used together is intended to explain, but not to limit, the possible combinations:

• - Sulfur, dithiocarbamates and their derivatives, such as Ferridi methyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese zinc ethylenediamine bis-dithiocarbamate, tetramethylthiuram disulfide, Ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate), Am monia complex of zinc (N, N'-propylene-bis-dithiocarbamate), Zinc (N, N'-propylene bis-dithiocarbamate), N, N'-polypropylene bis- (thiocarbamoyl) disulfide;
• Nitroderivatives, such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-Bu tyl-4,6-dinitrophenyl-isopropyl carbonate, 5-nitro-isophthalic acid re-di-isopropyl ester;
• - Heterocyclic substances, such as 2-heptadecyl-2-imidazolin-ace tat, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethyl phthalimidophosphonothioate, 5-amino-1- [bis- (dimethylami no) -phosphinyl] -3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-di thioanthraquinone, 2-thio-1,3-dithiolo [4,5-b] quinoxaline, 1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester,  2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benz imidazole, 2- (thiazolyl- (4)) benzimidazole, N- (1,1,2,2-tetra chloroethylthio) tetrahydrophthalimide, N-trichloromethylthio-te trahydrophthalimide, N-trichloromethylthio-phthalimide,
• - N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-rhodanme thylthiobenzthiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, Pyridine-2-thio-1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid anilide, 2-methyl furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid anilide, 2,4,5-trimethyl-furan-3-carboxylic acid anilide, 2,5-dime thyl-furan-3-carboxylic acid cyclohexylamide, N-cyclohexyl-N-me thoxy-2,5-dimethyl-furan-3-carboxamide, 2-methyl-benzoic acid re-anilide, 2-iodo-benzoic acid anilide, N-formyl-N-morpho lin-2,2,2-trichloroethyl acetal, piperazin-1,4-diylbis-1- (2,2,2-trichloroethyl) formamide, 1- (3,4-dichloroanilino) -1-formy lamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecyl-morpholine or its salts, 2,6-dimethyl-N-cyclododecyl-morpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpro pyl] -cis-2,6-dimethyl-morpholine, N- [3- (p-tert-butylphenyl) - 2-methylpropyl] piperidine, 1- [2- (2,4-dichlorophenyl) -4-ethyl- 1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, 1- [2- (2,4-dichloro phenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazol-yl- urea, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-tri azol-1-yl) -2-butanone, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H- 1,2,4-triazol-1-yl) -2-butanol, (2RS, 3RS) -1- [3- (2-chlorophene nyl) -2- (4-fluorophenyl) oxiran-2-ylmethyl] -1H-1,2,4-triazole, α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidine-methanol, 5-Bu tyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine bis- (p-chloro phenyl) -3-pyridinemethanol, 1,2-bis- (3-ethoxycarbonyl-2- thioureido) benzene, 1,2-bis (3-methoxycarbonyl-2-thiou reido) -benzene,
• - Strobilurins such as methyl-E-methoxyimino- [α- (o-tolyloxy) -o-to lyl] acetate, methyl-E-2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yl- oxy] -phenyl} -3-methoxyacrylate, methyl-E-methoxyimino- [α- (2- phenoxyphenyl)] - acetamide, methyl-E-methoxyimino- [α- (2,5-dime thylphenoxy) -o-tolyl] -acetamide,
• Anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- [4-Me thyl-6-cyclopropyl-pyrimidin-2-yl] aniline,  
• Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyr rol-3-carbonitrile,
• - Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphe nyl) acrylic acid morpholide,
• - and various fungicides, such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, Hexachlorobenzene, DL-methyl-N- (2,6-dimethyl-phenyl) -N-fu royl (2) alaninate, DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyace tyl) alanine methyl ester, N- (2,6-dimethylphenyl) -N-chlorace tyl-D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phe nylacetyl) alanine methyl ester, 5-methyl-5-vinyl-3- (3,5-dichlor phenyl) -2,4-dioxo-1,3-oxazolidine, 3- [3,5-dichlorophenyl (-5-me thyl-5-methoxymethyl] -1,3-oxazolidine-2,4-dione, 3- (3,5-dichlor phenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlor phenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cya no- [N- (ethylaminocarbonyl) -2-methoximino] acetamide, 1- [2- (2,4- Dichlorophenyl) pentyl] -1H-1,2,4-triazole, 2,4-difluoro-a- (1H- 1,2,4-triazolyl-1-methyl) -benzhydryl alcohol, N- (3-chloro-2,6- dinitro-4-trifluoromethyl-phenyl) -5-trifluoromethyl-3-chloro-2- aminopyridine, 1 - ((bis- (4-fluorophenyl) methylsilyl) me thyl) -1H-1,2,4-triazole.

