Fused heterocyclic dicarboxylic acid diamide derivatives or salts thereof, herbicide and method for using the same

Abstract

A fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I): 1

Description

TECHNICAL FIELD

[0001] The present invention relates to novel fused heterocyclic dicarboxylic acid diamide derivatives or salts thereof, a herbicide containing said compound or salt thereof as an active ingredient, and a method for using said herbicide.

BACKGROUND ART

[0002] In JP-A-6-2519, there is mentioned that pyrazinedicarboxylic acid diamide derivatives are useful as herbicide. In JP-A-9-323974, there is mentioned that pyridinedicarboxylic acid diamide derivatives are useful as herbicide.

DISCLOSURE OF THE INVENTION

[0003] The present inventors have conducted extensive studies with the aim of developing a novel herbicide. As a result, it has been found that the fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) of the present invention or salts thereof are novel compounds not found in literature and having an excellent herbicidal activity. Based on this finding, the present invention has been accomplished.

[0004] The present invention relates to fused heterocyclic dicarboxylic acid diamide derivatives represented by the following general formula (I): 4

[0005] wherein R1 represents hydrogen atom or (C1-C6) alkyl group;

[0006] R2 and R3 may be same or different and each represents hydrogen atom, (C1-C8) alkyl group, halo (C1-C6) alkyl group, (C3-C8) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, alkylthio (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, amino (C1-C6) alkyl group, substituted amino (C1-C6) alkyl group substituted with one or two, same or different (C1-C6) alkyl groups, phenyl (C1-C6) alkyl group, substituted phenyl (C1-C6) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups, phenyl (C1-C6) alkoxy group or substituted phenyl (C1-C6) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups; or

[0007] R2 and R3, taken conjointly, represent a 5- to 6-membered heterocycle having at least one, same or different heteroatoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, further, the carbon atom or nitrogen atom on said heterocycle may have at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group and halo (C1-C6) alkylthio group;

[0008] X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C1) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, amino group, substituted amino group substituted with same or different (C1-C6) alkyl groups, cyano (C1-C6) alkyl groups, phenyl (C,-C1) alkyl groups, (C1-C6) alkoxycarbonyl (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl groups, (C1-C6) acyl groups, (C1-C6) alkylsulfonyl groups or halo (C1-C6) alkylsulfonyl groups, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C1) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C1) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C1) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenyl (C1-C6) alkyl group or substituted phenyl (C1-C6) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group; and 5

[0009] represents Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13 or Q14, wherein:

[0010] Q1 is a group of the following formula: 6

[0011] wherein Y represents hydrogen atom, halogen atom, nitro group, cyano group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C1) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6)) alkyl group, (C1-C6) alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, amino group, substituted amino group having at least one, same or different substituents selected from the group consisting of (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkoxyaminocarbonyl group, (C1-C6) acyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl (C1-C6) alkyl group, (C3-C5) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C1-C6) alkyl groups; and

[0012] R4 represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (c3-c6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C1) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, methylenedioxy group, amino group and substituted amino group substituted with at least one, same or different (C1-C6) alkyl groups, cyano (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl groups, (C1-C6) alkoxyaminocarbonyl groups, (C1-C6) acyl groups, (C1-C6) alkylsulfonyl groups, halo (C1-C6) alkylsulfonyl groups or phenyl (C1-C6) alkyl groups;

[0013] Q2 is a group of the following formula: 7

[0014] wherein at least one of A, B, D and E represent a nitrogen atom, and the others of A, B, D and E represent C-R5 wherein R5 represents hydrogen atom, halogen atom, nitro group, cyano group, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C1) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, amino group or substituted amino group having at least one, same or different substituents selected from the group consisting of (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkoxyaminocarbonyl group, (C1-C6) acyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl (C1-C6) alkyl group; and Y is as defined above;

[0015] Q3 is a group of the following formula: 8

[0016] wherein at least one of F, G, J and K represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N-R6 wherein R6 represents hydrogen atom, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylsulfonyl group or halo (C1-C6) alkylsulfonyl group, and the others of F, G, J and K each represents C—(R7)R8 wherein R7 and R8 may be same or different and represent hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, phenyl (C1-C6) alkyl group, substituted phenyl (C1-C6) alkyl group substituted with at least one, same or different halogen atoms or (C1-C6) alkyl groups, amino (C1-C6) alkyl group, substituted amino (C1-C6) alkyl group substituted with at least one, same or different (C1-C6) alkyl groups or phenyl (C1-C6) alkoxy group; and Y is as defined above; and G and J may be taken conjointly to represent CH═CH;

[0017] Q4 is a group of the following formula: 9

[0018] wherein R9 is same or different and represents halogen atom, nitro group, cyano group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, amino group, substituted amino group substituted with at least one, same or different substituents selected from the group consisting of (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkoxyaminocarbonyl group, (C1-C1) acyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl (C1-C6) alkyl group, (C3-C5) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C1-C6) alkyl groups; m represents an integer of 0 to 2;

[0019] Z represents oxygen atom, sulfur atom or N-R10 wherein R10 represents hydrogen atom, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group or (C1-C6) alkylthio (C1-C6) alkyl group; and Y is as defined above;

[0020] Q5 is a group of the following formula: 10

[0021] wherein R9, Y, Z and m are as defined above;

[0022] Q6 is a group of the following formula: 11

[0023] wherein R9, Y, Z and m are as defined above;

[0024] Q7 is a group of the following formula: 12

[0025] wherein at least one of L, M and T represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N—R11 wherein R11 represents hydrogen atom, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) cycloalkyl group, (C1-C1) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group or (C1-C6) alkylthio (C1-C6) alkyl group, and the others of L, M and T each represents C—(R12)R13 wherein R12 and R13 may be same or different and each represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, phenyl (C1-C6) alkyl group, substituted phenyl (C1-C6) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups, phenyl (C1-C6) alkoxy group, substituted phenyl (C1-C6) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups, amino (C1-C6) alkyl group or substituted amino (C1-C6) alkyl group substituted with at least one, same or different (C1-C6) alkyl groups;

[0026] Q8 is a group of the following formula: 13

[0027] wherein R14 represents hydrogen atom or is the same as R9, and Y and Z are as defined above;

[0028] Q9 is a group of the following formula: 14

[0029] wherein R14, Y and Z are as defined above;

[0030] Q10 is a group of the following formula: 15

[0031] wherein R14, Y and Z are as defined above;

[0032] Q1 is a group of the following formula: 16

[0033] wherein R14 Y and Z are as defined above;

[0034] Q12 is a group of the following formula: 17

[0035] wherein R14, Y and Z are as defined above;

[0036] Q13 is a group of the following formula: 18

[0037] wherein R14, Y and Z are as defined above; and

[0038] Q14 is a group of the following formula: 19

[0039] wherein R9 is as defined above and n represents an integer of 0 to 4; and

[0040] salts of said compounds, a herbicide containing said compound as an active ingredient, and a method for using said herbicide.

[0041] In the definitions of the substituents in the fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) or salts thereof, the term “halogen atom” means chlorine atom, bromine atom, iodine atom or fluorine atom; the term (C1-C8) means that the number of carbon atoms is 1 to 8; the term (C1-C8) alkyl group, for example, means a straight chain or branched chain alkyl group having 1 to 8 carbon atoms; and the term “halo (C1-C6) alkyl group” means a straight chain or branched chain alkyl group having 1 to 6 carbon atoms and substituted with at least one, same or different halogen atoms.

[0042] As examples of the salt, inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate and the like; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like; and salts of metal ions such as sodium ion, potassium ion, calcium ion and the like can be referred to.

[0043] As a preferable embodiment of the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I), a case where R1 and R2 are both hydrogen atom, R3 is (C1-C8) alkyl group or (C3-C8) cycloalkyl group, X is halogen atom or (C1-C6) alkyl group, and 20

[0044] is Q2, Q3, Q4, Q6, Q7, Q8, Q11 or the like can be referred to. As a further preferable embodiment, cases where X is substituted at the 2- and 3-positions or at the 2-, 3- and 6-positions can be referred to.

[0045] The fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) can be produced, for example, according to the production process schematically shown below.

[0046] Production Process 21

[0047] wherein R2, R3, X and 22

[0048] are as defined above, and hal represents a halogen atom.

[0049] A fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I-1) can be produced by hydrolyzing a compound represented by general formula (VIII) in the presence of an acid or an alkali to form a dicarboxylic acid represented by general formula (VII), converting it into an acid anhydride (VI) in the presence of a dehydrating agent, reacting the acid anhydride with a substituted aniline (V) in the presence or absence of an inert solvent to form anilides (IV-1) and (IV-2), and then after isolating or without isolating them, reacting them with a dehydrating agent in the presence or absence of an inert solvent to form imides represented by general formula (III), and after isolating or without isolating the imides (III), reacting them with an amine or a salt thereof represented by general formula (II-1) or (II-2) in the presence or absence of an inert solvent.

[0050] A. General formula (VIII)→General formula (VII)

[0051] As the inert solvents which can be used in this reaction, for example, water, water-soluble solvents such as methanol, ethanol, propanol and the like and mixtures of the water-soluble solvents can be referred to.

[0052] As the base which can be used for the hydrolysis, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like can be referred to. The amount of the base may be appropriately selected from a range of 2 to 10 equivalents per equivalent of the diester of general formula (VIII).

[0053] The reaction can be carried out at a temperature ranging from ambient temperature to the reflux temperature of the used inert solvent. The reaction time may vary with scale and temperature of the reaction, and it may be appropriately selected from a range of several minutes to 48 hours.

[0054] After completion of the reaction, the objective product is isolated from the reaction mixture containing it according to a conventional method, and then the product is purified by recrystallization, distillation, column chromatography or the like according to the need, whereby the objective product can be obtained.

[0055] It is also possible to use the product obtained in this step in the subsequent reaction without isolation.

[0056] B. General formula (VII)→General formula (VI)

[0057] The inert solvent used in this reaction may be any inert solvent so far as its use does not obstruct the progress of this reaction greatly. Examples of the inert solvent include halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and the like; acyclic and cyclic ethers such as methyl cellosolve, diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and the like; and organic acids such as acetic acid, trifluoroacetic acid and the like. These inert solvents may be used either alone or in the form of a mixture.

[0058] It is also possible to replace the inert solvent with an excessive quantity of the dehydrating agent.

[0059] As the dehydrating agent, for example, acetic anhydride, trifluoroacetic anhydride and the like can be used. The amount of these dehydrating agents may be appropriately selected from a range of from equi-molar quantity to excessive molar quantity per mol of the compound of general formula (VII). Preferably the dehydrating agent is used in an equimolar quantity.

[0060] The reaction temperature may be appropriately selected in a range of from ambient temperature to the boiling point range of the used inert solvent. When no inert solvent is used, the reaction may be carried out in the boiling point range of the used dehydrating agent.

[0061] The reaction time may vary with scale and temperature of the reaction, and it ranges from several minutes to 48 hours.

[0062] After completion of the reaction, the objective product is isolated from the reaction mixture containing it according to a conventional method, and then the product is purified by recrystallization, distillation, column chromatography or the like according to the need, whereby the objective product can be obtained.

[0063] This reaction can be carried out according to the description of J. Org. Chem. Soc., 52, 129 (1987); J. Am. Chem. Soc., 51, 1865 (1929); ibid., 63, 1542 (1941); etc.

[0064] It is also possible to use the objective product in the subsequent reaction without isolation.

[0065] C. General formula (VI)→General formula (IV-1)+General formula (IV-2)

[0066] As the inert solvent used in this reaction, any inert solvent may be used so far as it does not obstruct progress of the reaction greatly. Examples of the inert solvent include aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene and the like; acyclic and cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and the like; esters such as ethyl acetate and the like; amides such as dimethylformamide, dimethylacetamide and the like; acids such as acetic acid and the like; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone; water and the like. These inert solvents may be used either alone or in the form of a mixture of two or more.

[0067] Since this reaction is an equimolar reaction, the reactants may be used in equimolar amounts. It is also possible, however, to use any of the reactants in an excessive amount. If desired, this reaction may be carried out under a dehydrating condition.

[0068] The reaction temperature may be appropriately selected in a range of from ambient temperature to the boiling point range of the used inert solvent. When no inert solvent is used, the reaction may be carried out in the boiling point range of the used dehydrating agent.

[0069] The reaction time may vary with scale and temperature of the reaction, and it ranges from several minutes to 48 hours.

[0070] After completion of the reaction, the objective product is isolated from the reaction mixture containing it according to a conventional method, and then the product is purified by recrystallization, distillation, column chromatography or the like according to the need, whereby the objective product can be obtained.

[0071] It is also possible to use the objective product in the subsequent reaction without isolation.

[0072] D. General formula (IV-1) +General formula (IV-2)→General formula (III)

[0073] This reaction can be carried out in the same manner as B, whereby the objective product can be obtained. It is also possible to use the objective product in the subsequent reaction without isolation.

[0074] Hereunder are shown typical examples of the imide represented by general formula (III).

[0075] (1). N-(3-Chloro-2,6-diethylphenyl)-1,3-dimethylpyrazolo[5,4-b]pyridine-5,6-dicarboximide 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0076] 1.09(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0077] 2.43(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz),

[0078] 2.69(3H,s), 4.26(3H,s), 7.21(1H,d,J=8.4 Hz),

[0079] 7.47(1H,d,J=8.4 Hz), 8.61(1H,s)

[0080] (2). N-(3-chloro-2,6-diethylphenyl)thieno[3,2-b]pyridine-5,6-dicarboximide 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0081] 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz), 2.44 (2H,q,J=7.5 Hz), 2.63(2H,q,J=7.5 Hz),

[0082] 7.20(1H,d,J=8.4 Hz), 7.47(1H,d,J=8.4 Hz),

[0083] 7.90(1H,d,J=5.7 Hz), 8.17(1H,d,J=5.7 Hz),

[0084] 8.79(1H,s).

[0085] (3). N-(3-chloro-2,6-diethylphenyl)-2,3-dihydrothieno-[3,2-b]pyridine-5,6-dicarboximide 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0086] 1.06(3H,t,J=7.5 Hz), 1.12(3H,t,J=7.5 Hz),

[0087] 2.39(2H,q,J=7.5 Hz), 2.58(2H,q,J=7.5 Hz), 3.51-3.68(4H,m), 7.17(1H,d,J=8.4 Hz),

[0088] 7.44(1H,d,J=8.4 Hz), 7.95(1H,s).

[0089] (4). N-(3-chloro-2,6-diethylphenyl)-2,3-dihydrothieno-[2,3-b]pyridine-5,6-dicarboximide 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0090] 1.05(3H,t,J=7.5 Hz), 1.11(3H,t,J=7.5 Hz),

[0091] 2.38(2H,q,J=7.5 Hz), 2.57(2H,q,J=7.5 Hz), 3.47-3.61(4H,m), 7.16(1H,d,J=8.4 Hz),

[0092] 7.43(1H,d,J=8.4 Hz), 7.85(1H,s).

[0093] (5). N-(3-chloro-2,6-diethylphenyl)-furo[2,3-b]pyridine-5,6-dicarboximide 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0094] 1.08(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0095] 2.43(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz),

[0096] 7.11(1H,d,J=2.6 Hz), 7.24(1H,d,J=8.4 Hz),

[0097] 7.47(1H,d,J=8.4 Hz), 8.05(1H,d,J=2.6 Hz),

[0098] 8.53(1H,s).

