TW200530182A - Process for preparing acylurea derivatives, salts of these acylurea derivatives and their use as pesticides - Google Patents

Abstract

A process for preparing acylurea derivatives of the formula (I), where the symbols and indices have the meanings indicated in the description, in which a compound of the formula (II), in which the symbols and indices have the meanings indicated in the description, is reacted in the presence of a base with a compound of the formula (III), in which X is, R7 is (C1-C8)-alkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, (C3-C8)-cycloalkyl (C3-C6)-cycloalkyl-(C1-C4)-alkyl, aryl or heterocyclyl, where said groups are unsubstituted or substituted by one or more radicals from the group of halogen, CN and NO2: and R3, R4 have the meanings indicated for formula (I). The compounds of the formula (I) are in some cases novel and are suitable for controlling pests.

Description

200530182 (1) IX. Description of the invention [Technical field to which the invention belongs] The present invention relates to a method for preparing fluorenil derivatives, and the salts of fluorenil derivatives obtainable by this method, Composition and its use as a pesticide. [Prior art] Insecticidal urea derivatives are suggested in WO 2003/097604. These compounds are prepared by reacting an appropriate carboxyamidine with ethylenedichloride to produce an isocyanate and further reacting it with an amine to produce an N-fluorenil derivative. Isocyanate formation is possible only by reacting amidine with ethylenedichloride, but not with phosgene, resulting in high process costs. The object is therefore to provide a novel and advantageous synthesis of sulfonylurea derivatives. It has now been surprisingly found that the reaction of 4-haloalkylpyridine-carboxamide with carbamate or the same reactive compound produces very good yields and high purity N '-[4 -Haloalkylpyridinyl] carbonylurea. [Summary of the Invention] The present invention therefore has a method for preparing an N-disubstituted-N '-[4-haloalkylpyridyl (pyrimidinyl)] carbonylurea of formula (I),

-6- 200530182 (2) where A is CH or N; R is (C] -C 4) -fluorenyl; R2 is H or M; M is organic or inorganic cation; R3 is (Crh) (C3 alkynyl, (Ci-C8) -co-oxy, r Γ field group, (C3-fluorene and radical (C3-C6), C6) -alkynyloxy, (Gc) alkenyloxy, c3 · (Cl-C6) Γ group o (C &)-Cyclosyl group 6) fluorenyl group, 0-CH2- (C "C8) the last nine groups are unsubstituted or after one or more of 'where The most basic group, heterocyclic group, aryloxy group, heterocyclic oxy group, mono-substituted, or aryl group, heterocyclic group ^^ 2, square group, _〇-CH2-aryl2 ring group, -0 -CH2 · heterocyclyl, preferably unselected, or substituted with one or more, the last eight groups described in R4 are (c) -c8) fluorenyl, (c3-C6) blocks Radical (c3-c8) -circle radical, (C3C) 'field radical, (c3-c.-yuan, wherein the last five radicals are unsubstituted; generation, · (")-radical substitution, or Is aryl'heterocyclyl, cH ~ one or more R5 wherein the last four radicals are unsubstituted or H · heterocyclyl, or substituted; or multiple R6 groups are taken or R and R4 and adjacent N atoms ~ Or aromatic heterop ^^ 3, 8 member saturated, unsaturated soils, which may optionally further contain a further %% of steam 〇 Wang two selected from N, S and 〇 雑 atoms are unsubstituted or via ~ ^ Or more (C) -C 6)-200530182 (3) alkyl, (Κ6) -haloalkyl or R5 group substitution; R5 is _ prime, (C ^ Cd-alkoxy, (C ^ Cs ) -Haloalkoxy, S (O) n- (C) -C6) -alkyl, S (O) -haloalkyl, CN, COO (C, -C6) -alkyl, N02, N [( Ci-C6) -alkyl] 2, phenoxy, unsubstituted or substituted with one or more groups selected from () -alkyl, () -haloalkyl and halogen; R6 is R5, (Ci- C6) -yuan, (C) -C6) -halogen; m is 0 or 1, and η is 0, 1 or 2, which are reacted by a 4-halogen of formula (π) in the presence of a base Alkylpyrimidinylcarboxamide,

Where A, R1, R2, and m have the meanings indicated by formula (I), and a compound of formula (III), X-C〇-NR3R4 (III) where

200530182 R is (C 1-C 8 (Ci-C4) -alkyl,

Aryl, (C 3 -C 8) -Aiinyl, alkyl, aryl, heterocyclyl, radicals substituted from halogen, CN and No 2; and R 3 and R 4 have the formula (I) significance. The method of the present invention makes it possible to prepare a fluorenil derivative in a simple method under economically and ecologically favorable conditions. The starting compound of formula (II), 4-haloalkylpyridine (pyrimidinyl) carboxamide, is known and its preparation is described, for example, in WO-02 / 48 1 1 1, German patent application 102 23 274.1 and Ep-A-0 580 374. Compounds of formula (111) can be prepared by methods known to those skilled in the art, by continuous reaction of phosgene or other carbonic acid derivatives with compound η X and with appropriate nitrogen compounds such as secondary amines or hydroxylamines . These types of methods are disclosed, for example, in Houben-Weyl, Methoden der Organischen Chemie, Book E4. Carbamates of formula (III) can be prepared, for example, by reaction of a chloroformate or carbonate with an appropriate nitrogen compound, such as an amine or hydroxylamine. R7〇-C (O) -Cl + NHR3R4-^ R7〇-C (O) -NR3R4 (III) R7〇-C (〇) ---- 0-R7 + NHR3R4-^ R70-C (O) -NR3R4 ( III) This method is disclosed, for example, in Coll. Czech. Chem. Comm. 48 »3, 1983, 900-905 and EP-A0577 167 0-9- 200530182 (5) Preferred compounds of formula (III) are among them X is OR7 and R7 is unsubstituted or mono- or polyhalo (preferably F and / or C1) -substituted (C] -C6) -alkyl or (c3-c6) -alkenyl, phenyl or Benzyl, particularly preferred CH3, C2H5, i-C3H7, -CH2-CH = CH2, -CH2-CF3, CH2-CF2-CF2H, cci3, phenyl or benzyl, especially -CHr CH = CH2; AlkOAlk -; CH3 or C2H5. The mole ratio of amidamine (π) to compound (ln) is usually! ··; 1-1 · 1, preferably 1: 1 -1 · 〇 5, particularly preferably about 1: 1. As the base, hydrides, amidines, hydroxides and (C! -C6) -alcohols, alkyl lithium compounds, metal hydrides, alkali and alkaline earth metal carbonates and alkali metal and alkaline earth metal are preferably administered and Acetate, tertiary amine with Cl_C4_ alkyl and sterically hindered nitrogen base. Very good administration of Na (OCH3), K (OCH3), Na (〇C2H5), K (OC2H5), Krypton (0-Third Grade-C4H9), K (0-Third Grade-c4H9), Na (0-Positive- CsHh), KCO-E-CsU'NaCO-i-CsU'KCO-i-CsHH), NaH, LiN (i-C3H7) 2 (LD A), N a 〇 Η, K Ο Η, N a2 C 0 3 , K2C03, Na acetate, K acetate, triethylamine, 1,5-diazabicyclo [4.3.0] non-5-anhydrochloride (DBU). Very particularly preferred are Na (OCH3), KO (CH3), Na (0-tertiary-C4H9) and NaH, NaOH. In a preferred embodiment, the salt formation is at a reduced pressure, preferably a pressure in the range of 20 to 200 mbar, particularly preferably 30 to 150 mbar, especially 50 to 50 mbar. get on. At the same time, low-boiling products are preferably distilled from the reaction mixture, as this may allow complete formation of the amidine salt. Advantageously, the reduced pressure is selected so that compounds -10- 200530182 (6) such as Η 2 〇, C Η 3 Η, t B ut Ο Η or E t Ο Η have a boiling point lower than the reaction temperature 'and the boiling point of the solvent during the reaction Above temperature. It is also possible to use a mixture of several bases. Generally, from 1 to 1.1 ', preferably from 1 to 1.05, the equivalent of base is based on 1 equivalent of amidine. The method is usually performed in a solvent. A polar aprotic solvent is preferred, particularly N, N-dimethylformamide (DMF), N-methylpyrrolidone (NMMP), N.N-dimethylacetamide, dimethoxy Ethane, cyclobutane and tetrahydrofuran (THF), very particularly DMF and NMP. Mixtures of solvents can also be used. Generally, 1-20 weight equivalents of solvent are used per equivalent of amidine. The reaction temperature is usually between 0 and 100 ° C, preferably between 30 and 75 ° C. In a preferred embodiment, the reaction is carried out under reduced pressure, preferably at a pressure in the range of 20-200 mbar, particularly preferably 30-150 mbar, especially 50-150 mbar. At the same time, low-boiling products are preferably distilled off from the reaction mixture, so that the reaction may be completed. Advantageously, the reduced pressure is selected so that the boiling point of the compound R7〇Η such as CH3OH, tButOH, EtOH or CH2 = CH-CH2OH is lower than the reaction temperature, and the boiling point of the solvent is above the reaction temperature. The response usually takes from 1 to 4 hours. The treatment takes place by methods known to the person skilled in the art, for example by filtration or extraction, washing and drying, and where appropriate subsequent purification by chromatography. For amidines of formula (II) having R2 = H, the method initially produces the corresponding salt (R2 diM), which can be advantageously removed from the -11-200530182 (7) reaction mixture by filtration with a particularly high purity. Further processing can occur by methods known to those skilled in the art. For example, the precipitated product is filtered off, washed and dried. Compounds of formula (I) having = H can be released from salts of formula (I) by methods known to those skilled in the art, for example by reaction with acids such as HC1, H2S04, ch3co2h and h3po4. The terms used in formulae (I) to (III) are explained in more detail below. The term "halogen" includes fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine, and particularly preferably oxygen. (C1-C 4) -Cycyl "is a straight or branched chain hydrocarbon group having 1, 2, 3 or 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl, 1 · butyl, 2-butyl, isobutyl or tertiary-butyl, etc. An alkyl group corresponding to a larger range of carbon atoms means a straight or branched chain saturated hydrocarbon group, which includes the number of carbon atoms corresponding to the range described so far. The term "(Ci-Cs) -alkyl" therefore includes the aforementioned alkyl groups, and for example, pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl, heptyl, octyl and Tertiary-octyl. "(C] -C 4) -haloalkyl" is an alkyl group mentioned in "(c 丨 -C 4) -alkyl", one or more of which is a hydrogen atom Substituted with the same number of identical or different halogen atoms, preferably chlorine or fluorine), for example, mono-, di- or trifluoromethyl, 1- or 2-fluoroethyl, 2, 2, 2, trifluoro Ethyl, chloromethyl, trichloromethyl or -tetrafluoroethyl. The terms "alkenyl," and "alkynyl" having a range of carbon atoms as described at the beginning denote a straight or branched chain hydrocarbon group having a number of carbon atoms corresponding to the range described herein and containing at least one Poly-12-200530182 (8) bond at any position of the unsaturated group. (C3-C6) -alkenyl "is therefore, for example, allyl, 2-methyl-2-propenyl, 1 or 2-but Alkenyl, pentenyl, 2-methylpentenyl or hexene C 3 -C 6) -alkynyl "means 'for example' propargyl, 2-methyl-2-propynyl, 2-butynyl , 2-pentynyl, 2-methylpentynyl or hexynyl. (C3-C1G) -cycloalkyl "means a monocycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclo Hexyl, cycloheptyl, cyclooctyl, bicycloalkyl, such as probornyl or bicyclo [2.2.2.2] octyl 'or fused systems such as decahydronaphthyl. The term "(C3-C6) -cycloalkyl- (C) -C4) -alkyl" means, for example, cyclopropylmethyl, cyclopentylmethyl, alkylhexylmethyl, cyclohexylethyl and cyclohexyl Butyl. "(C 1 -C4) -alkoxy," and "(C 1 -C 8) -alkoxy" are ether groups whose hydrocarbon groups have the term "(C1-C8) -alkoxy, , And the meanings indicated by "(CbC8) -alkoxy". "(C3-C6) -alkenyloxy,", "(C3-C6) -alkynyloxy, '," (C3-C6) -Cycloalkoxy, and "(C4-C10) -cycloalkenyloxy, is an ether group 'having the term" (C3-C6) -alkenyl, "and" (C3-C6) -alkynyl ", "(C3-C6) -cycloalkoxy, and" (C4-C10) -cycloalkenyloxy "as indicated. The term "heterocyclyl," preferably means a cyclic group that may be fully saturated, partially unsaturated, or fully unsaturated or aromatic and may be substituted by at least one or more of the same or different atoms selected from nitrogen, sulfur, or oxygen Interrupted, although two oxygen atoms are not -13- 200530182 (9) can be directly adjacent, and there must still be at least one carbon atom in the ring, such as thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, Isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1, 3,4-triazole, 1,2,4-oxadiazole, 1, 2, 4-thiadiazole, 1 5 2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo [b] thiophene, benzo [b] furan, ind Indole, benzo [c] thiophene, benzo [c] furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzoisoxazole, benzoisothiazole, benzopyrazole, benzene Benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyridine, pyrimidine, darazine, 1,3,5-triazine, 1,2,4-triazine , 1,2,4,5-tetrazine, quinoline, isoquinoline, quinoline, quinazoline Oxaline, 1,8-pyridine, 1,5-pyridine, 1,6-pyridine, 1,7-pyridine, pyridine, pyridopyrimidine, purine, pyridine, 4-pyridine, D Piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropiran, isoxazolyl, or thiazolidine. Heterocyclics are particularly preferred as having one of three to six members and one to four selected from 0, S, or N Heteroatomic saturated, partially saturated, or aromatic ring systems, which must have at least one carbon atom present in the ring. Heterocyclyl is very particularly preferably pyridine, pyrimidine, (1,2,4) -oxadiazole, (1 , 3,4) -oxadiazole, pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyracline, dakoujing, B Isozoline, thiazoline, tetrahydrodifuran, tetrahydropyridine, morpholine, oxidine, piperine, pyrroline, pyrrolidine, oxazoline, thiazolidine, ethylene oxide And oxetan. "Aryl" preferably means an aryl group having 6 to 12, particularly preferably 6 to 10 carbon atoms, such as phenyl or naphthyl, and very particularly preferably phenyl.- 14- 200530182 (10) Symbols in formulae (I) to (III) The index preferably has the following meanings: A is preferably c Η. R1 is preferably () -alkyl substituted by F and / or C1 one or more times, particularly preferably cf3, chf2 or CF2C1, especially cf3. R2 It is preferably M or Y.

M is preferably a non-oxidizable inorganic or organic cation, particularly preferably Li, Na, K, Cs, Ca2 + / 2, N [()-alkyl] 4, such as N (CH3) 4, N (C2H5) 4. Very particularly preferred is Na. R3 is preferably () -alkylc6) -alkynyl, (Cl-C8) -alkoxy, (c3-c6) -dilutedoxy (c3-c6) -alkynyloxy, (c3-c8) -cyclo Alkyl, (c3-c8) _cycloethyl · (CrCd-alkyl, 0-CH2- (C3-C8) -cycloalkyl, where the last nine groups are unsubstituted or via one or more R5 group substitution, or aryl, heterocyclyl, aryloxy, heterocyclooxy, π Ku ^

A square group, a _〇_CH aryl group, a -CH2-heterocyclyl group, a -0_CH2 · heterocyclyl group, wherein the last eight f group is unsubstituted or substituted with one or more R6 groups. R is preferably (Ci-c8) -alkyl, (c3_c6) -alkenyl (cc 6) -alkynyl, (c 3-C 8) -cycloalkyl, (C 3-C 8) 0-soil Alkyl_ (cC6) -sinyl, wherein the last five groups are unsubstituted, substituted or substituted with-or R groups, or are aryl, heterocyclic, one: two, C Η heterocyclyl, wherein the last four radicals are unsubstituted by W. Generation or more than 1 纟

Ci-C R5 is preferably halogen, especially F, C1, 6

** 15 200530182 (11 (Ci-Ce) -haloalkoxy. R6 is preferably R5, (C) _C6) -alkyl, (Ci_C6) _haloalkyl. R7 is preferably unsubstituted or mono- or Polyhalo (preferably F and / or Cl) -substituted (Cl-C6), alkyl or (C3-C6) -alkenyl, phenyl or benzyl 'is particularly preferably ch3, C2H5, i.C3H7 , -Ch2-ch = ch2, -ch2-phenyl or benzyl, especially ch3 CF3 'CH2-CF2-CF2H' CC13 or c2H5. X is preferably -0-R7. M is preferably 0. η is more It is preferably 0, 1, or 2. Preferred compounds of the formulae (I) to (111) are those compounds in which the symbols and indicators have better meanings. The compounds of the formula (I) are known in some examples and are Some examples are novel. The invention therefore also relates to compounds of formula (I) ', i.e. formulas (la), (lb) and (Ic), CF, 〇

