TREA

Herbicidal sulphonylamino(thio)carbonyl compounds

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Information

  • Patent Grant
  • 6251831
  • Patent Number
    6,251,831
  • Date Filed
    Wednesday, December 30, 1998
    26 years ago
  • Date Issued
    Tuesday, June 26, 2001
    23 years ago
Information
Abstract
The invention relates to novel sulphonylamino(thio)carbonyl compounds of the formula (I), in whichA represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl,Q represents oxygen or sulphur,R1 represents hydrogen or formyl or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl,R2 represents cyano or halogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, andR3 represents in each case optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulphur or nitrogen and from one to three further ring members can be nitrogen,and salts of compounds of the formula (I),the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneand N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide being excluded by disclaimer;and also to processes and novel intermediates for the preparation of the novel substances and to their use as herbicides.
Description




The invention relates to novel sulphonylamino(thio)carbonyl compounds, to a number of processes and to novel intermediates for their preparation, and to their use as herbicides.




It is already known that certain sulphonylaminocarbonyl compounds, such as, for example, the compounds 4,5-dimethoxy-2-(2-methoxy-phenylsulphonylamino-carbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide possess herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). The action of these compounds, however, is not in every respect satisfactory.




The novel sulphonylamino(thio)carbonyl compounds have now been found of the ageneral formula (I),











in which




A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl,




Q represents oxygen or sulphur,




R


1


represents hydrogen or formyl or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl,




R


2


represents cyano or halogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, and




R


3


represents in each case optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulphur or nitrogen and from one to three further ring members can be nitrogen,




and salts of compounds of the formula (I),




the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide being excluded by disclaimer.




The novel sulphonylamino(thio)carbonyl compounds of the general formula (I) are obtained if




(a) aminosulphonyl compounds of the general formula (II)











in which




A, R


1


and R


2


have the meanings given above




are reacted with (thio)carboxylic acid derivatives of the general formula (III)











in which




Q and R


3


have the meanings given above and




Z represents halogen, alkoxy, aryloxy or arylalkoxy,




optionally in the presence of an acid acceptor and optionally in the presence of a diluent,




or if




(b) sulphonyl iso(thio)cyanates of the general formula (IV)











in which




A, Q, R


1


and R


2


have the meanings given above




are reacted with heterocycles of the general formula (V)






H—R


3


  (V)






in which




R


3


has the meaning given above,




optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,




or if




(c) chlorosulphonyl compounds of the general formula (VI)











in which




A, R


1


and R


2


have the meanings given above




are reacted with heterocycles of the general formula (V)






H—R


3


  (V)






in which




R


3


has the meaning given above




and metal (thio)cyanates of the general formula (VII)






MQCN  (VII)






in which




Q has the meaning given above, and




M represents an alkali metal or alkaline earth metal equivalent,




optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,




or if




(d) chlorosulphonyl compounds of the general formula (VI)











in which




A, R


1


and R


2


have the meanings given above




are reacted with (thio)carboxamides of the general formula (VIII)











in which




Q and R


3


have the meanings given above,




optionally in the presence of an acid acceptor and optionally in the presence of a diluent,




or if




(e) sulphonylamino(thio)carbonyl compounds of the general formula (IX)











in which




A, Q,R


1


and R


2


have the meanings given above, and




Z represents halogen, alkoxy, aryloxy or arylalkoxy,




are reacted with heterocycles of the general formula (V)






H—R


3


  (V)






in which




R


3


has the meaning given above,




optionally in the presence of an acid acceptor and optionally in the presence of a diluent,




or if




(f) heterocycles of the general formula (V)






H—R


3


  (V)






in which




R


3


has the meaning given above,




are reacted with chlorosulphonyl iso(thio)cyanate, optionally in the presence of a diluent, and the adducts formed in this reaction are reacted in situ with benzene derivatives of the general formula (X)











in which




A, R


1


and R


2


have the meanings given above,




optionally in the presence of an acid acceptor and optionally in the presence of a diluent,




and, if desired, the compounds of the formula (I) obtained by processes (a), (b), (c), (d), (e) or (f) are converted into salts by customary methods.




The novel sulphonylamino(thio)carbonyl compounds of the general formula (I) are distinguished by a strong herbicidal activity.




The invention relates preferably to compounds of the formula (I) in which




A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, C


1


-C


6


-alkyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkinyl or C


3


-C


6


-cycloalkyl,




Q represents oxygen or sulphur,




R


1


represents hydrogen or formyl or represents in each case optionally cyano-, fluoro-, chloro-, bromo-, phenyl- or C


1


-C


4


-alkoxy-substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C


1


-C


4


-alkyl-substituted C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkyl-carbonyl or C


3


-C


6


-cycloalkyl-sulphonyl,




R


2


represents cyano, fluoro, chloro or bromo or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C


1


-C


4


-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and




R


3


represents in each case optionally substituted heterocyclyl of the formulae below,











in which




Q


1


, Q


2


and Q


3


each represent oxygen or sulphur, and




R


4


represents hydrogen, hydroxyl, amino or cyano, or represents C


2


-C


10


-alkylideneamino, or represents optionally fluoro-, chloro-, bromo-, cyano-, C


1


-C


4


-alkoxy-, C


1


-C


4


-alkyl-carbonyl- or C


1


-C


4


-alkoxy-carbonyl-substituted C


1


-C


6


-alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C


2


-C


6


-alkenyl or C


2


-C


6


-alkinyl, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, C


1


-C


4


-alkoxy- or C


1


-C


4


-alkoxy-carbonyl-substituted C


1


-C


6


-alkoxy, C


1


-C


6


-alkylamino or C


1


-C


6


-alkyl-carbonylamino, or represents C


3


-C


6


-alkenyloxy, or represents di-(C


1


-C


4


-alkyl)-amino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C


1


-C


4


-alkyl-substituted C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkylamino or C


3


-C


6


-cycloalkyl-C


1


-C


4


-alkyl, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C


1


-C


4


-alkyl-, trifluoromethyl- and/or C


1


-C


4


-alkoxy-substituted phenyl, phenylamino or phenyl-C


1


-C


4


-alkyl,




R


5


represents hydrogen, hydroxyl, mercapto, amino, cyano, fluoro, chloro, bromo or iodo, or represents optionally fluoro-, chloro-, bromo-, cyano-, C


1


-C


4


-alkoxy-, C


1


-C


4


-alkyl-carbonyl- or C


1


-C


4


-alkoxy-carbonyl-substituted C


1


-C


6


-alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C


2


-C


6


-alkenyl or C


2


-C


6


-alkinyl, or represents in each case optionally fluoro-, chloro-, cyano-, C


1


-C


4


-alkoxy- or C


1


-C


4


-alkoxy-carbonyl-substituted C


1


-C


6


-alkoxy, C


1


-C


6


-alkylthio, C


1


-C


6


alkylamino or C


1


-C


6


-alkyl-carbonylamino, or represents C


3


-C


6


-alkenyloxy, C


3


-C


6


-alkinyloxy, C


3


-C


6


-alkenylthio, C


3


-C


6


-alkinylthio, C


3


-C


6


-alkenylamino or C


3


-C


6


-alkinylamino, or represents di-(C


1


-C


4


-alkyl)-amino, or represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C


1


-C


4


-alkyl-substituted C


3


-C


6


-cycloalkyl, C


5


-C


6


-cycloalkenyl, C


3


-C


6


-cycloalkyloxy, C


3


-C


6


-cycloalkylthio, C


3


-C


6


-cycloalkylamino C


3


-C


6


-cycloalkyl-C


1


-C


4


-alkyl, C


3


-C


6


-cycloalkyl-C


1


--C


4


-alkoxy, C


3


-C


6


-cycloalkyl-C


1


-C


4


-alkylthio or C


3


-C


6


-cycloalkyl-C


1


-C-alkylamino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C


1


-C


4


-alkyl-, trifluoromethyl-, C


1


-C


4


-alkoxy- and/or C


1


-C


4


-alkoxy-carbonyl-substituted phenyl, phenyl-C


1


-C


4


-alkyl, phenoxy, phenyl-C


1


-C


4


-alkoxy, phenylthio, phenyl-C


1


-C


4


-alkylthio, phenylamino or phenyl-C


1


-C


4


-alkylamino, or




R


4


and R


5


together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and also




R


6


, R


7


and R


8


are identical or different and represent hydrogen, cyano, fluoro, chloro or bromo, or represent in each case optionally fluoro-, chloro-, bromo- or C


1


-C


4


-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulphinyl and alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C


1


-C


4


-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,




the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl1H-pyrazole-3-carboxamide being excluded by disclaimer.




The invention also relates preferably to sodium, potassium, magnesium, calcium, ammonium, C


1


-C


4


-alkyl-ammonium, di-(C


1


-C


4


-alkyl)-ammonium, tri-(C


1


-C


4


-alkyl)-ammonium, tetra-(C


1


-C


4


-alkyl)-ammonium, tri-(C


1


-C


4


-alkyl)-sulphonium, C


5


- or C


6


-cycloalkyl-ammonium and di-(C


1


-C


2


-alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which A, Q, R


1


, R


2


and R


3


have the meanings indicated above as preferred.




The invention relates in particular to compounds of the formula (I) in which




A represents a single bond, oxygen or the group N—R, in which R represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,




Q represents oxygen or sulphur,




R


1


represents hydrogen or formyl, or represents in each case optionally fluoro-, chloro-, bromo-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, acetyl, propionyl, butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, n-, i-, s- or t-butylsulphonyl, or represents in each case optionally fluoro-, chloro- or methyl-substituted cyclopropyl, cyclopropylcarbonyl or cyclopropylsulphonyl,




R


2


represents cyano, fluoro, chloro or bromo, or represents in each case optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy, butenyloxy, propinyloxy or butinyloxy and




R


3


represents in each case optionally substituted heterocyclyl of the formulae below,











 in which




Q


1


, Q


2


and Q


3


each represent oxygen or sulphur, and




R


4


represents hydrogen, hydroxyl or amino, or represents C


3


-C


8


-alkyli-deneamino, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy or butenyloxy, or represents dimethylamino or diethylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl,. cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally fluoro-, chloro-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl,




R


5


represents hydrogen, hydroxyl, mercapto, amino, fluoro, chloro or bromo, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted ethenyl, propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethylamino or dipropylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentyImethoxy, cyclohexymethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluoro-, chloro-, methyl-, trifluoromethyl-, methoxy- and/or methoxy-carbonyl substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or




R


4


and R


5


together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and also




R


6


, R


7


and R


8


are identical or different and represent hydrogen, cyano, fluoro, chloro or bromo, or represent in each case optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propinyloxy, butinyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio, butenylthio, propinylthio, butinylthio, methylsulphinyl, ethylsulphinyt, methylsulphonyl or ethylsulphonyl, or represent cyclopropyl,




the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl1H-pyrazole-3-carboxamide being excluded by disclaimer.




A very particularly preferred group of compounds according to the invention are the compounds of the formula (I), in which




A represents a single bond,




Q represents oxygen or sulphur,




R


1


represents methyl, ethyl, n- or i-propyl,




R


2


represents chloro or methyl- in each case in position 5 or 6- and




R


3


represents optionally substituted triazolinyl of the formula below











 in which




Q


1


represents oxygen or sulphur, and




R


4


represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents propenyl or propinyl, or represents methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl, and




R


5


represents hydrogen, chloro or bromo, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally fluoro and/or chloro-substituted propenyl or propinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, or represents propenyloxy or cyclopropyl.




The radical definitions listed above, whether general or listed in ranges of preference, apply not only to the end products of the formula (I) but also, correspondingly, to the starting materials and/or intermediates required in each case of the preparation. These radical definitions can be combined as desired with one another, thus including combinations between the preferred ranges indicated.




Using, for example, 2-fluoro-6-methoxy-benzenesulphonamide and 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazole-3-thi one as starting materials, the course of reaction in the process (a) according to the invention can be illustrated by the following equation:











Using, for example, 2-ethoxy-6-methyl-phenylsulphonyl-isothiocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of reaction in the process (b) according to the invention can be illustrated by the following equation:











Using, for example, 2-rnethoxy-3-methyl-b enzenesulphochloride, 5-ethylthio-4-rnethoxy-2,4-dihydro-3H-1,2,4 -triazol-3-one and potassium cyanate as starting materials, the course of reaction in the process (c) according to the invention can be illustrated by the following equation:











Using, for example, 2-ethoxy-4-fluoro-benzenesulphochloride and 5-methyl-1,2,4-oxadiazole-3-carboxamide as starting materials, the course of reaction in the process (d) according to the invention can be illustrated by the following equation:











Using, for example, N-(2-chloro-6-propoxy-phenylsulphonyl)-O-methyl-urethane and 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of reaction in the process (e) according to the invention can be illustrated by the following equation:











Using, for example, 5-chloro-4-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one and chlorosulphonylisocyanate and then 2-ethoxy-6-methyl-aniline as starting materials, the course of reaction in the process (f) according to the invention can be illustrated by the following equation:











A general definition of the aminosulphonyl compounds to be used as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) is given by the formula (II). In the formula (II) A, R


1


and R


2


preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or, respectively, particularly preferable for A, R


1


and R


2


.




The starting materials of the formula (II) are known and/or can be prepared by methods known per se (cf. EP 216504, DE 3208189, EP 44807, EP 23422).




Compounds not yet known from the literature, and which as novel substances are likewise a subject of the present application, are the sulphonamides of the general formula (IIa),











in which




A


1


represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethyl, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and




A


2


represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.




The novel sulphonamides of the formula (IIa) are obtained if sulphonyl chlorides of the formula (VIa)











in which




A


1


and A


2


have the meanings given above




are reacted with ammonia, optionally in the presence of a diluent, for example water, at temperatures between 0° C. and 50° C. (cf. the Preparation Examples).




The starting materials of the formula (II) can in general be obtained also by reacting phenol derivatives of the formula (IIb)











in which




A and R


2


have the meanings given above




with alkylating agents of the formula (XI)






X—R


1


  (XI)






in which




R


1


has the meaning given above, and




X represents halogen or the group R


1


—O—SO


2


—O—,




optionally in the presence of an acid acceptor, for example potassium carbonate, and optionally in the presence of a diluent, for example toluene, at temperatures between 10° C. and 150° C. (cf. the Preparation Examples).




The phenol derivatives of the formula (IIb) required as precursors are known and/or can be prepared by methods known per se (cf. EP 44807, Metalloberflache [Metal surface]—Angew. Elektrochemie 27 (1973), 217-227—cited in Chem. Abstracts 79:86733; Preparation Examples).




The alkylating agents of the formula (XI) which are also required as precursors are known synthesis chemicals.




A general definition of the (thio)carboxylic acid derivatives also to be used as starting materials in the process (a) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (III). In the formula (III), Q and R


3


preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or, respectively, particularly preferable for Q and R


3


; Z preferably represents fluorine, chlorine, bromine, C


1


-C


4


-alkoxy, phenoxy or benzyloxy, and in particular represents chlorine, methoxy, ethoxy or phenoxy.




The starting materials of the formula (III) are known and/or can be prepared by methods known per se (cf. EP 459244, EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).




A general definition of the sulphonyl iso(thio)cyanate to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I) is given with the formula (IV). In the formula (IV), A, Q, R


1


and R


2


preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, Q, R


1


and R


2


.




The starting materials of the formula (IV) are known and/or can be prepared by methods known per se (cf. EP 23422, EP 216504).




Compounds not yet known from the literature, and which as novel substances are likewise a subject of the present application, are the sulphonyl iso(thio)cyanates of the general formula (IVa)











in which




Q represents oxygen or sulphur,




A


1


represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethyl, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and




A


2


represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.




The novel sulphonyl iso(thio)cyanates of the formula (IVa) are obtained if sulphonamides of the formula (IIa)—above—are reacted with phosgene or, respectively, thiophosgene, optionally in the presence of an alkyl isocyanate, for example butyl isocyanate, optionally in the presence of a reaction auxiliary, for example diazabicyclo[2.2.2]octane, and in the presence of a diluent, for example toluene, xylene or chlorobenzene, at temperatures between 80° C. and 150° C., and, after the end of the reaction, the volatile components are distilled off under reduced pressure.




A general definition of the heterocycles also to be used as starting materials in the processes (b), (c), (e) and (f) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (V). In the formula (V), R


3


preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for R


3


.




The starting materials of the formula (V) are known and/or can be prepared by methods known per se (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).




A general definition of the chlorosulphonyl compounds to be used as starting materials in the processes (c) and (d) according to the invention for the preparation of compounds of the formula (I) is given by the formula (VI). In the formula (VI), A, R


1


and R


2


preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, R


1


and R


2


.




The starting materials of the formula (VI) are known and/or can be prepared by methods known per se (cf. EP 511826, DE 3208189, EP23422).




Compounds not yet known from the literature, which as novel substances are likewise a subject of the present application, are the sulphonyl chlorides of the formula (VIa)











in which




A


1


represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethyl, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and




A


2


represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.




The novel sulphonyl chlorides of the formula (VIa) are obtained if aniline derivatives of the formula (XII)











in which




A


1


and A


2


have the meanings given above




dare reacted with an alkali metal nitrite, for example sodium nitrite, in the presence if hydrochloric acid at temperatures between −10° C. and +10° C., and the diazonium salt solution thus obtained is reacted with sulphur dioxide in the presence of a diluent, for example dichioromethane or 1,2-dichioro-ethane, and in the presence of a catalyst, for example copper(I) chloride, optionally in the presence of a further catalyst, for example dodecyltrimethylammonium bromide, at temperatures between −10° C. and +50° C. (cf. the Preparation Examples).




The aniline derivatives of the formula (XII) required as precursors are known and/or can be prepared by methods known per se (cf. EP 511826, US 4992091, EP 185128, DE 2405479, Preparation Examples).




The abovementioned novel benzenesulphonic acid derivatives of the formulae (IIa), (IVa) and (VIa) can be defined comprehensively by the following formula (XlII):











in which




E represents —NH


2


, —N═C+Q or —Cl, where




Q represents O or S, and also




A


1


represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethy, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and




A


2


represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.




A general definition of the (thio)carboxamides to be used as starting materials in the process (d) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (VIII). In the formula (VIII), Q and R


3


preferably or in particular have that meaning which has already been indicated above, in connection with a description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for Q and R


3


.




The starting materials of the formula (VIII) are known and/or can be prepared by methods known per se (cf. EP 459244).




A general definition of the sulphonylamino(thio)carbonyl compounds to be used as starting materials in the process (e) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (IX). In the formula (IX), A, Q, R


1


and R


2


preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, Q, R


1


and R


2


; Z preferably represents fluoro, chloro, bromo, C


1


-C


4


-alkoxy, phenoxy or benzyloxy, and in particular represents chlorine, methoxy, ethoxy or phenoxy.




A general definition of the benzene derivatives to be used as starting materials in the process (f) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (X). In the formula (X), A, R


1


and R


2


preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, R


1


and R


2


.




Starting materials of the formula (X) are known and/or can be prepared by methods known per se (cf. EP 511826, U.S. Pat. No. 4,992,091, EP 185128, DE 2405479, Preparation Examples).




The processes (a), (b), (c), (d), (e) and (f) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents in this context are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxanes; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; esters such as methyl acetate and ethyl acetate; nitrites, for example acetonitrile and propionitrile; amides, for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.




As reaction auxiliaries and/or as acid acceptors in the processes (a), (b), (c), (d), (e) and (f) according to the invention it is possible to employ all acid-binding agents which can customarily be used for such reactions. Preferred among suitable examples are alkali metal hydroxides, for example sodium. hydroxide and potassium hydroxide, alkaline earth metal hydroxides, for example calcium hydroxide, alkali metal carbonates and alcoholates, such as sodium carbonate and potassium carbonate, sodium tert-butylate and potassium tert-butylate, and also basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2.2.2]-octane (DABCO).




The reaction temperatures in the processes (a), (b), (c), (d), (e) and (f) according to the invention can be varied within a relatively wide range. They are in general carried out at temperatures of between −20° C. and +150° C., preferably at temperatures between 0° C. and +100° C.




The processes (a), (b), (c), (d), (e) and (f) according to the invention are generally carried out under atmospheric pressure. However it is also possible to operate under increased or reduced pressure.




For carrying out processes (a), (b), (c), (d), (e). and (f) according to the invention, the starting materials required in each case are in general employed in approximately equimolar quantities. However, it is also possible to use one of the components employed in each case in a relatively large excess. The reactions are in general carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a number of hours at the particular temperature required. Working up in the case of the processes (a), (b), (c), (d), (e) and (f) according to the invention is in each case by customary methods (cf. the Preparation Examples).




Salts of the compounds of the general formula (I) according to the invention can be prepared if desired. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in an appropriate solvent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding an appropriate base. The salts can then—if desired after prolonged stirring—be isolated by concentration or filtration with suction.




The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.




The active compounds according to the invention can be used, for example, in connection with the following plants:




Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver Centaurea, Trifolium, Ranunculus and Taraxacum.




Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.




Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.




Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.




However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.