[0099] (6). N-(3-chloro-2,6-diethylphenyl)-1-methyl-pyrrolo-[3,2-b]pyridine-5,6-dicarboximide

[0100] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0101] 1.04(3H,t,J=7.5 Hz), 1.08(3H,t,J=7.5 Hz),

[0102] 2.45(2H,q,J=7.5 Hz), 2.65(2H,q,J=7.5 Hz),

[0103] 3.93(3H,s), 6.95(1H,d,J=0.6 Hz),

[0104] 7.15(1H,d,J=8.0 Hz), 7.38(1H,d,J=8.0 Hz),

[0105] 7.61(1H,d,J=0.6 Hz), 8.17(1H,s).

[0106] (7). N-(3-chloro-2,6-diethylphenyl)-1-methoxy-pyrrolo-[3,2-b]pyridine-5,6-dicarboximide

[0107] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0108] 1.06(3H,t,J=7.5 Hz), 1.11(3H,t,J=7.5 Hz),

[0109] 2.42(2H,q,J=7.5 Hz), 2.65(2H,q,J=7.5 Hz),

[0110] 4.21(3H,s), 6.90(1H,d,J=0.6 Hz),

[0111] 7.15(1H,d,J=8.0 Hz), 7.38(1H,d,J=8.0 Hz),

[0112] 7.81(1H,d,J=0.6 Hz), 8.32(1H,s)

[0113] (8). N-(3-chloro-2,6-diethylphenyl)-1,8-naphthylidine-2,3-dicarboximide

[0114] 1H-NMR [TMS/CDCl3, &dgr; (ppm)

[0115] 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0116] 2.43(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz),

[0117] 7.24(1H,d,J=8.4 Hz), 7.52(1H,d,J=8.4 Hz),

[0118] 8.05(1H,dd,J=2.9 and 7.9 Hz), 8.81(1H,d,J=7.9 Hz),

[0119] 9.04(1H,s), 9.62(1H,d,J=2.9 Hz).

[0120] (9). N-(3-chloro-2,6-diethylphenyl)-5-oxo-5,6,7,8-tetrahydroquinoline-2,3-dicarboximide

[0121] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0122] 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0123] 2.30(2H,m), 2.43(2H,q,J=7.5 Hz), 2.48(2H,m),

[0124] 2.61(2H,q,J=7.5 Hz), 2.85(2H,m),

[0125] 7.19(1H,d,J=8.4 Hz), 7.42(1H,d,J=8.4 Hz),

[0126] 8.89(1H,s).

[0127] (10). N-(3-chloro-2,6-diethylphenyl)-6-methyl-5,6,7,8-tetrahydro-1,6-naphthylidine-2,3-dicarboximide

[0128] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0129] 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0130] 2.33(2H,q,J=7.5 Hz), 2.52(2H,q,J=7.5 Hz),

[0131] 2.95(3H,s), 3.00-3.12(4H,m), 3.54(2H,m),

[0132] 7.15(1H,d,J=8.4 Hz), 7.42(1H,d,J=8.4 Hz),

[0133] 8.02(1H,s).

[0134] (11). N-(3-chloro-2,6-diethylphenyl)-7,8-dihydro-5H-thiopyrano[4,3-b]pyridine-2,3-dicarboximide

[0135] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0136] 1.08(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0137] 2.39(2H,q,J=7.5 Hz), 2.58(2H,q,J=7.5 Hz),

[0138] 3.11(2H,t,J=5.8 Hz), 3.52(2H,t,J=5.8 Hz),

[0139] 3.97(2H,s), 7.19(1H,d,J=8.4 Hz),

[0140] 7.46(1H,d,J=8.4 Hz), 8.08(1H,s).

[0141] (12). N-(3-chloro-2,6-diethylphenyl)-7,8-dihydro-5H-pyrano[4,3-b]pyridine-2,3-dicarboximide

[0142] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0143] 1.07(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0144] 2.39(2H,q,J=7.5 Hz), 2.58(2H,q,J=7.5 Hz),

[0145] 3.31(2H,t,J=6.2 Hz), 4.15(2H,t,J=6.2 Hz),

[0146] 4.96(2H,s), 7.18(1H,d,J=8.4 Hz),

[0147] 7.46(1H,d,J=8.4 Hz), 7.90(1H,s).

[0148] (13). N-(3-chloro-2,6-diethylphenyl)-2,3-quinoxaline-dicarboximide

[0149] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0150] 1.11(3H,t,J=7.5 Hz), 1.16(3H,t,J=7.5 Hz),

[0151] 2.46(2H,q,J=7.5 Hz), 2.64(2H,q,J=7.5 Hz),

[0152] 7.24(1H,d,J=8.4 Hz), 7.51(1H,d,J=8.4 Hz), 8.07-8.13(2H,m), 8.48-8.54(2H,m).

[0153] (14). N-(3-chloro-2-methylphenyl)-2,3-quinoxaline-dicarboximide

[0154] 1H-NMR [TMS/CDC3, &dgr; (ppm)]

[0155] 2.29(3H,s), 7.24(1H,d,J=8.0 Hz),

[0156] 7.34(1H,t,J=8.0 Hz), 7.56(1H,d,J=8.0 Hz), 8.06-8.12(2H,m), 8.46-8.51(2H,m).

[0157] (15). N-(3-chloro-2,6-diethylphenyl)-5-fluoro-2,3-quinolinedicarboximide

[0158] mp 116-118° C.

[0159] (16). N-(3-chloro-2,6-diethylphenyl)-6-fluoro-2,3-quinolinedicarboximide

[0160] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0161] 1.09(3H,t,J=7.8 Hz), 1.14(3H,t,J=7.5 Hz),

[0162] 2.44(2H,q,J=7.5 Hz), 2.56-2.68(2H,m),

[0163] 7.22(1H,d,J=8.1 Hz), 7.48(1H,d,J=8.1 Hz), 7.75-7.81(2H,m), 8.51(1H,m), 8.77(1H,s).

[0164] (17). N-(3-chloro-2,6-diethylphenyl)-7-fluoro-2,3-quinolinedicarboximide

[0165] 1H-NMR [TMS/CDCl3&dgr; (ppm)]

[0166] 1.09(3H,t,J=7.8 Hz), 1.14(3H,t,J=7.5 Hz),

[0167] 2.44(2H,q,J=7.5 Hz), 2.56-2.68(2H,m),

[0168] 7.22(1H,d,J=8.1 Hz), 7.48(1H,d,J=8.1 Hz),

[0169] 7.63(1H,ddd,J=2.4, 8.1 and 9.3 Hz),

[0170] 8.12(1H,dd,J=2.4 and 9.6 Hz), 8.16(1H,dd,J=5.7 and

[0171] 9.3 Hz), 8.81(1H,s).

[0172] (18). N-(4-trifluoromethoxyphenyl)-7-fluoro-2,3-quinolinedicarboximide

[0173] mp 264-266° C.

[0174] (19). N-(4-trifluoromethoxyphenyl)-6-fluoro-2,3-quinolinedicarboximide

[0175] mp 287-289° C.

[0176] (20). N-(4-trifluoromethoxyphenyl)-5-fluoro-2,3-quinolinedicarboximide

[0177] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0178] 7.39-7.43(2H,m), 7.51(1H,ddd,J=0.9, 7.8 and

[0179] 9.0 Hz), 7.63-7.80(2H,m), 7.95(1H,ddd,J=6.0, 7.8 and 8.4 Hz), 8.30(1H,dd,J=0.9 and 8.4 Hz),

[0180] 9.09(1H,d,J=0.9 Hz).

[0181] (21). N-(2-methyl-4-pentafluoroethylphenyl)-6-fluoro-2,3-quinolinedicarboximide

[0182] 1H-NMR [TMS/CDC3, &dgr; (ppm)]

[0183] 2.33(3H,s), 7.43(1H,d,J=8.4 Hz),

[0184] 7.62(1H,d,J=8.4 Hz), 7.64(1H,s), 7.81-7.72(2H,m),

[0185] 8.50(1H,dd,J=5.4 and 9.0 Hz), 8.77(1H,s).

[0186] (22). N-(3-chloro-2,6-diethylphenyl)-5-chloro-2,3-quinolinedicarboximide

[0187] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0188] 1.10(3H,t,J=7.5 Hz), 1.15(3H,t,J=7.5 Hz),

[0189] 2.45(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz),

[0190] 7.22(1H,d,J=8.5 Hz), 7.50(1H,d,J=8.5 Hz), 7.89-7.96(2H,m), 8.42(1H,dd,J=2.0 and 8.0 Hz),

[0191] 9.29(1H,s).

[0192] (23). N-(3-chloro-2,6-diethylphenyl)-6-chloro-2,3-quinolinedicarboximide

[0193] 1H-NMR [TMS/d6-DMSO, &dgr; (ppm)]

[0194] 0.99(3H,t,J=7.5 Hz), 1.04(3H,t,J=7.5 Hz),

[0195] 2.40(2H,q,J=7.5 Hz), 2.60(2H,q,J=7.5 Hz),

[0196] 7.36(1H,d,J=8.5 Hz), 7.61(1H,d,J=8.5 Hz),

[0197] 8.09(1H,d,J=8.1 Hz), 8.40(1H,d,J=8.1 Hz),

[0198] 8.52(1H,s), 9.15(1H,s).

[0199] (24). N-(3-chloro-methylphenyl)-6-chloro-2,3-quinolinedicarboximide

[0200] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0201] 2.27(3H,s), 7.20(1H,d,J=7.8 Hz),

[0202] 7.32(1H,t,J=7.8 Hz), 7.53(1H,d,J=7.8 Hz),

[0203] 7.93(1H,dd,J=2.0 and 8.0 Hz), 8.11(1H,d,J=2.0 Hz),

[0204] 8.42(1H,d,J=8.0 Hz), 8.71(1H,s).

[0205] (25). N-(3-chloro-2,6-diethylphenyl)-7-chloro-2,3-quinolinedicarboximide

[0206] 1H-NMR [TMS/d6-DMSO, &dgr; (ppm)]

[0207] 0.99(3H,t,J=7.5 Hz), 1.04(3H,t,J=7.5 Hz),

[0208] 2.45(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz),

[0209] 7.37(1H,d,J=8.5 Hz), 7.62(1H,d,J=8.5 Hz),

[0210] 7.99(1H,dd,J=2.5 and 8.5 Hz), 8.43(1H,d,J=8.5 Hz),

[0211] 8.48(1H,d,J=2.5 Hz), 9.24(1H,s).

[0212] (26). N-(3-chloro-2,6-diethylphenyl)-5-methyl-2,3-quinolinedicarboximide

[0213] mp 178-180° C.

[0214] (27). N-(3-chloro-2,6-diethylphenyl)-6-methyl-2,3-quinolinedicarboximide

[0215] 1H-NMR [TMS/CDCl3&dgr; (ppm)]

[0216] 1.10(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0217] 2.45(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz),

[0218] 2.65(3H,s), 7.21(1H,d,J=8.5 Hz),

[0219] 7.47(1H,d,J=8.5 Hz), 7.80(1H,d,J=8.0 Hz),

[0220] 7.88(1H,s), 8.37(1H,d,J=8.0 Hz), 8.71(1H,s).

[0221] (28). N-(3-chloro-2,6-diethylphenyl)-8-methyl-2,3-quinolinedicarboximide

[0222] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0223] 1.00(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0224] 2.45(2H,q,J=7.5 Hz), 2.60(2H,q,J=7.5 Hz),

[0225] 2.95(3H,s), 7.20(1H,d,J=8.5 Hz),

[0226] 7.40(1H,d,J=8.5 Hz), 7.70(1H,t,J=8.0 Hz),

[0227] 7.95(1H,d,J=8.0 HZ), 8.75(1H,s).

[0228] (29). N-(3-chloro-2-methylphenyl)-6-methyl-2,3-quinolinedicarboximide

[0229] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0230] 2.26(3H,s), 2.65(3H,s), 7.20(1H,d,J=8.5 Hz),

[0231] 7.30(1H,t,J=8.5 Hz), 7.51(1H,d,J=8.5 Hz),

[0232] 7.85(1H,d,J=8.0 Hz), 7.87(1H,s),

[0233] 8.35(1H,d,J=8.0 Hz), 8.69(1H,s).

[0234] (30). N-(3-chloro-2,6-diethylphenyl)-6-hydroxy-2,3-quinolinedicarboximide

[0235] 1H-NMR [TMS/CDCl3, 6 (ppm)]

[0236] 1.06(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0237] 2.45(2H,q,J=7.5 Hz), 2.65(2H,q,J=7.5 Hz),

[0238] 7.20(1H,d,J=8.0 Hz), 7.45(1H,d,J=1.1 Hz), 7.50(1H,d,J=8.0 Hz), 7.60(1H,dd,J=1.1 and 8.5 Hz),

[0239] 8.38(1H,d,J=8.5 Hz), 8.62(1H,s).

[0240] (31). N-(3-chloro-2,6-diethylphenyl)-6-methoxy-2,3-quinolinedicarboximide

[0241] 1H-NMR [TMS/d6-DMSO, &dgr; (ppm)]

[0242] 1.10(3H,t,J=7.5 Hz), 1.18(3H,t,J=7.5 Hz),

[0243] 2.50(2H,q,J=7.5 Hz), 2.87(2H,q,J=7.5 Hz),

[0244] 3.95(1H,s), 7.21(1H,d,J=8.5 Hz),

[0245] 7.35(1H,d,J=8.5 Hz), 8.05(1H,d,J=8.0 Hz),

[0246] 8.86(1H,s), 9.24(1H,s), 10.28(1H,d,J=8.0 Hz).

[0247] (32). N-(3-chloro-2,6-diethylphenyl)-6,7-dimethoxy-2,3-quinolinedicarboximide

[0248] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0249] 1.09(3H,t,J=7.8 Hz), 1.14(3H,t,J=7.8 Hz),

[0250] 2.45(2H,q,J=7.8 Hz), 2.63(2H,q,J=7.8 Hz),

[0251] 4.10(6H,s), 7.20(1H,d,J=8.5 Hz), 7.28(1H,s),

[0252] 7.45(1H,d,J=8.5 Hz), 7.76(1H,s), 8.58(1H,s).

[0253] (33). N-(3-chloro-2,6-diethylphenyl)-6,7-methylenedioxy-2,3-quinolinedicarboximide

[0254] 1H-NMR [TMS/CDCl3, &dgr; (ppm)]

[0255] 1.09(3H,t,J=7.5 Hz), 1.15(3H,t,J=7.5 Hz),

[0256] 2.45(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz),

[0257] 6.27(2H,s), 7.20(1H,d,J=8.5 Hz), 7.32(1H,s),

[0258] 7.45(1H,d,J=8.5 Hz), 7.71(1H,s), 8.55(1H,s).

