DD263220A5 - SCHAEDLINGSBEKAEMPFUNGSMITTEL - Google Patents

Abstract

The invention relates to pesticides containing as active ingredient new pyrimidine derivatives. The invention provides pest control agents which have good plant tolerance and warm-blood toxicity. The object of the invention is to find new compounds which have excellent fungicidal and insecticidal effects. According to the invention, the object is achieved by providing pesticidal compositions containing as active ingredient compounds of the formula I or their salts, wherein the substituents having the meaning indicated in the description, in addition to suitable formulation auxiliaries. Formula I

Description

Field of application of the invention

The invention relates to pesticides containing as active ingredient new pyrimidine derivatives of formula I below.

Characteristic of the known state of the art

Pyrimidine derivatives having microbicidal properties are already known (see EP-A-139613). The novel pyrimidine derivatives of the formula I show excellent fungicidal and insecticidal effects.

Object of the invention

With the invention pesticides are provided, which are also suitable for controlling animal pests with good plant tolerance and favorable warm-blooded toxicity.

Explanation of the essence of the invention

The object of the invention is to find new compounds which have excellent fungicidal and insecticidal activities.

The present invention therefore relates to the pyrimidine derivatives of the formula I or their salts Jl

R ₁ and R _{2 are} independently hydrogen; Halogen; cyano; (C ₁ -Cs) -Alkyl; (C ₁ -Cs) -HaIOalkyl; (Ci-CgJ-alkyl which is monosubstituted or disubstituted by nitro, cyano, (C ₁ -C ₄ ) -alkoxy, (dQ) -alkylthio or -N (R ₇ ) (R ₈ ); (C ₃ - C ₈ ) -cycloalkyl which may be substituted by (C ₁ -Q) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -haloalkenyl, (C ₃ -C ₄ ) -alkynyl; _(C3-C4) haloalkynyl; (Cr-Cei-cycloalkenyl is a group-N (R ₇₎ (R _8), (dC ₈₎ alkylthio; (C ₁ -Cs) -alkoxy, (C ₁ -C ₈ I-HaIOaIkOXy; (d-CaJAIkylsulfinyl; (dC ₈₎ alkylsulfonyl; phenyl optionally substituted by halogen, nitro, cyano, (dC ₄₎ alkyl, (C ₁ -C ₄ -alkoxy-I, (d-QJ- alkylthio or (C ₁ -C ₄ J-HaIOaIkYl substituted; or phenoxy, optionally substituted by halogen, NO _2, (dC ₄₎ alkyl, (C ₁ -C ₄ J-HaIOaIkYl or (C ₁ -Q) -alkoxy is substituted;

R _{3 is} hydrogen; Halogen; cyano; nitro; (C ₁ -C ₈ -alkyl) (C ₁ -C ₈ -alkyl) (C ₂ -Q) -alkenyl; (C ₁ -C -J-haloalkenyl; phenyl optionally substituted by halogen, nitro, cyano, (C ₁ -Q) -alkyl, (C ₁ -C ₄ J -alkoxy, (C ₁ -C ₄ J-AIkYItIIiO or (C ₁ -C ₄ I-HaIOaIkYl substituted or phenoxy which is optionally substituted by halogen, NO _2, (C ₁ -Q) -alkyl, (d -QJ-haloalkyl or (C ₁ -C ₄ ) -alkoxy; R _{4 is} hydrogen; halogen; (C ₁ -C ₄ -alkoxy; (C ₁ -C ₄ -alkyl) (C ₁ -C ₄ ) -alkyl; a group N (Ry) (Ra) or phenoxy which may be substituted by halogen;

R _{5 is} (d -QJ-alkyl, (d-Ca-alkoxycarbonyl), (Ci-Q-alkenyloxy) carbonyl, -CO ₂ H; (Qr-Q-alkynyloxyjcarbonyl; (C ₁ -C ₄ -haloalkoxy ₎ -carbonyl; (C ₂ -Q-haloalkenyloxy) carbonyl; (Cs-Q-haloalkynyloxyjcarbonyl; -CON (R ₇ ) (R ₈ ); (dQ-alkylcarbonyl; (C ₂ -Q-alkenyl) carbonyl; (Cs-Q-alkynyl-1-carbonyl; Qr-Q-haloalkyl-carbonyl; (C ₂ -Q-haloalkenyl) -carbonyl; (Qa-Q-haloalkynyl-carbonyl; cyano, nitro; S (O) _n R ₉ ; S (O) _n OR ₉ or S (O) _n N (R ₇ ) (R ₈ ); halogen; (C ₁ -C ₄ ) haloalkoxy; (C ₁ -C ₄ -haloalkyl) formyl;

η is one of the numbers 0,1 or 2;

R _{6 is} NO ₂ or CF ₃ ;

R ₇ and R _{8 are} independently hydrogen; (d -QJ-alkyl; (Cy-CyJ-cycloalkyl, which may be substituted by (d-QJ-alkyl) or phenyl which is represented by halogen, (dQ) -alkyl, (dC ₄ ) -haloalkyl, (C ₁ -) Q) -alkoxy, (dQ) -alkylthio, nitro or cyano may be substituted;

R _{9 is} (d -QJ-alkyl; (Cr-QJ-alkenyl, (Cr-Ql-alkynyl or (C ₃ -C ₇ J-CyClOalkyl) which may be substituted by (dQ) -alkyl; R _{10 is} independently hydrogen; (C ₁ -C ₄ ) -alkyl (C; r C ₇ ) -cycloalkyl which may be substituted by (C ₁ -C ₄ ) -alkyl, (dQ-alkoxy-carbonyl; (dQ-alkyl-carbonyl; (C ₁ -C ₄ Phenyl, which may be optionally substituted by halogen, nitro, cyano, (C ₁ -Q) -alkyl, (C ₁ -C ₄ ) -alkoxy, (dQ) -alkylthio or (dQ) -haloalkyl, and X represents one of the groups -NR ₁₀ -NRi ₀ , -NR ₁₀ -or-O-, with the proviso that those compounds of the formula I in which X represents a group -NR ₁₀ - and R _{5 is} CF ₃ or NO ₂ , with exception of.

Suitable salts are, in particular, the salts which can be used in agriculture, for example alkali metal, alkaline earth metal, ammonium or substituted ammonium salts. The salt formation can take place on the group X = -NR ₁₀ -or-NR ₁₀ NH-or in the case of R ₅ = COOH. The salts are prepared by conventional methods from the compounds of formula I.

Halogen is in particular fluorine, chlorine or bromine.

The prefix "halo" in the term of a substituent here and in the following means that this substituent may be mono- or polysubstituted by identical or different meanings The prefix halo includes fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine, bromine Examples of haloalkyl are: CF ₃ , CHF ₂ , CH ₂ F, CCI ₃ , CHCl ₂ , CH ₂ Cl, CBr ₃ , CF ₂ Cl, CCIF ₂ , CF ₂ CHF ₂ , CF ₂ CF ₃ , CF ₂ CHFCF ₃ , CF ₂ CHCIF, CF ₂ CHCl ₂ , CCI ₂ CCI ₃ , nC ₃ F ₇ , -CH (CF ₃ I ₂ , n -QF ₉ , n-Cg-F ,,, nC ₆ F ₁₃ ', nC ₇ F _1B and nC ₈ F ₁₇ .

Examples of haloalkoxy are: OCF ₃ , OCHF ₂ , OCF ₂ CHF ₂ , OCF ₂ CHFCF ₃ , OCF ₂ Cl, OCF ₂ CF ₂ CF ₃ , OCF ₂ CHFCI and OCF ₂ CF ₂ CF ₂ CF ₃ .

Examples which may be mentioned of (Cr-Q 1 -haloalkenyl are: CH ₂ = CF-; F ₂ C =CF-; CI ₂ C =CCI-Preferred compounds of the formula I as defined above are those in which R _{1 is} independently hydrogen; Halogen; cyano; (C ₁ -Cs) -alkyl (dC ₈ ) -haloalkyl; (C ₁ -Cs) -alkyl which may be mono- or disubstituted by (C ₁ -C ₄ ) -alkoxy or (C ₁ -C ₄₎ alkylthio substituted (C ₃ -C ₈ J-CyClOaIkYl by (dC ₈₎ may be substituted alkyl; (dC ₈₎ alkylthio; (C ₁ -Ca) -alkoxy, (C ₁ -C ₈ ) -alkylsulfinyl; (C ₁ -C 6) -alkyl-sulfonyl; phenyl which is optionally monosubstituted or polysubstituted by halogen and / or mono- or trisubstituted by nitro, cyano, (C ₁ -C ₄ -arylalkyl, (C ₁ -C _{4 )} -alkyl J-AIkOXy or (d-QJ-haloalkyl is substituted, R _{2 is} the meaning of R ₁ except optionally substituted phenyl,

R _{3 is} hydrogen; Halogen; cyano; nitro; (C ₁ -C ₈ -alkyl-J, (C ₁ -C ₈ J-HaIOaIkYl or phenoxy which is optionally monosubstituted to trisubstituted by halogen NO _2, (dQ) alkyl, (C ^ QJ-haloalkyl or (C ₁ - C ₄ J-alkoxy is substituted; R _{4 is} hydrogen; halogen; (C ₁ -C ₄ ) -alkoxy;

R _{5 is} (C ₁ -Q) -alkyl, (dQ-alkoxy) carbonyl, -CO ₂ H; -CON (R ₇ ) (R ₈ ); (dQ-alkylcarbonyl; (Cy-Q-haloalkylcarbonyl; cyano, halo, nitro or S (O) _n N (R ₇ ) (R ₈ );

η is one of the numbers 0,1 or 2;

R _{6 is} NO ₂ or CF ₃ ;

R ₇ and R _{8 are} independently hydrogen; (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₇ ) -cycloalkyl which may be substituted by (C ₁ -Q) -alkyl, or phenyl which is monosubstituted to trisubstituted by halogen, (C ₁ -Q) -Alkoxy, R _{10 can} independently be hydrogen; (C ₁ -C ₄ -alkyl);

Signify-O- or - X one of the groups -NR ₁₀ -NR ₁₀ - or-NR _{10 degrees.}

Particularly preferred of these are compounds of the formula I in which

R ₁ (dC ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkyl (C ₃ -C ₆ -cycloalkyl), phenyl or phenyl which is substituted as indicated above,

in particular (dC _a ) -haloalkyl, R ₂ H or (dQ) -alkyl, R ₃ H or halogen, R ₄ H or halogen,

R _{5 is} (C ₁ -C ₄ -alkoxyCaTbOnYl, cyano, (C ₁ -C ₄ -haloalkyl, (C ₁ -C ₄ ) -haloalkyl or chloro, and R _{6 is} NO ₂ and X is NH or -O-.

The present invention also provides processes for the preparation of the compounds of the formula I, which comprises reacting a compound of the formula II in the presence of a base

(ID

with a compound of formula III.

The substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ have the meaning as in the formula I. V and W are halogen, hydroxy, a group NR ₁₀ NHR ₁₀ or a group NHR _{10 /} wherein must mean for the case where W is halogen, V is hydroxy, a group-NR ₁₀ -NHR ₁₀ or a group NHR _10, and for the case where V is halogen, W is hydroxy, a group-NR ₁₀ NHR ₁₀ or a group NHR must mean ₁₀ . The radical R ₁₀ has the meaning given in formula I. The term halogen represents

Fluorine, chlorine, bromine and iodine, especially chlorine and bromine. _i

The reaction of the compounds II with III is preferably carried out in inert aprotic solvents such as acetonitrile, dichloromethane, toluene, xylene, tetrahydrofuran, dioxane, diaryl ethers such as diethylene glycol dialkyl, in particular diethylene glycol diethyl ether, or DMF at temperatures between -10 ^c C and the boiling temperature of the solvent , Suitable bases are the bases customary for this type of reaction, such as, for example, carbonates and bicarbonates of alkali metals and alkaline earth metals, alkali metal hydroxides, alkali metal alkoxides such as K-tert-butylate, tertiary amines, pyridine or substituted pyridine bases

(eg 4-dimethylaminopyridine).

A second equivalent of the compounds of general formula II can also take over the function of the base.

Suitable bases are then only those compounds of the formulas II in which V represents a group NR ₁₀ NR ₁₀ or a group NHR ₁₀ .

The reaction takes place both in aprotic solvents ₍ such as, for example, acetonitrile, diethylene glycol dimethyl ether, dichloromethane, toluene, tetrahydrofuran, dioxane or DMF and in protic solvents such as, for example, methanol, ethanol or isopropanol in the temperature range from 0 ° to Boiling temperature of the solvent.

The compounds of the formula II can be synthesized by generally known processes (cf., for example, J. Org Chem 26, 4504, US Pat. No. 4,343,805 and Houben-Weyl, Methoden der Organischen Chemie, Volume 10/2, page 252). The compounds of the formula III are known to a large extent and are readily accessible by customary methods (compare Liebig's Annalen der Chemie 366, 93, British Patent 951,770, CA 79,78364x, CA 84 30640k). The compounds of the formula III where W = OH can be prepared from the corresponding compounds in which hydrogen is present instead of the nitro groups by customary nitration reactions. Compounds with W = halogen are obtained by subsequent halogenation. Specific compounds of the formula III where R ₅ = haloalkoxy and their preparation are described in German Patent Application P 3644798.6.

The compounds of the formula I according to the invention are distinguished by an outstanding fungicidal action. Already penetrated into the plant tissue fungal pathogens can successfully fight curative. This is particularly important and beneficial in those fungal diseases that can not be effectively controlled after infection with the usual fungicides. The spectrum of action of the claimed compounds covers a variety of different economically important, phytopathogenic fungi, such. B. Piricularia oryzae, powdery mildew, Fusariumarten, Plasmopora viticola and Pseudoperonospora cubensis. Particularly well benzimidazole and dicarboximide sensitive and resistant Botrytis cinerea strains are detected, and BCM sensitive and resistant Pseudocercosporella herpotrichoides strains.

(BCM = active ingredient carbendazim). -

The compounds of the formula I are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metal working or as preservatives in drilling and cutting oils.

The compounds of the formula I, in particular those of the examples listed below, can also be advantageous with

other known fungicides are combined. ^s

As such combination partners come into consideration the products:

Imazalil, Prochloraz, Fenapanil, SSF105, Triflumizole, PP969, Flutriafol, BAY-MEB 6401, Propiconazole, Etaconazole, Diclobutrazole, Bitertanol, Triadimefon, Triadimenol, Fluotrimazole, Tridemorph, Dodemorph, Fenpropimorph, .Falimorph, S-32165, Chlobenzthiazone, Parinol, Buthiobate, fenpropidin, triforine, fenarimol, nuarimol, triarimole, ethirimol, dimethirimole, bupirimate, rabenzazole, tricyclazole, ofurace, furalaxyl, benalaxyl, metalaxyl, pencyurone, oxadixyl, cyprofuram, dichlomeziri, samplesazoles, fluobenzimines, pyroxyfur, NK-483, PP- 389, pyroquilon, hymexazole, fenitropan, UHF-8227, tolclofosmethyl, ditalimfos, edifenphos, pyrazophos, isoprothiolanes, cymoxanil, dichloranido, captafol, captan, folpet, tolylfluanid, chlorothalonil, etridiazole, iprodione, procymidone, vinclozolin, metomelane, myclozolin, dichlozolinates, Fluoroimides, drazoxolone, quinomethionates, nitrothalisopropyl, dithianone, dinocap, binapacryl, fentinacetates, fentin hydroxides, carboxin, oxycarboxine, pyracarbolide, methfuroxam, fenf uram, Furmecyclox, Benodanil, Mebenil, Mepronil, Flutolanil, Fuberidazole, Thiabendazole, Carbendazim, Benomyl, Thiofanate, Thiofanate-methyl-CGD-94240F, IKF-1216, Mapcozeb, Maneb, Zineb, Nabam, Thiram, Probineb, Prothiocarb, Propamocarb, Dodine, guazatine, diclorane, quintozene, chloroneb, tecnazene, biphenyl, anilazine, 2-phenylphenol, copper compounds such as cupric chloride, oxine-Cu, Cu oxides, sulfur, fosetylaluminum, sodium dodecylbenzenesulfonate, sodium dodecylsulfate, sodium CIS / Cio-alcohol ether sulfonate, sodium cetostearyl phosphate ester, dioctyl sodium sulfosuccinate, sodium isopropylnaphthalenesulfonate, cetyltrimethylammonium chloride, salts of long-chain primary, secondary or tertiary amines, alkyl-propyleneamines, laurylpyridinium bromide, ethoxylated quaternized fatty amines, alkyl-dimethyl-benzyl-ammonium chloride and 1-hydroxyethyl- 2-alkylimidazolih.

The above-mentioned drugs, for which common-names have been given, are for the most part in CH. R. Worthing,

S. B. Walker, Thes Pesticide Manual, 7th Edition (1983), British Crop Protection Council. Connections for which number codes are specified have the following structures

Cl

CH? Il

SS F 105

0 Il

(CH -) - CH-CH-CH ₀ -CC (CH,)

OH NN

PP 969

C (CH ₃ )

H ₅ C ₂ O

C-OCH I

Bay Meb 6401

S - 32165

PP - 389

OH CONH-CH-CCl.

BK - 483

Unexpectedly, the fungicidal action of the drug combinations in many cases is higher than the sum of the effect of the individual components, the so-called Colby forms! is calculated, cf. S. R. Colby, Weeds 15, 20-22 (1967). Thus, the drug combinations show synergistic effects.

The weight ratios of the active substance groups in the active substance combinations can vary in relatively large ranges.

In general, per part by weight of the formula from 10,000 to 10 parts by weight of active compound, preferably from 0.001 to 2.5 parts by weight of the combination partner.