The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pasture-land, and for the selective combating of weeds in annual cultures.




The compounds of the formula (I) according to the invention are preferably suitable for combating monoctyledon and dicotyledon broad-leaved weeds, both pre-emergence and post-emergence. They exhibit strong herbicidal activity and a broad spectrum action when used on the soil and on above-ground parts of the plants.




The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.




These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.




In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.




As solid carriers there are suitable:




for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.




Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.




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




The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.




For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.




Possible components for the mixtures are known herbicides, for example anilides, for example diflufenican and propanil; arylcarboxylic acids, for example dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, for example 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, for example diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones, for example chloridazon and norflurazon; carbamates, for example chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides, for example alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines, for example oryzalin, pendimethalin and trifluralin; diphenyl ethers, for example acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas, for example chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines, for example alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, for example imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, for example bromoxynil, dichlobenil and ioxynil; oxyacetamides, for example mefenacet; sulphonyl-ureas, for example amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates, for example butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, for example atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine; triazinones, for example hexazinone, metamitron and metribuzin; others, for example aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.




Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, are also possible.




The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.




The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.




The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.











The preparation and use of the active compounds according to the invention can be seen from the following examples.




PREPARATION EXAMPLES




Example 1
















(Process (a))




A mixture of 2.5 g (10 mmol) of 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2.3 g (10 mmol) of 2-isopropoxy-6-methyl-benzenesulphonamide, 1.5 g (10 mmol) of diazabicyclo[5.4.0]undec-7-ene (DBU) and 50 ml of acetonitrile is stirred at 20° C. for 5 hours. It is then concentrated under a water pump vacuum and the residue is stirred with 50 ml of 1N hydrochloric acid, the mixture is filtered with suction, the filter product is stirred with diethyl ether and the mixture is again filtered with suction.




2.4 g (60% of theory) of 5-ethoxy-4-methyl-2-(2-isopropoxy-6-methyl-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 155° C.




Example 2
















(Process (c))




A mixture of 1.7 g (10 mmol) of


4


-methyl-5-propargylthio-2,4-dihydro-3H-1,2,4-triazol-3-one, 1.3 g (20 mmol) of sodium cyanate, 2.5 g (10 mmol) of 2-methyl-6-n-propoxy-benzenesulphochloride and 50 ml of acetonitrile is heated under reflux for 3 hours. It is then concentrated under a water pump vacuum, the residue is stirred with 1N hydrochloric acid and the mixture is subjected three times to extraction with 50 ml of methylene chloride each time. The combined organic extraction solutions are concentrated, the residue is digested with isopropanol and the crystalline product is isolated by filtration with suction.




2.2 g (52% of theory) of 4-methyl-5-propargylthio-2-(2-methyl-6-n-propoxy-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 151° C.




Example 3
















(Process (d))




A mixture of 3.2 g (25 mmol) of 5-methyl-1,2,4-oxadiazole-3-carboxamide, 4.2 g (75 mmol) of potassium hydroxide (powder) and 200 ml of dioxane is stirred at 60° C. for 30 minutes. It is then concentrated to about half its volume under a water pump vacuum, and a solution of 7 g (30 mmol) of 2-ethoxy-6-methyl-benzenesulphochloride in 10 ml of dioxane is added dropwise at about 20° C. The reaction mixture is then stirred at 20° C. for about 15 hours more. It is then concentrated under a water pump vacuum, the residue is stirred with 50 ml of 1N hydrochloric acid and the crystalline product is isolated by filtration with suction. 4.0 g (49% of theory) of N-(2-ethoxy-6-methyl-phenylsulphonyl)-5-methyl-1,2,4-oxadiazole-3-carboxamide are obtained of melting point 168° C.




Example 4
















(Process (f))




1.7 g (12 mmol) of chlorosulphonyl isocyanate are added to a solution, cooled to 5° C., of 1.4 g (10 mmol) of 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 50 ml of methylene chloride, and then a solution of 1.5 g (10 mmol) of 2-ethoxy-6-methyl-aniline and 1.0 g (10 mmol) of triethylamine in 10 ml of methylene chloride is added dropwise, likewise at 5° C. The reaction mixture is then stirred at about 20° C. For 15 hours. Subsequently, 100 ml of 1N hydrochloric acid are added. After a thorough stirring, the organic phase is separated off, dried over sodium sulphate and filtered. The filtrate is concentrated under water pump vacuum, the residue is digested with isopropanol and the crystalline product is isolated by filtration with suction.




1.8 g (45% of theory) of 5-ethoxy-4-methyl-2-(2-ethoxy-6-methyl-phenyl-aminosulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 147° C.




In analogy to Example 1 to 4 and in accordance with the general description of the preparation processes according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below (showing Examples Nos. 5-965), as well as the compounds of the formula (IA) listed in Table IA thereafter (showing Examples Nos. 966-1637):












TABLE 1











Examples of the compounds of the formula (I)













(I)












































Melting






Ex.







(position-)





point






No.




A




Q




R


1






R


2






R


3






(° C.)









 5




—




O




n-C


3


H


7






(6-)CH


3


















117













 6




—




O




C


2


H


5






(6-)Cl
















156













 7




—




O




C


2


H


5






(6-)CH


3


















110













 8




—




O




C


2


H


5






(6-)CH


3


















141













 9




—




O




C


2


H


5






(6-)CH


3


















162













 10




—




O




n-C


3


H


7






(6-)CH


3


















126













 11




—




O




n-C


3


H


7






(6-)CH


3


















150













 12




—




O




n-C


3


H


7






(6-)CH


3


















129













 13




—




O




CH


3






(6-)CH


3


















153













 14




—




O




CH


3






(6-)CH


3


















167













 15




—




O




CH


3






(6-)CH


3


















167













 16




—




O




i-C


3


H


7






(6-)CH


3


















125













 17




—




O




i-C


3


H


7






(6-)CH


3


















131













 18




—




O




C


2


H


5






(5-)CH


3


















222













 19




—




O




C


2


H


5






(5-)CH


3


















139













 20




—




O




C


2


H


5






(4-)CH


3


















189













 21




—




O




C


2


H


5






(5-)CH


3


















131













 22




—




O




—C


2


H


4


OC


2


H


5






(6-)CH


3


















118













 23




—




O




—CH


2


CH


2


Cl




(6-)CH


3


















137













 24




—




O




—CH


2


CH


2


Cl




(6-)CH


3


















149













 25




—




O




i-C


3


H


7






(5-)CH


3


















125













 26




—




O




i-C


3


H


7






(5-)CH


3


















140













 27




—




O




n-C


3


H


7






(5-)CH


3


















119













 28




—




O




n-C


3


H


7






(5-)CH


3


















134













 29




—




O




n-C


3


H


7






(5-)CH


3


















110













 30




—




O




C


2


H


5






(6-)CH


3


















108













 31




—




O




C


2


H


5






(6-)CH


3


















173













 32




—




O




C


2


H


5






(6-)CH


3


















119













 33




—




O




C


2


H


5






(6-)CH


3


















121













 34




—




O




C


2


H


5






(6-)CH


3


















109













 35




—




O




C


2


H


5






(6-)CH


3


















111













 36




—




O




n-C


3


H


7






(6-)CH


3


















 91













 37




—




O




n-C


3


H


7






(6-)CH


3


















130













 38




—




O




n-C


3


H


7






(6-)CH


3


















126













 39




—




O




n-C


3


H


7






(6-)CH


3


















101













 40




—




O




n-C


3


H


7






(6-)CH


3


















152













 41




—




O




n-C


3


H


7






(6-)CH


3


















100













 42




—




O




n-C


3


H


7






(6-)CH


3


















120













 43




—




O




n-C


3


H


7






(6-)CH


3


















117













 44




—




O




n-C


3


H


7






(6-)CH


3


















126













 45




—




O




n-C


3


H


7






(6-)CH


3


















113













 46




—




O




i-C


3


H


7






(6-)CH


3


















130













 47




—




O




i-C


3


H


7






(6-)CH


3


















139













 48




—




O




i-C


3


H


7






(6-)CH


3


















121













 49




—




O




i-C


3


H


7






(6-)CH


3


















119













 50




—




O




i-C


3


H


7






(6-)CH


3


















128













 51




—




O




i-C


3


H


7






(6-)CH


3


















134













 52




—




O




i-C


3


H


7






(6-)CH


3


















130













 53




—




O




i-C


3


H


7






(6-)CH


3


















117













 54




—




O




i-C


3


H


7






(6-)CH


3


















134













 55




—




O




i-C


3


H


7






(6-)CH


3


















141













 56




—




O




i-C


3


H


7






(6-)CH


3


















132













 57




—




O




i-C


3


H


7






(6-)CH


3


















166













 58




—




O




i-C


3


H


7






(6-)CH


3


















118













 59




—




O




i-C


3


H


7






(6-)CH


3


















150













 60




—




O




i-C


3


H


7






(6-)CH


3


















144













 61




—




O




i-C


3


H


7






(6-)CH


3


















170













 62




—




O




i-C


3


H


7






(6-)CH


3


















120













 63




—




O




n-C


3


H


7






(6-)CH


3


















124













 64




—




O




n-C


3


H


7






(6-)CH


3


















125













 65




—




O




n-C


3


H


7






(6-)CH


3


















116













 66




—




O




n-C


3


H


7






(6-)CH


3


















152













 67




—




O




n-C


3


H


7






(6-)CH


3


















143













 68




—




O




C


2


H


5






(6-)CH


3


















160













 69




—




O




C


2


H


5






(6-)CH


3


















133













 70




—




O




C


2


H


5






(6-)CH


3


















 97













 71




—




O




C


2


H


5






(6-)CH


3


















 96













 72




—




O




C


2


H


5






(6-)CH


3


















156













 73




—




O




C


2


H


5






(6-)CH


3


















145













 74




—




O




C


2


H


5






(6-)CH


3


















120













 75




—




O




C


2


H


5






(6-)CH


3


















125













 76




—




O




C


2


H


5






(6-)CH


3


















140













 77




—




O




H




(6-)CH


3


















 88













 78




—




O




C


2


H


5






(5-)CH


3


















130













 79




—




O




n-C


3


H


7






(6-)CH


3


















141













 80




—




O




n-C


3


H


7






(6-)CH


3


















 98













 81




—




O




n-C


3


H


7






(6-)CH


3


















141













 82




—




O




n-C


3


H


7






(6-)CH


3


















101













 83




—




O




n-C


3


H


7






(6-)CH


3


















136













 84




—




O




n-C


3


H


7






(6-)CH


3


















 96













 85




—




O




n-C


3


H


7






(6-)CH


3


















 90













 86




—




O




n-C


3


H


7






(6-)CH


3


















136













 87




—




O




C


2


H


5






(6-)CH


3


















122













 88




—




O




C


2


H


5






(6-)CH


3


















154













 89




—




O




i-C


3


H


7






(6-)CH


3


















139













 90




—




O




C


2


H


5






(6-)CH


3


















142













 91




—




O




C


2


H


5






(6-)CH


3


















153













 92




—




O




C


2


H


5






(6-)CH


3


















145













 93




—




O




C


2


H


5






(6-)CH


3


















132













 94




—




O




C


2


H


5






(6-)CH


3


















141













 95




—




O




C


2


H


5






(6-)CH


3


















130













 96




—




O




CH


3






(5-)CH


3


















156













 97




—




O




CH


3






(5-)CH


3


















177













 98




—




O




CH


3






(4-)CH


3


















115













 99




—




O




CH


3






(4-)CH


3


















166













100




—




O




CH


3






(3-)CH


3


















162













101




—




O




CH


3






(3-)CH


3


















143













102




—




O




CH


3






(3-)CH


3


















165













103




—




O




CHF


2






(5-)CH


3


















176













104




—




O




CHF


2






(5-)CH


3


















119













105




—




O




CHF


2






(5-)CH


3


















126













106




—




O




CHF


2






(5-)CH


3


















151













107




—




O




CHF


2






(5-)CH


3


















188













108




—




O




CHF


2






(5-)CH


3


















137













109




—




O




CHF


2






(5-)CH


3


















117













110




—




O




CHF


2






(5-)CH


3


















155













111




—




O




CHF


2






(4-)CH


3


















152













112




—




O




CHF


2






(4-)CH


3


















176













113




—




O




CHF


2






(4-)CH


3


















108













114




—




O




CHF


2






(6-)CH


3


















163













115




—




O




CHF


2






(6-)CH


3


















136













116




—




O




CHF


2






(6-)CH


3


















118













117




—




O




CHF


2






(6-)CH


3


















104













118




—




O




CHF


2






(5-)CH


3


















 98













119




—




O




CHF


2






(6-)CH


3


















128













120




—




O




CHF


2






(6-)CH


3


















165













121




—




O




CHF


2






(6-)CH


3


















155













122




—




O




CHF


2






(6-)CH


3


















105













123




—




O




CHF


2






(6-)CH


3


















 81













124




—




O




CHF


2






(6-)CH


3


















174













125




—




O




CHF


2






(5-)CH


3


















150













126




—




O




CHF


2






(6-)CH


3


















124













127




—




O




CHF


2






(6-)CH


3


















200













128




—




S




n-C


3


H


7






(6-)CH


3


















160













129




—




S




n-C


3


H


7






(6-)CH


3


















148













130




—




S




C


2


H


5






(6-)CH


3


















141













131




—




S




C


2


H


5






(6-)CH


3


















125













132




—




S




C


2


H


5






(6-)CH


3


















158













133




—




S




i-C


3


H


7






(6-)CH


3


















155













134




—




S




n-C


3


H


7






(6-)CH


3


















153













135




—




S




n-C


3


H


7






(6-)CH


3


















131













136




—




S




n-C


3


H


7






(6-)CH


3


















120













137




—




O




C


2


H


5






(6-)Cl
















149













138




—




O




C


2H




5






(6-)Cl
















 99













139




—




O




CH


3






(6-)Cl
















176













140




—




O




CH


3






(6-)Cl
















192













141




—




O




C


2


H


5






(6-)Cl
















144













142




—




O




CH


3






(6-)Cl
















114













143




—




O




C


2


H


5






(6-)Cl
















144













144




—




O




CH


3






(6-)Cl
















157













145




—




O




C


2


H


5






(6-)Cl
















142













146




—




O




CH


3






(6-)Cl
















191













147




—




O




C


2


H


5






(6-)Cl
















116













148




—




O




CH


3






(6-)Cl
















205













149




—




O




CH


3






(6-)Cl
















147













150




—




O




C


2


H


5






(6-)Cl
















117













151




—




O




CH


3






(6-)Cl
















149













152




—




O




CH


3






(6-)Cl
















176













153




—




O




CH


3






(6-)Cl
















150













154




—




O




CH


3






(6-)Cl
















146













155




—




O




CH


3






(6-)Cl
















191













156




—




O




CH


3






(6-)Cl
















127













157




—




O




CH


3






(6-)Cl
















174













158




—




O




n-C


3


H


7






(6-)Cl
















117













159




—




O




n-C


3


H


7






(6-)Cl
















134













160




—




O




n-C


3


H


7






(6-)Cl
















115













161




—




O




n-C


3


H


7






(6-)Cl
















137













162




—




O




n-C


3


H


7






(6-)Cl
















125













163




—




O




n-C


3


H


7






(6-)Cl
















119













164




—




O




H




(6-)Cl
















147













165




—




O




n-C


3


H


7






(6-)Cl
















148













166




—




O




i-C


3


H


7






(6-)Cl
















143













167




—




O




i-C


3


H


7






(6-)Cl
















122













168




—




O




CH


3






(6-)Cl
















165













169




—




O




n-C


3


H


7






(5-)Cl
















154













170




—




O




n-C


3


H


7






(5-)Cl
















136













171




—




O




n-C


3


H


7






(5-)Cl
















128













172




—




O




CH


3






(6-)Cl
















143













173




—




O




i-C


3


H


7






(6-)Cl
















136













174




—




O




i-C


3


H


7






(6-)Cl
















121













175




—




O




i-C


3


H


7






(6-)Cl
















158













176




—




O




i-C


3


H


7






(6-)Cl
















141













177




—




O




i-C


3


H


7






(6-)Cl
















127













178




—




O




i-C


3


H


7






(6-)Cl
















143













179




—




O




i-C


3


H


7






(6-)Cl
















129













180




—




O




i-C


3


H


7






(6-)Cl
















 95













181




—




O




n-C


3


H


7






(6-)CH


3


















 74













182




—




O




n-C


3


H


7






(6-)CH


3


















114













183




—




O




n-C


3


H


7






(6-)CH


3


















140













184




—




O




n-C


3


H


7






(6-)CH


3


















159













185




—




O




n-C


3


H


7






(6-)CH


3


















107













186




—




O




n-C


3


H


7






(6-)CH


3


















132













187




—




O




n-C


3


H


7






(6-)CH


3


















132













188




—




O




n-C


3


H


7






(6-)CH


3


















110













189




—




O




CH


3






(6-)CH


3


















159













190




—




O




n-C


3


H


7






(6-)CH


3


















138













191




—




O




n-C


3


H


7






(6-)CH


3


















147













192




—




O




n-C


3


H


7






(6-)CH


3


















114













193




—




O




n-C


3


H


7






(6-)CH


3


















125













194




—




O




n-C


3


H


7






(6-)CH


3


















126













195




—




O




n-C


3


H


7






(6-)CH


3


















151













196




—




O




n-C


3


H


7






(6-)CH


3


















121













197




—




O




n-C


3


H


7






(6-)CH


3


















147













198




NH




O




C


2


H


5






(6-)CH


3


















135













199




—




O




i-C


3


H


7






(6-)CH


3


















263 (Sodium salt)













200




—




O




C


2


H


5






(6-)CH


3


















119













201




—




O




C


2


H


5






(6-)CH


3


















146













202




—




O




C


2


H


5






(6-)CH


3


















128













203




—




O




C


2


H


5






(6-)CH


3


















186













204




—




O




C


2


H


5






(6-)CH


3


















239













205




—




O




C


2


H


5






(6-)CH


3


















152













206




—




O




C


2


H


5






(6-)CH


3


















155













207




—




O




C


2


H


5






(6-)CH


3


















145 (Na salt)













208




—




O




i-C


3


H


7






(6-)CH


3


















209 (Na salt)













209




—




O




C


2


H


5






(6-)CH


3


















147 (Na salt)