[0259] The fused heterocyclic diesters represented by general formula (VIII) and the dicarboxylic acids represented by general formula (VII) can be produced according to known methods, for example, the methods described in U.S. Pat. No. 3,414,580, U.S. Pat. No. 3,686,171, J. Med. Chem., 27, 1396 (1984), J. Heterocyclic Chem., 12, 1303 (1975), ibid. 15, 1447 (1978), ibid. 16, 1141 (1979), ibid. 17, 443 (1982), ibid. 21, 689 (1984), Beil., 25III, 2028, JP-A-52-77086, J. Am. Chem. Soc. , 81, 2456 (1956), J. Org. Chem., 37, 3224 (1972), JP-A-62-175480, JP-A-62-230782, JP-A-60-69083, JP-A-60-185783, JP-A-61-109790, JP-A-62-277385, JP-A-63-295575, JP-A-63-99067, JP-A-64-75474, JP-A-64-90118, Yakugaku Zasshi, 84, 416 (1964), Chem. and Pharm. Bull., 5, 277 (1957), J. Chem. Research (S), 1989, 196, etc.

[0260] E. General Formula (III)→General Formula (I-1)

[0261] As the inert solvents usable in this reaction, the inert solvents exemplified in B and pyridines can be referred to.

[0262] Since this reaction is an equimolar reaction, an amine represented by general formula (II-1) or an amine salt represented by general formula (II-2) is used in an equimolar amount to an imide represented by general formula (III), or in an excessive amount, if desired.

[0263] When an amine salt represented by general formula (II-2) is used in this reaction, a base must be used for the purpose of generating a free amine in the reaction system. As the base, an inorganic amine or an organic amine can be used. As the inorganic amine, for example, alkali metal hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and the like can be used. As the organic base, for example, triethylamine, pyridine, 4-dimethylaminopyridine, 1,8-diazabicyclo-[5,4,0]-7-undecene and the like can be used. The amount of these amines may be appropriately selected from a range of an equimolar amount to an excessive molar amount.

[0264] The reaction temperature may be appropriately selected from a range of −10° C. to the boiling point range of the used inert solvent, and preferably from a range of 0° C. to 150° C.

[0265] The reaction time may vary with temperature and scale of the reaction, and it ranges from several minutes to 48 hours.

[0266] After completion of the reaction, the objective product is isolated from the reaction system containing it and purified by recrystallization, distillation, column chromatography, etc. according to the need, whereby the objective product can be obtained.