NT, C,

〇II 3 4 nc-nr3r4 H (la) NI (〇) r where R3, 4R, and m have the meaning indicated by formula (I) -16- 200530182 (12) yb I / IV Formula 彐Township Department of Land Samples

o = c NIH

R4 r3r N \ — / ο m \ n / N——〇 where R11 is (CrC *)-haloalkyl group other than cf3, preferably CHf2 or cf2ci; and A, R3, R4, m have the formula (ϊ ). The invention further relates to compounds of formula (Ic), A ~ c, n4-CaM (Ic) (0) m, where M is preferably an inorganic or organic cation, more specifically Li, K, Cs, l / 2Ca, N [(Ci-C4) _yuanji] 4, such as ^ (CH3) N (C2H5) 4, very particularly preferably Na, K, and Li; and A, R1, R3, R4, and m have the formula (I ). Preferred compounds of formula (I a) · (I c) are those in which the symbols and refer to have the preferred meanings indicated by formula (I). -17- 200530182 (13) "Insecticide" means activity against harmful arthropods such as insects and mites, and worms such as nematodes, unless the context clearly indicates otherwise. The compound of formula (I) 'is suitable for controlling animal pests, especially insects, mites and worms, and is preferably used for controlling insects and insects encountered in agriculture, livestock raising, forestry, storage of goods and materials, and health care areas. Mites, and have good plant tolerance and favorable toxicity to warm-blooded species. It is active against normally sensitive and drug-resistant species and against all or individual stages of development. The above pests include: selected from Acarina, such as Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp. Hyalomma spp ·), Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp ·, Tarsonemus spp. , Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., True Eutetranyhus spp. ° is selected from Isopoda, for example, Oniscus aselus, Armadium vulgare, Porcellio scaber. -18- 200530182 (14) is selected from the order Dipip 1 ο ρ 〇da, for example, BI aniu 1 us guttulatus o is selected from the order Chilipoda, for example, Geophilus carpophagus and Scutigera spp .). Selected from Symphyla, for example, S cut i ger el 1 a immaculata o selected from Thysanura, for example, Lepisma saccharina, Taiwan o selected from 5 Collembola, for example, Onychiurus arm atu s ° is selected from Orthoptera, for example, Blata orientalis, Periplaneta americana, Leucophaea madeira, Blattella germanica, Ac h eta domesticus), Gry llotalpa spp., Locusta migratoria migratorioides, Melanoplus differentials, and S chi stocerca gregari a ° are selected from Isoptera, for example, Reticulitermes spp. 〇 selected from Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp.), Linognathus spp. 〇 selected from the order of the order of the order of the Order of the Order of the Mallophaga (Mallophaga), for example, 19-200530182 (15) (Trichodectes spp.), Damalina sp p. O is selected from Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci ° is selected from Heteroptera, for example, Eury gaster spp.), (Dy sdercus intermedius),

Piesma quadrata, temperate bed bug (Cimex lectularius), spring red cone spring (Rhodnius prolixus), and Triatoma spp. Chosen from the group of Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humu 1 i, Rice wheat worm tooth (Rhopal osiphum padi), Empoasca spp., E usce 1 us bilobatus, Nephotettix cincticeps, (Lecanium comi), hard-boiled worm ( Saissetia oleae), Laodelphax striatellus 51, Nilaparvata lugens, A. nidie 11 a aurantii, Aspidiotus hederae, Aspidiotus hederae, Pseudococcus spp.), Wood 1¾ genus (Psylla spp ·) 0 -20- 200530182 (16) selected from the order Lepid op ter a, for example, cotton bollworm (Pectinophora gossypiella), Bupalus pinianrius, Winter rule moth (Cheimatobia brumat a), (Lithocolletis blancardella), Apple · nest moth (Hyponomeuta padella), Small leaf moth (Plutella maculipennis), Sperm caterpillar (Malacosoma neustria), protozoa, yellow worm ), Ly mantr iaspp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana ), Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera frugiperda Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chile sp p., Pyrausta nubilalis ), Mediterranean pupa (Ephestia kuehniella), fiber moth (Galleria mellonella), Cacoecia podana, Capua reticulana Chori stoneura fumiferana, C 1 ysia ambiguella, Homona magnanima, Tortrix viridana ° selected from Coleoptera, for example, Ale η obi υ m punctatum), Rhizopertha dominica, Bruch idius obte ctu s, Phaseolus -21-200530182 (17) (Acanthoscelides obtectus), Hylotrupes bajulus, Acacia Agelastica alni), potato beetle (Leptinotarsa decem 1 ineata), (Phaedon cochleariae), spp. (Diabrotica spp.), Psylloides chrysocephala, Epilachna varivestis, Atomaria spp. Oryzaephilus surinamensis), Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Cabbage pod weevil (Ceuthorrynchus assimilis), Alfalfa (Hypera postica), Dermestes spp., Variegation Genus (Trogoderma), Anthrenus spp ·, Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Gibbium psylloides (Tribolium spp ·), Tenebrio molitor, Agriotes spp., Conoderus spp ·, Total beetle (Melolontha melolontha), Amphimallon solstitialis, Costelytra zealandica. It is selected from Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Mono morium pharaonis, and Vespa spp .) ° is selected from Diptera, such as Aedes -22- 200530182 (18) spp., Anopheles spp., Culex spp., Drosophila (Drosophila m elan ogaster), Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Chrysomyia spp. Cuterebra spp.), Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., T abanus spp., Tannia spp ·, Bibio hortulanus, Swedish rope (Oscinella frit), Phorbia spp., Pegomy ia hyoscyami, Mediterranean fruit fly (Ceratitis capitata), (Dacus oleae), (Tipula paludosa) 〇 selected from the order Si (Siphonaptera), for example , Xenopsylla cheopis, Ceratoph yllus spp ·). From the group of Arachnida, for example, Scorpio maurus and Latrodectus mactans ° From the helminths, for example, Haemonchus Trichostrongulus, Oostertagia, Cubaeria, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Red Trichomonas (Hyostrongulus), Ancylostoma, Anaplasma and Heterakis, and -23- 200530182 (19) Fasciola. From the group of Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galbaspp. (Succinea s pp.), Biomphalaria spp., Bulinus spp., Oncomelania spp. 〇Selected from Bivalva, for example, Dreissena spp. Protozoa may be controlled, such as Eimeria. Plant parasitic nematodes that can be controlled according to the present invention include, for example, the root-parasitic soil-dewlling nematodes, such as, for example, M e 1 oidogyne (root-knot nematodes, such as Meloidogyne incognita), Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes such as Globodera rostochiensis), potato cyst nematodes (Globodera pallida), Heterodera trifolii, and Radopholus, for example, R. patulosa L. nematode (R ad 〇ph ο 1 ussimi 1 is), Pratylenchus, such as Pratylenchus neglectus , Root rot nematodes (Pratylenchus penetrans) and Pratylenchus curvitatus; genus TyUnchi ^ s such as citrus nematodes (Tylenchulus -24-200530182 (20) semipenetrans), dwarf nematodes (Ty 1 enchorhynchus), for example Tylench orhynchus d υ b i u s and Tylenchorhynchus claytoni, Rotylenchus such as Rotylenchus robustus, Heliocotylenchus such as

Haliocotylenchus multicinctus, Belonoaimus e.g. Belonoaimus 1 ο n g i c a u d at u s' Longidorus e.g. Longidorus elongatus, Trichodorus e.g.

T r i c h o d o r u s p r i m i t i v u s and X i p h i n e m a) such as Xiphinema index °

Other nematodes that can be controlled using the compounds according to the invention are Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes) such as Aphelenchoides ritzemabosi and Anguina (flower and leaf tumor nematodes such as Anguina tritici) ° The compounds according to the present invention are preferably suitable for controlling stinger mouthpart insects such as parasitic insects (eg Beet (Aphis fabae), Apple (Aphis pom i), Spiraea worm tooth (Aphis spiraecola), Cotton worm tooth (Aphis gossypii), Aphas nasturtii, Dysaphis plantaginea, chicken Eriosoma SPP ·, Rhodolosiphum padi, Acyrthosiphon pisum, P emphigus bursarius, Myzus persicae, Myzus- 25- 200530182 (21) nicotianae), Myzus euphorbiae, Phylloxera spp. ), Toxoptera spp, Brevicoryne brassicae, Macrosiphum avenae, Macrosip hum euphorbiae, Nasonovia ribisnigri Sitobion avenae), Brachycaudus helychrysii, Phorodon humuli, Cicada (Idioscopus clypealis), S caphoides titanus, Empoasca onuki, Empoasca vitis , Potato leafhopper (Empoasca de vastans), Empoasca 1 ibyca, cotton leafhopper (Empoasca bi guttul a), cotton leafhopper (Empoasca faciais) or leafhopper (Erythroneura spp), genus (Hercinothrips femoralis), Scirtothrips aurantii, Scirtothrips dorsalis, Frankliniella schultzei, Frankliniella fusca, frankliniella occidentalis, western suma Frankliniella tritici), Kakothrips spp., Southern Yellow Ιίί Horse (Thrips Palmi), Rice Thrips (Thrips Or yzae) or Thrips Tabaci or whitefly (Aleurodes brassicae), Xuecao powder 1¾ (Bemisia tabaci), greenhouse powder 1¾ (Trialeurodes vaporariorum), Aleurodes proletella, and mealybugs ( Dysmicoccus spp., Planococcus spp., Phenacoccus spp. 0 -26- 200530182 (22) The present invention also relates to compositions such as pesticides, preferably Insecticidal, acaricidal and nematicidal, particularly good insecticidal and acaricidal compositions, which include one or more compounds of formula (I), in addition to suitable formulation adjuvants. To prepare the composition according to the invention, the active compound and other additives are combined and made into a suitable use shape. Generally, the composition according to the invention comprises from 1 to 95% by weight of a compound of formula (0). They can be formulated in different ways, depending on biological and / or chemical-physical parameters. The following are examples of possible formulations: Wet powder (WP), emulsifiable concentrate (EC), aqueous solution (SL), emulsion, sprayable solution, oil- or water-matrix dispersion (SC), suspension emulsion (sus ρ 〇emu 1 si ο n) (SE), powder (DP), soaking product, particles in the form of particles, spray particles, coating particles and adsorbing particles, water-dispersible particles (WG), ULV formulation, microcapsules, wax or bait. Each of these Other types of formulations are known in principle and described, for example: Winnacker-Kuchler, "Chemische

Technologie "[Chemical Technology], Volume 7, C.

Hauser Verlag Munich, 4th Edition 1 9 86; van Falkenberg, "Pesticides Formulation", Marcel Dekker NY 5 2nd Edition 1972-73 i K.Martens 5 u Spray Drying Handbook, ', 3rd Edition 1979, G. Goodwin Ldt. London . Necessary formulation adjuvants, in other words, carrier substances and / or interfacial active substances such as inert substances, surfactants, solvents and other additives are also known and described, for example, Watkin, "Handbook of -27- 200530182 ( twenty three)

Insecticide Dust Diluents and Carriers "5 2nd Ed, Darland Books, Caldwell NJ; H. v. Olphen, Introduction og Clay Colloid Chenistry", 2nd Ed, J. Wiley & Son, NY; Marsdeη, "Solvents Guide", Interscience, NY, 1 950; McCutcheon's, "Detergents and Emulsifiers

Annual '', MC Pul. Corp., Ridgewood, NJ; Sisley and Wood, "Encylcopedia of Surface Active Agents,", Chem. Pul. Co. Inc., NY1964; Schonfeldt "Grenzflachenaktive Athylenoxidaddukte55 [Surface-active ethylene oxide adducts], Wi ss V erlagsgesell., Stuttgart 1 967;