210




—




O




C


2


H


5






(6-)CH


3


















140













211




—




O




C


2


H


5






(6-)CH


3


















118













212




—




O




C


2


H


5






(6-)CH


3


















156













213




—




O




C


2


H


5






(6-)CH


3


















110













214




—




O




C


2


H


5






(6-)CH


3


















133













215




—




O




i-C


3


H


7






(6-)CH


3


















138













216




—




O




i-C


3


H


7






(6-)CH


3


















154













217




—




O




i-C


3


H


7






(6-)CH


3


















149













218




—




O




i-C


3


H


7






(6-)CH


3


















112













219




—




O




i-C


3


H


7






(6-)CH


3


















162













220




—




O




i-C


3


H


7






(6-)CH


3


















 99













221




—




O




i-C


3


H


7






(6-)CH


3


















146













222




—




O




C


2


H


5






(6-)CH


3


















134













223




—




O




CH


3






(6-)CH


3


















199













224




—




O




CH


3






(6-)CH


3


















176













225




—




O




CH


3






(6-)CH


3


















145













226




—




O




i-C


3


H


7






(6-)CH


3


















133













227




NH




O




n-C


3


H


7






(5-)CH


3


















127













228




—




O




i-C


3


H


7






(6-)CH


3


















144













229




—




O




i-C


3


H


7






(6-)CH


3


















141













230




—




O




i-C


3


H


7






(6-)CH


3


















152













231




—




O




i-C


3


H


7






(6-)CH


3


















132













232




—




O




i-C


3


H


7






(6-)CH


3


















147













233




—




O




i-C


3


H


7






(6-)CH


3


















163













234




—




O




i-C


3


H


7






(6-)CH


3


















102













235




—




O




C


2


H


5






(6-)CH


3


















121













236




—




O




C


2


H


5






(6-)CH


3


















113













237




—




O




C


2


H


5






(6-)CH


3


















145













238




—




O




C


2


H


5






(6-)CH


3


















137













239




—




O




C


2


H


5






(6-)CH


3


















172













240




—




O




C


2


H


5






(6-)CH


3


















148













241




—




O




C


2


H


5






(6-)CH


3


















157













242




—




O




C


2


H


5






(6-)CH


3


















186













243




NH




O




CH


3






(6-)OCH


3


















170













244




—




O




CHF


2






(5-)CH


3



























245




—




S




i-C


3


H


7






(6-)CH


3


















160













246




—




O




CH


3






(6-)CF


3


















205













247




—




S




CH


3






(6-)CF


3


















 92













248




—




S




CH


3






(6-)CF


3


















154













249




—




S




CH


3






(6-)CF


3


















157













250




—




O




C


2


H


5






(6-)CF


3


















176













251




—




O




n-C


3


H


7


-n




(6-)CF


3


















166













252




—




O




i-C


3


H


7






(6-)CF


3


















190













253




—




O




CH


3






(6-)CF


3


















203













254




—




O




CH


3






(6-)CF


3


















156













255




—




O




CH


3






(6-)CF


3


















170













256




—




O




CH


3






(6-)CF


3


















198













257




—




O




CH


3






(6-)CF


3


















213













258




—




O




CH


3






(6-)CF


3


















152













259




—




O




CH


3






(6-)CF


3


















187













260




—




O




CH


3






(6-)CF


3


















210













261




—




O




CH


3






(6-)CF


3


















172













262




—




O




CH


3






(6-)CF


3


















145













263




—




O




CH


3






(6-)CF


3


















136













264




—




O




CH


3






(6-)CF


3


















153













265




—




O




CH


3






(6-)CF


3


















136













266




—




O




CH


3






(6-)CF


3


















210













267




—




O




CH


3






(6-)CF


3


















147













268




—




O




CH


3






(6-)CF


3


















169













269




—




O




CH


3






(6-)CF


3


















215













270




—




O




CH


3






(6-)CF


3


















138













271




—




O




CH


3






(6-)CF


3


















182













272




—




S




C


2


H


5






(6-)CF


3


















112













273




—




S




C


2


H


5






(6-)CF


3


















167













274




—




S




C


2


H


5






(6-)CF


3


















152













275




—




S




n-C


3


H


7






(6-)CF


3


















119













276




—




S




n-C


3


H


7






(6-)CF


3


















157













277




—




S




n-C


3


H


7






(6-)CF


3


















154













278




—




S




i-C


3


H


7






(6-)CF


3


















137













279




—




S




i-C


3


H


7






(6-)CF


3


















167













280




—




S




i-C


3


H


7






(6-)CF


3


















137













281




—




O




C


2


H


5






(6-)CF


3


















154













282




—




O




C


2


H


5






(6-)CF


3


















160













283




—




O




C


2


H


5






(6-)CF


3


















139













284




—




O




C


2


H


5






(6-)CF


3


















134













285




—




O




C


2


H


5






(6-)CF


3


















142













286




—




O




C


2


H


5






(6-)CF


3


















120













287




—




O




n-C


3


H


7






(6-)CF


3


















130













288




—




O




n-C


3


H


7






(6-)CF


3


















127













289




—




O




n-C


3


H


7






(6-)CF


3


















116













290




—




O




n-C


3


H


7






(6-)CF


3


















126













291




—




O




n-C


3


H


7






(6-)CF


3


















113













292




—




O




i-C


3


H


7






(6-)CF


3


















151













293




—




O




i-C


3


H


7






(6-)CF


3


















157













294




—




O




i-C


3


H


7






(6-)CF


3


















171













295




—




O




i-C


3


H


7






(6-)CF


3


















137













296




—




O




i-C


3


H


7






(6-)CF


3


















125













297




—




O




n-C


3


H


7






(6-)CF


3


















109













298




—




O




n-C


3


H


7






(6-)CF


3


















138













299




—




O




i-C


3


H


7






(6-)CF


3


















130













300




—




O




C


2


H


5






(6-)CF


3


















165













301




—




O




i-C


3


H


7






(6-)CF


3


















148













302




—




O




i-C


3


H


7






(6-)CF


3


















147













303




—




O




i-C


3


H


7






(6-)CF


3


















172













304




—




O




i-C


3


H


7






(6-)CF


3


















147













305




—




O




i-C


3


H


7






(6-)CF


3


















136













306




—




O




C


2


H


5






(6-)CF


3


















124













307




—




O




C


2


H


5






(6-)CF


3


















 98













308




—




O




C


2


H


5






(6-)CF


3


















125













309




—




O




C


2


H


5






(6-)CF


3


















179













310




—




O




C


2


H


5






(6-)CF


3


















153













311




—




O




C


2


H


5






(6-)CF


3


















171













312




—




O




n-C


3


H


7






(6-)CF


3


















113













313




—




O




n-C


3


H


7






(6-)CF


3


















138













314




—




O




n-C


3


H


7






(6-)CF


3


















110













315




—




O




n-C


3


H


7






(6-)CF


3


















134













316




—




O




i-C


3


H


7






(6-)CF


3


















167













317




—




O




i-C


3


H


7






(6-)CF


3


















120













318




—




O




i-C


3


H


7






(6-)CF


3


















117













319




—




O




i-C


3


H


7






(6-)CF


3


















160













320




—




O




i-C


3


H


7






(6-)CF


3


















154













321




—




O




i-C


3


H


7






(6-)CF


3


















159













322




—




O




n-C


3


H


7






(6-)CF


3


















141













323




—




O




i-C


3


H


7






(6-)CF


3


















146













324




—




O




i-C


3


H


7






(6-)CF


3


















134













325




—




O




i-C


3


H


7






(6-)CF


3


















168













326




—




O




CH


3






(6-)C


3


H


7


-n
















158













327




—




O




CH


3






(6-)C


3


H


7


-n
















172













328




—




O




CH


3






(6-)C


3


H


7


-n
















147













329




—




O




C


2


H


5






(6-)CF


3


















 66













330




—




O




C


2


H


5






(6-)CH


3


















134













331




—




O




C


2


H


5






(6-)CH


3


















149













332




—




O




n-C


3


H


7






(6-)CH


3


















114













333




—




O




H




(6-)Cl
















102













334




—




O




H




(6-)Cl
















143













335




—




O
















(6-)Cl
















130













336




—




O




—CH


2


C


6


H


5






(6-)Cl
















143













337




—




O




—CH


2


C


6


H


5






(6-)Cl
















 99













338




—




O




—CH


2


C≡CH




(6-)Cl
















161













339




—




O




n-C


3


H


7






(6-)CH


3


















133













340




—




O




H




(6-)CH


3


















100













341




—




O




H




(6-)CH


3


















147













342




—




O




—CH


2


C


6


H


5






(6-)CH


3


















157













343




—




O
















(6-)CH


3


















150













344




—




O




—CH


2


C≡CH




(6-)CH


3


















172













345




—




O




i-C


3


H


7






(6-)CH


3


















263 (Na salt)













346




—




O




C


2


H


5






(6-)CH


3


















136













347




—




O




i-C


3


H


7






(6-)CH


3


















113













348




—




O




i-C


3


H


7






(6-)CH


3


















175













349




—




O




i-C


3


H


7






(6-)CH


3


















135













350




—




O




i-C


3


H


7






(6-)CH


3


















 78













351




—




O




i-C


3


H


7






(6-)CH


3


















125













352




—




O




i-C


3


H


7






(6-)CH


3


















140













353




—




O




CH


3






(6-)CH


3


















161













354




—




O




CH


3






(6-)CH


3


















142













355




—




O




CH


3






(6-)CH


3


















124













356




—




O




CH


3






(6-)CH


3


















153













357




—




O




CH


3






(6-)CH


3


















170













358




—




O




CH


3






(6-)CH


3


















116













359




—




O




CH


3






(6-)CH


3


















120













360




—




O




CH


3






(5-)Cl
















172













361




—




O




CH


3






(5-)Cl
















175













362




—




O




CH


3






(5-)Cl
















192













363




—




O




CH


3






(5-)Cl
















195













364




—




O




CH


3






(5-)Cl
















174













365




—




O




CH


3






(5-)Cl
















160













366




—




O




CH


3






(5-)Cl
















214













367




—




O




CH


3






(5-)Cl
















185













368




—




O




CH


3






(5-)Cl
















191













369




NH




O




CH


3






(6-)CH


3


















161













370




NH




O




i-C


3


H


7






(6-)CH


3


















132













371




NH




O




CH


3






(6-)OCH


3


















151













372




NH




O




CH


3






(6-)CH


3


















161













373




NH




O




i-C


3


H


7






(6-)CH


3


















128













374




NH




O




CH


3






(6-)CH


3


















140













375




—




S




i-C


3


H


7






(6-)CH


3


















108













376




—




O




CHF


2






(4-)CH


3


















131













377




—




O




CH


3






(6-)CF


3


















187













378




—




O




CH


3






(6-)CF


3


















154













379




—




O




CH


3






(6-)C


2


H


5


















179













380




—




O




CH


3






(6-)C


2


H


5


















178













381




—




O




CH


3






(6-)C


2


H


5


















167













382




—




O




C


2


H


5






(6-)C


2


H


5


















135













383




—




O




C


2


H


5






(6-)C


2


H


5


















146













384




—




O




C


2


H


5






(6-)C


2


H


5


















174













385




—




O




CH


3






(6-)C


2


H


5


















130













386




—




O




CH


3






(6-)C


2


H


5


















195













387




—




O




CH


3






(6-)C


2


H


5


















183













388




—




O




C


2


H


5






(6-)C


3


H


7


-n
















135













389




—




O




C


2


H


5






(6-)C


3


H


7


-n
















149













390




—




O




CH


3






(6-)C


3


H


7


-n
















193













391




—




O




CH


3






(6-)C


3


H


7


-n
















125













392




—




O




CH


3






(6-)C


3


H


7


-n
















182













393




—




O




C


2


H


5






(6-)C


3


H


7


-n
















120













394




—




O




C


2


H


5






(6-)C


3


H


7


-n
















158













395




—




O




i-C


3


H


7






(6-)CH


3


















180













396




—




O




n-C


4


H


9






(6-)CH


3


















132













397




—




O




n-C


4


H


9






(6-)CH


3


















143













398




—




O




n-C


4


H


9






(6-)CH


3


















106













399




—




O




n-C


4


H


9






(6-)CH


3


















 98













400




—




O




n-C


4


H


9






(6-)CH


3


















140













401




—




O




CH


3






(6-)CH


3


















147













402




—




O




CH


3






(6-)CH


3


















123













403




—




O




CH


3






(6-)CH


3


















185













404




—




O




CH


3






(6-)CH


3


















154













405




NH




O




i-C


3


H


7






(6-)CH


3


















150













406




—




O




C


2


H


5






(6-)C


2


H


5


















135













407




—




O




C


2


H


5






(6-)C


2


H


5


















134













408




—




O




C


2


H


5






(6-)C


2


H


5


















178













409




—




O




C


3


H


7


-i




(6-)C


2


H


5


















109













410




—




O




C


3


H


7


-i




(6-)C


2


H


5


















125













411




—




O




C


3


H


7


-i




(6-)C


2


H


5


















161













412




—




O




C


3


H


7


-i




(6-)C


2


H


5


















114













413




—




O




C


3


H


7


-i




(6-)C


2


H


5


















142













414




—




O




C


3


H


7


-i




(6-)C


2


H


5


















124













415




—




O




CH


3






(6-)C


2


H


5


















175 (Na salt)













416




—




O




C


2


H


5






(6-)C


3


H


7


-n
















126













417




—




O




C


2


H


5






(6-)C


3


H


7


-n
















121













418




—




O




CH


3






(6-)C


3


H


7


-n
















109













419




—




O




CH


3






(6-)C


3


H


7


-n
















145













420




—




O




CH


3






(6-)C


3


H


7


-n
















126













421




—




O




CH


3






(6-)C


3


H


7


-n
















130













422




—




O




CH


3






(6-)C


3


H


7


-n
















155













423




—




O




CH


3






(6-)C


3


H


7


-n
















133













424




—




O




CH


3






(6-)C


3


H


7


-n
















145













425




—




O




—SO


2


CH


3






(6-)CH


3


















 95













426




—




O




—SO


2


CH


3






(6-)CH


3


















153













427




—




O




C


4


H


9


-n




(6-)CH


3


















154













428




—




O




—CH


2


C≡CH




(6-)CH


3


















167













429




—




O




—CH


2


C≡CH




(6-)CH


3


















170













430




—




O




—CH


2


C≡CH




(6-)CH


3


















153













431




—




O




C


4


H


9


-i




(6-)CH


3


















123













432




—




O




C


4


H


9


-i




(6-)CH


3


















145













433




—




O




C


4


H


9


-i




(6-)CH


3


















143













434




—




O




C


3


H


7


-i




(6-)CH


3


















138













435




—




O




C


3


H


7


-i




(6-)CH


3


















161













436




—




O




C


3


H


7


-i




(6-)CH


3


















128













437




—




O




C


3


H


7


-i




(6-)CH


3


















177













438




—




O




C


3


H


7


-i




(6-)CH


3


















165













439




—




O




CH


3






(6-)CH


3


















157













440




—




O




CH


3






(6-)CH


3


















168













441




—




O




CH


3






(6-)CH


3


















164













442




—




O




CH


3






(6-)CH


3


















125













443




—




O




CH


3






(6-)CH


3


















162













444




—




O




CH


3






(6-)OCH


3


















154













445




—




S




CH


3






(4-)C


3


H


7


-i
















116













446




—




S




CH


3






(4-)C


3


H


7


-i
















110













447




—




S




CH


3






(4-)C


3


H


7


-i
















134













448




—




O




CH


3






(4-)C


3


H


7


-i
















152













449




—




O




CH


3






(4-)C


3


H


7


-i
















159













450




—




O




CH


3






(4-)C


3


H


7


-i
















150













451




—




O




C


2


H


5






(6-)OCH


3


















107













452




—




O




C


2


H


5






(6-)OCH


3


















104













453




—




O




C


2


H


5






(6-)OCH


3


















100













454




—




S




C


2


H


5






(6-)OCH


3


















103













455




—




S




C


2


H


5






(6-)OCH


3


















 95













456




—




S




C


2


H


5






(6-)OCH


3


















105













457




—




O




C


2


H


5






(6-)OC


2


H


5


















130













458




—




O




C


2


H


5






(6-)OC


2


H


5


















100













459




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















114













460




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















125













461




—




S




C


3


H


7


-i




(6-)OC


3


H


7


-i
















143













462




—




O




C


2


H


5






(6-)OC


2


H


5


















120













463




—




O




—CF


2


CHFCl




(6-)CH


3


















124













464




—




O




—CF


2


CHFCl




(6-)CH


3


















115













465




—




O




—CF


2


CHFCl




(6-)CH


3


















150













466




—




O




CH


3






(3-)CH


3


















178













467




—




O




CH


3






(3-)Cl
















188













468




—




O




C


2


H


5






(3-)Cl
















159













469




—




O




CH


3






(3-)F
















176













470




—




O




C


2


H


5






(6-)CF


3


















124













471




—




O




C


2


H


5






(6-)CF


3


















 34













472




—




O




C


2


H


5






(6-)CF


3


















 68













473




—




O




C


3


H


7


-i




(6-)CF


3


















 41













474




—




O




C


2


H


5






(6-)CF


3


















127













475




—




O




H




(6-)CF


3


















125













476




—




S




C


2


H


5






(6-)CH


3


















214 (Na salt)













477




NH




O




C


2


H


5






(6-)CH


3


















128













478




NH




O




C


2


H


5






(6-)CH


3


















148













479




NH




O




C


3


H


7


-n




(6-)CH


3


















127













480




NH




O




C


3


H


7


-n




(6-)CH


3


















 57













481




NH




O




C


2


H


5






(6-)CH


3


















125













482




NH




O




C


3


H


7


-n




(6-)CH


3


















115













483




NH




O




C


3


H


7


-n




(6-)CH


3


















151













484




NH




O




C


2


H


5






(5-)CH


3


















132













485




NH




O




C


2


H


5






(5-)CH


3


















106













486




NH




O




C


2


H


5






(5-)CH


3


















163













487




NH




O




C


2


H


5






(5-)CH


3


















137













488




—




O




C


2


H


5






(6-)C


3


H


7


-i
















166













489




—




O




C


2


H


5






(6-)C


3


H


7


-i
















169













490




—




O




C


2


H


5






(6-)C


3


H


7


-i
















130













491




NH




O
















(6-)CH


3


















148













492




NH




O
















(6-)CH


3


















138













493




NH




O
















(6-)CH


3


















147













494




—




O
















(6-)CH


3


















124













495




—




O
















(6-)CH


3


















152













496




—




O
















(6-)CH


3


















141













497




—




O
















(6-)CH


3


















127













498




—




O
















(6-)CH


3


















144













499




—




O
















(6-)CH


3


















107













500




—




O




C


3


H


7


-n




(6-)CH


3


















265 (Na salt)













501




—




O




C


2


H


5






(6-)CH


3


















269 (Na salt)













502




—




O




C


3


H


7


-i




(6-)CH


3


















237 (Na salt)













503




—




O
















(6-)CH


3


















 73













504




—




O




C


3


H


7


-i




(6-)CH


3


















220 (Na salt)













505




—




O




C


3


H


7


-i




(6-)CH


3


















140













506




—




O




C


4


H


9


-s




(6-)CH


3


















120













507




—




O




C


4


H


9


-s




(6-)CH


3


















117













508




—




O




C


4


H


9


-s




(6-)CH


3


















128













509




—




O




C


4


H


9


-s




(6-)CH


3


















232













510




—




O




C


4


H


9


-s




(6-)CH


3


















268













511




—




O




C


4


H


9


-s




(6-)CH


3


















130













512




—




O




C


4


H


9


-s




(6-)CH


3


















137













513




—




O




C


4


H


9


-s




(6-)CH


3


















145













514




—




O




C


4


H


9


-s




(6-)CH


3


















164













515




—




O




C


4


H


9


-s




(6-)CH


3


















 89













516




—




O




C


4


H


9


-s




(6-)CH


3


















 86













517




—




O




C


4


H


9


-s




(6-)CH


3


















 98













518




—




O




C


4


H


9


-s




(6-)CH


3


















122













519




—




O




C


4


H


9


-s




(6-)CH


3


















135













520




—




O




C


2


H


5






(6-)CH


3


















142













521




—




O




CH


3






(6-)CH


3


















157













522




—




O




C


3


H


7


-n




(6-)CH


3


















126













523




—




O




C


4


H


9


-s




(6-)CH


3


















140













524




—




O




C


2


H


5






(6-)CH


3


















164













525




—




O




CH


3






(6-)CH


3


















166













526




—




O




C


3


H


7


-n




(6-)CH


3


















145













527




—




O




CH


3






(6-)CH


3


















239 (Na salt)













528




—




O




C


3


H


7


-n




(6-)CH


3


















206 (Na salt)













529




—




O




C


2


H


5






(6-)CH


3


















211 (Na salt)













530




—




O




CH


3






(6-)C


3


H


7


-i
















166













531




—




O




CH


3






(6-)C


3


H


7


-i
















178













532




—




O




C


3


H


7


-i




(6-)C


3


H


7


-i
















131













533




—




O




C


3


H


7


-i




(6-)C


3


H


7


-i
















130













534




—




O




C


3


H


7


-i




(6-)C


3


H


7


-i
















133













535




—




O




C


3


H


7


-i




(6-)C


3


H


7


-i
















116













536




—




O




CH


3






(6-)C


3


H


7


-i
















192













537




—




O




CH


3






(6-)C


3


H


7


-i
















200













538




—




O




CH


3






(6-)C


3


H


7


-i
















200













539




—




O




CH


3






(6-)C


3


H


7


-i
















105













540




—




O




CH


3






(6-)C


3


H


7


-i
















154













541




—




O




CH


3






(6-)C


3


H


7


-i
















152













542




—




O




C


3


H


7


-n




(6-)C


3


H


7


-i
















132













543




—




O




C


3


H


7


-n




(6-)C


3


H


7


-i
















129













544




—




O




C


3


H


7


-n




(6-)C


3


H


7


-i
















179













545




—




O




CH


3






(6-)C


3


H


7


-i
















174 (Na salt)













546




—




O




C


3


H


7


-n




(6-)C


3


H


7


-i
















158 (Na salt)













547




—




O




C


2


H


5






(6-)C


3


H


7


-i
















200













548




—




O




C


2


H


5






(6-)C


3


H


7


-i
















147













549




—




O




C


2


H


5






(6-)C


3


H


7


-i
















149













550




—




O




C


2


H


5






(6-)C


3


H


7


-i
















136













551




—




O




C


2


H


5






(6-)C


3


H


7


-i
















134













552




—




O




C


3


H


7


-i




(6-)C


3


H


7


-i
















175













553




—




O




C


3


H


7


-i




(6-)C


3


H


7


-i
















147













554




—




O




C


3


H


7


-i




(6-)C


3


H


7


-i
















167













555




—




O




C


3


H


7


-i




(6-)C


3


H


7


-i
















173













556




—




O




C


3


H


7


-i




(6-)CH


3


















188













557




NH




O




CH


3






(6-)CH


3


















181













558




NH




O




C


3


H


7


-i




(6-)CH


3


















136













559




—




O




CH


3






(6-)CH


3


















241 (Na salt)













560




NH




O




C


3


H


7


-n




(6-)CH


3


















129













561




—




O




C


3


H


7


-i




(6-)OCH


3


















 94













562




—




O




C


3


H


7


-i




(6-)OCH


3


















 80













563




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















 68













564




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















 91













565




—




O




C


3


H


7


-n




(6-)OCH


3


















123













566




—




O




C


3


H


7


-n




(6-)OCH


3


















104













567




—




O




C


3


H


7


-n




(6-)OCH


3


















 90













568




—




S




C


3


H


7


-n




(6-)OCH


3


















107













569




—




O




C


3


H


7


-n




(6-)OCH


3


















 70













570




—




O




C


2


H


5






(6-)OC


2


H


5


















132













571




—




S




CH


3






(6-)OCH


3


















150













572




—




O




C


2


H


5






(6-)OCH


3


















127













573




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















110













574




—




S




C


3


H


7


-n




(6-)OC


3


H


7


-n
















130













575




—




S




C


3


H


7


-n




(6-)OC


3


H


7


-n
















135













576




—




S




C


3


H


7


-n




(6-)OC


3


H


7


-n
















199 (Na salt)