[0267] Hereunder, typical examples of the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) and salt thereof will be shown in Table 1 to Table 14. The present invention is by no means limited by these compounds. In the tables, the expression “c-” means an alicyclic hydrocarbon, and the expression “Het” means 23 24 1 TABLE 1 25 No Y R3 X R4 mp ° C.  1 H C2H5 2,6-(C2H5)2-3-Cl 5-CH3 188-190  2 H n-C3H7 2,6-(C2H5)2-3-Cl 5-CH3 208-210  3 H i-C3H7 2,6-(C2H5)2-3-Cl 5-CH3 190-192  4 H c-C3H5 2,6-(C2H5)2-3-Cl 5-CH3  5 H n-C4H9 2,6-(C2H5)2-3-Cl 5-CH3  6 H s-C4H9 2,6-(C2H5)2-3-Cl 5-CH3  7 H i-C4H9 2,6-(C2H5)2-3-Cl 5-CH3  8 H t-C4H9 2,6-(C2H5)2-3-Cl 5-CH3  9 H n-C5H11 2,6-(C2H5)2-3-Cl 5-CH3  10 H neo-C5H11 2,6-(C2H5)2-3-Cl 5-CH3  11 H c-C5H9 2,6-(C2H5)2-3-Cl 5-CH3  12 H t-C5H11 2,6-(C2H5)2-3-Cl 5-CH3  13 H n-C6H13 2,6-(C2H5)2-3-Cl 5-CH3  14 H CH3 2-CH3-3-Cl 5-CH3  15 H C2H5 2-CH3-3-Cl 5-CH3  16 H n-C3H7 2-CH3-3-Cl 5-CH3  17 H i-C3H7 2-CH3-3-Cl 5-CH3  18 H c-C3H5 2-CH3-3-Cl 5-CH3  19 H n-C4H9 2-CH3-3-Cl 5-CH3  20 H s-C4H9 2-CH3-3-Cl 5-CH3  21 H i-C4H9 2-CH3-3-Cl 5-CH3  22 H t-C4H9 2-CH3-3-Cl 5-CH3  23 H n-C5H11 2-CH3-3-Cl 5-CH3  24 H neo-C5H11 2-CH3-3-Cl 5-CH3  25 H c-C5H9 2-CH3-3-Cl 5-CH3  26 H t-C5H11 2-CH3-3-Cl 5-CH3  27 H n-C6H13 2-CH3-3-Cl 5-CH3  28 H CH3 2,6-(C2H5)2-3-Cl 6-CH3 234-236  29 H C2H5 2,6-(C2H5)2-3-Cl 6-CH3 226-228  30 H n-C3H7 2,6-(C2H5)2-3-Cl 6-CH3 221-222  31 H i-C3H7 2,6-(C2H5)2-3-Cl 6-CH3  32 H c-C3H5 2,6-(C2H5)2-3-Cl 6-CH3  33 H n-C4H9 2,6-(C2H5)2-3-Cl 6-CH3  34 H s-C4H9 2,6-(C2H5)2-3-Cl 6-CH3  35 H i-C4H9 2,6-(C2H5)2-3-Cl 6-CH3  36 H t-C4H9 2,6-(C2H5)2-3-Cl 6-CH3  37 H n-C5H11 2,6-(C2H5)2-3-Cl 6-CH3  38 H neo-C5H11 2,6-(C2H5)2-3-Cl 6-CH3  39 H c-C5H9 2,6-(C2H5)2-3-Cl 6-CH3  40 H t-C5H11 2,6-(C2H5)2-3-Cl 6-CH3  41 H n-C6H13 2,6-(C2H5)2-3-Cl 6-CH3  42 H CH3 2-CH3-3-Cl 6-CH3  43 H C2H5 2-CH3-3-Cl 6-CH3 225-228  44 H n-C3H7 2-CH3-3-Cl 6-CH3 217-220  45 H i-C3H7 2-CH3-3-Cl 6-CH3  46 H c-C3H5 2-CH3-3-Cl 6-CH3  47 H n-C4H9 2-CH3-3-Cl 6-CH3  48 H s-C4H9 2-CH3-3-Cl 6-CH3  49 H i-C4H9 2-CH3-3-Cl 6-CH3  50 H t-C4H9 2-CH3-3-Cl 6-CH3  51 H n-C5H11 2-CH3-3-Cl 6-CH3  52 H neo-C5H11 2-CH3-3-Cl 6-CH3  53 H c-C5H9 2-CH3-3-Cl 6-CH3 218-219  54 H C2H5 4-OCF3 6-CH3 215-217  55 H n-C3H7 4-OCF3 6-CH3 202-204  56 H i-C3H7 4-OCF3 6-CH3 213-215  57 H C2H5 2,6-(C2H5)2-3-Cl 7-CH3  58 H n-C3H7 2,6-(C2H5)2-3-Cl 7-CH3 199-201  59 H i-C3H7 2,6-(C2H5)2-3-Cl 7-CH3  60 H c-C3H5 2,6-(C2H5)2-3-Cl 7-CH3  61 H n-C4H9 2,6-(C2H5)2-3-Cl 7-CH3  62 H s-C4H9 2,6-(C2H5)2-3-Cl 7-CH3  63 H i-C4H9 2,6-(C2H5)2-3-Cl 7-CH3  64 H t-C4H9 2,6-(C2H5)2-3-Cl 7-CH3  65 H n-C5H11 2,6-(C2H5)2-3-Cl 7-CH3  66 H neo-C5H11 2,6-(C2H5)2-3-Cl 7-CH3  67 H c-C5H9 2,6-(C2H5)2-3-Cl 7-CH3  68 H t-C5H11 2,6-(C2H5)2-3-Cl 7-CH3  69 H n-C6H13 2,6-(C2H5)2-3-Cl 7-CH3  70 H C2H5 2,6-(C2H5)2-3-Cl 8-CH3  71 H n-C3H7 2,6-(C2H5)2-3-Cl 8-CH3 227-228  72 H i-C3H7 2,6-(C2H5)2-3-Cl 8-CH3  73 H c-C3H6 2,6-(C2H5)2-3-Cl 8-CH3  74 H n-C4H9 2,6-(C2H5)2-3-Cl 8-CH3  75 H s-C4H9 2,6-(C2H5)2-3-Cl 8-CH3  76 H i-C4H9 2,6-(C2H5)2-3-Cl 8-CH3  77 H t-C4H9 2,6-(C2H5)2-3-Cl 8-CH3  78 H n-C5H11 2,6-(C2H5)23-Cl 8-CH3  79 H neo-C5H11 2,6-(C2H5)2-3-Cl 8-CH3  80 H c-C5H9 2,6-(C2H5)2-3-Cl 8-CH3  81 H t-C5H11 2,6-(C2H5)2-3-Cl 8-CH3  82 H n-C6H13 2,6-(C2H5)2-3-Cl 8-CH3  83 H CH3 2-CH3-3-Cl 8-CH3  84 H C2H5 2-CH3-3-Cl 8-CH3  85 H n-C3H7 2-CH3-3-Cl 8-CH3  86 H i-C3H7 2-CH3-3-Cl 8-CH3  87 H c-C3H5 2-CH3-3-Cl 8-CH3  88 H n-C4H9 2-CH3-3-Cl 8-CH3  89 H s-C4H9 2-CH3-3-Cl 8-CH3  90 H i-C4H9 2-CH3-3-Cl 8-CH3  91 H t-C4H9 2-CH3-3-Cl 8-CH3  92 H n-C5H11 2-CH3-3-Cl 8-CH3  93 H neo-C5H11 2-CH3-3-Cl 8-CH3  94 H c-C5H9 2-CH3-3-Cl 8-CH3  95 H t-C5H11 2-CH3-3-Cl 8-CH3  96 H n-C6H13 2-CH3-3-Cl 8-CH3  97 H H 2,6-(C2H5)2-3-Cl 5-F 266-268  98 H CH3 2,6-(C2H5)2-3-Cl 5-F  99 H C2H5 2,6-(C2H5)2-3-Cl 5-F 227-229 100 H n-C3H7 2,6-(C2H5)2-3-Cl 5-F 207-209 101 H i-C3H7 2,6-(C2H5)2-3-Cl 5-F 213-215 102 H c-C3H5 2,6-(C2H5)2-3-Cl 5-F 103 H n-C4H9 2,6-(C2H5)2-3-Cl 5-F 104 H s-C4H9 2,6-(C2H5)2-3-Cl 5-F 105 H i-C4H9 2,6-(C2H5)2-3-Cl 5-F 106 H t-C4H9 2,6-(C2H5)2-3-Cl 5-F 107 H n-C5H11 2,6-(C2H5)2-3-Cl 5-F 108 H neo-C5H11 2,6-(C2H5)2-3-Cl 5-F 109 H c-C5H9 2,6-(C2H5)2-3-Cl 5-F 110 H t-C5H11 2,6-(C2H5)2-3-Cl 5-F 111 H n-C6H13 2,6-(C2H5)2-3-Cl 5-F 112 H CH3 2-CH3-3-Cl 5-F 113 H C2H5 2-CH3-3-Cl 5-F 114 H n-C3H7 2-CH3-3-Cl 5-F 115 H i-C3H7 2-CH3-3-Cl 5-F 116 H c-C3H5 2-CH3-3-Cl 5-F 117 H n-C4H9 2-CH3-3-Cl 5-F 118 H s-C4H9 2-CH3-3-Cl 5-F 119 H i-C4H9 2-CH3-3-Cl 5-F 120 H t-C4H9 2-CH3-3-Cl 5-F 121 H n-C5H11 2-CH3-3-Cl 5-F 122 H neo-C5H11 2-CH3-3-Cl 5-F 123 H c-C5H9 2-CH3-3-Cl 5-F 124 H n-C3H7 4-OCF3 5-F 191-193 125 H i-C3H7 4-OCF3 5-F 210-212 126 H H 2,6-(C2H5)2-3-Cl 6-F 286-288 127 H CH3 2,6-(C2H5)2-3-Cl 6-F 247-249 128 H C2H5 2,6-(C2H5)2-3-Cl 6-F 212-213 129 H n-C3H7 2,6-(C2H5)2-3-Cl 6-F 210-212 130 H i-C3H7 2,6-(C2H5)2-3-Cl 6-F 202-204 131 H c-C3H5 2,6-(C2H5)2-3-Cl 6-F 132 H n-C4H9 2,6-(C2H5)2-3-Cl 6-F 133 H s-C4H9 2,6-(C2H5)2-3-Cl 6-F 134 H i-C4H9 2,6-(C2H5)2-3-Cl 6-F 135 H t-C4H9 2,6-(C2H5)2-3-Cl 6-F 136 H n-C5H11 2,6-(C2H5)2-3-Cl 6-F 137 H neo-C5H11 2,6-(C2H5)2-3-Cl 6-F 138 H c-C5H9 2,6-(C2H5)2-3-Cl 6-F 139 H t-C5H11 2,6-(C2H5)2-3-Cl 6-F 140 H n-C6H13 2,6-(C2H5)2-3-Cl 6-F 141 H CH3 2-CH3-3-Cl 6-F 142 H C2H5 2-CH3-3-Cl 6-F 143 H n-C3H7 2-CH3-3-Cl 6-F 144 H i-C3H7 2-CH3-3-Cl 6-F 145 H c-C3H5 2-CH3-3-Cl 6-F 146 H n-C4H9 2-CH3-3-Cl 6-F 147 H s-C4H9 2-CH3-3-Cl 6-F 148 H i-C4H9 2-CH3-3-Cl 6-F 149 H t-C4H9 2-CH3-3-Cl 6-F 150 H n-C5H11 2-CH3-3-Cl 6-F 151 H neo-C5H11 2-CH3-3-Cl 6-F 152 H c-C5H9 2-CH3-3-Cl 6-F 153 H t-C5H11 2-CH3-3-Cl 6-F 154 H n-C6H13 2-CH3-3-Cl 6-F 155 H C2H5 4-OCF3 6-F 242-244 156 H i-C3H7 4-OCF3 6-F 248-250 157 H C2H5 2,6-(C2H5)2-3-Cl 7-F 231-233 158 H n-C3H7 2,6-(C2H5)2-3-Cl 7-F 220-222 159 H i-C3H7 2,6-(C2H5)2-3-Cl 7-F 160 H c-C3H5 2,6-(C2H5)2-3-Cl 7-F 161 H n-C4H9 2,6-(C2H5)2-3-Cl 7-F 162 H s-C4H9 2,6-(C2H5)2-3-Cl 7-F 163 H i-C4H9 2,6-(C2H5)2-3-Cl 7-F 164 H t-C4H9 2,6-(C2H5)2-3-Cl 7-F 165 H n-C5H11 2,6-(C2H5)2-3-Cl 7-F 166 H neo-C5H11 2,6-(C2H5)2-3-Cl 7-F 167 H c-C5H9 2,6-(C2H5)2-3-Cl 7-F 168 H t-C5H11 2,6-(C2H5)2-3-Cl 7-F 169 H n-C6H13 2,6-(C2H5)2-3-Cl 7-F 170 H CH3 2-CH3-3-Cl 7-F 171 H C2H5 2-CH3-3-Cl 7-F 172 H n-C3H7 2-CH3-3-Cl 7-F 173 H i-C3H7 2-CH3-3-Cl 7-F 174 H c-C3H5 2-CH3-3-Cl 7-F 175 H n-C4H9 2-CH3-3-Cl 7-F 176 H s-C4H9 2-CH3-3-Cl 7-F 177 H i-C4H9 2-CH3-3-Cl 7-F 178 H t-C4H9 2-CH3-3-Cl 7-F 179 H n-C5H11 2-CH3-3-Cl 7-F 180 H neo-C5H11 2-CH3-3-Cl 7-F 181 H c-C5H9 2-CH3-3-Cl 7-F 182 H t-C5H11 2-CH3-3-Cl 7-F 183 H n-C6H13 2-CH3-3-Cl 7-F 184 H C2H5 4-OCF3 7-F 269-271 185 H i-C3H7 4-OCF3 7-F 264-266 186 H H 2,6-(C2H5)2-3-Cl 5-Cl 187 H CH3 2,6-(C2H5)2-3-Cl 5-Cl 188 H C2H5 2,6-(C2H5)2-3-Cl 5-Cl 189 H n-C3H7 2,6-(C2H5)2-3-Cl 5-Cl 235-237 190 H i-C3H7 2,6-(C2H5)2-3-Cl 5-Cl 191 H c-C3H5 2,6-(C2H5)2-3-Cl 5-Cl 192 H n-C4H9 2,6-(C2H5)2-3-Cl 5-Cl 193 H s-C4H9 2,6-(C2H5)2-3-Cl 5-Cl 194 H i-C4H9 2,6-(C2H5)2-3-Cl 5-Cl 195 H t-C4H9 2,6-(C2H5)2-3-Cl 5-Cl 196 H n-C5H11 2,6-(C2H5)2-3-Cl 5-Cl 197 H neo-C5H11 2,6-(C2H5)2-3-Cl 5-Cl 198 H c-C5H9 2,6-(C2H5)2-3-Cl 5-Cl 199 H t-C5H11 2,6-(C2H5)2-3-Cl 5-Cl 200 H CH2CH2CN 2,6-(C2H5)2-3-Cl 5-Cl 217-219 201 H CH2CH2OCH3 2,6-(C2H5)2-3-Cl 5-Cl 199-201 202 H CH3 2-CH3-3-Cl 5-Cl 203 H C2H5 2-CH3-3-Cl 5-Cl 204 H n-C3H7 2-CH3-3-Cl 5-Cl 205 H i-C3H7 2-CH3-3-Cl 5-Cl 206 H c-C3H5 2-CH3-3-Cl 5-Cl 207 H n-C4H9 2-CH3-3-Cl 5-Cl 208 H s-C4H9 2-CH3-3-Cl 5-Cl 209 H i-C4H9 2-CH3-3-Cl 5-Cl 210 H t-C4H9 2-CH3-3-Cl 5-Cl 211 H n-C5H11 2-CH3-3-Cl 5-Cl 212 H neo-C5H11 2-CH3-3-Cl 5-Cl 213 H c-C5H9 2-CH3-3-Cl 5-Cl 214 H n-C3H7 4-OCF3 5-Cl 210-212 215 H i-C3H7 4-OCF3 5-Cl 228-229 216 H H 2,6-(C2H5)2-3-Cl 6-Cl 217 H CH3 2,6-(C2H5)2-3-Cl 6-Cl 218 H C2H5 2,6-(C2H5)2-3-Cl 6-Cl 219 H n-C3H7 2,6-(C2H5)2-3-Cl 6-Cl 211-213 220 H i-C3H7 2,6-(C2H5)2-3-Cl 6-Cl 221 H c-C3H5 2,6-(C2H5)2-3-Cl 6-Cl 222 H n-C4H9 2,6-(C2H5)2-3-Cl 6-Cl 223 H s-C4H9 2,6-(C2H5)2-3-Cl 6-Cl 224 H i-C4H9 2,6-(C2H5)2-3-Cl 6-Cl 214-215 225 H t-C4H9 2,6-(C2H5)2-3-Cl 6-Cl 226 H n-C5H11 2,6-(C2H5)2-3-Cl 6-Cl 227 H neo-C5H11 2,6-(C2H5)2-3-Cl 6-Cl 228 H c-C5H9 2,6-(C2H5)2-3-Cl 6-Cl 203-204 229 H t-C5H11 2,6-(C2H5)2-3-Cl 6-Cl 230 H n-C6H13 2,6-(C2H5)2-3-Cl 6-Cl 231 H CH3 2-CH3-3-Cl 6-Cl 232 H C2H5 2-CH3-3-Cl 6-Cl 234 H n-C3H7 2-CH3-3-Cl 6-Cl 217-219 235 H i-C3H7 2-CH3-3-Cl 6-Cl 236 H c-C3H5 2-CH3-3-Cl 6-Cl 237 H n-C4H9 2-CH3-3-Cl 6-Cl 238 H s-C4H9 2-CH3-3-Cl 6-Cl 239 H i-C4H9 2-CH3-3-Cl 6-Cl 240 H t-C4H9 2-CH3-3-Cl 6-Cl 241 H n-C5H11 2-CH3-3-Cl 6-Cl 242 H neo-C5H11 2-CH3-3-Cl 6-Cl 243 H c-C5H9 2-CH3-3-Cl 6-Cl 236-238 244 H t-C5H11 2-CH3-3-Cl 6-Cl 245 H n-C6H13 2-CH3-3-Cl 6-Cl 246 H C2H5 2,6-(C2H5)2-3-Cl 7-Cl 238-240 247 H n-C3H7 2,6-(C2H5)2-3-Cl 7-Cl 248 H i-C3H7 2,6-(C2H5)2-3-Cl 7-Cl 249 H c-C3H5 2,6-(C2H5)2-3-Cl 7-Cl 250 H n-C4H9 2,6-(C2H5)2-3-Cl 7-Cl 251 H s-C4H9 2,6-(C2H5)2-3-Cl 7-Cl 252 H i-C4H9 2,6-(C2H5)2-3-Cl 7-Cl 253 H t-C4H9 2,6-(C2H5)2-3-Cl 7-Cl 254 H n-C5H11 2,6-(C2H5)2-3-Cl 7-Cl 255 H neo-C5H11 2,6-(C2H5)2-3-Cl 7-Cl 256 H c-C5H9 2,6-(C2H5)2-3-Cl 7-Cl 257 H t-C5H11 2,6-(C2H5)2-3-Cl 7-Cl 258 H n-C6H13 2,6-(C2H5)2-3-Cl 7-Cl 259 H CH3 2-CH3-3-Cl 7-Cl 260 H C2H5 2-CH3-3-Cl 7-Cl 261 H n-C3H7 2-CH3-3-Cl 7-Cl 262 H i-C3H7 2-CH3-3-Cl 7-Cl 263 H c-C3H5 2-CH3-3-Cl 7-Cl 264 H n-C4H9 2-CH3-3-Cl 7-Cl 265 H s-C4H9 2-CH3-3-Cl 7-Cl 266 H i-C4H9 2-CH3-3-Cl 7-Cl 267 H t-C4H9 2-CH3-3-Cl 7-Cl 268 H n-C5H11 2-CH3-3-Cl 7-Cl 269 H neo-C5H11 2-CH3-3-Cl 7-Cl 270 H c-C5H9 2-CH3-3-Cl 7-Cl 271 H t-C5H11 2-CH3-3-Cl 7-Cl 272 H n-C6H13 2-CH3-3-Cl 7-Cl 273 H H 2,6-(C2H5)2-3-Cl 6-OH 274 H CH3 2,6-(C2H5)2-3-Cl 6-OH 275 H C2H5 2,6-(C2H5)2-3-Cl 6-OH 239-241 276 H n-C3H7 2,6-(C2H5)2-3-Cl 6-OH 266-267 277 H i-C3H7 2,6-(C2H5)2-3-Cl 6-OH 278 H c-C3H5 2,6-(C2H5)2-3-Cl 6-OH 279 H n-C4H9 2,6-(C2H5)2-3-Cl 6-OH 280 H s-C4H9 2,6-(C2H5)2-3-Cl 6-OH 281 H i-C4H9 2,6-(C2H5)2-3-Cl 6-OH 282 H t-C4H9 2,6-(C2H5)2-3-Cl 6-OH 283 H n-C5H11 2,6-(C2H5)2-3-Cl 6-OH 284 H neo-C5H11 2,6-(C2H5)2-3-Cl 6-OH 285 H c-C5H9 2,6-(C2H5)2-3-Cl 6-OH 286 H t-C5H11 2,6-(C2H5)2-3-Cl 6-OH 287 H n-C6H13 2,6-(C2H5)2-3-Cl 6-OH 288 H CH3 2,6-(C2H5)2-3-Cl 6-OCH3 289 H C2H5 2,6-(C2H5)2-3-Cl 6-OCH3 209-210 290 H n-C3H7 2,6-(C2H5)2-3-Cl 6-OCH3 173-175 291 H i-C3H7O 2,6-(C2H5)2-3-Cl 6-OCH3 178-181 292 H c-C3H5 2,6-(C2H5)2-3-Cl 6-OCH3 293 H n-C4H9 2,6-(C2H5)2-3-Cl 6-OCH3 294 H s-C4H9 2,6-(C2H5)2-3-Cl 6-OCH3 295 H i-C4H9 2,6-(C2H5)2-3-Cl 6-OCH3 296 H t-C4H9 2,6-(C2H5)2-3-Cl 6-OCH3 297 H n-C5H11 2,6-(C2H5)2-3-Cl 6-OCH3 298 H neo-C5H11 2,6-(C2H5)2-3-Cl 6-OCH3 299 H c-C5H9 2,6-(C2H5)2-3-Cl 6-OCH3 300 H t-C5H11 2,6-(C2H5)2-3-Cl 6-OCH3 301 H n-C6H13 2,6-(C2H5)2-3-Cl 6-OCH3 302 H H 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 303 H CH3 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 304 H C2H5 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 305 H n-C3H7 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 223-225 306 H i-C3H7 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 307 H c-C3H5 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 308 H n-C4H9 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 309 H s-C4H9 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 310 H i-C4H9 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 204-206 311 H t-C4H9 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 312 H n-C5H11 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 313 H neo-C5H11 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 314 H c-C5H9 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 315 H t-C5H11 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 316 H n-C6H13 2,6-(C2H5)2-3-Cl 6,7-(OCH3)2 317 H CH3 2-CH3-3-Cl 6,7-(OCH3)2 318 H C2H5 2-CH3-3-Cl 6,7-(OCH3)2 319 H n-C3H7 2-CH3-3-Cl 6,7-(OCH3)2 320 H i-C3H7 2-CH3-3-Cl 6,7-(OCH3)2 321 H c-C3H5 2-CH3-3-Cl 6,7-(OCH3)2 322 H n-C4H9 2-CH3-3-Cl 6,7-(OCH3)2 323 H s-C4H9 2-CH3-3-Cl 6,7-(OCH3)2 324 H i-C4H9 2-CH3-3-Cl 6,7-(OCH3)2 325 H t-C4H9 2-CH3-3-Cl 6,7-(OCH3)2 326 H n-C5H11 2-CH3-3-Cl 6,7-(OCH3)2 327 H neo-C5H11 2-CH3-3-Cl 6,7-(OCH3)2 328 H c-C5H9 2-CH3-3-Cl 6,7-(OCH3)2 329 H t-C5H11 2-CH3-3-Cl 6,7-(OCH3)2 330 H n-C6H13 2-CH3-3-Cl 6,7-(OCH3)2 331 H H 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 332 H CH3 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 333 H C2H5 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 334 H n-C3H7 2,6-(C2H5)2-3-Cl 6,7- 213-215 (OCH2O) 335 H i-C3H7 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 336 H c-C3H5 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 337 H n-C4H9 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 338 H s-C4H9 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 339 H i-C4H9 2,6-(C2H5)2-3-Cl 6,7- 221-223 (OCH2O) 340 H t-C4H9 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 341 H n-C5H11 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 342 H neo-C5H11 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 343 H c-C5H9 2,6-(C2H5)2-3-Cl 6,7- 191-193 (OCH2O) 344 H t-C5H11 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 345 H n-C6H13 2,6-(C2H5)2-3-Cl 6,7- (OCH2O) 346 H CH3 2-CH3-3-Cl 6,7- (OCH2O) 347 H C2H5 2-CH3-3-Cl 6,7- (OCH2O) 348 H n-C3H7 2-CH3-3-Cl 6,7- (OCH2O) 349 H i-C3H7 2-CH3-3-Cl 6,7- (OCH2O) 350 H c-C3H5 2-CH3-3-Cl 6,7- (OCH2O) 351 H n-C4H9 2-CH3-3-Cl 6,7- (OCH2O) 352 H s-C4H9 2-CH3-3-Cl 6,7- (OCH2O) 353 H i-C4H9 2-CH3-3-Cl 6,7- (OCH2O) 354 H t-C4H9 2-CH3-3-Cl 6,7- (OCH2O) 355 H n-C5H11 2-CH3-3-Cl 6,7- (OCH2O) 356 H neo-C5H11 2-CH3-3-Cl 6,7- (OCH2O) 357 H c-C5H9 2-CH3-3-Cl 6,7- (OCH2O) 358 H t-C5H11 2-CH3-3-Cl 6,7- (OCH2O) 359 H n-C6H13 2-CH3-3-Cl 6,7- (OCH2O) 359-1 H CH3 2,6-(C2H5)2-3-Cl H 235-237 359-2 H C2H5 2,6-(C2H5)2-3-Cl H 205-207 359-3 H n-C3H7 2,6-(C2H5)2-3-Cl H 211-213 359-4 H t-C4H9 2,6-(C2H5)2-3-Cl H 195-197 359-5 H neo-C5H11 2,6-(C2H5)2-3-Cl H 141-143 359-6 H c-C5H9 2,6-(C2H5)2-3-Cl H 161-163