WinnackerKuchler '”Chemische Technologie”, Volume 7' C. Hauser Verlag Munich, 4th Edition 1986 o Based on these formulations, it is also possible to prepare compositions with other pesticidally active substances, fertilizers and / or growth regulators, such as spares -Mixture formulations or tank mixtures. Wettable powders are formulations that are uniformly dispersed in water. In addition to active compounds, they also include wetting agents such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, and alkyl groups. Sulfonates or alkylsulfonates, and dispersants, such as sodium ligninsulfonate or sodium 2,2, -dinaphthylmethane 4,6, · disulfonate, except for diluents or inert substances. Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, such as, for example, As an emulsifier, one or more emulsifiers can be used. For example, the following can be used, for example: calcium alkylarylsulfonate such as calcium monoalkylbenzenesulfonate, or nonionic emulsifier such as fatty acid polyol-28- 200530182 ( 24) Ester, alkylaryl polyglycol ether, fatty alcohol polyglycol ether, propylene oxide / ethylene oxide condensation, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan Fatty acid ester or polyoxyethylene sorbitan ester. Powders can be obtained by honing the active compound with a fine solid substance such as talc or natural clays such as kaolin, bentonite and pyrophillite, or diatomaceous earth. The granules can be applied to a carrier substance (such as sand) by atomizing the active compound onto a particulate inert substance that has the ability to adsorb, or via an adhesive (such as polyvinyl alcohol or sodium polyacrylate, or mineral oil) , Kaolin or granulated inert substances). Appropriate active compounds can also be prepared in the conventional manner for the preparation of fertilizer granules, if desired, as a mixture with fertilizers. In the wettable powder, the active compound concentration is usually about 10 to 90% by weight, and the balance to 100% by weight is composed of a conventionally formulated composition. In the emulsifiable concentrate, the active compound concentration may be about 5 to 80% by weight. Formulations in the form of a powder usually comprise 5 to 20% by weight of active compound, and the solution can be sprayed at about 2 to 20% by weight. In the case of granules, the content of the active compound depends in part on whether the active compound is in liquid or solid form and the granular adjuvants, fillers and the like used. In addition, the above-mentioned active compound formulations in each case include, where appropriate, conventional thickeners, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carrier substances. For use, concentrates in the form of commercially available 'if necessary, diluted in a conventional manner, such as in wettable powders, emulsifiable concentrates, dispersion-29-200530182 (25) solution and also in some microparticles Dilute with water in case. Preparations in the form of powders and granules and sprayable solutions are usually not further diluted with inert substances before use. The desired application rate varies depending on external conditions, such as temperature and humidity in particular. It can be varied within broad limits, for example, between 0.0005 and 10.0 kg / ha or more of the active compound, but preferably between 0.0001 and 5 kg / ha . The active compounds according to the invention, in their commercially available formulations and in the use forms prepared from such δ-week formulations, can be combined with other active compounds (such as other insecticides, attractants, disinfectants, nematicides, pesticides Mites, fungicides, growth regulators or herbicides). Preferred ingredients in the mixture are, for example: fungicides: 2-phenylphenol; 8-hydroxyquinoline sulfate; acibenzolar-s-methyl; aldimorph; Midoflumet; ampropy Ifos; andongsong-potassium; andoprim; anilazine; azaconazole; azoxystrobin Benalaxyl; benodanil; benomyl; benthiavalicarb-isopropyl; benmacril .; benamaril-isobutyl Bilanafos; binapacryl; biphenyl; bitertanol; b U sticidi η-s; bromogram -30- 200530182 (26) (bromuc ο na ζ ο 1 e); bupirimate; buthiobate; butylamine; Poly (p 〇1 ysu 1 phide) brocade; capsomycin (capsimycin); tetrachlorodane (c ap taf ο 1 ); Captan; carbendazim; carboxin; carpropamid; carvone; methyl acaricide (c hinomethionat); chlobenthiathiazone; chlorfenazole; chloroneb; chlorothalonil; chlozolinate; clozylacon ; Cyazofamid; cyflufenamid; cy moxani 1; cyproconazole; cyprodinil; cyprofuram; Dagger G Debacarb; difa 1 of 1 u an id; dichlone; dichlorophen; dichlorophen; dilocymet; dilomezine; large Bad (dicloran); diethofencarb (difenoconazole); diflumetorim; dimethirimol; dimethomorph; dimoxy strobin; Diniconazole; Dakli-M; dinocap; diphenylamine, dipyrithione; ditali mfos; dithianon; dodine; enemy Drazoxolon • 'edifenphos; epoxiconazole; ezoxiconazole (e thaboxam); Erimore-31-200530182 (27) (ethirim ο 1), Etridiazole; famoxadone; fenamidone; fenapanil Mo (fenarimo 1); fenbuconazol e; fenfuram; -M- fenhexamid: fenoxanil; fenoxanil 9 fenoxanil fenpiclonil); fenpropidin, fenpropimorph; ferbam; fl u az: inam; flubenzimine; fludioxonil; Flumeto ver; f 1 um o rp h i fluoromide 9 fluoxastrobin; fluquinconazole; flurprimidol; flusilazole) y flu isulfamide, f 1 ut o 1 an i 1, 9 flutr i afo 1, folpet, fosetyl -a 1 Forsaide-sodium; fuberidazole ); Furas (fura 1 ax y1); furamet (fur ametpy r); furcarbanil (furcarbanil); furmecyclox (guazatine); chlorobenzene (hexachlorobenze ine); Fickley (hexaconazole) hymexazo 1; imaza 1 i 1; imibenconazo le; iminoctadine diacetate; biguanyl octyl phenyl sulfamate < 〔Tri (albesile; iodocarb); econazole (ip CO] aaz ο 1 e); propyl xylasone (iprobenfos) > iprodione () iprodione; ) (iprovalicarb) >Irumamycin; Si Proprothiolane; Ivaledione; Kasugamycir i; kresoxim-methyl ; Zinc manganese (mancoze: b), f maneb (maneb); meferimzone; mepanipyrim ;: mepronil; metalaxyl; metol al axy 1 -M) metcona zole); methasulfocart 丨; methfuroxam; metiram; metominostrobin; metsulfovax 5 mildiomycin; mikeny ( my clobutanil) myclozolin; natamycin; nicobifen; nicobifen-isopropyl; no vi flumuron; noriflumuron nuarimol) • 'ofurace; of: orysastrobin; of oxadixyl; of oxalic acid, of: oxpoconazol e; oxcaroxin (oxycarboxin); oxyfenthiin) 9 palobutrazole; pefurazoate 9 penconazole; pencycuron y phosdiphen; phthalide; picoxy strobin ); Piperalin; polyoxorim; polyoxorim 9 probenazole; prochloraz 9 procymi done); propamocarb; propa nosine-sodium; puckley-33- 200530182 (29) (propiconazole); propine b; puna- \ j (proquinazi d); prothioconazo le 5 white and lacractrol bin: pyrrazoph 〇s; f-fino (pyifenox); bifenir (pyrimethani 1) ;: Peracron (pyroquilon); pyroxyfur; pyrrolnitrin; quinconazole 9 quinoxyfen; quintozene; simeconazole: Spiroxamine »sulfur & tebuconazole: tecloftalam; tecnazene; tetcyclacis 9 tetraconazole; thiabendazol e ) 9 thicyofen; thifluzamide; thiophanate-m ethyl; thiram; tioxymid; tolclofos-methyl ; Tolylfluanid; triadimefon; triadimenol; triazbutil; > tri azoxid e; tricyclamide (tricyclazole); tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole fene: uniconazole; uniconazole丨 mycin A (validamycin A); vinclozolin; zi neb; zi neb; zi ram; zoxamide; (2S) -N- [2- [ 4-[[3- (4-chlorophenyl) · 2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2-[(methylsulfonyl-34 -200530182 (30) yl) amino] butylamidine; 1- (1-naphthyl))-1H -pyrrole-2,5 · dione; 2,3,5,6-tetrachloro-4- ( Methylsulfonyl) -pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolylcarboxamide; 2-chloro (2,3-dihydrolH3-trimethyl-1 Hydrazone-section-4 -yl) -3 -pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; acti no vat e; cis -1-(4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol; (2,3-dihydro-2,2-dimethyl- 1H-indene · 1-yl) -1H-imidazole-5-carboxylic acid methyl ester; monopotassium carbonate; N- (6-methoxy-3_pyridyl) -cyclopropanecarboxamide; v-butyl -8-(1,1-Dimethylethyl) -1-oxaspiro [4.5] decane-3-amine; sodium tetrathiocarbonate; and copper salts and preparations such as Bordeaux; hydroxide Copper; copper naphthalate; copper oxychloride; thiocopperic acid; copper frafrab (cufraneb); copper oxide; mancopper; ο X ine copper. Bactericides: bronopol, dichlorophen, nitrrapyrin, dimethyidithiocarbamate, kasugamy cin, acin Isothilinone, furfuric acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. Insecticides / Acaricides / Nematicides: -35- 200530182 (31) Abamectin, ABG-9008, acephate, acequinocyl, acetamiprid ), Acetoprole, acrinathrin, AKD-1 022, AKD-3 05 9, AKD-3 0 8 8, alanycarb, aldicarb, alumcarb aldoxycarb), Allethrin, α-cypermethrin (alphamethrin), amidoflumet, am i η oc ar b (Amitraz), avermectin, AZ-60541, azadirachtin, azamethiphos, azonphos-methyl, ortholin-ethyl (azocyclotin), Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis > Bacillus thuringiensis EC-2 3 4 8, Bacillus thuringiensis GC-GC- 91. Bacillus thuringiensis NCTC-11821, Bacu loviruses, Beauveria bassiana, Beauveria tenella, ben clothiaz, bendiocarb, benfuracarb, bensultap, and citrate (benzoximate), beta-cyfluthrin, beta-cyperthrin, bifenazate, bifenthrin, binapacryl, bioallethrin ), BioaUethrin-S-pentyl-isomer-36- 200530182 (32) compounds, bi oetha η 〇methri η, bioperm ethrin, bireminin (Bioresmethrin), bistrifluron, BPMC, brofenprox, bromopros (br 〇m 〇ph 〇s) -ethyl, bromopropylate, bromfenvinfos (-methyl) , BTG-504, BTG-505, bufencarb, bufofezin, butathi ofo s, butocarboxim, butoxycarboxim, butyl carboximide (Butylpyridaben), cadusafos, carvenox camphechlor), carbaryl, carbofuran, carbophenothion, butyl carbosulfan, cart ap, CGA-50439, methylomethionat ), Chlordane, Chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, cloflon ( chlorfluazuron), chloromephos, chlorobenzilate, chloropicrin, chlorproxyfen, chlorpyrifos-methyl, taopyzon (-ethyl), kopenin chlo vaporthrin), chromafenozide, cis-cypermethrin, res m ethrin, cis-permethrin, clocythrin , Cloethocarb, clofentezine, clothianidin, clonobin-37- 200530182 (33) (clothiazoben), codie m one, cobeck escape (coumaphos), Shi Lisong (cy anofenphos), cyanophos, cyc 1 oprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cyhexatin permethrin), cyphenothrin (1R-trans-isomer), cyromazine, DDT, deltamethrin, demeton-S-methyl, Demeton-S-methylsulphone, difenthiuron, dialifos, diazinon, dichlofenthion, dichlorvos, big worm South (dicofol), dicrotophos, dicyclanil, diflubenzuron, dimethoate (dinobuton) (dinotefuran (disulfoton ', dimethylvinphos), large Detachment, dinocap, dinotafura, diofenolan, dithiopine, docasa-nano, dofenapyn, DOWCO-43 9, Eflusilanate, eniamectin, influenza Ting-benzoate, empenthrin (1R-isomer), endosulfan, Entomopthora spp., Epin, EPN, esfenvalerate, azafen ( endosulfan), ethiprole, ethion, 38-200530182 (34) (ethoprophos), etofenprox, etoxazole, etrimfos ), Famph ur, fenamiphos, fenazaquin, fenbutatin oxide -M-, fenfluthrin, fenitrothion, butyl Feminine 1¾ (fenobucarb), fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin -μ- , Fenpyroximate, fensulfothion, fenthion, fentrifanil, fenvalerate, fipr ο ni 1 (Flonica mid), fluacrypyrim 'fluorine, fluazuron, flubenzimine, flubrocythrinat e' flucycloxuron ', flucythrinate Flufenerim, flufenoxuron, flufenprox, flumethrin, flupyrazofos-flutenzin (flufenzine) ' j fluvalinate, fonofos, formetanate, for moth ion, fosmethilan, fosthiazate, fubfenprox (fubfenprox) ( Fluproxyfen), furathi 〇ca 1 · b), γ-cylonin (cyha) othr in, r-HCH, Gossler-39- 200530182 (35) (gossyplure), Grand1ure, granulosis virus, halfenprox, halofenozide, HC Η, HCN-801, heptenophos, hexafluron hexaflumuron, hexythiazox, hydramethyinone, hydroprene, IKA-2002, imidacloprid, imiprothrin, indoxacarb, afax Pine (iodofenphos), iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion, ivermectin, Jiabolu (Japonilure), kadethrin, kernpolyederviren, kinoprene, lambda-cyhalothrin, lindane, lufenuron, marathon ( malathion), mecarbarn, mesulfenfos, polyethylene glycol, metam-sodium, metharifos, methamidophos, and aspergillus niger (Metharhizium anisopliae), Metharhizium flavo viri de, methathi ο η, methiocarb, methomy, methoprene, methorene -40- 200530182 (36) (methoxychlor), methoxyfenozide, metofluthrin, met ο 1 carb, metoxadiazone, mevinphos, Milbemectin, niilbemycin, MKI-245, MON-45700, monocrotophos, moxidectin, MTI-800, naled, NC- 104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine, nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, novaluron, noviflumuron, OK-5101, OK-5 20 1, OK-960 1, OK-9602, OK-9701, OK-9802 Omethoate, oxamyl, oxy demeton methyl, Paeci 1 omycesfumosoroseus, Parason methyl, Parason (-ethyl), 100 Permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (1R-trans isomer), Phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, piperidine Oxides, pirimicarb, pirimiphos-methyl, pirimiph 〇s-ethy 1, potassium oleate, prallethrin, profenofos, cloth Funing-41-200530182 (37) profluthrin), promecarb, propaphos, propargite, propetamphos, 'propoxur, prothiofos,' (Prothoate), general --- M- two distribution special protrifenbute) 'piemetrozine', pyraclofos), 歹! J extinguishing (py resmethrin), pyrethrum master m py r ethrum), bi Pyridaben, Bi, y da pyralyl, pyridaphenthion, pyridathion, pyrimidifen-belipfen

(pyriproxyfen), quinalphos, 歹 ij resmethrin, RH-5 8 4 9, ribavirin, RU- 1 245 7, RU- 1 5 5 2 5, S- 421, S- 1 8 3 3, salithion, sebufos, SI- 0 009, silafluofen, sinoflux

(spinosad), spirodiclofen, spiromesifen, sulfluramid, sulfotep, sulprofos, SZI-121, τ-forhuali (flu valin ate), tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, special Temivinphos, terbam, terbufos, tetrachlorvinphos, de-mite-42- 200530182 (38) (tetradifon), tetramethrin, tetramethrin 1 R- .isomers), tetras υ 1, δ • cypermethrin, thiacloprid, thiameth ο X am, thiapronil, Thi atripho s thiocycl am thyd ro gen 0 X al at e, thiodicarb, thiofanox thiofanox thi omet on (thiosultap)-sodium thuringiensin), tolfenpyrad \ tralocythrin, tralomethrin% transfluthrin 'ben: triarathene triazate (tr i azamate) X triazophos, triazuron, trichlophenidi ne, --I: trichlorfon, trie ho derma atr 〇viride, three Trifluniuron, trimethacarb, vamidothion, vaniliprole, verbutin, verticillium lecanil, WL- 1 0 8 477, WL-40027, YI-520 1, YI-5 3 0 1, ΥΙ-5 3 02, XMC, xylylcarb,: AZ-3274, zeta-cypermethrin, norazon ( zolaprofos), ZXI-8 90 1, compound 3-tolyl propylaminocarbamate (Tsumacide Z), -43- 200530182 (39) compound 3- (5-chloro-3-pyridine) ) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3 · 2. .1] -octane-3- Nitrile (CaS registration number 1 8 5 9 8 2-80-3) and the corresponding 3 -introisomer (CAS registration number 185984-60-5) (refer to V / O-96 / 37494, WO- 98/25923), and preparations containing plant extracts, nematodes, fungi or viruses with insecticidal activity. The aforementioned ingredients used in the composition are known active compounds, many of which are described in C.D.S. Tomlin (eds.), Pesticide Handbook, 12th edition, British Crop Protection Conference, Farnham 2000. The content of the active compound in the use form prepared from a commercially available formulation can range from 0.00000 to 015% by weight of the active compound, preferably between 0. 0 0 0 0 0 1 and 1% by weight . It is effective to apply it in a conventional manner in a form suitable for use. Therefore, the present invention also provides the use of a compound of formula (I) 'or a salt thereof for controlling animal pests, preferably harmful arthropods such as insects and mites and worms such as nematodes. Furthermore, the present invention provides a method for controlling harmful insects, mites and / or worms, which comprises applying an effective amount of a compound of the formula (I) 'or a salt thereof to a pest or a desired action site. The active compounds according to the invention are also suitable for controlling endoparasites and ectoparasites in the field of veterinary medicine and / or animal husbandry. The active compounds according to the invention are applied here in a conventional manner, such as by oral administration in the form of, for example, lozenges, capsules, drinks or granules, by skin administration by, for example, immersion, spraying, pouring and spotting , Sprinkle with powder and non-44-200530182 (40) for enteral administration by injection, for example. Therefore, the present invention also provides a compound of formula (I), or a salt thereof, for use in the preparation of human 4 drugs and / or medical medicine (preferably a veterinary medicine, especially for external- and / or internal parasites) Use for control. Therefore, the compound of formula (I) according to the present invention can also be advantageously used in the livestock breeding industry (for example, cattle, sheep, pigs, and poultry, such as chickens, geese, and the like). In a preferred embodiment of the present invention, the compound, if appropriate, is administered orally to an animal in an appropriate formulation, and if appropriate, orally administered to the animal with water or feed. Since it is effectively excreted in feces, this method can very easily prevent the development of insects in animal feces. The dosages and formulations suitable for each example depend in particular on the species and stage of development of the production animal and the risk of infestation 'and can be easily determined and determined by conventional methods1. For example, the compound may be used in cattle at a dose of 0.01 to 1 mg / kg body weight. In addition to the application method described above, according to the formula (I) of the present invention, the active compound also has an excellent systemic effect. Therefore, when the active compound is applied to the immediate surroundings of the plant in liquid or solid form (for example, particles in soil application, applied in rice fields), the active compound can also pass through the underground and aboveground parts of the plant (roots, stems, leaves ) Into plants. Furthermore, the active compounds according to the present invention are particularly useful for the treatment of nutrient and reproductive plant proliferative substances, such as seeds, cuttings, cuttings and other growth and reproduction crops, such as hoe plants, vegetables, cotton, rice, sugar beet and other crops and ornamental plants. And bulbs, shoots and tubers of ornamental plants. Can be treated before sowing or before planting (eg by special seed coating techniques, liquid-45- 200530182 (41) soaking or seed box treatment in bulk or solid form), during or after sowing or planting Treated with special application technology (eg furrow treatment). Depending on the mode of application, the amount of active compound applied can vary within a relatively wide range. Generally, the application rate is between 10 g and 10 kg per hectare of soil surface. Compounds of formula (I) 'can also be used to control animal pests of crops of known genetically engineered plants or genetically engineered plants that are still under development. In general, transgenic plants are particularly advantageous with particularly advantageous properties, such as resistance to specific crop protection agents, pathogens against plant diseases or plant diseases, such as in particular insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate to, for example, the quantity, quality, storability, composition and special ingredients of the harvest. Therefore, transgenic plants with increased starch content or modified starch quality or such harvests with different fatty acid compositions are known. Important economically transgenic crops used in useful and ornamental plants are preferably, for example, cereals such as wheat, barley, rye, oats, coriander, rice, cassava and corn or sugar beets, cotton, soybeans, oilseed rape, potatoes, Crops of tomatoes, peas and other types of vegetables. When used in transgenic crops, especially those with insect resistance, in addition to the effects observed on other crops against harmful pests to be observed, effects are often observed, which are useful for the application of the transplantation in question Genetic crops are specific, such as changes in controllable pests or a particularly broad range, or changes in application rates that can be applied. The present invention therefore also relates to the use of compounds of formula (I) 'for controlling the transgenic genes as pests of -46-200530182 (42). The use of the compounds of the fundamental invention includes any application other than direct application to pests, wherein the compound of formula (I) 'acts on pests. Such indirect applications can be, for example, the use of compounds which are decomposed or degraded into compounds of formula (I) in soil, plants or pests, for example. In addition to their lethal effect on pests, the compounds of formula (I) 'also have a significant waterproof effect. The waterproofing agent for the purpose of the present invention is a substance or a mixture of substances, which has the effect of preventing or repelling other living organisms, especially harmful pests and public pests. The term also includes effects such as antifeedant effects, where the intake of feed is disturbed or avoided (antifeedant effects), spawning inhibition, or effects on the development of insect populations. The present invention therefore also provides the use of a compound of formula (I) 'or a salt thereof to achieve the above-mentioned effect, especially in the case of the pests described in the biological examples. The present invention also provides a method for repelling, or preventing, a pest in which one or more compounds of formula (I) 'or a salt thereof is applied to the location of the pest to be repelled or prevented. In the case of plants, application can mean, for example, the treatment of plants, or also the treatment of seeds. Regarding the effect on the insect mouth, it is interesting to note that the effect can also be continuously observed during the development of the insect mouth, in which a total may occur. In this case, the individual effects themselves have significantly less than 100% efficacy, but still achieve a total of 100% efficacy at the end. Furthermore, the compound of the formula (I) or a salt thereof is characterized by the fact that if the above-mentioned effects are to be developed, the composition is usually applied earlier than in the case of direct control. The effect often lasts for a long period of time, so an action period of more than 2 months is achieved. Observe these effects in insects, spiders and other such pests. The special document is the content of German patent application 103 46 245.7. Its priority is claimed in this case and includes an abstract; it is incorporated in this description by reference. [Embodiment] The present invention will be described in detail by way of example without being limited thereby. Example A Chemical example General method One equivalent of amidine, one equivalent of sodium methoxide and one equivalent of a compound of formula (III) were heated in NMP at 60-70 ° C and 100 mbar for 1-3 hours. Example 1 Preparation of Allyl Ethoxy-N-Ethylaminocarbamate 1.0 mole of dichloromethane was introduced into 600 ml of water. At 15 to 20 ° C, a solution of 1.1 mol NaOH in 45% by weight was added dropwise until a pH of 7.5 was reached. Then, at a temperature of 15-25 ° C and a pH of 7-8, allyl chloroformate and 1.0 mol NaOH were added dropwise at the same time. After the addition was complete, p Η was adjusted to 1] and then 3.0 Mo-48- 200530182 (44) ear diethyl sulfate was added over a 3 hour period, and the pH was maintained at 11 by adding NaOH. After the addition was complete, the mixture was stirred at 30-3 5 ° C and a pH of 11 for 2 hours. The organic phase was separated, the aqueous phase was extracted three times with ethyl acetate, and the combined organic phase was dried and then concentrated. The theoretical yield is 93%, gray oil. Preparation of the compounds of Tables 1 and 2: 10% by weight of hydrochloric acid was slowly added dropwise until a pH of 5 was reached. The reaction mixture was diluted with water, and the product was extracted with ethyl acetate. The organic phase was washed with H20 and dried, and the solvent was removed in vacuo. a) Preparation of compounds of Table 3: The resulting precipitate was filtered and washed with methanol. The following is obtained by the general method =