The active compound combinations according to the invention have a strong biocidal action and can therefore be used advantageously for controlling microorganisms, in particular in crop protection. The good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of above-ground parts of plants, planting and seed and the soil.

The active ingredient combinations have a very broad spectrum of activity and can be used against parasitic fungi that attack aboveground plant parts or attack the plants from the ground.

The active compound combinations according to the invention show an excellent action as a seed dressing against phytopathogenic fungi, such as. Tilletia, Urocystis, Ustilago, Septoria, Typhula, Rhynchosporium, Helminthosporium and Fusarium species.

Also as soil control agents can be used to combat phytopathogenic fungi, the root rots and tracheomycosis causing z. As pathogens of the genera Pythium, Verticillium, Phialophora, Rhizoctonia, Fusarium and Thielaviopsis.

In direct application of the drug combinations on the above-ground parts of plants can control a variety of economically important pathogens excellent, such. As true powdery mildews, (Erysiphe, Uncinula, Sphaerotheca-, Podosphaera species, Leveillula taurica), rust fungi, Venturia species, Cercospora species, Alternaria species, Botrytis species, Phytophthora species, Peronospora species, Piricularia oryzae and Pellicularia sasakii.

The compounds of formula I are suitable for good plant tolerance and favorable toxicity to warm-blooded animals also for controlling animal pests, in particular insects, arachnids and nematodes, particularly preferably for controlling insects in agriculture, in forests, in the protection of stored products and on the Hygiene sector occur. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.

The above mentioned pests include:

From the order of Isopoda z. B. Oniscus asellus, Armadillidium vulgaris, Porcellio scaber.

From the order of Diplopoda z. B. Blaniulus guttulatus.

From the order of Chilopoda z. Geophilus carpophagus, Scutigera spp.

From the order of Symphyla e.g. Scutigerella immaculata.

From the order of Thysanura z. B. Lepisma saccharina.

From the order of Collembola z. B. Onychiurus armatus.

Also can be used as control agents for controlling phytopathogenic fungi, the root rots and tracheomycoses causing z. As pathogens of the genera Pythium, Verticillium, Phialophora, Rhizoctonia,

Fusarium and Thielaviopsis.

When the active ingredient combinations are applied directly to the above-ground parts of plants, a large number of economically important pathogens can be excellently controlled, such as e.g. powdery mildew fungi (Erysiphe, Uncinula, Sphaerotheca, Podosphaera, Leveillula taurica), Rotstpilze, Venturia, Cercospora, Alternaria, Botrytis, Phytophthora, Peronospora, Piricularia oryzae and Pellicularia sasakii.

The compounds of formula I are suitable for good plant tolerance and favorable toxicity to warm-blooded animals also for controlling animal pests, in particular insects, arachnids and nematodes, particularly preferably for controlling insects in agriculture, in forests, in the protection of stored products and on the Hygiene sector occur. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.

The above mentioned pests include: - -

From the order of isopods e.g. Oniscus asellus, Armadillidium vulgaris, Porcellio scaber.

From the order of Diplopoda z. B. Blaniulus guttulatus.

From the order of Chilopoda z. Geophilus carpophagus, Scutigera ssp.

From the order of Symphyla z. B. Scutigerella immaculata.

From the order of Thysanura e.g. Lepisma saccharina.

From the order of Collembola z. B. Onychiurus armatus.

From the order of Orthoptera z. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of Dermaptera z. B. Forficula auricularia.

From the order of Isoptera z. B. Reticulitermes ssp.

From the order of Anoplura z. Phylloera vastatrix, Pemphigus ssp., Pediculus humanus corporis, Haematopinus ssp., Linognathus sp.

From the order of Mallophaga z. B. Trichodectes ssp., Damalinea ssp.

From the order of Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.

From the order of Heteroptera z. B. Eurygaster ssp., Dysdercus intermedius, Piesma quadratum, Cimex lectularius, Rhodnius prolixus, Triatoma ssp.

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicornyne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocoiletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctischrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella.

Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of Coleoptera ζ. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp. , Otiorrhynchussulcatus. Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fanniaspp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus Spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratities capitata, Oacus oleae, Tipula paludosa.

From the order of Siphonaptera z. Xenopsylla cheopis, Ceratophyllus spp.

From the order of Arachnida z. B. Scorpio maurus, Latrodectus mactans.

The invention therefore also relates to pesticides which contain the compounds of the formula I in addition to suitable formulation auxiliaries.

Pests here are the above-mentioned microorganisms, in particular fungi, and animal pests, in particular plant pests, to be understood.

The compositions according to the invention can be used as wettable powders, emulsifiable concentrates, sprayable solutions, dusts, mordants, dispersions, granules or microgranules in the customary formulations.

Injectable powders are preparations which are uniformly dispersible in water and which, in addition to the active substance except a diluent or inert substance, also contain wetting agents, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, eg. As sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonate sodium or oleylmethyltaurine acids. Their preparation is carried out in the usual manner, for. B. by grinding and mixing of the components.

Emulsifiable concentrates may, for. B. by dissolving the active ingredient in an organic solvent, for. As butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. In the case of liquid active substances, the solvent content may also be omitted in whole or in part. As emulsifiers can be used, for example:

Arylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusts can be obtained by grinding the active ingredient with finely divided solids, eg. Talc, natural clays such as kaolin, bentonite, poryphillite or diatomaceous earth.

Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of binders, for. As polyvinyl alcohol, polyacrylic acid sodium or mineral oils on the surface of carriers such as sand, kaolinites, or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.

In wettable powders, the active ingredient concentration of both active ingredients is about 10 to 90% by weight; the remainder to 100% by weight consists of conventional formulation ingredients. For emulsifiable concentrates, the active ingredient concentration of both active ingredients may be about 10 to 80% by weight. Dusty formulations usually contain 5 to 20 wt .-% of the active ingredients, sprayable solutions about 1 to 20 wt .-%. In the case of granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used.

In addition, the active substance formulations mentioned optionally contain the usual adhesion, wetting, dispersing, emulsifying, penetrating, solvent, filling or carrier substances.

For use, the concentrates present in commercially available form are optionally diluted in the usual manner, for. B.

for wettable powders, emulsifiable concentrates, dispersions and sometimes also for microgranules by means of water.

Dusty and granulated preparations and sprayable solutions are usually no longer diluted with other inert substances before use.

The application rates of the active compounds of the formula I can vary within wide limits and are generally between 0.010 and 5 kg / ha.

The following examples serve to illustrate the invention.

Exemplary embodiments A. Formulation examples Examples A:

A dust is obtained by

10 parts by weight of active ingredient and 90 parts by weight of talc as inert substance

mixed and crushed in a hammer mill.

Examples:

A readily dispersible in water, wettable powder is obtained by

25 parts by weight of active ingredient

64 parts by weight of kaolin-containing quartz as inert substance 10 parts by weight of lignosuccinic acid potassium and 1 part by weight of sodium oleylmethyltaurine as wetting and dispersing agent

mixed and ground in a pin mill.

Examples:

A water-dispersible dispersion concentrate is obtained by reacting

20 parts by weight of active ingredient

6 parts by weight of alkylphenol polyglycol ether (Triton X207)

3 parts by weight Isotridecanolpolyglykoläther (8AeO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 ⁰ C to about 377 ° C)

mixed and ground in a ball mill to a fineness of less than 5 microns.

Example D:

An emulsifiable concentrate is obtained

15 parts by weight of active compound 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol (10 AeO) as emulsifier

B. Chemical Examples

Example (1.32)

4- (5-chloro-2-trichloromethyl-4-pyrimidinylamino) -3,5-dinitro-benzonitrile

5.15 g (0.092 mol) of KOH powder were added at -5 ° C. to a solution of 4.45 g (0.018 mol) of 5-chloro-2-trichloromethyl-4-pyrimidyl-amine in 130 ml of abs. Then added dropwise a solution of 4.10 g (0.018 mol) of 4-chloro-3,5-dinitrobenzonitrile in 30rril absolute THF so that the temperature did not rise above 0 ⁰ C. After stirring for eight hours, the solid components were filtered off with suction and the solvent was evaporated in vacuo. The residue was taken up in H ₂ O and acidified with dilute hydrochloric acid. It was then extracted with chloroform, dried over MgSO ₄ , evaporated in vacuo, and the resulting solid recrystallized from diisopropyl ether

 Mp 214-215 ° C

Example 2.10 Potassium 5-chloro-N- (2,6-dinitro-4-ethoxycarbonyl-phenyl) -2- (1,1,2,2-tetrafluoroethyl) -4-pyrimidinyl-aminate To a 9.18 g solution (0.04 mol) of 5-chloro-2- (1,1,2,2-tetrafluoroethyl) -4-pyrimidinyl-amine in 200 ml of absolute THF was added at -5 ° C 4.48 g (0.08 mol) of KOH powder , Thereafter, a solution of 10.98 g (0.04 mol) of ethyl ^ -chloro-S ^ -dinitrobenzoatin in 100 ml of absolute THF was added dropwise so that the temperature did not rise above 0 ⁰ C. The mixture was stirred for 3 h at 0 ⁰ C and then allowed the reaction mixture within 2 h to warm to room temperature. The solid components were then filtered off with suction and the mother liquor was evaporated. The solid residue was recrystallized from ethyl acetate. M.p. 257-260 ⁰ C

Example 3.26 4- (2,6-Dinitro-4-trifluoromethyl-phenoxy) -5-methyl-2-perfluoroethyl-pyrimidine To a suspension of 3.3 g of K ₂ CO ₃ in 50 ml of acetonitrile was added dropwise successively a solution of 4.5 g (0.16 mol) of 4-chloro-3,5-dinitro-benzotrifluoride and 3.8 g (0.16 mol) of 5-methyl-2-perfluoroethyl-4-pyrimidinol. The mixture was heated to reflux for 3 h, the precipitate was filtered off with suction and the solution was evaporated in vacuo. The residue was recrystallized from diisopropyl acrylate. M.p. 90-92 ° C.

Example 4.167 N '- (2,6-Dinitro-4-trifluoromethyl-phenyl) -5-methyl-2-perfluoroethyl-4-pyimidinyl-hydrazine To a solution of 2.7 g (0.01 mol) of 4-chloro-3 , 5-dinitrobenzotrifluoride in 80 ml of EtOH, 4.84 g (0.02 mol) of 5-methyl-2-perfluoroethyl-4-pyrimidinylhydrazine dissolved in 30 ml of EtOH were added dropwise within 30 minutes.

The mixture was then allowed to reflux for 5 h and then the solvent was evaporated in vacuo. The residue was taken up in water and extracted with chloroform. The organic phase was dried with Na ₂ SO ₄ and evaporated in vacuo. The resulting solid was recrystallized from diisopropyl ether.

M.p. 135-137 ⁰ C. - ·

Example 5.16 N '- {2,6-Dinitro-4-trifluoromethyl-phenyl) -6, N-dimethyl-2-trichloromethyl-4-pyrimidinyl-hydrazine. To a solution of 2.7 g (0.01 mol) of 4- Chloro-3,5-dinitrobenzotrifluoride in EtOH was added dropwise 5.1 g (0.02 mol) of N-methyl-N- (6-methyl-2-trichloromethyl-4-pyrimidinyl) hydrazine dissolved in 30 ml of EtOH within 30 minutes added. The mixture was allowed to reflux for 5 hours and then evaporated to dryness. The residue was dissolved in chloroform, washed with water, dried over Na ₂ SO ₄ and evaporated in vacuo. The precipitated solid was recrystallized from diisopropyl ether

 Mp. 160-163 ° C

Analogously to Example 1, the compounds of Table 1, analogously to Example 2, the compounds of Table 2, analogously to Example 3, the compounds of Table 3 analogously to Example 4, the compounds of Table 4 and analogously to Example 5, the compounds of Table 5 produce.

Table 1

No. R RRRR

1 2 3 4 5

physics.

R constants ⁶ Γ ⁰ Ci

1.1 CCI 1.2 CCI 1.3 CCI 1.4 CCI 1.5 CCI 1.6 CCI 1.7 CCI 1.8 CCI 1.9 CCI 1.10 CCI 1.11 CCI 1.12 CCI 1.13 CCI 1.14 CCI

H  j H H C = N H H H j CH WWW HH Cl CO Et 2 CH 3 CO Et H  J O H H CCI J CH t H H CCI J CH H Cl CCI CH H H C = N 3 CH H Cl CsN. 3 CH 3 H H CO et CH 3 H Cl CO Et 2 CH 3 H H CH H Cl SO ₂ NCT H H

NO, Mp. 157-160

NO Mp. 121-124

NO Smp. 132-134

NO syrup

NO

2 NO

Mp. 180-183

Mp. 111-114

Mp. 111-115

NO

1.15 CCI CH 3 H Cl SO ₂ N ^ 1.16 CH H H H CsN 1.17 CH H H H CCl • a 1.18 1.19 3 CH 3 CH H H H H H H i CH 3 CO Et 1.20 CF CHF 2 2 H H H CCI 1.21 CF CHF 2 2 H H Cl CCI 1.22 CF CHF 2 2 H H H C = N 1.23 CF CHF 2 2 H H H CO et 1.24 CF CHF 2 2 H H Cl CO et 2

NO

NO-2

NO 2

NO

NO

2 NO

2 NO

2 NO

2 NO

2 NO

Mp. 168-170 m. 156-157

Table 1 (continued)

No. R R RR R

1 2 3 4 5

physijc. R constants

⁶ f ^o c1

1. 25 CF CHF 2 2 H H H CH 2 1. 26 CF H H H C = N 1. 27 CF 2 H H H CO et 2 1. 28 CF H H H CCl 2 1. 29 3 CF 2 H - H H CH 3 1. 30 CF ₂ CHF ₂ CH ₃ , H H CO et 2 1. 31 CCI H Cl H CO Et ₌ 2 1. 32 CCl 3 H Cl H C = N 1. 33 CCI H Cl Cl CCl 2 1. 34 CCl 2 H Cl H CCl 3 CH 1. 1. 35 36 CCl 3 CCl H H Cl Cl Cl H ä CH 1. 37 CCI H Cl Cl CO CH ₃ 1. 38 CF ₂ CHF ₂ CH ₃ H H CO et 2 1. 39 CCI H Cl Cl CCI 1. 40 3 CF a H Cl H CFCl 1. 41 J CF'S H Cl Cl CF CHF 2 2 1. 42 »3 CF H Cl H CF CClF 1. 43 CF 2 H Cl F ΔZl, CCl2 1. 44 CF CHF 2 2 H Cl H CCI 1. 45 CF CHF H Cl Cl C = N 1. 46 CF CHF 2 2 H egg H C = N 1. 47 CF CHF 2 2 H Cl Cl CO et 2 1. 48 CF CHF 2 2 H Cl H CO et 1. 49 CF CHF 2 2 H Cl Cl CClF 2 1. 50 CF CHF 2 2 H Cl H CClF 2 1. 51 CF CHF H Cl Cl 3CCl 3 1. 1. 52, 53 • - Λ 4b CF CHF 2 2 CCl 3 H Cl Cl Cl Cl H

NO 2

NO 2

NO 2

NO 2

NO 2

NO 2

NO sirp. 127-131

NO Smp.214-215

NO

2 NO

2 NO

2 'NO

2 NO

2 NO Mp. 167-131

NO

2 NO

2 NO

2 NO

2 NO

2 NO Mp. 67-68

NO

2 NO Mp. 193-196

NO 2

NO. Mp. J.09-110

NO panties. 115-118

CF

CF 3

NO

1 (continued) R R 2 R 3 R 4 ^R 5 -11- 263 220 physics. table CCl 2 Cl Cl Cl CO et «5 R constants ⁶ r ° ci CCl 2 Cl Cl H ΔC = N NO 2 '" No. CCl 2 Cl Cl Cl CH 2 NO 2 NO 2 NO «5 1:54 CCI CH 2 Cl H CCl 2 Δ, NO 2 1:55 CCl 2 CH egg F CCI NO 2 1:56 CCl 2 CH • 3 Cl Cl ο C = N NO mp 198-201 2 ^ι 1:57 CCl 2 O CH • a Cl H C = N NO 2 1:58 CF CHF ο o w Cl Cl H · CH NO 1:59 Δ Δ CF CHF 2 2 Cl Cl Cl 3 C = N CF 1.60 CH CH Cl H C = N 3 CF 1.61 3 CH ό CH Cl Cl C = N ύ NO ο. 1.62 C = N Ή Cl H C = N Δ NO 2 1.63 C = N H Cl H CO et 2 NO 1.64 C = N H Cl H CCl 2 NO 2 1.65 C = N H Cl H CH, 2 NO 1.66 'CF CF O' S H Cl H C = N Δ NO 2 1.67 Δ Ο CF CF 2 3 CH 3 Cl Cl C = N NO 2 1.68 CF CF 2 3 CH Cl H ! ^ CH ₃ ⁵⁰ 2 ^N C ^ s NO  1.69 CF CF 2 2 ClCH 2 Cl H CCI Δ NO 2 1.70 CF Cl 2 H Cl Cl CCI NO 2 1.71 CF Cl 2 H Cl H 3 CH "S NO 1.72 CClF 2 H Cl H J CH NO 2 1.73 CCIF CH Cl Cl 3 Et NO 2 1.74 CH 3 H egg H CF Cl NO l; 75 3 CH H Cl Cl ΔC = N Δ NO 1.76 CH Cl Cl Cl CO et NO 2 1.77 3 Et H Cl Cl ΔC = N NO 1.78 et H Cl H C = N NO 9 1.79 < H Cl H CCI 1.80 1.81 1.82

• ^R i R 2 R 3 R 4 R 5 -12- physics. 263 220 83 - <3 H Cl H CHN R constants ⁶ F ⁰ CI 84 OEt Cl Cl F CCl CCl NO 85 OEt OEt Cl F CCl CCl 2 3 2 CF Ί Table 1 (continued) 86 SCH 87 _O- / q \ -P Cl SCH 3 Cl Cl Cl F H CCl = CCl 2 CF CHF 2 2 ό CF 88 _7 ^ \ _ _C1 H Cl H CO et 2 NO 2 NO 2 No 89 cl Cl Cl Cl CCl 3 NO 2 1. 90 f H Cl Cl CCI NO 2 1. 91N (CH) 3 2 CCl » Cl H CHCl 2 NO 2 1. 92CCl H br H CCl 3 NO 2 1. 1. 93 CCl 3 H br H CO et NO Mp. 220-22 1. 94 CCl 3 H br egg ΔCH ₅ CCl 3 CH 3 CFCl <5 NO 1. 95 CCl 96 CCl ³ 3 97 CF CHF 2 2 98 CF CHF 2 2 H H H H Br- Br Br Br H Cl H H Δ CHOC NO 2 1. 99 CF CF 2 3 H br Cl δ ο CF CF NO mp 153-154 NO ² 2 NO 2 NO 2 1. 100 CF CF 2 3 H br H ΔJ CO Et 2 NO 2 1. 101 CH 3 H br H CCI NO 2 1. 102 CH H br Cl _ 3 NO Mp. 122-125 1. 103 CH H br H C = N NO 2 1. 1. 1. 1. 104 - ^ H br H C = N NO 2 1. 105 C H 2 5 H br Cl CO Et 2 C = N NO 2 1. 106 CF 3 7 107 C ₃ F ₇ H H Br Br F F CCI NO 2 1. 108 C = TSI H br J CO et 2 NO 2 NO 2 1. 109 CCl3 H C = N H CO et NO 2 1. 110 CCl 3 H C = N Cl Δ NO 2 1. 111 CCl H C = N H NO 2 1. NO 1. 1. 1. 1. 1. 1.