577




—




O




C


2


H


5






(6-)OC


2


H


5


















173













578




—




O




C


2


H


5






(6-)OCH


3


















168













579




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















125













580




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















140













581




—




O




C


3


H


7


-n




(6-)OCH


3


















115













582




—




S




C


3


H


7


-n




(6-)OCH


3


















111













583




—




S




C


3


H


7


-n




(6-)OCH


3


















138













584




—




O




C


3


H


7


-i




(6-)OCH


3


















127













585




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















142













586




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















143













587




—




O




C


2


H


5






(6-)OCH


3


















104













588




—




O




C


2


H


5






(6-)OCH


3


















118













589




—




O




C


2


H


5






(6-)OCH


3


















 70













590




—




O




C


2


H


5






(6-)OCH


3


















110













591




—




O




C


2


H


5






(6-)OCH


3


















156













592




—




O




C


3


H


7


-n




(6-)OCH


3


















140













593




—




O




C


3


H


7


-n




(6-)OCH


3


















148













594




—




O




C


3


H


7


-n




(6-)OCH


3


















145













595




—




O




C


2


H


5






(6-)OCH


3


















120













596




—




O




C


2


H


5






(6-)OCH


3


















100













597




—




O




C


2


H


5






(6-)OCH


3


















130













598




—




O




C


2


H


5






(6-)OCH


3


















103













599




—




O




C


2


H


5






(6-)OCH


3


















104













600




—




O




C


3


H


7


-n




(6-)OCH


3


















185













601




—




O




C


3


H


7


-n




(6-)OCH


3


















100













602




—




O




C


3


H


7


-n




(6-)OCH


3


















138













603




—




O




C


3


H


7


-n




(6-)OCH


3


















106













604




—




O




C


3


H


7


-n




(6-)OCH


3


















112













605




—




O




C


3


H


7


-n




(6-)OCH


3


















140













606




—




O




C


3


H


7


-n




(6-)OCH


3


















160













607




—




O




C


3


H


7


-n




(6-)OCH


3


















180













608




—




O




C


3


H


7


-n




(6-)OCH


3


















142













609




—




O




C


3


H


7


-n




(6-)OCH


3


















158













610




—




O




C


3


H


7


-n




(6-)OCH


3


















134













611




—




O




C


3


H


7


-i




(6-)OCH


3


















140













612




—




O




C


3


H


7


-i




(6-)OCH


3


















142













613




—




O




C


3


H


7


-i




(6-)OCH


3


















148













614




—




O




C


3


H


7


-i




(6-)OCH


3


















146













615




—




O




C


3


H


7


-i




(6-)OCH


3


















104













616




—




O




C


2


H


5






(6-)OC


2


H


5


















123













617




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















123













618




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















 82













619




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















 81













620




—




S




C


3


H


7


-n




(6-)OC


3


H


7


-n
















 88













621




—




S




C


2


H


5






(6-)OCH


3


















145













622




—




S




C


2


H


5






(6-)OC


2


H


5


















147













623




—




S




C


3


H


7


-n




(6-)OCH


3


















205













624




—




S




C


3


H


7


-n




(6-)OC


2


H


5


















202













625




—




S




C


3


H


7


-i




(6-)OC


3


H


7


-i
















152













626




—




S




C


2


H


5






(6-)OC


2


H


5


















168













627




—




S




C


3


H


7


-n




(6-)C


3


H


7


-n
















145













628




—




S




C


3


H


7


-n




(6-)OCH


3


















158













629




—




S




C


3


H


7


-i




(6-)OC


3


H


7


-i
















155













630




—




O




C


3


H


7


-i




(6-)OCH


3


















145













631




—




O




C


3


H


7


-i




(6-)OCH


3


















111













632




—




O




C


3


H


7


-i




(6-)OCH


3


















122













633




—




O




C


3


H


7


-i




(6-)OCH


3


















171













634




—




O




C


3


H


7


-i




(6-)OCH


3


















160













635




—




O




C


3


H


7


-i




(6-)OCH


3


















142













636




—




O




C


2


H


5






(6-)OC


2


H


5


















106













637




—




O




C


2


H


5






(6-)OC


2


H


5


















106













638




—




O




C


2


H


5






(6-)OC


2


H


5


















159













639




—




O




C


2


H


5






(6-)OC


2


H


5


















148













640




—




O




C


2


H


5






(6-)OC


2


H


5


















126













641




—




O




C


2


H


5






(6-)OC


2


H


5


















111













642




—




O




C


2


H


5






(6-)OC


2


H


5


















171













643




—




O




C


2


H


5






(6-)OC


2


H


5


















127













644




—




O




C


2


H


5






(6-)OC


2


H


5


















148













645




—




O




C


2


H


5






(6-)OC


2


H


5


















123













646




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















138













647




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















 95













648




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















130













649




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















 74













650




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















109













651




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















 75













652




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















147













653




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















 99













654




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















102













655




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















 98













656




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















138













657




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















127













658




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















160













659




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















115













660




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















108













661




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















154













662




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















144













663




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















124













664




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















138













665




—




O




C


4


H


9


-n




(6-)OCH


3


















130













666




—




O




C


4


H


9


-n




(6-)OCH


3


















132













667




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















100













668




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















108













669




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















130













670




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















133













671




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















125













672




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















108













673




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















110













674




—




O




C


4


H


9


-n




(6-)OCH


3


















144













675




—




O




C


4


H


9


-n




(6-)OCH


3


















116













676




—




O




C


4


H


9


-n




(6-)OCH


3


















139













677




—




O




C


4


H


9


-n




(6-)OCH


3


















174













678




—




O




C


4


H


9


-n




(6-)OCH


3


















149













679




—




O




C


4


H


9


-n




(6-)OCH


3


















104













680




—




O




C


4


H


9


-n




(6-)OCH


3


















 98













681




—




O




C


4


H


9


-n




(6-)OCH


3


















112













682




—




O




C


4


H


9


-n




(6-)OCH


3


















100













683




—




O




C


4


H


9


-n




(6-)OCH


3


















 92













684




—




O




C


4


H


9


-n




(6-)OCH


3


















115













685




—




O




C


4


H


9


-n




(6-)OCH


3


















 99













686




—




O




C


4


H


9


-n




(6-)OCH


3


















102













687




—




O




C


4


H


9


-n




(6-)OCH


3


















106













688




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















120













689




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















 98













690




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















138













691




—




O




C


4


H


9


-i




(6-)OC


2


H


5


















118













692




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















138













693




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















 94













694




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















 94













695




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















 65













696




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















 60













697




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















104













698




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















104













699




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















137













700




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 70













701




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















110













702




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















102













703




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















137













704




—




O




C


3


H


7


-i




(6-)OCH


3


















160













705




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















 94













706




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















155













707




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















130













708




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















142













709




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















 85













710




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















106













711




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















 87













712




—




S




C


3


H


7


-i




(6-)OCH


3


















120













713




—




S




C


4


H


9


-n




(6-)OCH


3


















143













714




—




S




C


3


H


7


-i




(6-)OC


3


H


7


-i
















152













715




—




S




C


2


H


4


OC


2


H


5






(6-)OCH


3


















112













716




—




S




C


3


H


7


-i




(6-)OCH


3


















130













717




—




S




C


3


H


7


-i




(6-)OCH


3


















165













718




—




S




C


3


H


7


-i




(6-)OC


3


H


7


-i
















161













719




—




S




C


4


H


9


-n




(6-)OCH


3


















111













720




—




S




C


2


H


5






(6-)OCH


3


















156













721




—




S




C


2


H


4


OC


2


H


5






(6-)OCH


3


















137













722




—




S




CH


3






(6-)OCH


3


















163













723




—




S




C


3


H


7


-n




(6-)OCH


3


















113













724




—




S




C


3


H


7


-n




(6-)OCH


3


















130













725




—




S




C


4


H


9


-n




(6-)OCH


3


















154













726




—




S




C


3


H


7


-i




(6-)OC


3


H


7


-i
















157













727




—




S




C


3


H


7


-n




(6-)OC


3


H


7


-n
















142













728




—




S




C


2


H


5






(6-)OC


2


H


5


















162













729




—




S




CH


3






(6-)OCH


3


















157













730




—




S




C


2


H


5






(6-)OCH


3


















108













731




—




S




CH


3






(6-)OCH


3


















172













732




—




S




CH


3






(6-)OCH


3


















147













733




—




S




C


3


H


7


-n




(6-)OC


3


H


7


-n
















160













734




—




S




C


3


H


7


-n




(6-)OC


3


H


7


-n
















103













735




—




O




C


3


H


7


-n




(6-)OC


3


H


7


-n
















172













736




—




S




C


2


H


5






(6-)OC


2


H


5


















137













737




—




S




C


2


H


5






(6-)OC


2


H


5


















156













738




—




S




C


2


H


4


OC


2


H


5






(6-)OCH


3


















103













739




—




S




C


3


H


7


-i




(6-)OC


3


H


7


-i
















134













740




—




S




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 87













741




—




S




C


4


H


9


-n




(6-)OC


4


H


9


-n
















110













742




—




S




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 88













743




—




S




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 98













744




—




S




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 98













745




—




S




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 88













746




—




S




C


4


H


9


-n




(6-)OC


4


H


9


-n
















104













747




—




S




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 75













748




—




O




C


2


H


5






(6-)OC


2


H


5


















145













749




—




S




C


3


H


7


-i




(6-)OC


2


H


5


















131













750




—




S




C


3


H


7


-i




(6-)OC


2


H


5


















158













751




—




S




C


3


H


7


-i




(6-)OC


2


H


5


















132













752




—




S




C


3


H


7


-i




(6-)OC


2


H


5


















142













753




—




S




C


3


H


7


-i




(6-)OC


2


H


5


















130













754




—




S




C


3


H


7


-i




(6-)OC


2


H


5


















170













755




—




S




C


3


H


7


-n




(6-)OC


2


H


5


















152













756




—




S




C


3


H


7


-n




(6-)OC


2


H


5


















138













757




—




S




C


3


H


7


-n




(6-)OC


2


H


5


















130













758




—




S




C


3


H


7


-n




(6-)OC


2


H


5


















150













759




—




S




C


3


H


7


-n




(6-)OC


2


H


5


















156













760




—




S




C


3


H


7


-n




(6-)OC


2


H


5


















110













761




—




S




C


3


H


7


-n




(6-)OC


2


H


5


















120













762




—




S




C


4


H


9


-n




(6-)OC


4


H


9


-n
















104













763




—




S




C


3


H


7


-i




(6-)OCH


3


















105













764




—




S




C


3


H


7


-n




(6-)OC


3


H


7


-n
















120













765




—




S




C


3


H


7


-n




(6-)OCH


3


















135













766




—




S




C


3


H


7


-n




(6-)OC


3


H


7


-n
















116













767




—




S




C


3


H


7


-i




(6-)OC


3


H


7


-i
















110













768




—




S




C


2


H


4


OC


2


H


5






(6-)OCH


3


















 95













769




—




S




C


3


H


7


-i




(6-)OCH


3


















112













770




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















 70













771




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















132













772




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















 75













773




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















118













774




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















 85













775




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















130













776




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















120













777




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















124













778




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















130













779




—




O




C


3


H


7


-i




(6-)OC


2


H


5


















100













780




—




O




C


2


H


5






(6-)OCH


3


















172













781




—




O




C


2


H


5






(6-)OCH


3


















164













782




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















118













783




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















 88













784




—




O




C


4


H


9


-s




(6-)OCH


3


















124













785




—




O




C


4


H


9


-s




(6-)OCH


3


















100













786




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















106













787




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















108













788




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















105













789




—




O




C


4


H


9


-s




(6-)OCH


3


















112













790




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















 80













791




—




O




C


4


H


9


-s




(6-)OCH


3


















130













792




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















120













793




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















 95













794




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















 96













795




—




O




C


4


H


9


-s




(6-)OCH


3


















130













796




—




G




C


4


H


9


-s




(6-)OCH


3


















118













797




—




O




C


4


H


9


-s




(6-)OCH


3


















134













798




—




O




C


4


H


9


-s




(6-)OCH


3


















118













799




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















 90













800




—




O




C


4


H


9


-s




(6-)OCH


3


















 78













801




—




O




C


4


H


9


-s




(6-)OCH


3


















112













802




—




O




C


4


H


9


-s




(6-)OCH


3


















 78













803




—




O




C


4


H


9


-s




(6-)OCH


3


















 80













804




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 55













805




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















100













806




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 92













807




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















 74













808




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















143













809




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















102













810




—




O




C


3


H


7


-n




(6-)OC


2


H


5


















 95













811




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















 82













812




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















 92













813




—




O




C


4


H


9


-n




(6-)OCH


3


















 90













814




—




O




C


4


H


9


-n




(6-)OCH


3


















124













815




—




O




C


4


H


9


-n




(6-)OCH


3


















 85













816




—




O




C


4


H


9


-n




(6-)OCH


3


















 90













817




—




O




C


2


H


4


OC


2


H


5






(6-)OCH


3


















 90













818




—




O
















(6-)OCH


3


















165













819




—




O
















(6-)OCH


3


















130













820




—




O
















(6-)OCH


3


















149













821




—




O




C


4


H


9


-s




(6-)OC


4


H


9


-s
















125













822




—




O
















(6-)OCH


3


















112













823




—




O
















(6-)OCH


3


















156













824




—




O
















(6-)OCH


3


















148













825




—




O
















(6-)OCH


3


















145













826




—




O
















(6-)OCH


3


















156













827




—




O
















(6-)OCH


3


















126













828




—




O
















(6-)OCH


3


















134













829




—




O
















(6-)OCH


3


















114













830




—




O
















(6-)OCH


3


















141













831




—




O




C


4


H


9


-i




(6-)OC


2


H


5


















125













832




—




O




C


4


H


9


-i




(6-)OC


2


H


5


















128













833




—




O




C


4


H


9


-i




(6-)OC


2


H


5


















106













834




—




O




C


4


H


9


-i




(6-)OC


2


H


5


















 88













835




—




O




C


4


H


9


-i




(6-)OC


2


H


5


















112













836




—




O




C


4


H


9


-i




(6-)OC


2


H


5


















125













837




—




O




C


4


H


9


-i




(6-)OC


2


H


5


















106













838




—




O




H




(6-)OH
















172













839




—




O




C


4


H


9


-i




(6-)OCH


3


















102













840




—




O




C


4


H


9


-i




(6-)OCH


3


















114













841




—




O




C


4


H


9


-i




(6-)OCH


3


















124













842




—




O




C


4


H


9


-i




(6-)OCH


3


















 98













843




—




O




C


4


H


9


-i




(6-)OCH


3


















146













844




—




O




C


4


H


9


-i




(6-)OCH


3


















 97













845




—




O




C


4


H


9


-i




(6-)OCH


3


















117













846




—




O




C


4


H


9


-i




(6-)OCH


3


















142













847




—




O




C


4


H


9


-i




(6-)OCH


3


















109













848




—




S




C


2


H


5






(6-)OCH


3


















138













849




—




S




C


2


H


5






(6-)OCH


3


















135













850




—




S




C


2


H


5






(6-)OCH


3


















155













851




—




S




C


2


H


5






(6-)OCH


3


















160













852




—




S




C


4


H


9


-s




(6-)OCH


3


















108













853




—




S




C


4


H


9


-s




(6-)OCH


3


















143













854




—




S




C


4


H


9


-s




(6-)OCH


3


















105













855




—




S




C


4


H


9


-s




(6-)OCH


3


















 65













856




—




S




C


4


H


9


-s




(6-)OCH


3


















114













857




—




O




C


2


H


5






(3-)CH


3


















179













858




—




S




C


4


H


9


-s




(6-)OCH


3


















146













859




—




S




C


3


H


7


-i




(6-)OCH


3


















146













860




—




S




C


4


H


9


-n




(6-)OCH


3


















132













861




—




S




C


4


H


9


-n




(6-)OCH


3


















112













862




—




S




C


4


H


9


-n




(6-)OCH


3


















100













863




—




S




C


4


H


9


-n




(6-)OCH


3


















138













864




—




S




C


3


H


7


-i




(6-)OC


2


H


5


















155













865




—




S




C


3


H


7


-i




(6-)OC


2


H


5


















140













866




—




S




C


4


H


9


-n




(6-)OCH


3


















140













867




—




O




C


4


H


9


-i




(6-)OCH


3


















131













868




—




O




C


4


H


9


-i




(6-)OCH


3


















135













869




—




O




C


4


H


9


-i




(6-)OCH


3


















137













870




—




O




C


4


H


9


-n




(6-)OC


4


H


9


-n
















123













871




—




O




C


4


H


9


-n




(6-)OC


2


H


5


















118













872




—




O
















(6-)OCH


3


















164













873




—




O




C


3


H


7


-i




(6-)OCH


3


















150













874




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















148













875




—




O




C


3


H


7


-n




(6-)OCH


3


















147













876




—




O




C


2


H


5






(6-)OC


2


H


5


















108













877




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















108













878




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















148













879




—




O




C


2


H


5






(6-)OC


2


H


5


















176













880




—




O




C


3


H


7


-n




(6-)OCH


3


















144













881




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















167













882




—




O




C


2


H


5






(6-)OC


2


H


5


















135













883




—




O




C


3


H


7


-n




(6-)OCH


3


















100













884




—




O




C


2


H


5






(6-)OC


2


H


5


















158













885




—




O




C


3


H


7


-n




(6-)OCH


3


















108













886




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















164













887




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















157













888




—




O




C


3


H


7


-n




(6-)OCH


3


















113













889




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















132













890




—




O




C


3


H


7


-n




(6-)OCH


3


















 92













891




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















141













892




—




O




C


3


H


7


-i




(6-)OC


3


H


7


-i
















159













893




—




O




C


2


H


5






(6-)OC


2


H


5


















139













894




—




O




C


2


H


5






(6-)OC


2


H


5


















150













895




—




O




C


3


H


7


-n




(6-)OCH


3


















126













896




—




O




C


3


H


7


-i




(6-)CH


3


















148













897




—




O




C


3


H


7


-i




(6-)CH


3


















157













898




—




O




C


3


H


7


-i




(6-)CH


3


















125













899




NH




O




CH


3






(6-)OCH


3


















182













900




NH




O




CH


3






(6-)OCH


3


















175













901




—




O




CF


3






(6-)CH


3


















198 (Na salt)













902




—




O




CF


3






(6-)CH


3


















129













903




—




O




CF


3






(6-)CH


3


















149













904




—




O




CF


3






(6-)CH


3


















163













905




—




O




CF


3






(6-)C


2


H


5


















121













906




—




O




C


3


H


7


-i




(6-)CH


3


















170













907




—




O




C


3


H


7


-i




(6-)CH


3


















125













908




—




O




C


3


H


7


-i




(6-)CH


3


















129













909




—




O




C


3


H


7


-i




(6-)CH


3


















156













910




—




O




CH


3






(6-)OCH


3


















157













911




—




O




CH


3






(6-)OCH


3


















177













912




—




O




CH


3






(6-)OCH


3


















172













913




—




O




C


3


H


7


-i




(6-)CH


3


















132













914




—




O




C


3


H


7


-i




(6-)CH


3


















153













915




—




O




C


3


H


7


-i




(6-)CH


3


















150













916




—




O




C


3


H


7


-i




(6-)CH


3


















110













917




—




O




C


3


H


7


-i




(6-)CH


3


















131













918




—




O




C


3


H


7


-i




(6-)CH


3


















133













919




—




O




CH


3






(6-)OCH


3


















153













920




—




O




C


3


H


7


-i




(6-)CH


3


















122













921




—




O




C


3


H


7


-i




(6-)CH


3


















147













922




—




O




CH


3






(6-)OCH


3


















160













923




—




O




CH


3






(6-)OCH


3


















182













924




—




O




CH


3






(6-)OCH


3


















142













925




—




O




CH


3






(6-)OCH


3


















178













926




—




O




C


3


H


7


-i




(6-)CH


3


















151













927




—




O




CH


3






(6-)OCH


3


















178













928




—




O




CH


3






(6-)OCH


3


















130













929




—




O




CH


3






(6-)OCH


3


















124













930




—




O




CH


3






(6-)OCH


3


















153













931




—




O




CH


3






(6-)OCH


3


















157













932




—




O




CH


3






(6-)OCH


3


















114













933




—




O




CH


3






(6-)OCH


3


















130













934




—




O




C


3


H


7


-i




(6-)CH


3


















151













935




—




O




C


3


H


7


-i




(6-)CH


3


















153













936




—




O




CH


3






(6-)OCH


3


















167













937




—




O




CF


2


Cl




(6-)CH


3


















180 (Na salt)













938




—




O




CH


3






(6-)OCH


3


















157 (Na salt)













939




NH




O




CH


2


CH


2


F




(6-)CH


3


















163













940




NH




O




CH


2


CHF


2






(6-)CH


3


















160













941




NH




O




CF


2


CHFCl




(6-)CH


3


















 88













942




—




O




CH


2


CH


2


F




(6-)CH


3


















178













943




—




O




CH


2


CH


2


F




(6-)CH


3


















135













944




—




O




CH


2


CH


2


F




(6-)CH


3


















127













945




—




O




CH


2


CH


2


F




(6-)CH


3


















139













946




—




O




CH


2


CH


2


F




(6-)CH


3


















280 (Na salt)













947




—




O




CH


2


CH


2


F




(6-)CH


3


















171













948




—




O




CH


2


CH


2


F




(6-)CH


3


















144













949




—




O




CH


2


CHF


2






(6-)CH


3


















273 (Na salt)













950




—




O




CH


2


CHF


2






(6-)CH


3


















181













951




—




O




CH


2


CHF


2






(6-)CH


3


















142













952




—




O




CH


2


CHF


2






(6-)CH


3


















114













953




—




O




CH


2


CHF


2






(6-)CH


3


















108













954




—




O




CH


2


CHF


2






(6-)CH


3


















185













955




—




O




CH


2


CHF


2






(6-)CH


3


















150













956




—




O




CF


3






(6-)C


2


H


5


















143 (Na salt)













957




—




O




CF


3






(6-)CH


3


















155













958




—




O




CF


3






(6-)CH


3


















112













959




—




O




CF


3






(6-)CH


3


















166













960




—




O




CF


3






(6-)CH


3


















137













961




—




O




CF


3






(6-)CH


3


















132













962




—




O




CF


3






(6-)CH


3


















172













963




—




O




CF


3






(6-)CH


3


















139













964




—




O




CF


3






(6-)CH


3


















130













965




—




O




C


2


H


5






(3-)CH


3


















184






















TABLE 1A











Examples of the compounds of the formula (IA)




















(IA)








































Ex.