[0268] 2 TABLE 2 26 No R2 R3 X A E mp ° C. 360 H C2H5 2,6-(C2H5)2-3-Cl N CH 249-264 361 H n-C3H7 2,6-(C2H5)2-3-Cl N CH 234-250 362 H i-C3H7 2,6-(C2H5)2-3-Cl N CH 363 H c-C3H7 2,6-(C2H5)2-3-Cl N CH 364 H n-C4H9 2,6-(C2H5)2-3-Cl N CH 365 H s-C4H9 2,6-(C2H5)2-3-Cl N CH 366 H i-C4H9 2,6-(C2H5)2-3-Cl N CH 367 H t-C4H9 2,6-(C2H5)2-3-Cl N CH 368 H n-C5H11 2,6-(C2H5)2-3-Cl N CH 369 H neo-C5H11 2,6-(C2H5)2-3-Cl N CH 370 H c-C5H9 2,6-(C2H5)2-3-Cl N CH 371 H t-C5H11 2,6-(C2H5)2-3-Cl N CH 372 H n-C6H13 2,6-(C2H5)2-3-Cl N CH 373 H CH3 2-CH3-3-Cl N CH 374 H C2H5 2-CH3-3-Cl N CH 375 H n-C3H7 2-CH3-3-Cl N CH 223-245 376 H i-C3H7 2-CH3-3-Cl N CH 377 H c-C3H5 2-CH3-3-Cl N CH 378 H n-C4H9 2-CH3-3-Cl N CH 379 H s-C4H9 2-CH3-3-Cl N CH 380 H i-C4H9 2-CH3-3-Cl N CH 381 H t-C4H9 2-CH3-3-Cl N CH 382 H n-C5H11 2-CH3-3-Cl N CH 383 H neo-C5H11 2-CH3-3-Cl N CH 384 H c-C5H9 2-CH3-3-Cl N CH 385 H t-C5H11 2-CH3-3-Cl N CH 386 H n-C6H13 2-CH3-3-Cl N CH 387 H C2H5 2,6-(C2H5)2-3-Cl N N 388 H n-C3H7 2,6-(C2H5)2-3-Cl N N 215-220 389 H i-C3H7 2,6-(C2H5)2-3-Cl N N 390 H c-C3H5 2,6-(C2H5)2-3-Cl N N 391 H n-C4H9 2,6-(C2H5)2-3-Cl N N 392 H s-C4H9 2,6-(C2H5)2-3-Cl N N 393 H i-C4H9 2,6-(C2H5)2-3-Cl N N 394 H t-C4H9 2,6-(C2H5)2-3-Cl N N 395 H n-C5H11 2,6-(C2H5)2-3-Cl N N 396 H neo-C5H11 2,6-(C2H5)2-3-Cl N N 397 H c-C5H9 2,6-(C2H5)2-3-Cl N N 398 H t-C5H11 2,6-(C2H5)2-3-Cl N N 399 H n-C6H13 2,6-(C2H5)2-3-Cl N N 400 H CH3 2-CH3-3-Cl N N 401 H C2H5 2-CH3-3-Cl N N 402 H n-C3H7 2-CH3-3-Cl N N 403 H i-C3H7 2-CH3-3-Cl N N 404 H c-C3H5 2-CH3-3-Cl N N 405 H n-C4H9 2-CH3-3-Cl N N 406 H s-C4H9 2-CH3-3-Cl N N 407 H i-C4H9 2-CH3-3-Cl N N 408 H t-C4H9 2-CH3-3-Cl N N 409 H n-C5H11 2-CH3-3-Cl N N 410 H neo-C5H11 2-CH3-3-Cl N N 411 H c-C5H9 2-CH3-3-Cl N N 412 H t-C5H11 2-CH3-3-Cl N N

[0269] 3 TABLE 3 27 No R3 X F G J K mp ° C. 413 C2H5 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 414 n-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 188-191 415 i-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 416 c-C3H5 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 417 n-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 418 s-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 419 i-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 420 t-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 421 n-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 422 neo-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 423 c-C5H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 185-189 424 t-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 CH2 425 C2H5 2-CH3-3-Cl O CH2 CH2 CH2 426 n-C3H7 2-CH3-3-Cl O CH2 CH2 CH2 427 i-C3H7 2-CH3-3-Cl O CH2 CH2 CH2 428 c-C3H5 2-CH3-3-Cl O CH2 CH2 CH2 429 n-C4H9 2-CH3-3-Cl O CH2 CH2 CH2 430 s-C4H9 2-CH3-3-Cl O CH2 CH2 CH2 431 i-C4H9 2-CH3-3-Cl O CH2 CH2 CH2 180-183 432 t-C4H9 2-CH3-3-Cl O CH2 CH2 CH2 433 n-C5H11 2-CH3-3-Cl O CH2 CH2 CH2 434 neo-C5H11 2-CH3-3-Cl O CH2 CH2 CH2 435 c-C5H9 2-CH3-3-Cl O CH2 CH2 CH2 436 t-C5H11 2-CH3-3-Cl O CH2 CH2 CH2 437 C2H5 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 438 n-C3H7 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 190-194 439 i-C3H7 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 440 c-C3H5 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 441 n-C4H9 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 442 s-C4H9 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 443 i-C4H9 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 444 t-C4H9 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 445 n-C5H11 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 446 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 447 c-C5H9 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 187-190 448 t-C5H11 2,6-(C2H5)2-3-Cl CH2 O CH2 CH2 449 C2H5 2-CH3-3-Cl CH2 O CH2 CH2 450 n-C3H7 2-CH3-3-Cl CH2 O CH2 CH2 188-190 451 i-C3H7 2-CH3-3-Cl CH2 O CH2 CH2 452 c-C3H5 2-CH3-3-Cl CH2 O CH2 CH2 453 n-C4H9 2-CH3-3-Cl CH2 O CH2 CH2 454 s-C4H9 2-CH3-3-Cl CH2 O CH2 CH2 455 i-C4H9 2-CH3-3-Cl CH2 O CH2 CH2 456 t-C4H9 2-CH3-3-Cl CH2 O CH2 CH2 457 n-C5H11 2-CH3-3-Cl CH2 O CH2 CH2 458 neo-C5H11 2-CH3-3-Cl CH2 O CH2 CH2 459 c-C5H9 2-CH3-3-Cl CH2 O CH2 CH2 460 t-C5H11 2-CH3-3-Cl CH2 O CH2 CH2 461 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 462 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 166-170 463 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 464 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 465 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 466 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 467 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 468 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 469 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 470 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 471 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 472 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 O CH2 473 C2H5 2-CH3-3-Cl CH2 CH2 O CH2 474 n-C3H7 2-CH3-3-Cl CH2 CH2 O CH2 168-171 475 i-C3H7 2-CH3-3-Cl CH2 CH2 O CH2 476 c-C3H5 2-CH3-3-Cl CH2 CH2 O CH2 477 n-C4H9 2-CH3-3-Cl CH2 CH2 O CH2 478 s-C4H9 2-CH3-3-Cl CH2 CH2 O CH2 479 i-C4H9 2-CH3-3-Cl CH2 CH2 O CH2 480 t-C4H9 2-CH3-3-Cl CH2 CH2 O CH2 481 n-C5H11 2-CH3-3-Cl CH2 CH2 O CH2 482 neo-C5H11 2-CH3-3-Cl CH2 CH2 O CH2 483 c-C5H9 2-CH3-3-Cl CH2 CH2 O CH2 484 t-C5H11 2-CH3-3-Cl CH2 CH2 O CH2 485 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 486 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 194-196 487 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 488 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 489 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 490 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 491 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 492 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 493 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 494 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 495 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 496 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 O 497 C2H5 2-CH3-3-Cl CH2 CH2 CH2 O 498 n-C3H7 2-CH3-3-Cl CH2 CH2 CH2 O 195-198 499 i-C3H7 2-CH3-3-Cl CH2 CH2 CH2 O 500 c-C3H5 2-CH3-3-Cl CH2 CH2 CH2 O 501 n-C4H9 2-CH3-3-Cl CH2 CH2 CH2 O 502 s-C4H9 2-CH3-3-Cl CH2 CH2 CH2 O 503 i-C4H9 2-CH3-3-Cl CH2 CH2 CH2 O 504 t-C4H9 2-CH3-3-Cl CH2 CH2 CH2 O 505 n-C5H11 2-CH3-3-Cl CH2 CH2 CH2 O 506 neo-C5H11 2-CH3-3-Cl CH2 CH2 CH2 O 507 c-C5H9 2-CH3-3-Cl CH2 CH2 CH2 O 508 t-C5H11 2-CH3-3-Cl CH2 CH2 CH2 O 509 C2H5 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 510 n-C3H7 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 181-183 511 i-C3H7 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 512 c-C3H5 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 513 n-C4H9 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 514 s-C4H9 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 515 i-C4H9 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 516 t-C4H9 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 517 n-C5H11 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 518 neo-C5H11 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 519 c-C5H9 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 175-180 520 t-C5H11 2,6-(C2H5)2-3-Cl S CH2 CH2 CH2 521 C2H5 2-CH3-3-Cl S CH2 CH2 CH2 522 n-C3H7 2-CH3-3-Cl S CH2 CH2 CH2 523 i-C3H7 2-CH3-3-Cl S CH2 CH2 CH2 524 c-C3H5 2-CH3-3-Cl S CH2 CH2 CH2 525 n-C4H9 2-CH3-3-Cl S CH2 CH2 CH2 526 s-C4H9 2-CH3-3-Cl S CH2 CH2 CH2 527 i-C4H9 2-CH3-3-Cl S CH2 CH2 CH2 178-181 528 t-C4H9 2-CH3-3-Cl S CH2 CH2 CH2 529 n-C5H11 2-CH3-3-Cl S CH2 CH2 CH2 530 neo-C5H11 2-CH3-3-Cl S CH2 CH2 CH2 531 c-C5H9 2-CH3-3-Cl S CH2 CH2 CH2 532 t-C5H11 2-CH3-3-Cl S CH2 CH2 CH2 533 C2H5 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 534 n-C3H7 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 180-184 535 i-C3H7 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 536 c-C3H5 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 537 n-C4H9 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 538 s-C4H9 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 539 i-C4H9 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 540 t-C4H9 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 541 n-C5H11 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 542 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 543 c-C5H9 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 544 t-C5H11 2,6-(C2H5)2-3-Cl CH2 S CH2 CH2 545 C2H5 2-CH3-3-Cl CH2 S CH2 CH2 546 n-C3H7 2-CH3-3-Cl CH2 S CH2 CH2 547 i-C3H7 2-CH3-3-Cl CH2 S CH2 CH2 548 c-C3H5 2-CH3-3-Cl CH2 S CH2 CH2 549 n-C4H9 2-CH3-3-Cl CH2 S CH2 CH2 550 s-C4H9 2-CH3-3-Cl CH2 S CH2 CH2 551 i-C4H9 2-CH3-3-Cl CH2 S CH2 CH2 552 t-C4H9 2-CH3-3-Cl CH2 S CH2 CH2 553 n-C5H11 2-CH3-3-Cl CH2 S CH2 CH2 554 neo-C5H11 2-CH3-3-Cl CH2 S CH2 CH2 555 c-C5H9 2-CH3-3-Cl CH2 S CH2 CH2 556 t-C5H11 2-CH3-3-Cl CH2 S CH2 CH2 557 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 558 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 179-180 559 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 560 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 561 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 562 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 563 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 564 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 565 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 566 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 567 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 568 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 S CH2 569 C2H5 2-CH3-3-Cl CH2 CH2 S CH2 570 n-C3H7 2-CH2-3-Cl CH2 CH2 S CH2 182-185 571 i-C3H7 2-CH3-3-Cl CH2 CH2 S CH2 572 c-C3H5 2-CH3-3-Cl CH2 CH2 S CH2 573 n-C4H9 2-CH3-3-Cl CH2 CH2 S CH2 574 s-C4H9 2-CH3-3-Cl CH2 CH2 S CH2 575 i-C4H9 2-CH3-3-Cl CH2 CH2 S CH2 576 t-C4H9 2-CH3-3-Cl CH2 CH2 S CH2 577 n-C5H11 2-CH3-3-Cl CH2 CH2 S CH2 578 neo-C5H11 2-CH3-3-Cl CH2 CH2 S CH2 579 c-C5H9 2-CH3-3-Cl CH2 CH2 S CH2 580 t-C5H11 2-CH3-3-Cl CH2 CH2 S CH2 581 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 582 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 186-190 583 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 584 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 585 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 586 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 587 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 588 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 589 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 590 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 591 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 592 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 S 593 C2H5 2-CH3-3-Cl CH2 CH2 CH2 S 594 n-C3H7 2-CH3-3-Cl CH2 CH2 CH2 S 595 i-C3H7 2-CH3-3-Cl CH2 CH2 CH2 S 596 c-C3H5 2-CH3-3-Cl CH2 CH2 CH2 S 597 n-C4H9 2-CH3-3-Cl CH2 CH2 CH2 S 598 s-C4H9 2-CH3-3-Cl CH2 CH2 CH2 S 599 i-C4H9 2-CH3-3-Cl CH2 CH2 CH2 S 600 t-C4H9 2-CH3-3-Cl CH2 CH3 CH2 S 601 n-C5H11 2-CH3-3-Cl CH2 CH2 CH2 S 602 neo-C5H11 2-CH3-3-Cl CH2 CH2 CH2 S 603 c-C5H9 2-CH3-3-Cl CH2 CH2 CH2 S 604 t-C5H11 2-CH3-3-Cl CH2 CH2 CH2 S 605 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 606 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2  93-100 607 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 608 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 609 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 610 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 611 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 612 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 613 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 614 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 615 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 616 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO CH2 617 C2H5 2-CH3-3-Cl CH2 CH2 SO CH2 618 n-C3H7 2-CH3-3-Cl CH2 CH2 SO CH2 619 i-C3H7 2-CH3-3-Cl CH2 CH2 SO CH2 620 c-C3H5 2-CH3-3-Cl CH2 CH2 SO CH2 621 n-C4H9 2-CH3-3-Cl CH2 CH2 SO CH2 622 s-C4H9 2-CH3-3-Cl CH2 CH2 SO CH2 623 i-C4H9 2-CH3-3-Cl CH2 CH2 SO CH2 624 t-C4H9 2-CH3-3-Cl CH2 CH2 SO CH2 625 n-C5H11 2-CH3-3-Cl CH2 CH2 SO CH2 626 neo-C5H11 2-CH3-3-Cl CH2 CH2 SO CH2 627 c-C5H9 2-CH3-3-Cl CH2 CH2 SO CH2 628 t-C5H11 2-CH3-3-Cl CH2 CH2 SO CH2 629 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 630 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 86-96 631 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 632 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 633 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 634 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 635 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 636 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 637 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 638 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 639 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 640 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 CH2 641 C2H5 2-CH3-3-Cl CH2 CH2 SO2 CH2 642 n-C3H7 2-CH3-3-Cl CH2 CH2 SO2 CH2 643 i-C3H7 2-CH3-3-Cl CH2 CH2 SO2 CH2 644 c-C3H5 2-CH3-3-Cl CH2 CH2 SO2 CH2 645 n-C4H9 2-CH3-3-Cl CH2 CH2 SO2 CH2 646 s-C4H9 2-CH3-3-Cl CH2 CH2 SO2 CH2 647 i-C4H9 2-CH3-3-Cl CH2 CH2 SO2 CH2 648 t-C4H9 2-CH3-3-Cl CH2 CH2 SO2 CH2 649 n-C5H11 2-CH3-3-Cl CH2 CH2 SO2 CH2 650 neo-C5H11 2-CH3-3-Cl CH2 CH2 SO2 CH2 651 c-C5H9 2-CH3-3-Cl CH2 CH2 SO2 CH2 652 t-C5H11 2-CH3-3-Cl CH2 CH2 SO2 CH2 653 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 654 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 Refractive index 1.4764 (20° C.) 655 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 656 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 657 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 658 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 659 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 660 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 661 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 662 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 663 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 664 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 CH2 665 C2H5 2-CH3-3-Cl CH2 CH2 NCH3 CH2 667 n-C3H7 2-CH3-3-Cl CH2 CH2 NCH3 CH2 668 i-C3H7 2-CH3-3-Cl CH2 CH2 NCH3 CH2 669 c-C3H5 2-CH3-3-Cl CH2 CH2 NCH3 CH2 670 n-C4H9 2-CH3-3-Cl CH2 CH2 NCH3 CH2 671 s-C4H9 2-CH3-3-Cl CH2 CH2 NCH3 CH2 672 i-C4H9 2-CH3-3-Cl CH2 CH2 NCH3 CH2 673 t-C4H9 2-CH3-3-Cl CH2 CH2 NCH3 CH2 674 n-C5H11 2-CH3-3-Cl CH2 CH2 NCH3 CH2 675 neo-C5H11 2-CH3-3-Cl CH2 CH2 NCH3 CH2 676 c-C5H9 2-CH3-3-Cl CH2 CH2 NCH3 CH2 677 t-C5H11 2-CH3-3-Cl CH2 CH2 NCH3 CH2 678 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 212-213 679 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 214-215 680 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 681 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 682 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 683 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 684 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 685 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 686 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 687 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 688 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 689 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 CH2 CO 690 C2H5 2-CH3-3-Cl CH2 CH2 CH2 CO 691 n-C3H7 2-CH3-3-Cl CH2 CH2 CH2 CO 692 i-C3H7 2-CH3-3-Cl CH2 CH2 CH2 CO 693 c-C3H5 2-CH3-3-Cl CH2 CH2 CH2 CO 694 n-C4H9 2-CH3-3-Cl CH2 CH2 CH2 CO 695 s-C4H9 2-CH3-3-Cl CH2 CH2 CH2 CO 696 i-C4H9 2-CH3-3-Cl CH2 CH2 CH2 CO 697 t-C4H9 2-CH3-3-Cl CH2 CH2 CH2 CO 698 n-C5H11 2-CH3-3-Cl CH2 CH2 CH2 CO 699 neo-C5H11 2-CH3-3-Cl CH2 CH2 CH2 CO 700 c-C5H9 2-CH3-3-Cl CH2 CH2 CH2 CO 701 t-C5H11 2-CH3-3-Cl CH2 CH2 CH2 CO 702 C2H5 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 703 n-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 185-188 704 i-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 705 c-C3H5 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 706 n-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 707 s-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 708 i-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 709 t-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 710 n-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 711 neo-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 712 c-C5H9 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 713 t-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 CO 714 C2H5 2-CH3-3-Cl O CH2 CH2 CO 715 n-C3H7 2-CH3-3-Cl O CH2 CH2 CO 716 i-C3H7 2-CH3-3-Cl O CH2 CH2 CO 717 c-C3H5 2-CH3-3-Cl O CH2 CH2 CO 718 n-C4H9 2-CH3-3-Cl O CH2 CH2 CO 719 s-C4H9 2-CH3-3-Cl O CH2 CH2 CO 720 i-C4H9 2-CH3-3-Cl O CH2 CH2 CO 721 t-C4H9 2-CH3-3-Cl O CH2 CH2 CO 722 n-C5H11 2-CH3-3-Cl O CH2 CH2 CO 723 neo-C5H11 2-CH3-3-Cl O CH2 CH2 CO 724 c-C5H9 2-CH3-3-Cl O CH2 CH2 CO 189-192 725 t-C5H11 2-CH3-3-Cl O CH2 CH2 CO 726 C2H5 2,6-(C2H5)2-3-Cl O CH═CH CO 727 n-C3H7 2,6-(C2H5)2-3-Cl O CH═CH CO 198-201 728 i-C3H7 2,6-(C2H5)2-3-Cl O CH═CH CO 729 c-C3H5 2,6-(C2H5)2-3-Cl O CH═CH CO 730 n-C4H9 2,6-(C2H5)2-3-Cl O CH═CH CO 731 s-C4H9 2,6-(C2H5)2-3-Cl O CH═CH CO 732 i-C4H9 2,6-(C2H5)2-3-Cl O CH═CH CO 733 t-C4H9 2,6-(C2H5)2-3-Cl O CH═CH CO 734 n-C5H11 2,6-(C2H5)2-3-Cl O CH═CH CO 735 neo-C5H11 2,6-(C2H5)2-3-Cl O CH═CH CO 736 c-C5H9 2,6-(C2H5)2-3-Cl O CH═CH CO 737 t-C5H11 2,6-(C2H5)2-3-Cl O CH═CH CO 738 C2H5 2,6-(C2H5)2-3-Cl O CH2 CH2 O 739 n-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 O 173-175 740 i-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 O 741 c-C3H5 2,6-(C2H5)2-3-Cl O CH2 CH2 O 742 n-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 O 743 s-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 O 744 i-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 O 745 t-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 O 746 n-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 O 747 neo-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 O 748 c-C5H9 2,6-(C2H5)2-3-Cl O CH2 CH2 O 749 t-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 O 750 C2H5 2-CH3-3-Cl O CH2 CH2 O 751 n-C3H7 2-CH3-3-Cl O CH2 CH2 O 752 i-C3H7 2-CH3-3-Cl O CH2 CH2 O 753 c-C3H5 2-CH3-3-Cl O CH2 CH2 O 754 n-C4H9 2-CH3-3-Cl O CH2 CH2 O 755 s-C4H9 2-CH3-3-Cl O CH2 CH2 O 756 i-C4H9 2-CH3-3-Cl O CH2 CH2 O 757 t-C4H9 2-CH3-3-Cl O CH2 CH2 O 758 n-C5H11 2-CH3-3-Cl O CH2 CH2 O 759 neo-C5H11 2-CH3-3-Cl O CH2 CH2 O 760 c-C5H9 2-CH3-3-Cl O CH2 CH2 O 179-182 761 t-C5H11 2-CH3-3-Cl O CH2 CH2 O 762 C2H5 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 763 n-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 153-155 764 i-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 765 c-C3H5 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 766 n-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 767 s-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 768 i-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 769 t-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 770 n-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 771 neo-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 772 c-C5H9 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3 773 t-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 NCH3

