Substituted pyrimidines, processes for their preparation, and their use as pesticides and fungicides

The invention relates to novel substituted 4-amino- and 4-alkoxypyrimidines, to processes for their preparation and to their use as pesticides, in particular as insecticides, acaricides and fungicides.

It has already been disclosed that certain substituted 4-aminopyrimidines have a good fungicidal, acaricidal and insecticidal activity (cf. EP-A-57,440, EP-A-196,524, EP-A-264,217, EP-A-276,406, EP-A-323,757, EP-A-326,328, EP-A-326,329, EP-A-326,330, EP-A-356,158, EP-A-370,704, EP-A-411,634, EP-A-424,125, EP-A-452,002, EP-A-459,611, EP-A-447,891). However, the biological activity of these compounds is not satisfactory in all fields of application, in particular when low dosage rates and concentrations are used.

Novel substituted 4-amino- and 4-alkoxypyrimidines of the formula I have been found,

in which

R

1

is hydrogen, halogen, (C

1

-C

4

)-alkyl or (C

3

-C

6

)-cycloalkyl,

R

2

is hydrogen, (C

1

-C

4

)-alkyl, halogen (C

1

-C

4

)-halo-alkyl, (C

1

-C

4

)-alkoxy, (C

1

-C

4

)-haloalkoxy, (C

1

-C

4

)-alkoxy-(C

1

-C

4

)-alkyl, (C

1

-C

4

)-alkylthio, (C

1

-C

4

)-alkylthio-(C

1

-C

4

)-alkyl, (C

1

-C

4

)-alkylamino or di-(C

1

-C

4

)-alkylamino,

R

3

is hydrogen, (C

1

-C

4

)-alkyl, (C

1

-C

4

)-alkoxy, (C

1

-C

4

)-haloalkoxy, halogen, (C

1

-C

4

)-alkylthio, amino, (C

1

-C

4

)-alkylamino or di-(C

1

-C

4

)-alkylamino or

R

2

and R

3

together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered isocyclic ring which, if it is a 5-membered ring, can contain an oxygen or sulfur atom in place of CH

2

and which is optionally substituted by 1, 2 or 3 identical or different radicals, these radicals being (C

1

-C

4

)-alkyl, (C

1

-C

4

)-alkoxy, (C

1

-C

4

)-halo-alkyl, preferably trifluoromethyl, (C

1

-C

4

)-halo-alkoxy and/or halogen, or

R

2

and R

3

together with the carbon atoms to which they are bonded form a saturated 5-, 6- or 7-membered isocyclic ring which can contain an oxygen or sulfur atom in place of CH

2

and which is optionally substituted by 1, 2 or 3 (C

1

-C

4

)-alkyl groups,

X is NH or oxygen,

E is a direct bond or a straight-chain or branched (C

1

-C

4

)-alkanediyl group, preferably a direct bond,

Q has the meaning Q

1

and

Q

1

is a cycloalkyl group of the formula II

in which n is an integer from 2 to 7,

R

4

and R

5

are identical or different and are in each case hydrogen, (C

1

-C

12

)-alkyl, (C

3

-C

8

)-cycloalkyl, (C

3

-C

8

)-cyclo alkyl-(C

1

-C

4

)-alkyl, (C

1

-C

8

)-alkoxy, (C

3

-C

8

)-cyclo-alkoxy, (C

1

-C

4

)-alkoxy-(C

1

-C

4

)-alkyl, (C

3

-C

8

)-cyclo-alkyl-(C

1

-C

4

)-alkoxy, tri-(C

1

-C

8

)-alkylsilyl, preferably dimethyl-(C

1

-C

8

)-alkylsilyl or tri-ehtylsilyl, di-(C

1

-C

8

)-alkyl-(C

3

-C

8

)-cycloalkyl-silyl, preferably dimethylcyclohexylsilyl, di-(C

1

-C

8

)-alkyl (phenyl-(C

1

-C

4

)-alkyl)-silyl, preferably dimethyl-(phenyl-(C

1

-C

4

)-alkyl)silyl, di-(C

1

-C

8

)-alkyl-(C

1

-C

4

)-haloalkylsilyl, preferably dimethyl-(C

1

-C

4

)-haloalkylsilyl, dimethylphenyl-silyl, (C

1

-C

4

)-haloalkyl, halogen, (C

1

-C

4

)-haloalkoxy, heteroaryl, phenyl, phenyl-(C

1

-C

4

)-alkyl, benzyloxy, benxzyloxy-(C

1

-C

4

)-alkyl, benzylthio, phenylthio or phenoxy, it being possible for the phenyl rings in the seven last-mentioned radicals to be unsubstituted or provided with one or two substituents and these substituents are identical or different and can be in each case (C

1

-C

8

)-alkyl, (C

3

-C

8

)-cycloalkyl, (C

1

-C

4

)-haloalkyl, preferably trifluoromethyl, halogen, (C

1

-C

4

)-dialkylamino, (C

1

-C

4

)-alkylthio, (C

1

-C

8

)-alkoxy, (C

1

-C

4

)-haloalkoxy, (C

1

-C

4

)-alkoxy-(C

1

-C

4

)-alkoxy, H

5

C

2

-O-[CH

2

-CH

2

-O-]

x

, 2-(tetrahydro-2H-pyran-2-yloxy)-ethoxy, (C

2

-C

8

)-alkenyl, (C

2

-C

8

)-alkynyl, benzyloxy which in the phenyl radical optionally carries one or two identical or different substituents selected from the group comprising (C

1

-C

4

)-alkyl, (C

1

-C

4

)-haloalkyl, (C

1

-C

4

)-alkoxy, (C

1

-C

4

)-haloalkoxy and halogen, or tri-(C

1

-C

4

)-alkylsilylmethoxy, preferably dimethyl-(C

1

-C

4

)-alkylsilylmethoxy, (C

3

-C

8

)-cycloalkyl-(C

1

-C

4

)-alkoxy, 1,3-dioxolan-2-ylmethoxy, tetrahydro-furan-2-ylmethoxy or tetrahydro-2H-pyran-2-ylmethoxy, where, both, R

4

and R

5

do not coincidentally denote hydrogen, and where, in two adjacent substituents which are identical or different and are selected from the group comprising (C

1

-C

8

)-alkyl and (C

1

-C

8

)-alkoxy, in each case one hydrogen atom can be replaced by a joint carbon-carbon bond which links these two substituents, or

R

4

and R

5

together with the cycloalkyl group form a 3-8-membered spirocyclic, preferably saturated spirocyclic, ring system which can contain oxygen or sulfur in place of one or two CH

2

groups or

R

4

and R

5

together with the carbon atoms carrying them form a fused 5- or 6-membered, preferably saturated isocycle, in particular a cyclopentane or cyclohexane system,

X is 2, 3 or 4, preferably 2, or

Q has the meaning Q

2

and

Q

2

is a group of the formula III

in which

R

6

is a group of the formula Z-W and Z is a direct bond or carbonyl or sulfonyl and W is an aryl or heteroaryl group which can be unsubstituted or provided with one or two substituents and these substituents are identical or different and are in each case (C

1

-C

8

)-alkyl, (C

3

-C

8

)-cycloalkyl, trifluoromethyl, halogen (C

1

-C

4

)-alkoxy, (C

1

-C

4

)-dialkylamino or (C

1

-C

4

)-alkylthio.

If Q has the meaning Q

1

, R

2

and R

3

together with the carbon atoms carrying them form an unsaturated 6-membered isocyclic ring and R

4

and R

5

form a fused 5- or 6-membered ring, then the meaning 5-membered ring is preferred for the two last-mentioned radicals.

If Q has meaning Q

1

, and R

2

and R

3

together with the carbon atoms carrying them form a furan or thiophene system, then Q

1

is preferably not (C

3

-C

8

)-cycloalkyl which is optionally substituted and the substituents are in particular alkyl such as (C

1

-C

4

)-alkyl, alkoxy such as (C

1

-C

4

)-alkoxy, haloalkyl such as (C

1

-C

4

)-haloalkyl, haloalkoxy such as (C

1

-C

4

)-haloalkoxy or halogen.

Preferred compounds of the formula I are those in which

R

1

is hydrogen, methyl or cyclopropyl,

R

2

is (C

1

-C

4

)-alkyl, chlorine, methoxy, ethoxy or methoxymethyl,

R

3

is hydrogen, (C

1

-C

3

)-alkyl, methoxy, ethoxy or halogen or

R

2

and R

3

together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered ring which can contain an oxygen or sulfur atom, or R

2

and R

3

together with the carbon atoms to which they are bonded form a saturated 5- or 6-membered ring which can contain a sulfur atom,

Q has the meaning Q

1

or Q

2

, in particular those compounds of the formula I in which

R

1

is hydrogen or methyl,

R

2

is methyl, ethyl, methoxy, ethoxy or methoxy-methyl,

R

3

is methyl, ethyl, methoxy, chlorine or bromine, or

R

2

and R

3

together with the carbon atoms to which they are bonded form the quinazoline system, or

R

2

and R

3

together with the carbon atoms to which they are bonded form a saturated 6-membered ring which can contain a sulfur atom and

Q has the meaning Q

1

or Q

2

, preferably those compounds of the formula I in which

E is a direct bond,

R

1

is hydrogen,

R

2

is methyl, ethyl or methoxymethyl,

R

3

is chlorine, bromine or methoxy or

R

2

and R

3

together with the carbon atoms to which they are bonded form the quinazoline system which can be substituted by fluorine, chlorine, bromine or methyl, or

R

2

and R

3

together with the pyrimidine ring form the 5,6,7,8-tetrahydroquinazoline system or the 5,6-dihydro-7H-thiopyrano[2,3-d]pyrimidine or the 5,6-dihydro-8H-thiopyrano[3,4-d]pyrimidine system

and

Q has the meaning Q

1

or Q

2

.

Very particularly preferred compounds of the formula I are those in which

E is a direct bond,

R

1

is hydrogen,

R

2

is methoxymethyl and R

3

is methoxy or

R

2

is methyl or ethyl and R

3

is chlorine or bromine or

R

2

and R

3

together with the carbon atom to which they are bonded form a quinazoline system which is substituted by fluorine, chlorine or methyl, or form a 5,6,7,8-tetrahydroquinazoline system and

Q has the meaning Q

1

, in particular those compounds of the formula I in which

E is a direct bond,

R

1

is hydrogen,

R

2

is methoxymethyl and R

3

is methoxy or

R

2

is ethyl and R

3

is chlorine or

R

2

and R

3

together with the carbon atom to which they are bonded form a quinazoline or a 5,6,7,8-tetrahydroquinazoline system and

Q is a cycloalkyl group of the formula II which is substituted in the 3- or 4-position and in which

n is 4 or 5,

R

4

is (C

3

-C

8

)-alkyl, cyclopentyl, cyclohexyl, phenyl or phenoxy, it being possible for the two last-mentioned radicals to be unsubstituted or provided with one or two substituents which can be identical or different and which are fluorine chlorine, bromine, (C

1

-C

4

)-alkyl, (C

1

-C

4

)-alkoxy, trifluoromethyl, (C

1

-C

2

)-haloalkoxy, cyclohexyl, 2-ethoxyethoxy, methylthio or dimethylamino, and

R

5

is hydrogen.

Other very particularly preferred compounds of the formula I are those in which

E is a direct bond,

R

1

is hydrogen,

R

2

is methoxymethyl and R

3

is methoxy or

R

2

is ethyl and R

3

is chlorine, or

R

2

and R

3

together with the carbon atoms to which they are bonded form a quinazoline or a 5,6,7,8-tetrahydroquinazoline system,

Q has the meaning Q

1

and

Q

1

is cyclohexyl which is substituted in the 4-position, and E and the substituent in the 4-position of the cyclohexyl are in the cis-position relative to each other,

R

4

is as defined above and

R

5

is preferably hydrogen.

In the above formula I, “halogen” is to be understood as meaning a fluorine, chlorine, bromine or iodine atom, preferably a fluorine, chorine or bromine atom, the term “(C

1

-C

4

)-alkyl” is to be understood as meaning an unbranched or branched hydrocarbon radical having 1-4 carbon atoms such as, for example, the methyl, ehtyl, propyl, 1-methylethyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl radical, the term “(C

1

-C

8

)-alkyl” is to be understood as meaning the abovementioned alkyl radicals and, for example, the pentyl, 2methylbutyl or 1,1-dimethylpropyl radical, the hexyl, heptyl, octyl radical, or 1,1,3,3-tetramethylbutyl; the term “(C

1

-C

12

)-alkyl” is to be understood as meaning the abovementioned alkyl radicals as well as, for example, the nonyl, decyl, undecyl or dodecyl radical; the term “(C

3

-C

8

)-cycloalkyl” is to be understood as meaning the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl group; the term “(C

1

-C

4

)-alkoxy” is to be understood as meaning an alkoxy group whose hydrocarbon radical has the meaning given for the term “(C

1

-C

4

)-alkyl”; the term “(C

3

-C

8

)-cycloalkoxy” is to be understood as meaning a cycloalkoxy group whose hydrocarbon radical has the meaning given under “(C

3

-C

8

)-cycloalkyl”; the term “(C

1

-C

4

)-alkylthio” is to be understood as meaning an alkylthio group whose hydrocarbon radical has the meaning given for the term “(C

1

-C

4

)-alkyl”; the term “(C

1

-C

4

)-haloalkoxy” is to be understood as meaning a haloalkoxy group whose halohydrocarbon radical has the meaning given for the term “(C

1

-C

4

)-haloalkyl”, the term “(C

1

-C

4

)-alkoxy-(C

1

-C

4

)-alkyl” is to be understood as meaning, for example, a 1-methoxyethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a methoxymethyl or ethoxymethyl group, a 3-methoxypropyl group or a 4-butoxybutyl group; the term “(C

1

-C

4

)-alkylthio-(C

1

-C

4

)-alkyl” is to be understood as meaning, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or 3-methylthiopropyl; the term “(C

1

-C

4

)-alkylamino” is to be understood as meaning an alkylamino group whose hydrocarbon radical has the meaning given under the term “(C

1

-C

4

)-alkyl”, preferably the ethyl and methylamino group; the term “di-(C

1

-C

4

)-alkylamino” is to be understood as meaning a dialkylamino group whose hydrocarbon radicals have the meaning given under the term “(C

1

-C

4

)-alkyl”, preferably the dimethyl and diethylamino group; the term “(C

1

-C

4

)-haloalkyl” is to be understood as meaning an alkyl group mentioned under the term “(C

1

-C

4

)-alkyl”, in which one or more hydrogen atoms is replaced by the abovementioned halogen atoms, preferably chlorine or fluorine, such as, for example, the trifluoromethyl group, the 2,2,2-trifluoroethyl group, the chloromethyl or the fluoromethyl group, the difluoro-methyl group or the 1,1,2,2-tetrafluoroethyl group; the term (C

3

-C

8

)-cycloalkyl-(C

2

-C

4

)-alkyl” is to be understood as meaning one of the abovementioned (C

1

-C

4

)-alkyl groups which is substituted by one of the abovementioned (C

3

-C

8

)-cycloalkyl groups, for example cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, cyclohexylbutyl or 1-cyclohexyl-1-methyl-ethyl; the term “phenyl-(C

1

-C

4

)-alkyl” is to be understood as meaning one of the abovementioned (C

1

-C

4

)-alkyl groups which is substituted by a phenyl group, for example the benzyl group, the 2-phenylethyl group, the 1-phenylethyl group, the 1-mehtyl-1-phenylethyl group, the 3-phenylpropyl group, the 4-phenylbutyl group or the 2-methyl-2-phenylethyl group; the term “aryl” is to be understood as meaning, for example, phenyl, naphthyl or biphenylyl, preferably phenyl; the term “heteroaryl” is to be understood as meaning an aryl radical in which at least one CH group is replaced by N and/or at least two adjacent CH groups are replaced by S, NH or O; the term “benzyloxy-(C

1

-C

4

)-alkyl” is to be understood as meaning a (C

1

-C

4

)-alkyl group which has the abovementioned meanings and which is substituted by a benzyloxy group, for example the benzyloxymethyl or the 2-(benzyloxy)-ethyl group; the term “(C

3

-C

8

)-cycloalkyl-(C

1

-C

4

)-alkoxy” is to be understood as maning a (C

1

-C

4

)-alkoxy group which has the abovementioned meanings and which is substituted by a (C

3

-C

8

)-cycloalkyl group which has the abovementioned meanings, for example the cyclopropylmethyl or the cyclohexylmethyl group; the term “tri-(C

1

-C

8

)-alkylsilyl” is to be understood as meaning a trialkylsilyl group which carries preferably two methyl groups and one (C

1

-C

8

)-alkyl group having the abovementioned meanings, for example the trimethylsilyl, the dimethylethylsilyl or the dimethyloctylsilyl group; the term “di-(C

1

-C

8

)-alkyl-(C

1

-C

4

)-haloalkylsilyl” is to be understood as meaning a silyl radical which carries preferably two methyl groups and one (C

1

-C

4

)-haloalkyl radical having the meanings given under the term (C

1

-C

4

)-haloalkyl, for example the dimethyl-3,3,3-trifluoropropylsilyl radical; the term “(C

1

-C

4

)-alkoxy-(C

1

-C

4

)-alkoxy” is to be understood as meaning, for example, the ethoxymethoxy, 2-ethoxyethoxy, 2-butoxyethoxy or 2-methoxyethoxy group; the term “(C

2

-C

8

)-alkenyl” is to be understood as meaning, for example, the allyl, 1-methylallyl, 2butenyl or 3-methyl-2-butenyl group; the term “(C

2

-C

8

)-alkynyl” is to be understood as meaning, for example, the propargyl, 2-butynyl or 2-pentynyl group; the term “tri-(C

1

-C

4

)-alkylsilylmethoxy” is to be understood as meaning a trialkylsilylmethoxy radical which has preferably 2 methyl groups and in which the (C

1

-C

4

)-alkyl group has the abovementioned meanings; and the term “di-(C

1

-C

8

)-alkyl-phenyl-(C

1

-C

4

)-alkylsilyl” is to be understood as meaning a trialkylsilyl radical which has preferably two methyl groups and in which one alkyl group has the meanings mentioned above for the term “phenyl-(C

1

-C

4

)-alkyl”, preferably the dimethylbenzylsilyl group.

What has been explained above applies correspondingly to homologues or radicals derived thereof.

The present invention relates to the compounds of the formula I in the form of the free base or of an acid addition salt. Acids which can be used for salt formatoin are inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, or organic acids such as formic acid, acetic acid, propionic acid, malonic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid.

Some of the compounds of the formula I have one or more asymmetric carbon atoms. Racemates and diastereomers can therefore occur. The invention embraces the pure isomers as well as their mixtures. The diastereomer mixtures can be resolved into the components by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be resolved to give the enantiomers by conventional methods, for example by salt formation with an optically active acid, separation of the diasteromeric salts and liberation of the pure enantiomers by means of a base.

If Q

1

is a cycloalkyl group of the formula II and n is 4, 5 or 6, preferably 5, then E and a radical R

4

or R

5

which is preferably in the 4-position if n=5 are preferably in the cis-configuration relative to each other.

The invention furthermore relates to a process for the preparation of compounds of the formula I, which comprises reacting a compound of the formula IV

in which R

1

, R

2

are as defined in formula I and Z is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, with a nucleophile of the formula V

HX−E−Q (V)

in which X, E and Q are as defined in formula I and, if R

3

is hydrogen, the resulting compounds of the formula I are optionally chlorinated or brominated on carbon atom 5 of the pyrimidine.