(Position-)







Melting






No.




A




Q




R


1






R


2






Q


1






R


4






R


5






point ° C.









966




NH




O




C


4


H


9






(6-)CH


3






O
















OC


2


H


5






121













967




NH




O




CH


2


CH(CH


3


)


2






(6-)CH


3






O
















OC


2


H


5






127






968




NH




O




CH


2


CF


3






(6-)CH


3






O




CH


3






OCH


3






164






969




NH




O




CH


2


CF


3






(6-)CH


3






O




CH


3






OC


2


H


5






138






970




NH




O




CH


2


CF


3






(6-)CH


3






O




CH


3






OC


3


H


7






123






971




NH




O




CH


2


CF


3






(6-)CH


3






O




CH


3






OCH(CH


3


)


2






141






972




—




O




CH


2


CH


2


F




(3-)Cl




O




CH


3






OC


2


H


5






139






973




—




O




CH


2


CH


2


F




(3-)CH


3






O




CH


3






OC


2


H


5






154













974




—




O




C


3


H


7


-i




(6-)CF


3






O
















C


4


H


9


-s













975




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






C


4


H


9


-s






976




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






C


4


H


9








977




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






C


4


H


9


-i






978




—




S




C


3


H


7


-i




(6-)CF


3






O




CH


3






C


2


H


5















979




—




S




C


3


H


7






(6-)CH


3






O
















OC


2


H


5















980




—




S




C


3


H


7






(6-)CH


3






O




C


2


H


5






OC


2


H


5















981




—




3




C


3


H


7


-i




(6-)CH


3






O
















OC


2


H


5















982




—




S




C


3


H


7


-i




(6-)CH


3






O




C


2


H


5






OC


2


H


5








983




—




S




C


3


H


7






(6-)CH


3






O




CH


3






OC


3


H


7


-i






984




—




S




C


3


H


7


-i




(6-)CH


3






O




CH


3






OC


3


H


7


-i






985




—




S




C


3


H


7






(6-)CH


3






O




CH


3






OC


3


H


7








986




—




S




C


3


H


7


-i




(6-)CH


3






O




CH


3






OC


3


H


7















987




—




S




C


3


H


7






(6-)CH


3






O
















OCH


3















988




—




O




CH


3






(6-)CF


3






O
















C


4


H


9


-s













989




—




O




C


2


H


5






(6-)CF


3






O
















C


4


H


9


-s













990




—




O




C


3


H


7






(6-)CF


3






O
















C


4


H


9


-s













991




—




O




CH


3






(6-)CF


3






O




CH


3






C


4


H


9


-s






992




—




O




C


2


H


5






(6-)CF


3






O




CH


3






C


4


H


9


-s






993




—




O




CH


3






(6-)CF


3






O




CH


3






C


4


H


9















994




—




O




CH


3






(6-)CF


3






O
















C


4


H


9


-t













995




—




O




CH


3






(6-)CF


3






O
















OC


3


H


7















996




—




O




C


2


H


5






(6-)CF


3






O
















OC


3


H


7















997




—




O




C


3


H


7






(6-)CF


3






O
















OC


3


H


7















998




—




O




C


2


H


5






(6-)CF


3






O




CH


3






C


4


H


9








999




—




O




C


3


H


7






(6-)CF


3






O




CH


3






C


4


H


9








1000




—




O




CH


3






(6-)CF


3






O




CH


3






C


4


H


9


-i






1001




—




S




CH


3






(6-)CF


3






O




CH


3






SCH


3















1002




—




S




CH


3






(6-)CF


3






O
















OC


2


H


5















1003




—




S




CH


3






(6-)CF


3






O




CH


3






OC


3


H


7


-i






1004




—




S




CH


3






(6-)CF


3






O




C


2


H


5






OC


2


H


5















1005




—




S




CH


3






(6-)CF


3






O
















OC


3


H


7















1006




—




S




CH


3






(6-)CF


3






O
















OC


3


H


7


-i













1007




—




S




CH


3






(6-)CF


3






O




CH


3






OCH


2


CF


3








1008




—




S




CH


3






(6-)CF


3






O




CH


3






OC


3


H


7















1009




—




S




CH


3






(6-)CF


3






O





































1010




—




S




CH


3






(6-)CF


3






O
















OCH


3















1011




—




S




CH


3






(6-)CF


3






O
















OCH


2


CF


3















1012




—




S




CH


3






(6-)CH


3






O




CH


3






CH


3








1013




—




S




CH


3






(6-)CH


3






O




CH


3






OCH


3








1014




—




S




CH


3






(6-)CH


3






O




CH


3






OC


2


H


5








1015




—




S




CH


3






(6-)CH


3






O




CH


3






C


2


H


5








1016




—




S




C


2


H


5






(6-)CH


3






O




CH


3






C


2


H


5








1017




—




S




CH


3






(6-)CH


3






O




CH


3






SCH


3








1018




—




S




C


2


H


5






(6-)CH


3






O




CH


3






SCH


3















1019




—




S




CH


3






(6-)CH


3






O
















OC


2


H


5















1020




—




S




C


2


H


5






(6-)CH


3






O
















OC


2


H


5















1021




—




S




CH


3






(6-)CH


3






O




CH


3






OC


3


H


7


-i













1022




—




S




C


2


H


5






(6-)CH


3






O
















OC


3


H


7















1023




—




O




CH


3






(6-)CF


3






O
















OCH


2


CF


3















1024




—




O




CH


3






(6-)CF


3






O
















C


3


H


7


-i













1025




—




O




CH


3






(6-)CF


3






O




CH


3






C


4


H


9


-t













1026




—




O




CH


3






(6-)CF


3






O
















C


3


H


7















1027




—




O




CH


3






(6-)CF


3






O
















C


3


H


7


-i













1028




—




O




CH


3






(6-)CF


3






O




C


2


H


5






C


2


H


5








1029




—




O




CH


3






(6-)CF


3






O




C


3


H


7






C


2


H


5








1030




—




O




CH


3






(6-)CF


3






O




C


3


H


7


-i




C


2


H


5








1031




—




O




CH


3






(6-)CF


3






O




C


2


H


5






C


3


H


7








1032




—




O




CH


3






(6-)CF


3






O




C


3


H


7






C


3


H


7








1033




—




O




CH


3






(6-)CF


3






O




N(CH


3


)


2






CH


3








1034




—




O




CH


3






(6-)CF


3






O




CH


3






H






1035




—




O




CH


3






(6-)CF


3






O




CH


3






CH


2


CH


2


O













1036




—




O




CH


3






(6-)CF


3






O




CH


3



























1037




—




O




CH


3






(6-)CF


3






O




C


3


H


7


-i




C


3


H


7








1038




—




O




CH


3






(6-)CF


3






O




C


2


H


5






C


3


H


7


-i






1039




—




O




CH


3






(6-)CF


3






O




C


3


H


7






C


3


H


7


-i






1040




—




O




CH


3






(6-)CF


3






O




C


3


H


7


-i




C


3


H


7


-i













1041




—




O




CH


3






(6-)CF


3






O




C


2


H


5



























1042




—




O




CH


3






(6-)CF


3






O




C


3


H


7



























1043




—




O




CH


3






(6-)CF


3






O




C


3


H


7


-i

























1044




—




O




C


2


H


5






(6-)CF


3






O




C


3


H


7


-i

























1045




—




O




C


3


H


7






(6-)CF


3






O




C


3


H


7


-i

























1046




—




O




CH


3






(6-)CF


3






O




CH


3






OCH


2


CF


2


CHF


2








1047




—




O




C


3


H


7






(6-)CF


3






O




CH


3






OCH


2


CF


2


CHF


2








1048




—




O




CH


3






(6-)CF


3






O




CH


3






OC


6


H


11








1049




—




O




C


2


H


5






(6-)CF


3






O




CH


3






OC


6


H


11








1050




—




O




C


3


H


7






(6-)CF


3






O




CH


3






OC


6


H


11















1051




—




O




CH


3






(6-)CF


3






O




CH


3



























1052




—




O




CH


3






(6-)CF


3






O
















C


4


H


9


-i













1053




—




O




CH


3






(6-)CF


3






O
















C


4


H


9















1054




—




O




CH


3






(6-)CF


3






O
















CH


3















1055




—




O




CH


3






(6-)CF


3






O
















C


2


H


5















1056




—




O




CH


3






(6-)CF


3






O





































1057




—




O




CH


3






(6-)CF


3






O




C


2


H


5






CH


3















1058




—




O




C


3


H


7


-i




(6-)CF


3






O




C


3


H


7


-i


















1059




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






OCH


2


CF


2


CHF


2








1060




—




O




C


3


H


7






(6-)CF


3






O




CH


3






CH


3








1061




—




O




C


3


H


7






(6-)CF


3






O




CH


3






C


3


H


7


-i






1062




—




O




C


3


H


7






(6-)CF


3






O




CH


3






CH


2


OCH


3








1063




—




O




C


3


H


7






(6-)CF


3






O




CH


3






Br






1064




—




O




C


2


H


5






(6-)CF


3






O




CH


3






OCH


2


CF


3








1065




—




O




C


3


H


7






(6-)CF


3






O




OCH


3






C


3


H


7















1066




—




O




C


3


H


7






(6-)CF


3






O
















Br













1067




—




O




C


2


H


5






(6-)CF


3






O
















CH


2


OCH


3















1068




—




O




C


3


H


7






(6-)CF


3






O
















CH


2


OCH


3















1069




—




S




C


2


H


5






(6-)CF


3






O




CH


3






SCH


3








1070




—




S




C


3


H


7






(6-)CF


3






O




CH


3






SCH


3








1071




—




S




C


3


H


7


-i




(6-)CF


3






O




CH


3






SCH


3















1072




—




S




C


2


H


5






(6-)CF


3






O
















OC


2


H


5















1073




—




S




C


3


H


7






(6-)CF


3






O
















OC


2


H


5















1074




—




S




C


3


H


7


-i




(6-)CF


3






O
















OC


2


H


5















1075




—




S




C


2


H


5






(6-)CF


3






O




CH


3






OC


3


H


7


-i






1076




—




S




C


3


H


7






(6-)CF


3






O




CH


3






OC


3


H


7


-i






1077




—




S




C


3


H


7


-i




(6-)CF


3






O




CH


3






OC


3


H


7


-i






1078




—




S




C


2


H


5






(6-)CF


3






O




C


2


H


5






OC


2


H


5








1079




—




S




C


3


H


7






(6-)CF


3






O




C


2


H


5






OC


2


H


5








1080




—




S




C


3


H


7


-i




(6-)CF


3






O




C


2


H


5






OC


2


H


5















1081




—




S




C


2


H


5






(6-)CF


3






O
















OC


3


H


7















1082




—




S




C


3


H


7






(6-)CF


3






O
















OC


3


H


7















1083




—




S




C


3


H


7


-i




(6-)CF


3






O
















OC


3


H


7















1084




—




O




C


3


H


7


-i




(6-)CF


3






O
















C


4


H


9


-t













1085




—




O




C


2


H


5






(6-)CF


3






O




CH


3






OC


4


H


9


-s













1086




—




O




C


3


H


7






(6-)CF


3






O




CH


3



























1087




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






OC


4


H


9


-s






1088




—




O




C


2


H


5






(6-)CF


3






O




CH


3






OC


6


H


5








1089




—




O




C


3


H


7






(6-)CF


3






O




CH


3






OC


6


H


5








1090




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






OC


6


H


5








1091




—




O




C


2


H


5






(6-)CF


3






O




CH


2


CH═CH


2






OCH


2


CF


3








1092




—




O




C


3


H


7






(6-)CF


3






O




CH


2


CH═CH


2






OCH


2


CF


3








1093




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


2


CH═CH


2






OCH


2


CF


3








1094




—




O




C


2


H


5






(6-)CF


3






O




CH


3






OCH


2


C


6


H


5








1095




—




O




C


3


H


7






(6-)CF


3






O




CH


3






OCH


2


C


6


H


5








1096




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






OCH


2


C


6


H


5








1097




—




O




C


2


H


5






(6-)CF


3






O




N(CH


3


)


2






CH


3








1098




—




O




C


3


H


7






(6-)CF


3






O




N(CH


3


)


2






CH


3








1099




—




O




C


3


H


7


-i




(6-)CF


3






O




N(CH


3


)