Table 1 (continued)

physics.

No • R • 1 R 2 R 3 R 4 R R constants r ° ci 1. 112 CCI H C = N H CCI NO 2 1. 1. 113 114 CCl 3 CH 3 CH 3 CH 3 CH • a H H C = N H H CH _3 NO 2 NO 2 1. 115 j CH "3 H C = N H CO Et 2 CCl • J NO 2 1. 116 • 3 CH 3 H CSN H J CH NO 1. 117 H CSN H CO et 2 NO 2 1. 118 -4 H CSN Cl CCl 3 CCl 2 NO 2 1. 1. 119 120 -4 CF CHF 2 2 H H C = N Cl H CCI NO 2 NO 1. 121 CF CHF 2 2 H C = N Cl CO Et '2 CO Et O NO 1. 1. 122 123 CF CHF 2 2 H H TZ H Cl Ji CH _3 NO 2 NO 2 1. 1. 124 125 CF CHF 2 2 H H C = N CSN H H CO et 2 NO 2 NO Mp. 188-190 1. 126 CF CHF 2 2 H C = N H CO H 2 NO 1. 127 CF CHF H CSN H CO H 2 - CF 2 1. 128 Cl H CSN Cl CCl • a NO 2 1. 129 CCl 2 H CSN H «3 CH NO 2 1. 130 CCl 2 H C = N H CCI NO 2 1. 131 CCI H C = N H CSN NO 2 1. 132 CCI H CH H CCl 2 NO 2 1. 133 CCI H CH Cl CCI NO 2 1. 134 3 CF H 3 CH H -Oo Et NO 1. 135 CF 2 H J CH H CH «a NO 1. 136 CF CHF 2 2 H CH H CSN NO 2 1. 137 CF CHF 2 2 H 3 CH H CO et 2 NO 2 1. 138 CF CHF 2 2 CF CHF 2 2 H CH H CsN NO 2 1. 139 H CH 2 H , CO et 2 NO Smv. 178-17 2 " 1. 140 H CH H CCl CH 3 NO Mp. 82-83 1. 1. .141 142 H H CH 3 CH 3 H H NO 2 NO 2

Table 1 (Port setting) no.

^l 2 ^R 3

physics. Constants rci

1 .1 1 .1 43 44 CP ₂ CP ₅ CP ₂ CP ₅ H H CH ₅ CH ₅ H H ChN. CO ₂ Et 1 .1 45 CH ₅ H CH ₅ H CCl ₅ 1 .1 46 et H CH ₅ H ChN 1 .1 47 ChN H CH ₅ H CCl ₅ 1 .1 48 ChN H CH ₅ H CO ₂ Et 1 .1 1 .1 1 .1 49 50 51 OCH ₅ OEt SCH ₅ Ω Ω Ω WWW VjJ VjJ Vj) CH ₅ CH ₅ CH ₅ H Cl Cl CCl ₅ C = N CHN 1.1 1 .1 52 53 0- (O) -Cl CCl ₅ CH ₅ H CH ₅ P Cl H ChN ChN 1 .1 54 CP ₂ CHP ₂ H P Cl CO ₂ CH ₅ 1 .1 55 CHCl ₂ H OCH ₅ P CHP ₂ 1 .1 1.1 56 57 CP ₅ CCl = CCl ₂ H H CP ₅ CCl, H H CCl ₅ CH, 1 .1 58 CP = CP ₂ H CP = CP ₂ H 0 Il S-OMe U 0 1 .1 59 CH ₅ CH ₅ CH ₂ Cl Cl H ChN 1 .1 60 CH, H o ^ ö) - Cl H CHN Cl 1 .1 61 CH ₅ H -o? ö \ Cl CO ₂ Et 1 .1 62 CH ₅ H -o ^ ö) - Cl H CO ₂ Me 1 .1 63 CCi ₅ H -0- (O) - NO ₂ H CO ₂ Bu 1 .1 64 CCl ₅ H Cl -o-? Ö) Cl CO ₂ Et

1,165 CCl-ζ

H CCl

NO, NO, NO, NO, NO, NO, NO, NO, NO

NO, NO, NO, NO, NO, NO,

NO,

NO,

NO,

NO,

NO,

NO,

NO,

NO,

^R 1 H ^R 3 ^R 4 CO ₂ H physics. -15- 263 220 H CO ₂ H Rg constants CF ₂ CHF ₂ H Cl H CO ₂ H pci CCl ₃ H Cl H CO ₂ H NO ₂ Mp. 244-247 Table 1 (continued) CCl _{3 v} H CN H CO ₂ H NO ₂ CF ₂ CHF ₂ H CN H CO ₂ H NO ₂ No. CF ₂ CHF ₂ H br H CO ₂ H NO ₂ CF ₂ CHF ₂ H CH ₃ H CO ₂ H NO ₂ 1166 CCl ₃ H br H CO ₂ H NO ₂ 1167 CF ₃ H Cl H CO ₂ H NO ₂ 1168 CF ₃ H br H CO ₂ H NO ₂ 1169 CF ₃ H CN H . CO ₂ H NO ₂ 1170 CF ₂ Cl H Cl H CO ₂ H NO ₂ 1171 CF ₂ Cl H br H C = N NO ₂ 1172 CF ₂ Cl H C = U H CO ₂ Bu NO ₂ 1173 CF ₃ H Cl H CF ₂ Cl NO ₂ 1174 F ₂ C = CF Cl br Cl CClCF ₂ NO ₂ Mp. 230-232 1175 Cl ₂ C = CCl H Cl H CO ₂ H NO ₂ 1176 F ₂ C = CCl H Cl H C = N NO ₂ 1177 C = N Cl Cl H 1 CO ₂ Pr NO ₂ · 1178 CCl ₃ F Cl OEt CH ₃ NO ₂ 1179 CClF ₂ H 0- <£> C NO ₂ 1180 CH ₂ CH ₃ HN (CH ₃ J ₂ NO ₂ 1181 NO ₂ 1182 1183 1184 1185 1186

Table 1 (continued)

No. V "2 * 3 ^R 4 * 5 ^R 6 physics. Constants L ⁰ CJ 1,187,188 CF ₂ Cl CF ₂ Cl H H H H H H CO ₂ Et C = N NO ₂ NO ₂ 1189 CF ₂ Cl H Cl H C = N NO ₂ Snp. 250-252 1190. CF ₂ Cl H Cl H CO ₂ Et NO ₂ 'Mp. 117-118 1191 CF ₂ Cl H br H C = N NO ₂ Snp. 254-256 1192 CF ₂ Cl H br H CO ₂ Et NO ₂ Snp. 136-137 1193 CF ₂ Cl H , br H Cl NO ₂ 1194 CF ₂ Cl H C = N H C = N ^N0 2 Snp. 217-219 1195 CF ₂ Cl H CSN H CO ₂ Et NO ₂ Snp. 169-170 1196 CF ₂ CHClF H Cl H C = N NO ₂ Snp. 187-188 1197 CF ₂ CHClF H Cl H CO ₂ Et NO ₂ Snp. 100-101 1198 ^nK ¥ V H H H C = N NO ₂ 1199 H ^ ₃ F ₇ H H H CO ₂ Et NO ₂ 1200 H ^ ₃ F ₇ H Cl H CO ₂ Et NO ₂ Snp. 114-115 1201 nC ₃ F ₇ H Cl H C = N NO ₂ Snp. 124-126 1202 ⁿ ^ 3 ^F 7 H br H C = N NO ₂ 1203 H br H CO ₂ Et NO ₂ 1204 CF ₃ H Cl H C = N NO ₂ Snp. 231-232 1205 CF ₂ CHF ₂ H H Cl C = N NO ₂ 1206 CF ₂ CHF ₂ H H H CO ₂ CH ₃ NO ₂ 1207 CF ₂ CHF ₂ H H H CO ₂ Bu NO ₉ 1208 CF ₂ CHF ₂ H H H CON (CHO ₉ NO ₂ Sirp. 241-243 1209 CF ₂ CHF ₂ H Cl H Cl NO ₂ Snp. 110-112 1210 CF ₂ CHF ₂ H Cl H CO ₂ H NO ₂ Slip. 247-249 1211 CF ₂ CHF ₂ H Cl H CO ₂ Bu NO ₂ Slip. 94-97 1212 CF ₂ CHF ₂ H Cl H CH ₃ NO ₂ 1213 CF ₂ CHF ₂ H Cl ' H CO ₂ CH ₃ NO ₂ Sirp. 110-112 1214 CF ₂ CHF ₂ H br H CO ₂ Et NO ₂ Snp. 126-128 1215 CF ₂ CHF ₂ H br H C = N NO ₂ , Snp. 211-213 1216 CF ₂ CHF ₂ H br Cl CO ₂ Et NO ₂ 1217 CF ₂ CHF ₂ H br Cl C = N NO ₂ 1,218 1,219 CF ₂ CHF ₂ CF ₂ CHF ₂ H H Br Br H H CO ₂ CH ₃ CO ₂ Bu NO ₂ NO ₂ 1220 CF ₂ CHF ₂ H CH ₃ - Cl CO ₂ Et NO ₂

Table 1 (continued)

* 3 physics

Constants f ° Cj

1221 CF ₂ CHF ₂ H 1222 CF ₂ CHF ₂ Cl 1223 CF ₂ CHF ₂ Cl 1224 CF ₂ CHF ₂ Cl 1.2 25 CF ₂ CHF ₂ Cl 1226 CF ₂ CF ₃ H 1227 CF ₂ CF ₃ H 1228 CF ₂ CF ₃ H 1229 CF ₂ CF ₃ H 1230 CF ₂ CF ₃ H 1231 CF ₂ CF ₃ H 1232 CFJZF- H 1233 CF ₂ CF ₃ H 1234 CF ₂ CF ₃ H 1235 H 1236 CF ₂ CF ₃ H 1237 CF ₇ CF ₃ H 1238 CF ₂ CF ₃ H 1239 CF ₂ CF ₃ H 1240 CF ₂ CF ₃ H 1241 CF ₂ CF ₃ H 1242 CF ₂ CF ₃ H 1,243 CF ₂ CF ₃ H 1,244 ^CF 2 ^CF 3 H 1245 CF ₂ CF ₃ H 1246 CF ₂ CF ₃ H 1247 CF ₃ CF ₃ H 1248 CF ₂ CF ₃ H 1249 CCl ₃ H 1250 CCl ₃ H 1251 CCl ₃ " H 1252 CCl ₃ - H 1253 CCU H

CH ₃ Cl C = N NO ₂ H H C = N NO ₂ H H CO ₂ Et NO ₂ H H CH ₃ · NO ₂ H H Cl NO ₂ H ' H C = N NO ₂ H Cl C = N ^Ν0 2 H H CO ₂ Et NO ₂ H Cl CO ₂ Et. NO ₂ H H CO ₂ CH ₃ NO ₂ H. H CO ₂ Bu NO ₂ H H .CH ₃ NO ₂ Cl H C = N NO ₂ Cl Cl H Cl CO ₂ Et C = N NO ₂ NO ₂ Cl Cl CO ₂ Et NO ₂ Cl H CO ₂ CH ₃ NO ₂ Cl, H CO ₂ Bu NO ₂ Cl H CH ₃ NO ₂ Cl , H JZL NO ₂ H H Cl NO ₂ br H CO ₂ Et NO ₂ br H CO ₂ CH ₃ NO ₂ br H C = N NO ₂ br Cl CO ₂ Et NO ₂ br H CON (Et) ₂ NO ₂ br H CON (CH ₃ ), 2 ^ΝΟ 2 br H Cl NO ₂ Cl H CCN (Et) ₂ NO ₂ br H CO ₂ Et NO ₂ br H Cl NO ₂ br Cl C = N NO ₂ CH ₃ Cl CO ₂ Et NO ₂

Snp. 112-114 Snp. 90-92

Snp. 126-127 Snp. 146-49

Table 1 (continued)

^R 1 physics. Constants C ⁰ CJ

1,254 1,255 1,256 1,257 1,258 1,259 1,260 1,261 1,262 1,263 1,264 1,265 1,266 1,267 1,268 1,269 1,270 1,271 1,272 1,273 1,274 1,275 1,276 1,277 1,278 1,279 1,280 1,281 1,282 1,283 1,284 1,285 1,286

CCl, _CCl3

CCl ₃ CCl ₁ CCl ₃ CCl ₃ CCl, CCl ₁ CCl, CCl ₃

CCl ₃

CCl ₃

CCl ₃

CH ₃ "CH ₃ CH ₃

CH ₃ DD DD

D-D-D-D-D

CCl, CCl! CCI.

H CH ₃ Cl C = N CH ₃ H Cl CO ₂ H CH ₃ H H CO ₂ CH ₃ CH ₃ H H CONH ₂ Cl Cl H CO ₂ Et Cl Cl Cl C = N CH ₃ Cl H CO ₂ Et CH ₃ Cl Cl CO ₂ Et CH ₃ Cl H Cl Cl H . H CO ₂ Et Cl H H C = N Cl H H Cl Cl H H CON (Et) Cl br H CO ₂ Et Cl br H C = N CCH ₃ CF ₃ H CO ₂ Et OCH ₃ CF ₃ H C = N OCH ₃ CF ₃ Cl CO ₂ Et CCH ₃ CF ₃ H Cl H H H CO ₂ Et H H Cl C = N H H H Cl H Cl H CO ₂ Et H Cl H C = N H Cl H Cl H br Cl C = N H br H CO ₂ Et H br H CO ₂ CH ₃ H br H Cl H br H CH ₃ H " H H CO ₂ Bu H H Cl C = N H H H CO ₂ CH ₃

NO ₂ Snp. 240-243 NO ₂ Snp. 104-105 NO ₂

NO ₂ Snp. 145-146 NO ₂ NO ₂

NO ₂

NO ₂ Snp. 205-207 NO ₂ Snp. 200-202 NO ₂ Snp. 151-155 NO- Snp. 142-146

NO ₂ NO ₂ NO ₂

NO ₂ NO ₂ NO ₂ NO ₂

NO ₂ Snp. 57-63

1 (continued) * 2 * 3 * 4 CH ₃ ^R 6 -19- 263 220 physics. Constants f ° cj table ^R 1 H H H CCN (Et) ₂ NO ₂ Jnr. CCl ₃ H H H Cl NO ₂ 1287 CCl ₃ H Cl H CO ₂ CH ₃ NO ₂ Sirp. 145-147 1288 CCl ₃ H Cl H CO ₂ Bu NO ₂ Snp. 142-144 1289 CCl ₃ H ~ Cl H Cl NO ₂ SRRP. 127-128 1290 CCl ₃ H C = N H CCN (Et) ₂ NO ₂ 1291 CH ₃ H C ^ N H CO ₂ Bu NO ₂ 1292 CH ₃ H C ^ N Cl CON (CH ₃ ) ₂ NO ₂ 1293 CH ₃ H C ^ N H C ^ N NO ₂ 1294 CH ₃ H C ^ N Cl CO ₂ CH ₃ NO ₂ 1295 CH ₃ H C = N H CO ₂ Et NO ₂ 1296 CH ₃ H Cl H C = N NO ₂ Snp. 159-162 1297 CH ₃ H Cl Cl Cl NO ₂ 1298 CH ₃ H Cl H CO ₂ Et NO ₂ 1.299 - CH ₃ H Cl Cl Cl NO ₂ 1300 CH ₃ H Cl H CO ₂ CH ₃ NO ₂ 1301 CH ₃ H Cl H CH _a NO ₂ Srtp. 159-162 1302 CH ₃ H br H CSN NO ₂ 1303 CH ₃ H br Cl CCNH ₂ NO ₂ 1304 CH ₃ H br H CON (CH ₃ ) ₂ NO ₂ 1305 CH ₃ H br H Cl NO ₂ 1306 CH ₃ H br H CO ₂ Et NO ₂ 1307 CH ₃ " H br H CO ₂ Et NO ₂ 1308 CH ₃ H br Cl CH ₃ NO ₂ 1309 ^ 3 H H H CO ₂ Et NO ₂ 1310 CH ₃ H H Cl Cl NO ₂ 1311 CH ₃ H /H H C = N NO ₂ 1312 CH ₃ H H Cl CHF ₂ NO ₂ 1313 CH ₃ H H H CHF ₂ NO ₂ 1314 CCl ₃ CH ₃ H H CHF ₂ NO ₂ 1315 CCl ₃ H Cl H CHF ₂ NO ₂ 1316 CCl ₃ H br H CHF ₂ NO ₂ 1317 CCl ₃ H   F H CHF. NO ₂ 1318 CCl ₃ H CH. H NO. 1319 CCI. 1320

Table 1 (continued)

No.