[0270] 4 TABLE 4 28 No R3 X (R9)m Z mp ° C. 774 C2H5 2,6-(C2H5)2-3-Cl H O 226-229 775 n-C3H7 2,6-(C2H5)2-3-Cl H O 192-193 776 i-C3H7 2,6-(C2H5)2-3-Cl H O 777 c-C3H5 2,6-(C2H5)2-3-Cl H O 778 n-C4H9 2,6-(C2H5)2-3-Cl H O 779 s-C4H9 2,6-(C2H5)2-3-Cl H O 780 i-C4H9 2,6-(C2H5)2-3-Cl H O 781 t-C4H9 2,6-(C2H5)2-3-Cl H O 782 n-C5H11 2,6-(C2H5)2-3-Cl H O 783 neo-C5H11 2,6-(C2H5)2-3-Cl H O 784 c-C5H9 2,6-(C2H5)2-3-Cl H O 785 t-C5H11 2,6-(C2H5)2-3-Cl H O 786 C2H5 2-CH3-3-Cl H O 787 n-C3H7 2-CH3-3-Cl H O 788 i-C4H9 2-CH3-3-Cl H O 789 c-C3H5 2-CH3-3-Cl H O 790 n-C4H9 2-CH3-3-Cl H O 791 s-C4H9 2-CH3-3-Cl H O 792 i-C4H9 2-CH3-3-Cl H O 793 t-C4H9 2-CH3-3-Cl H O 794 n-C5H11 2-CH3-3-Cl H O 795 neo-C5H11 2-CH3-3-Cl H O 796 c-C5H9 2-CH3-3-Cl H O 198-200 797 t-C5H11 2-CH3-3-Cl H O 798 C2H5 2,6-(C2H5)2-3-Cl H S 225-229 799 n-C3H7 2,6-(C2H5)2-3-Cl H S 194-196 800 i-C3H7 2,6-(C2H5)2-3-Cl H S 801 c-C3H5 2,6-(C2H5)2-3-Cl H S 802 n-C4H9 2,6-(C2H5)2-3-Cl H S 803 s-C4H9 2,6-(C2H5)2-3-Cl H S 804 i-C4H9 2,6-(C2H5)2-3-Cl H S 805 t-C4H9 2,6-(C2H5)2-3-Cl H S 806 n-C5H11 2,6-(C2H5)2-3-Cl H S 807 neo-C5H11 2,6-(C2H5)2-3-Cl H S 808 c-C5H9 2,6-(C2H5)2-3-Cl H S 809 t-C5H11 2,6-(C2H5)2-3-Cl H S 810 neo-C5H11 2-CH3-3-Cl H S 811 c-C5H9 2-CH3-3-Cl H S 197-199 812 t-C5H11 2-CH3-3-Cl H S 813 C2H5 2,6-(C2H5)2-3-Cl 3-Br S 814 n-C3H7 2,6-(C2H5)2-3-Cl 3-Br S 187-190 815 i-C3H7 2,6-(C2H5)2-3-Cl 3-Br S 816 c-C3H5 2,6-(C2H5)2-3-Cl 3-Br S 817 n-C4H9 2,6-(C2H5)2-3-Cl 3-Br S 818 s-C4H9 2,6-(C2H5)2-3-Cl 3-Br S 819 i-C4H9 2,6-(C2H5)2-3-Cl 3-Br S 820 t-C4H9 2,6-(C2H5)2-3-Cl 3-Br S 821 neo-C5H11 2,6-(C2H5)2-3-Cl 3-Br S 822 c-C5H9 2,6-(C2H5)2-3-Cl 3-Br S 823 C2H5 2,6-(C2H5)2-3-Cl H NCH3 824 n-C3H7 2,6-(C2H5)2-3-Cl H NCH3 166-169 825 i-C3H7 2,6-(C2H5)2-3-Cl H NCH3 826 c-C3H5 2,6-(C2H5)2-3-Cl H NCH3 827 n-C4H9 2,6-(C2H5)2-3-Cl H NCH3 828 s-C4H9 2,6-(C2H5)2-3-Cl H NCH3 829 i-C4H9 2,6-(C2H5)2-3-Cl H NCH3 830 t-C4H9 2,6-(C2H5)2-3-Cl H NCH3 831 n-C5H11 2,6-(C2H5)2-3-Cl H NCH3 832 neo-C5H11 2,6-(C2H5)2-3-Cl H NCH3 833 c-C5H9 2,6-(C2H5)2-3-Cl H NCH3 834 t-C5H11 2,6-(C2H5)2-3-Cl H NCH3

[0271] 5 TABLE 5 29 No R3 X (R9)m Z mp ° C. 835 C2H5 2,6-(C2H5)2-3-Cl H S 836 n-C3H7 2,6-(C2H5)2-3-Cl H S 837 i-C3H7 2,6-(C2H5)2-3-Cl H S 198-201 838 c-C3H5 2,6-(C2H5)2-3-Cl H S 839 n-C4H9 2,6-(C2H5)2-3-Cl H S 840 s-C4H9 2,6-(C2H5)2-3-Cl H S 841 i-C4H9 2,6-(C2H5)2-3-Cl H S 842 t-C4H9 2,6-(C2H5)2-3-Cl H S 843 n-C5H11 2,6-(C2H5)2-3-Cl H S 844 neo-C5H11 2,6-(C2H5)2-3-Cl H S 845 c-C5H9 2,6-(C2H5)2-3-Cl H S

[0272] 6 TABLE 6 30 No R3 X (R9)m Z mp ° C. 846 C2H5 2,6-(C2H5)2-3-Cl H O 847 n-C3H7 2,6-(C2H5)2-3-Cl H O 198-201 848 i-C3H7 2,6-(C2H5)2-3-Cl H O 849 c-C3H5 2,6-(C2H5)2-3-Cl H O 850 n-C4H9 2,6-(C2H5)2-3-Cl H O 851 s-C4H9 2,6-(C2H5)2-3-Cl H O 852 i-C4H9 2,6-(C2H5)2-3-Cl H O 853 t-C4H9 2,6-(C2H5)2-3-Cl H O 854 n-C5H11 2,6-(C2H5)2-3-Cl H O 855 neo-C5H11 2,6-(C2H5)2-3-Cl H O 856 c-C5H9 2,6-(C2H5)2-3-Cl H O 857 t-C5H11 2,6-(C2H5)2-3-Cl H O 858 C2H5 2-CH3-3-Cl H O 859 n-C3H7 2-CH3-3-Cl H O 860 i-C3H7 2-CH3-3-Cl H O 861 c-C3H5 2-CH3-3-Cl H O 862 n-C4H9 2-CH3-3-Cl H O 863 s-C4H9 2-CH3-3-Cl H O 864 i-C4H9 2-CH3-3-Cl H O 865 t-C4H9 2-CH3-3-Cl H O 866 n-C5H11 2-CH3-3-Cl H O 867 neo-C5H11 2-CH3-3-Cl H O 868 c-C5H9 2-CH3-3-Cl H O 869 t-C5H11 2-CH3-3-Cl H O 870 C2H5 2,6-(C2H5)2-3-Cl H S 213-214 871 n-C3H7 2,6-(C2H5)2-3-Cl H S 200-202 872 i-C3H7 2,6-(C2H5)2-3-Cl H S 873 c-C3H5 2,6-(C2H5)2-3-Cl H S 874 n-C4H9 2,6-(C2H5)2-3-Cl H S 875 s-C4H9 2,6-(C2H5)2-3-Cl H S 876 i-C4H9 2,6-(C2H5)2-3-Cl H S 877 t-C4H9 2,6-(C2H5)2-3-Cl H S 878 n-C5H11 2,6-(C2H5)2-3-Cl H S 879 neo-C3H11 2,6-(C2H5)2-3-Cl H S 880 c-C5H9 2,6-(C2H5)2-3-Cl H S 881 t-C5H11 2,6-(C2H5)2-3-Cl H S 882 C2H5 2-CH3-3-Cl H S 883 n-C3H7 2-CH3-3-Cl H S 884 i-C3H7 2-CH3-3-Cl H S 885 c-C3H5 2-CH3-3-Cl H S 886 n-C4H9 2-CH3-3-Cl H S 887 s-C4H9 2-CH3-3-Cl H S 888 i-C4H9 2-CH3-3-Cl H S 889 t-C4H9 2-CH3-3-Cl H S 890 n-C5H11 2-CH3-3-Cl H S 891 neo-C5H11 2-CH3-3-Cl H S 892 c-C5H9 2-CH3-3-Cl H S 206-208 893 t-C5H11 2-CH3-3-Cl H S 894 C2H5 2,6-(C2H5)2-3-Cl H NOCH3 151-153 895 n-C3H7 2,6-(C2H5)2-3-Cl H NOCH3 171-173 896 i-C3H7 2,6-(C2H5)2-3-Cl H NOCH3 897 c-C3H5 2,6-(C2H5)2-3-Cl H NOCH3 898 n-C4H9 2,6-(C2H5)2-3-Cl H NOCH3 899 s-C4H9 2,6-(C2H5)2-3-Cl H NOCH3 900 i-C4H9 2,6-(C2H5)2-3-Cl H NOCH3 901 t-C4H9 2,6-(C2H5)2-3-Cl H NOCH3 902 n-C5H11 2,6-(C2H5)2-3-Cl H NOCH3 903 neo-C5H11 2,6-(C2H5)2-3-Cl H NOCH3 904 c-C5H9 2,6-(C2H5)2-3-Cl H NOCH3 905 t-C5H11 2,6-(C2H5)2-3-Cl H NOCH3 906 C2H5 2,6-(C2H5)2-3-Cl H NCH3 907 n-C3H7 2,6-(C2H5)2-3-Cl H NCH3 151-153 908 i-C3H7 2,6-(C2H5)2-3-Cl H NCH3 909 c-C3H5 2,6-(C2H5)2-3-Cl H NCH3 910 n-C4H9 2,6-(C2H5)2-3-Cl H NCH3 911 s-C4H9 2,6-(C2H5)2-3-Cl H NCH3 912 i-C4H9 2,6-(C2H5)2-3-Cl H NCH3 913 t-C4H9 2,6-(C2H5)2-3-Cl H NCH3 914 n-C5H11 2,6-(C2H5)2-3-Cl H NCH3 915 neo-C5H11 2,6-(C2H5)2-3-Cl H NCH3 916 c-C5H9 2,6-(C2H5)2-3-Cl H NCH3 917 t-C5H11 2,6-(C2H5)2-3-Cl H NCH3