(45) 200530182 Table 1: Compounds of formula (Iaa)

N

〇 II 3 4 (Iaa)

NC—NR3R4 I Η Compound R6 R4 A-1 ch3ch = chch2 ch3 A-2 CH2 = C (CH3) CH2 ch3 A-3 CH2 = CH (CH3) CH ch3 A-4 ch2 = chch2ch2 ch3 A-5 CH3CH = C (CH3) CH2 ch3 A-6 CH (CH3) HC = CHCH3 ch3 A-7 C (CH3) 2HC = CH2 ch3 A-8 CH2HC = C (CH3) 2 ch3 A-9 CH3CH = CHCH2CH2 ch3 A-10 CH2 = CHCH2CH2CH2 ch3 A-11 chc = cch2 ch3 A-12 ch3c = cch2 ch3 A-13 HC = CCH (CH3) ch3 A-14 CH3C = CCH (CH3) ch3 A-15 ring-C3H5 ch3 A-16 ring-C5H9 ch3 A-17 ring-C6H11 ch3 A-18 (ring-c3h5) ch2 ch3 A-19 (ring-c5h9) ch2 ch3 A-20 (ring ch3 A-21 PhCH2 ch3 A-22 PhCH (CH3) ch3 A-23 PhC (CH3) 2 ch3 -50- (46) 200530182 Compound R4 A-24 PhCH2CH2 ch3 A-25 (2-F-Ph) CH2 ch3 A-26 (3-F-Ph) CH2 ch3 A-27 (4-F -Ph) CH2 ch3 A-28 (2-CI-Ph) CH2 ch3 A-29 (3-CI-Ph) CH2 ch3 A-30 (4-CI-Ph) CH2 ch3 A-31 (2-CF3-Ph ) CH2 ch3 A-32 (3-CF3-Ph) CH2 ch3 A-33 (4-CF3-Ph) CH2 ch3 A-34 (2-CH3〇-Ph) CH2 ch3 A-35 (3-CH3〇-Ph ) CH2 ch3 A-36 (4-CH3〇-Ph) CH2 ch3 A-37 ch3o ch3 A-38 CH3CH2〇ch3 A-39 η-〇3Η7〇ch3 A-40 iso-C3H7O ch3 A-41 ch2 = chch2o ch3 A-42 CH2 = C (CH3) CH2〇ch3 A-43 CH2 = CHCH (CH3) 〇ch3 A-44 CH2 = CHCH (CH3) 〇ch3 A-45 CH2 = CHC (CH3) 2〇ch3 A-46 ch3ch = chch2o ch3 A-47 hc ^ cch2o ch3 A- 48 CH3OCCH20 ch3 A-49 HC ^ CCH (CH3) 〇ch3 A-50 CH3〇2CCH (CH3) 〇ch3 A-51 CH3〇2〇C (CH3) 2〇ch3 A-52 CH302CCH20 ch3 A-53 PhCH20 ch3 A -54 Ph〇 (ch3 A-55 Ph 丨 ch3 A-56 2-F-Ph (ch3 -51-(47) 200530182 compound R4 A-57 3-F-Ph ch3 A-58 4-F-Ph ch3 A -59 2-CI-Ph ch3 A-60 3-CI-Ph ch3 A-61 4-CI-Ph ch3 A-62 2-Br-Ph ch3 A-63 3-Br-Ph ch3 A-64 4-Br -Ph ch3 A-65 2-l-Ph ch3 A-66 3 small Ph ch3 A-67 4 small Ph ch3 A-68 2-CF3-Ph ch3 A-69 3-CF3-Ph ch3 A-70 4-CF3 -Ph ch3 A-71 2-CH3-Ph ch3 A-72 3-CH3-Ph ch3 A-73 4-CH3-Ph ch3 A-74 2-CH3〇-Ph ch3 A-75 3-CH3〇-Ph ch3 A-76 4-CH3〇-Ph ch3 A-77 2-N〇2-Ph ch3 A-78 3-N〇2-Ph ch3 A-79 4-N02-Ph ch3 A-80 2-CN-Ph ch3 A-81 3-CN-Ph ch3 A-82 4-CN-Ph ch3 A-83 2-C02Me-Ph ch3 A-84 3-C02Me-Ph ch3 A-85 4-C〇2Me-Ph ch3 A-86 2-CF3OPh ch3 A-87 3-CF30-Ph ch3 A-88 4-CF30-Ph ch3 A-89 4-CF3CH2〇-Ph ch3 -52- (48) 2 00530182 Compound R4 A-90 4- (4-CI-PhO) -Ph ch3 A-91 4- (4-CF3-PhO) -Ph ch3 A-92 2,3-ZK > Ph ch3 A-93 2,4 -Di-Cl-Ph ch3 A-94 2,5-Di-Cl-Ph ch3 A-95 2,6-Di-Cl-Ph ch3 A-96 3,4-Z: CI-Ph ch3 A-97 3,5- Z: CI-Ph ch3 A-98 2-pyridyl ch3 A-99 3-pyridyl ch3 A-100 4-pyridyl ch3 A-101 2-pyrimidyl ch3 A-102 1-pyrrolyl ch3 A- 103 1-pyrazolyl ch3 A-104 3-pyrazolyl ch3 A-105 1,2,4-triazolyl ch3 A-106 1,2,4-triazol-3-yl ch3 A-107 2 -Alkyl ch3 A-108 3-furyl ch3 A-109 2-thienyl ch3 A-110 3-thienyl ch3 A-111 2-thiazolyl ch3 A-112 1,3,4-thiadiazole-2 -Base ch3 A-113 3-Isoxazolyl ch3 A-114 cf3ch2 ch3 A-115 CICH2CH2 ch3 A-116 CICH2CH2CH2 ch3 A-117 CH30CH2CH2 ch3 A-118 CH3CH20CH2CH2 ch3 A-119 CH30CH2CH2CH2 ch3 A-120 C2H2 121 n-C4H9〇CH2CH2CH2 ch3 A-122 (CH3〇) 2〇HCH2 ch3 -53- (49) 200530182 Compound R4 A-123 (CH3〇) 2C = CH2 ch3 A-124 (CH3〇2) C = CH ( CH3) ch3 A-125 CH3〇2〇C (CH3) 2 ch3 A-126 ncch2 ch3 A-127 nc (ch3) (iso-c3h7) c ch3 A-128 ( 1-pyrrolidinyl) CH2CH2 C2H5 A-129 ch2 = chch2 C2H5 A-130 chc = ch2 C2H5 A-131 ch3c = cch2 C2H5 A-132 (ring-C3H5) CH2 C2H5 A-133 PhCH2 C2H5 A-134 PhCH2CH2 C2H5 A -135 (2-CI-Ph) CH2 C2H5 A-136 (3-C | .Ph) CH2 C2H5 A-137 (4-CI-Ph) CH2 C2H5 A-138 (2-CF3-Ph) CH2 C2H5 A- 139 (3-CF3-Ph) CH2 C2H5 A-140 (4-CF3-Ph) CH2 C2H5 A-141 (2-CH3〇-Ph) CH2 C2H5 A-142 (3-CH3〇-Ph) CH2 C2H5 A- 143 (4-CH3〇-Ph) CH2 C2H5 A-144 CH3〇C2H5 A-145 CH3CH2O C2H5 A-146 1 > 〇3 latch 7〇C2H5 A-147 iso-c3h7o C2H5 A-148 ch2 = chch2o C2H5 A-149 hc ^ cch2o C2H5 A-150 PhCH2〇C2H5 A-151 Ph〇C2H5 A-152 Ph C2H5 A-153 2-CI-Ph C2H5 A-154 3-CI-Ph 丨 C2H5 A-155 4-CI-Ph 丨 C2H5 -54- (50) 200530182 Compound R4 A-156 2-CF3-Ph C2H5 A-157 3-CF3-Ph C2H5 A-158 4-CF3-Ph C2H5 A-159 2-CH30-Ph C2H5 A-160 3_CH3. -Ph C2H5 A-161 4-CH3〇-Ph C2H5 A-162 4-CF30-Ph C2H5 A-163 4-CF3CH2〇-Ph C2H5 A-164 4- (4-CI-PhO) -Ph C2H5 A-165 4- (4-CF3-PhO) -Ph C2H5 A-166 2,3-di-Cl-Ph C2H5 A-167 1-pyrrolyl C2H5 A-168 1-pyrazolyl C2H5 A-169 1,2,4-triazol-1-yl C2H5 A-170 2-thiazolyl C2H5 A-171 1,3,4-thiazol-2-yl C2H5 A-172 CH3〇2CCH2 C2H5 A-173 CH3 〇2CCH (CH3) C2H5 A-174 NCCH2 n-C3H7 A-175 ch2 = chch2 iso-C3H7 A-176 hc = cch2 iso_C3H7 A-177 CH30CCH2 iso-C3H7 A-178 (cyclo-C3H5) CH2 iso-c3h7 A-179 PhCH2 iso-C3H7 A-180 PhCH2CH2 iso-c3h7 A-181 (2-CI-Ph) CH2 iso-C3H7 A-182 (3-CI-Ph) CH2 iso-c3h7 A-183 (4-CI- Ph) CH2 iso-c3h7 A-184 (2-CF3-Ph) CH2 iso-C3H7 A-185 (3-CF3-Ph) CH2 iso-c3h7 A-186 (4-CF3-Ph) CH2 iso-C3H7 A- 187 (2-CH3〇-Ph) CH2 iso-c3h7 A-188 (3-CH3〇-Ph) CH2 iso-c3h7 -55- (51) 200530182 compound R4 A-189 (4-CH3〇-Ph) CH2 iso -C3H7 A-190 ch3o iso-C3H7 A-191 CH3CH2〇iso-c3h7 A-192 η-〇3Η7〇iso-C3H7 A-193 ISO-C3H7O iso-C3H7 A-194 ch2 = chch2o iso-C3H7 A-195 hc ^ cch2o iso-c3h7 A-196 PhCH2〇iso-C3H7 A-197 Ph〇iso-C3H7 A-198 Ph iso-C3H7 A-199 2-CI-Ph iso-C3H7 A-200 3-CI-Ph iso-C3H7 A-201 4-CI-Ph iso-C3H7 A-202 2-CF3-Ph iso-c3h7 A-203 3-CF3-Ph iso-C3H7 A-204 4-CF3-Ph iso-C3H7 A-205 2-CH 3〇-Ph iso-c3h7 A-206 3_CH3〇Ph iso-C3H7 A-207 4-CH3〇-Ph iso-c3h7 A-208 4-CF3〇-Ph iso-c3h7 A-209 4-CF3CH2〇-Ph iso -c3h7 A-210 4- (4-CI-PhO) -Ph iso-c3h7 A-211 4- (4-CF3-PhO) -Ph iso-c3h7 A-212 2,3-di-Cl-Ph iso_. A-213 1-pyrrolidinyl-C3H7 A-214 1-pyrazolyliso-C3H7 A-215 1,2,4-triazolyl-C3H7 A-216 2-thiazolyl-C3H7 A -217 1,3,4-thiadiazol-2-yliso-C3H7 A-218 cf3ch2 iso-c3h7 A-219 CICH2CH2 iso-C3H7 A-220 CICH2CH2CH2 iso-C3H7 A-221 CH3OCH2CH2 iso-C3H7 -56- ( 52) 200530182 Compound R0 R4 A-222 CH3CH2OCH2CH2 iso-C3H7 A-223 CH3OCH2CH2CH2 iso-C3H7 A-224 C2H5OCH2CH2CH2 iso-c3h7 A-225 n-C4H9 0CH2CH2CH2 iso-c3h7 A-226 (2) 227 CH3O2CCH2 iso-C3H7 A-228 CH3〇2CCH (CH3) iso-C3H7 A-229 ncch2 iso-c3h7 A-230 NC (CH3) (iso-C3H7) tertiary-C4H9 A-231 ch2 = chch2 tertiary-c4h9 A-232 CHCCH2 Level III-c4h9 A-233 CH3CCCH2 Level III-c4h9 A-234 (cyclo-C3H5) CH2 Level III-C4H9 A-235 PhCH2 Level III-C4H9 A-236 PhCH2CH2 Level III-c4h9 A-237 (2 -CI-Ph) CH2 Level 3 -c4h9 A-238 (3-α-ΡΙι) αΗ2 Level 3 -c4h9 A-239 (4-CI-Ph) CH2 Level 3, C4H9 A-240 (2-CF3-Ph) CH2 Level 3-c4H9 A-241 (3-CF3-Ph) CH2 Level 3-c4h9 A-242 (4-CF3-Ph) CH2 Level 3-c4h9 A-243 (2-CH3〇-Ph) CH2 Level 3- c4h9 A-244 (3-CH3〇-P h) CH2 tertiary-C4H9 A-245 (4-CH3O-Ph) CH2 tertiary-. 4 rings A-246 CH3〇-C4H9 A-247 CH3CH2O third stage-c4H9 A-248 η-〇3Η7〇 third stage-C4H9 A-249 ISO-C3H7O third stage-C4H9 A-250 ch2 = chch2o third stage-c4h9 A -251 hc ^ cch2o Tertiary-C4H9 A-252 PhCH2〇 Tertiary-c4h9 A-253 Ph〇 Tertiary-C4H9 A-254 Ph Tertiary-c4h9 -57- (53) 200530182 Compound R4 A-255 2-CI -Ph Level 3 -C4H9 A-256 3-CI-Ph Level 3 -C4H9 A-257 4-CI-Ph Level 3 (# 9 A-258 2-CF3-Ph Level 3 -C4Hg A-259 3-CF3- Ph Class III-C4H9 A-260 4-CF3-Ph Class III-c4h9 A-261 2-CH3〇-Ph Class III-C4H9 A-262 3-CH3〇-Ph Class III-C4H9 A-263 4-CH3〇 -Ph Level III-c4h9 A-264 4-CF3〇-Ph Level III-c4h9 A-265 4-CF3CH2〇-Ph Level III, C4H9 A-266 4- (4-CI-PhO) -Ph Level III-C4H9 A-267 4- (4-CF3-PhO) -Ph tertiary-c4h9 A-268 2,3-di-Cl-Ph tertiary-C4H9 A-269 1-pyrrolyl tertiary, C4H9 A-270 1-pyridine Oxazolyl tertiary-C4H9 A-271 1,2,4-triazol-1-yl tertiary-C4H9 A · 272 2-thiazolyl tertiary-c4h9 A-273 1,3,4-thiadiazole-2 -Base third stage-C4H9 A-274 CH3〇2CCH2 Third stage 9 A-275 CH3〇2CCH (CH3) Third stage-C4H9 A-276 ncch2 Third stage-c4h9 A-277 nc (ch3) (iso-c3h7) cch2 = chch2 A-278 ch2 = chch2 ch2 = chch2 A-279 hc = cch2 ch2 = chch2 A-280 CH3CCCH2 ch2 = chch2 A-281 (ring-c3h5) ch2 ch2 = chch2 A-282 PhCH2 ch2 = chch2 A-283 PhCH2CH2 ch2 = chch2 A-284 (2-CI-Ph) CH2 ch2 = chch2 A-285 (3-CI-Ph) CH2 ch2 = chch2 A-286 (4-CI-Ph) CH2 ch2 = chch2 A-287 ( 2-CF3-Ph) CH2 ch2 = chch2 -58- (54) 200530182 Compound R4 A-288 (3-CF3-Ph) CH2 ch2 = chch2 A-289 (4-CF3-Ph) CH2 ch2 = chch2 A-290 (2-CH3〇-Ph) CH2 ch2 = chch2 A-291 (3-CH3〇-Ph) CH2 ch2 = chch2 A-292 (4-CH3〇-Ph) CH2 ch2 = chch2 A-293 ch3o ch2 = chch2 A -294 CH3CH2〇ch2 = chch2 A-295 Π-〇3Η7〇ch2 = chch2 A-296 iso-c3h7o ch2 = chch2 A-297 ch2 = chch2o ch2 = chch2 A-298 chcch2o ch2 = chch2 A-299 PhCH2〇ch2 = chch2 A-300 PhO ch2 = chch2 A-301 Ph ch2 = chch2 A-302 2-CI-Ph ch2 = chch2 A-303 3-CI-Ph ch2 = chch2 A-304 4-CI-Ph ch2 = chch2 A- 305 2-CF3-Ph ch2 = chch2 A-306 3-CF3-Ph ch2 = chch2 A-307 4-CF3-Ph ch2 = chch2 A-308 2-CH30-Ph ch2 = chch2 A-309 3-CH30-Ph ch2 = chch2 A-310 4-CH3〇-Ph ch2 = chch2 A-311 4-CF3〇-Ph ch2 = chch2 A-312 4-CF3CH2〇-Ph ch2 = chch2 A-313 4- (4-CI-PhO) -Ph ch2 = chch2 A-314 4- (4-CF3-PhO) -Ph ch2 = chch2 A-315 2,3-di-Cl-Ph ch2 = chch2 A-316 1-pyrrolyl ch2 = chch2 A-317 1-pyrazolyl ch2 = chch2 A-318 1,2,4-triazole small group ch2 = chch2 A-319 2-thiazolyl ch2 = chch2 A- 320 1,3,4-thiadiazole. 2-yl ch2 = chch2 -59- (55) 200530182 compound FT3 R4 A-321 CF3CH2 ch2 = chch2 A-322 CICH2CH2 ch2 = chch2 A-323 CICH2CH2CH2 ch2 = chch2 A- 324 CH3OCH2CH2 ch2 = chch2 A-325 CH3CH2OCH2CH2 ch2 = chch2 A-326 CH3OCH2CH2CH2 ch2 = chch2 A-327 C2H5OCH2CH2CH2 ch2 = chch2 A-328 n-C4H9〇CH2CH2CH2 ch2 = ch2 = ch2 = ch2 330 CH3O2CCH2 ch2 = chch2 A-331 CH3〇2CCH (CH3) ch2 = chch2 A-332 ncch2 ch2 = chch2 A-333 nc (ch3) (iso-c3h7) c PhCH2 A-334 ch2 = chch2 PhCH2 A-335 hc ^ cch2 PhCH2 A-336 ch3c = cch2 PhCH2 A-337 (ring-c3h5) ch2 PhCH2 A-338 PhCH2 PhCH2 A-339 PhCH2CH2 PhCH2 A-340 (2-CI-Ph) CH2 PhCH2 A-341 (3-CI-Ph ) CH2 PhCH2 A-342 (4-CI-Ph) CH2 PhCH2 A-343 (2-CF3-Ph) CH2 PhCH2 A-344 (3-CF3-Ph) CH2 PhCH2 A-345 (4-CF3-Ph) CH2 PhCH2 A-346 (2-CH3〇 -Ph) CH2 PhCH2 A-347 (3-CH3〇-Ph) CH2 PhCH2 A-348 (4-CH3〇-Ph) CH2 PhCH2 A-349 CH3〇PhCH2 A-350 CH3CH2O PhCH2 A-351 η-〇3Η7〇 PhCH2 A-352 iso-c3h7o PhCH2 A-353 ch2 = chch2o PhCH2 -60- (56) 200530182 Compound R0 R4 A-354 CHCCH2〇PhCH2 A-355 PhCH2〇PhCH2 A-356 Ph〇PhCH2 A-357 Ph PhCH2 A- 358 2-CI-Ph PhCH2 A-359 3-CI-Ph PhCH2 A-360 4-CI-Ph PhCH2 A-361 2-CF3-Ph PhCH2 A-362 3-CF3-Ph PhCH2 A-363 4-CF3- Ph PhCH2 A-364 2-CH3〇-Ph PhCH2 A-365 3-CH3〇-Ph PhCH2 A-366 4-CH3〇Ph PhCH2 A-367 4-CF3〇-Ph PhCH2 A-368 4-CF3CH2〇-Ph PhCH2 A-369 4- (4-ΟΙ-ΡΜΟ) -Price PhCH2 A-370 4- (4-CF3-PhO) -Ph PhCH2 A-371 2,3-diCl-Ph PhCH2 A-372 1-pyrrolyl PhCH2 A-373 1-pyrazolyl PhCH2 A-374 1,2,4-trimile-1-yl PhCH2 A-375 2-thiazolyl PhCH2 A-376 1,3,4-thiadiazol-2-yl PhCH2 A-377 cf3ch2 PhCH2 A-378 CICH2CH2 PhCH2 A-379 CICH2CH2CH2 PhCH2 A-380 CH30CH2CH2 PhCH2 A-381 CH3CH20CH2CH2 PhCH2 A-382 CH30CH2CH2CH2 PhCH2 A-384 C2H50CH2CH2CH2CHCH2H-384 A-385 (CH30) 2CHCH2 PhCH2 A-386 CH (CH3) CH2CH2CH2CH2 -61-(57) 200530182 Compound R4 A-387 CH2CHBrCH2CH2 A-388 CH2CH (OH) CH2〇H2 A-389 CH2〇H = CHCH2 A-390 Ph Ph A-391 CH3SO2OCH2CH2CH2CH2 H A-392 CH2CH2CH2CH2CH2 A-393 CH2CH2OCH2CH2 A-394 CH2CH2SCH2CH2 A-395 CH2CH2NHCH2CH2 A-396 CH2〇H2N (CH3) CH2CH2 A-397 N = CHCH2 CH2 -30-62 Ibb) Compound R11