The above mentioned substitution reaction is known in principle. The leaving group Z can be varied within wide limits and can be, for example, a halogen atom such as fluorine, chlorine, bromine or iodine, or alkylthio such as methyl- or ethylthio, or alkanesulfonyloxy such as methane-, trifluoromethane- or ethanesulfonyloxy, or arylsulfonyloxy such as benxenesulfonyloxy or toluenesulfonyloxy, or alkylsulfonyl such as methyl- or ethylsulfonyl, or arylsulfonyl such as phenyl- or toluenesulfonyl.

The abovementioned reaction is carried out in a temperature range of 20-150° C., expediently in the presence of a base and if appropriate in an inert organic solvent such as N,N-dimethylformamide, N,N-diemthylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one, dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene. Mixtures of the solvents mentioned can also be used.

In the event that X is oxygen, then suitable bases are, for example, carbonates, hydrogen carbonates, amides or hydrides of alkali metals or alkaline earth metals such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium amide or sodium hydride, and in the event that X is NH, they are, for example, carbonates, hydrogen carbonates, hydroxides, amides or hydrides of alkali metals or alkaline earth metals such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium hydroxide, sodium amide or sodium hydride, or organic bases such as triethylamine or pyridine. A second equivalent of an amine V can also be used as auxiliary base.

The starting compounds of the formula IV can be prepared by processes which are analogous to known processes. The starting materials used are acetoacetic ester derivatives which are converted into the halopyrimidines via the corresponding hydroxypyrimidines:

Furthermore, the starting compounds of the formula IV can be obtained from malonic ester derivatives in analogy to known processes:

In the event that X is oxygen, the nucleophiles of the formula V, which are required as starting materials, can be prepared by known processes, for example by reducing a carbonyl group with a suitable reducing agent, for example a complex metal hydride or, in the case of an aldehyde or ketone, also using hydrogen and a hydrogenation catalyst. Other possibilities are the reaction of an organometal compound with a carbonyl group or an oxirane. To synthesize cyclohexanol derivatives, it is also possible to react suitable substituted phenols with hydrogen in the presence of a hydrogenation catalyst.

In the event that X is NH, the nucleophiles of the formula V, which are required as starting materials, can also be prepared by known methods, for example reduction of an oxime or of a nitrile with a suitable reducing agent, for example a complex metal hydride or hydrogen in the presence of a hydrogenation catalyst, reductive amination or Leuckart-Wallach reaction of an aldehyde or ketone or Gabriel reaction of an alkyl halide or alkyl tosylate. To synthesize cyclohexylamine derivatives, it is also possible to react suitable substituted anilines with hydrogen in the presence of a hydrogenation catalyst.

The compounds of the formula I in which R

3

is halogen can be halogenated by known processes.

In the case of the 5-chloro derivatives, substances which can be used are, for example, elemental chlorine, sodium hypochlorite, sulfuryl chloride or N-chlorosuccinimide, and particularly suitable for the bromination are elemental bromine or N-bromosuccinimide. Examples of suitable solvents are dichloromethane, chloroform or glacial acetic acid.

The active ingredients are suitable for controlling animal pests, in particular insects, arachnids, helminths and molluscs, very particularly preferably for controlling insects and arachnids, which can be found in agriculture, in livestock breeding, in forests, in the protection of stored goods and materials as well as in the field of hygiene, and they are well tolerated by plants and have a favorable toxicity to warm-blooded species. They are active against normally-sensitive and resistant species and against all or some stages of development. The abovementioned pests include:

From the order of the Acarina, for example

Acarus siro

, Agras spp., Ornithodoros spp.,

Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora

, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp,. Tarsonemus spp.,

Bryobia praetiosa

, Panonychus spp,. Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp.

From the order of the Isopoda, for example,

Oniscus asellus, Armadillidium vulgare

and

Porcellio scaber.

From the order of the Diplopoda, for example,

Blaniulus guttulatus.

From the order of the Chilopoda, for example,

Geophilus carpohagus

and Scutigera spp.

From the order of the Symphyla, for example,

Scutigerella immaculata.

From the order of the Thysanura, for example,

Lepisma saccharina.

From the order of the Collembola, for example,

Onychiurus armatus.

From the order of the Orthoptera, for example,

Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus

, Gryllotalpa spp.,

Locusta migratoria migratorioides, Melanoplus differentialis

and

Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example,

Phylloxera vastatrix

, Pemphigus spp.,

Pediculus humanus corporis

Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

From the order of the Thysanoptera, for example,

Hercinothrips femoralis

and

Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,

Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus

and Triatoma spp.

From the order of the Homoptera, for example,

Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma langerum, 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., and Psylla spp.

From the order of the Lepidoptera, for example,

Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea

, Lymantria spp.,

Bucculatris thruberiella, 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, Cacoceia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima

and

Tortrix viridana.

From the order of the Coleoptera, for example,

Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae

, Diabrotica spp.,

Psylloides chrysocephala, Epilachna varivestis

, Atomaria spp.,

Oryzaephilus surinamensis

, Anthonomus spp., Sitophilus spp.,

Otiorrhynchus sulcatus, 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

and

Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp.,

Monomorium pharaonis

and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp.,

Drosophila melanogaster

, Musca spp., Fannia spp.,

Calliphora erythrocephala

, Lucilla 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, Ceratitis capitata, Dacus oleae

and

Tipula paludosa.

From the order of the Siphonaptera, for example,

Xenopsylla cheopis

and Ceratophyllus spp.

From the order of the Arachnida, for example,

Scorpio maurus

and

Latrodectus mactans.

From the class of the Helminthes, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis as well as Fasciola and phytopathogenic nematodes, for example those from the genera Meloidogyne, Heterodera, Ditylenchus, Aphelenchoides, Radopholus, Globodera, Pratylenchus, Longidorus and Xiphinema.

From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., and Oncomelania spp.

From the class of the Bivalva, for example, Dreissena spp.

The invention also relates to insecticidal and acaricidal agents which contain the compounds of the formula I, besides suitable formulation auxiliaries.

The agents according to the invention generally contain the active substances of the formula I to the extent of 1 to 95% by weight.

They can be formulated in various ways, depending on the prevailing biological and/or chemico-physical parameters. The following are therefore possible for formulation: wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SC), emulsions, sprayable solutions, dispersions on an oil or water basis (SC), suspoemulsions (SC), dusts (DP), seed-dressing agents, granules in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, “Spray Drying Handbook”, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries which are required, such as inert materials, surfactants, solvents and other additives are equally known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley & Sons, N.Y.; Marschen, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-active Ethylene Oxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to produce combinations with other pesticidally active substances, fertilizers and/or growth regulators, for example in the form of a readymix or a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which contain, besides the active substance and in addition to a diluent or inert material, wetting agents, for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleylmethyltaurate.

Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers. Examples of emulsifiers which can be used are: calcium salts of alkylarylsulfonates, 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 polyoxethylene sorbitol esters.

Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophyllite or diatomaceous earth. Granules can be prepared either by atomizing the active substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of carrier materials such as sand or faolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or sodium polyacrylate, or alternatively mineral oils. Suitable active substances can also be granulated in the fashion conventional for the preparation of fertilizer granules, if desired as a mixture with fertilizers.

The active substance concentration in wettable powders is, for example, approximately 10 to 90% by weight, the remainder to 100% is composed of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 5 to 80% by weight. Formulations in the form of dusts usually contain 5 to 20% of active substance, sprayable solutions approximately 2 to 20% by weight. In the case of granules, the active substance content depends partly on whether the active compound is liquid or solid and on which granulation auxiliaries, fillers, etc. are used.

In addition, the active substance formulations mentioned contain, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are conventional in each case.

For use, the concentrates which exist in commercially available form are, if appropriate, diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and also in the case of some microgranules. Preparations in the form of a dust and granulated preparations as well as sprayable solutions are customarily not further diluted with other inert substances before use.

The application rate required depends on the external conditions such as, inter alia, temperature and humidity. It can vary within wide limits, for example between 0.001 and 10.0 kg/ha or more of active ingredient, but it is preferably between 0.005 and 5 kg/ha.

The active substances according to the invention may be present in their commercially available formulations and in the application forms prepared from these formulations in the form of mixtures with other active substances such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.

The pesticides include, for example, phosphoric esters, carbamates, carboxylic esters, formamidines, tin compounds and substances produced by microorganisms. Preferred components for mixtures are

1. from the group comprising the phosphorus compounds acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyriphos-methyl, demeton, demeton-S-methyl, demeton-S-methyl-sulphone, dialifos, diazinon, dichlorvos, dicrotophos,

O,O-1,2,2,2-tetrachloroethyl phosphorothioate (SD 208 304), dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, fonofos, formothion, heptenophos, isazophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim, pirimiphos-ethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tetraclorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

2. from the group comprising the carbamates aldicarb, 2-secbutylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, ethyl 4,6,9-triaza-4-benzyl-6,10-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate (OK 135), 1-methylthio-(ethylidenamino)-N-methyl-N-(morpholinothio)carbamate (UC 51717);

3. from the group comprising the carboxylic esters allethrin, alphamethrin, 5-benzyl-3-furylmethyl-(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidene-methyl)cyclopropanecarboxylate, bioallethrin, bioallethrin ((S)cyclopentyl isomer), bioresmethrin, biphenate, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl-(1RS)-trans-3-(4-tert.butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyhalothrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), permethrin, pheothrin ((R) isomer), d-pralethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, tralomethrin;

4. from the group comprising the amidines amitraz, chlordimeform;

5. from the group comprising the tin compounds cyhexatin, fenbutatin oxide;

6. others abamectin,

Bacillus thuringiensis,

bensultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro12-0470), cyromazin, ethyl N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzcarboximidate, DDT, dicofol, N-(N(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-phenylamino)carbonyl)-2,6-difluorobenzamide (XRD 473), diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-yliden)-2,4-xylidine, dinobuton, dinocap, endosulfan, ethofenprox, (4-ethoxyphenyl)(dimethyl)(3-(3-phenoxyphenyl)propyl)silane, (4-ethoxyphenyl)(3-(4-fluoro-3-phenoxyphenyl)propyl)dimethylsilane, fenoxycarb, 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800) granulosis and nuclear polyhedrosis viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramechylnon (AC 217300), ivermectin, 2-nitromethyl-4,5-dihydro-6H-thiazine (SD 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam and triflumuron.

The active substance content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight.

Application is effected in a conventional fashion, matched to the use forms.

The active substances according to the invention are also suitable for controlling endo- and ectoparasites in the field of veterinary medicine or in the field of animal husbandry.

The active substances according to the invention are applied in a known fashion, such as by oral administration in the form of, for example, tablets, capsules, potions or granules, by dermal administration in the form of, for example, dipping, spraying, pouring-on and spotting-on and powdering, and also by parenteral administration in the form of, for example, an injection.

The novel compounds of the formula I according to the invention can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese etc.). In a preferred embodiment of the invention, the novel compounds, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed, are administered orally to the animals. Since they are excreted effectively in the feces, the development of insects in the feces of the animals can be prevented very simply in this fashion. The dosages and formulations suitable in each case are particularly dependent on the type and stage of development of the livestock and also on the infestation pressure, and can easily be determined and laid down by conventional methods. In the case of cattle, the novel compounds can be employed, for example, at dosage rates of 0.01 to 1 mg/kg of body weight.

The compounds of the formula I according to the invention are also distinguished by an outstanding fungicidal activity. Fungal pathogens which have already entered the plant tissue can be controlled successfully in a curative manner. This is particularly important and advantageous in the case of those fungal diseases which can no longer be controlled effectively with the otherwise customary fungicides once infection has taken place. The spectrum of action of the claimed compounds embraces a large number of various economically important phyto-pathogenic fungi such as, for example,

Pyricularia oryzae, Leptosphaeria nodorum, Drechslera teres,

powdery mildew species,

Venturia inaequalis, Botrytis cinerea, Pseudocercosporella herpotrichoides,

rusts as well as representatives of the Oomycetes such as, for example,

Phytophthora infestans

and

Plasmopara viticola.

Besides, the compounds according to the invention are also suitable for use in industrial fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking, or as preservatives in drilling and cutting oils.

The invention also relates to agents which comprise the compounds of the formula I besides suitable formulation auxiliaries. The agents according to the invention generally comprise 1 to 95% by weight of the active substances of the formula I.

They can be formulated in various ways, depending on the prevailing biological and/or chemico-physical parameters. The following possibilities are therefore suitable for formulation: wettable powders (WP), emulsifiable concentrates (EC), aqueous dispersions on oil or water basis (SC), suspoemulsions (SC), dusts (DP), seed-dressing agents, granules in the form of water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, “Spray Drying Handbook”, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries which are required, such as inert materials, surfactants, solvents and other additives are equally known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley & Sons, N.Y.; Marschen, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-active Ethylene Oxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986.

The active substances according to the invention can be employed, in their commercially available formulations, either on their own or in the form of a combination with other fungicides known from the literature.

Fungicides which are known from the literature and which can be combined according to the invention with the compounds of the formula (I) are, for example, the following products:

anilazine, benalaxyl, benodanil, benomyl, binapacryl, bitertanol, buthiobat, captafol, captan, carbendazim, carboxin, CGD-94240 F, chlobenzthiazone, chlorthalonil, cymoxanil, cyproconazole, cyprofuram, dichlofluanid, dichlomezin, dichlobutrazol, diethofencarb, difluconazole, dimethirimol, dimethomorph, diniconazole, dinocap, dithianon, dodemorph, dodine, edifenfos, ethirimol, etridazole, fenarimol, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fluaziram, fluobenzimine, fluorimide, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, fuberidazole, furalaxyl, furmecyclox, guazatine, hexa-conazole, imazalil, iprobenfos, iprodione, isoprothiolane, copper compounds such as copper oxychloride, copper oxine, copper oxide, mancozeb, maneb, mepronil, metalaxyl, methasulfocarb, methfuroxam, myclobutanil, nabam, nitrothalidopropyl, nuarimol, ofurace, oxadixyl, oxycarboxin, penconazole, pencycuron, PP 696, probenazole, probinel, prochloraz, procymidon, propamocarb, propiconazole, prothiocarb, pyracarbolid, pyrifenox, pyroquilon, rabenzazole, sulfur, tebuconazole, thiabendazole, thiofanate-methyl, thiram, tolclofos-methyl, tolyl-fluanid, triadimefon, triadimenol, tricyclazole, tridemorph, triflumizol, triforine, vinchlozolin, zineb, sodium dodecylsulfonate, sodium dodecylsulfate, sodium C13/C15-alcohol ether sulfonate, sodium cetostearyl-phosphate, dioctyl sodium sulfosuccinate, sodium iso-propylnaphthalenesulfonate, sodium methylenebis-naphthalenesulfonate, cetyltrimethylammonium chloride, salts of long-chain primary, secondary or tertiary amines, alkylpropylenamines, laurylpyrimidinium bromide, ethoxylated quaternized fatty amines, alkyldimethylbenzylammonium chloride and 1-hydroxyethyl-2-alkylimidazoline.

The abovementioned components for the combinations represent known active substances, most of which are described in GH. R Worthing, U. S. B. Walker, The Pesticide Manual, 7th Edition (1983), British Crop Protection Council.

The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges, the active substance concentration of the use forms can be between 0.0001 and 95% by weight of active substance, preferably between 0.001 and 1% by weight. They are used in a fashion matched to the use forms.

The following examples serve to illustrate the invention.

A. FORMULATION EXAMPLES

a) A dust is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc as inert material and comminuting the mixture in a hammer mill.

b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active substance, 65 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting and dispersing agent, and grinding the mixture in a pin-disk mill.

c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active substance with 7 parts by weight of a sulfo-succinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture in a ball mill to a fineness of below 5 microns.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of active substance, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol (10 EO) as emulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of active substance and an inert granulate carrier material such as attapulgite, granulated pumice and/or quartz sand. It is expedient to use a suspension of the wettable powder of Example b) with a solids content of 30%, which is sprayed onto the surface of attapulgite granules, and these are dried and mixed intimately. The amount of the wettable powder is approx. 5% by weight and that of the inert carrier material approx. 95% by weight of the finished granules.

B. BIOLOGICAL EXAMPLES (USE AS FUNGICIDE)

Example 1

Barley plants in the 3-leaf stage are heavily inoculated with conidia of powdery mildew of barley (

Erysiphe graminis

f. sp.

hordei

) and placed in a greenhouse at 20° C. and a relative atmospheric humidity of 90-95%. 24 hours after the inoculation, the plants are wetted uniformly with the compounds listed in Table 1 at the active substance concentrations which are indicated. After an incubation time of 10 days, the plants are examined for incidence of powdery mildew of barley. The disease indicence is expressed in % of diseased leaf area, relative to untreated, 100% infected control plants.

Applied at 500 mg of active substance/l of spray mixture, the following substances are found to suppress disease completely:

Compounds according to Example No. 9, 17, 25, 30, 55, 80, 93, 99, 100.

Example 2

Barley plants cv. “Igri” in the 2-leaf stage are treated to runoff point with an aqueous suspension of the claimed compounds.

After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of

Pyreno-phora teres

and incubated for 16 hours in a controlled-environment cabinet at a relative atmospheric humidity of 100%. The infected plants are subsequently grown on in the greenhouse at 25° C. and a relative atmospheric humidity of 80%.

Approx. 1 week after the inoculation, the disease is evaluated and the disease incidence is scored as diseased leaf area compared with the untreated, 100% infected control.

Applied at 500 mg of active substance/l of spray mixture, the following substances are found to suppress disease completely:

Compounds according to Example No. 2, 9, 10, 13, 14, 17, 25, 55, 80, 93, 106.

Example 3

Wheat cv. “Jubilar” in the 2-leaf stage is treated to runoff point with aqueous suspensions of the claimed compounds.

After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of

Puccinia recondita.

The dripping-wet plants are placed for approx. 16 hours in a controlled-environment cabinet at 20° C. and a relative atmospheric humidity of approx. 100%. They are then grown on in a greenhouse at a temperature of 22-25° C. and a relative atmospheric humidity of 50-70%.

After an incubation time of approx. 2 weeks, the fungus sporulates on the entire leaf area of the untreated control plants (100% infection), so that the test plants can be evaluated for disease. The disease incidence is expressed as diseased leaf area compared with the untreated, infected control plants.

Applied at 500 mg of active substance/l of spray mixture, the following substances are found to suppress disease completely:

Compounds according to Example No. 2, 9, 12, 17, 25, 30, 80, 93, 99.

BIOLOGICAL EXAMPLES (USE AS ACARICIDE/INSECTICIDE)

Example 1

Field beans (

Vicia faba

) heavily populated with the black bean aphid (

Aphis fabae

) are sprayed with aqueous dilutions of wettable powder concentrates with an active substance content of 250 ppm until the stage of beginning of runoff point is reached. The mortality of the aphids is determined after 3 days. A destruction of 100% can be achieved using the compounds according to Example No. 2, 9, 13, 17, 19, 25, 30, 55, 80, 93, 99, 106, 1741, 1749, 1750.

Example 2

Bean plants Phaseolus v.) are heavily populated with greenhouse spider mites (

Tetranychus urticae,

full population) were sprayed with the aqueous dilution of a wettable powder concentrate containing 250 ppm of the active substance in question.

The mortality of the mites was checked after 7 days. A destruction of 100% was achieved using the following compounds:

Compounds according to Example No. 2, 9, 10, 17, 19, 25, 30, 55, 80, 93, 94, 99, 106, 1741.

Example 3

Filter papers on which eggs of the large milkweed bug (

Oncopeltus fasciatus

) have been placed are treated with 0.5 ml portions of aqueous dilution of the test formulation. After the coating has dried on, the Petri dish is sealed, and the interior is kept at maximum atmospheric humidity. The dishes are kept at room temperature, and the oricidal and larvicidal activities are determined after 7 days. At an active substance content of 250 ppm, a mortality of 100% was obtained with the following compounds:

Compounds according to Example No. 2, 9, 10, 13, 17, 19, 25, 30, 55, 80, 93, 95, 99, 106, 312, 1741, 1749, 1750.