2






CH


3








1100




—




O




C


3


H


7






(6-)CF


3






O




CH


3






H






1101




—




O




C


2


H


5






(6-)CF


3






O




CH


3






CH


2


CH


2


OC


3


H


7


-i






1102




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






CH


2


CH


2


OC


3


H


7


-i













1103




—




O




C


2


H


5






(6-)CF


3






O




CH


3



























1104




—




O




C


3


H


7






(6-)CF


3






O




CH


3



























1105




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3



























1106




—




O




C


2


H


5






(6-)CF


3






O




CH


3






OCH


2


CF


2


CHF


2















1107




—




S




C


3


H


7


-i




(6-)CH


3






O
















OCH


3















1108




—




S




C


3


H


7






(6-)CH


3






O
















OC


3


H


7


-i













1109




—




S




C


3


H


7


-i




(6-)CH


3






O
















OC


3


H


7


-i













1110




—




S




C


3


H


7






(6-)CH


3






O
















OC


3


H


7















1111




—




S




C


3


H


7


-i




(6-)CH


3






O
















OC


3


H


7















1112




—




O




C


2


H


5






(6-)CF


3






O
















C


4


H


9


-i













1113




—




O




C


3


H


7






(6-)CF


3






O
















C


4


H


9


-i













1114




—




O




C


3


H


7


-i




(6-)CF


3






O
















C


4


H


9


-i













1115




—




O




C


2


H


5






(6-)CF


3






O
















C


4


H


9















1116




—




O




C


3


H


7






(6-)CF


3






O
















C


4


H


9















1117




—




O




C


3


H


7


-i




(6-)CF


3






O
















C


4


H


9















1118




—




O




C


2


H


5






(6-)CF


3






O
















CH


3















1119




—




O




C


3


H


7






(6-)CF


3






O
















CH


3















1120




—




O




C


3


H


7


-i




(6-)CF


3






O
















CH


3















1121




—




O




C


2


H


5






(6-)CF


3






O
















C


2


H


5















1122




—




O




C


3


H


7






(6-)CF


3






O
















C


2


H


5















1123




—




O




C


3


H


7


-i




(6-)CF


3






O
















C


2


H


5















1124




—




O




C


2


H


5






(6-)CF


3






O





































1125




—




O




C


3


H


7






(6-)CF


3






O





































1126




—




O




C


3


H


7


-i




(6-)CF


3






O





































1127




—




O




C


2


H


5






(6-)CF


3






O




C


3


H


7



























1128




—




O




C


3


H


7






(6-)CF


3






O




C


3


H


7



























1129




—




O




C


3


H


7


-i




(6-)CF


3






O




C


3


H


7



























1130




—




O




C


2


H


5






(6-)CF


3






O




C


2


H


5






CH


3








1131




—




O




C


3


H


7






(6-)CF


3






O




C


2


H


5






CH


3








1132




—




O




C


3


H


7


-i




(6-)CF


3






O




C


2


H


5






CH


3















1133




—




O




C


2


H


5






(6-)CF


3






O
















C


3


H


7















1134




—




O




C


3


H


7






(6-)CF


3






O
















C


3


H


7















1135




—




O




C


3


H


7


-i




(6-)CF


3






O
















C


3


H


7















1136




—




O




C


2


H


5






(6-)CF


3






O
















C


3


H


7


-i













1137




—




O




C


3


H


7






(6-)CF


3






O
















C


3


H


7


-i













1138




—




O




C


3


H


7


-i




(6-)CF


3






O
















C


3


H


7


-i













1139




—




O




C


2


H


5






(6-)CF


3






O




C


2


H


5






C


2


H


5








1140




—




O




C


3


H


7






(6-)CF


3






O




C


2


H


5






C


2


H


5








1141




—




O




C


3


H


7


-i




(6-)CF


3






O




C


2


H


5






C


2


H


5








1142




—




O




C


2


H


5






(6-)CF


3






O




C


3


H


7






C


2


H


5








1143




—




O




C


3


H


7






(6-)CF


3






O




C


3


H


7






C


2


H


5








1144




—




O




C


3


H


7


-i




(6-)CF


3






O




C


3


H


7






C


2


H


5















1145




—




S




C


2


H


5






(6-)CF


3






O
















OC


3


H


7


-i













1146




—




S




C


3


H


7






(6-)CF


3






O
















OC


3


H


7


-i













1147




—




S




C


3


H


7


-i




(6-)CF


3






O
















OC


3


H


7


-i













1148




—




S




C


2


H


5






(6-)CF


3






O




CH


3






OCH


2


CF


3








1149




—




S




C


3


H


7






(6-)CF


3






O




CH


3






OCH


2


CF


3








1150




—




S




C


3


H


7


-i




(6-)CF


3






O




CH


3






OCH


2


CF


3








1151




—




S




C


2


H


5






(6-)CF


3






O




CH


3






OC


3


H


7








1152




—




S




C


3


H


7






(6-)CF


3






O




CH


3






OC


3


H


7








1153




—




S




C


3


H


7


-i




(6-)CF


3






O




CH


3






OC


3


H


7















1154




—




S




C


2


H


5






(6-)CF


3






O





































1155




—




S




C


3


H


7






(6-)CF


3






O





































1156




—




S




C


3


H


7


-i




(6-)CF


3






O





































1157




—




S




C


2


H


5






(6-)CF


3






O
















OCH


3















1158




—




S




C


3


H


7






(6-)CF


3






O
















OCH


3















1159




—




S




C


3


H


7


-i




(6-)CF


3






O
















OCH


3















1160




—




S




C


2


H


5






(6-)CF


3






O
















OCH


2


CF


3















1161




—




S




C


3


H


7






(6-)CF


3






O
















OCH


2


CF


3















1162




—




S




C


3


H


7


-i




(6-)CF


3






O
















OCH


2


CF


3















1163




—




O




C


2


H


5






(6-)CF


3






O




C


3


H


7


-i




C


3


H


7








1164




—




O




C


3


H


7






(6-)CF


3






O




C


3


H


7


-i




C


3


H


7








1165




—




O




C


3


H


7


-i




(6-)CF


3






O




C


3


H


7


-i




C


3


H


7








1166




—




O




C


2


H


5






(6-)CF


3






O




C


2


H


5






C


3


H


7


-i






1167




—




O




C


3


H


7






(6-)CF


3






O




C


2


H


5






C


3


H


7


-i






1168




—




O




C


3


H


7


-i




(6-)CF


3






O




C


2


H


5






C


3


H


7


-i






1169




—




O




C


2


H


5






(6-)CF


3






O




C


3


H


7






C


3


H


7


-i






1170




—




O




C


3


H


7






(6-)CF


3






O




C


3


H


7






C


3


H


7


-i






1171




—




O




C


3


H


7


-i




(6-)CF


3






O




C


3


H


7






C


3


H


7


-i






1172




—




O




C


2


H


5






(6-)CF


3






O




C


3


H


7


-i




C


3


H


7


-i






1173




—




O




C


3


H


7






(6-)CF


3






O




C


3


H


7


-i




C


3


H


7


-i






1174




—




O




C


3


H


7


-i




(6-)CF


3






O




C


3


H


7


-i




C


3


H


7


-i






1175




—




O




C


2


H


5






(6-)CF


3






O




C


3


H


7


-i




C


2


H


5








1176




—




O




C


3


H


7






(6-)CF


3






O




C


3


H


7


-i




C


2


H


5








1177




—




O




C


3


H


7


-i




(6-)CF


3






O




C


3


H


7


-i




C


2


H


5








1178




—




O




C


2


H


5






(6-)CF


3






O




C


2


H


5






C


3


H


7








1179




—




O




C


3


H


7






(6-)CF


3






O




C


2


H


5






C


3


H


7








1180




—




O




C


3


H


7


-i




(6-)CF


3






O




C


2


H


5






C


3


H


7








1181




—




O




C


2


H


5






(6-)CF


3






O




C


3


H


7






C


3


H


7








1182




—




O




C


3


H


7






(6-)CF


3






O




C


3


H


7






C


3


H


7








1183




—




O




C


3


H


7


-i




(6-)CF


3






O




C


3


H


7






C


3


H


7








1184




—




O




C


2


H


5






(6-)CF


3






O




CH


3






C


4


H


9


-t






1185




—




O




C


3


H


7






(6-)CF


3






O




CH


3






C


4


H


9


-t






1186




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






C


4


H


9


-t













1187




—




O




C


2


H


5






(6-)CF


3






O
















C


4


H


9


-t













1188




—




O




C


3


H


7






(6-)CF


3






O
















C


4


H


9


-t













1189




—




O




C


2


H


5






(6-)CF


3






O




C


2


H


5



























1190




—




O




C


3


H


7






(6-)CF


3






O




C


2


H


5



























1191




—




O




C


3


H


7


-i




(6-)CF


3






O




C


2


H


5



























1192




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






OC


6


H


11








1193




—




S




C


3


H


7






(6-)CH


3






O




CH


3






OCH


2


CF


3








1194




—




S




C


3


H


7


-i




(6-)CH


3






O




CH


3






OCH


2


CF


3















1195




—




S




C


3


H


7






(6-)CH


3






O
















OCH


2


CF


3















1196




—




S




C


3


H


7


-i




(6-)CH


3






O
















OCH


2


CF


3















1197




—




S




C


3


H


7


-i




(6-)CH


3






O




CH


3






C


2


H


5








1198




—




S




CH


3






(6-)CF


3






O




CH


3






C


2


H


5








1199




—




S




C


2


H


5






(6-)CF


3






O




CH


3






C


2


H


5








1200




—




S




C


3


H


7






(6-)CF


3






O




CH


3






C


2


H


5















1201




—




O




C


2


H


5






(6-)CF


3






O
















H













1202




—




O




CH


3






(6-)CF


3






O
















H













1203




—




O




C


3


H


7






(6-)CF


3






O
















H













1204




—




O




C


3


H


7


-i




(6-)CF


3






O
















H













1205




—




O




C


2


H


5






(6-)CF


3






O
















OCH


3















1206




—




O




C


3


H


7






(6-)CF


3






O
















OCH


3















1207




—




O




C


3


H


7


-i




(6-)CF


3






O
















OCH


3















1208




—




O




CH


3






(6-)CF


3






O




CH


2


CH═CH


2






OC


3


H


7








1209




—




O




C


2


H


5






(6-)CF


3






O




CH


2


CH═CH


2






OC


3


H


7








1210




—




O




CH


3






(6-)CF


3






O




CH


3






OCH


2


C


4


H


9


-t






1211




—




O




C


2


H


5






(6-)CF


3






O




CH


3






OCH


2


C


4


H


9


-t






1212




—




O




C


3


H


7






(6-)CF


3






O




CH


3






OCH


2


C


4


H


9


-t






1213




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






OCH


2


C


4


H


9


-t






1214




—




O




CH


3






(6-)CF


3






O




CH


3






OCH


2


CCl


3








1215




—




O




C


2


H


5






(6-)CF


3






O




CH


3






OCH


2


CCl


3








1216




—




O




C


3


H


7






(6-)CF


3






O




CH


3






OCH


2


CCl


3








1217




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






OCH


2


CCl


3















1218




—




O




CH


3






(6-)CF


3






O
















CH═CHCH


3















1219




—




O




C


2


H


5






(6-)CF


3






O
















CH═CHCH


3















1220




—




O




CH


3






(4-)CH


3






O




CH


3






OCH


3








1221




—




O




CH


3






(4-)CH


3






O




CH


3






OC


2


H


5















1222




—




O




CH


3






(4-)CH


3






O
















OC


2


H


5















1223




—




O




CH


3






(4-)CH


3






O
















OC


3


H


7















1224




—




O




CH


3






(4-)CH


3






O




CH


3






OC


3


H


7















1225




—




O




CH


3






(4-)CH


3






O
















OCH


3















1226




—




O




CH


3






(6-)CF


3






O




CH


3






OCH


2


C


6


H


5















1227




—




O




CH


3






(6-)CF


3






O
















CH═CHCH


3















1228




—




O




CH


3






(6-)CF


3






O




CH


3






CH


2


CH


2


OCH


3








1229




—




O




C


2


H


5






(6-)CF


3






O




CH


3






CH


2


CH


2


OCH


3















1230




—




O




C


2


H


5






(6-)CF


3






O
















CH═CHCH


3















1231




—




O




C


3


H


7






(6-)CF


3






O
















CH═CHCH


3















1232




—




O




C


3


H


7


-i




(6-)CF


3






O




CH


3






CH


2


CH


2


OCH


3















1233




—




O




C


3


H


7


-i




(6-)CF


3






O
















CH═CHCH


3















1234




—




S




CH


3






(6-)CH


3






O
















OC


3


H


7


-i













1235




—




S




CH


3






(6-)CH


3






O




CH


3






OCH


2


CF


3








1236




—




S




CH


3






(6-)CH


3






O




CH


3






OC


3


H


7















1237




—




S




CH


3






(6-)CH


3






O
















OCH


3















1238




—




S




C


2


H


5






(6-)CH


3






O
















OC


3


H


7


-i













1239




—




S




C


2


H


5






(6-)CH


3






O




CH


3






OCH


2


CF


3








1240




—




S




C


2


H


5






(6-)CH


3






O




CH


3






OC


3


H


7















1241




—




S




C


2


H


5






(6-)CH


3






O
















OCH


3















1242




—




S




C


2


H


5






(6-)CH


3






O
















OCH


2


CF


3















1243




—




S




CH


3






(6-)CH


3






O

























1244




—




S




C


2


H


5






(6-)CH


3






O

























1245




—




S




C


3


H


7






(6-)CH


3






O

























1246




—




S




C


3


H


7


-i




(6-)CH


3






O

























1247




—




O




CH


3






(6-)CF


3






O
















OCH


3















1248




—




O




CH


2


CH


2


F




(6-)CF


3






O




CH


3






OCH


3








1249




—




O




CH


2


CH


2


F




(6-)CF


3






O




CH


3






OC


2


H


5















1250




—




O




CH


2


CH


2


F




(6-)CF


3






O
















OC


2


H


5















1251




—




O




CH


2


CH


2


F




(6-)CF


3






O




CH


3






OC


3


H


7








1252




—




O




CH


2


CH


2


F




(6-)CF


3






O




CH


3






OC


3


H


7


-i













1253




—




O




CH


2


CH


2


F




(6-)CF


3






O
















OC


3


H


7















1254




—




O




CH


2


CH


2


F




(6-)CF


3






O
















OC


3


H


7


-i













1255




—




O




CH


2


CH


2


F




(6-)CF


3






O

























1256




—




O




CH


3






(6-)C


2


H


5






O




CH


3






CH


2


OCH


3






124






1257




—




O




CH


3






(6-)C


2


H


5






O




CH


3






OCH


2


CF


3






156






1258




—




O




CH


3






(6-)C


2


H


5






O




CH


3






SC≡CH




147






1259




—




O




CH


3






(6-)C


2


H


5






O




CH


3






CH(CH


3


)


2






113






1260




—




O




CH


3






(6-)C


2


H


5






O




CH


3






CH(CH


3


)


2






125













1261




—




O




CH


3






(6-)C


2


H


5






O
















Br




154













1262




—




O




CH


3






(6-)C


2


H


5






O




C


2


H


5






OC


2


H


5






>250






1263




—




O




CH


3






(6-)C


2


H


5






O




CH


3






OC


3


H


7






200













1264




—




O




CH


3






(6-)C


2


H


5






O
















OC


2


H


5






178













1265




—




O




CH


3






(6-)Br




O




CH


3






OC


2


H


5






228






1266




—




O




C


2


H


5






(6-)C


2


H


5






O




C


2


H


5






OC


2


H


5








1267




—




O




C


2


H


5






(6-)C


2


H


5






O




CH


3






OC


3


H


7








1268




—




O




CH(CH


3


)


2






(6-)C


2


H


5






O




C


2


H


5






OC


2


H


5








1269




—




O




CH(CH


3


)


2






(6-)C


2


H


5






O




CH


3






OC


3


H


7








1270




—




O




C


2


H


5






(6-)C


2


H


5






O




CH


3






CH


2


OCH


3








1271




—




O




C


2


H


5






(6-)C


2


H


5






O




CH


3






OCH


2


CF


3








1272




—




O




CH(CH


3


)


2






(6-)C


2


H


5






O




CH


3






CH


2


OCH


3








1273




—




O




CH(CH


3


)


2






(6-)C


2


H


5






O




CH


3






OCH


2


CF


3








1274




—




O




CF


3






(6-)Br




O




CH


3






OC


2


H


5








1275




—




O




C


2


H


5






(6-)C


2


H


5






O




CH


3






OCH(CH


3


)


2















1276




—




O




C


2


H


5






(6-)C


2


H


5






O
















OC


2


H


5















1277




—




O




C


2


H


5






(6-)C


2


H


5






O
















CH


2


OCH


3















1278




—




O




CH(CH


3


)


2






(6-)C


2


H


5






O




CH


3






OCH(CH


3


)


2








1279




—




O




CH(CH


3


)


2






(6-)C


2


H


5






O




OC


2


H


5















1280




—




O




CH(CH


3


)


2






(6-)C


2


H


5






O
















CH


2


OCH


3















1281




—




O




C


3


H


7






(6-)Br




O




CH


3






OC


2


H


5








1282




—




O




C


2


H


5






(6-)C


2


H


5






O




CH


3






OCH


3








1283




—




O




C


2


H


5






(6-)F




O




CH


3






OC


2


H


5






165






1284




—




O




CH


3






(6-)F




O




CH


3






OC


2


H


5






211






1285




—




O




CH


3






(6-)CN




O




CH


3






OC


2


H


5






255






1286




—




O




CH


3






(6-)CN




O




CH


3






OC


2


H


5








1287




—




O




CH


3






(6-)CN




O




CH


3






C


2


H


5






162






1288




—




O




CH


3






(6-)CN




O




CH


3






SCH


3






268






1289




—




O




CH


3






(6-)CN




O




CH


3






OCH


3






242






1290




—




O




CH


3






(6-)CH(CH


3


)


2






O




CH


3






OCH


3






183






1291




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O




CH


3






CH


3






283






1292




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O




CH


3






OCH


3






227






1293




—




O




CH


3






(6-)F




O




CH


3






OC


2


H


5








1294




—




O




CH


3






(6-)F




O




CH


3






C


2


H


5






156






1295




—




O




CH


3






(6-)F




O




CH


3






SCH


3






179






1296




—




O




CH


3






(6-)F




O




CH


3






CH


3






217













1297




—




O




CH


3






(6-)F




O
















OCH(CH


3


)


2






147













1298




—




O




CH(CH


3


)


2






(6-)F




O




CH


3






OC


2


H


5






165






1299




—




O




CH(CH


3


)


2






(6-)F




O




CH


3






C


2


H


5






113






1300




—




O




CH(CH


3


)


2






(6-)F




O




CH


3






OCH


3






149













1301




—




O




CH(CH


3


)


2






(6-)F




O
















CH


3






147













1302




—




O




CH(CH


3


)


2






(6-)F




O
















OCH(CH


3


)


2






127













1303




—




O




C


3


H


7






(6-)F




O




CH


3






OC


2


H


5






139






1304




—




O




C


3


H


7






(6-)F




O




CH


3






C


2


H


5






116






1305




—




O




C


3


H


7






(6-)F




O




CH


3






OCH


3






129













1306




—




O




C


3


H


7






(6-)F




O
















CH


3






120













1307




—




O




C


3


H


7






(6-)F




O




CH


3






OC


2


H


5






>160






1308




—




O




C


2


H


5






(6-)CH


3






O




CH


3






OC


4


H


9






114













1309




—




O




C


2


H


5






(6-)CH


3






O
















OC


4


H


9






126













1310




—




O




C


2


H


5






(6-)CH


3






O




CH


3






OCH


2


CH(CH


3


)


2






144













1311




—




O




C


2


H


5






(6-)CH


3






O
















OCH


2


CH(CH


3


)


2






145













1312




—




O




C


2


H


5






(6-)CH


3






O
















OCH


2


CF


3






133













1313




—




O




C


2


H


5






(6-)CH


3






O
















OCH


3






181













1314




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O




CH


3






OC


4


H


9






170













1315




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O
















OC


4


H


9






129













1316




—




O




CH


3






(6-)CH


3






O




CH


3






OCH


2


CH(CH


3


)


2






137













1317




—




O




CH


3






(6-)CH


3






O
















OCH


2


CH(CH


3


)


2






165













1318




—




O




CH


3






(6-)CH


3






O




CH


3


















150













1319




—




O




CH


3






(6-)CH


3






O




























186













1320




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O




CH


3






OCH


2


CH(CH


3


)


2






163













1321




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O




CH


3


















134













1322




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O




























187













1323




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O
















CH


3






158













1324




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O
















C


2


H


5






172













1325




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O
















C


3


H


7






142













1326




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O
















OCH


2


CF


3






150













1327




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O
















OCH


3






137













1328




—




O




C


2


H


5






(6-)CH(CH


3


)


2






O
















CH(CH


3


)


2






168













1329




—




O




C


2


H


5






(6-)CH


3






O
















SCH


3






167













1330




—




O




CH(CH


3


)


2






(6-)CH


3






O
















SCH


3






167













1331




—




O




C


2


H


5






(6-)CH


3






O
















SC


2


H


5






150













1332




—




O




CH(CH


3


)


2






(6-)CH


3






O
















SC


2


H


5






150













1333




—




O




C


3


H


7






(6-)CH


3






O
















SC


2


H


5






140













1334




—




O




C


2


H


5






(6-)F




O




CH


3






SCH


3






165






1335




—




O




C


2


H


5






(6-)F




O




CH


3






C


2


H


5






135






1336




—




O




C


2


H


5






(6-)F




O




CH


3






OCH


3






168






1337




—




O




C


2


H


5






(6-)F




O




CH


3






CH


3






140













1338




—




O




C


2


H


5






(6-)F




O
















OCH


3






138













1339




—




O




C


3


H


7






(6-)OC


3


H


7






O




CH


3






OC


2


H


5








1340




—




O




C


3


H


7






(6-)OC


3


H


7






O




CH


3






OC


2


H


5








1341




—




O




C


3


H


7






(6-)OCH


3






O




CH


3






OC


2


H


5








1342




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O




CH


3






OC


2


H


5








1343




—




O




C


2


H


5






(6-)OC


2


H


5






O




CH


3






OC


2


H


5








1344




—




O




C


4


H


9






(6-)OC


4


H


9






O




CH


3






OC


2


H


5








1345




—




O




CH(CH


3


)C


2


H


5






(6-)OCH


3






O




CH


3






CH


3






157






1346




—




O




CH(CH


3


)C


2


H


5






(6-)OCH


3






O




CH


3






C


3


H


7






86






1347




—




O




CH


2


CH(CH


3


)


2






(6-)OC


2


H


5






O




CH


3






Br




108






1348




—




O




CH


2


CH(CH


3


)


2






(6-)OC


2


H


5






O




CH


3






CH


3






82













1349




—




O




CH


2


CH(CH


3


)


2






(6-)OC


2


H


5






O
















Br




120













1350




—




O




C


3


H


7






(6-)OCH


3






O
















OCH(CH


3


)


2






141













1351




—




O




C


3


H


7






(6-)OCH


3






O
















OC


3


H


7






102













1352




—




O




C


2


H


5






(6-)OC


2


H


5






O
















OCH(CH


3


)


2






110













1353




—




O




C


2


H


5






(6-)OC


2


H


5






O
















OC


3


H


7






132













1354




—




O




C


2


H


5






(6-)OC


2


H


5






O
















OCH


2


CF


3






114













1355




—




O




CH(CH


3


)


2






(6-)OCH


3






O
















OCH(CH


3


)


2






172













1356




—




O




CH(CH


3


)


2






(6-)OCH


3






O
















OC


3


H


7






156













1357




—




O




C


3


H


7






(6-)OC


3


H


7






O
















OCH(CH


3


)


2






141













1358




—




O




C


2


H


5






(6-)OCH


3






O
















OC


3


H


7






134













1359




—




O




C


2


H


5






(6-)OC


3


H


7






O
















OCH(CH


3


)


2






132













1360




—




O




CH(CH


3


)


2






(6-)OC


2


H


5






O
















OCH(CH


3


)


2






147













1361




—




O




(CH


2


)


2


OC


3


H


7






(6-)OCH


3






O
















OCH


2


CF


3






134













1362




—




O




CH


2


CH(CH


3


)


2






(6-)OC


2


H


5






O
















OCH(CH


3


)


2






96













1363




—




O




C


3


H


7






(6-)OC


2


H


5






O
















OCH


3






120













1364




—




O




CH(CH


3


)


2






(6-)OC


2


H


5






O
















OCH


3






108













1365




—




O




CH(CH


3


)


2






(6-)OC


2


H


5






O
















OC


3


H


7






127













1366




—




O




C


4


H


9






(6-)OC


4


H


9






O
















OCH


3






118













1367




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O
















154













1368




—




O




C


3


H


7






(6-)OCH


3






O
















CH


3






122













1369




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O
















CH


3






134













1370




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O




CH


3






CH(CH


3


)C


2


H


5






97






1371




—




O




C


3


H


7






(6-)OCH


3






O




CH


3






CH(CH


3


)


2






76






1372




—




O




C


3


H


7






(6-)OCH


3






O




CH


3






SC


2


H


5






91













1373




—




O




C


2


H


5






(6-)OC


2


H


5






O




























102













1374




—




O




C


2


H


5






(6-)OC


2


H


5






O
















CH


3






125













1375




—




O




C


2


H


5






(6-)OC


2


H


5






O
















C


2


H


5






112













1376




—




O




C


2


H


5






(6-)OC


2


H


5






O
















C


3


H


7






113













1377




—




O




C


2


H


5






(6-)OC


2


H


5






O




CH


3






CH(CH


3


)C


2


H


5






100






1378




—




O




C


2


H


5






(6-)OC


2


H


5






O




CH


3






CH(CH


3


)


2






118






1379




—




O




C


2


H


5






(6-)OC


2


H


5






O




CH


3






C


4


H


9






81






1380




—




O




C


2


H


5






(6-)OC


2


H


5






O




CH


3






CH


2


CH(CH


3


)


2






93






1381




—




O




C


3


H


7






(6-)OCH


3






O




CH


3






CH(CH


3


)C


2


H


5






79






1382




—




O




C


3


H


7






(6-)OCH


3






O




CH


3






CH


2


CH(CH


3


)


2






83













1383




—




O




C


2


H


5






(6-)OC


2


H


5






O
















OC


2


H


5






67













1384




—




O




C


2


H


5






(6-)OC


2


H


5






O
















C


3


H


7






105













1385




—




O




C


2


H


5






(6-)OC


2


H


5






O
















OCH(CH


3


)


2






97













1386




—




O




C


3


H


7






(6-)OCH


3






O
















OCH(CH


3


)


2






82













1387




—




O




C


2


H


5






(6-)OC


2


H


5






O
















CH


2


CH(CH


3


)


2






103













1388




—




O




C


3


H


7






(6-)OCH


3






O
















CH


2


CH(CH


3


)


2






116













1389




—




O




C


2


H


5






(6-)OC


2


H


5






O
















OCH


3






104













1390




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O
















OCH


3






127













1391




—




O




C


3


H


7






(6-)OCH


3






O
















OCH


3






93













1392




—




O




C


2


H


5






(6-)OC


2


H


5






O
















OC


3


H


7






107













1393




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O
















OC


3


H


7






130













1394




—




O




C


3


H


7






(6-)OCH


3






O
















OC


3


H


7






80













1395




—




O




C


2


H


5






(6-)OC


2


H


5






O
















C


4


H


9






77













1396




—




O




C


3


H


7






(6-)CH


3






O
















C


4


H


9






107













1397




—




O




C


2


H


5






(6-)OC


2


H


5






O




























107













1398




—




O




C


3


H


7






(6-)OCH


3






O




























85













1399




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O
















C


4


H


9






89













1400




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O




























100













1401




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O




CH


3






CH(CH


3


)


2






118






1402




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O




CH


3






C


4


H


9






82






1403




—




O




C


3


H


7






(6-)OCH


3






O




CH


3






C


4


H


9






75













1404




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O
















CH


2


CH(CH


3


)