^<R 5

,physics. Constants I ⁰ CJ

1,321 1,322 1,323 1,324 1,325 1,326 1,327 1,328 1,329 1,330 1,331 1,332 1,333 1,334 1,335 1,336 1,337 1,338 1,339 1,340 1,341 1,342 1,343 1,344 1,345 1,346 1,347 1,348 1,349 1,350 1,351 1,352 1 ^ 353 1.354

CCl ₃

CCl ₃

CCl ₃

CCl ₃

CF ₂ CE

CF ₂ CHF

CF ₂ CF ₃

CF ₂ CF ₃

CF ₂ CF ₃

CF ₂ CF ₃

CF ₂ CF ₃

CF ₂ CF ₃

CF ₂ CF ₃

CF ₂ CF ₃

CH ₃

CH-,

CF ₂ Cl

CF ₃

CF,

CF,

CF,

CF ₂ CF-

CF ₂ CF.

CCl,

CH.

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

H'

Cl

C = N

egg·

br

Cl

C = N

Cl

Cl

br

Cl

br

Cl

Cl

br

CH ₃

Cl

br

Cl

br

Cl

Cl

br

Cl.

br

Cl

Cl

Cl

Cl

Cl

Oil

CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂ CHF ₂

NO-NO ₂ NO ₂ NO ₂

NO ₂ NO ₂ NO ₂ NO ₂ NO ₂

NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂

NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂

NO ₂

NO ₂ NO ₂

Table 1 (continued)

No. ^R 1 "2 Cl · ; ^R 4. ' "5 ^R 6 •physics. Constants Z ~ ° c_7 .1.355 CCl ₃ H br H CH ₂ F NO ₂ 1356 CCl ₃ H H Cl Br Cl Cl H CH ₂ F NO ₂ 1,357 1,358 i.359 1,360 1,361 CF ₂ CHF ₂ CF ₂ CHF ₂ CF ₂ CHF ₂ CF-CF ₃ CF ₂ CF ₃ ' H H H H H Cl H H H H H Cl CH ₂ F CH ₂ F CH ₂ F CH ₂ F CH ₂ F NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ 1,362 1,363 CF ₂ Cl CCl ₃ H H Cl H H CH ₂ F CF ₂ Cl NO ₂ NO ₂ .1.364 CCl ₃ H br H CF ₂ Cl NO ₂ 1365 CCl ₃ H ' · Cl H ' CF ₂ Cl NO ₂ 1366 CCl ₃ H Cl Cl CF ₂ Cl NO ₂ 1367 CCl ₃ CH ₃ Cl H CF ₂ Cl NO ₂ 1368 CF ₂ CHF ₂ H br H CF ₂ Cl ' NO ₂ 1369 CF ₂ CHF ₂ H H Cl CF ₂ Cl NO ₂ 1370 CF ₂ CHF ₂ H CH ₃ Cl CF ₂ Cl NO ₂ . 1371 CF ₂ CHF ₂ H Cl Cl CF ₂ Cl NO ₂ 1372 CF ₂ CF ₃ H br H CF ₂ Cl NO ₂ 1373 CF ₂ CF ₃ H H H CF ₂ Cl NO ₂ 1375 CF ₂ CF ₃ H C ^ N Cl CF ₂ Cl NO ₂ 1376 CF ₂ CF ₃ H Cl H CF ₂ Cl NO ₂ 1377 CF ₂ Cl H br H CF ₂ Cl NO ₂ 1378 CF ₂ Cl H Cl H CF ₂ Cl NO ₂ 1379 CF ₃ H br H CF ₂ Cl NO ₂ 1380 CF ₃ H Cl H CF ₂ Cl NO ₂ 1381 CF ₃ H br Cl CF ₂ Cl NO ₂ 1382 CF H Cl Cl CF ₂ Cl NO ₂ 1383 CCl ₃ H Cl H CFCl ₂ NO ₂ 1384 CCl ₃ H br Cl CFCl ₂ NO ₂ 1385 CCl ₃ H br H CFCl ₂ NO ₂ 1386 CCl ₃ H H Cl CFCl ₂ NO ₂ 1387 CCl ₃ H H H CFCl ₂ NO ₂ 1388 CCl ₃ CH ₃ H Cl CFCl ₂ NO ₂ 1389 CCI. CF, H CFCl ^ NO-

Table 1 (continued)

No.

physics. constants

1390 CF ₂ CHF ₂ H Cl H CFCl ₂ NO ₂ 1391 CF ₂ CHF ₂ H H H CFCl ₂ NO ₂ 1392 CF CHF- H br H-. CFCl ₂ NO ₂ 1393 CF ₂ CHF ₂ H Cl Cl CFCl ₂ NO ₂ 1394 CF ₂ CHF ₂ H H Cl CFCl ₂ NO ₂ 1395 CF ₂ CHF ₂ H br Cl CFCl ₂ NO ₂ 1396 CF ₂ CHF ₂ CH ₃ Cl Cl CFCl ₂ NO ₂ 1397 CF ₂ CF ₃ H Cl H CFCl ₂ . NO ₂ 1398 CF ₂ CF ₃ H br H CFCl ₂ NO ₂ 1399 CF ₂ CF ₃ H CH ₃ H CFCl ₂ NO ₂ 1400 CF ₂ CF ₃ CH ₃ H H CFCl ₂ NO ₂ 1401 CF ₂ CF ₃ CF ₃ H H . CFCl ₂ NO ₂ 1402 CF ₂ CF ₃ H Cl Cl CFCl ₂ NO ₂ 1403 CF ₂ CF ₃ H H Cl CFCl ₂ NO ₂ 1..404 CF ₂ CF ₃ H C = N H CFCl ₂ NO ₂ 1405 CCl ₃ H Cl H CF ₂ CHF ₂ NO ₂ 1406 CCl ₃ H H H CF ₂ CHF ₂ NO ₂ 1407 CCl ₃ CH ₃ Cl H CF ₂ CHF ₂ NO ₂ 1408 CCl ₃ H' Br " H CF ₂ CHF ₂ NO ₂ 1409 CCl ₃ H C = N H CF ₂ CHF ₂ NO ₂ 1410 CCl ₃ H Cl Cl CF ₂ CHF ₂ NO ₂ 1411 CCl ₃ H br Cl CF ₂ CHF ₂ NO ₂ 1412 CF ₂ CHF ₂ H Cl H CF ₂ CHF ₂ NO ₂ r.413 CF ₂ CHF ₂ H H H CF ₂ CHF ₂ NO ₂ 1414 CF ₂ CHF ₂ H br H CF ₂ CHF ₂ NO ₂ 1415 CF ₂ CHF ₂ H Cl Cl CF ₂ CHF ₂ NO ₂ 1416 CF ₂ CHF ₂ H br Cl CF ₂ CHF ₂ NO ₂ 1417 CF ₂ CHF ₂ CH ₃ H H CF ₂ CHF ₂ NO ₂ 1418 CF ₂ GHF ₂ CH ₃ Cl H CF ₂ CHF ₂ NO ₂ 1419 CF ₂ CF ₃ H Cl H CF ₂ CHF ₂ NO ₂ 1420 CF ₂ CF ₃ H br H CF ₂ CHF ₂ . NO ₂ 1421 CF ₂ CF ₃ CH ₃ H Cl CF ₂ CHF ₂ NO ₂ 1422 CF ₂ CF ₃ CH ₃ Cl H CF ₂ CHF ₂ NO ₂ 1423 CF ₂ CF ₃ . H C = N Cl CF ₂ CHF ₂ NO ₂

1 (continued) * 2 Cl ^R 4 * 5 ^R 6 -23- 263 220  physics. Constants Z "° c_7 table ^R 1 H br H OCF ₂ CHF ₂ NO ₂ • panties. 127-128- No.. CCl ₃ H H H OCF ₂ CHF ₂ NO ₂ Snip. 124-125 1424 CCl ₃ H ^ 3 H OCF ₂ CHF ₂ NO ₂ 1425 CCl ₃ H C ^ N H OCF ₂ CHF ₂ NO ₂ 1426 CCl ₃ H H H OCF ₂ CHF ₂ NO ₂ 1427 CCl ₃ CH ₃ Cl H CCF ₂ CHF ₂ NO ₂ 1428 CCl ₃ CH ₃ Cl ' H OCF ₂ CHF ₂ NO ₂ 1429 cci ₃ H br Cl OCF ₂ CHF ₂ NO ₂ 1430 CCl ₃ H H Cl OCF ₂ CHF ₂ NO ₂ 1431 cci ₃ H CH ₃ Cl OCF ₂ CHF ₂ NO ₂ 1432 CCl ₃ H H Cl CCF ₂ CHF ₂ NO ₂ 1433 CCl ₃ CH ₃ Cl Cl OCF ₂ CHF ₂ NO ₂ 1434 CCl ₃ CH ₃ Cl Cl OCF ₂ CHF ₂ NO ₂ 1435 CCl ₃ H br H OCF ₂ CHF ₂ NO ₂ Mp. 101-104 1436 CF CHF- H H H OCF ₂ CHF ₂ NO ₂ 1437 CF CHF- H F H OCF ₂ CHF ₂ NO ₂ 1438 CFjCHF- H C = N H • CCF ₂ CHF ₂ NO ₂ 1439 CF ₂ CHF ₂ H CH ₃ H OCF ₂ CHF ₂ NO ₂ 1440 CF ₂ CHF ₂ H H H CCF ₂ CHF ₂ NO ₂ SITP. 81-82 1441 CF ₂ CHF ₂ CH ₃ Cl H OCF ₂ CHF ₂ NO ₂ 1442 CF ₂ CHF ₂ CH ₃ Cl H OCF ₂ CHF ₂ NO ₂ 1443 CF ₂ CHF ₂ H - br Cl OCF ₂ CHF ₂ NO ₂ 1444 CF ₂ CHF ₂ H CH ₃ Cl CCF ₂ CHF ₂ NO ₂ 1445 CF ₂ CHF ₂ H H Cl , CCF ₂ CHF ₂ NO ₂ 1446 CF ₂ CHF ₂ CH ₃ . Cl Cl OCF ₂ CHF ₂ NO ₂ 1447 CF ₂ CHF ₂ CH ₃ H Cl OCF ₂ CHF ₂ NO ₂ 1448 CF ₂ CHF ₂ CF ₃ H H OCF ₂ CHF ₂ NO ₂ 1449 CF ₂ CHF ₂ CF ₃ H Cl OCF ₂ CHF ₂ NO ₂ 1450 CF ₂ CHF ₂ CF ₃ H *H OCF ₂ CHF ₂ NO ₂ 1451 CCl ₃ CF ₃ H Cl OCF ₂ CHF ₂ NO ₂ 1452 CCl ₃ H Cl H OCF ₂ CHF ₂ NO ₂ 1453 CF ₂ CF ₃ H br H OCF ₂ CHF ₂ NO ₂ 1454 CF ₂ CF ₃ H F H CCF ₂ CHF ₂ NO ₂ 1455 CF ₂ CF ₃ H H OCF ₂ CHF ₂ NO ₂ 1456 CF ₂ CF ₃  1457

Table 1 (continued) No. ¹ R ₁ 'R ₂

^K 6

physics. Constants j

1458 CF ₂ CF ₃ H CH ₃ H CCF ₂ CHF ₂ 1459 CF ₂ CF ₃ CH ₃ H H OCF ₂ CHF ₂ 1460 CF ₂ CF ₃ CF ₃ . H H OCF ₂ CHF ₂ 1461 CF ₂ CF ₃ H H Cl OCF ₂ CHF ₂ 1462 CF ₃ CF ₃ H Cl Cl OCF ₂ CHF ₂ 1463 CF ₂ CF ₃ H Br. Cl OCF ₂ CHF ₂ 1464 CF-CF ₃ H F Cl OCF ₂ CHF ₂ . 1,465 CF ₂ CF ₃ H CH ₃ Cl OCF ₂ CHF ₂ 1466 CF ₂ CF ₃ H C = N Cl OCF ₂ CHF ₂ 1467 CF ₂ CF ₃ CH ₃ H Cl OCF ₂ CHF ₂ 1468 CF ₂ CF ₃ CF ₃ H Cl OCF ₂ CHF ₂ 1469 CClF ₂ H Cl H OCF ₂ CHF ₂ 1470 CCl ₃ H H H OCF ₂ CHFCF ₃ 1471 CCl ₃ H Cl H OCF ₂ CHFCF ₃ 1472 CCl ₃ H br H OCF ₂ CHFCF ₃ 1473 CCl ₃ H F H CCF ₂ CHFCF ₃ 1474 CCl ₃ CH ₃ H H CCF ₂ CHFCF ₃ 1475 OCl ₃ CH ₃ Cl H CCF ₂ CHFCF ₃ 1476 CCl ₃ CF ₃ H H OCF ₂ CHFCF ₃ 1477 CF ₃ CF ₃ H H CCF ₂ CHFCF ₃ 1478 H Cl H CCF ₂ CHFCF ₃ 1479 CF ₂ Cl H CH ₃ H OCF CHFCF, 1480 CHCl ₂ H H H OCF ₂ CHFCF ₃ 1481 CF ₂ CHF ₂ H Cl H OCF ₂ CHFCF ₃ 1482 CF ₂ CHF ₂ H. br H OCF ₂ CHPCF ₃ 1483 CF ₂ CHF ₂ H. H H OCF ₂ CHFCF ₃ 1484 CF ₂ CHF ₂ H CH ₃ H OCF ₂ CHFCF ₃ 1485 CF ₂ CHF ₂ CH ₃ H Cl OCF ₂ CHFCF ₃ 1486 CF ₂ CHF ₂ H H Cl OCF ₂ CHFCF ₃ 1487 CF ₂ CF ₃ H H H OCF ₂ CHFCF ₃ 1488 CF ₂ CF ₃ H Cl H CCF CHFCF, 1489 CF ₂ CF ₃ H br H OCF ₂ CHPCF ₃ 1490 CF ₂ CF ₃ H Cl Cl CCF ₂ CHPCF ₃ 1491 CCl ₃ H H Cl OCF ₂ CHFCF ₃

NO ₂

NO ₂ NO ₂ NO ₂ NO ₂ NO ₂

NO ₂ NO ₂ NO ₂ NO.

NO ₂ NO ₂ NO ₂ NO ₂

NO ₂ NO ₂ NO ₂ NO,

NO ₂ NO ₂ NO ₂ NO ₂

NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ N0 "

Sup. 100-102 syrup syrup

syrup

No. ^R 1 "2 * 3 ^R 4 OCF ₂ CHFCF ₃ Λ -25- 263 220 physics. Constants f ° cj 1492 CCl ₃ H br Cl OCF ₂ CHClF NO ₂ 1493 CCl ₃ H Cl H OCF ₂ CHClF NO ₂ 1494 CCl ₃ H br H OCF ₂ CHClF NO ₂ Table 1 (continued) 1495 CCl ₃ H F H OCF ₂ CHClF NO ₂ 1496 CCl ₃ CH ₃ H H OCF ₂ CHClF NO ₂ 1497 CCl ₃ CF ₃ H H OCF ₂ CHClF NO ₂ 1498 CCl ₃ H H H ' OCF ₂ CHClF NO ₂ 1499 CCl ₃ H CH ₃ , H OCF ₂ CHClF NO ₂ 1500 CCl ₃ H CSN H OCF ₂ CHClF NO ₂ 1501 ^ 3 H H H OCF ₂ CHClF NO ₂ 1502 CF ₃ H Cl H OCF ₂ CHClF NO ₂ 1503 CF ₂ Cl H H H OCF ₂ CHClF NO ₂ 1504 CFBrCF ₃ H Cl H OCF ₂ CHClF NO ₂ 1505 CF ₂ CF ₂ CF ₃ H Cl H OCF ₂ CHClF NO ₂ 1506 CF ₂ CHF ₂ H Cl H OCF ₂ CHClF NO ₂ 1507 CF ₂ CHF ₂ H br H OCF ₂ CHClF- NO ₂ 1508 CF ₃ CHF ₂ H H OCF ₂ CHClF NO ₂ 1509 CF ₂ CHF ₂ CH ₃ H H OCF ₂ CHClF NO ₂ •. , 1510 CF ₂ CF ₂ CF ₃ H Cl H OCF ₂ CHClF NO ₂ 1511 CF ₂ CF ₂ CF ₃ H H H OCF ₂ CHClF NO ₂ 1512 CF ₂ CF ₃ H Cl H OCF ₂ CHClF NO ₂ 1.5.13 CF ₂ CF ₃ H br H OCF ₂ CHClF NO ₂ 1514 CF ₂ CF ₃ CH ₃ H H OCF ₂ CHClF NO ₂ 1515 CF ₂ CF ₃ H H H OCF ₂ CHFCl NO ₂ 1515. CCl ₃ H H Cl OCF ₂ CHFCl NO ₂ 1517 CCl ₃ H Cl Cl OCF ₂ CHFCl NO ₂ 1518 CCl ₃ H br Cl OCF ₂ CHFCl NO ₂ 1519 CCl ₃ CH ₃ H . Cl OCF ₂ CHFCl NO ₂ 1520 CF ₂ CHF ₂ H H Cl OCF ₂ CHFCl NO ₂ 1521 CF ₂ CHF ₂ . H Cl Cl OCF ₂ CHFCl NO ₂ 1522 CF ₂ CHF ₂ H br Cl OCF ₂ CHFCl N0 ₂ ^; 1523 CF ₂ CHF ₂ H C = N Cl OCF ₂ CHFCl NO ₂ 1524 CF ₂ CHF ₂ H CH ₃ H OCF ₂ CHF NO ₂ 1525 CH ₃ H H H N0 _?