[0273] 7 TABLE 7 31 mp No R3 X L M T ° C. 918 C2H5 2,6-(C2H5)2-3-Cl O CH2 CH2 919 n-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 177- 180 920 i-C3H7 2,6-(C2H5)2-3-Cl O CH2 CH2 921 c-C3H5 2,6-(C2H5)2-3-Cl O CH2 CH2 922 n-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 923 s-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 924 i-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 925 t-C4H9 2,6-(C2H5)2-3-Cl O CH2 CH2 926 n-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 927 neo-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 928 c-C5H9 2,6-(C2H5)2-3-Cl O CH2 CH2 929 t-C5H11 2,6-(C2H5)2-3-Cl O CH2 CH2 930 neo-C5H11 2-CH3-3-Cl O CH2 CH2 931 c-C5H9 2-CH3-3-Cl O CH2 CH2 932 t-C5H11 2-CH3-3-Cl O CH2 CH2 933 C2H5 2,6-(C2H5)2-3-Cl CH2 O CH2 934 n-C3H7 2,6-(C2H5)2-3-Cl CH2 O CH2 179- 181 935 i-C3H7 2,6-(C2H5)2-3-Cl CH2 O CH2 936 c-C3H5 2,6-(C2H5)2-3-Cl CH2 O CH2 937 n-C4H9 2,6-(C2H5)2-3-Cl CH2 O CH2 938 s-C4H9 2,6-(C2H5)2-3-Cl CH2 O CH2 939 i-C4H9 2,6-(C2H5)2-3-Cl CH2 O CH2 940 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 O CH2 941 c-C5H9 2,6-(C2H5)2-3-Cl CH2 O CH2 942 C2H5 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 943 n-C3H7 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 163- 165 944 i-C3H7 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 945 c-C3H5 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 946 n-C4H9 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 947 s-C4H9 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 948 i-C4H9 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 949 t-C4H9 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 950 n-C5H11 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 951 neo-C5H11 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 952 c-C5H9 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 953 t-C5H11 2,6-(C2H5)2-3-Cl O CH2 CHOCH3 954 C2H5 2,6-(C2H5)2-3-Cl S CH2 CH2 955 n-C3H7 2,6-(C2H5)2-3-Cl S CH2 CH2 167- 171 956 i-C3H7 2,6-(C2H5)2-3-Cl S CH2 CH2 957 c-C3H5 2,6-(C2H5)2-3-Cl S CH2 CH2 958 n-C4H9 2,6-(C2H5)2-3-Cl S CH2 CH2 959 s-C4H9 2,6-(C2H5)2-3-Cl S CH2 CH2 960 i-C4H9 2,6-(C2H5)2-3-Cl S CH2 CH2 961 t-C4H9 2,6-(C2H5)2-3-Cl S CH2 CH2 962 n-C5H11 2,6-(C2H5)2-3-Cl S CH2 CH2 963 neo-C5H11 2,6-(C2H5)2-3-Cl S CH2 CH2 964 c-C5H9 2,6-(C2H5)2-3-Cl S CH2 CH2 965 t-C5H11 2,6-(C2H5)2-3-Cl S CH2 CH2 966 C2H5 2-CH3-3-Cl S CH2 CH2 967 n-C3H7 2-CH3-3-Cl S CH2 CH2 968 i-C3H7 2-CH3-3-Cl S CH2 CH2 969 c-C3H5 2-CH3-3-Cl S CH2 CH2 970 n-C4H9 2-CH3-3-Cl S CH2 CH2 971 s-C4H9 2-CH3-3-Cl S CH2 CH2 972 i-C4H9 2-CH3-3-Cl S CH2 CH2 973 t-C4H9 2-CH3-3-Cl S CH2 CH2 974 n-C5H11 2-CH3-3-Cl S CH2 CH2 975 neo-C5H11 2-CH3-3-Cl S CH2 CH2 976 c-C5H9 2-CH3-3-Cl S CH2 CH2 164- 167 978 t-C5H11 2-CH3-3-Cl S CH2 CH2 979 C2H5 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 980 n-C3H7 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 152- 155 981 i-C3H7 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 982 c-C3H5 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 983 n-C4H9 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 984 s-C4H9 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 985 i-C4H9 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 986 t-C4H9 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 987 n-C5H11 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 988 neo-C5H11 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 989 c-C5H9 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 990 t-C5H11 2,6-(C2H5)2-3-Cl NCH3 CH2 CH2 991 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 O 992 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 O 214- 217 993 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 O 994 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 O 995 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 O 996 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 O 997 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 O 998 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 O 999 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 O 1000 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 O 1001 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 O 1002 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 O 1003 C2H5 2-CH3-3-Cl CH2 CH2 O 1004 n-C3H7 2-CH3-3-Cl CH2 CH2 O 1005 i-C3H7 2-CH3-3-Cl CH2 CH2 O 1006 c-C3H5 2-CH3-3-Cl CH2 CH2 O 1007 n-C4H9 2-CH3-3-Cl CH2 CH2 O 1008 s-C4H9 2-CH3-3-Cl CH2 CH2 O 1009 i-C4H9 2-CH3-3-Cl CH2 CH2 O 1010 t-C4H9 2-CH3-3-Cl CH2 CH2 O 1011 n-C5H11 2-CH3-3-Cl CH2 CH2 O 1012 neo-C5H11 2-CH3-3-Cl CH2 CH2 O 1013 c-C5H9 2-CH3-3-Cl CH2 CH2 O 1014 t-C5H11 2-CH3-3-Cl CH2 CH2 O 1015 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 S 1016 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 S 211- 213 1017 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 S 1018 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 S 1019 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 S 1020 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 S 1021 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 S 1022 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 S 1023 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 S 1024 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 S 1025 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 S 1026 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 S 1027 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1028 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 SO 230- 233 1029 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1030 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1031 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1032 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1033 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1034 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1035 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1036 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1037 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1038 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO 1039 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1040 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 198- 200 1041 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1042 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1043 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1044 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1045 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1046 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1047 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1048 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1049 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1050 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 SO2 1051 C2H5 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1052 n-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 157- 160 1053 i-C3H7 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1054 c-C3H5 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1055 n-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1056 s-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1057 i-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1058 t-C4H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1059 n-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1060 neo-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1061 c-C5H9 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3 1062 t-C5H11 2,6-(C2H5)2-3-Cl CH2 CH2 NCH3

[0274] 8 TABLE 8 32 No R3 X R14 Z mp ° C. 1063 C2H5 2,6-(C2H5)2-3-Cl CH3 O 1064 n-C3H7 2,6-(C2H5)2-3-Cl CH3 O 189-192 1065 i-C3H7 2,6-(C2H5)2-3-Cl CH3 O 1066 c-C3H5 2,6-(C2H5)2-3-Cl CH3 O 1067 n-C4H9 2,6-(C2H5)2-3-Cl CH3 O 1068 s-C4H9 2,6-(C2H5)2-3-Cl CH3 O 1069 i-C4H9 2,6-(C2H5)2-3-Cl CH3 O 1070 t-C4H9 2,6-(C2H5)2-3-Cl CH3 O 1071 n-C5H11 2,6-(C2H5)2-3-Cl CH3 O 1072 neo-C5H11 2,6-(C2H5)2-3-Cl CH3 O 1073 c-C5H9 2,6-(C2H5)2-3-Cl CH3 O 1074 t-C5H11 2,6-(C2H5)2-3-Cl CH3 O 1075 C2H5 2-CH3-3-Cl CH3 O 1076 n-C3H7 2-CH3-3-Cl CH3 O 1077 i-C3H7 2-CH3-3-Cl CH3 O 1078 c-C3H5 2-CH3-3-Cl CH3 O 1079 n-C4H9 2-CH3-3-Cl CH3 O 1080 s-C4H9 2-CH3-3-Cl CH3 O 1081 i-C4H9 2-CH3-3-Cl CH3 O 1082 t-C4H9 2-CH3-3-Cl CH3 O 1083 n-C5H11 2-CH3-3-Cl CH3 O 1084 neo-C5H11 2-CH3-3-Cl CH3 O 1085 c-C5H9 2-CH3-3-Cl CH3 O 192-195 1086 t-C5H11 2-CH3-3-Cl CH3 O 1087 C2H5 2,6-(C2H5)2-3-Cl H NCH3 239-241 1088 n-C3H7 2,6-(C2H5)2-3-Cl H NCH3 230-233 1089 i-C3H7 2,6-(C2H5)2-3-Cl H NCH3 1090 c-C3H5 2,6-(C2H5)2-3-Cl H NCH3 1091 n-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1092 s-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1093 i-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1094 t-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1095 n-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1096 neo-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1097 c-C5H9 2,6-(C2H5)2-3-Cl H NCH3 1098 t-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1099 C2H5 2-CH3-3-Cl H NCH3 1100 n-C3H7 2-CH3-3-Cl H NCH3 1101 i-C3H7 2-CH3-3-Cl H NCH3 1102 c-C3H5 2-CH3-3-Cl H NCH3 1103 n-C4H9 2-CH3-3-Cl H NCH3 1104 s-C4H9 2-CH3-3-Cl H NCH3 1105 i-C4H9 2-CH3-3-Cl H NCH3 1106 t-C4H9 2-CH3-3-Cl H NCH3 1107 n-C5H11 2-CH3-3-Cl H NCH3 1108 neo-C5H11 2-CH3-3-Cl H NCH3 1109 c-C5H9 2-CH3-3-Cl H NCH3 1110 t-C5H11 2-CH3-3-Cl H NCH3 1111 C2H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1112 n-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 211-215 1113 i-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 1114 c-C3H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1115 n-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1116 s-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1117 i-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1118 t-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1119 n-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1120 neo-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1121 c-C5H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1122 t-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3

[0275] 9 TABLE 9 33 No R3 X R14 Z mp ° C. 1123 C2H5 2,6-(C2H5)2-3-Cl H NCH3 1124 n-C3H7 2,6-(C2H5)2-3-Cl H NCH3 217-220 1125 i-C3H7 2,6-(C2H5)2-3-Cl H NCH3 1126 c-C3H5 2,6-(C2H5)2-3-Cl H NCH3 1127 n-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1128 s-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1129 i-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1130 t-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1131 n-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1132 neo-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1133 c-C5H9 2,6-(C2H5)2-3-Cl H NCH3 1134 t-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1135 C2H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1136 n-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 211-214 1137 i-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 1138 c-C3H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1139 n-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1140 s-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1141 i-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1142 t-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1143 n-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1144 neo-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1145 c-C5H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1146 t-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3

[0276] 10 TABLE 10 34 No R3 X R14 Z mp ° C. 1147 C2H5 2,6-(C2H5)2-3-Cl H NCH3 1148 n-C3H7 2,6-(C2H5)2-3-Cl H NCH3 225-228 1149 i-C3H7 2,6-(C2H5)2-3-Cl H NCH3 1150 c-C3H5 2,6-(C2H5)2-3-Cl H NCH3 1151 n-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1152 s-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1153 i-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1154 t-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1155 n-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1156 neo-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1157 c-C5H9 2,6-(C2H5)2-3-Cl H NCH3 1158 t-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1159 C2H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1160 n-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 220-224 1161 i-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 1162 c-C3H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1163 n-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1164 s-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1165 i-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1166 t-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1167 n-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1168 neo-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1169 c-C5H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1170 t-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3

[0277] 11 TABLE 11 35 No R3 X R14 Z mp ° C. 1171 CH3 2,6-(C2H5)2-3-Cl H NCH3 216-218 1172 C2H5 2,6-(C2H5)2-3-Cl H NCH3 1173 n-C3H7 2,6-(C2H5)2-3-Cl H NCH3 213-216 1174 i-C3H7 2,6-(C2H5)2-3-Cl H NCH3 1175 c-C3H5 2,6-(C2H5)2-3-Cl H NCH3 1176 n-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1177 s-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1178 i-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1179 t-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1180 n-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1181 neo-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1182 c-C5H9 2,6-(C2H5)2-3-Cl H NCH3 1183 t-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1184 C2H5 2-CH3-3-Cl H NCH3 1185 n-C3H7 2-CH3-3-Cl H NCH3 1186 i-C3H7 2-CH3-3-Cl H NCH3 1187 c-C3H5 2-CH3-3-Cl H NCH3 1188 n-C4H9 2-CH3-3-Cl H NCH3 1189 s-C4H9 2-CH3-3-Cl H NCH3 1190 i-C4H9 2-CH3-3-Cl H NCH3 1191 t-C4H9 2-CH3-3-Cl H NCH3 1192 n-C5H11 2-CH3-3-Cl H NCH3 1193 neo-C5H11 2-CH3-3-Cl H NCH3 1194 c-C5H9 2-CH3-3-Cl H NCH3 1195 t-C5H11 2-CH3-3-Cl H NCH3 1196 C2H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1197 n-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 209-212 1198 i-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 1199 c-C3H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1200 n-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1201 s-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1202 i-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1203 t-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1204 n-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1205 neo-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1206 c-C5H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1207 t-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3

[0278] 12 TABLE 12 36 No R3 X R14 Z mp ° C. 1208 C2H5 2,6-(C2H5)2-3-Cl H NCH3 1209 n-C3H7 2,6-(C2H5)2-3-Cl H NCH3 222-225 1210 i-C3H7 2,6-(C2H5)2-3-Cl H NCH3 1211 c-C3H5 2,6-(C2H5)2-3-Cl H NCH3 1212 n-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1213 s-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1214 i-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1215 t-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1216 n-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1217 neo-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1218 n-C5H9 2,6-(C2H5)2-3-Cl H NCH3 1219 t-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1220 C2H5 2-CH3-3-Cl H NCH3 1221 n-C3H7 2-CH3-3-Cl H NCH3 1222 i-C3H7 2-CH3-3-Cl H NCH3 1223 c-C3H5 2-CH3-3-Cl H NCH3 1224 n-C4H9 2-CH3-3-Cl H NCH3 1225 s-C4H9 2-CH3-3-Cl H NCH3 1226 i-C4H9 2-CH3-3-Cl H NCH3 1227 t-C4H9 2-CH3-3-Cl H NCH3 1228 n-C5H11 2-CH3-3-Cl H NCH3 1229 neo-C5H11 2-CH3-3-Cl H NCH3 1230 c-C5H9 2-CH3-3-Cl H NCH3 1231 t-C5H11 2-CH3-3-Cl H NCH3 1232 C2H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1233 n-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 215-218 1234 i-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 1235 c-C3H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1236 n-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1237 s-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1238 i-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1239 t-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1240 n-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1241 neo-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1242 c-C5H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1243 t-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3