〇 〇 II II u c—N-c—nr3r4 (Ibb)

I Η 11 R = CHF2 (compounds B1-B 397) or CF2CI (compounds C1-C 397) compound R4 B-1 / C-1 ch3ch = chch2 ch3 B-1 / C-2 CH2 = C (CH3) CH2 ch3 B-1 / 03 CH2 = CH (CH3) CH ch3 B ^ 1 / C-4 ch2 = chch2ch2 ch3 B-1 / C-5 CH3CH = C (CH3) CH2 ch3 B-1 / C-6 CH (CH3) HC = CHCH3 ch3 B-1 / 07 C (CH3) 2HC = CH2 ch3 B-1 / 08 CH2HC = C (CH3) 2 ch3 B-1 / C-9 CH3CH = CHCH2CH2 ch3 B-1 / C- 10 CH2 = CHCH2CH2CH2 ch3 B-1 / C- 11 CHOCCH2 ch3 B-1 / C- 12 CH30CCH2 ch3 B-1 / C- 13 HC = CCH (CH3) ch3 B-1 / C- 14 ch3occh (ch3) ch3 B-1 / C- 15 ring-C3H5 ch3 B-1 / C- 16 ring-c5h9 ch3 B-1 / C- 17 ring-C6H11 ch3 B-1 / C- 18 (ring-c3h5) ch2 ch3 EM / C- 19 (ring -C5H9) CH2 ch3 B-1 / C- 20 (ring ch3 B-1 / C- 21 PhCH2 ch3-63- (59) 200530182 compound R4 B-1 / C- 22 PhCH (CH3) ch3 B-1 / C -23 PhC (CH3) 2 ch3 B-1 / C- 24 PhCH2CH2 ch3 B-1 / C- 25 (2-F-Ph) CH2 ch3 B-1 / C- 26 (3-F-Ph) CH2 ch3 B -1 / C- 27 (4-F-Ph) CH2 ch3 B-1 / C- 28 (2-CI-Ph) CH2 ch3 B-1 / C- 29 (3-CI-Ph) CH2 ch3 B-1 / C- 30 (4-CI-Ph) CH2 ch3 B-1 / C- 31 (2-CF3-Ph) CH2 ch3 B-1 / C- 32 (3-CF3 -Ph) CH2 ch3 B-1 / C- 33 (4-CF3-Ph) CH2 ch3 B-1 / C- 34 (2-CH3〇-Ph) CH2 ch3 B-1 / C- 35 (3-CH3〇 -Ph) CH2 ch3 B-1 / C- 36 (4-CH3〇-Ph) CH2 ch3 B-1 / C- 37 ch3o ch3 B-1 / C- 38 CH3CH2〇ch3 B-1 / C- 39 IVC3H7O ch3 B-1 / C- 40 iso-c3h7o ch3 B-1 / C- 41 ch2 = chch2o ch3 B-1 / C- 42 CH2 = C (CH3) CH2〇ch3 B-1 / C- 43 CH2 = CHCH (CH3 ) 〇ch3 B-1 / C- 44 CH2 = CHCH (CH3) 〇ch3 B-1 / C- 45 CH2 = CHC (CH3) 2〇ch3 B-1 / C- 46 ch3ch = chch2o ch3 B-1 / C -47 hc = cch2o ch3 B-1 / C- 48 ch3c ^ cch2o ch3 B-1 / C- 49 HC ^ CCH (CH3) 0 ch3 B-1 / C- 50 CH3〇2CCH (CH3) 〇ch3 B-1 / C- 51 CH3〇2CC (CH3) 2〇ch3 B-1 / C- 52 ch3o2cch2o ch3 B-1 / C- 53 PhCH2〇ch3 B-1 / C- 54 PhO ch3 -64- (60) 200530182 Compound R4 B-1 / Ο 55 Ph ch3 Β-1 / C- 56 2-F-Ph ch3 Β-1 / C- 57 3-F-Ph ch3 Β-1 / C- 58 4-F-Ph ch3 Β-1 / C- 59 2-CI-Ph ch3 Β-1 / C- 60 3-CI-Ph ch3 Β-1 / C- 61 4-CI-Ph ch3 Β-1 / C- 62 2-Br-Ph ch3 Β -1 / C- 63 3-Br-Ph ch3 Β-1 / C- 64 4-Br-Ph ch3 Β-1 / C- 65 2-l-Ph ch3 Β-1 / C- 66 3 small Ph ch3 Β-1 / C- 67 4 small Ph ch3 Β-1 / C- 68 2-CF3-Ph ch3 Β-1 / C- 69 3-CF3-Ph ch3 Β-1 / C- 70 4-CF3-Ph ch3 Β-1 / C- 71 2-CH3-Ph ch3 Β-1 / C- 72 3-CH3-Ph ch3 Β-1 / C- 73 4-CH3-Ph ch3 Β-1 / C- 74 2-CH3 〇-Ph ch3 Beta-1 / C- 75 3-CH3 〇-Ph ch3 Beta-1 / C- 76 4-CH30-Ph ch3 Beta-1 / C- 77 2-N02-Ph ch3 Beta-1 / C- 78 3-N02-Ph ch3 Beta-1 / 〇 79 4-N〇2-Ph ch3 Beta-1 / C- 80 2-CN-Ph ch3 Beta-1 / 〇 81 3-CN-Ph ch3 Beta-1 / C- 82 4-CN-Ph ch3 Β-1 / C- 83 2-C02Me-Ph ch3 Β-1 / C- 84 3-C02Me-Ph ch3 Β-1 / C- 85 4-C02Me-Ph ch3 Β- 1 / C- 86 2-CF3〇-Ph ch3 Β-1 / C- 87 3-CF30-Ph ch3 -65- (61) 200530182 Compound R6 R4 B-1 / C- 88 4-CF30-Ph ch3 B- 1 / C- 89 4-CF3CH2〇-Ph ch3 B-1 / C- 90 4- (4-CI-PhO) -Ph ch3 B-1 / C- 91 4- (4-CF3-PhO) -Ph ch3 B-1 / C- 92 2,3-di-Cl-Ph ch3 B-1 / C- 93 2,4-di-Cl-Ph ch3 B-1 / C- 94 2,5-Z: CI-Ph ch3 B -1 / C- 95 2,6-bi-o ch3 B-1 / C- 96 3,4-di-Cl-Ph ch3 B-1 / C- 97 3,5-di-Cl-Ph ch3 B-1 / C- 98 2-pyridyl ch3 B-1 / C- 99 3-pyridyl ch3 B-1 / C- 100 4-pyridyl ch3 B-1 / C- 101 2-pyrimidinyl ch3 B-1 / C- 102 pyrrolyl ch3 B-1 / C- 103 1-pyrazolyl ch3 B-1 / C- 104 3-pyrazolyl ch3 B-1 / C- 105 1,2,4-triazol-1-yl ch3 B-1 / C- 106 1,2,4-triazol-3-yl ch3 B-1 / C- 107 2-furyl ch3 B-1 / C- 108 3 difluorenyl ch3 B-1 / C- 109 2-thienyl ch3 B-1 / C- 110 3-thienyl ch3 B-1 / C -111 2-thiazolyl ch3 B-1 / C- 112 1,3,4-thiazolyl, 2-yl ch3 B-1 / C- 113 3-isoxazolyl ch3 B-1 / C- 114 cf3ch2 ch3 B -1 / C- 115 CICH2CH2 ch3 B-1 / C- 116 CICH2CH2CH2 ch3 B-1 / C- 117 CH30CH2CH2 ch3 B-1 / C- 118 CH3CH20CH2CH2 ch3 B-1 / C- 119 CH30CH2CH2CH2 ch3 B-1 / C- 120 C2H50CH2CH2CH2 'ch3 -66-(62) 200530182 Compound R6 R4 B-1 / C- 121 n-C4H9〇CH2CH2CH2 ch3 122 (CH3〇) 2CHCH2 ch3 123 (CH3〇) 2C = CH2 ch3 124 (CH3〇2) C = CH (CH3) ch3 125 CH3〇2CC (CH3) 2 ch3 126 ncch2 ch3 127 nc (ch3) (iso-c3h7) c ch3 128 (1-pyrrolidinyl) ch2ch2 C2H5 129 ch2 = chch2 C2H5 130 chc = ch2 C2H5 131 ch3c ^ cch2 C2H5 132 (ring-c3h5) ch2 C2H5 133 PhCH2 C2H5 1 34 PhCH2CH2 C2H5 135 (2-CI-Ph) CH2 C2H5 136 (3-CI-Ph) CH2 C2H5 137 (4-CI-Ph) CH2 C2H5 138 (2-CF3-Ph) CH2 C2H5 139 (3-CF3-Ph ) CH2 C2H5 140 (4-CF3-Ph) CH2 C2H5 141 (2-CH3〇-Ph) CH2 C2H5 142 (3-CH30-Ph) CH2 C2H5 143 (4-CH3〇_Ph) CH2 C2H5 144 ch3o C2H5 145 CH3CH2 〇C2H5 146 η-〇3Η7〇C2H5 147 Iso-c3h7o C2H5 148 ch2 = chch2o C2H5 149 hc ^ cch2o C2H5 150 PhCH2〇C2H5 151 Ph〇C2H5 152 Ph C2H5 153 2-CI-Ph C63H5 -2005 R4 B-1 / C- 154 3-CI-Ph C2H5 B-1 / C- 155 4-CI-Ph C2H5 B-1 / C- 156 2-CF3-Ph C2H5 B-1 / C- 157 3-CF3 -Ph C2H5 B-1 / C- 158 4-CF3-Ph C2H5 B-1 / C- 159 2-CH30-Ph C2H5 B-1 / C- 160 3-CH3〇-Ph C2H5 B-1 / C- 161 4-CH3〇-Ph C2H5 B-1 / C- 162 4-CF30-Ph C2H5 B-1 / C- 163 4-CF3CH2〇-Ph C2H5 B-1 / C- 164 4- (4-CI-PhO) -Ph C2H5 B-1 / C- 165 4- (4-CF3-PhO) -Ph C2H5 B-1 / C- 166 2,3-di-Cl-Ph C2H5 B-1 / C- 167 1-pyrrolyl C2H5 B-1 / C- 168 1-pyrazolyl C2H5 B-1 / C- 169 1,2,4-triazolyl C2H5 B-1 / C- 170 2-thiazolyl C2H5 B-1 / C- 171 1,3, 4-thiadiazolyl C2H5 B-1 / C- 172 CH3〇2CCH2 C2H5 B-1 / C- 173 CH3〇2〇CH (CH3) C2H5 B-1 / C- 174 NCCH2 η-〇3Η7 B-1 / C- 175 ch2 = chch2 iso-C3H7 B-1 / C- 176 hc ^ cch2 iso-C3H7 B-1 / C- 1.77 ch3c ^ cch2 iso-c3h7 B-1 / C- 178 (ring-c3h5) ch2 iso- C3H7 B-1 / C- 179 PhCH2 iso, C3H7 B-1 / C- 180 PhCH2CH2 iso-c3h7 B-1 / C- 181 (2-CI-Ph) CH2 iso-C3H7 B-1 / C- 182 (3 -CI-Ph) CH2 iso-c3h7 B-1 / C- 183 (4-CI-Ph) CH2 iso-c3h7 B-1 / C- 184 (2-CF3-Ph) CH2 iso-c3h7 B-1 / C -185 (3-CF3-Ph) CH2 iso-C3H7 B-1 / C- 186 (4-CF3-Ph) CH2 iso-c3h7 -68- (64) 200530182 compound R4 B-1 / C- 187 (2- CH3〇-Ph) CH2 iso-c3h7 B-1 / C 188 (3-CH3〇-Ph) CH2 iso-C3H7 B-1 / C- 189 (4-CH3〇-Ph) CH2 iso-C3H7 B-1 / C- 190 ch3o iso-c3h7 B-1 / C- 191 CH3CH2〇 iso-C3H7 B-1 / C · 192 η-〇3Η7〇 iso-c3h7 B-1 / C- 193 iso-C3H7O iso-c3h7 B- 1 / C- 194 ch2 = chch2o iso-c3h7 B-1 / C- 195 hc ^ cch2o iso-C3H7 B-1 / C- 196 PhCH2〇 iso-C3H7 B-1 / C- 197 Ph〇iso-C3H7 B- 1 / C- 198 Ph iso-C3H7 B-1 / C- 199 2-CI-Ph Iso-c3h7 B-1 / C- 200 3-CI-Ph iso-C3H7 B-1 / C- 201 4-CI-Ph iso-c3h7 B-1 / C- 202 2-CF3-Ph iso-c3h7 B- 1 / C- 203 3-CF3-Ph iso-C3H7 B-1 / C- 204 4-CF3-Ph iso-c3h7 B-1 / C- 205 2-CH30-Ph iso-C3H7 B-1 / C- 206 3-CH3〇-Ph iso-C3H7 B-1 / C- 207 4-CH3〇-Ph iso-C3H7 B-1 / C- 208 4-CF3〇-Ph iso-C3H7 B-1 / C- 209 4- CF3CH2〇-Ph iso-C3H7 B-1 / C- 210 4- (4-ΟΙ-ΡήΟ) -priced iso-c3h7 B-1 / C- 211 4- (4-CF3-PhO) -Ph iso-c3h7 B -1 / C- 212 2,3-Z: a-Ph iso-c3h7 B-1 / C- 213 1-pyrrolyl iso-c3h7 B-1 / C- 214 1-pyrazolyl iso-C3H7 B-1 / C- 215 1,2,4-triazole small iso-C3H7 B-1 / C- 216 2-thiazolyl iso-c3h7 B-1 / C- 217 1,3,4-thiadiazole-2- Base iso-C3H7 B-1 / C- 218 cf3ch2 iso-C3H7 B-1 / C- 219 CICH2CH2 iso-c3h7 -69- (65) 200530182 compound R6 R4 B-1 / C- 220 CICH2CH2CH2 iso-C3H7 B-1 / C- 221 CH3OCH2CH2 different. 3 latch 7 B-1 / C- 222 CH3CH2OCH2CH2 iso-c3h7 B-1 / C- 223 CH3OCH2CH2CH2 iso-C3H7 B-1 / C- 224 C2H5OCH2CH2CH2 iso-c3h7 B-1 / C- 225 n-C4H9〇CH2CH2CH2 iso- C3H7 B-1 / C- 226 (CH3〇) 2CHCH2 iso-c3h7 B-1 / C- 227 CH3O2CCH2 iso-c3h7 B-1 / C- 228 CH3〇2CCH (CH3) iso-C3H7 B-1 / C- 229 ncch2 iso-C3H7 B-1 / C- 230 nc (ch3) (iso-c3h7) third level_c4h9 B-1 / C- 231 ch2 = chch2 third level-c4h9 B-1 / C- 232 CHCCH2 third level-C4H9 B-1 / O 233 CH3CCCH2 Level 3-C4H9 B-1 / C- 234 (ring-c3h5) ch2 Level 3-c4h9 B-1 / C- 235 PhCH2 Level 3-c4h9 B-1 / C- 236 PhCH2CH2 Level 3 -C4H9 B-1 / C- 237 (2-CI-Ph) CH2 third stage -c4h9 B-1 / O 238 (3-CI-Ph) CH2 third stage -c4h9 B-1 / C- 239 (4-CI -Ph) CH2 Level 3 -C4H9 B-1 / C- 240 (2-CF3-Ph) CH2 Level 3 -c4h9 B-1 / C- 241 (3-CF3-Ph) CH2 Level 3 -c4h9 B-1 / C- 242 (4-CF3-Ph) CH2 third stage, c4h9 B-1 / C- 243 (2-CH3〇 " Ph) CH2 third stage-c4h9 B-1 / C- 244 (3-CH3〇-Ph ) CH2 Level 3-c4h9 B-1 / C- 245 (4-CH30-Ph) CH2 Level 3-c4h9 B-1 / O 246 CH3〇 Level 3-c4h9 B-1 / C- 247 CH3CH2O Level 3-C4H9 B -1 / C- 248 η-〇3Η7〇 Tertiary-c4h9 B-1 / C- 249 Iso-C3H7C) Tertiary-c4h9 B-1 / C- 250 CH2 = CHCH2〇 Tertiary-c4h9 B-1 / C- 251 hc ^ cch2o Tertiary Grade-c4h9 B-1 / C-252 PhCH2〇 Tertiary-c4h9 (66) 200530182 Compound R4 B-1 / C- 253 Ph〇 Tertiary-C4H9 B-1 / C- 254 Ph Tertiary-c4h9 B-1 / C- 255 2-CI-Ph Level III-C4H9 B-1 / C- 256 3-CI-Ph Level III-c4h9 B-1 / C- 257 4-CI-Ph Level III-C4H9 B-1 / C -258 2-CF3-Ph Class III-C4H9 B-1 / C- 259 3-CF3-Ph Class III-C4H9 B-1 / C- 260 4-CF3-Ph Class III-c4h9 B-1 / O 261 2 -CH3〇-Ph third stage -C4H9 B-1 / C- 262 3-CH3〇-Ph third stage, c4h9 B-1 / C- 263 4-CH3〇-Ph third stage -C4H9 B-1 / C- 264 4-CF3〇-Ph Tertiary-C4H9 B-1 / C- 265 4-CF3CH2〇-Ph Tertiary-C4H9 B-1 / C- 266 4- (4-CI-Ph〇) -Ph Tertiary-c4h9 B-1 / C- 267 4- (4-CF3-PhO) -Ph tertiary-c4h9 B-1 / C- 268 2,3-rCI-Ph tertiary-C4H9 B-1 / C- 269 1-pyrrole Base tertiary-C4H9 B-1 / C- 270 1 · pyrazolyl tertiary_C4H9 B-1 / C- 271 1,2,4-triazole small radical tertiary-c4h9 B-1 / C- 272 2 -Thiazolyl tertiary-c4h9 B-1 / C- 273 1,3,4-thiadiazol-2-yl tertiary-c4h9 B-1 / C- 274 CH3〇2CCH2 Level III-c4h9 B-1 / C- 275 CH3〇2CCH (CH3) Level III-c4h9 B-1 / C- 276 ncch2 Level III-c4h9 B-1 / C- 277 nc (ch3) (Iso-c3h7) c ch2 = chch2 B-1 / C- 278 ch2 = chch2 ch2 = chch2 B-1 / C- 279 HOCCH2 ch2 = chch2 B-1 / C- 280 CH3CCCH2 ch2 = chch2 B-1 / C- 281 (ring-c3h5) ch2 ch2 = chch2 B-1 / O 282 PhCH2 ch2 = chch2 B-1 / C- 283 PhCH2CH2 丨 ch2 = chch2 B-1 / C- 284 (2-CI-Ph) CH2 丨 ch2 = chch2 B-1 / C- 285 (3-CI-Ph) CH2, ch2 = chch2 (67) 200530182 compound R6 R4 B-1 / C- 286 (4-CI-Ph) CH2 ch2 = chch2 B-1 / C -287 (2-CF3-Ph) CH2 ch2 = chch2 B-1 / C- 288 (3-CF3-Ph) CH2 ch2 = chch2 B-1 / C- 289 (4-CF3-Ph) CH2 ch2 = chch2 B -1 / C- 290 (2-CH3〇-Ph) CH2 ch2 = chch2 B-1 / C- 291 (3-CH3〇-Ph) CH2 ch2 = chch2 B-1 / C- 292 (4-CH3〇- Ph) CH2 ch2 = chch2 B-1 / C- 293 ch3o ch2 = chch2 B-1 / C- 294 CH3CH2〇ch2 = chch2 B-1 / C- 295 η-〇3Η7〇ch2 = chch2 B-1 / C- 296 iso-c3h7o ch2 = chch2 B-1 / C- 297 ch2 = chch2o ch2 = chch2 B-1 / C- 298 chcch2o ch2 = chch2 B-1 / C- 299 PhCH2〇ch2 = chch2 B-1 / C- 300 PhO ch2 = chch2 B-1 / C- 301 Ph ch2 = chch2 B-1 / C- 302 2-CI-Ph ch2 = chch2 B-1 / C · 303 3-CI-Ph ch2 = chch2 B-1 / C- 304 4- CI-Ph ch2 = chch2 B-1 / C- 305 2-CF3-Ph ch2 = chch2 B-1 / C- 306 3-CF3-Ph ch2 = chch2 B-1 / C- 307 4-CF3-Ph ch2 = chch2 B-1 / C- 308 2-CH3〇-Ph ch2 = chch2 Β · 1 / C- 309 3-CH30-Ph ch2 = chch2 B-1 / C- 310 4-CH30-Ph ch2 = chch2 B-1 / C- 311 4-CF3〇-Ph ch2 = chch2 B-1 / C- 312 4-CF3CH2〇-Ph ch2 = chch2 B-1 / C- 313 'M-CI-PhCO-Ph ch2 = chch2 B-1 / C- 314 4. (4.CF3-PhO) ^ Ph ch2 = chch2 B-1 / C- 315 2,3-HCI-Ph ch2 = chch2 B-1 / C- 316 1-pyrrolyl ch2 = chch2 B -1 / C- 317 1-pyrazolyl, ch2 = chch2 B-1 / C- 318 1,2,4-triazole small group (ch2 = chch2 -72- (68) 200530182 compound FT3 R4 B-1 / C- 319 2-triazolyl ch2 = chch2 B-1 / Ο 320 1,3,4-thiadiazol-2-yl ch2 = chch2 B-1 / Ο 321 cf3ch2 ch2 = chch2 B-1 / C- 322 CICH2CH2 ch2 = chch2 B-1 / C- 323 CICH2CH2CH2 ch2 = chch2 B-1 / C- 324 CH30CH2CH2 ch2 = chch2 B-1 / C- 325 CH3CH20CH2CH2 ch2 = chch2 B-1 / C- 326 CH30CH2CH2CH2 CH2 = CHCH2 1 / O 327 C2H50CH2CH2CH2 c h2 = chch2 B-1 / C- 328 n-C4H9〇CH2CH2〇H2 ch2 = chch2 B-1 / C- 329 (CH3〇) 2CHCH2 ch2 = chch2 B-1 / C- 330 CH3O2CCH2 ch2 = chch2 B-1 / C- 331 CH3〇2CCH (CH3) ch2 = chch2 B-1 / C- 332 ncch2 ch2 = chch2 B-1 / C- 333 nc (ch3) (iso-c3h7) c PhCH2 B-1 / C- 334 ch2 = chch2 PhCH2 B-1 / C- 335 hc ^ cch2 PhCH2 B-1 / C- 336 ch3c ^ cch2 PhCH2 B-1 / C- 337 (ring-c3h5) ch2 PhCH2 B-1 / C- 338 PhCH2 PhCH2 B-1 / C- 339 PhCH2CH2 PhCH2 B-1 / C- 340 (2-CI-Ph) CH2 PhCH2 B-1 / C- 341 (3-a-Ph) CH2 PhCH2 B-1 / C- 342 (4-CI- Ph) CH2 PhCH2 B-1 / C- 343 (2-CF3-Ph) CH2 PhCH2 B-1 / C- 344 (3-CF3-Ph) CH2 PhCH2 B-1 / C- 345 (4-CF3-Ph) CH2 PhCH2 B-1 / C- 346 (2-CH3〇-Ph) CH2 PhCH2 B-1 / C- 347 (3-CH3〇-Ph) CH2 PhCH2 B-1 / C- 348 (4-CH3〇-Ph ) CH2 PhCH2 B-1 / C- 349 CH3〇PhCH2 B-1 / C- 350 CH3CH2O PhCH2 B-1 / C- 351 n_C3H7〇PhCH2 -73- (69) 200530182 Compound R0 R4 B-1 / C- 352 iso -c3h7o PhCH2 B-1 / C- 353 ch2 = chch2〇PhCH2 B-1 / C- 354 chcch2o PhCH2 B-1 / C- 355 PhCH2〇PhCH2 B-1 / C- 356 Ph〇PhCH2 B-1 / C-357 Ph PhCH2 B-1 / C- 358 2-CI-Ph PhCH2 B-1 / C- 359 3-CI-Ph PhCH2 B-1 / C- 360 4-CI-Ph PhCH2 B-1 / C- 361 2 -CF3-Ph PhCH2 B-1 / C- 362 3-CF3-Ph PhCH2 B-1 / C- 363 4-CF3-Ph PhCH2 B-1 / C- 364 2-CH3〇-Ph PhCH2 B-1 / C -365 3-CH3〇-Ph PhCH2 B-1 / C- 366 4-CH3〇-Ph PhCH2 B-1 / C- 367 4-CF30-Ph PhCH2 B-1 / C- 368 4-CF3CH2〇-Ph PhCH2 B-1 / C- 369 4- (4-CI-Ph〇) -Ph PhCH2 B-1 / C- 370 4- (4-CF3-PhO) -Ph PhCH2 B-1 / C- 371 2,3- Di Cl-Ph PhCH2 B-1 / C- 372 1-pyrrolyl PhCH2 B-1 / C- 373 1-pyrazolyl PhCH2 B-1 / C- 374 1,2,4-triazole small group PhCH2 B- 1 / C- 375 2-thiazolyl PhCH2 B-1 / C- 376 1,3,4-thiadiazol-2-yl PhCH2 B-1 / C- 377 cf3ch2 PhCH2 B-1 / C- 378 CICH2CH2 PhCH2 B -1 / C- 379 CICH2CH2CH2 PhCH2 B-1 / C- 380 CH30CH2CH2 PhCH2 B-1 / C- 381 CH3CH20CH2CH2 PhCH2 B-1 / C- 382 CH30CH2CH2CH2 PhCH2 B-1 / C- 383 C2H50CH2CH2CH2 PhCH2 B-1 / C- 384 n-C4H9〇CH2CH2CH2 PhCH2 -74- (70) 200530182 Compound R4 B-1 / C- 385 (CH3〇) 2CHCH2 PhCH2 B-1 / e- 386 CH (CH3) CH2CH2CH2CH2 B-1 / C- 387 CH2〇HBrCH2〇H2 B-1 / C- 388 CH2〇H (OH) CH2CH2 B-1 / C- 389 CH2CH = CHCH2 B-1 / C- 390 Ph Ph B-1 / C- 391 CH3SO2OCH2CH2CH2CH2 H B-1 / C- 392 CH2CH2CH2CH2CH2 B-1 / C- 393 CH2CH2OCH2CH2 B-1 / C- 394 CH2CH2SCH2CH2 B-1 / C- 395 CH2CH2NHCH2CH2 B-1 / C- 396 CH2〇H2N (CH3) CH2CH2 B-1 / C- 397 N = CHCH2CH2 -75- (71) 200530182 Table 3 Compound of formula (Icc)