Table 1 (continued)

No. *1 "2 H ^R 4 * 5 ^R 6 physics. Constants f ° Cj 1526 CH ₃ H br H OCF ₂ CHF ₂ NO ₂ 1527 CH ₃ H Cl H OCF ₂ CHF ₂ NO ₂ 1528 CF ₂ Cl H H H OCF ₂ CHF ₂ NO ₂ 1529 CF ₃ CF ₂ CF ₂ H Cl H OCF ₂ CHF ₂ NO ₂ 1530 CF ₂ CHFCl H Cl H OCF ₂ CHF ₂ NO ₂ 1531 Cl H br H OCF ₂ CHF ₂ NO ₂ 1532 CH ₃ - H H H OCF ₂ CHFCF ₃ NO ₂ 1533 CH ₃ H br H OCF ₂ CHFCF ₃ NO ₂ 1534 £> H H H OCF ₂ CHFCF ₃ NO ₂ 1535 O H . br H OCF ₂ CHFCF ₃ NO ₂ 1536 CF ₂ Cl H Cl H OCF ₂ CHFCF ₃ NO ₂ 1537 CF ₂ CF ₂ CF ₃ H Cl *-H OCF ₂ CHFCF ₃ NO ₂ 1538 CCl ₃ H H H OCFCl ₂ NO ₂ 1539 CCl ₃ H Cl H OCFCl ₂ NO ₂ 1540 CCl ₃ H br H OCFCl ₂ NO ₂ 1541 CCl ₃ · H CH ₃ H OCPCl ₂ NO ₂ 1542 CCl ₃ H- CSN H OCFCl ₂ NO ₂ 1543 CCl ₃ H H H OCF ₂ Cl NO ₂ 1544 CCl ₃ H Cl H OCF ₂ Cl NO ₂ 1545 CCl ₃ H br H OCF ₂ Cl NO ₂ 1546 CCl ₃ H CH ₃ H OCF ₂ Cl NO ₂ 1547 CCl ₃ H C = N H OCF ₂ Cl NO ₂ 1548 CF ₂ CHF ₂ H H H OCFCl 2 NO ₂ 1549 CF ₂ CHF ₂ H Cl H OCFCl ₂ NO ₂ 1550 CF ₂ CHF ₂ H   br H OCFCl ₂ NO ₂ 1,551 1,552 CF ₂ CHF ₂ CF ₂ CHF ₂ CH ₃ H H H H H OCF ₂ Cl OCF ₂ Cl NO ₂ NO ₂ 1553 CF CHF- H Cl H OCF ₂ Cl NO ₂ 1554 CF ₂ CF ₃ H H H OCF ₂ Cl NO ₂ 1555 CF ₂ CF ₃ H Cl H OCF ₂ Cl NO ₂ 1556 H H H OCFCl ₂ NO ₂ 1557 CF ₂ CF ₃ H Cl H OCPCl ₂ NO ₂ 1558 CCl ₃ H H H OCHF ₂ NO ₂ 1559 CCI, H Cl H 0CHF " N0 "

Table 1 (continued)

* 2

physics

 constants

Z ~ ° c_7

CCl ₃ CCl CCl CCl ₃

cci

CCI

1,560 1,561 1,562 1,563 1,564 1,565 1,566

1,567 CF ₂ CHF ₂

1,568 CF ₂ CHF ₂

1,569 CF ₂ CHF ₂

1,570 α

1.571 σ

1,572 CF ₂ CHF ₂

1,573 CF ₂ CHF ₂

1.574 CF ₂ CF ₃

1.575 CF ₂ CF ₃

1,576 1,577 1,578

CCl ₃ CCl ₃ CCl ₃

1,579 CF ₂ CHF ₂

1,580 CF ₂ CHF ₂ .DoI> _χ - (_ fir ~

1,582 CF ₂ CF ₃

1,583 CF ₂ CF ₃

1,584 CF ₂ CF ₃

1,585 CH ₃

1,586 CH ₀

1,587 1,588 1,589 1,590 1,591 1,592 1,593

^σ 3 CF ₂ Cl

CCl

CH ₃

CH ₃

H-

CH ₃

H-

CH ₃

CH ₃

br

Cl

br

Cl

br

CH ₃

Cl

br

C = N

Cl

Cl

C = N

CH ₃

Cl

Cl

Cl

Cl

Cl

Cl

Cl

H ⁰ CHF ₂ NO ₂

H OCHF ₂ NO ₂

Cl OCHF ₂ NO ₂

Cl CCHF ₂ NO ₂

Cl OCHF ₂ NO ₂

Cl CCHF ₂ NO ₂

H OCHF ₂ NO ₂

H OCHF ₂ NO ₂

H OCHF ₂ NO ₂

H OCHF ₂ NO ₂

Cl CCHF ₂ , NO ₂

Cl OCHF ₂ NO ₂ .

Cl CCHF ₂ NO ₂

Cl OCHF ₂ NO ₂

H OCHF ₂ NO ₂

H OCHF ₂ NO ₂

H OCF NO _n

H OCF ₃

NO ₂ Snp. 44-48

H OCF ₃ NO ₂

H OCF ₃ . NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₃ NO ₂

H OCF ₂ CHCl ₂ NO ₂

Snp. 94-96

Table 1 (continued)

Kr. ^R 1 * 2 * 3 ^R 4 OCF ₂ CHCl ₂ ^R 6 physics. Constants f ° cj 1594 CCl ₃ CH ₃ H H. OCF ₂ CHCl ₂ NO ₂ 1595 CCl ₃ H Cl H OCF ₂ CHCl ₂ NO ₂ 1596 CH ₃ H H H OCF ₂ CHCl ₂ NO ₂ 1597 CH ₃ H br H OCF ₂ CHCl ₂ NO ₂ 1598 CF ₂ CHF ₂ H H H OCF ₂ CHCl ₂ NO ₂ 1599 CF ₂ CHF ₂ H Cl H OCF ₂ CHCl ₂ NO ₂ 1600 CF ₂ CHF ₂ H br H OCF ₂ CHCl ₂ NO ₂ 1601 CF ₂ CF ₃ H Cl H OCF ₂ CHCl ₂ NO ₂ 1602 CF ₂ CF ₃ H br H CCF ₂ CHCl ₂ NO ₂ 1603 CF ₂ CF ₃ H H H OCF ₂ CHCl ₂ NO ₂ 1604 CF ₂ Cl H Cl H OCF ₂ CHCl ₂ NO ₂ 1605 CF ₂ CF ₂ CF ₃ H Cl H OCF ₂ CF ₃ NO ₂ 1606 CCl ₃ H H H OCF ₂ CF ₃ NO ₂ 1607 CCl ₃ H Cl H CCF ₂ CF ₃ NO ₂ 1608 CF ₂ CHF ₂ H Cl H OCF ₂ CF ₃ 1609 CF ₂ CHF ₂ H H H CCF ₂ CF ₃ OCF ₂ CF ₃ NO ₂ 1,610 1,611 C ₂ H ₅ CCH ₃ H H Cl Cl H H CCF ₂ CF ₃ No ² 1612 Cl H br H OCF ₂ CHFBr NO ₂ 1613 CCl ₃ H H H CCF ₂ CHFBr NO ₂ 1614 CCl ₃ H Cl H NO ₂

1,618 CH ₃

1.619 CH ₃

1.615 CF ₂ CHF ₂ HH

1,616 CF ₂ CHF ₂ H Cl

1,617 CF ₂ CHF ₂ H Br

H H

H Br

H H

H Cl

H Cl

H Br

H Cl

H Br

1.621 t> -

1,622 cl

1,623 cl

1.624 CF ₃ CF ₃

1.625 CF ₂ CF ₃

1.626 CCl ₃

1.627 CCl,

H OCF ₂ CHFBr NO ₂ H OCF ₂ CHFBr NO ₂ H OCF ₂ CHFBr NO ₂

OCF ₂ CHFBr

H OCF ₂ CHFBr NO ₂

H H

CCF ₂ CHFBr CCF ₂ CHFBr

H . OCF ₂ CHFBr NO ₂ H OCF ₂ CHFBr NO ₂

CH, H

H Cl

H H H H

OCF ₂ CHFBr OCF ₂ CHFBr CCH ₂ CF ₃

NO ₀

^R 1 H - ^R 3 ^R 4 OCH ₂ CF ₃ ^R 6 -29- 263 220 physics. CCl ₃ H br H CCH ₂ CF ₃ NO ₂ constants CCl ₃ H C = N H OCH ₂ CF ₃ NO ₂ Table 1 (continued) CH ₃ H Cl H OCH ₂ CF ₃ NO ₂ CH ₃ H H H OCH ₂ CF ₃ NO ₂ No. H H H OCH ₂ CF ₃ NO ₂ 1628 J> - H Cl H OCH ₂ CF ₃ NO ₂ 1629 CF ₃ H H H CCH ₂ CF ₃ NO ₂ 1630 CF ₂ CHF ₂ H Cl H OCH ₂ CF ₃ NO ₂ 1631 CF ₂ CHF ₂ H H H CO ₂ Et NO ₂ 1632 C = N H br H C = N NO ₂ 1633 C = N H br H Cl NO ₂ 1634 C = N H br H CO ₂ CH (CH ₃ ) ₂ NO ₂ 1635 CF ₂ CHF ₂ H Cl Cl CO ₂ CH (CH ₃ ) ₂ NO ₂ 1636 CCl ₃ H H Cl CO ₂ CH (CH ₃ ) ₂ NO ₂ semi-crystalline 1637 CCl ₃ H Cl Cl OCF ₂ CHF ₂ NO ₂ Mp. 84-86 1638 CF ₂ Cl H Br. H br NO ₂ 1639 CCl ₃ H - Cl H br NO ₂ Snp. 103-108 1640 CCl ₃ H br H F NO ₂ 1641 CCl ₃ H br H F NO ₂ 1642 CCl ₃ -H Cl ^ H CO ₂ (CH ₂ ) ₇ CH ₃ NO ₂ 1643 CF ₂ CF ₂ CF ₃ H Cl H CO ₂ (CH ₂ ) ₇ CH ₃ NO ₂ 1644 CF ₂ CHPCF ₃ H Cl H CO ₂ (CH ₂ ) ₇ CH ₃ NO ₂ 1645 CF ₂ CHFCF ₃ H Br H ^CO 2 ^C 6 ^F 5 NO ₂ 1646 CF ₂ CHFCF ₃ H Cl H CO ₂ CH (CH ₃ ) 2 NO ₂ 1647 CH ₃ H Cl H CO ₂ Et NO ₂ 1648 ^C 6 ^F 5 CH ₃ Cl H CO ₂ Et NO ₂ Snp. 165 1649 ^C 6 ^F 5 H H H CeN NO ₂ 1650 ^C 6 ^F 5 H H H C = N NO ₂ 1651 ^C 6 ^F 5 H Cl H C = N NO ₂ 1652 ^C 6 ^F 5 H br H CO ₂ Et NO ₂ 1653 ^C 6 ^F 5 H br H CO-N (CH.,)., NO ₂ 1654 CF ₂ CHF ₂ Cl Cl H C = N NO ₂ 1655 CF ₂ CHF ₂ H H Cl CO ₂ CH (CH ₃ ) ₂ NO ₂ Snp. 256-258 1656 CF ₂ CF ₂ CF ₃ Cl Cl NO ₂ semi-crystalline 1657 Mp. 81-85 1658 1659 1660 1661

Continuation Table 1

^R 1

^R 3

^R 6 physics. constants

rc /

1662 ⁿ ~ C'7 ^F 15 H Cl H CO ₂ Et 1663 H Cl H C = N 1664 Π Vrf-jl 4 [- H Cl H CO ₉ CH (CH,) 1665 nC ₇ F ₁₅ H br H CO ₂ Et 01/06/66 11-C ₇ F ₁₅ H br H C = N 1667 Fi-C ₇ F ₁₅ H br H Cl 1668 CF ₂ CHF ₂ CH ₃ H H C = N 1669 CF ₂ CHF ₂ CH ₃ br H CO ₂ CH ₃ 1,570 CF ₂ CHF ₂ CH ₃ br H CO ₂ Et 1671 CF ₂ CHF ₂ CH ₃ br Cl CO ₂ CH (CH ₃ ) 1672 CF ₂ CHF ₂ ' H br H br 1673 CF ₂ CHF ₂ H Cl H br 1 ^ 674 CF ₂ CHF ₂ CH ₃ Br H br 1675 CF ₂ CHFCF ₃ H br H br 1676 CCl ₃ H , br H F 1677 CF ₂ CHF ₂ H • Br H F

NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO, syrup SRTP. 88-89

Table 2

10

physics

 constants

CCl ₅ H H H C = N CCl ₅ H H Cl CO ₂ Et CF ₂ CHF ₂ H H H CCl ₅ CF ₂ CHF ₂ H H . H CO ₂ Et

NO ₂ FO ₂ NO ₂ NO.

K K K K

^R 1 "2 H ^R 4 * 5 NO ₂ • physics. -31 - 263 220 CCl ₃ H Cl H CH ₃ NO ₂ R .. Q constants rci cci _3t H Cl H CP ₂ Cl NO ₂ κ anp. 147-150 CCl ₃ H Cl H cm NO ₂ K Table 2 (Port setting CCl ₃ H Cl H S O ₂ NCg NO ₂ K anp. 103-107 CCl ₃ H Cl Cl CO ₂ Et NO ₂ K anp. 106-111 - No. CP ₂ CHP ₂ H Cl H CO ₂ Et NO ₂ K 2.5 CP ₂ CHP ₂ H Cl Cl CO ₂ Et NO ₂ K, pp. 257-260 2.6 CP ₂ CHP ₂ H Cl H CsN NO ₂ K 2.7 CF ₂ CHP ₂ H · Cl Cl CSN NO ₂ K anp. 117-121 2.8 CP ₂ CHP ₂ H Cl H CH ₃ NO ₂ K 2.9 CCl ₃ H CH ₃ H CSN NO ₂ K 2.10 CCl ₃ H CH ₃ Cl CO ₂ Et NO ₂ K 2.11 CCl ₃ H CH ₃ H CH ₃ NO ₂ N / A 2.12 CP ₂ CP ₃ H Cl H CSN. ; NO ₂ K 2.13 CP ₂ CHP ₂ ' H ' Cl Cl CP ₃ NO ₂ K anp. 125-129 2.14 CCl ₃ H Cl H CO ₂ Et NO ₂ K anp. 272-274 2.15 CP ₂ Cl H br H C £ N NO ₂ OCH ₃ 2.16 CP ₂ CHP ₂ H Cl H CCl ₅ NO ₂ OCH ₃ 2.17 CP ₂ CP ₃ H C = N Ξ CH ₃ NO ₂ CH- 2.18 CCl ₃ H br H CP ₂ Cl NO ₂ C ₂ H ₅ ; 2.19 CP ₃ " H H Cl CO ₂ Et NO ₂ OCH ₃ 2.20 cm H Cl Cl CSN NO ₂ OC ₂ H ₅ 2.21 CCl ₃ Cl Cl y h CCl ₂ F NO ₂ 2.22 CCl ₃ H Cl Cl CO ₂ Et NO ₂ OCH ₃ 2.23 CP ₃ H P H C2N NO ₂ CH ₃ 2.24 CH ₃ H Cl H CCl ₃ NO ₂ C ₂ H ₅ 2.25 CCl ₂ CHP ₂ Cl H Cl CP ₂ Cl. NO ₂ OC ₃ H ₇ · 2.26 Cl H Cl Cl CO ₂ Bu NO ₂ CH ₃ 2.27 CP ₃ H H J CONHMe NO ₂ CCH ₃ 2.28 CHCl ₂ CH ₃ H br CONHEt NO ₂ C ₂ H ₅ 2.29 CH ₂ = CP CH ₃ H Cl CONME ₂ CH ₃ 30.2 C ₂ S ₅ 2.31 2:32 2:33 2:34 2:35

Table 2 (continued)

R 1 R 2 H H R 3 R 4 R 5 CO et 2 R 6 C η Mo wu C NO R 10 physics. ^: 3 No. CCl ₂ = CC] Cl H H H Cl CH ₃ C = N HO ₂ C 9 iuo OCH constants CHCl ₂ H H Cl Cl C ₂ H ₅ CO K C = N BO ₂ C 9 ^N ° 2 NO ² 9 N / A T ⁰ Cl 2:36 CHBr ₂ C ₂ H ₅ . H H SCH ₃ C ₄ H ₉ CH NO ₂ . NO ii 2:37 CP ₂ CHP ₂ H H Cl CC ₄ H ₉ CO ₂ N (CH ₃ ). CO ³ Et ₂ N0 ₂ UO PIw 2 N / A Mp.> 275 2:38 CH OCH H CF H- C = N NO NO NO ₂ K Mp. 213-218 2:39 ^CH 3 CCl OCH H ^CF 3 H C = N K Mp. 137-141 2:40 cci ³ cn / H H ³ H Cl K Mp. 180-183 2:41 ³ 3 CH H H C = N K Mp. 113-117 2:42 CCI CH ³ H H C = N K Mp. 187-190 2:43 CCI CH ³ Cl H CO et K Mp. 120-123 2:44 CF ₂ CF ₃ 3 Cl H OGF CHF K Mp. 125-129 2:45 CF CHF 2 2 Cl H CO et 2 K Mp. 265-267 2:46 CF CHF Cl H C = N K Mp. 180-183 2:47 CC? F Cl H OCF CHF 2 2 K Mp. 277-278 2:48 CClF ² Cl H CO ₂ Et K Mp. 263-267 2:49 CClF ² Cl H K Mp. 243-245 2:50 CCIF Cl H , κ Mp. 185-189 2:51 CCIF CsN H , K Mp. 267-268 2:52 CF CHF 9 9 CsN H K Mp. 260-262 2:53 CC CCl, Cl H K syrup 2:54 Cl H K 2:55 2:56

Table?