Example 4

1 ml portions of the test formulation, emulsified in water, are applied uniformly to the inside of the lid and the bottom of a Petri dish and, when the coating has dried on, batches of 10 imagines of the common housefly (

Musca domestica

) are introduced. The dishes are sealed and then kept at room temperature, the mortality of the test animals is determined after 3 hours. At 250 ppm (based on active substance content), the following preparations show a good activity (100% mortality) against the common housefly:

Compounds according to Example No. 9, 10, 17, 18, 19, 25, 55, 80, 93, 99, 106, 1741, 1750.

Example 5

Rice seed is placed into glass culture dishes containing cotton wool and germinated under moist conditions and, after the stem has grown to a length of approx. 8 cm, it is dipped together with the leaves into the test solution. The test solution is allowed to run off from the treated rice plants, and the plants are transferred to culture containers and populated with batches of 10 larvae (L3) of the species

Nilaparvata lugens,

the individual test concentrations being kept separate from each other. After the sealed culture containers have been kept at 21° C., the mortality of the cicada larvae can be determined after 4 days.

Under these test conditions, the compounds according to Example No. 9, 25, 30, 93, 99, 432 have a 100% activity at a test concentration of 250 ppm of the active ingredient.

Example 6

Wheat seed is pregerminated for 6 hours under water and then transferred to 10 ml glass test tubes and covered with in each case 2 ml of soil. 1 ml of water is added, and the plants remain in the glass culture dishes at room temperature (21° C.) until they have grown to a height of approx. 3 cm. Diabrotica larvae of a medium stage (batches of 10 specimens) are then transferred to the dishes and placed on the soil and, after 2 hours, 1 ml of the test liquid concentration to be tested is then pipetted onto the soil surface in the dishes.

After a standing time of 5 days under laboratory conditions (21° C.), the soil, or parts of the roots, are examined for live Diabrotica larvae, and the mortality is determined.

Under the test conditions mentioned, the compounds according to Example No. 2, 17, 19, 25, 93, 99 displayed an effectiveness of up to 100% at a test concentration of 250 ppm of the active ingredient.

Example 7

In vitro test with tropical cattle ticks (

Boophilus microplus

)

The following experimental set-up allowed the activity of the claimed compounds against ticks to be demonstrated:

To prepare a suitable preparation of active substance, the active substances were dissolved at a concentration of 10% (w/v) in a mixture composed of dimethylformamide (85 g), nonylphenol polyglycol ether (3 g) and oxethylated castor oil (7 g), and the resulting emulsion concentrates were diluted with water to a test concentration of 500 ppm.

Batches of ten females of the tropical tick

Boophilus microplus

which had sucked themselves full were immersed for five minutes in these active substance dilutions. The ticks were subsequently dried on filter paper and then attached, by their backs, to an adhesive film for the purpose of oviposition. The ticks were kept in an incubator at 28° C. and an atmospheric humidity of 90%.

As a control, female ticks were merely immersed in water. The inhibition of oviposition two weeks after the treatment was used to assess the effectiveness. 100% mean that no ticks have deposited eggs, 0% means that all ticks have deposited eggs.

In this test, a 100% inhibition of oviposition was caused by each of the compounds 10, 19, 30 and 106 at an active substance concentration of 500 ppm.

PREPARATION EXAMPLES

Example A

4-(4-tert-Butylcyclohexylamino)-5-chloro-6-ethylpyrimidine

3.5 g (0.02 mol) of 4,5-dichloro-6-ethylpyrimidine and 7.8 g (0.05 mol) of 4-tert-butylcyclohexylamine were heated for two hours at 100° C., without solvent. After the mixture had cooled to room temperature, it was worked up using methylene chloride/water and the organic phase was dried and concentrated. The product was chromatographed on silica gel using petroleum ether/ethyl acetate 7:3 for further purification and for the separation of the cis/trans isomers.

The trans-cyclohexylamino derivative is eluted first (0.8 g of yellow oil solidifies, m.p. 94-96°). After a mixed fraction, which was discarded, pure cis-cyclohexylamino derivative was finally obtained (3.0 g of yellow oil).

Preparation of 4-tert-butylcyclohexylamine 312 g of 4-tert-butylcyclohexanone in 500 ml of ammonia-saturated methanol were hydrogenated at 100° C. and 100 bar in the presence of 10 g of Raney nickel. The catalyst was filtered off, the mixture was concentrated, and the crude product was purified on a thin-layer evaporator (105°/0.5 mm). 303 g of colorless liquid were obtained. The product is an isomer mixture in which the cis-cyclohexylamine derivative prevails.

4-(cis-4-Phenyl-cyclohexyloxy)-5,6,7,8-tetrahydroquinazoline

0.5 g (16.7 mmol) of 80% NaH was added in portions to a solution of 1.85 g (105 mmol) of cis-4-phenylcyclohexanol in 30 ml of absolute THF. After this, the mixture was heated for 1 hour at 50° C., and 1.5 g (8.75 mmol) of 4-chloro-5,6,7,8-tetrahydroquinazoline, dissolved in 15 ml of absolute THF, were added dropwise. The reaction mixture was subsequently refluxed for 2 hours. After the mixture has cooled to room temperature, it was poured into saturated NH

4

Cl solution and this was extracted with ether, and the combined organic phase was dried over MgSO

4

. The solvent was evaporated in vacuo, and the residue (2.7 g) was purified by flash chromatography over silica gel, using n-hexane/ethyl acetate (2:1). Concentration gave 1.5 g (50.2% of theory), colorless crystals, m.p. 109° C.

4-(N-Benzoyl-piperidyl-4-oxy)-5-methoxy-6-methoxymethyl-pyrimidine

2.9 g (14.3 mmol) of N-benzoyl-4-hydroxypiperidine (prepared by NaBH

4

-reduction of N-benzoylpiperidine-4-one) were added to a suspension of 0.66 g (22 mmol) of 80% NaH in THF. This was then heated for 1 hour at 35-40° C., and 2.50 g (13.3 mmol) of 4-chloro-5-methoxy-6-methoxymethyl- pyrimidine were subsequently added without dilution. The reaction mixture was heated for 5 hours at 40° C., poured into a little saturated NH

4

Cl solution and extracted 5 times using ethyl acetate. The combined organic phases were dried over MgSO

4

, and the residue (3.4 g) was purified by flash chromatography over silica gel using ethyl acetate. Concentration gave 0.6 g (13% of theory) of yellow oil, n

D

20

=1.5815.

More examples can be found in Tables I-IV below.

Abbreviations used

T

1

T

2

T

3

T

4

T

5

T

6

T

7

T

8

T

9

T

10

T

11

T

12

T

13

T

14

T

15

T

16

T

17

T

18

T

19

T

20

T

21

T

22

T

23

T

24

T

25

T

26

T

27

T

28

T

29

T

30

T

31

T

32

T

33

T

34

T

35

T

36

T

37

T

38

T

39

T

40

T

41

T

42

T

43

T

44

T

45

T

46

T

47

T

48

T

49

T

50

T

51

T

52

T

53

T

54

T

55

T

56

T

57

T

58

T

59

T

60

T

61

T

62

T

63

T

64

T

65

T

66

T

67

T

68

T

69

T

70

T

71

T

72

T

73

T

74

T

75

T

76

T

77

T

78

T

79

T

80

T

81

T

82

T

83

T

84

T

85

T

86

T

87

T

88

T

89

T

90

T

91

T

92

T

93

T

94

T

95

T

96

T

97

T

98

T

99

T

100

T

101

T

102

T

103

T

104

T

105

T

106

T

107

T

108

T

109

T

110

T

111

T

112

T

113

T

114

T

115

T

116

T

117

T

118

T

119

T

120

T

121

T

122

T

123

T

124

T

125

T

126

T

127

T

128

T

129

T

130

T

131

T

132

T

133

T

134

T

135

T

136

T

137

T

138

T

139

T

140

T

141

T

142

T

143

T

144

T

145

T

146

T

147

T

148

T

149

T

150

T

151

T

152

T

153

T

154

T

155

T

156

T

157

T

158

T

159

T

160

T

161

T

162

T

163

T

164

T

165

T

166

T

167

T

168

T

169

T

170

T

171

T

172

T

173

T

174

T

175

T

176

T

177

T

178

T

179

T

180

T

181

T

182

T

183

T

184

T

185

T

186

T

187

T

188

T

189

T

190

T

191

T

192

T

193

T

194

T

195

T

196

T

197

T

198

T

199

T

200

T

201

T

202

T

203

T

204

T

205

T

206

T

207

T

208

T

209

T

210

T

211

T

212

T

213

T

214

T

215

T

216

T

217

T

218

T

219

T

220

T

221

T

222

T

223

T

224

T

225

T

226

T

227

T

228

T

229

T

230

T

231

T

232

T

233

T

234

T

235

T

236

T

237

T

238

T

239

T

240

T

241

T

242

T

243

T

244

T

245

T

246

T

247

T

248

TABLE I

Example

No.

R

1

R

2

R

3

X

E

Q

M.p. [° C.]

1

H

CH

2

OCH

3

OCH

3

NH

—

T

1

76-78

2

H

CH

2

OCH

3

OCH

3

NH

—

T

2

oil

3

H

CH

2

OCH

3

OCH

3

NH

—

T

3

oil

4

H

CH

2

OCH

3

OCH

3

NH

—

T

4

oil

5

H

CH

2

OCH

3

OCH

3

O

—

T

4

6

H

—(CH

2

)

4

—

O

—

T

4

7

H

C

2

H

5

Cl

NH

—

T

4

oil

8

H

C

2

H

5

Cl

O

—

T

4

9

H

CH

2

OCH

3

OCH

3

NH

—

T

5

, cis/trans = 1:2

oil

10

H

—(CH

2

)

4

—

NH

T

5

, cis/trans = 2:1

oil

11

H

—(CH

2

)

4

—

O

—

T

6

104

12

H

CH

2

OCH

3

OCH

3

NH

—

T

6

76-77

13

H

CH

2

OCH

3

OCH

3

O

—

T

6

oil

14

H

C

2

H

5

Cl

NH

—

T

6

94-96

15

H

C

2

H

5

Cl

O

—

T

7

oil

16

H

C

2

H

5

Cl

NH

—

T

7

oil

17

H

CH

2

OCH

3

OCH

3

NH

—

T

7

oil

18

H

CH

2

OCH

3

OCH

3

O

—

T

7

oil

19

H

—(CH

2

)

4

—

O

—

T

7

oil

20

CH

3

C

2

H

5

Cl

NH

—

T

7

21

CH

3

C

2

H

5

Cl

O

—

T

7

22

H

CH

2

OCH

3

OCH

3

NH

CH

2

T

5

oil

23

H

CH

2

OCH

3

OCH

3

O

″

T

5

oil

24

H

—(CH

2

)

4

—

O

CH

2

T

5

oil

25

H

CH

2

OCH

3

OCH

3

NH

H

T

8

oil

26

H

CH

2

OCH

3

OCH

3

O

H

T

8

oil

27

H

C

2

H

5

Cl

NH

H

T

8

oil

28

H

C

2

H

5

Cl

O

H

T

8

oil

29

H

—(CH

2

)

4

—

O

H

T

8

oil

30

H

CH

2

OCH

3

OCH

3

NH

H

T

9

oil

31

H

CH

2

OCH

3

OCH

3

O

H

T

9

oil

32

H

C

2

H

5

Cl

NH

H

T

9

oil

33

H

C

2

H

5

Cl

O

H

T

9

34

H

—(CH

2

)

4

—

O

H

T

9

oil

35

H

CH

2

OCH

3

OCH

3

NH

H

T

10

oil

36

H

CH

2

OCH

3

OCH

3

O

H

T

10

37

H

C

2

H

5

Cl

NH

H

T

10

oil

38

H

C

2

H

5

Cl

O

H

T

10

39

H

—(CH

2

)

4

—

O

H

T

10

40

H

CH

2

OCH

3

OCH

3

NH

H

T

11

oil

41

H

CH

2

OCH

3

OCH

3

O

H

T

11

42

H

—(CH

2

)

4

—

O

H

T

11

43

H

C

2

H

5

Cl

NH

—

T

11

oil

44

H

C

2

H

5

Cl

O

—

T

11

45

H

CH

2

OCH

3

OCH

3

NH

—

T

12

46

H

CH

2

OCH

3

OCH

3

O

—

T

12

47

H

C

2

H

5

Cl

NH

—

T

12

48

H

C

2

H

5

Cl

O

—

T

12

49

H

—(CH

2

)

4

—

O

—

T

12

50

H

CH

2

OCH

3

OCH

3

NH

—

T

13

51

H

CH

2

OCH

3

OCH

3

O

—

T

13

52

H

C

2

H

5

Cl

NH

—

T

13

53

H

C

2

H

5

Cl

O

—

T

13

54

H

—(CH

2

)

4

O

—

T

13

oil

55

H

CH

2

OCH

3

OCH

3

NH

—

T

14

oil

56

H

CH

2

OCH

3

OCH

3

O

—

T

14

57

H

C

2

H

5

Cl

NH

—

T

14

80-81

58

H

C

2

H

5

Cl

O

—

T

14

59

H

—(CH

2

)

4

—

O

—

T

14

69

60

H

CH

2

OCH

3

OCH

3

NH

—

T

15

78-80

61

CH

2

OCH

3

OCH

3

O

—

T

15

62

C

2

H

5

OCH

3

NH

—

T

15

63

C

2

H

5

OCH

3

O

—

T

15

64

—(CH

2

)

4

—

O

—

T

15

65

CH

2

OCH

3

OCH

3

NH

—

T

16

66

H

CH

2

OCH

3

OCH

3

O

—

T

16

67

H

C

2

H

5

Cl

NH

—

T

16

68

H

C

2

H

5

Cl

O

—

T

16

69

H

—(CH

2

)

4

—

O

—

T

16

70

H

CH

2

OCH

3

Cl

NH

—

T

17

71

H

CH

2

OCH

3

Cl

O

—

T

17

72

H

C

2

H

5

Cl

NH

—

T

17

73

H

C

2

H

5

Cl

O

—

T

17

74

H

—(CH

2

)

4

—

O

—

T

17

75

H

CH

2

OCH

3

OCH

3

NH

—

T

18

69-70

76

H

CH

2

OCH

3

OCH

3

O

—

T

18

77

H

C

2

H

5

Cl

NH

—

T

18

78

H

C

2

H

5

Cl

O

—

T

18

79

H

—(CH

2

)

4

—

O

—

T

18

80

H

CH

2

OCH

3

OCH

3

NH

—

T

19

oil

81

H

CH

2

OCH

3

OCH

3

O

—

T

19

oil

82

H

C

2

H

5

Cl

NH

—

T

19

oil

83

H

C

2

H

5

Cl

O

—

T

19

84

H

—(CH

2

)

4

—

O

—

T

19

oil

85

H

CH

2

OCH

3

OCH

3

NH

CH

2

T

5

oil

86

H

CH

2

OCH

3

OCH

3

O

″

T

5

oil

87

—(CH

2

)

4

—

O

″

T

5

oil

88

H

CH

2

OCH

3

OCH

3

NH

CHCH

3

T

20

oil

89

H

CH

2

OCH

3

OCH

3

O

″

T

20

90

H

C

2

H

5

Cl

NH

″

T

20

91

H

C

2

H

5

Cl

O

″

T

20

92

H

—(CH

2

)

4

—

O

—

T

20

oil

93

H

CH

2

OCH

3

OCH

3

NH

—

T

21

, cis/trans = 2:1

oil

94

H

CH

2

OCH

3

OCH

3

NH

—

T

22

70-72

95

H

CH

2

OCH

3

OCH

3

O

—

T

22

37

96

H

C

2

H

5

Cl

NH

—

T

22

79-80

97

H

—(CH

2

)

4

—

NH

—

T

22

165-166

98

H

—(CH

2

)

4

—

O

—

T

22

112

99

H

CH

2

OCH

3

OCH

3

NH

—

T

23

82-84

100

H

CH

2

OCH

3

OCH

3

O

—

T

23

109

101

H

C

2

H

5

Cl

NH

—

T

23

74-75

102

H

C

2

H

5

Cl

O

—

T

23

103

CH

3

C

2

H

5

Cl

NH

—

T

23

104

CH

3

C

2

H

5

Cl

O

—

T

23

105

H

—(CH

2

)

4

—

NH

—

T

23

121-123

106

H

—(CH

2

)

4

)—

O

—

T

23

109

107

H

C

2

H

5

C

2

H

5

O

—

T

23

108

H

CH

2

OCH

3

OCH

3

NH

—

T

24

oil

109

H

CH

2

OCH

3

OCH

3

O

—

T

24

110

H

C

2

H

5

Cl

NH

—

T

24

63-65

111

H

C

2

H

5

Cl

O

—

T

24

112

H

—(CH

2

)

4

—

O

—

T

24

93-94

113

H

CH

2

OCH

3

OCH

3

NH

—

T

25

114

H

CH

2

OCH

3

OCH

3

O

—

T

25

115

H

C

2

H

5

Cl

NH

—

T

25

116

H

C

2

H

5

Cl

NH

—

T

25

117

H

—(CH

2

)

4

—

O

—

T

25

118

H

CH

2

OCH

3

OCH

3

NH

—

T

26

119

H

CH

2

OCH

3

OCH

3

O

—

T

26

120

H

C

2

H

5

Cl

NH

—

T

26

121

H

C

2

H

5

Cl

O

—

T

26

122

H

—(CH

2

)

4

—

O

—

T

26

123

H

CH

2

OCH

3

OCH

3

NH

—

T

27

124

H

CH

2

OCH

3

OCH

3

O

—

T

27

125

H

C

2

H

5

Cl

NH

—

T

27

126

H

C

2

H

5

Cl

O

—

T

27

127

H

—(CH

2

)

4

—

O

—

T

27

128

H

CH

2

OCH

3

Cl

NH

—

T

28

129

H

CH

2

OCH

3

Cl

O

—

T

28

130

H

C

2

H

5

Cl

NH

—

T

28

131

H

C

2

H

5

Cl

O

—

T

28

132

H

—(CH

2

)

4

—

O

—

T

28

133

H

CH

2

OCH

3

OCH

3

NH

—

T

29

134

H

CH

2

OCH

3

OCH

3

O

—

T

29

135

H

C

2

H

5

Cl

NH

—

T

29

136

H

C

2

H

5

Cl

NH

—

T

29

137

H

—(CH

2

)

4

—

O

—

T

29

138

H

CH

2

OCH

3

OCH

3

NH

—

T

30

oil

139

H

C

2

H

5

Cl

NH

—

T

30

oil

140

H

CH

2

OCH

3

OCH

3

NH

—

T

31

141

H

CH

2

OCH

3

OCH

3

O

—

T

31

142

H

C

2

H

5

Cl

NH

—

T

31

143

H

C

2

H

5

Cl

O

—

T

31

144

H

—(CH

2

)

4

—

O

—

T

31

145

H

CH

2

OCH

3

OCH

3

NH

—

T

32

146

H

CH

2

OCH

3

OCH

3

O

—

T

32

147

H

C

2

H

5

Cl

NH

—

T

32

148

H

C

2

H

5

Cl

O

—

T

32

149

H

—(CH

2

)

4

—

O

—

T

32

150

H

CH

2

OCH

3

OCH

3

NH

T

33

151

H

CH

2

OCH

3

OCH

3

O

T

33

152

H

C

2

H

5

Cl

NH

T

33

153

H

C

2

H

5

Cl

O

T

33

154

H

—(CH

2

)