(Icc) M = Na (compound D-1-D-397) or K (compound E-1-E-397) compound R6 R4 D-1 / E-1 ch3ch = chch2 ch3 D-1 / E-2 CH2 = C (CH3) CH2 ch3 D-1 / E-3 CH2 = CH (CH3) CH ch3 D-1 / E-4 CH2 = CHCH2CH2 ch3 D-1 / E-5 CH3CH = C (CH3) CH2 ch3 D- 1 / E-6 CH (CH3) HC = CHCH3 ch3 D-1 / E-7 C (CH3) 2HC = CH2 ch3 D-1 / E-8 CH2HC = C (CH3) 2 ch3 D-1 / E-9 ch3ch = chch2ch2 ch3 D-1 / E- 10 CH2 = CHCH2CH2CH2 ch3 D-1 / E- 11 chc = cch2 ch3 D-1 / E- 12 ch3c = cch2 ch3 D-1 / E- 13 HC ^ CCH (CH3) ch3 D-1 / E- 14 CH3C ^ CCH (CH3) ch3 D-1 / E- 15 ring-c3h5 ch3 D-1 / E- 16 ring-C5H9 ch3 D-1 / E- 17 ring-C6Hii ch3 D- 1 / E- 18 (ring-c3h5) ch2 ch3 D-1 / E- 19 (ring-c5h9) ch2 ch3 D-1 / E- 20 (ring ch3 D-1 / E- 21 PhCH2 ch3 D-1 / E -22 PhCH (CH3) ch3 -76- (72) 200530182 Compound R4 D-1 / E- 23 PhC (CH3) 2 ch3 D-1 / E- 24 PhCH2CH2 ch3 D-1 / E- 25 (2-F- Ph) CH2 ch3 D-1 / E- 26 (3-F-Ph) CH2 ch3 D-1 / E- 27 (4-F-Ph) CH2 ch3 D-1 / E- 28 (2-CI-Ph) CH2 ch3 D-1 / E- 29 (3-CI-Ph) CH2 ch3 D-1 / E- 30 (4-CI-Ph) CH2 ch3 D-1 / E- 31 (2-CF3-Ph) CH2 ch3 D-1 / E- 32 (3-CF3 -Ph) CH2 ch3 D-1 / E- 33 (4-CF3-Ph) CH2 ch3 D-1 / E- 34 (2-CH3〇-Ph) CH2 ch3 D-1 / E- 35 (3-CH3〇 -Ph) CH2 ch3 D-1 / E- 36 (4-CH3〇-Ph) CH2 ch3 D-1 / E- 37 ch3o ch3 D-1 / E- 38 CH3CH2〇ch3 D-1 / E- 39 η- 〇3Η7〇ch3 D-1 / E- 40 iso-c3h7o ch3 D-1 / E · 41 ch2 = chch2o ch3 D-1 / E- 42 CH2 = C (CH3) CH2〇ch3 D-1 / E- 43 CH2 = CHCH (CH3) 0 ch3 D-1 / E- 44 CH2 = CHCH (CH3) 〇ch3 D-1 / E- 45 CH2 = CHC (CH3) 2〇ch3 D-1 / E- 46 ch3ch = chch2o ch3 D -1 / E- 47 HOCCH20 ch3 D-1 / E- 48 CH3C ^ CCH2〇ch3 D-1 / E- 49 HC ^ CCH (CH3) 〇ch3 D-1 / E- 50 CH3〇2CCH (CH3) 〇ch3 D-1 / E- 51 ch3〇2cc (ch3) 2o ch3 D-1 / E- 52 CH302CCH20 ch3 D-1 / E- 53 PhCH2〇ch3 D-1 / E- 54 PhO ch3 D-1 / E- 55 Ph ch3 -77- (73) 200530182 compound r " R4 D-1 / E- 56 2-F-Ph ch3 D-1 / E- 57 3-F-Ph ch3 D-1 / E- 58 4-F- Ph ch3 D-1 / E- 59 2-CI-Ph ch3 D-1 / E- 60 3-CI-Ph ch3 D-1 / E- 61 4-CI-Ph ch3 D-1 / E- 62 2- Br-Ph ch3 D-1 / E- 63 3-Br-Ph ch3 D-1 / E- 64 4-Br-Ph ch3 D-1 / E- 65 2-l-Ph ch3 D-1 / E- 66 3-l- Ph ch3 D-1 / E- 67 4-l-Ph ch3 D-1 / E- 68 2-CF3-Ph ch3 D-1 / E- 69 3-CF3-Ph ch3 D-1 / E- 70 4- CF3-Ph ch3 D-1 / E- 71 2-CH3-Ph ch3 D-1 / E- 72 3-CH3-Ph ch3 D-1 / E- 73 4-CH3-Ph ch3 D-1 / E- 74 2-CH3〇-Ph ch3 D-1 / E- 75 3-CH3〇-Ph ch3 D-1 / E- 76 4-CH3〇-Ph ch3 D-1 / E- 77 2-N〇2-Ph ch3 D-1 / E- 78 3-N02-Ph ch3 D-1 / E- 79 4-N02-Ph ch3 D-1 / E- 80 2-CN-Ph ch3 D-1 / E- 81 3-CN- Ph ch3 D-1 / E- 82 4-CN-Ph ch3 D-1 / E- 83 2-C02Me-Ph ch3 D-1 / E- 84 3-C〇2Me-Ph ch3 D-1 / E- 85 4-C02Me-Ph ch3 D-1 / E- 86 2-CF3〇-Ph ch3 D-1 / E- 87 3-CF3〇-Ph 'ch3 D-1 / E- 88 4-CF3〇-Ph 丨 ch3 -78- (74) 200530182 Compound R6 R4 D-1 / E- 89 4-CF3CH2〇-Ph ch3 D-1 / E- 90 4- (4-CI-PhO) -Ph ch3 D-1 / E- 91 4- (4-CF3-PhO) -Ph ch3 D-1 / E- 92 2,3-di-Cl-Ph ch3 D-1 / E- 93 2,4-di-Cl-Ph ch3 D-1 / E- 94 2,5-di-Cl-Ph ch3 D-1 / E- 95 2,6-di-Cl-Ph ch3 D-1 / E- 96 3,4--Cl-Ph ch3 D-1 / E- 97 3 , 5-—Cl-Ph ch3 D-1 / E- 98 2- Port specific steep base ch3 D-1 / E- 99 3-Pin specific steep base ch3 D-1 / E- 100 'Pyridyl ch3 D-1 / E- 101 2-pyrimidinyl ch3 D-1 / E- 102 1-pyrrolyl ch3 D-1 / E- 103 1-pyrazolyl ch3 D-1 / E- 104 3- Pyrazolyl ch3 D-1 / E- 105 1,2,4-triazolyl ch3 D-1 / E- 106 1,2,4-triazol-3-yl ch3 D-1 / E- 107 2 -Furyl ch3 D-1 / E- 108 3-furyl ch3 D-1 / E- 109 2-thienyl ch3 D-1 / E- 110 3-thienyl ch3 D-1 / E- 111 2-thiazole Ch3 D-1 / E112 1,3,4-thiadiazol-2-yl ch3 D-1 / E- 113 3-isoxazolyl ch3 D-1 / E- 114 cf3ch2 ch3 D-1 / E- 115 CICH2CH2 ch3 D-1 / E- 116 CICH2CH2CH2 ch3 D-1 / E- 117 CH30CH2CH2 ch3 D-1 / E- 118 CH3CH20CH2CH2 ch3 D-1 / E- 119 CH30CH2CH2CH2 ch3 D-1 / E- 120 C2H50CH2CH2CH2 ch3 D-1 / E- 121 n-C4H9〇CH2CH2CH2 ch3 -79- (75) 200530182 Compound R4 D-1 / E- 122 (CH3〇) 2CHCH2 ch3 D-1 / E- 123 (CH3〇) 2C = CH2 ch3 D-1 / E- 124 (CH3〇2) C = CH (CH3) ch3 D-1 / E- 125 CH3〇2〇C (CH3) 2 ch3 D-1 / E- 126 ncch2 ch3 D-1 / E -127 NC (CH3) (iso-C3H7) C ch3 D-1 / E- 128 (1-pyrrolidinyl) ch2ch2 C2H5 D-1 / E- 129 ch2 = chch2 C2H5 D-1 / E- 130 chc = ch2 C2H5 D-1 / E- 131 ch3c ^ cch2 C2H5 D-1 / E- 132 (ring-c3h5) ch2 C2H5 D-1 / E- 133 PhCH2 C2H5 D-1 / E- 134 PhCH2CH2 C2H5 D-1 / E- 135 (2-CI-Ph) CH2 C2H5 D-1 / E- 136 (3-CI-Ph) CH2 C2H5 D-1 / E- 137 (4-CI-Ph) CH2 C2H5 D-1 / E -138 (2-CF3-Ph) CH2 C2H5 D-1 / E- 139 (3-CF3-Ph) CH2 C2H5 D-1 / E- 140 (4-CF3-Ph) CH2 C2H5 D-1 / E- 141 (2-CH3〇-Ph) CH2 C2H5 D-1 / E- 142 (3-CH3〇-Ph) CH2 C2H5 D-1 / E- 143 (4-CH30-Ph) CH2 C2H5 D-1 / E- 144 ch3o C2H5 D-1 / E- 145 CH3CH2〇C2H5 D-1 / E- 146 η-〇3Η7〇C2H5 D-1 / E- 147 iso, C3H7O C2H5 D-1 / E- 148 ch2 = chch2o C2H5 D-1 / E- 149 hc ^ cch2o C2H5 D-1 / E- 150 PhCH2〇C2H5 D-1 / E- 151 Ph〇C2H5 D-1 / E- 152 Ph C2H5 D-1 / E- 153 2-CI-Ph C2H5 D-1 / E- 154 3-CI-Ph C2H5 -80- (76) 200530182 Compound R3 R4 D-1 / E- 155 4-CI-Ph C2H5 D-1 / E- 156 2-CF3-Ph C2H5 D -1 / E- 157 3-CF3-Ph C2H5 D-1 / E- 158 4-CF3-Ph C2H5 D-1 / E- 159 2-CH3〇-Ph C2H5 D-1 / E- 160 3-CH3〇 -Ph C2H5 D-1 / E- 161 4-CH3〇-Ph C2H5 D-1 / E- 162 4-CF3〇-Ph C 2H5 D-1 / E- 163 4-CF3CH2〇-Ph C2H5 D-1 / E- 164 4- (4-CI-PhO) -Ph C2H5 D-1 / E- 165 4- (4-CF3-PhO) -Ph C2H5 D-1 / E- 166 2,3-diCl-Ph C2H5 D-1 / E- 167 1-pyrrolyl C2H5 D-1 / E- 168 1-pyrazolyl C2H5 D-1 / E- 169 1,2,4-triazolyl C2H5 D-1 / E- 170 2-thiazolyl C2H5 D-1 / E- 171 1,3,4-thiadiazol-2-yl C2H5 D-1 / E -172 CH3〇2CCH2 C2H5 D-1 / E- 173 CH3〇2CCH (CH3) C2H5 D-1 / E- 174 NCCH2 n-C3H7 D-1 / E- 175 ch2 = chch2 iso-C3H7 D-1 / E- 176 hc ^ cch2 iso-c3h7 D-1 / E- 177 ch3c ^ cch2 iso-c3h7 D-1 / E- 178 (ring-c3h5) ch2 iso-C3H7 D-1 / E- 179 PhCH2 iso-C3H7 D-1 / E- 180 PhCH2CH2 iso-c3h7 D-1 / E- 181 (2-C \ -Ph) CH2 iso-C3H7 D-1 / E- 182 (3-CI-Ph) CH2 iso-c3h7 D-1 / E -183 (4-CI-Ph) CH2 iso-c3h7 D-1 / E- 184 (2-CF3-Ph) CH2 iso · 〇3η7 D-1 / E- 185 (3-CF3-Ph) CH2 iso-C3H7 D-1 / E- 186 (4-CF3-Ph) CH2 iso-C3H7 D-1 / E- 187 (2-CH30-Ph) CH2 iso-C3H7 (77) 200530182 Compound R4 D-1 / E- 188 ( 3-CH3〇-Ph) CH2 iso-c3h7 D-1 / E- 189 (4-CH3〇-Ph) CH2 iso-c3h7 D-1 / E- 190 ch3o iso-C3H7 D-1 / E- 191 CH3CH2〇 iso-c3h7 D-1 / E- 192 n-〇3H7〇 iso-c3h7 D-1 / E- 193 iso-c3h7〇 iso-c3h7 D-1 / E- 194 ch2 = chch2o iso-c3h7 D-1 / E- 195 HC = CCH2〇iso-C3H7 D-1 / E- 196 PhCH2〇 iso-C3H7 D-1 / E- 197 Ph〇 iso-c3h7 D-1 / E- 198 Ph Iso-c3h7 D-1 / E- 199 2-CI-Ph iso-c3h7 D-1 / E- 200 3-CI-Ph iso-C3H7 D-1 / E- 201 4-CI-Ph iso-C3H7 D- 1 / E- 202 2-CF3-Ph iso-c3h7 D-1 / E- 203 3-CF3-Ph iso-C3H7 D-1 / E- 204 4-CF3-Ph iso-C3H7 D-1 / E- 205 2-CH3〇-Ph iso-c3h7 D-1 / E- 206 3-CH3〇-Ph iso-C3H7 D-1 / E- 207 4-CH30-Ph iso-c3h7 D-1 / E- 208 4-CF3 〇-Ph iso-C3H7 D-1 / E- 209 4-CF3CH2 〇-Ph iso-c3h7 D-1 / E- 210 4- (4-CI-PhO) -Ph iso-c3h7 D-1 / E- 211 4- (4-CF3-PhO) -Ph iso-c3h7 D-1 / E- 212 2,3-diCl-Ph iso-c3h7 D-1 / E- 213 1-pyrrolyl iso-C3H7 D-1 / E- 214 1-pyrazolyliso-c3h7 D-1 / E- 215 1,2,4-triazolyl-1-yliso-C3H7 D-1 / E- 216 2-thiazolyliso-c3h7 D- 1 / E- 217 1,3,4-thiadiazol-2-yliso-C3H7 D-1 / E- 218 cf3ch2 iso-C3H7 D-1 / E- 219 CICH2CH2 iso-c3h7 D-1 / E- 220 CICH2CH2CH2 iso-C3H7 -82- (78) 200530182 Compound R4 D-1 / E- 221 CH3OCH2CH2 iso-c3h7 D-1 / E- 222 CH3CH2OCH2CH2 iso-C3H7 D-1 / E- 223 CH3OCH2CH2CH2 iso-c3h7 -1 / E- 224 C2H5OCH2CH2CH2 iso-C3H7 D-1 / E- 225 n-C4H9OCH2CH2CH2 iso-C3H7 D-1 / E- 226 (CH3〇) 2CHCH2 iso-C3H7 D-1 / E- 227 CH3O2CCH2 iso-C3H7 D -1 / E- 228 CH3〇2CCH (CH3) iso-C3H7 D-1 / E- 229 ncch2 iso-C3H7 D-1 / E- 230 nc (ch3) (iso-c3h7) third stage-c4h9 D-1 / E- 231 CH2 = CHCH2 Level 3-C4H9 D-1 / E- 232 CHCCH2 Level 3-c4h9 D-1 / E- 233 CH3CCCH2 Level 3-c4h9 D-1 / E- 234 (Ring-C3H5) CH2 Level 3- C4H9 D-1 / E- 235 PhCH2 Level 3-c4h9 D-1 / E- 236 PhCH2CH2 Level 3-C4H9 D-1 / E- 237 (2-CI-Ph) CH2 Level 3-C4H9 D-1 / E- 238 (3-CI-Ph) CH2 Level 3 -C4H9 D-1 / E- 239 (4-CI-Ph) CH2 Level 3 -c4h9 D-1 / E- 240 (2-CF3-Ph) CH2 Level 3- c4h9 D-1 / E- 241 (3-CF3-Ph) CH2 third stage -c4h9 D-1 / E- 242 (4-CF3-Ph) CH2 third stage -c4h9 D-1 / E- 243 (2-CH3 〇-Ph) CH2 third stage-c4h9 D-1 / E- 244 (3-CH3〇-Ph) CH2 third stage-C4H9 D-1 / E- 245 (4-CH30-Ph) CH2 third stage -c4h9 D-1 / E- 246 CH3〇 Tertiary-C4H9 D-1 / E- 247 CH3CH2O Tertiary-c4h9 D-1 / E- 248 η-〇3Η7〇 Tertiary-c4h9 D-1 / E- 249 Iso-c3h7o third stage -c4h9 D-1 / E- 250 ch2 = chch2o third stage -c4h9 D-1 / E- 251 hc = cch2o third stage -c4h9 D-1 / E- 252 PhCH2〇 third stage -c4h9 D- 1 / E- 253 Ph〇 Tertiary-c4h9 -83- (79) 200530182 Compound R4 D-1 / E · 254 