IIA ^ N

R.

NO-

^R 1 R ₂ R ₃ * • ^R 5 ^R 6 physics. No. . ^R 4 constants CCl ₃ H H CF ₃ NO ₂ Snp. fC] 3.1 CCl ₃ Cl H , H CF ₃ NO ₂ 106-108 3.2 CCl ₃ H H Cl CF ₃ NO ₂ 3.3 cci ₃ Cl H egg CF ₃ NO ₂ 3.4 CCi ₃ CH ₃ H H CF ₃ NO ₂ 3-5 CCl ₃ CH ₃ H H CF ₃ NO ₂ 128-131 3.6 CF ₂ CF ₃ H H Cl CF ₃ NO ₂ 205-207 3.7 CF ₂ CF ₃ H H H CF ₃ NO ₂ 3.8 - CCl ₃ CH ₃ H - Cl CO ₂ Et NO ₂ syrup 3.9 CCl ₃ H Cl H CF ₃ NO ₂ syrup 3:10, CCl ₃ B Cl H CF ₃ NO ₂ 125-127 3.11 CF ₂ CHF ₂ H Cl Cl CF ₃ NO ₂ 3.12 CF ₂ CHF ₂ H Cl H CF ₃ NO ₂ 3.13 CCl ₃ ... H Cl Cl C = N NO ₂ syrup 3.14 CCl ₃ H Cl H . C = N NO ₂ 3.15 CCl ₃ H Cl Cl CO ₂ Et NO ₂ 3.16 CCl ₃ H Cl H CO ₂ Et NO ₂ 3.17 CCl ₃ H -. Cl egg CCl ₃ NO ₂ 3.18 CCl ₃ H Cl H CCl ₃ NO ₂ 3.19 CF ₂ CHF ₂ H Cl Cl C = N NO ₂ 3.20 CF ₂ CHF ₂ H Cl H C = N NO ₂ 3.21 CF ₂ CHF ₂ H Cl Cl CO ₂ Et NO ₂ 3.22 H

Table 3 (Port setting)

^R 1 R ₂ ^R 3 R ₄ ^R 5 ^R 6 physics. No. constants CP ₂ CHP ₂ H Cl, Cl. CO ₂ Et NO ₂ Smp.f Cl 3.23 CP ₂ CHP ₂ H Cl H CCl ₅ NO ₂ 3.24 CP ₂ CHP ₂ H Cl Cl CP ₂ Cl NO ₂ 3.25 CP ₂ CP ₅ H CH ₅ H CP ₅ NO ₂ 3.26 CP ₂ CP ₅ H CH ₅ Cl CP ₅ NO ₂ 90-92 3.27 CCl ₅ H CH ₅ H: CP ₂ Cl NO ₂ 98-100 3.28 CCl ₅ H CH ₅ Cl CP ₂ Cl NO ₂ 3.29 CCl ₅ H CH ₅ H CP ₅ NO ₂ 3.30 CCl ₅ , H CH ₅ Cl CP ₅ • NO ₂ 3.31 CH ₅ . H CHN H C5N CP ₅ - 3:32 OCH ₅ H br Cl CO ₂ CH ₅ CP ₅ 3:33 Cl : Cl Cl H CP ₅ NO ₂ 3:34 SCH ₅ H br H CP ₅ NO ₂ 3-35 H br Cl CSN NO ₂ 3-36 CP ₅ CH ₅ Cl Ή CO ₂ Et NO ₂ 3:37 CP ₅ CH ₅ Cl Cl CO ₂ Et NO ₂ 3:38 CH ₅ H Oil ·. Cl CO ₂ Et NO ₂ 3:39 NMe ₂ NMe ₂ H Cl CCl ₅ NO ₂ 3:40 NMe ₂ NMe ₂ H H CCl ₅ NO ₂ 3:41 NHC ₂ H ₅ NHC ₂ H 5 ^H Cl CH ₅ NO ₂ 3:42 CCl ₅ H Cl H NO ₂ CP ₅ 3-43 CCl ₅ H Cl Cl NO ₂ CP ₅ . 3:44 H CCl ₅ H Cl NO ₂ CP ₅ 3:45 H CCl ₅ H Cl CP ₅ NO ₂ 3:46 CP ₂ CHP ₂ H CH ₅ H CP ₅ NO ₂ 3:47 CP ₂ CHP ₂ H CH ₅ Cl CP ₅ NO ₂ 87-88 3:48 CCl ₅ ClCH ₂ H H CP ₅ NO ₂ 93-95 3:49 CCl ₅ CH ₅ H H CCl ₅ NO ₂ 129-131 3:50 CCl ₅ CH ₅ H Ή CH ₅ NO ₂ semi-crystalline 3:51 CCl ₅ CH ₅ H Cl CO ₂ Et NO ₂ 189-191 3:52 CCl ₅ . CH ₅ H H CSN NO ₂ semi-crystalline 3:53 175-177

-35- 263 220 Table 5 ' (Port setting)

^R 1 ^R 2 ^R 3 ^R 4 physics. '* CP 3 No. R ₁ - Constants ä χ C ^ C \ f'TT ι r ^ XJ ι w ν / Λ \ y 'Ji \ \ j Xl ^ * / f \ CP ₂ CHP ₂ CH H Cl Smp.fCl CP 3-54 ' CP ₂ CHP ₂ CH ₃ H Cl C0 ₂ CH (CH _{3) 2} 3:55 CCI CH ₃ Cl Cl CO ₂ C ₆ P ₅ C0 ₂ CH (CH ₃ ) ₂ ι 3-56 CCl ₃ CH ₃ H Cl C0 ₂ CH (CH _{3) 2} 3-57 CCl cci ₃ CH ₃ . H H.H , σι Cl C0 ₂ CH (CH _{3) 2} Vj) Vj) VJl VJl VO OO CCl ₃ H br Cl λ Ο C ^ TT f ^ l TT- ι V \ J f \\ J XX V \ S Fin J ** 3-60 CCl ₃ H CH ₃ Cl CO ₂ C ₆ F ₅ 3.61 CP ₂ CHP ₂ H CH ₃ Cl CP 3-62 CP ₂ CHF ₂ , H CH ₃ , Cl CP ₃ 3. 63 CP ₂ CHP ₂ H br Cl CP ₃ 3-64 CCl ₃ H br Cl ΠΛ i * ^ TT ff TT ι w \ J f \\ J Xl VW XX * TJ Λ 3-65 CP ₂ CHP ₂ , H . H Cl OCP ₃ 3.66 CP ₂ CHP ₂ H H- Cl CO ₂ (CH ₂ O ₃ CH ₃ 3-67 CCl ₃ H Cl   egg C0 ₂ (CH ₂ ) ₃ CH ₃ 3.68 CCl ₃ CCl, CH ₃ CH ₃ H Cl Cl Cl C = N 3-69 3-70 H .CH ₃ Cl C = N 3.71 CCl ₃ , H ·. < Cl Cl C = N 3-72 CCl ₃ CH H Cl 3-73 CP ₂ CHP ₂ H . · br * Cl CP ₃ 3-74 ^C 6 ^P 5 H br Cl CP ₃ 3-75 ^C 6 ^P 5 CH ₃ H Cl 3-76 CP CHP ₂ CH ₃ br Cl 3-77

Table 4

^R 1 R ₂ E ₃ ' ^R 4 ^R 5 ^R 6 physics. No. CCl ₃ H H H CP ₃ NO ₂ constants 4.1 cci ₃ H H Cl CP ₃ NO ₂ 138-141 4.2 CCl ₃ H H H CSN NO ₂ 73-75 4.3 cci ₃ H H Cl CsN. NO ₂ 4.4 cci ₃ H H H CO ₂ Et NO ₂ 4.5 CCl ₃ H H H H -Cl H CH ₃ CCl ₃ NO ₂ NO ₂ 4.6 4.7 CCl ₃ H H H NO ₂ CP ₃ 4.8 CCl ₃ H H Cl NO ₂ CF ₃ 4.9 CP ₃ CP ₃ H H H H H Cl CF, CP ₃ NO ₂ NO ₂ 4.10 4.11 CP ₃ · H H H CSN NO ₂ 4.12 CP ₃ H H Cl CSN NO ₂ 4.13 CP ₃ H H H CO ₂ Et NQ ₂ 4.14 CP ₃ . H H Cl CO ₂ Et NO ₂ 4.15 CP ₃ H H H CCl ₃ NO ₂ 4.16 CP ₃ H H Cl CCl ₃ NO ₂ 4.17 CP ₂ CHP ₂ H H . H CP ₃ NO ₂ 4.18 CP ₂ CHP ₂ CP ₂ CHP ₂ H H H H Cl H CP ₃ NO ₂ NO ₂ 4.19 4.20 CP ₂ CHP ₂ H H Cl CSN NO ₂ 4.21 OCH ₃ CH ₃ H Cl CP ₂ Cl NO ₂ 4.22 SCH ₃ SCH ₃ H H- CHCl ₂ NO ₂ 4.23 CCl ₃ CH ₃ H H CP ₃ NO ₂ 4.24 52-55

Table 4 (continued)

No.

^R 1

R ₂ R ₃

physics. constants

rci

4.25

4.26 CCl ₃

4.27 CCl,

4.28 CCl ₃

4.29 CCl ₃

4.30 CCl ₃

4.31 CCl,

CH ₃ H Cl

CH ₃ HH

CH ₃ H Cl

CH ₃ HH

CH ₃ Ή CH ₃ H CH.

4.32 CCl ₃

H Cl

H H

4 ..33 CCl ₃ CHj H ·. Cl 4-34 CF ₂ CHF ₂ CH ₃ HH

4.35 CF ₂ CHF ₂ CH ₃ H Cl

4.36 CF ₂ CHF ₂ CH ₃ HH

4.37 CF ₂ CHF ₂ CH ₃ E

CH

H H-

CF ₂ CHF, 4.38 CF ₂ CHF ₂ 4 · 39 CF ₂ CHF ₂ WU

4.40 CF ₂ CHF ₂ CH ₃ HH

4.41 C ₃ F ₇ HH Cl

4.42 CH,

Η- H Cl

4-43 CHN HH H

4.44 C ₇ F ₁₅ ; HH-H

4.45 CF ₂ CHCl ₂ HH Cl

4.46 Cl HH H

4.47 CCl ₃ H Cl H

4.48 CCl ₃ H Cl Cl

4.49 CCl ₃ . H Cl H

4.50-CCl ₃ . H Cl Cl

4.51 CCl ₃ H. Cl H

4.52 CCl ₃ H Cl. Cl 4-53 CCl ₃ H Cl H. 4.54 CCl, H Cl Cl

CF ₃ C = N CHN CH,

CCl ₃

CCl ₃

NO ₂

NO ₂

CF ₃

CF ₃

CCI

CF

NO

NO,

NO,

no!

_[2 mp. 175-177

CO ₂ Et NO ₂

NO ₂ NO ₂ CF ₃ CF ₃ NO ₂ NO ₂ NO,

^WU 2

CCl ₃ NO ₂

CH ₃ NO ₂

CO ₂ Et NO ₂

CSN NO ₂

CF ₂ Cl NO ₂

NO

CO ₂ CH ₃ NO ₂ CCl

NO

CF ₂ CHF ₂ NO ₂ CF ₃ CF ₃ CF ₃ C = N

NO ₂ NO ₂ NO ₂ NO ₂ ChN NO ₂ CO ₂ Et NO ₂ CO ₂ Et NO ₂ NOo

CH ₃ CH,

Mp. 97-100 smo. 157-160

Mp. 180-182 Mp. 112-114

NO

Table 4 (Port setting)

No.

physics. Rc Rg constants rci

4:55

4.56 CCl!

4.57 CCl.

H H

Cl Cl

Cl H CCl ₅ NO ₂ CCl

CH ₃

NO

NO

Mp. 138-140

4.58 CCl

4.59 4.60 4.61 4.62 4.63 4.64 4.65 4.66

4.68 4.69 4.70 4.71 4.72

4.73

CCI,

CCI, CCli

CP ₂ Cl CP ₂ Cl CP ₂ Cl CP ₂ Cl

4.67 CHCl,

CHCl ₂

OEt

NHCH ₅

SCH

H H H H H H H H H H H H

Cl Cl CH ₃

SCH (CH ₃ ) 2H

Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl

CP ₂ Cl

CP ₂ Cl

NO ₂

NO ₂

C = N '

C = N

CP ₅ CP ₅

CP ₅ CP ₅ CP ₅ CP ₅ C = NC = N CO ₂ Et

NO

NO, NO ₂ CF, CP 1 NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO.

4.74 - (O) -ClH

Cl

4.75 0- ^ O) -Cl H

Cl Cl

Cl H CO ₂ Et NO ₂

CP ₅ NO ₂

4.76 CCl ₂ CCl ₅ CH ₅ Cl

4.77 CCl,

CH, Cl

NO, NO,

Table 4 (continued)

No.

^R 1

physics. Rc Rg constants

rcn

4.78 CF ₂ CHF ₂ CH ₃ Cl H CO ₂ Et NO ₂ 4.79 CH ₃ CH ₃ Cl F CF ₃ NO ₂ 4.80 CF ₃ H Cl H CSN NO ₂ 4 ... 81 CF ₃ H Cl Cl CO ₂ Et NO ₂ 4.82 4.83 CF ₃ CH ₃ H H Cl Cl Cl H CCl ₃ CCl ₃ NO ₂ NO ₂ 4.84 CH ₃ H Cl Cl CF ₃ NO ₂ 4.85. CH ₃ H Cl Cl CSN NO ₂ 4.86 CH ₃ H Cl H CO ₂ CH ₃ NO ₂ 4.87 - <3 H - Cl H CO ₂ Et NO ₂ 4.88 -4 H Cl Cl CF ₂ Cl NO ₂ 4.89 -A H Cl Cl C = N NO ₂ 4.90 C ^ N. ^ H- Cl H. CCl ₃ NO ₂ 4-91 CSN H Cl Cl NO ₂ CF ₃ 4.92 Cl -H Cl Cl CSN Noo

4.93 CF ₂ CHF ₂ H. Cl H

4.94 'CF ₂ CHF ₂ H Cl Cl

4.95 CF ₂ CHF ₂ H Cl. H

4.96 CF ₂ CHF ₂ H Cl Cl

4.97 CF ₂ CHF ₂ H Cl H

4.98 CF ₂ CF ₃ H Cl Cl

4.99 CF ₂ CHF ₂ H Cl H

4,100 CF ₂ CHF ₂ H Cl Cl

4,101 CF ₂ CHF ₂ H Cl H

4,102 CF ₂ CHF ₂ H Cl Cl

4,103 CF ₂ CHF ₂ H Cl H

4,104 CF ₂ CHF ₂ H Cl Cl

4.105 C ₃ F ₇ H Cl H

4.106 C ₃ F ₇ H Cl Cl

4.107 C ₇ F ₁₅ H Cl H

CF ₃ NO ₂ mp 88-90 CF ₃ 'NO ₂ smp. 80-85 CCl

NO, NO, CF,

NOj

NO ₂

NO,

CF ₃ NO ₂ syrup

CSN 'NO ₂

CSN NO ₂

CO ₂ Et NO ₂

CO ₂ Et NO ₂

CF

CF ₃ -. NO ₂ CF ₃ ^ NO ₂

Table 4 (continued)

^R 1 R ₂ ^R 3 ^R 4 ^R 5 R ₆ physics. No. constants ^C 7 ^P 15 H Cl Cl CSN NO ₂ rc ι 4108 CF ₂ CHClF H Cl H CO ₂ Et NO ₂ 4109 CF ₂ Cl H Cl H CO ₂ Et NO ₂ 4110 CF ₂ Cl H Cl Cl CO ₂ Et NO ₂ 4111 CHCl ₂ H Cl H CSN NO ₂ 4112 CHCl ₂ H Cl Cl CsN NO ₂ 4113 CF ₅ H Cl H CF ₅ NO ₂ 4114 CF ₅ H Cl Cl CF ₅ NO ₂ 4115 CCl ₅ H br H CF ₅ NO ₂ 4116 CCl ₅ H br Cl CF ₅ NO ₂ Mp. 64-68 4117 CCl ₅ H br H C = K NO ₂ Mp. 124-128 4118 CCl ₅ H br Cl CSN NO ₂ 4119 CCl ₅ H br H CO ₂ Et NO ₂ 4120 CCl ₅ H br Cl CO ₂ Et NO ₂ 4.12.1 CCl ₅ H br H CH ₅ NO ₂ 4122 CCl ₅ H br Cl CH ₅ NO ₂ 4123 CCl ₅ H br -H CCl ₅ NO ₂ 4124 CCl ₅ H br Cl CCl ₅ NO ₂ 4125 OEt OEt br H CH ₅ NO ₂ 4126 Set Set br H SO ₂ NMe ₂ NO ₂ 4127