4

—

O

T

33

155

H

CH

2

OCH

3

OCH

3

NH

—

T

34

oil

156

H

CH

2

OCH

3

OCH

3

NH

—

T

35

oil

157

H

CH

2

OCH

3

OCH

3

O

—

T

35

158

H

C

2

H

5

Cl

NH

—

T

35

159

H

C

2

H

5

Cl

O

—

T

35

160

H

—(CH

2

)

4

—

O

—

T

35

161

H

CH

2

OCH

3

OCH

3

NH

—

T

36

162

H

CH

2

OCH

3

OCH

3

O

—

T

36

163

H

C

2

H

5

Cl

NH

—

T

36

164

H

C

2

H

5

Cl

O

—

T

36

165

H

—(CH

2

)

4

—

O

—

T

36

166

H

CH

2

OCH

3

OCH

3

NH

—

T

37

167

H

CH

2

OCH

3

OCH

3

O

—

T

37

168

H

C

2

H

5

Cl

NH

—

T

37

169

H

C

2

H

5

Cl

O

—

T

37

170

H

—(CH

2

)

4

—

O

—

T

37

171

H

CH

2

OCH

3

OCH

3

NH

—

T

38

172

H

CH

2

OCH

3

OCH

3

O

—

T

38

173

H

C

2

H

5

Cl

NH

—

T

38

174

H

C

2

H

5

Cl

O

—

T

38

175

H

—(CH

2

)

4

—

O

—

T

38

176

H

CH

2

OCH

3

OCH

3

NH

—

T

39

177

H

CH

2

OCH

3

OCH

3

O

—

T

39

178

H

C

2

H

5

Cl

NH

—

T

40

179

H

C

2

H

5

Cl

O

—

T

40

180

H

—(CH

2

)

4

—

O

—

T

40

181

H

CH

2

OCH

3

OCH

3

NH

—

T

41

182

H

CH

2

OCH

3

OCH

3

O

—

T

41

183

H

C

2

H

5

Cl

NH

—

T

41

184

H

C

2

H

5

Cl

O

—

T

41

185

H

—(CH

2

)

4

—

O

—

T

41

186

H

CH

2

OCH

3

OCH

3

NH

—

T

42

187

H

CH

2

OCH

3

OCH

3

O

—

T

42

188

H

C

2

H

5

Cl

NH

—

T

42

189

H

C

2

H

5

Cl

O

—

T

42

190

H

—(CH

2

)

4

—

O

—

T

43

191

H

CH

2

OCH

3

OCH

3

NH

—

T

43

192

H

CH

2

OCH

3

OCH

3

NH

—

T

44

oil

193

H

CH

2

OCH

3

OCH

3

O

—

T

44

194

H

C

2

H

5

Cl

NH

—

T

44

195

H

C

2

H

5

Cl

O

—

T

44

196

H

—(CH

2

)

4

—

O

—

T

44

197

H

CH

2

OCH

3

OCH

3

NH

—

T

45

198

H

CH

2

OCH

3

OCH

3

O

—

T

45

199

H

C

2

H

5

Cl

NH

—

T

45

200

H

C

2

H

5

Cl

O

—

T

45

201

H

—(CH

2

)

4

—

O

—

T

45

202

H

CH

2

OCH

3

OCH

3

NH

—

T

46

60-62

203

H

CH

2

OCH

3

OCH

3

NH

—

T

47

204

H

C

2

H

5

Cl

NH

—

T

47

205

H

CH

2

OCH

3

OCH

3

NH

—

T

48

206

H

C

2

H

5

Cl

NH

—

T

48

207

H

CH

2

OCH

3

OCH

3

NH

—

T

49

208

H

CH

2

OCH

3

OCH

3

NH

—

T

50

solid

209

H

CH

2

OCH

3

OCH

3

O

—

T

50

210

H

C

2

H

5

Cl

NH

—

T

50

211

H

C

2

H

5

Cl

O

—

T

50

212

H

—(CH

2

)

4

—

O

—

T

50

213

H

CH

2

OCH

3

Cl

NH

—

T

51

214

H

CH

2

OCH

3

Cl

O

—

T

51

215

H

C

2

H

5

Cl

NH

—

T

51

216

H

C

2

H

5

Cl

O

—

T

51

217

H

—(CH

2

)

4

—

O

—

T

51

218

CH

2

OCH

3

OCH

3

NH

—

T

52

219

CH

2

OCH

3

OCH

3

O

—

T

52

220

H

C

2

H

5

Cl

NH

—

T

52

221

H

C

2

H

5

Cl

O

—

T

52

222

H

—(CH

2

)

4

—

O

—

T

52

223

H

CH

2

OCH

3

OCH

3

NH

—

T

53

142-143

224

H

CH

2

OCH

3

OCH

3

O

—

T

53

oil

225

H

—(CH

2

)

4

—

O

—

T

53

226

H

CH

2

OCH

3

OCH

3

NH

—

T

54

83-85

227

H

CH

2

OCH

3

OCH

3

O

—

T

54

oil

228

H

—(CH

2

)

4

—

O

—

T

54

95-100

229

H

CH

2

OCH

3

OCH

3

NH

—

T

55

112-114

230

H

CH

2

OCH

3

OCH

3

NH

—

T

56

231

H

CH

2

OCH

3

OCH

3

NH

—

T

57

232

H

CH

2

OCH

3

OCH

3

O

—

T

57

233

H

C

2

H

5

Cl

NH

—

T

57

234

H

C

2

H

5

Cl

O

—

T

57

235

H

—(CH

2

)

4

—

O

—

T

57

236

H

CH

2

OCH

3

OCH

3

NH

—

T

58

137-139

237

H

CH

2

OCH

3

OCH

3

O

—

T

58

238

H

C

2

H

5

Cl

NH

—

T

58

239

H

C

2

H

5

Cl

O

—

T

58

240

H

—(CH

2

)

4

—

O

—

T

58

241

H

CH

2

OCH

3

OCH

3

NH

—

T

59

84-85

242

H

CH

2

OCH

3

OCH

3

O

—

T

59

243

H

C

2

H

5

Cl

NH

—

T

59

83-84

244

H

C

2

H

5

Cl

O

—

T

59

245

H

—(CH

2

)

4

—

NH

—

T

59

oil

246

H

CH

2

OCH

3

OCH

3

NH

—

T

60

247

H

CH

2

OCH

3

OCH

3

O

—

T

60

248

H

C

2

H

5

Cl

NH

—

T

60

249

H

C

2

H

5

Cl

O

—

T

60

250

H

—(CH

2

)

4

—

O

—

T

60

251

H

CH

2

OCH

3

OCH

3

NH

—

T

61

252

H

CH

2

OCH

3

OCH

3

O

—

T

61

253

H

C

2

H

5

Cl

NH

—

T

61

254

H

C

2

H

5

Cl

O

—

T

61

255

H

—(CH

2

)

4

—

O

—

T

61

256

H

CH

2

OCH

3

OCH

3

NH

—

T

62

95-96

257

H

CH

2

OCH

3

OCH

3

O

—

T

62

258

H

C

2

H

5

Cl

NH

—

T

62

101-102

259

H

C

2

H

5

Cl

O

—

T

62

260

H

—(CH

2

)

4

—

O

—

T

62

261

H

CH

2

OCH

3

OCH

3

NH

—

T

63

262

H

CH

2

OCH

3

OCH

3

O

—

T

63

263

H

C

2

H

5

Cl

NH

—

T

63

81-83

264

H

C

2

H

5

Cl

O

—

T

63

265

H

—(CH

2

)

4

—

O

—

T

63

266

H

CH

2

OCH

3

OCH

3

NH

—

T

64

267

H

CH

2

OCH

3

OCH

3

O

—

T

64

268

H

C

2

H

5

Cl

NH

—

T

64

269

H

C

2

H

5

Cl

O

—

T

64

270

H

—(CH

2

)

4

—

—

—

T

64

271

H

CH

2

OCH

3

OCH

3

NH

—

T

65

272

H

CH

2

OCH

3

OCH

3

O

—

T

65

273

H

C

2

H

5

Cl

NH

—

T

65

274

H

C

2

H

5

Cl

O

—

T

65

275

H

—(CH

2

)

4

—

O

—

T

65

276

H

CH

2

OCH

3

Cl

NH

—

T

4

277

H

C

2

C

5

Br

NH

—

T

4

278

H

C

2

C

5

C

2

C

5

NH

—

T

4

279

H

CH

2

OCH

3

Cl

NH

—

T

7

oil

280

H

CH

2

OCH

3

C

2

C

5

NH

—

T

7

oil

281

H

CH

2

OCH

3

H

NH

—

T

7

oil

282

H

C

2

H

5

C

2

H

5

NH

—

T

7

283

H

C

2

H

5

Br

NH

—

T

7

284

H

C

2

H

5

F

NH

—

T

7

285

H

CH

3

Cl

NH

—

T

7

286

H

CH

3

OCH

3

NH

—

T

7

287

H

C

2

H

5

OCH

3

NH

—

T

7

288

H

CH(CH

3

)

2

Cl

NH

—

T

7

289

H

cyclo-

Cl

NH

—

T

7

propyl

290

H

C

2

H

5

C

2

H

5

NH

—

T

8

291

H

C

2

H

5

Br

NH

—

T

8

292

H

CH

2

OCH

3

Cl

NH

—

T

8

293

H

C

2

H

5

C

2

H

5

NH

—

T

9

294

H

CH

2

OCH

3

Cl

NH

—

T

9

295

H

C

2

H

5

Br

NH

—

T

9

296

H

C

2

H

5

C

2

H

5

NH

—

T

10

297

H

C

2

H

5

Br

NH

—

T

10

298

H

CH

2

OCH

3

Cl

NH

—

T

10

299

H

C

2

H

5

C

2

H

5

NH

—

T

11

300

H

C

2

H

5

C

2

H

5

O

—

T

11

301

H

CH

2

OCH

3

Cl

NH

—

T

11

302

H

C

2

H

5

Br

NH

—

T

11

303

H

C

2

H

5

C

2

H

5

NH

—

T

14

304

H

C

2

H

5

C

2

H

5

O

—

T

14

305

H

CH

2

OCH

3

Cl

NH

—

T

14

306

H

CH

2

OCH

3

Cl

NH

—

T

23

oil

307

H

CH

2

OCH

3

C

2

H

5

NH

—

T

23

78-79

308

H

CH

2

OCH

3

H

NH

—

T

23

oil

309

H

C

2

H

5

C

2

H

5

NH

—

T

23

310

H

C

2

H

5

I

NH

—

T

23

311

H

C

2

H

5

F

NH

—

T

23

312

H

C

2

H

5

F

O

—

T

23

313

H

C

2

H

5

Br

NH

—

T

23

314

H

CH

3

Cl

NH

—

T

23

315

H

(CH

2

)

4

NH

—

T

24

164-166

316

H

CH

2

OCH

3

OCH

3

NH

—

T

66

317

H

CH

2

OCH

3

OCH

3

O

—

T

66

oil

318

H

C

2

H

5

Cl

NH

—

T

66

319

H

C

2

H

5

Cl

O

—

T

66

oil

320

H

(CH

2

)

4

NH

—

T

66

321

H

(CH

2

)

4

O

—

T

66

oil

322

H

C

2

C

5

C

2

H

5

NH

—

T

66

323

H

CH

2

OCH

3

Cl

NH

—

T

66

324

H

CH

2

OCH

3

OCH

3

NH

—

T

67

325

H

CH

2

OCH

3

OCH

3

O

—

T

67

326

H

C

2

H

5

Cl

NH

—

T

67

327

H

C

2

H

5

Cl

O

—

T

67

328

H

(CH

2

)

4

O

—

T

67

329

H

CH

2

OCH

3

OCH

3

NH

—

T

68

oil

330

H

CH

2

OCH

3

OCH

3

O

—

T

68

oil

331

H

C

2

H

5

Cl

NH

—

T

68

oil

332

H

C

2

H

5

Cl

O

—

T

68

oil

333

H

C

2

H

5

C

2

H

5

NH

—

T

68

334

H

C

2

H

5

C

2

H

5

O

—

T

68

335

H

(CH

2

)

4

NH

—

T

68

336

H

(CH

2

)

4

O

—

T

68

oil

337

H

C

2

C

5

Br

NH

—

T

68

338

H

C

2

H

5

Br

O

—

T

68

339

H

C

2

H

5

F

NH

—

T

68

340

H

C

2

H

5

F

O

—

T

68

341

H

CH

2

OCH

3

Cl

NH

—

T

68

342

H

CH

2

OCH

3

Cl

O

—

T

68

343

H

CH

3

Cl

NH

—

T

68

344

H

CH

2

OCH

3

OCH

3

NH

—

T

69

345

H

CH

2

OCH

3

OCH

3

O

—

T

69

346

H

C

2

H

5

Cl

NH

—

T

69

347

H

C

2

H

5

Cl

NH

—

T

69

348

H

(CH

2

)

4

NH

—

T

69

349

H

(CH

2

)

4

O

—

T

69

79-82

350

H

C

2

H

5

C

2

H

5

NH

—

T

69

351

H

C

2

H

5

C

2

H

5

O

—

T

69

352

H

C

2

H

5

Cl

NH

—

T

70

352

H

C

2

H

5

Cl

O

—

T

70

oil

354

H

CH

2

OCH

3

OCH

3

NH

—

T

70

355

H

CH

2

OCH

3

OCH

3

O

—

T

70

oil

356

H

(CH

2

)

4

O

—

T

70

oil

357

H

CH

2

OCH

3

OCH

3

NH

—

T

71

oil

358

H

CH

2

OCH

3

OCH

3

O

—

T

71

359

H

C

2

H

5

Cl

NH

—

T

71

oil

360

H

C

2

H

5

Cl

O

—

T

71

361

H

(CH

2

)

4

NH

—

T

71

362

H

(CH

2

)

4

O

—

T

71

363

H

C

2

H

5

C

2

H

5

NH

—

T

71

364

H

C

2

H

5

C

2

H

5

O

—

T

71

365

H

CH

2

OCH

3

OCH

3

NH

—

T

72

oil

366

H

CH

2

OCH

3

OCH

3

O

—

T

72

367

H

C

2

H

5

Cl

NH

—

T

72

368

H

C

2

H

5

Cl

O

—

T

72

369

H

(CH

2

)

4

NH

—

T

72

370

H

(CH

2

)

4

O

—

T

72

371

H

C

2

H

5

C

2

H

5

NH

—

T

72

372

H

C

2

H

5

C

2

H

5

O

—

T

72

373

H

CH

2

OCH

3

OCH

3

NH

—

T

73

374

H

CH

2

OCH

3

OCH

3

O

—

T

73

375

H

C

2

H

5

Cl

NH

—

T

73

376

H

C

2

H

5

Cl

O

—

T

73

377

H

(CH

2

)

4

O

T

73

378

H

CH

2

OCH

3

OCH

3

NH

—

T

74

379

H

CH

2

OCH

3

OCH

3

O

—

T

74

oil

380

H

C

2

H

5

Cl

NH

—

T

74

381

H

C

2

H

5

Cl

O

—

T

74

87

382

H

(CH

2

)

4

O

—

T

74

86

383

H

C

2

H

5

Cl

NH

—

T

75

384

H

CH

2

OCH

3

OCH

3

NH

—

T

76

oil

385

H

CH

2

OCH

3

OCH

3

O

—

T

76

oil

386

H

C

2

H

5

Cl

NH

—

T

76

oil

387

H

C

2

H

5

Cl

O

—

T

76

58

388

H

(CH

2

)

4

NH

—

T

76

389

H

(CH

2

)

4

O

—

T

76

99-100

390

H

CH

2

OCH

3

C

2

H

5

NH

—

T

76

oil

391

H

C

2

H

5

C

2

H

5

NH

—

T

76

392

H

C

2

H

5

C

2

H

5

O

—

T

76

393

H

CH

2

OCH

3

Cl

NH

—

T

76

394

H

C

2

H

5

F

NH

—

T

76

395

H

C

2

H

5

Br

NH

—

T

76

396

H

CH

3

Cl

NH

—

T

76

397

H

C

2

H

5

Cl

NH

—

T

76

73-75

398

H

(CH

2

)

4

O

—

T

77

83

399

H

CH

2

OCH

3

C

2

H

5

NH

—

T

77

90-92

400

H

CH

2

OCH

3

OCH

3

NH

—

T

78

401

H

CH

2

OCH

3

OCH

3

O

—

T

78

402

H

C

2

H

5

Cl

NH

—

T

78

oil

403

H

C

2

H

5

Cl

O

—

T

78

oil

404

H

(CH

2

)

4

O

—

T

78

oil

405

H

CH

2

OCH

3

OCH

3

NH

—

T

79

406

H

C

2

H

5

Cl

NH

—

T

79

78-79

407

H

CH

2

OCH

3

OCH

3

NH

—

T

80

408

H

CH

2

OCH

3

OCH

3

O

—

T

80

oil

409

H

C

2

H

5

Cl

NH

—

T

80

oil

410

H

C

2

H

5

Cl

O

—

T

80

oil

411

H

(CH

2

)

4

O

—

T

80

oil

412

H

C

2

H

5

Cl

NH

—

T

81

72-74

413

H

C

2

H

5

Cl

O

—

T

81

oil

414

H

CH

2

OCH

3

OCH

3

NH

—

T

82

415

H

CH

2

OCH

3

OCH

3

O

—

T

82

oil

416

H

C

2

H

5

Cl

NH

—

T

82

417

H

C

2

H

5

Cl

O

—

T

82

65

418

H

(CH

2

)

4

O

—

T

82

68

419

H

CH

2

OCH

3

OCH

3

NH

—

T

84

420

H

CH

2

OCH

3

OCH

3

O

—

T

84

421

H

C

2

H

5

Cl

NH

—

T

84

422

H

C

2

H

5

Cl

O

—

T

84

423

H

(CH

2

)

4

O

—

T

84

424

H

CH

2

OCH

3

OCH

3

NH

T

85

425

H

CH

2

OCH

3

OCH

3

O

T

85

426

H

C

2

H

5

Cl

NH

T

85

427

H

C

2

H

5

Cl

O

T

85

428

H

(CH

2

)

4

O

T

85

429

H

CH

2

OCH

3

OCH

3

NH

—

T

86

430

H

CH

2

OCH

3

OCH

3

O

—

T

86

431

H

C

2

H

5

Cl

NH

—

T

86

432

H

C

2

H

5

Cl

O

—

T

86

433

H

(CH

2

)

4

O

—

T

86

434

H

CH

2

OCH

3

OCH

3

NH

—

T

87

435

H

CH

2

OCH

3

OCH

3

O

—

T

87

oil

436

H

C

2

H

5

Cl

NH

—

T

87

oil

437

H

C

2

H

5

Cl

O

—

T

87

57

438

H

(CH

2

)

4

O

—

T

87

67

439

H

C

2

H

5

Cl

NH

—

T

88

65-66

440

H

CH

2

OCH

3

OCH

3

NH

—

T

89

oil

441

H

CH

2

OCH

3

OCH

3

O

—

T

89

oil

442

H

C

2

H

5

Cl

NH

—

T

89

oil

443

H

C

2

H

5

Cl

O

—

T

89

53

444

H

(CH

2

)

4

O

—

T

89

59

445

H

CH

2

OCH

3

OCH

3

NH

—

T

90

oil

446

H

C

2

H

5

OCH

3

NH

—

T

90

63-65

447

H

CH

2

OCH

3

OCH

3

NH

—

T

91

448

H

CH

2

OCH

3

OCH

3

O

—

T

91

449

H

C

2

H

5

Cl

NH

—

T

91

450

H

C

2

H

5

Cl

O

—

T

91

451

H

(CH

2

)