Synthesis examples

The examples given in the synthesis examples below Writings were made with a corresponding modification of the output compounds used to obtain further compounds I. The Compounds thus obtained are in the tables below listed with physical details.

example 1 5-chloro-6-ethyl-4- (1- (4-cyanomethyloxyphenyl) ethyl-aminopyrimidine

3 g (0.0108 mol) of 5-chloro-6-ethyl-4- (1- (4-hydroxyphenyl) ethyl aminopyrimidine, 1.2 g (0.016 mol) chloroacetonitrile, 4 g potassium Carbonate and 0.4 g sodium iodide were six in 120 ml acetone Heated to reflux for hours. It was then concentrated, the Residue taken up in toluene and extracted with water. After drying was again concentrated and the residue obtained on silica gel (mobile phase cyclohexane: ethyl acetate 1: 1) chromatographed. 2.3 g (67.3% of theory) of the desired th product obtained as a colorless oil.  

Example 2 5-chloro-6-ethyl-4- (1- (4-methanesulfonyloxyphenyl) ethyl aminopyrimidine

To 3 g (0.0108 mol) of 5-chloro-6-ethyl-4- (1- (4-hydroxyphenyl) ethyl Amino-pyrimidine dissolved in 40 ml of pyridine were ice-cooled 1.6 g (0.014 mol) of methanesulfonyl chloride were added and three hours leave it at room temperature. Then the mixture added to water and extracted with toluene. After drying was concentrated and the residue obtained on silica gel (run medium: cyclohexane: ethyl acetate 1: 1) chromatographed.

There were 1.7 g (44.3%) of the desired compound as a colorless Get oil.

Examples of use Example 3 Contact effect on nematodes

When testing the contact effect on nematodes of the genus Cae norhabiditis caused the compound according to synthesis example 1 Lethar persistent even at application concentrations of 0.5 ppm the nematodes over the entire test period of 5 days.

Example 4 Contact effect on spider mites

Potted bush beans with a fully developed pair of leaves were sprayed to runoff point in a spray booth with an aqueous solution of the active ingredient from Example 1. For this purpose, the plants were guided over a running rail to the rotary table of the spray booth and sprayed on all sides with three differently oriented nozzles when 30 cm ^{3 of} active ingredient solution was applied. The spraying process took about 20 seconds. The plants were heavily infested with mites and abundant egg release.

The effect (% mortality) was assessed after 5 days using a binocular rated. It was determined whether all stages were even were recorded.

The plants were grown under normal conditions during the 5 days (20-30 ° C) stored in the greenhouse.

The lowest concentration at which mortality is still <80% was achieved was 40 ppm.

Example 5 Effect against aphids (Aphisfabae)

The effect against aphids was determined in an analogous manner. The lowest active substance concentration was found here 40 ppm.

Example 6

When testing the contact effect against rice leafhoppers (Nephotettix Sp) in an analogous manner on rice plants there was a threshold of action determined from 200 ppm.

Example 7 Effect against the tropical cattle tick

In experiments with Boophilus microphus, in which fully soaked Females of the genus for 5 minutes in an aqueous emulsion of the Active ingredient from Example I were immersed, both resulted good inhibition of egg laying as well as good mortality results on the larvae themselves.

Claims (1)

Use of compounds of the general formula I
where the substituents have the following meanings:
R _{1 is} hydrogen, halogen, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₇ cycloalkyl group, a C ₁ -C ₆ alkoxy group, an amino group, which may be linked to a C ₁ -C ₆ alkyl group may be substituted or a C ₆ -C ₁₄ aryl group which may optionally have one to three substituents selected from the group consisting of halogen,
C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy;
R ² , R ^{3 are} hydrogen, halogen, a C ₁ -C ₆ alkyl group or R ² and R ³ together form a 5- or 6-membered saturated or unsaturated ring which contains one or two heteroatoms from the group consisting of N and s may contain;
R ^{4 is} hydrogen, a C ₁ -C ₆ alkyl group, a C ₃ -C ₇ cycloalkyl group or a C ₁ -C ₄ haloalkyl group;
R ⁵ when R ^{6 is} hydrogen,
OA ₁ -CN or -OS (= O) ₂ R ⁷ , where A _{1 is} a C ₁ -C ₆ alkylene group and R ^{7 is} a C ₁ -C ₆ alkyl group, a C ₁ -C ₄ halo alkyl group C ₆ -C ₁₄ aryl group, a benzyl group, a styryl group or an amino group optionally substituted with a C ₁ -C ₄ alkyl group, or
when R ^{6 is} hydrogen, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₄ haloalkyl group or a C ₁ -C ₆ alkoxy group,
a radical -S (O) _m -R ^8, wherein R ⁸ represents a C ₁ -C ₆ alkyl group, a with a C ₁ -C ₄ alkylthio group or a substituted C ₁ -C ₆ alkoxy C ₁ -C ₆ -Alkyl group or
a CF ₂ R ⁹ group, where R ^{9 is} a hydrogen or a halogen atom,
or R ⁵ and R ⁶ together form a group -OA ₂ -O at positions 3 and 4 of the phenyl ring, where A _{2 is} a methylene or ethylene group which is optionally substituted by 1 to 4 halogen atoms,
with the proviso that R ^{4 and} C ^{6 are} not C ₁ -C ₄ alkyl when R ⁵ and R ^{6 form} a group -OA ₂ -O,
m the value 0, 1 or 2 and
n is 1 or 2,
as insecticides.