Cl Br

Cl

C = N

NO

4129 -4 OCH ₅ br Cl NO ₂ CF ₅ 4130 -ή H br H CHCl ₂ NO ₂ 4131 CHCl ₂ H br Cl CHCl ₂ NO ₂ 4132 CHCl ₂ Cl br H CF ₂ Cl NO ₂ 4133 OCH ₅ Cl br Cl CF ₂ Cl NO ₂ 4134 CH ₅ br H CF ₅ NO ₂

Table 4 (continued)

^R 1 R ₂ ^R 3 ^R 4 ^R 5 ^R 6 physics. 115-118 No. CF ₂ CHF ₂ H br H CF ₅ NO ₂ . Constants rci 76-78 4135 CF ₂ CHF ₂ H br Cl CF ₅ NO ₂ 111-112 4136 CF ₂ CHF ₂ H br H C = N NO ₂ 180-182 4137 CF ₂ CHF ₂ H br Cl C = N NO ₂ 4138 CF ₂ CHF ₂ - H br H CCl ₅ NO ₂ 4139 CF ₂ CHF ₂ H br Cl CCl ₅ NO ₂ 4140 CF ₂ CHF ₂ H br H CO ₂ Et NO ₂ 4141 CF ₂ CHF ₂ H br Cl CO ₂ Et NO ₂ 4142 CF ₂ CHF ₂ H br H CH ₅ NO ₂ 4143 CF ₂ CHF ₂ H br Cl CH ₅ NO ₂ 4144 CF ₂ CHF ₂ H br H NO ₂ CF, 4145 CF ₂ CHF ₂ H br Cl NO ₂ 3 4146 CF ₂ CF ₅ H br H CF ₅ 4147 .CF ₂ CF ₅ H br Cl CF ₅ NO ₂ 4148 C ₅ F ₇ H br Cl CSN NO ₂ 4149 CH ₃ H br H CO ₂ Et NO ₂ 4150 - ^ H br Cl CCl ₅ NO ₂ 4151 OMe H br H "" C = N NO ₂ 4152 H H   br H C5N NO ₂ 4153 CCl ₅ CCl ₅ CCl ₅ H H H CH ₅ CH ₅ CH ₅ H Cl H CF ₅ CF ₅ C = N NO ₂ NO ₂ JN v / 0 4,154 4,155 4,156 CCl ₅ H ' CH ₅ Cl CSN NO ₂ 4157 CCl ₅ H CH ₅ H CCl ₅ NO ₂ 4158 CCl ₅ H CH ₅ H CH ₅ NO ₂ Mp. 4159 CCl ₅ H CH ₅ H CO ₂ Et NO ₂ Mp. 4160 CCl ₅ H CH ₅ Cl CO ₂ Et NO ₂ Mp. 4161 CF ₂ CHF ₂ H CH ₅ F NO ₂ CF Mp. 4162 CF ₂ CHF ₂ H CH ₅ H CSN 4163 CF ₂ CHF ₂ H CH, br CF ₅ NO ₂ 4164

Table 4 (Port setting)

physics. constants

rci

4,165 4,166 4,167 4,168 4,169 4,170 4,171 4,172 4,173 4,174 4,175 4,176 4,177 4,178 4,179 4,180 4,181 4,182 4,183 4,184

CP ₂ CHP ₂

CP ₂ CHP ₂

CP ₂ CP ₃

CP ₂ CP ₃

CH,

CsN

OMe

CCl ₃

CCl ₃

CCl ₃

CCl ₃

CCl ₃

CCl ₃

C ₂ Cl ₅

CCl ₂ CHCl ₂

CP ₂ GHCl ₂

CP ₃

CH ₂ Cl

CCl ₃

H H H H H H

CH:

et "

CH,

CH ,. H

CH, Cl

CH ₃ CH ₃ CH,

CH CH

CH ₃ P

CsN H

CSN Cl

CSN H

CSN Cl

CsN H

P H

P Cl

P Cl

OCH ₃ H

OCH ₃ Cl

OEt Cl

SEt H '

CCl ₃

CP ₂ CHP ₂

CP ₃

CP ₃

CCl ₃ '

CP ₂ Cl

CHP ₂

CHCl ₂

CP ₃

CP,

CO ₂ Et

CH ₃

CP ₃

CCl ₃

CO ₂ Et

CP ₃

CP ₂ Cl

CH ₃

CP ₃

NO, NO, NO, NO, NO, Nu! NO, NO, NO, NOj NO, NO, NO, NO, NO, NO, NO, NO, NO, NO

Mp. Mp.

135-137 166-168

4.185 0- < 4.186. OCH.

CH, / CsN H CP

CH, NOp P CP-

NO

NO

4,187 -SEt

CH ₃ NO ₂ NO

4,188 cl

4.189 p

4,190 CP ₂ CP ₃

CP ₃ H Cl CP ₃ CH ₃ HHH Cl

CP, CP, CP ^

NOj

: no, NO

₂ letters 115-120

Table 5

^R 1 * 2 * 3 ^R 4 * 5 CF ₃ % ^R 10 physics. No. CCI H H H CF ₃ CO ₂ Et NO ₂ CH ₃ Constants rci 5.1 CCl ₃ H H Cl CF ₃ CSN NO ₂ CH ₃ 5.2 cci ₃ H H H CF ₃ C = N NO ₂ et 5.3 CCl ₃ H H Cl CF ₃ NO ₂ et 5.4 CF ₂ Cl H H H NO ₂ CF ₃ CH ₃ 5.5 CF ₂ Cl H H Cl CF ₃ NO ₂ et 5.6 cci ₃ H H H CH ₃ NO ₂ CH ₃ 5.7 CCl ₃ H H Cl CH ₃ NO ₂ CH ₃ 5.8 cci ₃ H .H H CCl ₃ NO ₂ CH ₃ 5.9 CCl ₃ H H- Cl CCl ₃ NO ₂ CH ₃ 5.10 CCl ₃ ' H H H CSN NO ₂ CH ₃ 5.1! cci ₃ H H Cl CHN NO ₂ CH ₃ - 5.12 cci ₃ H H H CO ₂ Et NO ₂ CH ₃ 5.13 CF, H H Cl CO ₂ Et NO ₂ CH, 5.14 CH ₃ CF, H H H NO ₂ CH ₃ 5.15 CCl ₃ CH ₃ H H NO ₂ CH ₃ 5.16 CCl ₃ CH ₃ H Cl NO ₂ CH ₃ Snp. 160-163 5.17 CCl ₃ CH ₃ H Cl NO ₂ CH ₃ Mp. 197-199 5.18 OMe CH ₃ H H NO ₂ CH ₃ Snp. 162-164 5.19 - me CH ₅ . H Cl NO ₅ CH, 5.20

H H

CCI,

NO ₀ Et

Table 5 (continued)

No.

"3

physics. constants

rci

5.22 CH ₃ H H P CCl ₃ NO ₂ CH ₃ 5.23 H H P CP ₂ Cl NO ₂ CH ₃ 5.24 CP ₂ CHP ₂ H H H CP ₃ NO ₂ CH ₃ 5.25 CP ₂ CHP ₂ H H Cl CP ₃ NO ₂ CH ₃ 5.26 CP ₂ CHP ₂ H H H CCl ₃ NO ₂ CH ₃ 5-27 CP ₂ CHF ₂ H H Cl CCl ₃ NO ₂ CH ₃ 5.28 CP ₂ CHF ₂ H H H CsN NO ₂ CH ₃ 5.29 CP ₂ CHP ₂ H H H CO ₂ Et NO ₂ CH ₃ 30.5 CP ₂ CP ₃ H H H CP ₃ NO ₂ CH, 5.31 CP ₂ CP ₃ H- H Cl CP ₃ NO ₂ CH ₃ 5-32 CP ₂ CP ₃ H H H CO ₂ Et NO ₂ CH ₃ 5:33 CP ₂ CP, H H H CsN NO ₂ CB ₃ 5:34 CP ₂ CHP ₂ H H H CP, NO ₂ et 5:35 CP ₂ CHP ₂ H ^ H Cl CP ₃ NO ₂ et 5:36 CP ₂ CP ₃ H H H CP ₃ NO ₂ et 5-37 CP ₂ CP ₃ H H Cl CP, NO ₂ et 5:38 CCl ₃ H Cl H NO ₂ CH ₃ 5-39 CCl ₃ H Cl Cl CP ₃ NO ₂ CH ₃ 5:40 CCl ₃ H Cl H . CP, NO ₂ et 5:41 CCl ₃ H Cl Cl CP ₃ NO ₂ bt 5:42 CCl ₃ H Cl H C = N NO ₂ CH ₃ 5-43 CCl ₃ H Cl Cl C = N NO ₂ CH ₃ 5:44 CCl ₃ . H Cl H CO ₂ Et NO ₂ CH ₃ 5:45 CCl ₃ H Cl Cl. CO ₂ Et NO ₂ CH, 5:46 CCl ₃ H Cl H CCl ₃ NO ₂ CH ₃ 5-47 CCl ₃ H Cl Cl CCl ₃ NO ₂ CH ₃ 5:48 CCl ₃ H Cl H CH ₃ NO ₂ CH ₃ 5:49 CCl ₃ H Cl H NO ₂ CP ₃ CH ₃ 5:50 CCl ₃ H Cl Cl NO ₂ CP ₃ CH ₃ 5:51 CP ₂ Cl H Cl H CP ₂ Cl NO ₂ nC ₃

Table 5 (Port setting)

^R 1 K ₂ Cl ^R 4 "5 ^R 6 physics. No. CF ₂ Cl H Cl Cl CF ₂ Cl NO ₂ R ₁₀ constants rci 5:52 CHCl ₂ H Cl H CF ₃ NO ₂ KC ₅ H ₇ 5:53 CHCl ₂ H Cl Cl CF ₃ NO ₂ CH ₃ 5:54 CCl ₂ CCl ₃ H Cl H CsN NO ₂ (Η, 5-55 CCl ₂ CCl ₃ H Cl Cl CO ₂ Bt NO ₂ CH ₃ 5-56 Cl H Cl H CCl ₃ NO ₂ bt 5:57 Cl H Cl Cl CHCl ₂ NO ₂ CH ₃ 5:58 CH ₃ CH ₃ Cl H CP ₂ CP ₃ NO ₂ CH ₃ 5:59 CH ₃ CH ₃ Cl Cl CH ₃ NO ₂ CH ₃ 5.60 CP ₂ CHF ₂ H Cl H- CP ₃ NO ₂ HC ₃ H ₇ 5.61 CF ₂ CHP ₂ H Cl Cl CP ₃ NO ₂ CH ₃ 5.62 CP ₂ CHP ₂ H Cl H CO ₂ Bt NO ₂ HC ₃ H ₇ 5.63 CP ₂ CHP ₂ H Cl Cl CO ₂ Bt NO ₂ CH ₃ 5.64 CP ₂ CHP ₂ H Cl H 0ΞΝ NO ₂ CH ₃ 5.65 CP ₂ CHP ₂ H Cl Cl CsN NO ₂ CH ₃ 5.66 CP ₂ CHF ₂ H Cl H CCl ₃ NO ₂ CH ₃ 5.67 CF ₂ CHP ₂ H Cl , Cl CCl ₃ NO ₂ CH ₃ · 5.68 CP ₂ CF ₃ H Cl H CP ₃ NO ₂ CH ₃ 5.69 CF ₂ CP ₃ H Cl Cl. CP ₃ NO ₂ CH ₃ 5.70 CF ₂ CP ₃ H Cl H CCl ₃ NO ₂ CH ₃ . 5-71 CF ₂ CP ₃ H Cl H CO ₂ Bt NO ₂ nC ₄ H ₉ 5.72 CP ₂ CP ₃ H Cl H CsN. NO ₂ CH ₃ 5.73 CF ₂ CHF ₂ H Cl H CF ₃ , NO ₂ CH ₃ 5.74 CF ₂ CHP ₂ H Cl Cl CF ₃ NO ₂ et 5.75 C ₄ F ₉ H Cl Cl CF ₃ NO ₂ n-C, H-, 5-76 C ₃ P ₇ H Cl H CP ₃ NO ₂ et 5.77- C ₃ F ₇ H Cl Cl CP ₃ NO ₂ CH ₃ 5.78 ° 7 ^F 15 H Cl Cl CP ₃ NO ₂ CH ₃ 5.79 CF ₂ CHClF H br Cl CP ₃ NO ₂ CH ₃ 5.80 CF ₃ H br H CF ₃ NO ₂ CH ₃ 5.81 CF, H Cl · CsN NO ₅ C ₂ H ₅ 5.82 CH,

Table 5 (Port setting)

-46- £ 60 ££ O

R ₂

physics. constants

rci

5.83 CP, H br H CO ₂ Et NO ₂ CHj 5.84 CPj H P Cl CO ₂ Bu NO ₂ CHj 5.85 C ₂ H ₅ H CHj H CF, NO ₂ CHj 5.86 C ₂ H ₅ H- CHj Cl CFj NO ₂ CHj 5.87 C ₂ H ₅ H CHj H CsN NO ₂ CHj 5.88 H CHj Cl CO ₂ Et NO ₂ CHj 5.89 CHj H CHj H CClj NO ₂ CHj 5.90 CHj H CHj Cl CHj NO ₂ CHj 5.91 -4 H P H CFj NO ₂ CHj 5-92 H P Cl CsN NO ₂ CHj 5.93 OCPj H et H CO ₂ Et NO ₂ CHj 5.94 Cl- (O) - H et Cl CCI, NO ₂ et

5.95 OCHJ H OCHjH

CP ₇

NO,

5.96 (O

SN H

CPr,

NO,

CP ₂ Cl CP ₂ Cl CP ₂ Cl

H H H

C5N Cl CSN H CsN Cl

CCI,

CH,

NO,

CO ₂ Et NO ₂

KO,

CHj CHj CHj

5,100 CH ₂ Cl H

CCI,

NO,

5.101 CClj

5.102 CClj

5.103 CCl ₃

5.104 CCl,

H H

CH-CH-,

CSN H

CSN Cl

H H

H H

CF, CP

3 ^N0 2

CO ₂ Et NO ₂ C = NOo

STILL,

CH ₃ CH,

Snp. 148-150 snp. 216-218

C. Biological Examples 1. Fungicidal Activity Example 1

Biomalzagar was mixed with the claimed compounds (Table 1) in concentrations of 2000 and 500 ppm of active ingredient. After solidification of the agar, inoculation was carried out with various Botrytis cinerea cultures that are benzimidazole and iprodione-sensitive. 20 μΙ each of a spore suspension was applied to the center of the agar plate. The experiments were evaluated 6 days after inoculation. The efficiency of the active ingredients is expressed in% compared to the control (agar medium without active substance).

Table 1

Botrytis cinerea, BCM and iprodione-sensitive (s) and -resistant (r) strain

connection Efficiency in% at ppm active ingredient 500 according to example no. s. r 2,000 s r

2.10

2-12

2-9

2-7

2-5

4-1

4-47

4-116

4-24

4-2

4-48

4-117

4-53

4-55

4-159

4-157

4-98

4-190

4-168

4-167

4-93

2-19

5-17

2-12

3-5

3-1

3-10

3-6

3-13

3-27

3-8

3-26

3-51

3-50

3-48 2-51 2-74 11-74 2-18 3-48 4-94 4-168

100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 1Ö0 100 100 100 100 100 100 100 100 100 100 100

100 100 100

80 100 100 100 100

80 100 100 100 100

50 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100

50

100

50

50

80

50

100

100

50

100

100

100

100

100

100

100

100

100

100

50

50

80

100

80

100

50

50

100

100

100th

100

100

100

100

100

100 100 100 100 100 100

100 100 100 100 100 100

control

Example 2

Biomalzagar was mixed with the claimed compounds (Table 2) in concentrations of 125.30 and 8 ppm respectively. After solidification of the agar, inoculation was carried out with Pseudocercosporella cultures (BCM-sensitive and BCM-resistant).

20 μΙ each of a spore suspension was applied to the center of the agar plate. The experiments were evaluated 6 days after inoculation. The efficiency of the active ingredients is expressed in% compared to the control (agar medium without active substance).

Table 2 a

Compound according to example no.

2.10

2.12

Efficiency over Pseudocercosporellaherpotrichoides

in% at ppm active ingredient (BCM: sensitive strain)

30 - 8

100 100 100 100 100 100

100 100 100 100 100 100

100 100 100 100 100 100

Continuation Table 2 a

connection > Efficiency over Pseudocercosporella herpotrichoides 30 8th 30. 8th BCM-resistant strain 30 8th connection in% at ppm active ingredient (BCM: sensitive strain) 80 100 100 '125 100 100 according to example no. according to example no. 125 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 4.1 • 100 100 80 100 100 100 100 100 4:47 3.8 100 100 100 100 .100 100 100 100 4116 3:50 100 100 100 100 100 100 100 100 4.24 1:32 100 80 - 100 100 100 100 100 4.2 1:48 100 100 80 100 100 100 -. - 4117 1179 100 100 80 100 100 - 100 100 4:51 3:48 100 80 - Ί00 100 100 100 100 4:53 2:46 100 100 100 100 100 100 - - 4:55 2:51 100 100 80 100 100 - 100 100 4159 2:50 100 100 - 100 100 100 - - 4157 1209 100 100 100 100 100 - - - 4190 1213 100 100 100 100 100 - 100 100 4167 1:46 100 100 100 100 100 100 100 100 4.93 1214 100 100 - 100 100 100   100 • 100 2.19 1192 100 100 - 100 100 100 100 100 5.17 1.92 100 100 - 100 100 100 100 100 3.5 1,268. 100 100  - 100 100   100 - - 3.1 1200 100. 100 100 100 - - 3.6 1139 100 100 - 100 100 - 3.13 1:49 100 100 - 100 100 - -   - ^ - · 3.27 2:56 100 80 - 100 100 - 3.8 2.7 100 100 100 100 100 - - - 3.26 4.94 100 100   100 100 100 - 100 1.00 3.9 4.93 100 0 100 4:48 2.77 100 0 4158 4.98 - ^v - Table 2t control 4168 control Efficiency vs Pseudocerosporella herpotrichoides in% at ppm active ingredient BCM-sensitive strain 125 , 100 100 100 100 100 100 100 100 100 100 100 .. 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Example 3

Vine plants grown from cuttings of the Plasmopara susceptible variety Muller-Thurgau were treated to drip point wet at the 4-leaf stage with aqueous suspensions of the claimed compounds. The use concentrations were 500, 250 and 125 mg of active ingredient per liter of spray mixture.