4

O

—

T

91

452

H

CH

2

OCH

3

OCH

3

NH

—

T

92

453

H

CH

2

OCH

3

OCH

3

O

—

T

92

454

H

C

2

H

5

Cl

NH

—

T

92

455

H

C

2

H

5

Cl

O

—

T

92

456

H

(CH

2

)

4

NH

—

T

92

457

H

CH

2

OCH

3

OCH

3

O

—

T

93

458

H

CH

2

OCH

3

OCH

3

NH

—

T

93

459

H

C

2

H

5

Cl

O

—

T

93

460

H

C

2

H

5

Cl

O

—

T

93

461

H

(CH

2

)

4

NH

—

T

93

462

H

(CH

2

)

4

O

—

T

93

463

H

CH

2

OCH

3

OCH

3

NH

—

T

94

464

H

CH

2

OCH

3

OCH

3

O

—

T

94

465

H

C

2

H

5

Cl

NH

—

T

94

oil

466

H

C

2

H

5

Cl

O

—

T

94

58-60

467

H

(CH

2

)

4

O

—

T

94

oil

468

H

CH

2

OCH

3

OCH

3

NH

—

T

95

469

H

CH

2

OCH

3

OCH

3

O

—

T

95

470

H

C

2

H

5

Cl

NH

—

T

95

oil

471

H

C

2

H

5

Cl

O

—

T

95

oil

472

H

(CH

2

)

4

O

—

T

95

oil

473

H

C

2

H

5

Cl

NH

—

T

96

oil

474

H

CH

2

OCH

3

OCH

3

NH

—

T

97

475

H

CH

2

OCH

3

OCH

3

O

—

T

97

476

H

C

2

H

5

Cl

NH

—

T

97

477

H

C

2

H

5

Cl

O

—

T

97

71

478

H

(CH

2

)

4

NH

—

T

97

479

H

(CH

2

)

4

O

—

T

97

oil

480

H

CH

2

OCH

3

OCH

3

NH

—

T

98

481

H

CH

2

OCH

3

OCH

3

O

—

T

98

482

H

C

2

H

5

Cl

NH

—

T

98

483

H

C

2

H

5

Cl

O

—

T

98

484

H

(CH

2

)

4

O

—

T

98

oil

485

H

CH

2

OCH

3

OCH

3

NH

—

T

99

486

H

CH

2

OCH

3

OCH

3

O

—

T

99

487

H

C

2

H

5

Cl

NH

—

T

99

488

H

C

2

H

5

Cl

O

—

T

99

489

H

(CH

2

)

4

O

—

T

99

490

H

CH

2

OCH

3

OCH

3

NH

—

T

100

491

H

CH

2

OCH

3

OCH

3

O

—

T

100

492

H

C

2

H

5

Cl

NH

—

T

100

493

H

C

2

H

5

Cl

O

—

T

100

494

H

(CH

2

)

4

O

—

T

100

495

H

CH

2

OCH

3

OCH

3

NH

—

T

101

496

H

CH

2

OCH

3

OCH

3

O

—

T

101

497

H

C

2

H

5

Cl

NH

—

T

101

498

H

C

2

H

5

Cl

O

—

T

101

499

H

(CH

2

)

4

O

—

T

101

500

H

CH

2

OCH

3

OCH

3

NH

—

T

102

501

H

CH

2

OCH

3

OCH

3

O

—

T

102

502

H

C

2

H

5

Cl

NH

—

T

102

503

H

C

2

H

5

Cl

O

—

T

102

504

H

(CH

2

)

4

O

—

T

102

505

H

CH

2

OCH

3

OCH

3

NH

—

T

103

506

H

CH

2

OCH

3

OCH

3

O

—

T

103

507

H

C

2

H

5

Cl

NH

—

T

103

508

H

C

2

H

5

Cl

O

—

T

103

509

H

(CH

2

)

4

O

—

T

103

510

H

CH

2

OCH

3

OCH

3

NH

—

T

104

511

H

CH

2

OCH

3

OCH

3

O

—

T

104

oil

512

H

C

2

H

5

Cl

NH

—

T

104

513

H

C

2

H

5

Cl

O

—

T

104

100-103

514

H

(CH

2

)

4

O

—

T

104

108-112

515

H

CH

2

OCH

3

OCH

3

NH

—

T

105

516

H

CH

2

OCH

3

OCH

3

O

−

T

105

517

H

C

2

H

5

Cl

NH

—

T

105

518

H

C

2

H

5

Cl

O

—

T

105

519

H

(CH

2

)

4

O

—

T

105

520

H

CH

2

OCH

3

OCH

3

NH

—

T

106

521

H

CH

2

OCH

3

OCH

3

O

—

T

106

522

H

C

2

H

5

Cl

NH

—

T

106

523

H

C

2

H

5

Cl

O

—

T

106

524

H

(CH

2

)

4

O

—

T

106

525

H

CH

2

OCH

3

OCH

3

NH

—

T

107

526

H

CH

2

OCH

3

OCH

3

O

—

T

107

oil

527

H

C

2

H

5

Cl

NH

—

T

107

528

H

C

2

H

5

Cl

O

—

T

107

oil

529

H

(CH

2

)

4

O

—

T

107

oil

530

H

CH

2

OCH

3

OCH

3

NH

—

T

108

531

H

CH

2

OCH

3

OCH

3

O

—

T

108

532

H

C

2

H

5

Cl

NH

—

T

108

533

H

C

2

H

5

Cl

O

—

T

108

534

H

(CH

2

)

4

O

—

T

108

535

H

CH

2

OCH

3

OCH

3

NH

—

T

109

536

H

CH

2

OCH

3

OCH

3

O

—

T

109

537

H

C

2

H

5

Cl

NH

—

T

109

538

H

C

2

H

5

Cl

O

—

T

109

539

H

(CH

2

)

4

O

—

T

109

540

H

CH

2

OCH

3

OCH

3

NH

—

T

110

541

H

CH

2

OCH

3

OCH

3

O

—

T

110

542

H

C

2

H

5

Cl

NH

—

T

110

543

H

C

2

H

5

Cl

O

—

T

110

544

H

(CH

2

)

4

O

—

T

110

545

H

CH

2

OCH

3

OCH

3

NH

—

T

111

546

H

CH

2

OCH

3

OCH

3

O

—

T

111

547

H

C

2

H

5

Cl

NH

—

T

111

548

H

C

2

H

5

Cl

O

—

T

111

549

H

(CH

2

)

4

O

—

T

111

550

H

CH

2

OCH

3

OCH

3

NH

—

T

112

551

H

CH

2

OCH

3

OCH

3

O

—

T

112

552

H

C

2

H

5

Cl

NH

—

T

112

553

H

C

2

H

5

Cl

O

—

T

112

554

H

(CH

2

)

4

O

—

T

112

oil

555

H

CH

2

OCH

3

OCH

3

NH

—

T

113

556

H

CH

2

OCH

3

OCH

3

O

—

T

113

557

H

C

2

H

5

Cl

NH

—

T

113

558

H

C

2

H

5

Cl

O

—

T

113

559

H

(CH

2

)

4

O

—

T

113

560

H

CH

2

OCH

3

OCH

3

NH

—

T

114

561

H

CH

2

OCH

3

OCH

3

O

—

T

114

562

H

C

2

H

5

Cl

NH

—

T

114

563

H

C

2

H

5

Cl

O

—

T

114

oil

564

H

(CH

2

)

4

O

—

T

114

565

H

CH

2

OCH

3

OCH

3

NH

—

T

115

566

H

CH

2

OCH

3

OCH

3

O

—

T

115

oil

567

H

C

2

H

5

Cl

NH

—

T

115

oil

568

H

C

2

H

5

Cl

O

—

T

115

569

H

(CH

2

)

4

O

—

T

115

oil

570

H

C

2

H

5

Cl

NH

—

T

116

oil

571

H

CH

2

OCH

3

OCH

3

NH

—

T

117

572

H

CH

2

OCH

3

OCH

3

O

—

T

117

573

H

C

2

H

5

Cl

NH

—

T

117

574

H

C

2

H

5

Cl

O

—

T

117

575

H

(CH

2

)

4

O

—

T

117

576

H

CH

2

OCH

3

OCH

3

NH

—

T

118

577

H

CH

2

OCH

3

OCH

3

O

—

T

118

oll

578

H

C

2

H

5

Cl

NH

—

T

118

579

H

C

2

H

5

Cl

O

—

T

118

oil

580

H

(CH

2

)

4

O

—

T

118

oil

581

H

CH

2

OCH

3

OCH

3

NH

—

T

119

582

H

CH

2

OCH

3

OCH

3

O

—

T

119

583

H

C

2

H

5

Cl

NH

—

T

119

584

H

C

2

H

5

Cl

O

—

T

119

585

H

(CH

2

)

4

O

—

T

119

586

H

CH

2

OCH

3

OCH

3

NH

—

T

120

587

H

CH

2

OCH

3

OCH

3

O

—

T

120

588

H

C

2

H

5

Cl

NH

—

T

120

589

H

C

2

H

5

Cl

O

—

T

120

590

H

(CH

2

)

4

O

—

T

120

591

H

CH

2

OCH

3

OCH

3

NH

—

T

121

592

H

CH

2

OCH

3

OCH

3

O

—

T

121

593

H

C

2

H

5

Cl

NH

—

T

121

594

H

C

2

H

5

Cl

O

—

T

121

595

H

(CH

2

)

4

O

—

T

121

596

H

CH

2

OCH

3

OCH

3

NH

—

T

122

597

H

CH

2

OCH

3

OCH

3

O

—

T

122

598

H

C

2

H

5

Cl

NH

—

T

122

599

H

C

2

H

5

Cl

O

—

T

122

600

H

(CH

2

)

4

O

—

T

122

601

H

CH

2

OCH

3

OCH

3

NH

—

T

123

602

H

CH

2

OCH

3

OCH

3

O

—

T

123

oil

603

H

C

2

H

5

Cl

NH

—

T

123

604

H

C

2

H

5

Cl

O

—

T

123

605

H

(CH

2

)

4

O

—

T

123

63-73

606

H

CH

2

OCH

3

OCH

3

NH

—

T

124

607

H

CH

2

OCH

3

OCH

3

O

—

T

124

608

H

C

2

H

5

Cl

NH

—

T

124

609

H

C

2

H

5

Cl

O

—

T

124

610

H

(CH

2

)

4

O

—

T

124

611

H

CH

2

OCH

3

OCH

3

NH

—

T

125

612

H

CH

2

OCH

3

OCH

3

O

—

T

125

613

H

C

2

H

5

Cl

NH

—

T

125

614

H

C

2

H

5

Cl

O

—

T

125

615

H

(CH

2

)

4

O

—

T

125

616

H

CH

2

OCH

3

OCH

3

NH

—

T

126

617

H

CH

2

OCH

3

OCH

3

O

—

T

126

618

H

C

2

H

5

Cl

NH

—

T

126

619

H

C

2

H

5

Cl

O

—

T

126

620

H

(CH

2

)

4

O

—

T

126

621

H

CH

2

OCH

3

OCH

3

NH

—

T

127

622

H

CH

2

OCH

3

OCH

3

O

—

T

127

623

H

C

2

H

5

Cl

NH

—

T

127

624

H

C

2

H

5

Cl

O

—

T

127

625

H

(CH

2

)

4

O

—

T

127

626

H

CH

2

OCH

3

OCH

3

NH

—

T

128

627

H

CH

2

OCH

3

OCH

3

O

—

T

128

628

H

C

2

H

5

Cl

NH

—

T

128

629

H

C

2

H

5

Cl

O

—

T

128

630

H

(CH

2

)

4

O

—

T

128

631

H

CH

2

OCH

3

OCH

3

NH

—

T

129

632

H

CH

2

OCH

3

OCH

3

O

—

T

129

633

H

C

2

H

5

Cl

NH

—

T

129

634

H

C

2

H

5

Cl

O

—

T

129

635

H

(CH

2

)

4

O

—

T

129

636

H

CH

2

OCH

3

OCH

3

NH

—

T

130

637

H

CH

2

OCH

3

OCH

3

O

—

T

130

638

H

C

2

H

5

Cl

NH

—

T

130

639

H

C

2

H

5

Cl

O

—

T

130

640

H

(CH

2

)

4

O

—

T

130

641

H

CH

2

OCH

3

OCH

3

NH

—

T

131

642

H

CH

2

OCH

3

OCH

3

O

—

T

131

643

H

C

2

H

5

Cl

NH

—

T

131

644

H

C

2

H

5

Cl

O

—

T

131

645

H

(CH

2

)

4

O

—

T

131

646

H

CH

2

OCH

3

OCH

3

NH

—

T

132

647

H

CH

2

OCH

3

OCH

3

O

—

T

132

648

H

C

2

H

5

Cl

NH

—

T

132

649

H

C

2

H

5

Cl

O

—

T

132

650

H

(CH

2

)

4

O

—

T

132

651

H

CH

2

OCH

3

OCH

3

NH

—

T

133

652

H

CH

2

OCH

3

OCH

3

O

—

T

133

653

H

C

2

H

5

Cl

NH

—

T

133

654

H

C

2

H

5

Cl

O

—

T

133

655

H

(CH

2

)

4

O

—

T

133

656

H

CH

2

OCH

3

OCH

3

NH

—

T

134

657

H

CH

2

OCH

3

OCH

3

O

—

T

134

658

H

C

2

H

5

Cl

NH

—

T

134

659

H

C

2

H

5

Cl

O

—

T

134

660

H

(CH

2

)

4

O

—

T

134

661

H

CH

2

OCH

3

OCH

3

NH

—

T

135

662

H

CH

2

OCH

3

OCH

3

O

—

T

135

663

H

C

2

H

5

Cl

NH

—

T

135

664

H

C

2

H

5

Cl

O

—

T

135

665

H

(CH

2

)

4

O

—

T

135

666

H

CH

2

OCH

3

OCH

3

NH

—

T

136

667

H

CH

2

OCH

3

OCH

3

O

—

T

136

668

H

C

2

H

5

Cl

NH

—

T

136

669

H

C

2

H

5

Cl

O

—

T

136

670

H

(CH

2

)

4

O

—

T

136

671

H

CH

2

OCH

3

OCH

3

NH

—

T

137

672

H

CH

2

OCH

3

OCH

3

O

—

T

137

673

H

C

2

H

5

Cl

NH

—

T

137

674

H

C

2

H

5

Cl

O

—

T

137

675

H

(CH

2

)

4

O

—

T

137

676

H

CH

2

OCH

3

OCH

3

NH

—

T

138

677

H

CH

2

OCH

3

OCH

3

O

—

T

138

678

H

C

2

H

5

Cl

NH

—

T

138

679

H

C

2

H

5

Cl

O

—

T

138

680

H

(CH

2

)

4

O

—

T

138

681

H

CH

2

OCH

3

OCH

3

NH

—

T

139

682

H

CH

2

OCH

3

OCH

3

O

—

T

139

683

H

C

2

H

5

Cl

NH

—

T

139

684

H

C

2

H

5

Cl

O

—

T

139

685

H

(CH

2

)

4

O

—

T

139

686

H

CH

2

OCH

3

OCH

3

NH

—

T

140

687

H

CH

2

OCH

3

OCH

3

O

—

T

140

688

H

C

2

H

5

Cl

NH

—

T

140

689

H

C

2

H

5

Cl

O

—

T

140

690

H

(CH

2

)

4

O

—

T

140

691

H

CH

2

OCH

3

OCH

3

NH

—

T

141

692

H

CH

2

OCH

3

OCH

3

O

—

T

141

693

H

C

2

H

5

Cl

NH

—

T

141

65-66

694

H

C

2

H

5

Cl

O

—

T

141

695

H

(CH

2

)

4

O

—

T

141

696

H

CH

2

OCH

3

OCH

3

NH

—

T

142

697

H

CH

2

OCH

3

OCH

3

O

—

T

142

698

H

C

2

H

5

Cl

NH

—

T

142

699

H

C

2

H

5

Cl

O

—

T

142

700

H

(CH

2

)

4

O

—

T

142

701

H

CH

2

OCH

3

OCH

3

NH

—

T

143

702

H

CH

2

OCH

3

OCH

3

O

—

T

143

703

H

C

2

H

5

Cl

NH

—

T

143

704

H

C

2

H

5

Cl

O

—

T

143

705

H

(CH

2

)

4

O

—

T

143

706

H

CH

2

OCH

3

OCH

3

NH

—

T

144

707

H

CH

2

OCH

3

OCH

3

O

—

T

144

708

H

C

2

H

5

Cl

NH

—

T

144

709

H

C

2

H

5

Cl

O

—

T

144

710

H

(CH

2

)

4

O

—

T

144

711

H

CH

2

OCH

3

OCH

3

NH

—

T

145

712

H

CH

2

OCH

3

OCH

3

O

—

T

145

713

H

C

2

H

5

Cl

NH

—

T

145

714

H

C

2

H

5

Cl

O

—

T

145

715

H

(CH

2

)

4

O

—

T

145

716

H

CH

2

OCH

3

OCH

3

NH

—

T

146

717

H

CH

2

OCH

3

OCH

3

O

—

T

146

718

H

C

2

H

5

Cl

NH

—

T

146

719

H

C

2

H

5

Cl

O

—

T

146

720

H

(CH

2

)

4

O

—

T

146

721

H

CH

2

OCH

3

OCH

3

NH

—

T

147

722

H

CH

2

OCH

3

OCH

3

O

—

T

147

723

H

C

2

H

5

Cl

NH

—

T

147

724

H

C

2

H

5

Cl

O

—

T

147

725

H

(CH

2

)

4

O

—

T

147

726

H

CH

2

OCH

3

OCH

3

NH

—

T

148

727

H

CH

2

OCH

3

OCH

3

O

—

T

148

728

H

C

2

H

5

Cl

NH

—

T

148

729

H

C

2

H

5

Cl

O

—

T

148

730

H

(CH

2

)

4

O

—

T

148

731

H

CH

2

OCH

3

OCH

3

NH

—

T

149

732

H

CH

2

OCH

3

OCH

3

O

—

T

149

733

H

C

2

H

5

Cl

NH

—

T

149

734

H

C

2

H

5

Cl

O

—

T

149

735

H

(CH

2

)

4

O

—

T

149

736

H

CH

2

OCH

3

OCH

3

NH

—

T

150

737

H

CH

2

OCH

3

OCH

3

O

—

T

150

738

H

C

2

H

5

Cl

NH

—

T

150

739

H

C

2

H

5

Cl

O

—

T

150

740

H

(CH

2

)

4

O

—

T

150

741

H

CH

2

OCH

3

OCH

3

NH

—

T

151

93-94

742

H

CH

2

OCH

3

OCH

3

O

—

T

151

oil

743

H

C

2

H

5

Cl

NH

—

T

151

110-111

744

H

C

2

H

5

Cl

O

—

T

151

72

745

H

(CH

2

)

4

O

—

T

151

108

746

H

CH

2

OCH

3

OCH

3

NH

—

T

152

oil

747

H

CH

2

OCH

3

OCH

3

O

—

T

152

748

H

C

2

H

5

Cl

NH

—

T

152

87-88

749

H

C

2

H

5

Cl

O

—

T

152

750

H

(CH

2

)

4

O

—

T

152

751

H

CH

2

OCH

3

OCH

3

NH

—

T

153

752

H

CH

2

OCH

3

OCH

3

O

—

T

153

753

H

C

2

H

5

Cl

NH

—

T

153

754

H

C

2

H

5

Cl

O

—

T

153

755

H

(CH

2

)