Ph Tertiary-C4H9 D-1 / E- 255 2-CI-Ph Tertiary-c4h9 D- 1 / E- 256 3-CI-Ph Class III-C4H9 D-1 / E- 257 4-CI-Ph Class III-c4h9 D-1 / E- 258 2-CF3-Ph Class III-C4H9 D-1 / E- 259 3-CF3-Ph Class III-C4H9 D-1 / E- 260 4-CF3-Ph Class III-C4H9 D-1 / E- 261 2-CH3〇-Ph Class III_C4H9 D-1 / E -262 3-CH3〇-Ph Tertiary-C4H9 D-1 / E- 263 4-CH3〇-Ph ΞΜ -C4H9 D-1 / E- 264 4-CF3〇-Ph Tertiary-c4h9 D-1 / E -265 4-CF3CH2〇-Ph -C4H9 D-1 / E- 266 4- (4-CI-Ph〇) -Ph Tertiary -c4h9 D-1 / E- 267 4- (4-CF3-PhO)- Ph tertiary-c4h9 D-1 / E- 268 2,3-diCl-Ph tertiary-c4h9 D-1 / E- 269 1-pyrrolyl tertiary-c4h9 D-1 / E- 270 1-pyrrolyl Third-level-c4h9 D-1 / E- 271 1,2,4- Triple-A small base three-level-C4H9 D-1 / E- 272 2-thiazolyl tertiary-C4H9 D-1 / E- 273 1,3,4-thiadiazol-2-yl tertiary-c4h9 D-1 I E- 274 CH3〇2CCH2 tertiary-c4h9 D -1 / E- 275 CH3〇2CCH (CH3) Level 3 -c4h9 D-1 / E- 276 NCCH2 Level 3 -C4H9 D-1 / E- 277 nc (ch3) (iso-c3h7) c ch2 = chch2 D- 1 / E- 278 ch2 = chch2 ch2 = chch2 D-1 / E- 279 hc ^ cch2 ch2 = chch2 D-1 / E- 280 CH3CCCH2 ch2 = chch2 D-1 / E- 281 (ring-c3h5) ch2 ch2 = chch2 D-1 / E- 282 PhCH2 ch2 = chch2 D-1 / E- 283 PhCH2CH2 ch2 = chch2 D-1 / E- 284 (2-CI-Ph) CH2 ch2 = chch2 D-1 / E- 285 (3 ^ Ph) CH2 ch2 = chch2 D-1 / E- 286 (4-CI-Ph) CH2 ch2 = chch2 -84- (80) 200530182 Compound R4 D-1 / E- 287 (2-CF3-Ph) CH2 ch2 = chch2 D-1 / E- 288 (3-CF3-Ph) CH2 ch2 = chch2 D-1 / E- 289 (4-CF3-Ph) CH2 ch2 = chch2 D-1 / E- 290 (2-CH3〇 -Ph) CH2 ch2 = chch2 D-1 / E- 291 (3-CH30-Ph) CH2 ch2 = chch2 D-1 / E- 292 (4-CH3〇-Ph) CH2 ch2 = chch2 D-1 / E- 293 ch3o ch2 = chch2 D-1 / E- 294 CH3CH2〇ch2 = chch2 D-1 / E- 295 η-〇3Η7〇CH2 = CHCH2 D-1 / E- 296 iso-c3h7o ch2 = chch2 D-1 / E -297 ch2 = chch2o ch2 = chch2 D-1 / E- 298 CHCCH2 O ch2 = chch2 D-1 / E- 299 PhCH2〇ch2 = chch2 D-1 / E- 300 PhO ch2 = chch2 D-1 / E- 301 Ph ch2 = chch2 D-1 / E- 302 2-CI-Ph ch2 = chch2 D-1 / E- 303 3-CI-Ph ch2 = chch2 D-1 / E- 304 4-CI-Ph ch2 = chch2 D-1 / E- 305 2-CF3-Ph ch2 = chch2 D- 1 / E- 306 3-CF3-Ph ch2 = chch2 D-1 / E- 307 4-CF3-Ph ch2 = chch2 D-1 / E- 308 2-CH3〇-Ph ch2 = chch2 D-1 / E- 309 3-CH3〇-Ph ch2 = chch2 D-1 / E- 310 4-CH3〇-Ph ch2 = chch2 D-1 / E- 311 4-CF3〇-Ph ch2 = chch2 D-1 / E- 312 4 -CF3CH2〇-Ph ch2 = chch2 D-1 / E- 313 4- (4-CI-PhO) -Ph ch2 = chch2 D-1 / E- 314 4- (4-CF3-PhO) -Ph ch2 = chch2 D-1 / E- 315 2,3--Cl-Ph ch2 = chch2 D-1 / E- 316 1-pyrrolyl ch2 = chch2 D-1 / E- 317 1-pyrazolyl ch2 = chch2 D-1 / E- 318 1,2,4-triazol-1-yl ch2 = chch2 D-1 / E- 319 2-thiadiazole ch2 = chch2 -85- (81) 200530182 compound R4 D-1 / E- 320 1,3,4-thiadiazol-2-yl ch2 = chch2 D-1 / E- 321 cf3ch2 ch2 = chch2 D-1 / E- 322 CICH2CH2 ch2 = chch2 D-1 / E- 323 CICH2CH2CH2 ch2 = chch2 D -1 / E- 324 CH30CH2CH2 ch2 = chch2 D-1 / E- 325 CH3CH20CH2CH2 ch2 = chch2 D-1 / E- 326 CH30CH2CH2CH2 ch2 = chch2 D-1 / E- 327 C2H50CH2CH2CH2 ch2 = chch2 D-1 / E- 328 n-C4H9〇CH2CH2CH2 ch2 = chch2 D-1 / E- 329 (CH3〇) 2. HCH2 ch2 = chch2 D-1 / E- 330 CH3O2CCH2 ch2 = chch2 D-1 / E- 331 CH3〇2CCH (CH3) ch2 = chch2 D-1 / E- 332 ncch2 ch2 = chch2 D-1 / E- 333 nc (ch3) (iso-c3h7) c PhCH2 D-1 / E- 334 ch2 = chch2 PhCH2 D-1 / E- 335 HOCCH2 PhCH2 D-1 / E- 336 CH30CCH2 PhCH2 D-1 / E- 337 (ring-C3H5 ) CH2 PhCH2 D-1 / E- 338 PhCH2 PhCH2 D-1 / E- 339 PhCH2CH2 PhCH2 D-1 / E- 340 (2-CI-Ph) CH2 PhCH2 D-1 / E- 341 (3-CI-Ph ) CH2 PhCH2 D-1 / E- 342 (4-CI-Ph) CH2 PhCH2 D-1 / E- 343 (2-CF3-Ph) CH2 PhCH2 D-1 / E- 344 (3-CF3-Ph) CH2 PhCH2 D-1 / E- 345 (4-CF3-Ph) CH2 PhCH2 D-1 / E- 346 (2-CH3〇-Ph) CH2 PhCH2 D-1 / E- 347 (3-CH3OPh) CH2 PhCH2 D- 1 / E- 348 (4-CH3〇-Ph) CH2 PhCH2 D-1 / E- 349 CH3〇PhCH2 D-1 / E- 350 CH3CH2O PhCH2 D-1 / E- 351 η-〇3Η7〇PhCH2 D-1 / E- 352 iso-C3H7C) PhCH2 -86- (82) 200530182 compound R4 D-1 / E- 353 ch2 = chch2o PhCH2 D-1 / E- 354 chcch2o PhCH2 D-1 / E- 355 PhCH2〇PhCH2 D-1 / E- 356 Ph〇PhCH2 D-1 / E- 357 Ph PhCH2 D-1 / E- 358 2-CI-Ph PhCH2 D-1 / E- 359 3 -CI-Ph PhCH2 D-1 / E- 360 4-CI-Ph PhCH2 D-1 / E- 361 2-CF3-Ph PhCH2 D-1 / E- 362 3-CF3-Ph PhCH2 D-1 / E- 363 4-CF3-Ph PhCH2 D-1 / E- 364 2-CH30_Ph PhCH2 D-1 / E- 365 3-CH3〇-Ph PhCH2 D-1 / E- 366 4-CH3〇-Ph PhCH2 D-1 / E- 367 4-CF3〇-Ph PhCH2 D-1 / E- 368 4-CF3CH2〇-Ph PhCH2 D-1 / E- 369 4- (4-CI-PhO) -Ph PhCH2 D-1 / E- 370 4- (4-CF3-PhO) -Ph PhCH2 D-1 / E- 371 2,3-di-Cl-Ph PhCH2 D-1 / E- 372 1-pyrrolidinyl PhCH2 D-1 / E- 373 1-pyridine Oxazolyl PhCH2 D-1 / E- 374 1,2,4-triazole small group PhCH2 D-1 / E- 375 2-thiazolyl PhCH2 D-1 / E- 376 1,3,4-thiadiazole- 2-base PhCH2 D-1 / E- 377 cf3ch2 PhCH2 D-1 / E- 378 CICH2CH2 PhCH2 D-1 / E- 379 CICH2CH2CH2 PhCH2 D-1 / E- 380 CH30CH2CH2 PhCH2 D-1 / E- 381 CH3CH20CH2 PhCH2 D -1 / E- 382 CH30CH2CH2CH2 PhCH2 D-1 / E- 383 C2H50CH2CH2CH2 PhCH2 D-1 / E- 384 n-C4H9〇CH2CH2CH2 PhCH2 D-1 / E- 385 (CH3〇) 2CHCH2 PhCH2 -87- 2005301 82 (83) Compound R4 D-1 / E- 386 CH (CH3) CH2CH2CH2CH2 D-1 / E- 387 CH2CHBrCH2CH2 D-1 / E- 388 CH2CH (〇H) CH2CH2 D-1 / E- 389 CH2CH = CHCH2 D -1 / E- 390 Ph Ph D-1 / E- 391 CH3SO2OCH2CH2CH2CH2 H D-1 / E- 392 CH2CH2CH2CH2CH2 D-1 / E- 393 CH2CH2OCK2CH2 D-1 / E- 394 CH2CH2SCH2CH2 D-1 / E- 395 CH2CH2NHCH2CH2 D -1 / E- 396 CH2CH2N (CH3) CH2CH2 D-1 / E- 397 n = chch2ch2 B. Preparation Example a) The powder is prepared by mixing 10 parts by weight of the active compound and 90 parts by weight of talc as an inert substance. A hammer mill was used to pulverize the mixture into powder. b) Wettable powder that is easily dispersed in water is prepared by mixing 25 parts by weight of active compound, 65 parts by weight of quartz-containing kaolin as an inert substance,] 0 parts by weight of potassium lignosulfonate and 1 part by weight as wetting And dispersant were obtained by pulverizing the mixture with sodium oleyl methyltaurate and a pin-disk honing machine. c) A dispersion concentrate that is easily dispersed in water is prepared by mixing 40 parts by weight of the active compound with 7 parts by weight of thiosuccinic acid monoester, 2 parts by weight of sodium lignosulfonate and 51 parts by weight of water, It is prepared by grinding the mixture to a fineness of less than 5 microns. d) The emulsifiable concentrate can be selected from 15 parts by weight of active compound, 75 parts by weight of 88-2005-30182 (84) parts of cyclohexane as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier ( 10 EO). e) Granules can be prepared from 2 to 15 parts by weight of active compound and inert particulate carrier material (such as attapulgite, pumice particles and / or quartz sand). The suspension of the wettable powder of Example b) contained 30% solids for ease of use, and it was sprayed on the wollastonite particles and the ingredients were dried and carefully mixed. Wettable powders total about 5% by weight of the final particles and inert carrier material to about 95% by weight of the final particles. C. Biological Examples Example 1 A germinated broad bean (Vicia faba) with young roots was transferred to a brown glass bottle filled with tap water, and then about 1,000 black bean aphids (Aphis fabae) were colonized. The plants and insects are then immersed in an aqueous solution of the compound to be examined. After the solution is discharged, plants and animals are stored in a climate chamber (16 hours of light / day, 25 ° C ’40-60% relative atmospheric humidity). After 3 and 6 days of storage, the effects of the compounds on aphids were determined. At a concentration of 300 ppm (based on the content of the active compound), the compounds of the present invention cause 90-100% mortality of aphids. Example 2 A germinated silkworm (Vicia faba) with young roots was transferred to a brown glass bottle filled with tap water. Pipette four milliliters of the aqueous solution of the formulation to be inspected into a brown glass bottle. The broad beans were then densely colonized into -89- 200530182 (85) approx. 00 black bean aphids (Aphis fab ae). Plants and animals are then stored in a climate chamber (16 hours of light / day, 25 ° C, 40-60% relative atmospheric humidity). After 3 and 6 days of storage, the compound's effect on the aphid's root-system was determined. At a concentration of 30 ppm (based on the content of the active compound), the compounds of the present invention cause 90 to 100% mortality of aphids via root-system activity.