After the spray coating has dried, the PflaVizen were inoculated with a zoosporangia suspension of Plasmopara viticola and to runoff in a climate chamber at a temperature of about 20 ⁰ C. and adjusted to a relative humidity of about 100%. After 24 hours, the infected plants of the climate chamber were removed and placed in a greenhouse with a temperature of about 23 ° C and a humidity of about 80-90%.

After an incubation period of 7 days, the plants were placed overnight in the climatic chamber and brought the disease to the outbreak. Subsequently, the infestation evaluation took place. The degree of infestation was expressed in% of infected leaf area compared to the untreated, infected control plants and is shown in Table 3.

Table 3

Compound% Plasmppora viticola - infestation at ppm active ingredient

according to example no.

500 250

1.60 0 · 0

, 2.51 0 0 0

2.50 0 0 0

1,190 0 0 0

1.48, 0 0 0 1.179 0 0 0

1.213 0 .00 1.8. 0 "0 ' 0 1.46 0 0 0

1.214 0 0 0 1.643 0 0 0 1.192. 0 0 0

1.92 0 0 0 1.251 0 0. 0 1,250. 0 0 .0

1.49 0. 0 0

4.93 '. · 0 .0 0 2.77 "'0 · 0 0 4.98 0 0 .0

untreated. , ,

infected

Plants' - 100 "

Example 4

Apple pads (EM IX) were uniformly treated at the 4-leaf stage with the claimed compounds at the application levels of 500,250.125 mg drug / liter spray.

After drying of the drug coating plants with conidia of apple scab (Venturia inaequalis) were strongly inoculated and placed dripping wet in a climatic chamber whose temperature was about 22 ⁰ C and their relative humidity about 100%. After an infection time of 48 hours, the plants came into a greenhouse with about 18 ⁰ C and a relative humidity of

95-100%.»   , ·

After an incubation period of 14 days, the plants were examined for apple scab infestation (Venturia inaequalis). The assessment of the infestation was done as usual by inspection. The degree of infestation of the plants with apple scab was expressed in% of infected leaf area relative to untreated, infected plants and is shown in Table 4.

Table 4 <

Compound according to example no. % Scab infestation at mg active substance / liter spray mixture 500 250 0 o 125 1,209 1,213 0 0 100 0 0 untreated infected plants

Example 5

Wheat plants are strongly inoculated in the 3-leaf stage with conidia of wheat powdery mildew (Erysiphe graminis) and placed in a greenhouse at 20 ° C and a relative humidity of 90-95%. 3 days after inoculation, the plants are treated with the compounds and drug concentrations listed in Table 5. After an incubation period of 10 days, the plants are examined for infestation with wheat powdery mildew. The degree of infestation is expressed in% of infected leaf area, based on untreated infected control plants (= 100% infestation). The result is summarized in Table 5.

Table 5

Compound according to example no. leaf area affected with wheat powdery mildew in% at mg active substance / liter spray mixture 500 250 0 0 12.5 2.77 1.201 0 0 0 0 untreated infected plants 100

Examples

Cucumber plants (variety Delikateßj are strongly inoculated in the 2-leaf stage with a conidia suspension of cucumber powdery mildew (Erysiphe cichoracearum).) After a drying time of the spore suspension of 30 minutes, the plants are placed in a greenhouse at 22 ⁰ C and 90% relative humidity.

3 days after infection, the plants are treated with the compounds and active substance concentrations listed in Table 6.

After 10 days, the rating is done. The degree of infestation is expressed in% of infected leaf area, based on untreated, infected Kontro.llpflanzen (= 100% infestation). The result is summarized in Table 6.

Table 6

Connection . according to example no. leaf area affected with cucumber mildew in% at mg active substance / liter spray mixture 500 250 125 1201 o: o 0 untreated infected plants - 100

Example 7

Synergistic effect on the example of Iprodion cross-strip test (method in J. Gen. Microbiol., 126 (1981), page 1-7) in Petri dishes.

Synergistic relationships between different drugs can be determined in an in vitro experiment by the so-called cross-stripe test.

Filter paper strips (10 mm wide and 90 mm long) are uniformly wetted with the formulated active compounds of the formula I and the combination partner (iprodione) in various concentrations (about 200μΙ / strip) and on the fungus different species agar medium swept. 0.5 ml of suspension culture of the test organism (about 10 ⁵ -10 ⁶ conidia / 1 ml) were added to the agar previously in a liquid state per Petri dish. Each Petri dish contains a filter paper strip with the one representative of formula I and perpendicular to a second strip with the combination partner (iprodione) the drug concentrations are selected by appropriate preliminary experiments with the individual components so that they correspond to the respective test organism of the so-called minimum inhibitor concentration. after about 3 to 4 days of incubation of the petri plates at 22-25 ⁰ C, the zones of inhibition in the range of the intersecting test strips are diametrically measured and evaluated the inhibition zone as a measure of synergism.

Table 7

Cross-stripe test Test object: Botrytis cinerea

Active substances or combinations (Ex. No.)

4.117 iprodione -

Drug combinations of 4.117+ iprodione

2. Insecticidal action

a) b) · c) d)

a + c a + d 'b + c b + d

Conc. Active ingredient Hemm zones in mm ppm 500 0 250 0 500 8th ' 250 0 500 + 500 16 500 + 250 8th 250 + 500 10-12 250 + 250 6

Example 8 ·

Bean sprouts (Phaseolus v.) Heavily infested with spider mites (Tetranychus urticae, full population) were sprayed with the aqueous dilution of an emulsion concentrate containing 100 ppm of the respective active ingredient.

The mite mortality was checked after 7 days. 100% kill was made with the compounds of Example 1.643; 1,200; 1,251; 1,471; Scored 1-.481 and 1,291.

Example 9

Apple tree (Malus communis) heavily affected with fruit tree spider mites (Panonychus ulmi) were treated as in Example 1. *

The mite mortality was checked after 8 days. 100% kill was achieved with the compounds of Example 1.92; Scored 1,200 and 1,481.

Example 10

Ara beans (Vivia faba) heavily populated with cowpea aphid (Aphis craccivora) were sprayed with aqueous dilutions of wettable powder concentrates containing 1000 ppm active ingredient up to the initial dripping stage. The mortality of the aphids was determined after 3 days. A 100% kill could be achieved with the compounds of Example 1.46,1.214,1.643,1.192,1.200,1.201,1.250,1.291 and 1.471.

Example 11

Bean plants heavily populated with white fly (Trialeurodes vaporariorum) were sprayed with aqueous suspensions of wettable powder concentrates (1 000 ppm active substance content) until the beginning of dripping. After setting up the plants in the greenhouse, after 14 days, the microscopic control with the result of each 100% mortality in the preparations with the active ingredients of Examples 2.51.2.50.1.189 and 1.200 take place.

Example 12

On the inside of the lid and the bottom of a Petri dish, in each case 1 ml of the formulation to be tested is applied emulsified in water uniformly and, after the coating has dried, in each case 10 imaginings of the house fly (Musca domestica) are entered. After closing the dish, they are stored at room temperature and after 3 hours the mortality of the experimental animals is determined.

At 10OOppm (based on the active ingredient content) the preparations showed 1,255.1.2.1.256, .1.8.1.298.1.214.1.643,1.192,1.92, 1,442,1,140,1.267,1.268,1.200,1,201,1.222,1.223,1.197, 1,215,1.10,1.38,1.4,1,139, 3.28,1.251,1.1,1.250,1.101,1,291,1,471, 1,470,1,481 and 1,284 a 100% effect.

Example 13

Petri dishes treated as described in example 5 are each replaced by 10 larvae (L4) of the German cockroach (Blattella germanica), the dishes are closed and the mortality of the test animals is determined for 5 days.

At 1000 ppm (based on the content of active ingredient), the preparations showed 1,194.1, 125.1.8, 2.198, 643.1, 442.1, 200, 1.222, 4.1, 1,139, 1251, 1284 and 1.2 100% activity. "-

Claims (6)

-1- ZÖ3ZZU Claims: 1. Pesticide, characterized in that it is a compound of formula I or its salts, .λ (D R ₁ and R _{2 are} independently hydrogen; Halogen, cyano; (C ₁ -C ₈ ) -Alky !; (C ₁ -Cs) -HaIOaIkVl; (C ₁ -Cs) -alkyl which is monosubstituted or disubstituted by nitro, cyano, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ -alkylthio or -N (R ₇ ) (R ₈ ) is _(C3-C8) cycloalkyl which may be substituted by (dC ₄₎ -alkyl, (C ₂ -C ₄₎ - 'Alkenyl; (C ₂ -C ₄ ) -halpalkenyl; (C ₃ -C ₄ -alkyl) (Cy-CJ-haloalkynyl; _(C5-C6) -Cycloalkenyi; a group -N (R ₇ ) (R ₈ ); (C 1 -C ₈ ) -alkylthio; (dC ₈ ) alkoxy; (C ₁ -C ₈ ) - haloalkoxy; (C ₁ -C 6) alkylsulfonyl; phenyl optionally substituted by halogen, nitro, cyano, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄₎ -alkoxy, (C ₁ -C ₄ ) -alkoxy, (dC ₄₎ -alkylthio or (C ₁ -C ₄ J-HaIOaIkYl groups, or phenoxy optionally substituted by halogen, NO _2, (C ₁ -C ₄ J--alkyl, (d-CJ haloalkyl or (C ₁ J -C ₄ -alkoxy group; R ₃ is hydrogen, halogen, cyano, nitro, (Cr-CsJ-alkyl, (d-Cs) -haloalkyl, (C ₂ -C ₄₎ alkenyl, (C ₂ -C ₄ ) Haloalkenyl, phenyl which is optionally substituted by halogen, nitro, cyano, (C ₁ -C ₄ -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ -alkyl) or (C ₁ -C ₄ -haloalkyl or phenoxy which is optionally substituted by halogen NO ₂ , (C ₁ -C ₄ alkyl group, (C ₁ -C ₄ alkylthioalkyl, C ₁ -C ₄ alkylene; R _{4 is} hydrogen, halogen, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₆ -alkylthio, a group N (R ₇ (R ₈ ) or phenoxy which may be substituted by halogen; R ₅ is (C ₁ -C ₄ J--alkyl, (d-CGJ alkoxycarbonyl, (dC ₄ alkenyloxy) carbonyl, -CO ₂ H (C ₃ -C ₄ -Alkinyloxyjcarbonyl; (Ci-Cj-Haloalkoxyjcarbonyl; (Cr-Ct-Haloalkenylyloxyjcarbonyl; (Qr-Ct-Haloalkinyloxyjcarbonyl; -CON (R ₇ ) (R ₈ ); , · (C 1 -C ₄ ) alkylcarbonyl; (C ₂ -C ₄ -haloalkylcarbonyl; (C ₂ -C ₄ -haloalkenyl) carbonyl, (C ₃ -C ₄ -haloalkynyl-1-carbonyl, S (O) _n R ₉ ; S (O) _n OR ₉ or S (O) _n N (R ₇ ) (R ₈ ); halogen; cyano, NiIrO (C ₁ -C ₄ ) haloalkoxy; (d-CtJ-haloalkyl; formyl; S (OJnR ₉ ; S (S); O) _n OR ₉ or S (O) _n N (R ₇ ) (R ₈ ); η is one of the numbers 0,1 or 2; R _{6 is} NO ₂ or CF ₃ ; R ₇ and R ₈ independently of one another are hydrogen, (C ₁ -C ₄ -alkyl) (C ₃ -C ₇ -alkylcycloalkyl which may be substituted by (C ₁ -C ₄ ) -alkyl; or phenyl which may be replaced by halogen (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄₎ -alkyl, (C ₁ -C ₄ ) -alkoxy (C ₁ -C ₄ -alkylthio, nitro and cyano may be substituted; R ₉ (C ₁ -C ₄ J-AlKyl; (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl or (C ₃ -C ₇ ) -cycloalkyl, which may be substituted by (C ₁ -C ₄ ) -alkyl; R 2 independently of one another are hydrogen; (C ₁ -C ₄ ) -alkyl (C ₃ -C ₇ -cycloalkyl) which may be substituted by (C ₁ -C ₄ -alkyl ₎ (C ₁ -C ₄ -alkoxy-carbonyl, (C ₁ -C ₄ -alkyl-carbonyl (C ₁ -C ₄ -alkoxy J is phenyl optionally substituted by halogen, nitro, cyano, (C ₁ -C ₄ J--alkyl, (C ₁ -C ₄ J -alkoxy, (Ci-C ₄₎ alkylthio or (C 1 -C ₄ ) -haloalkyl, and X represents one of the groups -NR ₁₀ -NR ₁₀ , -NR ₁₀ - or -O-, with the proviso that those compounds of the formula I in which X represents a group -NR ₁₀ - and R _{5 is} CF ₃ or NO ₂ , except are, in an effective amount besides suitable formulation auxiliaries. 2. Pesticidal composition according to claim 1, characterized in that it contains compounds of formula I, R _{1 is} hydrogen; Halogen; cyano; (C ₁ -C ₈ J alkyl); (C ₁ -C ₈ J-HaIOaIkYl; (C ₁ -C ₈ -alkyl-J, which is a-or disubstituted by (C ₁ -C ₄ -alkoxy or J (dC ₄₎ alkylthio;. (C ₃ -C ₈ J-CyClOaIkYl, which may be substituted by (C ₁ -C ₄ -alkyl-J (dC ₈₎ alkylthio; (C ₁ -C ₈ -alkoxy J; (d-CsJ-alkylsulfinyl ( d-CsJ-alkylsulfonyl; phenyl which is optionally mono- or polysubstituted by halogen and / or mono- or trisubstituted by nitro, cyano, (C ₁ -C ₄ -alkyl), (C ₁ -C ₄ ) -alkoxy or (C ₁ -C ₄ ) - v is haloalkyl substituted, R _{2 is} the meaning of R ₁ except optionally substituted phenyl, R _{3 is} hydrogen; Halogen; cyano; nitro; (C ₁ -C ₈ ) -alkyl, (C ₁ -Cs) -HaIOalkyl or phenoxy, which is optionally substituted once to three times by halogen NO ₂ , (C ₁ -C) -alkyl, (C ₁ -C ₈ -haloalkyl, or (C i C ₄ ) alkoxy is substituted; R _{4 is} hydrogen; Halogen; (C ₁ -C ₄ -alkoxy; R _{5 is} (C ₁ -Q) -alkyl, (C ₁ -C ₄ -alkoxy) carbonyl, -CO ₂ H; -CON (R ₇ ) (R ₈ ); (C ₁ -C ₄ -AlkyDcarbonyl; (Cy-d-HaloalkylJ-carbonyl; cyano, halogen, nitro or S (O) _n N (R ₇₎ (R _8); η one of the numbers 0,1 or 2; R _{6 is} NO ₂ or CF ₃ ; R ₇ and R _{8 are} independently hydrogen; (C ₁ -C ₄ -alkyl) (C ₃ -C ₇ -cycloalkyl) which may be substituted by (C ₁ -C ₄ ) -alkyl, or phenyl which is mono- to trisubstituted by halogen, (C ₁ -) C ₄ -alkyl, (C ₁ -C ₄ ) -haloalkyl or (C ₁ -CJ -alkoxy) may be substituted; R independently of one another are hydrogen; (C ₁ -C ₄ ) -alkyl; and X is one of the groups -NR ₁₀ -NR ₁₀ or-NR ₁₀ - or-O- mean. 3. Pesticidal composition according to claim 1, characterized in that it contains compounds of the formula I, wherein R ₁ (C ₁ -Cs) -HaIOalkyl, (C ₁ -C ₄ -alkyl) (C ₃ -Ce) -cycloalkyl, phenyl or phenyl which is substituted as indicated above, in particular of which (Cr-C ₈ ) -haloalkyl, R _{2 is} H or (d-CJ-alkyl, R _{3 is} H or halogen, R _{4 is} H or halogen, R _{5 is} (C 1 -C 6 -alkoxycarbonyl, cyano; (C 1 -C 6 -haloalkoxy, (C 1 -C ₆ -haloalkyl or chloro, R 6NO ₂ and X = NH or -O-. 4. Fungicidal agent, characterized in that it contains a compound of formula I or its salt of claims 1, 2 or 3 in an effective amount in addition to suitable formulation auxiliaries. 5. Use of the pesticide according to claim 1, 2 or 3, characterized in that it is used for controlling animal pests or harmful fungi. A method for controlling animal pests or harmful fungi, characterized in that an effective amount of the pest-combating agent according to claims 1, 2 or 3 is applied to these or the plants or cultivated areas which they infest.