4

O

—

T

153

756

H

CH

2

OCH

3

OCH

3

NH

—

T

154

757

H

CH

2

OCH

3

OCH

3

O

—

T

154

758

H

C

2

H

5

Cl

NH

—

T

154

oil

759

H

C

2

H

5

Cl

O

—

T

154

760

H

(CH

2

)

4

O

—

T

154

761

H

CH

2

OCH

3

OCH

3

NH

—

T

155

762

H

CH

2

OCH

3

OCH

3

O

—

T

155

763

H

C

2

H

5

Cl

NH

—

T

155

oil

764

H

C

2

H

5

Cl

O

—

T

155

765

H

(CH

2

)

4

O

—

T

155

766

H

CH

2

OCH

3

OCH

3

NH

—

T

156

767

H

CH

2

OCH

3

OCH

3

O

—

T

156

768

H

C

2

H

5

Cl

NH

—

T

156

769

H

C

2

H

5

Cl

O

—

T

156

770

H

(CH

2

)

4

O

—

T

156

771

H

CH

2

OCH

3

OCH

3

NH

—

T

157

772

H

CH

2

OCH

3

OCH

3

O

—

T

157

773

H

C

2

H

5

Cl

NH

—

T

157

774

H

C

2

H

5

Cl

O

—

T

157

775

H

(CH

2

)

4

O

—

T

157

776

H

CH

2

OCH

3

OCH

3

NH

—

T

158

777

H

CH

2

OCH

3

OCH

3

O

—

T

158

778

H

C

2

H

5

Cl

NH

—

T

158

779

H

C

2

H

5

Cl

O

—

T

158

780

H

(CH

2

)

4

O

—

T

158

781

H

CH

2

OCH

3

OCH

3

NH

—

T

159

782

H

CH

2

OCH

3

OCH

3

O

—

T

159

783

H

C

2

H

5

Cl

NH

—

T

159

784

H

C

2

H

5

Cl

O

—

T

159

785

H

(CH

2

)

4

O

—

T

159

786

H

CH

2

OCH

3

OCH

3

NH

—

T

160

oil

787

H

CH

2

OCH

3

OCH

3

O

—

T

160

788

H

C

2

H

5

Cl

NH

—

T

160

oil

789

H

C

2

H

5

Cl

O

—

T

160

790

H

(CH

2

)

4

O

—

T

160

791

H

CH

2

OCH

3

OCH

3

NH

—

T

161

oil

792

H

CH

2

OCH

3

OCH

3

O

—

T

161

793

H

C

2

H

5

Cl

NH

—

T

161

oil

794

H

C

2

H

5

Cl

O

—

T

161

795

H

(CH

2

)

4

O

—

T

161

796

H

CH

2

OCH

3

OCH

3

NH

—

T

162

797

H

CH

2

OCH

3

OCH

3

O

—

T

162

798

H

C

2

H

5

Cl

NH

—

T

162

799

H

C

2

H

5

Cl

O

—

T

162

800

H

(CH

2

)

4

O

—

T

162

801

H

CH

2

OCH

3

OCH

3

NH

—

T

163

802

H

CH

2

OCH

3

OCH

3

O

—

T

163

803

H

C

2

H

5

Cl

NH

—

T

163

804

H

C

2

H

5

Cl

O

—

T

163

805

H

(CH

2

)

4

O

—

T

163

806

H

CH

2

OCH

3

OCH

3

NH

—

T

164

807

H

CH

2

OCH

3

OCH

3

O

—

T

164

808

H

C

2

H

5

Cl

NH

—

T

164

809

H

C

2

H

5

Cl

O

—

T

164

810

H

(CH

2

)

4

O

—

T

164

811

H

CH

2

OCH

3

OCH

3

NH

—

T

165

812

H

CH

2

OCH

3

OCH

3

O

—

T

165

813

H

C

2

H

5

Cl

NH

—

T

165

814

H

C

2

H

5

Cl

O

—

T

165

815

H

(CH

2

)

4

O

—

T

165

816

H

CH

2

OCH

3

OCH

3

NH

—

T

166

817

H

CH

2

OCH

3

OCH

3

O

—

T

166

818

H

C

2

H

5

Cl

NH

—

T

166

819

H

C

2

H

5

Cl

O

—

T

166

820

H

(CH

2

)

4

O

—

T

166

821

H

CH

2

OCH

3

OCH

3

NH

—

T

167

822

H

CH

2

OCH

3

OCH

3

O

—

T

167

823

H

C

2

H

5

Cl

NH

—

T

167

824

H

C

2

H

5

Cl

O

—

T

167

825

H

(CH

2

)

4

O

—

T

167

826

H

CH

2

OCH

3

OCH

3

NH

—

T

168

827

H

CH

2

OCH

3

OCH

3

O

—

T

168

828

H

C

2

H

5

Cl

NH

—

T

168

829

H

C

2

H

5

Cl

O

—

T

168

830

H

(CH

2

)

4

O

—

T

168

831

H

CH

2

OCH

3

OCH

3

NH

—

T

169

832

H

CH

2

OCH

3

OCH

3

O

—

T

169

833

H

C

2

H

5

Cl

NH

—

T

169

834

H

C

2

H

5

Cl

O

—

T

169

835

H

(CH

2

)

4

O

—

T

169

836

H

CH

2

OCH

3

OCH

3

NH

—

T

170

837

H

CH

2

OCH

3

OCH

3

O

—

T

170

838

H

C

2

H

5

Cl

NH

—

T

170

839

H

C

2

H

5

Cl

O

—

T

170

840

H

(CH

2

)

4

O

—

T

170

841

H

CH

2

OCH

3

OCH

3

NH

—

T

171

842

H

CH

2

OCH

3

OCH

3

O

—

T

171

843

H

C

2

H

5

Cl

NH

—

T

171

844

H

C

2

H

5

Cl

O

—

T

171

845

H

(CH

2

)

4

O

—

T

171

846

H

CH

2

OCH

3

OCH

3

NH

—

T

172

847

H

CH

2

OCH

3

OCH

3

O

—

T

172

848

H

C

2

H

5

Cl

NH

—

T

172

849

H

C

2

H

5

Cl

O

—

T

172

850

H

(CH

2

)

4

O

—

T

172

851

H

CH

2

OCH

3

OCH

3

NH

—

T

173

852

H

CH

2

OCH

3

OCH

3

O

—

T

173

853

H

C

2

H

5

Cl

NH

—

T

173

854

H

C

2

H

5

Cl

O

—

T

173

855

H

(CH

2

)

4

O

—

T

173

856

H

CH

2

OCH

3

OCH

3

NH

—

T

174

857

H

CH

2

OCH

3

OCH

3

O

—

T

174

858

H

C

2

H

5

Cl

NH

—

T

174

oil

859

H

C

2

H

5

Cl

O

—

T

174

860

H

(CH

2

)

4

O

—

T

174

861

H

CH

2

OCH

3

OCH

3

NH

—

T

175

862

H

CH

2

OCH

3

OCH

3

O

—

T

175

863

H

C

2

H

5

Cl

NH

—

T

175

oil

864

H

C

2

H

5

Cl

O

—

T

175

865

H

(CH

2

)

4

O

—

T

175

866

H

CH

2

OCH

3

OCH

3

NH

—

T

176

867

H

CH

2

OCH

3

OCH

3

O

—

T

176

868

H

C

2

H

5

Cl

NH

—

T

176

869

H

C

2

H

5

Cl

O

—

T

176

870

H

(CH

2

)

4

O

—

T

176

871

H

CH

2

OCH

3

OCH

3

NH

—

T

177

872

H

CH

2

OCH

3

OCH

3

O

—

T

177

873

H

C

2

H

5

Cl

NH

—

T

177

874

H

C

2

H

5

Cl

O

—

T

177

875

H

(CH

2

)

4

O

—

T

177

876

H

CH

2

OCH

3

OCH

3

NH

—

T

178

877

H

CH

2

OCH

3

OCH

3

O

—

T

178

878

H

C

2

H

5

Cl

NH

—

T

178

879

H

C

2

H

5

Cl

O

—

T

178

880

H

(CH

2

)

4

O

—

T

178

881

H

CH

2

OCH

3

OCH

3

NH

—

T

179

882

H

CH

2

OCH

3

OCH

3

O

—

T

179

883

H

C

2

H

5

Cl

NH

—

T

179

884

H

C

2

H

5

Cl

O

—

T

179

885

H

(CH

2

)

4

O

—

T

179

886

H

CH

2

OCH

3

OCH

3

NH

—

T

180

887

H

CH

2

OCH

3

OCH

3

O

—

T

180

888

H

C

2

H

5

Cl

NH

—

T

180

oil

889

H

C

2

H

5

Cl

O

—

T

180

890

H

(CH

2

)

4

O

—

T

180

891

H

CH

2

OCH

3

OCH

3

NH

—

T

181

892

H

CH

2

OCH

3

OCH

3

O

—

T

181

893

H

C

2

H

5

Cl

NH

—

T

181

894

H

C

2

H

5

Cl

O

—

T

181

895

H

(CH

2

)

4

O

—

T

181

896

H

CH

2

OCH

3

OCH

3

NH

—

T

182

897

H

CH

2

OCH

3

OCH

3

O

—

T

182

898

H

C

2

H

5

Cl

NH

—

T

182

899

H

C

2

H

5

Cl

O

—

T

182

900

H

(CH

2

)

4

O

—

T

182

901

H

CH

2

OCH

3

OCH

3

NH

—

T

183

902

H

CH

2

OCH

3

OCH

3

O

—

T

183

903

H

C

2

H

5

Cl

NH

—

T

183

904

H

C

2

H

5

Cl

O

—

T

183

905

H

(CH

2

)

4

O

—

T

183

906

H

CH

2

OCH

3

OCH

3

NH

—

T

184

907

H

CH

2

OCH

3

OCH

3

O

—

T

184

908

H

C

2

H

5

Cl

NH

—

T

184

909

H

C

2

H

5

Cl

O

—

T

184

910

H

(CH

2

)

4

O

—

T

184

911

H

CH

2

OCH

3

OCH

3

NH

—

T

185

912

H

CH

2

OCH

3

OCH

3

O

—

T

185

913

H

C

2

H

5

Cl

NH

—

T

185

914

H

C

2

H

5

Cl

O

—

T

185

915

H

(CH

2

)

4

O

—

T

185

916

H

CH

2

OCH

3

OCH

3

NH

—

T

186

917

H

CH

2

OCH

3

OCH

3

O

—

T

186

918

H

C

2

H

5

Cl

NH

—

T

186

oil

919

H

C

2

H

5

Cl

O

—

T

186

920

H

(CH

2

)

4

O

—

T

186

921

H

CH

2

OCH

3

OCH

3

NH

—

T

187

922

H

CH

2

OCH

3

OCH

3

O

—

T

187

923

H

C

2

H

5

Cl

NH

—

T

187

924

H

C

2

H

5

Cl

O

—

T

187

925

H

(CH

2

)

4

O

—

T

187

926

H

CH

2

OCH

3

OCH

3

NH

—

T

188

927

H

CH

2

OCH

3

OCH

3

O

—

T

188

928

H

C

2

H

5

Cl

NH

—

T

188

929

H

C

2

H

5

Cl

O

—

T

188

930

H

(CH

2

)

4

O

—

T

188

931

H

CH

2

OCH

3

OCH

3

NH

—

T

189

932

H

CH

2

OCH

3

OCH

3

O

—

T

189

933

H

C

2

H

5

Cl

NH

—

T

189

934

H

C

2

H

5

Cl

O

—

T

189

935

H

(CH

2

)

4

O

—

T

189

936

H

CH

2

OCH

3

OCH

3

NH

—

T

190

937

H

CH

2

OCH

3

OCH

3

O

—

T

190

938

H

C

2

H

5

Cl

NH

—

T

190

939

H

C

2

H

5

Cl

O

—

T

190

940

H

(CH

2

)

4

O

—

T

190

941

H

CH

2

OCH

3

OCH

3

NH

—

T

191

942

H

CH

2

OCH

3

OCH

3

O

—

T

191

943

H

C

2

H

5

Cl

NH

—

T

191

944

H

C

2

H

5

Cl

O

—

T

191

945

H

(CH

2

)

4

O

—

T

191

946

H

CH

2

OCH

3

OCH

3

NH

—

T

192

947

H

CH

2

OCH

3

OCH

3

O

—

T

192

948

H

C

2

H

5

Cl

NH

—

T

192

949

H

C

2

H

5

Cl

O

—

T

192

950

H

(CH

2

)

4

O

—

T

192

951

H

CH

2

OCH

3

OCH

3

NH

—

T

193

952

H

CH

2

OCH

3

OCH

3

O

—

T

193

953

H

C

2

H

5

Cl

NH

—

T

193

954

H

C

2

H

5

Cl

O

—

T

193

955

H

(CH

2

)

4

O

—

T

193

956

H

CH

2

OCH

3

OCH

3

NH

—

T

194

957

H

CH

2

OCH

3

OCH

3

O

—

T

194

958

H

C

2

H

5

Cl

NH

—

T

194

959

H

C

2

H

5

Cl

O

—

T

194

960

H

(CH

2

)

4

O

—

T

194

961

H

CH

2

OCH

3

OCH

3

NH

—

T

195

962

H

CH

2

OCH

3

OCH

3

O

—

T

195

963

H

C

2

H

5

Cl

NH

—

T

195

964

H

C

2

H

5

Cl

O

—

T

195

965

H

(CH

2

)

4

O

—

T

195

966

H

CH

2

OCH

3

OCH

3

NH

—

T

196

967

H

CH

2

OCH

3

OCH

3

O

—

T

196

968

H

C

2

H

5

Cl

NH

—

T

196

969

H

C

2

H

5

Cl

O

—

T

196

970

H

(CH

2

)

4

O

—

T

196

971

H

CH

2

OCH

3

OCH

3

NH

—

T

197

972

H

CH

2

OCH

3

OCH

3

O

—

T

197

973

H

C

2

H

5

Cl

NH

—

T

197

974

H

C

2

H

5

Cl

O

—

T

197

975

H

(CH

2

)

4

O

—

T

197

976

H

CH

2

OCH

3

OCH

3

NH

—

T

198

977

H

CH

2

OCH

3

OCH

3

O

—

T

198

978

H

C

2

H

5

Cl

NH

—

T

198

979

H

C

2

H

5

Cl

O

—

T

198

980

H

(CH

2

)

4

O

—

T

198

981

H

CH

2

OCH

3

OCH

3

NH

—

T

199

982

H

CH

2

OCH

3

OCH

3

O

—

T

199

983

H

C

2

H

5

Cl

NH

—

T

199

984

H

C

2

H

5

Cl

O

—

T

199

985

H

(CH

2

)

4

O

—

T

199

986

H

CH

2

OCH

3

OCH

3

NH

—

T

200

987

H

CH

2

OCH

3

OCH

3

O

—

T

200

988

H

C

2

H

5

Cl

NH

—

T

200

989

H

C

2

H

5

Cl

O

—

T

200

990

H

(CH

2

)

4

—

O

T

200

991

H

CH

2

OCH

3

OCH

3

—

NH

T

201

992

H

CH

2

OCH

3

OCH

3

—

O

T

201

993

H

C

2

H

5

Cl

—

NH

T

201

994

H

C

2

H

5

Cl

—

O

T

201

995

H

(CH

2

)

4

—

O

T

201

996

H

C

2

H

5

Cl

—

NH

T

4

177-178

997

H

C

2

H

5

Cl

—

NH

T

7

177-178

998

H

C

2

H

5

I

—

NH

T

7

999

H

C

2

H

5

I

—

NH

T

14

1000

H

(CH

2

)

2

CH

3

Cl

—

NH

T

23

1001

H

C

2

H

5

I

—

NH

T

76

1002

H

CH

2

OCH

3

OCH

3

—

NH

T

202

1003

H

CH

2

OCH

3

OCH

3

—

O

T

202

1004

H

C

2

H

5

Cl

—

NH

T

202

1005

H

C

2

H

5

OCH

3

—

O

T

202

1006

H

(CH

2

)

4

—

O

T

202

1007

H

CH

2

OCH

3

OCH

3

NH

—

T

203

1008

H

CH

2

OCH

3

OCH

3

O

—

T

203

1009

H

C

2

H

5

Cl

NH

—

T

203

1010

H

C

2

H

5

Cl

O

—

T

203

1011

H

(CH

2

)

4

O

—

T

203

1012

H

CH

2

OCH

3

OCH

3

NH

—

T

204

1013

H

CH

2

OCH

3

OCH

3

O

—

T

204

1014

H

C

2

H

5

Cl

NH

—

T

204

1015

H

C

2

H

5

Cl

O

—

T

204

1016

H

(CH

2

)

4

O

—

T

204

1017

H

CH

2

OCH

3

OCH

3

NH

—

T

205

1018

H

CH

2

OCH

3

OCH

3

O

—

T

205

1019

H

C

2

H

5

Cl

NH

—

T

205

1020

H

C

2

H

5

Cl

O

—

T

205

1021

H

(CH

2

)

4

O

—

T

206

1022

H

CH

2

OCH

3

OCH

3

NH

—

T

206

1023

H

CH

2

OCH

3

OCH

3

O

—

T

206

1024

H

C

2

H

5

Cl

NH

—

T

206

1025

H

C

2

H

5

Cl

O

—

T

206

1026

H

(CH

2

)

4

O

—

T

206

1027

H

CH

2

OCH

3

OCH

3

NH

—

T

207

1028

H

CH

2

OCH

3

OCH

3

O

—

T

207

1029

H

C

2

H

5

Cl

NH

—

T

207

1030

H

C

2

H

5

Cl

O

—

T

207

1031

H

(CH

2

)

4

O

—

T

207

1032

H

CH

2

OCH

3

OCH

3

NH

—

T

208

1033

H

CH

2

OCH

3

OCH

3

O

—

T

208

1034

H

C

2

H

5

Cl

NH

—

T

208

1035

H

C

2

H

5

Cl

O

—

T

208

1036

H

(CH

2

)

4

O

—

T

208

1037

H

CH

2

OCH

3

OCH

3

NH

—

T

209

1038

H

CH

2

OCH

3

OCH

3

O

—

T

209

1039

H

C

2

H

5

Cl

NH

—

T

209

1040

H

C

2

H

5

Cl

O

—

T

209

1041

H

(CH

2

)

4

O

—

T

209

1042

H

CH

2

OCH

3

OCH

3

NH

—

T

210

1043

H

CH

2

OCH

3

OCH

3

O

—

T

210

1044

H

C

2

H

5

Cl

NH

—

T

210

1045

H

C

2

H

5

Cl

O

—

T

210

1046

H

(CH

2

)

4

O

—

T

210

1047

H

CH

2

OCH

3

OCH

3

NH

—

T

211

1048

H

CH

2

OCH

3

OCH

3

O

—

T

211

1049

H

C

2

H

5

Cl

NH

—

T

211

1050

H

C

2

H

5

Cl

O

—

T

211

1051

H

(CH

2

)

4

O

—

T

211

1052

H

CH

2

OCH

3

OCH

3

NH

—

T

212

1053

H

CH

2

OCH

3

OCH

3

O

—

T

212

1054

H

C

2

H

5

Cl

NH

—

T

212

1055

H

C

2

H

5

Cl

O

—

T

212

1056

H

(CH

2

)

4

O

—

T

212

1057

H

CH

2

OCH

3

OCH

3

NH

—

T

213

1058

H

CH

2

OCH

3

OCH

3

—

O

T

213

1059

H

C

2

H

5

Cl

—

NH

T

213

1060

H

C

2

H

5

Cl

—

O

T

213

1061

H

(CH

2

)