2






95













1405




—




O




C


2


H


5






(6-)OC


2


H


5






O




CH


3






C(CH


3


)═CH


2






118






1406




—




O




CH(CH


3


)


2






(6-)OCH(CH


3


)


2






O




CH


3






C(CH


3


)═CH


2






103






1407




—




O




C


3


H


7






(6-)OCH


3






O




CH


3






C(CH


3


)═CH


2






92






1408




—




O




C


3


H


7






(6-)OH




O




CH


3






OC


2


H


5






152






1409




—




O




C


3


H


7






(6-)OH




O




CH


3






OCH


3






137






1410




—




O




C


3


H


7






(6-)OH




O




CH


3






OC


3


H


7






88






1411




—




O




C


3


H


7






(6-)OH




O




CH


3






OCH(CH


3


)


2






125






1412




—




O




CH


3






(6-)OH




O




CH


3






OCH


3






148






1413




—




O




CH


3






(6-)OH




O




CH


3






OC


2


H


5






144






1414




—




O




CH


3






(6-)OH




O




CH


3






OC


3


H


7






128






1415




—




O




CH


3






(6-)OH




O




CH


3






OCH(CH


3


)


2






158













1416




—




O




CH


3






(6-)OH




O
















OCH(CH


3


)


2






137













1417




—




O




CH


3






(6-)OH




O
















OC


2


H


5






125













1418




—




O




CH


3






(6-)OH




O




C


2


H


5






OCH


3






137






1419




—




O




CH


3






(6-)OH




O




CH


3






SCH


3






130






1420




—




O




CH


3






(6-)OH




O




CH


3






C


2


H


5






40






1421




—




O




C


3


H


7






(6-)OCHF


2






O




CH


3






OC


2


H


5






230






1422




—




O




CH


3






(6-)OCHF


2






O




CH


3






OC


2


H


5






202






1423




—




O




CH


3






(6-)OCHF


2






O




CH


3






SCH


3






202






1424




—




O




CH


3






(6-)OCHF


2






O




CH


3






C


2


H


5






98






1425




—




S




C


3


H


7






(6-)OCHF


2






O




CH


3






OC


3


H


7






198













1426




—




O




C


3


H


7






(6-)OCHF


2






O
















OC


2


H


5






124













1427




—




O




CHF


2






(6-)OCRF


2






O




CH


3






OCH


3






145






1428




—




O




CHF


2






(6-)OCHF


2






O




CH


3






OC


2


H


5






177






1429




—




O




CHF


2






(6-)OCHF


2






O




CH


3






OC


2


H


5






>220













1430




—




O




CHF


2






(6-)OCHF


2






O
















OC


2


H


5






148













1431




—




O




CHF


2






(6-)OCHF


2






O




CH


3






C


2


H


5






123






1432




—




O




CHF


2






(6-)OCHF


2






O




CH


3






SCH


3






133













1433




—




O




CHF


2






(6-)OCHF


2






O
















CH(CH


3


)


2






130













1434




—




O




C


3


H


7






(6-)OCHF


2






O




CH


3






OCH(CH


3


)


2















1435




—




O




CH


2


CH═CH


2






(6-)OC


2


H


5






O
















OC


2


H


5






84













1436




—




O




CH


2


CH═CH


2






(6-)OC


2


H


5






O
















OCH


3






120













1437




—




O




CH


2


CH═CH


2






(6-)OC


2


H


5






O




CH


3






OCH(CH


3


)


2






133






1438




—




O




CH


2


CH═CH


2






(6-)OC


2


H


5






O




CH


3






C


2


H


5






137






1439




—




O




CH


2


CH═CH


2






(6-)OC


2


H


5






O




CH


3






OC


2


H


5






100






1440




—




O




CH


2


CH═CH


2






(6-)OC


2


H


5






O




CH


3






OCH


3






94






1441




—




O




CH


3






(6-)OCH


3






O




CH


3






N(CH


3


)


2






168






1442




—




O




CH


3






(6-)C


2


H


5






O




CH


3






N(CH


3


)


2






172






1443




—




O




CF


3






(6-)C


2


H


5






O




CH


3






N(CH


3


)


2






128






1444




—




O




CF


3






(6-)CH


3






O




CH


3






OC


2


H


5






224






1445




—




O




CH


3






(6-)OCH


3






O




OCH


3






SCH


3






157






1446




—




O




CH


3






(6-)OCH


3






O




OCH


3






SC


2


H


5






149






1447




—




O




CH


3






(6-)OCH


3






O




OC


2


H


5






SCH


3






147






1448




—




O




CH


3






(6-)OCH


3






O




OC


2


H


5






SC


2


H


5






124






1449




—




O




CH


3






(6-)C


2


H


5






O




NH


2






CH


3






204






1450




—




O




C


2


H


5






(6-)OC


2


H


5






O




OCH


3






SCH


3






130






1451




—




O




C


2


H


5






(6-)OC


2


H


5






O




OCH


3






SC


2


H


5






112






1452




—




O




C


2


H


5






(6-)OC


2


H


5






O




OC


2


H


5






SCH


3






113






1453




—




O




OC


2


H


5






(6-)OC


2


H


5






O




OC


2


H


5






SC


2


H


5






157






1454




—




O




CF


2


CF


2


H




(6-)CH


3






O




CH


3






OCH


3






127






1455




—




O




CF


2


CF


2


H




(6-)CH


3






O




CH


3






OC


2


H


5






156






1456




—




O




CF


2


CF


2


H




(6-)CH


3






O




CH


3






OC


3


H


7






132






1457




—




O




CF


2


CF


2


H




(6-)CH


3






O




CH


3






OCH(CH


3


)


2






172






1458




—




O




CF


2


CF


2


H




(6-)CH


3






O




CH


3






C


3


H


7






90






1459




—




O




CF


3






(6-)C


2


H


5






O




CH


3






OC


3


H


7






185






1460




—




O




CF


3






(6-)C


2


H


5






O




CH


3






OCH(CH


3


)


2






192






1461




—




O




CF


3






(6-)C


2


H


5






O




CH


3






OCH


2


CF


3






159













1462




—




O




CF


3






(6-)C


2


H


5






O




CH


3


















192













1463




—




O




CF


3






(6-)C


2


H


5






O




CH


3






CH


3






>270






1464




—




O




CF


3






(6-)C


2


H


5






O




CH


3






C


2


H


5






259






1465




—




O




CF


3






(6-)C


2


H


5






O




CH


3






C


3


H


7






241






1466




—




O




CF


3






(6-)C


2


H


5






O




CH


3






SCH


3






174













1467




—




O




CF


3






(6-)C


2


H


5






O
















OCH


3






165













1468




—




O




CF


3






(6-)C


2


H


5






O
















OC


2


H


5






145













1469




—




O




CF


3






(6-)C


2


H


5






O
















OC


3


H


7






196













1470




—




O




CF


3






(6-)C


2


H


5






O
















OCH(CH


3


)


2






170













1471




—




O




CF


3






(6-)C


2


H


5






O
















OCH


2


CF


3






183













1472




—




O




CF


3






(6-)C


2


H


5






O




























154













1473




—




O




CF


3






(6-)C


2


H


5






O




CH


3


















188













1474




—




O




CF


3






(6-)C


2


H


5






O
















C


2


H


5






163













1475




—




O




CF


3






(6-)C


2


H


5






O
















C


3


H


7






190













1476




—




O




CF


3






(6-)C


2


H


5






O
















SCH


3






159













1477




—




O




CF


3






(6-)C


2


H


5






O
















CH


3






151













1478




—




O




CF


3






(6-)C


2


H


5






O
















C


3


H


7






163













1479




—




O




CF


3






(6-)C


2


H


5






O
















CH═CH(CH


3


)




176













1480




—




O




CF


3






(6-)C


2


H


5






O




























156













1481




—




O




CF


3






(6-)C


2


H


5






O
















CH


2


OCH


3






146













1482




—




O




CH


3






(6-)C


2


H


5






O




OCH


3






SCH


3






149






1483




—




O




CH


3






(6-)C


2


H


5






O




OCH


3






SC


2


H


5






137






1484




—




O




CH


3






(6-)C


2


H


5






O




OC


2


H


5






SCH


3






115






1485




—




O




CH


3






(6-)C


2


H


5






O




OC


2


H


5






SC


2


H


5






99













1486




—




O




CH(CH


3


)


2






(6-)CH


3






O
















CH(CH


3


)


2






132













1487




—




O




CF


3






(6-)C


2


H


5






O
















CH(CH


3


)


2






108













1488




—




O




CH


3






(6-)C


2


H


5






O
















CH(CH


3


)


2






151













1489




—




O




CH


3






(6-)OCH


3






O
















CH(CH


3


)


2






163













1490




—




O




C


2


H


5






(6-)OC


2


H


5






O
















CH(CH


3


)


2






111













1491




—




O




CH


3






(6-)C


2


H


5






O




CH


3


















118













1492




—




O




CH


3






(6-)C


2


H


5






O




























147













1493




—




O




CF


3


CF


3


H




(6-)CH


3






O
















OCH


3






160













1494




—




O




CF


3


CF


3


H




(6-)CH


3






O
















OC


2


H


5






155













1495




—




O




CF


3


CF


3


H




(6-)CH


3






O
















OCH(CH


3


)


2






166













1496




—




O




CH


2


CF


3






(6-)CH


3






O




CH


3






OCH


3






149






1497




—




O




CH


2


CF


3






(6-)CH


3






O




CH


3






OC


2


H


5






230






1498




—




O




CH


2


CF


3






(6-)CH


3






O




CH


3






OC


3


H


7






238






1499




—




O




CH


2


CF


3






(6-)CH


3






O




CH


3






OCH(CH


3


)


2






89













1500




—




O




CH


2


CF


3






(6-)CH


3






O




CH


3


















134













1501




—




O




CH


2


CF


3






(6-)CH


3






O
















OCH


3






189













1502




—




O




CH


2


CF


3






(6-)CH


3






O
















OC


2


H


5






129













1503




—




O




CH


2


CF


3






(6-)CH


3






O
















OC


3


H


7






126













1504




—




O




CH


2


CF


3






(6-)CH


3






O
















OCH(CH


3


)


2






161













1505




—




O




CH


2


CF


3






(6-)CH


3






O




























128













1506




—




O




CH


2


CF


3






(6-)CH


3






O




CH


3






C


3


H


7






148













1507




—




O




CH


3






(6-)C


2


H


5






O




CH


3


















144













1508




—




O




CH


3






(6-)C


2


H


5






O




CH


3






CH═CH(CH


3


)




138













1509




—




O




CH


3






(6-)C


2


H


5






O




CH


3


















160













1510




—




O




CH


3






(6-)C


2


H


5






O
















CH


3






168













1511




—




O




CH


3






(6-)C


2


H


5






O
















C


2


H


5






143













1512




—




O




CH


3






(6-)C


2


H


5






O
















C


3


H


7






140













1513




—




O




CH


3






(6-)C


2


H


5






O




























170













1514




—




O




CH


3






(6-)C


2


H


5






O
















CH═CH(CH


3


)




127













1515




—




O




CH


3






(6-)C


2


H


5






O
















N(CH


3


)


2






214













1516




—




O




CH


3






(6-)C


2


H


5






O
















SCH


3






167













1517




—




O




CH


3






(6-)C


2


H


5






O
















SC


2


H


5






137













1518




—




O




CH


3






(6-)C


2


H


5






O
















OCH


3






165













1519




—




O




CH


3






(6-)C


2


H


5






O
















OCH


2


CF


3






163













1520




—




O




CH


3






(6-)C


2


H


5






O
















OC


3


H


7






125













1521




—




O




CH


3






(6-)C


2


H


5






O




























133













1522




—




O




CH


3






(6-)C


2


H


5






O




CH


3


















136













1523




—




O




CF


2


H




(6-)C


2


H


5






O




CH


3






OCH


3






121






1524




—




O




CF


2


H




(6-)C


2


H


5






O




CH


3






OC


2


H


5






150






1525




—




O




CF


2


H




(6-)C


2


H


5






O




CH


3






OC


3


H


7






119






1526




—




O




CF


2


H




(6-)C


2


H


5






O




CH


3






OCH(CH


3


)


2






122













1527




—




O




CF


2


H




(6-)C


2


H


5






O




CH


3


















146













1528




—




O




CF


2


H




(6-)C


2


H


5






O
















OCH


3






163













1529




—




O




CF


2


H




(6-)C


2


H


5






O
















OC


2


H


5






140













1530




—




O




CF


2


H




(6-)C


2


H


5






O
















OC


3


H


7






129













1531




—




O




CF


2


H




(6-)C


2


H


5






O
















OCH(CH


3


)


2






118













1532




—




O




CF


2


H




(6-)C


2


H


5






O




























133













1533




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3






CH


3






290






1534




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3






C


3


H


7






274






1535




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




OC


2


H


5






C


2


H


5






118






1536




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3






N(CH


3


)


2






170






1537




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3






SCH


3






168






1538




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3






OCH


3






166






1539




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3






OC


2


H


5






140






1540




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3






OC


3


H


7






138






1541




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3






OCH(CH


3


)


2






136













1542




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3


















139













1543




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O
















OCH


3






156













1544




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O
















OC


2


H


5






138













1545




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O
















OC


3


H


7






125













1546




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O
















OCH(CH


3


)


2






140













1547




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




























158













1548




—




O




CH


3






(6-)C


2


H


5






O
















C


5


H


9






149













1549




—




O




CH


3






(6-)C


2


H


5






O




CH


3






C


5


H


9






118






1550




—




O




CF


3






(6-)C


3


H


7






O




CH


3






OCH


3






94






1551




—




O




CF


3






(6-)C


3


H


7






O




CH


3






OC


2


H


5






175






1552




—




O




CF


3






(6-)C


3


H


7






O




CH


3






OC


3


H


7






166






1553




—




O




CF


3






(6-)C


3


H


7






O




CH


3






OCH(CH


3


)


2






164






1554




—




O




CF


3






(6-)C


3


H


7






O




CH


3






OCH


2


CF


3






221













1555




—




O




CF


3






(6-)C


3


H


7






O




CH


3


















189













1556




—




O




CF


3






(6-)C


3


H


7






O
















OCH


3






182













1557




—




O




CF


3






(6-)C


3


H


7






O
















OCH


2


CH


3






134













1558




—




O




CF


3






(6-)C


3


H


7






O
















OC


3


H


7






207













1559




—




O




CF


3






(6-)C


3


H


7






O
















OCH(CH


3


)


2






148













1560




—




O




CF


3






(6-)C


3


H


7






O
















OCH


2


CF


3






204













1561




—




O




CF


3






(6-)C


3


H


7






O




























186

























1562




—




O




CH


3






(6-)C


2


H


5






O




CH


2


CH


2


OCH


2






163






1563




—




O




CH


3






(6-)C


2


H


5






O




CH


2


CH


2


CH


2


OCH


2






191


























1564




—




O




CF


3






(6-)CH


3






O
















OCH


3






197













1565




—




O




CH


2


CF


2


H




(6-)CH


3






O




CH


3






OCH


3






231






1566




—




O




CH


2


CF


2


H




(6-)C


2


H


5






O




CH


3






OCH


3






174













1567




—




O




CH


2


CF


2


H




(6-)C


2


H


5






O
















OCH


3






160




















1568




—




O




CH


2


CF


2


H




(6-)C


2


H


5






O
















OCH(CH


3


)


2






162













1569




—




O




CH


2


CF


2


H




(6-)C


2


H


5






O




CH


3






CH


3






>250






1570




—




O




CH


2


CF


2


H




(6-)CH


3






O




CH


3






OCH


2


CF


3






117













1571




—




O




CH


2


CF


2


H




(6-)CH


3






O




CH


3


















128













1572




—




O




CH


2


CF


2


H




(6-)CH


3






O




























124













1573




—




O




CH


2


CF


2


H




(6-)CH


3






O




CH


3






C


2


H


5






137






1574




—




O




CH


2


CF


2


H




(6-)CH


3






O




CH


3






C


3


H


7






139













1575




—




O




CH


2


CF


2


H




(6-)CH


3






O




CH


3


















150













1576




—




O




CH


2


CF


2


H




(6-)CH


3






O




CH


3






CH


2


OCH


3






114






1577




—




O




CH


2


CF


2


H




(6-)CH


3






O




CH


3






SCH


3






155






1578




—




O




CH


2


CF


2


H




(6-)C


3


H


7






O




CH


3






CH


3






290






1579




—




O




CH


2


CF


2


H




(6-)CH


3






O




CH


3






N(CH


3


)


2






116






1580




—




O




CH


2


CF


2


H




(6-)CH


3






O




OC


2


H


5






C


2


H


5






125













1581




—




O




CH


2


CF


2


H




(6-)CH


3






O
















CH


3






137













1582




—




O




CH


2


CF


2


H




(6-)CH


3






O
















OC


2


H


5






99













1583




—




O




CH


2


CF


2


H




(6-)CH


3






O
















OC


3


H


7






130













1584




—




O




CH


2


CF


2


H




(6-)C


2


H


5






O




CH


3






CC


2


H


5






147






1585




—




O




CH


2


CF


2


H




(6-)C


2


H


5






O




CH


3






OCH(CH


3


)


2






151






1586




—




O




CH


3






(6-)C


2


H


5






O




CH


3






N(CH


3


)


2






199






1587




—




O




CF


3






(6-)C


2


H


5






O




CH


3






CH═CH(CH


3


)




128






1588




—




O




CF


3






(6-)C


2


H


5






O




CH


3






CH


2


OCH


3






101













1589




—




O




CF


3






(6-)C


2


H


5






O
















N(CH


3


)


2






154













1590




—




O




CF


3






(6-)C


2


H


5






O
















SC


2


H


5






143













1591




—




O




CF


3






(6-)C


2


H


5






O




CH


3






SC


2


H


5






113






1592




—




O




CF


3






(6-)C


2


H


5






O




OC


2


H


5






C


2


H


5






122






1593




—




O




CF


3






(6-)C


2


H


5






O




OC


2


H


5






SC


2


H


5






133






1594




—




O




CF


3






(6-)C


2


H


5






O




CH


3






OC


6


H


5






193






1595




—




O




CH


2


CH


2


F




(6-)CH


3






O




CH


3






C


2


H


5






109













1596




—




O




CH


2


CH


2


F




(6-)CH


3






O




CH


3


















157













1597




—




O




CH


2


CH


2


F




(6-)CH


3






O




CH


3






CH


2


OCH


3






106






1598




—




O




CH


2


CH


2


F




(6-)CH


3






O




CH


3






SCH


3






135






1599




—




O




CH


2


CH


2


F




(6-)CH


3






O




CH


3






N(CH


3


)


2






141






1600




—




O




CH


2


CH


2


F




(6-)CH


3






O




OC


2


H


5






C


2


H


5






129













1601




—




O




CH


2


CH


2


F




(6-)CH


3






O
















CH


3






169













1602




—




O




CH


2


CH


2


F




(6-)CH


3






O
















OC


2


H


5






125













1603




—




O




CH


2


CH


2


F




(6-)CH


3






O
















OC


3


H


7






117













1604




—




O




CH


2


CH


2


F




(6-)CH


3






O




CH


3


















145













1605




—




O




CH


2


CH


2


F




(6-)CH


3






O




























118













1606




—




O




CH


2


CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






OCH


3






127






1607




—




O




CH


2


CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






OCH(CH


3


)


2






155













1608




—




O




CH


2


CH


2


CH


2


F




(6-)C


3


H


7






O
















OCH


3






106













1609




—




O




CH


2


CH


2


CH


2


F




(6-)C


3


H


7






O
















OCH(CH


3


)


2






138













1610




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3


















157













1611




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O




CH


3






CH


2


OCH


3






101













1612




—




O




CH


2


CH


2


F




(6-)C


2


H


5






O
















CH


3






147













1613




—




O




CH


2


CH


2


F




(6-)CH


3






O




CH


3






C


3


H


7






280






1614




—




O




CH


2


CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






CH


3






302






1615




—




O




CH


2


CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






C


3


H


7






261






1616




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






C


3


H


7






108






1617




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






OCH


3






158






1618




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






OC


2


H


5






152






1619




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






OCH(CH


3


)


2






164













1620




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O
















OCH


3






137













1621




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O
















OC


2


H


5






117













1622




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O
















OCH(CH


3


)


2






158













1623




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






N(CH


3


)


2






147






1624




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O




OC


2


H


5






C


2


H


5






237






1625




—




O




CH


2


CH


2


F




(6-)C


3


H


7






O




CH


3






SCH


3






130






1626




—




O




CHF


2






(6-)Br




O




CH


3






OCH


3






160






1627




—




O




CHF


2






(6-)Br




O




CH


3






CH


3






146






1628




—




O




CHF


2






(6-)Br




O




CH


3






C


3


H


7






127






1629




—




O




CHF


2






(6-)Br




O




CH


3






OC


2


H


5






168






1630




—




O




CHF


2






(6-)Br




O




CH


3






OCH(CH


3


)


2






126













1631




—




O




CHF


2






(6-)Br




O
















OCH


3






145













1632




—




O




CHF


2






(6-)Br




O
















OC


2


H


5






125













1633




—




O




CHF


2






(6-)Br




O
















OCH(CH


3


)


2






148













1634




—




O




CHF


2






(6-)Br




O




CH


3






N(CH


3


)


2






173






1635




—




O




CF


3






(6-)F




O




CH


3






SCH


3








1636




—




O




CF


3






(6-)F




O




CH


3






C


2


H


5








1637




—




O




CF


3






(6-)F




O




CH


3






OC


2


H


5
















The compound listed in Table 1 as Example 9 can be prepared, for example, as follows:











(Process (b))




1.4 g (0.01 mol) of 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one and 2.4 g (0.01 mol) of 2-ethoxy-6-methyl-phenytsulphonyl isocyanate are stirred at 20° C. For 15 hours in 50 ml of acetonitrile. The solvent is distilled off, the residue is stirred with diethyl ether and the precipitate is filtered off with suction.