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Claims (1)

200530182 (1) 10. Scope of patent application 1. A method for preparing N-disubstituted-N '-[4-haloalkylpyridine (pyrimidinyl) carbonylcarbonylcarbamide of formula (I), R1 〇 〇 〇 (〇) m II 3 4 Ν—C—NR3R4 R2 (丨) where A is CH or N; R1 is (C] -C4) -haloalkyl; R2 is fluorene or M; M is an organic or inorganic cation; R3 (C) -C8) -alkyl, (C3-C6) -alkenyl, (C3-C6) -alkynyl, (C] -C8) -alkoxy, (C3-C6) -enoxy, (C3-C6) -alkynyloxy, (C3-C8) -cycloalkyl, (C3-C8) -cycloalkyl- (C) -C6) -alkyl, 0-CH2- (C3-C8)- Cycloalkyl, where the aforementioned nine groups are unsubstituted or substituted with one or more R5 groups, or are aryl, heterocyclyl, aryloxy, heterocyclooxy, -CH2-aryl, -0- CH2-aryl, -CH2-heterocyclyl, -0-CH2-heterocyclyl, wherein the aforementioned eight groups are unsubstituted or substituted with one or more R6 groups; R4 is (C "C8) -alkyl, (C3-C6) -alkenyl, (C3-C6) -quick radical, (C3-C8) -cyclo-radical, (C3-C8) -cyclo-radical- (Ci-C6) _alkyl, wherein Each group is unsubstituted or substituted with -91-200530182 (2) through one or more R5 groups, or is an aryl group, heterocyclic group, -CH2-aryl group, -CH2-heterocyclic group, of which the aforementioned four Is unsubstituted or substituted with one or more R6 groups; or R3 and R4 are N atoms together form a 3-8 membered saturated, unsaturated or aromatic heterocyclic ring, which optionally further comprises up to three heteroatoms selected from N, S and 0 and is unsubstituted or substituted by one or more (C) -C 6) -alkyl, (C ^ Cs) -haloalkyl or R5 group substitution; R5 is halogen, ((^-(: 6) -alkoxy, haloalkoxy, S (O )-((^-06) -alkyl, S (〇) ^ (C ^ C ^)-haloalkyl 'CN, COO (Ci-C6) -alkyl, N02, N [(C) -C6 ) -Alkyl] 2, phenoxy, unsubstituted or substituted with one or more groups selected from () -alkyl, (Ci-C6) -haloalkyl and halogen; R6 is R5, (C) -C6) _alkyl, (Cl-C6) -haloalkyl; m is 0 or 1, and η is 0, 1 or 2, which is obtained by making a 4-haloalkane of formula (II) in the presence of a base Pyridyl (pyrimidinyl) carboxamide, Where A, R1, R2 and m have the meanings indicated by formula (I), • 92- 200530182 (3) reacts with a compound of formula (III), x-co—NR3R4 (III) where X is Produces NNI or — -0 — R7. R7 is (Ci-Cg) -Cycyl, (C3-C6) -Cycyl, alkynyl, (c3-c8) -cycloalkyl, (c3-c8) -cyclo Alkyl-alkyl, aryl, heterocyclyl, aryl- (c) -c4) -alkyl (Cra) -alkyl, where these groups are unsubstituted or via-from halogen, CN and NO2 And R3, R4 have the meanings indicated by formula (I). 2. As the method of the first patent application, the formula (I and the index have the following meanings: A is CH: R1 is CF3; R2 is M or Η; M is Li, Na, K, Cs, Ca2 + / 2, N [(C group) 4, such as N (CH3) 4, N (C2H5) 4; R3 is (C] -C8) -alkyl, (C3-C6) -alkenyl, alkoxy, (C) -C8 ) -Cyclooxy, (C3-C6) -Like oxygen C.6) -alkynyloxy, (c3-c8) -cycloalkyl, (c3-c8) (Ci-C6) -alkyl, o-ch2 -(c3-c8) -cycloalkyl, $ is unsubstituted or substituted with one or more R5 groups, or ί (c3-c6)-(C! -C4)-or heterocyclyl-one or (Multiple choices) symbols: 1-C 4) · yuan (c3-c6)-radical, (c3--ring yuan-the aforementioned nine i aryl, hetero-93- 200530182 (4) Xiang radical, Aryloxy, heterocyclooxy, -CHtaryl 'are called -heterocyclyl, _〇_CH2_heterocyclyl, where ^ -0-CH2-aryl, _- substituted or substituted by one or more R6 groups Substitution; ^ eight groups without R4 is (G-Cd-courtyard, (C3_c6 alkynyl, (C3-C8) _ cycloalkyl cloth, (C3-C6)-, 3 L 8). Ling Yuanji, in which the aforementioned five groups are unsubstituted 4 · (c 「C6)-substituted, or are aryl, The aforementioned four groups in the cyclic group, _CH2_aryl group, or multiple r5 groups are unM-CH2 -heterocyclyl 'whose u 1U group is unsubstituted or substituted by-or R 5 ^^^ / ^ K Group substitution, R is halogen, (c) -c6) -alkoxy group; 4 (Ci-C6) -haloalkoxy C] -C6) -sinyl group, R6 is R5, m is 0; n is 0, 1 or 2. 3. According to the method in the scope of the patent application, the symbols in formula (ιπ) have the following meanings: X is 0-R7 and R7 is unsubstituted or mono- or polyhalo (preferably F and / Or C 丨) -substituted (C) -C6) -fluorenyl or (CrC6) -alkenyl, phenyl or benzyl. 4 · The method according to item 1 of the patent application, wherein the formula (11) The mole ratio of fluorene to compound (III) is 1: 1 -1.;! 5. The method according to item 1 of the patent application range, wherein 1 to 1.1 equivalents (based on fluorene of formula (II) are used ) Is selected from the group consisting of hydroxides of alkali metals and alkaline earth metals and (c) -c4) -alcoholates, alkyl lithium compounds, metal hydrides, carbonates and acetates of alkali metals and alkaline earth metals, having C] -C4 -Alkane-94- 200530182 (5) tertiary amine and sterically hindered nitrogen Base. 6. A compound of formula (I a), Among them, R3, R4 and m have the meanings indicated by the formula (I) in the first scope of the patent application. 7 · a compound of formula (I b), Wherein R11 is a -haloalkyl group other than CF3; and A, R3, R4, and m have the meanings indicated by formula (I) in the first item of the patent application scope. 8.-a compound of formula (Ic), -95- 200530182 (6) (〇) m (lc) wherein M is an inorganic or organic cation, and A, R1, R3, R4, and m have the meanings indicated by the formula (I) in item 1 of the scope of patent application. 9. A composition for controlling harmful arthropods and worms, comprising an effective amount of at least one compound according to formula (la), (lb) or (Ic) according to item 6, 7 or 8 of the scope of patent application, using Conventional additives or auxiliaries for such applications. 10. The composition according to item 9 of the scope of patent application, which comprises at least one additional arthropodicidal and / or wormicidal (h e 1 m i n t h i c i d a 1) active compound. 1 1 · A method for controlling harmful arthropods and / or worms, in which the pests are in direct or indirect contact with the compounds in the scope of claims 6 to 8 of the patent application. 12.-A seed material coated with or containing an arthropod and / or worm-killing effective amount of the patented compounds Nos. 6-8. 1 3. A veterinary medicinal product comprising a compound in the scope of claims 6 to 8 of the patent application. -96- 200530182 VII. Designated representative map ^ a) The designated representative map in this case is: None (2,5, the component representative symbols of the representative map are simply explained: None 8. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: (〇) m -5-