4

—

O

T

213

1062

H

CH

2

OCH

3

OCH

3

—

NH

T

214

1063

H

CH

2

OCH

3

OCH

3

—

O

T

214

1064

H

C

2

H

5

Cl

—

NH

T

214

1065

H

C

2

H

5

Cl

—

O

T

214

1066

H

(CH

2

)

4

—

O

T

214

1067

H

CH

2

OCH

3

OCH

3

—

NH

T

215

1068

H

CH

2

OCH

3

OCH

3

—

O

T

215

1069

H

C

2

H

5

Cl

—

NH

T

215

1070

H

C

2

H

5

Cl

—

O

T

215

1071

H

(CH

2

)

4

—

O

T

215

1072

H

CH

2

OCH

3

OCH

3

—

NH

T

216

1073

H

CH

2

OCH

3

OCH

3

—

O

T

216

1074

H

C

2

H

5

Cl

—

NH

T

216

1075

H

C

2

H

5

Cl

O

—

T

216

1076

H

(CH

2

)

4

O

—

T

216

1077

H

CH

2

OCH

3

OCH

3

NH

—

T

217

1078

H

CH

2

OCH

3

OCH

3

O

—

T

217

1079

H

C

2

H

5

Cl

NH

—

T

217

1080

H

C

2

H

5

Cl

O

—

T

217

1081

H

(CH

2

)

4

O

—

T

217

1082

H

CH

2

OCH

3

OCH

3

NH

—

T

218

1083

H

CH

2

OCH

3

OCH

3

O

—

T

218

1084

H

C

2

H

5

Cl

NH

—

T

218

1085

H

C

2

H

5

Cl

O

—

T

218

1086

H

(CH

2

)

4

O

—

T

218

1087

H

CH

2

OCH

3

OCH

3

NH

—

T

219

1088

H

CH

2

OCH

3

OCH

3

O

—

T

219

1089

H

C

2

H

5

Cl

NH

—

T

219

1090

H

C

2

H

5

Cl

O

—

T

219

1091

H

(CH

2

)

4

O

—

T

219

1092

H

CH

2

OCH

3

OCH

3

NH

—

T

220

1093

H

CH

2

OCH

3

OCH

3

O

—

T

220

1094

H

C

2

H

5

Cl

NH

—

T

220

1095

H

C

2

H

5

Cl

O

—

T

220

1096

H

(CH

2

)

4

O

—

T

220

1097

H

CH

2

OCH

3

OCH

3

NH

—

T

221

1098

H

CH

2

OCH

3

OCH

3

O

—

T

221

1099

H

C

2

H

5

Cl

NH

—

T

221

1100

H

C

2

H

5

Cl

O

—

T

221

1101

H

(CH

2

)

4

O

—

T

221

1102

H

CH

2

OCH

3

OCH

3

NH

—

T

222

1103

H

CH

2

OCH

3

OCH

3

O

—

T

222

1104

H

C

2

H

5

Cl

NH

—

T

222

1105

H

C

2

H

5

Cl

O

—

T

222

1106

H

(CH

2

)

4

O

—

T

222

1107

H

CH

2

OCH

3

OCH

3

NH

—

T

223

1108

H

CH

2

OCH

3

OCH

3

O

—

T

223

1109

H

C

2

H

5

Cl

NH

—

T

223

1110

H

C

2

H

5

Cl

O

—

T

223

1111

H

(CH

2

)

4

O

—

T

223

1112

H

CH

2

OCH

3

OCH

3

NH

—

T

225

1113

H

CH

2

OCH

3

OCH

3

O

—

T

225

1114

H

C

2

H

5

Cl

NH

—

T

225

1115

H

C

2

H

5

Cl

O

—

T

225

1116

H

(CH

2

)

4

O

—

T

225

1117

H

CH

2

OCH

3

OCH

3

NH

—

T

226

1118

H

CH

2

OCH

3

OCH

3

O

—

T

226

1119

H

C

2

H

5

Cl

NH

—

T

226

1120

H

C

2

H

5

Cl

O

—

T

226

1121

H

(CH

2

)

4

O

—

T

226

1122

H

CH

2

OCH

3

OCH

3

NH

—

T

227

1123

H

CH

2

OCH

3

OCH

3

O

—

T

227

1124

H

C

2

H

5

Cl

NH

—

T

227

1125

H

C

2

H

5

Cl

O

—

T

227

1126

H

(CH

2

)

4

O

—

T

227

1127

H

CH

2

OCH

3

OCH

3

NH

—

T

228

1128

H

CH

2

OCH

3

OCH

3

O

—

T

228

1129

H

C

2

H

5

Cl

NH

—

T

228

1130

H

C

2

H

5

Cl

O

—

T

228

1131

H

(CH

2

)

4

O

—

T

228

1132

H

CH

2

OCH

3

OCH

3

NH

—

T

229

1133

H

CH

2

OCH

3

OCH

3

O

—

T

229

1134

H

C

2

H

5

Cl

NH

—

T

229

1135

H

C

2

H

5

Cl

O

—

T

229

1136

H

(CH

2

)

4

O

—

T

229

1137

H

CH

2

OCH

3

OCH

3

NH

—

T

230

1138

H

CH

2

OCH

3

OCH

3

O

—

T

230

1139

H

C

2

H

5

Cl

NH

—

T

230

1140

H

C

2

H

5

Cl

O

—

T

230

1141

H

(CH

2

)

4

O

—

T

230

1142

H

CH

2

OCH

3

OCH

3

NH

—

T

231

1143

H

CH

2

OCH

3

OCH

3

O

—

T

231

1144

H

C

2

H

5

Cl

NH

—

T

231

1145

H

C

2

H

5

Cl

O

—

T

231

1146

H

(CH

2

)

4

O

—

T

231

1147

H

CH

2

OCH

3

OCH

3

NH

—

T

232

1148

H

CH

2

OCH

3

OCH

3

O

—

T

232

1149

H

C

2

H

5

Cl

NH

—

T

232

1150

H

C

2

H

5

Cl

O

—

T

232

1151

H

(CH

2

)

4

O

—

T

232

1152

H

CH

2

OCH

3

OCH

3

NH

—

T

233

1153

H

CH

2

OCH

3

OCH

3

O

—

T

233

1154

H

C

2

H

5

Cl

NH

—

T

233

1155

H

C

2

H

5

Cl

O

—

T

233

1156

H

(CH

2

)

4

O

—

T

233

1157

H

CH

2

OCH

3

OCH

3

NH

—

T

234

1158

H

CH

2

OCH

3

OCH

3

O

—

T

234

1159

H

C

2

H

5

Cl

NH

—

T

234

1160

H

C

2

H

5

Cl

O

—

T

234

1161

H

(CH

2

)

4

O

—

T

234

1162

H

CH

2

OCH

3

OCH

3

NH

—

T

235

1163

H

CH

2

OCH

3

OCH

3

O

—

T

235

1164

H

C

2

H

5

Cl

NH

—

T

235

1165

H

C

2

H

5

Cl

O

—

T

235

1166

H

(CH

2

)

4

O

—

T

235

1167

H

CH

2

OCH

3

OCH

3

NH

—

T

236

1168

H

CH

2

OCH

3

OCH

3

O

—

T

236

1169

H

C

2

H

5

Cl

NH

—

T

236

1170

H

C

2

H

5

Cl

O

—

T

236

1171

H

(CH

2

)

4

O

—

T

236

1172

H

CH

2

OCH

3

OCH

3

NH

—

T

237

1173

H

CH

2

OCH

3

OCH

3

O

—

T

237

1174

H

C

2

H

5

Cl

NH

—

T

237

1175

H

C

2

H

5

Cl

O

—

T

237

1176

H

(CH

2

)

4

O

—

T

237

1177

H

CH

2

OCH

3

OCH

3

NH

—

T

238

1178

H

CH

2

OCH

3

OCH

3

O

—

T

238

1179

H

C

2

H

5

Cl

NH

—

T

238

1180

H

C

2

H

5

Cl

O

—

T

238

1181

H

(CH

2

)

4

O

—

T

238

1182

H

CH

2

OCH

3

OCH

3

NH

—

T

239

1183

H

CH

2

OCH

3

OCH

3

O

—

T

239

1184

H

C

2

H

5

Cl

NH

—

T

239

1185

H

C

2

H

5

Cl

O

—

T

239

1186

H

(CH

2

)

4

O

—

T

239

1187

H

CH

2

OCH

3

OCH

3

NH

—

T

240

1188

H

CH

2

OCH

3

OCH

3

O

—

T

240

1189

H

C

2

H

5

Cl

NH

—

T

240

1190

H

C

2

H

5

Cl

O

—

T

240

1191

H

(CH

2

)

4

O

—

T

240

1192

H

CH

2

OCH

3

OCH

3

NH

—

T

241

1193

H

CH

2

OCH

3

OCH

3

O

—

T

241

1194

H

C

2

H

5

Cl

NH

—

T

241

1195

H

C

2

H

5

Cl

O

—

T

241

1196

H

(CH

2

)

4

O

—

T

241

1197

H

CH

2

OCH

3

OCH

3

NH

—

T

242

1198

H

CH

2

OCH

3

OCH

3

O

—

T

242

1199

H

C

2

H

5

Cl

NH

—

T

242

1200

H

C

2

H

5

Cl

O

—

T

242

1201

H

(CH

2

)

4

O

—

T

242

1202

H

CH

2

OCH

3

OCH

3

NH

—

T

243

1203

H

CH

2

OCH

3

OCH

3

O

—

T

243

1204

H

C

2

H

5

Cl

NH

—

T

243

1205

H

C

2

H

5

Cl

O

—

T

243

1206

H

(CH

2

)

4

O

—

T

243

1207

H

CH

2

OCH

3

OCH

3

NH

—

T

244

1208

H

CH

2

OCH

3

OCH

3

O

—

T

244

1209

H

C

2

H

5

Cl

NH

—

T

244

1210

H

C

2

H

5

Cl

O

—

T

244

1211

H

(CH

2

)

4

O

—

T

244

1212

H

CH

2

OCH

3

OCH

3

NH

—

T

245

1213

H

CH

2

OCH

3

OCH

3

O

—

T

245

1214

H

C

2

H

5

Cl

NH

—

T

245

1215

H

C

2

H

5

Cl

O

—

T

245

1216

H

(CH

2

)

4

O

—

T

245

1217

H

CH

2

OCH

3

OCH

3

NH

—

T

246

1218

H

CH

2

OCH

3

OCH

3

O

—

T

246

1219

H

C

2

H

5

Cl

NH

—

T

246

1220

H

C

2

H

5

Cl

O

—

T

246

1221

H

(CH

2

)

4

O

—

T

246

1222

H

CH

2

OCH

3

OCH

3

NH

—

T

247

1223

H

CH

2

OCH

3

OCH

3

O

—

T

247

1224

H

C

2

H

5

Cl

NH

—

T

247

1225

H

C

2

H

5

Cl

O

—

T

247

1226

H

(CH

2

)

4

O

—

T

247

1227

H

CH

2

OCH

3

OCH

3

NH

—

T

248

1228

H

CH

2

OCH

3

OCH

3

O

—

T

248

1229

H

C

2

H

5

Cl

NH

—

T

248

1230

H

C

2

H

5

Cl

O

—

T

248

1231

H

(CH

2

)

4

O

—

T

248

TABLE II

Example

No.

R

7

R

8

R

9

R

10

X

E

Q

M.p. [° C.]