3.3 g (85% of theory) of 5-ethoxy-4-methyl-2-(2-ethoxy-6-methyl-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 160° C.




Starting Materials of the Formula (II) or (IIa):




Example (II-1)
















64.6 g (0.26 mol) of 2-isopropoxy-6-methyl-benzenesulphochloride are stirred at 20° C. For 12 hours in 350 ml of 25% strength aqueous ammonia solution. The crystalline product is subsequently isolated by filtration with suction. 54 g (90% of theory) of 2-isopropoxy-6-methyl-benzenesulphonamide are obtained of melting point 78° C.




Example (II-2)
















A mixture of 1.9 g (10 mmol) of 2-hydroxy-6-methyl-benzenesulphonamide, 1.2 g (10 mmol) of propargyl bromide (in the form of an 80% strength solution in toluene) and 1.4 g (10 mmol) of potassium carbonate is heated under reflux for 2 hours. The mixture is then filtered, the filtrate is concentrated under a water pump vacuum, the residue is digested with petroleum ether and the crystalline product obtained from this digestion is isolated by filtration with suction.




2.1 g (93% of theory) of 6-methyl-2-propargyloxy-benzenesulphonamide are obtained of melting point 129° C.




Example (II-3)
















188 ml of a 1-molar solution of boron(III) bromide in methylene chloride are added dropwise at 20° C. with stirring to a solution of 32.3 g (0.15 mol) of 2-ethoxy-6-methylbenzenesulphonamide in 300 ml of methylene chloride, and the reaction mixture is stirred at 20° C. for 30 minutes. Then 300 ml of methanol are added dropwise at from 0° C. to 5° C. (ice cooling). After heating to 20° C., the reaction mixture is concentrated under a water pump vacuum and the residue is stirred with ethyl acetate. The solution obtained is washed with water, dried over sodium sulphate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is crystallized by stirring with petroleum ether, and the crystalline product is isolated by filtration with suction.




20.3 g (72% of theory) of 2-hydroxy-6-methyl-benzenesulphonamide are obtained of melting point 126° C.




In analogy to Examples (II-1) to (II-3) and in accordance with the general description of the preparation process according to the invention, it is also possible, for example, to prepare the compounds of the formula (II) or (IIa) listed in Table 2 below,












TABLE 2











Examples of the compounds of the formula (II)













(II)







































(position-)




Melting






Ex. No.




A




R


1






R


2






point (° C.)


















II-4




—




C


2


H


5






(6-)CH


3






104






II-5




—




n-C


3


H


7






(6-)CH


3






63






II-6




—




—CH


2


CH


2


Cl




(6-)CH


3






102






II-7




—




CH


3






(6-)CH


3






132






II-8




—




—CH


2


C


6


H


5






(6-)CH


3






131






II-9




—




—CH


2


COOCH


3






(6-)CH


3






90






II-10




—




CH


3






(6-)C


3


H


7


-n




108






II-11




—




C


2


H


5






(6-)C


3


H


7


-n




80






II-12




—




C


2


H


5






(5-)CH


3






131






II-13




—




CH


3






(6-)Cl




166






II-14




—




C


2


H


5






(6-)Cl




121






II-15




—




H




(6-)Cl




118






II-16




—




i-C


3


H


7






(6-)Cl




85






II-17




—




—CH


2


CH═CH


2






(6-)Cl




106






II-18




—




—CH


2


C≡CH




(6-)Cl




181






II-19




—




CF


3






(5-)Cl






II-20




—




CHF


2






(5-)CH


3






127






II-21




—




CHF


2






(6-)CH


3






89






II-22




—




CH


3






(5-)C(CH


3


)


3






160






II-23




—




CH


3






(5-)Cl






II-24




—




CHF


2






(4-)CH


3






153






II-25




—




—CF


2


CHFCl




(6-)CH


3






85






II-26




—




C


2


H


5






(6-)CH


2


Cl














Starting Materials of the Formula (IV):




Example (IV-1)
















21.5 g (0.1 mol) of 2-ethoxy-6-methyl-benzenesulphonamide and 10 g (0.1 mol) of n-butyl isocyanate are heated to boiling in 100 ml of chlorobenzene. At reflux temperature, phosgene is passed in for 4 hours. The clear solution is concentrated under reduced pressure and the residue is subjected to precision distillation. At a pressure of 0.8 bar and an overhead temperature of 135-140° C., 2-ethoxy-6-methyl-phenylsulphonyl isocyanate goes over and solidifies in the receiver.




7.9 g of 2-ethoxy-6-methyl-phenylsulphonyl isocyanate are obtained as a colourless product of melting point 40° C.




Starting Materials of the Formula (VI) or (VIa):




Example (VI-1)
















47.8 g (0.29 mol) of 2-isopropoxy-6-methyl-aniline are dissolved in a mixture of 87 ml of 1N hydrochloric acid and 145 ml of conc. hydrochloric acid, and the solution is cooled to −5° C. At −5° C. to 0° C., a solution of 22 g (0.32 mol) of sodium nitrite in 87 ml of water is then added dropwise with stirring and the mixture is stirred at about 0° C. for a further hour. After removal of the nitrite excess with amidosulphonic acid, the diazonium salt solution obtained is added dropwise at −5° C. to 0° C. to a saturated solution of sulphur dioxide in 175 ml of 1,2-dichloro-ethane. After about 30 minutes, 1.7 g of copper(I) chloride and 1.7 g of dodecyl-trimethylammonium bromide are added, and the reaction mixture is allowed to rise to room temperature over the course of about 60 minutes, heated to about 40° C. over a further hour, and stirred at this temperature for about 12 hours. At about 20° C., 14.2 g of a 35% strength hydrogen peroxide solution are then added and the mixture is stirred for about 30 minutes. It is subsequently stirred with 300 ml of methylene chloride, and the organic phase is separated off, washed with water, dried over sodium sulphate and filtered. The solvent is carefully removed from the filtrate by distillation under a water pump vacuum.




65.9 g (90% of theory) of 2-isopropoxy-6-methyl-benzenesulphochloride are obtained as a brownish oily residue.






1


H-NMR (CDCl


3


, TMS, δ ppm): 1.47 (d, J=6.1 Hz, 2×CH


3


); 2.68 (s, CH


3


); 4.79 (sept., J=6.1 Hz, 1H); 6.83 (d, J=7.5 Hz, 1H); 6.95 (d, J=8.4 Hz, 1H); 7.45 (pseudo t, J=8.3 Hz, 1H).




In analogy to Example (VI-1) it is also possible, for example, to prepare the compounds of the formula (VI) or (VIa) listed in Table 3 below.












TABLE 3











Examples of the compounds of the formula (VI)




















(IV)







































(position-)




Physical






Ex. No.




A




R


1






R


2






data









VI-2




—




CH


3






(6-)CH


3






Fp.: 52° C.






VI-3




—




C


2


H


5






(6-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 1,55










(t, J=6,97 Hz, CH


3


), 2,69 (s, CH


3


),










4,24 (q, J=6,97 Hz, CH


2


), 6,87 (d,










J=7,68 Hz, 1H), 6,95 (d, J=8,34 Hz,










1H), 7,46 (pseudo t, J=8,1 Hz, 1H)






VI-4




—




n-C


3


H


7






(6-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 1,33










(t, J=7,38 Hz, CH


3


), 1,95 (m, CH


2


),










2,69 (s, CH


3


), 4,12 (t, J=6,3 Hz,










CH


2


), 6,86 (d, J=7,69 Hz, 1H), 6,94










(d, J=8,37 Hz, 1H), 7,46 (pseudo t,










J=7,8 Hz, 1H)






VI-5




—




—CH


2


CH


2


Cl




(6-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 2,71










(s, CH


3


), 3,94 (t, J=6,1 Hz, CH


2


),










4,41 (t, J=6,1 Hz, CH


2


), 6,96 (t, J=7,1










Hz, 2H), 7,5 (t, J=7,8 Hz, 1H)






VI-6




—




—CH


2


CH


2


OC


2


H


5






(6-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 1,23










(t, J=7 Hz, CH


3


), 2,69 (s, CH


3


), 3,65










(q, J=7 Hz, CH


2


), 3,91 (t, J=5,16 Hz










CH


2


), 4,30 (t, J=5,16 Hz, CH


2


), 6,89










(d, J=7,7 Hz, 1H), 7,0 (d, J=8,3 Hz










1H), 7,47 (pseudo t, J=8,1 Hz, 1H)






VI-7




—




C


2


H


5






(5-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 1,53










(t, J=7Hz, CH


3


), 2,36 (s, CH


3


), 4,25










(q, J=7 Hz, CH


2


), 7,0 (d, J=8,53 Hz,










1H), 7,45 (d, J1=8,53 Hz, J2=2,15 Hz,










1H), 7,75 (d, J=2,15 Hz, 1H)






VI-8




—




n-C


3


H


7






(5-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 1,08










(t, J=7,38 Hz, CH


3


), 1,85 (m, CH


2


),










2,23 (s, CH


3


), 3,99 (t, J=6,5 Hz), 6,74










(d, J=8,2 Hz, 1H), 6,92 (m, 1H), 7,34










(d, J=1,65 Hz, lH)






VI-9




—




i-C


3


H


7






(5-) CH


3








1


H-NMR (CDCl


3


TMS, δ, ppm): 1,45










(d, J=6,06, 2×CH


3


), 2,35 (s, CH


3


),










4,77 (sept., J=6,06 Hz, 1H), 6,99 (d,










J=8,57 Hz, 1H), 7,43 (dd, J1=8,56 Hz,










1H, J2=2,1 Hz, 1H), 7,74 (d, J=2,1










Hz, 1H)






VI-10




—




C


2


H


5






(6-)CH


2


Cl




(Oil)






VI-11




—




—CF


2


CHFCl




(6-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 2,78










(s, CH


3


), 6,46 (td, CHFCl), 7,2-7,6










(Ar—H)






VI-12




—




CHF


2






(6-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 2,76










(s, CH


3


), 6,61 (t, CHF


2


), 7,27-7,59










(Ar—H)






VI-13




—




CH


3






(5-)C(CH


3


)


3






Fp.: 62° C.






VI-14




—




CHF


2






(4-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 2,50










(s, CH


3


), 6,68 (t, CHF


2


), 7,05-7,92










(Ar—H)






VI-15




—




CHF


2






(5-)CH


3








1


H-NMR (CDCl


3


, TMS, δ, ppm): 2,45










(s, CH


3


), 6,64 (t, CHF


2


), 7,35-7,86










(AR—H)






VI-16




—




—CH


2


CH


2


Cl




(6-)CH


3








VI-17




—




—CH


2


CH═CH


2






(6-)CH


3








VI-18




—




—CH


2


C≡CH




(6-)CH


3








VI-19




—




—CH


2


C


6


H


5






(6-)CH


3
















Starting Materials of the Formula (X):




Example (X-1)
















Step 1: Preparation of 2-isopropoxy-6-methyl-nitrobenzene




A mixture of 153 g (1.0 mol) of 3-methyl-2-nitro-phenol, 172.5 g (1.25 mol) of potassium carbonate, 170 g (1.0 mol) of 2-iodo-propane and 400 ml of acetone is heated under reflux for 12 hours. It is subsequently concentrated under a water pump vacuum, the residue is stirred with 400 ml of methylene chloride, the mixture is filtered and the filter product is washed with methylene chloride. The solvent is removed carefully from the filtrate by distillation under a water pump vacuum.




183.4 g of 2-isopropoxy-6-methyl-nitrobenzene are obtained as a yellow oily residue.






1


H-NMR (CDCl


3


, TMS, δ, ppm): 1.33 (d, J=6.1 Hz, 2×CH


3


), 2.28 (s, CH


3


), 4.6 (sept., J=6.1 Hz, 1H), 6.8 (d, J=7.7 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 7.26 (pseudo t, J=8.1 Hz, 1H).




Step 2: Preparation of 2-isopropoxy-6-methyl-aniline




183.3 g (0.94 mol) of 2-isopropoxy-6-methyl-nitrobenzene are hydrogenated in 1 litre of ethyl acetate in the presence of 9.5 g of Raney nickel under a hydrogen pressure of from 40 to 60 bar for 5 hours. The mixture is then filtered and the solvent is carefully removed from the filtrate by distillation under a water pump vacuum.




139.4 g (90% of theory) of 2-isopropoxy-6-methyl-aniline are obtained as an orange-coloured oily residue.


1


H-NMR (CDCl


3


, TMS, δ, ppm): 1.36 (d, J=6.1 Hz, 2×CH


3


), 2.16 (s, CH


3


), 3.72 (s, NH2), 4.51 (sept., J=6.1 Hz, 1H), 6.65-6.70 (m, 3H).




USE EXAMPLES




In the Use Examples, the compounds specified below are used as comparison substances











4,5-Dimethoxy-2-(2-methoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (known from EP 534266);











4,5-Diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-, 1,2,4-triazol-3-one (known from EP 534266).




Example A




Pre-emergence Test




Solvent: 5 parts by weight of acetone




Emulsifier: 1 part by weight of alkylaryl polyglycol ether




To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.




Seeds of the test plants are sown in normal soil, and, after 24 hours, the soil is watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive.




After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:




0%=no action (like untreated control)




100%=total destruction




In this test, the compounds according to Preparation Examples 1, 7-21, 23-41, 46-49, 51, 54, 55, 57, 60, 62, 65, 68, 72-74, 76, 78, 79, 88, 89, 199, 207, 209, 222 and 901 for example, exhibit a very strong action against broad-leaved weeds.




Example B




Post-emergence Test




Solvent: 5 parts by weight of acetone




Emulsifier: 1 part by weight of alkylaryl polyglycol ether




To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.




Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 2,000 l of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.




The figures denote:




0%=no action (like untreated control)




100%=total destruction




In this test, the compounds according to Preparation Examples 1, 7-10, 12, 13, 15, 16, 17, 25, 30, 31, 38, 40, 41, 46 and 47, for example, exhibit a very strong action against broad-leaved weeds.



Claims
  • 1. A compound of the formula (I), whereinA represents a single bond, Q represents oxygen or sulphur, R1 represents hydrogen or formyl or represents in each case optionally cyano-, fluoro-, chloro-, bromo-, phenyl- or C1-C4-alkoxy-substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C1-C4-alkyl-substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-carbonyl or C3-C6-cycloalkyl-sulphonyl, R2 represents cyano, fluoro, chloro or bromo or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C1-C4-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and R3 represents in each case optionally substituted heterocyclyl of the formula below,  in which Q1 represents oxygen or sulphur, and R4 represents hydrogen, or amino, or represents C2-C10-alkylideneaniino, or represents optionally fluoro-, chloro-, bromo-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted C1-C6alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C2-6-Calkenyl or C2-6-alkinyl, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkoxy, C1-C6-alkylamino or C1-C6-alkyl-carbonylamino, or represents C3-C6-alkenyloxy, or represents di-(C1-C6-alkyl)-amino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C1-C4-alkyl-substituted C3-C6-cycloalkyl, C3-C6-cycloalkylamino or C3-C6-cycloalkyl-C1-C4-alkyl, R5 represents hydrogen, or represents optionally fluoro-, chloro-, bromo-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C2-C6-alkenyl or C2-C6-alkinyl, or represents in each case optionally fluoro-, chloro-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino or C1-C6-alkyl-carbonylamino, or represents C3-C6-alkenyloxy, C3-C6-alkinyloxy, C3-C6-alkenylthio, C3-C6-alkinylthio, C3-C6-alkenylamino or C3-C6-alkinylamino, or represents di-(C1-C4-alkyl)-amino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C1-C4-alkyl-substituted C3-C6-cycloalkyl, C5-C6-cycloalkenyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkylthio, C3-C6-cycloalkylamino, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C4-alkoxy, C3-C6-cycloalkyl-C1-C4-alkylthio or C3-C6-cycloalkyl-C1-C4-alkylamino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy- and/or C1-C4-alkoxy-carbonyl-substituted phenyl, phenoxy, phenyl-C1-C4-alkoxy, phenylthio, phenyl-C1-C4-alkylthio, or R4 and R5 together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and with the proviso that if R1 represents methyl then R2 does not represent 5-methoxy and if R1 represents ethyl then R2 does not represent 5-ethoxy.
  • 2. A compound of the formula (I) according to claim 1, whereinA represents a single bond, Q represents oxygen or sulphur, R1 represents methyl, ethyl, n- or i-propyl, R2 represents chloro or methyl- in each case in position 5 or 6- and R3 represents optionally substituted triazolinyl of the formula below,  in which Q1 represents oxygen or sulphur, and R4 represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents propenyl or propinyl, or represents methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl, and R5 represents hydrogen, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally fluoro and/or chloro-substituted propenyl or propinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, or represents propenyloxy or cyclopropyl, and with the proviso that if R1 represents methyl then R2 does not represent 5-methoxy and if R1 represents ethyl then R2 does not represent 5-ethoxy.
  • 3. A compound of the formula (I) according to claim 1, whereinA represents a single bond, Q represents oxygen or sulphur, R1 represents hydrogen or formyl, or represents in each case optionally fluoro-, chloro-, bromo-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, acetyl, propionyl, butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, n-, i-, s- or t-butylsulphonyl, or represents in each case optionally fluoro-, chloro- or methyl-substituted cyclopropyl, cyclopropylcarbonyl or cyclopropylsulphonyl, R2 represents cyano, fluoro, chloro or bromo, or represents in each case optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy, butenyloxy, propinyloxy or butinyloxy and R3 represents in each case optionally substituted heterocyclyl of the formulae below,  in which Q1 represents oxygen or sulphur, and R4 represents hydrogen, or amino, or represents C3-C4-alkylideneamino, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy or butenyloxy, or represents dimethylamino or diethylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, R5 represents hydrogen, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted ethenyl, propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylantino, or represents dimethylamino, diethylamino or dipropylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluoro-, chloro-, methyl-, trifluoromethyl-, methoxy-and/or methoxy-carbonyl substituted phenoxy, benzyloxy, phenylthio, benzylthio, or R4 and R5 together represent optionally branched alkanediyl having 3 to 11 carbon atoms, with the proviso that if R1 represents methyl then R2 does not represent 5-methoxy and if R1 represents ethyl then R2 does not represent 5-ethoxy.
  • 4. The compound of formula (I) according to claim 1 whereinA represents a single bond, Q represents oxygen, R1 represents 2,2-difluoro-ethyl, R2 represents (6-)ethyl, and R3 represents 4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-on-2-yl.
  • 5. An herbicidal composition composing an herbicidally effective amount of a compound according to claim 1 and an inert carrier.
  • 6. A method of controlling unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation an herbicidally effective amount of a compound according to claim 1.
Priority Claims (1)
Number Date Country Kind
195 25 162 Jul 1995 DE
Parent Case Info

This is a Continuation of U.S. Ser. No. 09/006,686, filed on Jan. 8,1998 (now abandoned); which is a Continuation-in-Part of International Application PCT/EP96/02826, filed on Jun. 28, 1996.

US Referenced Citations (8)
Number Name Date Kind
5057144 Daum et al. Oct 1991
5085684 Muller et al. Feb 1992
5238910 Müller et al. Aug 1993
5252540 Heistracher et al. Oct 1993
5300480 Haas et al. Apr 1994
5488028 Haas et al. Jan 1996
5534486 Müller et al. Jul 1996
5552369 Findeisen et al. Sep 1996
Foreign Referenced Citations (12)
Number Date Country
42 34 801 A1 Apr 1994 DE
195 25 162 Jan 1997 DE
0 425 948 A2 May 1991 EP
0 482 349 A2 Apr 1992 EP
0 534 266 A1 Mar 1993 EP
0 708 087 A1 Apr 1996 EP
WO 9527703 Apr 1994 WO
WO 9611188 Apr 1996 WO
WO 9622982 Aug 1996 WO
WO 9627590 Sep 1996 WO
WO 9627591 Sep 1996 WO
WO 9635680 Nov 1996 WO
Continuations (1)
Number Date Country
Parent 09/006686 Jan 1998 US
Child 09/223246 US
Continuation in Parts (1)
Number Date Country
Parent PCT/EP96/02826 Jun 1996 US
Child 09/006686 US