1232

H

H

H

H

NH

—

T

7

135-137

1233

H

H

H

H

O

—

T

7

1234

H

Cl

H

H

NH

—

T

7

1235

H

Cl

H

H

O

—

T

7

1236

H

H

Cl

H

NH

—

T

7

1237

H

H

Cl

H

O

—

T

7

1238

CH

3

H

H

H

NH

—

T

7

1239

CH

3

H

H

H

O

—

T

7

1240

H

H

CH

3

H

NH

—

T

7

1241

H

H

CH

3

H

O

—

T

7

1242

H

H

H

CH

3

NH

—

T

7

1243

H

H

H

CH

3

O

—

T

7

1244

H

H

H

H

NH

—

T

6

140-142

1245

H

H

H

H

NH

—

T

9

90-92

1246

H

H

H

H

O

—

T

9

oil

1247

H

H

H

H

NH

—

T

8

143-145

1248

H

H

H

H

O

—

T

8

1249

H

H

H

H

NH

—

T

4

158-160

1250

H

H

H

H

O

—

T

4

1251

H

H

H

H

NH

—

T

10

1252

H

H

H

H

O

—

T

10

1253

H

H

H

H

NH

—

T

11

1254

H

H

H

H

O

—

T

11

1255

H

H

H

H

NH

—

T

12

1256

H

H

H

H

O

—

T

12

1257

H

H

H

H

NH

—

T

14

1258

H

H

H

H

O

—

T

14

1259

H

H

H

H

NH

—

T

22

210-211

1260

H

H

H

H

NH

—

T

23

153-155

1261

H

H

H

H

O

—

T

23

1262

H

H

H

H

NH

—

T

23

1263

F

H

H

H

O

—

T

23

1264

H

H

Cl

H

NH

—

T

23

1265

H

H

Cl

H

O

—

T

23

1266

Cl

H

H

H

NH

—

T

23

1267

Cl

H

H

H

O

—

T

23

1268

H

H

CH

3

H

NH

—

T

23

1269

H

H

CH

3

H

O

—

T

23

1270

H

H

H

CH

3

NH

—

T

23

1271

H

H

H

CH

3

O

—

T

23

1272

H

H

H

H

NH

—

T

58

184-185

1273

H

H

H

H

NH

—

T

13

1274

H

H

H

H

O

—

T

13

1275

H

H

H

H

NH

—

T

16

1276

H

H

H

H

O

—

T

16

1277

H

H

H

H

NH

—

T

17

1278

H

H

H

H

O

—

T

17

1279

H

H

H

H

NH

—

T

19

1280

H

H

H

H

O

—

T

19

1281

H

H

H

H

NH

—

T

24

155-157

1282

H

H

H

H

O

—

T

24

1283

H

H

H

H

NH

—

T

25

1284

H

H

H

H

O

—

T

25

1285

H

H

H

H

NH

—

T

26

1286

H

H

H

H

O

—

T

26

1287

H

H

H

H

NH

—

T

27

1288

H

H

H

H

O

—

T

27

1289

H

H

H

H

NH

—

T

28

1290

H

H

H

H

O

—

T

28

1291

H

H

H

H

NH

—

T

29

1292

H

H

H

H

O

—

T

29

1293

H

H

H

H

NH

—

T

30

1294

H

H

H

H

O

—

T

30

1295

H

H

H

H

NH

—

T

31

1296

H

H

H

H

O

—

T

31

1297

H

H

H

H

NH

—

T

32

1298

H

H

H

H

O

—

T

32

1299

H

H

H

H

NH

—

T

33

1300

H

H

H

H

O

—

T

33

1301

H

H

H

H

NH

—

T

34

1302

H

H

H

H

O

—

T

34

1303

H

H

H

H

NH

—

T

35

1304

H

H

H

H

O

—

T

35

1305

H

H

H

H

NH

—

T

36

1306

H

H

H

H

O

—

T

36

1307

H

H

H

H

NH

—

T

37

1308

H

H

H

H

O

—

T

37

1309

H

H

H

H

NH

—

T

38

1310

H

H

H

H

O

—

T

38

1311

H

H

H

H

NH

—

T

39

1312

H

H

H

H

O

—

T

39

1313

H

H

H

H

NH

—

T

40

1314

H

H

H

H

O

—

T

40

1315

H

H

H

H

NH

—

T

41

1316

H

H

H

H

O

—

T

41

1317

H

H

H

H

NH

—

T

42

1318

H

H

H

H

O

—

T

42

1319

H

H

H

H

NH

—

T

44

1320

H

H

H

H

O

—

T

44

1321

H

H

H

H

NH

—

T

45

1322

H

H

H

H

O

—

T

45

1323

H

H

H

H

NH

—

T

47

1324

H

H

H

H

O

—

T

47

1325

H

H

H

H

NH

—

T

50

1326

H

H

H

H

O

—

T

50

1327

H

H

H

H

NH

—

T

51

1328

H

H

H

H

O

—

T

51

1329

H

H

H

H

NH

—

T

52

1330

H

H

H

H

O

—

T

52

1331

H

H

H

H

NH

—

T

54

1332

H

H

H

H

O

—

T

54

1333

H

H

H

H

NH

—

T

55

1334

H

H

H

H

O

—

T

55

121

1335

H

H

H

H

NH

—

T

56

1336

H

H

H

H

O

—

T

56

1337

H

H

H

H

NH

—

T

59

144-145

1338

H

H

H

H

O

—

T

59

1339

H

H

H

H

NH

—

T

60

1340

H

H

H

H

O

—

T

60

1341

H

H

H

H

NH

—

T

61

1342

H

H

H

H

O

—

T

61

1343

H

H

H

H

NH

—

T

62

176

1344

H

H

H

H

O

—

T

62

117

1345

H

H

H

H

NH

—

T

66

1346

H

H

H

H

O

—

T

66

oil

1347

H

H

H

H

NH

—

T

67

1348

H

H

H

H

O

—

T

67

1349

H

H

H

H

NH

—

T

68

glass

1350

H

H

H

H

O

—

T

68

oil

1351

H

H

H

H

NH

—

T

69

1352

H

H

H

H

O

—

T

69

69-72

1353

H

H

H

H

NH

—

T

70

1354

H

H

H

H

O

—

T

70

1355

H

H

H

H

NH

—

T

72

1356

H

H

H

H

O

—

T

72

1357

H

H

H

H

NH

—

T

73

1358

H

H

H

H

O

—

T

73

1359

H

H

H

H

NH

—

T

74

1360

H

H

H

H

O

—

T

74

161

1361

H

H

H

H

NH

—

T

75

1362

H

H

H

H

O

—

T

75

1363

H

H

H

H

NH

—

T

76

160-161

1364

H

H

H

H

O

—

T

76

103

1365

H

H

H

H

NH

—

T

77

224-225

1366

H

H

H

H

O

—

T

77

1367

H

H

H

H

NH

—

T

78

1368

H

H

H

H

O

—

T

78

1369

H

H

H

H

NH

—

T

79

1370

H

H

H

H

O

—

T

79

1371

H

H

H

H

NH

—

T

80

1372

H

H

H

H

O

—

T

80

104

1373

H

H

H

H

NH

—

T

81

1374

H

H

H

H

O

—

T

81

1375

H

H

H

H

NH

—

T

82

134-136

1376

H

H

H

H

O

—

T

82

1377

H

H

H

H

NH

—

T

83

158-160

1378

H

H

H

H

O

—

T

83

1379

H

H

H

H

NH

—

T

84

1380

H

H

H

H

O

—

T

84

1381

H

H

H

H

NH

—

T

85

1382

H

H

H

H

O

—

T

85

1383

H

H

H

H

NH

—

T

86

1384

H

H

H

H

O

—

T

86

1385

H

H

H

H

NH

—

T

87

123-124

1386

H

H

H

H

O

—

T

87

75

1387

H

H

H

H

NH

—

T

88

156-157

1388

H

H

H

H

O

—

T

88

1389

H

H

H

H

NH

—

T

89

1390

H

H

H

H

O

—

T

89

65

1391

H

H

H

H

NH

—

T

90

1392

H

H

H

H

O

—

T

90

1393

H

H

H

H

NH

—

T

91

1394

H

H

H

H

O

—

T

91

1395

H

H

H

H

NH

—

T

92

1396

H

H

H

H

O

—

T

92

1397

H

H

H

H

NH

—

T

93

1398

H

H

H

H

O

—

T

93

1399

H

H

H

H

NH

—

T

94

1400

H

H

H

H

O

—

T

94

78-81

1401

H

H

H

H

NH

—

T

95

1402

H

H

H

H

O

—

T

95

57

1403

H

H

H

H

NH

—

T

96

1404

H

H

H

H

O

—

T

96

1405

H

H

H

H

NH

—

T

97

1406

H

H

H

H

O

—

T

97

97

1407

H

H

H

H

NH

—

T

98

1408

H

H

H

H

O

—

T

98

1409

H

H

H

H

NH

—

T

99

1410

H

H

H

H

O

—

T

99

1411

H

H

H

H

NH

—

T

100

1412

H

H

H

H

O

—

T

100

1413

H

H

H

H

NH

—

T

101

1414

H

H

H

H

O

—

T

101

1415

H

H

H

H

NH

—

T

102

1416

H

H

H

H

O

—

T

102

1417

H

H

H

H

NH

—

T

103

1418

H

H

H

H

O

—

T

103

1419

H

H

H

H

NH

—

T

104

1420

H

H

H

H

O

—

T

104

107

1421

H

H

H

H

NH

—

T

105

1422

H

H

H

H

O

—

T

105

1423

H

H

H

H

NH

—

T

106

1424

H

H

H

H

O

—

T

106

1425

H

H

H

H

NH

—

T

107

1426

H

H

H

H

O

—

T

107

oil

1427

H

H

H

H

NH

—

T

108

1428

H

H

H

H

O

—

T

108

1429

H

H

H

H

NH

—

T

109

1430

H

H

H

H

O

—

T

109

1431

H

H

H

H

NH

—

T

110

1432

H

H

H

H

O

—

T

110

1433

H

H

H

H

NH

—

T

111

1434

H

H

H

H

O

—

T

111

oil

1435

H

H

H

H

NH

—

T

112

1436

H

H

H

H

O

—

T

112

oil

1437

H

H

H

H

NH

—

T

113

1438

H

H

H

H

O

—

T

113

1439

H

H

H

H

NH

—

T

114

1440

H

H

H

H

O

—

T

114

1441

H

H

H

H

NH

—

T

115

1442

H

H

H

H

O

—

T

115

oil

1443

H

H

H

H

NH

—

T

116

1444

H

H

H

H

O

—

T

116

1445

H

H

H

H

NH

—

T

117

1446

H

H

H

H

O

—

T

117

1447

H

H

H

H

NH

—

T

118

1448

H

H

H

H

O

—

T

118

oil

1449

H

H

H

H

NH

—

T

119

1450

H

H

H

H

O

—

T

119

1451

H

H

H

H

NH

—

T

120

1452

H

H

H

H

O

—

T

120

1453

H

H

H

H

NH

—

T

121

1454

H

H

H

H

O

—

T

121

1455

H

H

H

H

NH

—

T

122

1456

H

H

H

H

O

—

T

122

oil

1457

H

H

H

H

NH

—

T

123

1458

H

H

H

H

O

—

T

123

80

1459

H

H

H

H

NH

—

T

124

1460

H

H

H

H

O

—

T

124

1461

H

H

H

H

NH

—

T

125

1462

H

H

H

H

O

—

T

125

1463

H

H

H

H

NH

—

T

126

1464

H

H

H

H

O

—

T

126

1465

H

H

H

H

NH

—

T

127

1466

H

H

H

H

O

—

T

127

1467

H

H

H

H

NH

—

T

128

1468

H

H

H

H

O

—

T

128

1469

H

H

H

H

NH

—

T

129

1470

H

H

H

H

O

—

T

129

1471

H

H

H

H

NH

—

T

130

1472

H

H

H

H

O

—

T

130

1473

H

H

H

H

NH

—

T

131

1474

H

H

H

H

O

—

T

131

1475

H

H

H

H

NH

—

T

132

1476

H

H

H

H

O

—

T

132

1477

H

H

H

H

NH

—

T

133

1478

H

H

H

H

O

—

T

133

1479

H

H

H

H

NH

—

T

134

1480

H

H

H

H

O

—

T

134

1481

H

H

H

H

NH

—

T

135

1482

H

H

H

H

O

—

T

135

1483

H

H

H

H

NH

—

T

136

1484

H

H

H

H

O

—

T

136

1485

H

H

H

H

NH

—

T

137

1486

H

H

H

H

O

—

T

137

1487

H

H

H

H

NH

—

T

138

1488

H

H

H

H

O

—

T

138

1489

H

H

H

H

NH

—

T

139

1490

H

H

H

H

O

—

T

139

1491

H

H

H

H

NH

—

T

140

1492

H

H

H

H

O

—

T

140

1493

H

H

H

H

NH

—

T

141

1494

H

H

H

H

O

—

T

141

1495

H

H

H

H

NH

—

T

142

1496

H

H

H

H

O

—

T

142

1497

H

H

H

H

NH

—

T

143

1498

H

H

H

H

O

—

T

143

1499

H

H

H

H

NH

—

T

144

1500

H

H

H

H

O

—

T

144

1501

H

H

H

H

NH

—

T

145

1502

H

H

H

H

O

—

T

145

1503

H

H

H

H

NH

—

T

146

1504

H

H

H

H

O

—

T

146

1505

H

H

H

H

NH

—

T

147

1506

H

H

H

H

O

—

T

147

1507

H

H

H

H

NH

—

T

148

1508

H

H

H

H

O

—

T

148

1509

H

H

H

H

NH

—

T

149

1510

H

H

H

H

O

—

T

149

1511

H

H

H

H

NH

—

T

150

1512

H

H

H

H

O

—

T

150

1513

H

H

H

H

NH

—

T

151

188-189

1514

H

H

H

H

O

—

T

151

118

1515

H

H

H

H

NH

—

T

152

1516

H

H

H

H

O

—

T

152

1517

H

H

H

H

NH

—

T

153

1518

H

H

H

H

O

—

T

153

1519

H

H

H

H

NH

—

T

154

1520

H

H

H

H

O

—

T

154

1521

H

H

H

H

NH

—

T

155

1522

H

H

H

H

O

—

T

155

1523

H

H

H

H

NH

—

T

156

1524

H

H

H

H

O

—

T

156

1525

H

H

H

H

NH

—

T

157

1526

H

H

H

H

O

—

T

157

1527

H

H

H

H

NH

—

T

158

1528

H

H

H

H

O

—

T

158

1529

H

H

H

H

NH

—

T

159

1530

H

H

H

H

O

—

T

159

1531

H

H

H

H

NH

—

T

160

78-80

1532

H

H

H

H

O

—

T

160

1533

H

H

H

H

NH

—

T

161

92-94

1534

H

H

H

H

O

—

T

161

1535

H

H

H

H

NH

—

T

162

1536

H

H

H

H

O

—

T

162

1537

H

H

H

H

NH

—

T

163

1538

H

H

H

H

O

—

T

163

1539

H

H

H

H

NH

—

T

164

1540

H

H

H

H

O

—

T

164

1541

H

H

H

H

NH

—

T

165

1542

H

H

H

H

O

—

T

165

1543

H

H

H

H

NH

—

T

166

1544

H

H

H

H

O

—

T

166

1545

H

H

H

H

NH

—

T

167

1546

H

H

H

H

O

—

T

167

1547

H

H

H

H

NH

—

T

168

1548

H

H

H

H

O

—

T

168

1549

H

H

H

H

NH

—

T

169

1550

H

H

H

H

O

—

T

169

1551

H

H

H

H

NH

—

T

170

1552

H

H

H

H

O

—

T

170

1553

H

H

H

H

NH

—

T

171

1554

H

H

H

H

O

—

T

171

1555

H

H

H

H

NH

—

T

172

1556

H

H

H

H

O

—

T

172

1557

H

H

H

H

NH

—

T

173

1558

H

H

H

H

O

—

T

173

1559

H

H

H

H

NH

—

T

174

1560

H

H

H

H

O

—

T

174

1561

H

H

H

H

NH

—

T

175

1562

H

H

H

H

O

—

T

175

1563

H

H

H

H

NH

—

T

176

1564

H

H

H

H

O

—

T

176

1565

H

H

H

H

NH

—

T

177

1566

H

H

H

H

O

—

T

177

1567

H

H

H

H

NH

—

T

178

1568

H

H

H

H

O

—

T

178

1569

H

H

H

H

NH

—

T

179

1570

H

H

H

H

O

—

T

179

1571

H

H

H

H

NH

—

T

180

1572

H

H

H

H

O

—

T

180

1573

H

H

H

H

NH

—

T

181

1574

H

H

H

H

O

—

T

181

1575

H

H

H

H

NH

—

T

182

1576

H

H

H

H

O

—

T

182

1577

H

H

H

H

NH

—

T

183

1578

H

H

H

H

O

—

T

183

1579

H

H

H

H

NH

—

T

184

1580

H

H

H

H

O

—

T

184

1581

H

H

H

H

NH

—

T

185

1582

H

H

H

H

O

—

T

185

1583

H

H

H

H

NH

—

T

186

1584

H

H

H

H

O

—

T

186

1585

H

H

H

H

NH

—

T

187

1586

H

H

H

H

O

—

T

187

1587

H

H

H

H

NH

—

T

188

1588

H

H

H

H

O

—

T

188

1589

H

H

H

H

NH

—

T

189

1590

H

H

H

H

O

—

T

189

1591

H

H

H

H

NH

—

T

190

1592

H

H

H

H

O

—

T

190

1593

H

H

H

H

NH

—

T

191

1594

H

H

H

H

O

—

T

191

1595

H

H

H

H

NH

—

T

192

1596

H

H

H

H

O

—

T

192

1597

H

H

H

H

NH

—

T

193

1598

H

H

H

H

O

—

T

193

1599

H

H

H

H

NH

—

T

194

1600

H

H

H

H

O

—

T

194

1601

H

H

H

H

NH

—

T

195

1602

H

H

H

H

O

—

T

195

1603

H

H

H

H

NH

—

T

196

1604

H

H

H

H

O

—

T

196

1605

H

H

H

H

NH

—

T

197

1606

H

H

H

H

O

—

T

197

1607

H

H

H

H

NH

—

T

198

1608

H

H

H

H

O

—

T

198

1609

H

H

H

H

NH

—

T

199

1610

H

H

H

H

O

—

T

199

1611

H

H

H

H

NH

—

T

200

1612

H

H

H

H

O

—

T

200

1613

H

H

H

H

NH

—

T

201

1614

H

H

H

H

O

—

T

201

1615

H

H

H

H

NH

—

T

202

1616

H

H

H

H

O

—

T

202

1617

H

H

H

H

NH

—

T

203

1618

H

H

H

H

O

—

T

203

1619

H

H

H

H

NH

—

T

204

1620

H

H

H

H

O

—

T

204

1621

H

H

H

H

NH

—

T

205

1622

H

H

H

H

O

—

T

205

1623

H

H

H

H

NH

—

T

206

1624

H

H

H

H

O

—

T

206

1625

H

H

H

H

NH

—

T

207

1626

H

H

H

H

O

—

T

207

1627

H

H

H

H

NH

—

T

208

1628

H

H

H

H

O

—

T

208

1629

H

H

H

H

NH

—

T

209

1630

H

H

H

H

O

—

T

209

1631

H

H

H

H

NH

—

T

210

1632

H

H

H

H

O

—

T

210

1633

H

H

H

H

NH

—

T

211

1634

H

H

H

H

O

—

T

211

1635

H

H

H

H

NH

—

T

212

1636

H

H

H

H

O

—

T

212

1637

H

H

H

H

NH

—

T

213

1638

H

H

H

H

O

—

T

213

1639

H

H

H

H

NH

—

T

214

1640

H

H

H

H

O

—

T

214

1641

H

H

H

H

NH

—

T

215

1642

H

H

H

H

O

—

T

215

1643

H

H

H

H

NH

—

T

216

1644

H

H

H

H

O

—

T

216

1645

H

H

H

H

NH

—

T

217

1646

H

H

H

H

O

—

T

217

1647

H

H

H

H

NH

—

T

218

1648

H

H

H

H

O

—

T

218

1649

H

H

H

H

NH

—

T

219

1650

H

H

H

H

O

—

T

219

1651

H

H

H

H

NH

—

T

220

1652

H

H

H

H

O

—

T

220

1653

H

H

H

H

NH

—

T

221

1654

H

H

H

H

O

—

T

221

1655

H

H

H

H

NH

—

T

222

1656

H

H

H

H

O

—

T

222

1657

H

H

H

H

NH

—

T

223

1658

H

H

H

H

O

—

T

223

1659

H

H

H

H

NH

—

T

224

1660

H

H

H

H

O

—

T

224

1661

H

H

H

H

NH

—

T

225

1662

H

H

H

H

O

—

T

225

1663

H

H

H

H

NH

—

T

226

1664

H

H

H

H

O

—

T

226

1665

H

H

H

H

NH

—

T

227

1666

H

H

H

H

O

—

T

227

1667

H

H

H

H

NH

—

T

228

1668

H

H

H

H

O

—

T

228

1669

H

H

H

H

NH

—

T

229

1670

H

H

H

H

O

—

T

229

1671

H

H

H

H

NH

—

T

230

1672

H

H

H

H

O

—

T

230

1673

H

H

H

H

NH

—

T

231

1674

H

H

H

H

O

—

T

231

1675

H

H

H

H

NH

—

T

232

1676

H

H

H

H

O

—

T

232

1677

H

H

H

H

NH

—

T

233

1678

H

H

H

H

O

—

T

233

1679

H

H

H

H

NH

—

T

234

1680

H

H

H

H

O

—

T

234

1681

H

H

H

H

NH

—

T

235

1682

H

H

H

H

O

—

T

235

1683

H

H

H

H

NH

—

T

236

1684

H

H

H

H

O

—

T

236

1685

H

H

H

H

NH

—

T

237

1686

H

H

H

H

O

—

T

237

1687

H

H

H

H

NH

—

T

238

1688

H

H

H

H

O

—

T

238

1689

H

H

H

H

NH

—

T

239

1690

H

H

H

H

O

—

T

239

1691

H

H

H

H

NH

—

T

240

1692

H

H

H

H

O

—

T

240

1693

H

H

H

H

NH

—

T

241

1694

H

H

H

H

O

—

T

241

1695

H

H

H

H

NH

—

T

242

1696

H

H

H

H

O

—

T

242

1697

H

H

H

H

NH

—

T

243

1698

H

H

H

H

O

—

T

243

1699

H

H

H

H

NH

—

T

244

1700

H

H

H

H

O

—

T

244

1701

H

H

H

H

NH

—

T

245

1702

H

H

H

H

O

—

T

245

1703

H

H

H

H

NH

—

T

246

1704

H

H

H

H

O

—

T

246

1705

H

H

H

H

NH

—

T

247

1706

H

H

H

H

O

—

T

247

1707

H

H

H

H

NH

—

T

248

1708

H

H

H

H

O

—

T

248

TABLE III

Example

No.

A

B

X

E

Q

M.p. [° C.]

1709

CH

S

NH

—

T

7

1710

″

″

O

—

T

7

1711

S

CH

NH

—

T

7

1712

″

″

O

—

T

7

1713

CH

S

NH

—

T

9

1714

S

CH

O

—

T

9

1715

S

CH

NH

—

T

9

1716

″

″

O

—

T

9

1717

CH

S

NH

—

T

8

1718

″

″

O

—

T

8

1719

S

CH

NH

—

T

8

1720

″

″

O

—

T

8

1721

CH

S

NH

—

T

4

1722

″

″

O

—

T

4

1723

S

CH

NH

—

T

4

1724

″

″

O

—

T

4

1725

CH

S

NH

—

T

10

1726

″

″

O

—

T

10

1727

S

CH

NH

—

T

10

1728

S

CH

O

—

T

10

1729

CH

S

NH

—

T

11

1730

″

″

O

—

T

11

1731

S

CH

NH

—

T

11

1732

″

″

O

—

T

11

1733

CH

S

NH

—

T

12

1734

″

″

O

—

T

12

1735

S

CH

NH

—

T

12

1736

″

″

O

—

T

12

1737

CH

S

NH

—

T

14

1738

″

″

O

—

T

14

1739

S

CH

NH

—

T

14

1740

″

″

″

—

T

14

1741

CH

S

NH

T

23

118-120

1742

″

″

O

—

T

23

1743

S

CH

NH

—

T

23

1744

″

″

O

—

T

23

1745

CH

S

NH

T

58

1746

″

″

O

T

58

1747

S

CH

NH

T

58

1748

″

″

O

T

58

TABLE IV

Example

No.

X

R

M.p. [° C.]

1749

NH

238-240

1750

NH

152-154

TABLE V

Example

No.

X

M.p. [° C.]

1751

NH

T

4

1752

NH

T

7

1753

NH

T

8

1754

NH

T

9

1755

O

T

9

1756

NH

T

10

1757

NH

T

12

1758

NH

T

14

1759

NH

T

23

1760

O

T

23

1761

NH

T

66

1762

NH

T

68

1763

NH

T

70

1764

O

T

70

1765

NH

T

76

1766

O

T

76

TABLE VI

Example

No.

X

M.p. [° C.]

1767

NH

T

4

1768

NH

T

7

1769

NH

T

8

1770

NH

T

9

1771

O

T

9

1772

NH

T

10

1773

NH

T

12

1774

NH

T

14

1775

NH

T

23

1776

O

T

23

1777

NH

T

66

1778

NH

T

68

1779

NH

T

20

1780

O

T

20

1781

NH

T

76

1782

O

T

76

TABLE VII

Example

No.

X

M.p. [° C.]

1783

NH

T

4

1784

NH

T

7

1785

NH

T

8

1786

NH

T

9

1787

O

T

9

1788

NH

T

10

1789

NH

T

12

1790

NH

T

14

1791

NH

T

23

1792

O

T

23

1793

NH

T

66

1794

NH

T

68

1795

NH

T

70

1796

O

T

70

1797

NH

T

76

1798

O

T

76

TABLE VIII

Example

No.

X

M.p. [°C.]

1799

NH

T

4

1800

NH

T

7

1801

NH

T

8

1802

NH

T

9

1803

O

T

9

1804

NH

T

10

1805

NH

T

12

1806

NH

T

14

1807

NH

T

23

1808

O

T

23

1809

NH

T

66

1810

NH

T

68

1811

NH

T

70

1812

O

T

70

1813

NH

T

76

1814

O

T

76

Number	Name	Date	Kind
3470182	Hardtman et al.	Sep 1969	A
4196207	Webber	Apr 1980	A

Number	Date	Country
A-0 323 757	Jul 1989	EP
0326328	Aug 1989	EP
A-0 447 891	Sep 1991	EP
A-0 452 002	Oct 1991	EP
A-0 519 211	Dec 1992	EP
WO 9208704	May 1992	WO

Substituted pyrimidines, processes for their preparation, and their use as pesticides and fungicides

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

US Classifications

Field of Search

US

International Classifications

Term Extension

Abstract

Description

Claims

Priority Claims (1)

Parent Case Info

US Referenced Citations (2)

Foreign Referenced Citations (6)

Non-Patent Literature Citations (9)

Entry
Grant and Hackh's Chemical Dictionary Fifth Edition (1987) p. 282, re Leters.*
Thomae, Chemical Abstracts, vol. 67: 100149 (1967).*
Cronin et al, Chemical Abstracts, vol. 70: 68419 (1969).*
Robba et al, Chemical Abstracts, vol. 75: 151829 (1971).*
Eck et al, Chemical Abstracts, vol. 81 entry 120676 (1974).*
Keir et al, Chemical Abstracts, vol. 86, entry 436 45 (1977).*
Cox et al, Chemical Abstracts, vol 87, (1977).*
Sunley et al, Chemical Abstracts, vol. 89: 124572 (1978).*
Miki et al, Chemical Abstracts, vol., 90: 87501 (1979).