[0279] 13 TABLE 13 37 No R3 X R14 Z mp ° C. 1244 C2H5 2,6-(C2H5)2-3-Cl H O 1245 n-C3H7 2,6-(C2H5)2-3-Cl H O 189-195 1246 i-C3H7 2,6-(C2H5)2-3-Cl H O 1247 c-C3H5 2,6-(C2H5)2-3-Cl H O 1248 n-C4H9 2,6-(C2H5)2-3-Cl H O 1249 s-C4H9 2,6-(C2H5)2-3-Cl H O 1250 i-C4H9 2,6-(C2H5)2-3-Cl H O 1251 t-C4H9 2,6-(C2H5)2-3-Cl H O 1252 n-C5H11 2,6-(C2H5)2-3-Cl H O 1253 neo-C5H11 2,6-(C2H5)2-3-Cl H O 1254 c-C5H9 2,6-(C2H5)2-3-Cl H O 1255 t-C5H11 2,6-(C2H5)2-3-Cl H O 1256 C2H5 2,6-(C2H5)2-3-Cl CH3 O 1257 n-C3H7 2,6-(C2H5)2-3-Cl CH3 O 1258 i-C3H7 2,6-(C2H5)2-3-Cl CH3 O 1259 c-C3H5 2,6-(C2H5)2-3-Cl CH3 O 1260 n-C4H9 2,6-(C2H5)2-3-Cl CH3 O 1261 s-C4H9 2,6-(C2H5)2-3-Cl CH3 O 1262 i-C4H9 2,6-(C2H5)2-3-Cl CH3 O 1263 t-C4H9 2,6-(C2H5)2-3-Cl CH3 O 1264 n-C5H11 2,6-(C2H5)2-3-Cl CH3 O 1265 neo-C5H11 2,6-(C2H5)2-3-Cl CH3 O 1266 c-C5H9 2,6-(C2H5)2-3-Cl CH3 O 1267 t-C5H11 2,6-(C2H5)2-3-Cl CH3 O 1268 C2H5 2,6-(C2H5)2-3-Cl H NCH3 1269 n-C3H7 2,6-(C2H5)2-3-Cl H NCH3 198-202 1270 i-C3H7 2,6-(C2H5)2-3-Cl H NCH3 1271 c-C3H5 2,6-(C2H5)2-3-Cl H NCH3 1272 n-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1273 s-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1274 i-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1275 t-C4H9 2,6-(C2H5)2-3-Cl H NCH3 1276 n-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1277 neo-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1278 c-C5H9 2,6-(C2H5)2-3-Cl H NCH3 1279 t-C5H11 2,6-(C2H5)2-3-Cl H NCH3 1280 C2H5 2-CH3-3-Cl H NCH3 1281 n-C3H7 2-CH3-3-Cl H NCH3 1282 i-C3H7 2-CH3-3-Cl H NCH3 1283 c-C3H5 2-CH3-3-Cl H NCH3 1284 n-C4H9 2-CH3-3-Cl H NCH3 1285 s-C4H9 2-CH3-3-Cl H NCH3 1286 i-C4H9 2-CH3-3-Cl H NCH3 1287 t-C4H9 2-CH3-3-Cl H NCH3 1288 n-C5H11 2-CH3-3-Cl H NCH3 1289 neo-C5H11 2-CH3-3-Cl H NCH3 1290 c-C5H9 2-CH3-3-Cl H NCH3 1291 s-C5H11 2-CH3-3-Cl H NCH3 1292 t-C5H11 2-CH3-3-Cl H NCH3 1293 C2H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1294 n-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 201-205 1295 i-C3H7 2,6-(C2H5)2-3-Cl CH3 NCH3 1296 c-C3H5 2,6-(C2H5)2-3-Cl CH3 NCH3 1297 n-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1298 s-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1299 i-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1300 t-C4H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1301 n-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1302 neo-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3 1303 c-C5H9 2,6-(C2H5)2-3-Cl CH3 NCH3 1304 t-C5H11 2,6-(C2H5)2-3-Cl CH3 NCH3

[0280] 14 TABLE 14 38 No R3 X (R9)n mp ° C. 1305 C2H5 2,6-(C2H5)2-3-Cl H 218-220 1306 n-C3H7 2,6-(C2H5)2-3-Cl H 184-186 1307 i-C3H7 2,6-(C2H5)2-3-Cl H 1308 c-C3H5 2,6-(C2H5)2-3-Cl H 1309 n-C4H9 2,6-(C2H5)2-3-Cl H 1310 s-C4H9 2,6-(C2H5)2-3-Cl H 1311 i-C4H9 2,6-(C2H5)2-3-Cl H 148-150 1312 t-C4H9 2,6-(C2H5)2-3-Cl H 1313 n-C5H11 2,6-(C2H5)2-3-Cl H 1314 neo-C5H11 2,6-(C2H5)2-3-Cl H 208-210 1315 c-C5H9 2,6-(C2H5)2-3-Cl H 174-176 1316 t-C5H11 2,6-(C2H5)2-3-Cl H 1317 C2H5 2-CH3-3-Cl H 1318 n-C3H7 2-CH3-3-Cl H 204-206 1319 i-C3H7 2-CH3-3-Cl H 1320 c-C3H5 2-CH3-3-Cl H 1321 n-C4H9 2-CH3-3-Cl H 1322 s-C4H9 2-CH3-3-Cl H 1323 i-C4H9 2-CH3-3-Cl H 1324 t-C4H9 2-CH3-3-Cl H 1325 n-C5H11 2-CH3-3-Cl H 1326 neo-C5H11 2-CH3-3-Cl H 1327 c-C5H9 2-CH3-3-Cl H 218-220 1328 t-C5H11 2-CH3-3-Cl H 1329 C2H5 2,6-(C2H5)2-3-Cl 6-CH3 1330 n-C3H7 2,6-(C2H5)2-3-Cl 6-CH3 1331 i-C3H7 2,6-(C2H5)2-3-Cl 6-CH3 1332 c-C3H5 2,6-(C2H5)2-3-Cl 6-CH3 1333 n-C4H9 2,6-(C2H5)2-3-Cl 6-CH3 1334 s-C4H9 2,6-(C2H5)2-3-Cl 6-CH3 1335 i-C4H9 2,6-(C2H5)2-3-Cl 6-CH3 1336 t-C4H9 2,6-(C2H5)2-3-Cl 6-CH3 1337 n-C5H11 2,6-(C2H5)2-3-Cl 6-CH3 1338 neo-C5H11 2,6-(C2H5)2-3-Cl 6-CH3 1339 c-C5H9 2,6-(C2H5)2-3-Cl 6-CH3 1340 t-C5H11 2,6-(C2H5)2-3-Cl 6-CH3 1341 C2H5 2,6-(C2H5)2-3-Cl 6-Cl 1342 n-C3H7 2,6-(C2H5)2-3-Cl 6-Cl 1343 i-C3H7 2,6-(C2H5)2-3-Cl 6-Cl 1344 c-C3H5 2,6-(C2H5)2-3-Cl 6-Cl 1345 n-C4H9 2,6-(C2H5)2-3-Cl 6-Cl 1346 s-C4H9 2,6-(C2H5)2-3-Cl 6-Cl 1347 i-C4H9 2,6-(C2H5)2-3-Cl 6-Cl 1348 t-C4H9 2,6-(C2H5)2-3-Cl 6-Cl 1349 n-C5H11 2,6-(C2H5)2-3-Cl 6-Cl 1350 neo-C5H11 2,6-(C2H5)2-3-Cl 6-Cl 1351 c-C5H9 2,6-(C2H5)2-3-Cl 6-Cl 1352 t-C5H11 2,6-(C2H5)2-3-Cl 6-Cl

[0281] Herbicides comprising, as an active ingredient thereof, the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) or a salt thereof are useful for controlling annual and perennial weeds which grow in paddy fields, upland fields, orchards, swamps, etc., such as barnyard grass (Echinochloa crus-galli Beauv., an annual gramineous weed which is an injurious weed of paddy fields), umbrella plant (Cyperus difformis L., an annual cyperaceous grass which is an injurious weed of paddy fields), slender spikerush (Eleocharis acicularis Roem. et Schult, a perennial cyperaceous grass which is an injurious weed of paddy fields and which grows also in swamps and waterways), arrowhead (Saguittaria pygmaea Miq., an injurious perennial weed of Alismataceae family which grows in paddy fields, swamps and ditches), bulrush (Scirpus juncoides Roxb. var. horarui ohwi, a perennial cyperaceous weed which grows in paddy fields, swamps and ditches), foxtail grass (Alopecurus aegualis var. amurensis Ohwi, gramineous grass which grows in paddy fields and low swamps), wild oats (Avena fatua L., a biennial gramineous grass which grows in plains, waste lands and upland fields), mugwort (Artemisia princeps Pamp., a perennial composite grass which grows in cultivated and uncultivated fields and mountains), large crabgrass (Digitaria adscenducus Henr., an annual gramineous grass which is a strongly injurious weed of upland fields and orchards), Gishigishi or Japanese dock (Rumex japonicus Houtt., a perennial polygonaceous weed which grows in upland fields and roadsides), umbrella sedge (Cyperus iria L., an annual cyperaceous weed), redroot pigweed (Amaranthus varidis L., an annual weed of Amaranthaceae family which grows in vacant lands, roadsides and upland fields), cocklebur (Xanthium strumarium L., an injurious annual composite weed which grows in upland fields), velvetleaf (Abutilon theophrasti L., an injurious annual weed of Malvaceae family which grows in upland fields), purple thornapple (Dutura tatula L., an annual injurious weed of Convolvulaceae family which grows in upland fields), bird's eye speedwell (Veronica persica Poir., an injurious biennual weed of Scrophulariaceae family which grows in upland fields) and cleavers (Galium aparine L., an injurious annual weed of Rubiaceae family which grows in upland fields and orchards), and especially useful for controlling weeds such as barnyard grass and bulrush in paddy fields.

[0282] Since the herbicides comprising, as an active ingredient thereof, the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) or a salt thereof exhibit an excellent controlling effect on weeds before or after emergence, the characteristic physiological activities of the herbicides can be effectively manifested by treating fields with the herbicides before planting useful plants therein, or after planting useful plants therein (including the case in which useful plants are already planted as in orchards) but during the period from the initial stage of emergence of weeds to their growth stage.

[0283] However, the application of the herbicides of the present invention is not restricted only to the modes mentioned above. The herbicides of the present invention can be applied to control not only weeds which grow in paddy fields but also weeds which grow in other places such as fields after reaping, temporarily non-cultivated paddy fields and upland fields, ridges between fields, agricultural pathways, waterways, lands constructed for pasture, graveyards, parks, roads, playgrounds, unoccupied areas around buildings, developed lands, railways, forests and the like.

[0284] The treatment of target weeds with the herbicides is most effective in economy when the treatment is carried out not later than the initial stage of emergence of weeds. However, the time of application is not limited thereto, but it is also possible to control the weeds in the growth stage.

[0285] When the fused heterocyclic dicarboxylic acid diamide derivative of general formula (I) or a salt thereof is used a herbicide, the compound is usually formed into a preparation of convenient form according to the conventional method in the production of agricultural compositions.

[0286] The fused heterocyclic dicarboxylic acid diamide derivatives of general formula (I) or salt thereof according to the present invention are compounded together with adjuvants according to the need, then supported on an appropriate carrier by the procedure of dissolution, separation, suspension, mixing, impregnation, adsorption or adhesion, and then formed into appropriate preparation form such as suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust, tablet or the like, after which they are put to use.

[0287] The inert carrier used in the present invention may be any of a solid carrier and a liquid carrier. The materials which can constitute the solid carrier include, for example, soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residues of vegetables, powdered synthetic polymers or resins, clay (e.g. kaolin, bentonite and acid clay), talc (e.g. talc and pyrophyllite), silica materials (e.g. diatomaceous earth, siliceous sand, mica, white carbon, i.e. synthetic high-dispersion silicic acid, also called finely divided hydrated silica or hydrated silicic acid, some of the commercially available products contain calcium silicate as the major component), activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic or mineral powders, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride and the like, and compost. These carriers may be used either alone or as a mixture of two or more carriers.

[0288] The liquid carrier is that which itself has a solubility or which is without such solubility but is capable of dispersing an active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier, which can be used alone or as a mixture thereof. Water; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers such as ethyl ether, dioxane, cellosolve, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as kerosene and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene; halogenated hydrocarbons such as dichlorethane, chloroform and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate; amides such as dimethylformamide, diethylformamide and dimethylacetamide; nitriles such as acetonitrile; and dimethyl sulfoxide.

[0289] The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination of two or more adjuvants in some cases, or need not to be used at all.

[0290] To emulsify, disperse, dissolve and/or wet an active ingredient, a surfactant is used. As the surfactant, there can be exemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalene-sulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.

[0291] Further, to stabilize the dispersion of an active ingredient, tackify it and/or bind it, there may be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohols, turpentine, bran oil, bentonite and ligninsulfonates.

[0292] To improve the flowability of a solid product, there may be used adjuvants such as waxes, stearates and alkyl phosphates.

[0293] Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products.

[0294] Adjuvants such as silicone oil may also be used as a defoaming agent.

[0295] The content of the active ingredient may be varied according to the need. In dusts or granules, the suitable content thereof is from 0.01 to 50% by weight. In emulsifiable concentrate and flowable wettable powder, too, the suitable content is from 0.01 to 50% by weight.

[0296] The herbicide of the present invention comprising the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) or a salt thereof as an active ingredient is used to kill a variety of weeds or to suppress their growth in the following manner. That is, it is applied to weeds or foliage or soil in a place in which generation or growth of objective weed is undesirable either directly or after being properly diluted with or suspended in water or the like, in an amount effective for control of the weeds.

[0297] The applying dosage of the herbicide of the present invention comprising the fused heterocyclic dicarboxylic acid diamide derivative of general formula (I) or a salt thereof is varied depending upon various factors such as a purpose, weed to be controlled, a growth state of a plant, tendency of generation of weed, weather, environmental conditions, a preparation form, an application method, an application site and an application time. It may be properly chosen in a range of 0.1 g to 10 kg (in terms of active ingredient compound) per hectare depending upon purpose.

[0298] The herbicide of the present invention comprising the fused heterocyclic dicarboxylic acid diamide of general formula (I) or a salt thereof as active ingredient may be used in admixture with other herbicides in order to expand both spectrum of controllable weeds and the period of time when effective applications are possible or to reduce the dosage.

EXAMPLES

[0299] Next, typical examples of the present invention and referential examples are presented below. The present invention is by no means limited by these examples.

Example 1

[0300] 1-1. Production of 3-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-7-fluoro-2-quinolinecarboxylic acid n-propylamide (Compound No. 158)

[0301] In 10 ml of tetrahydrofuran was dissolved 800 mg (2.41 mmol) of N-(3-chloro-2,6-diethylphenyl)-7-fluoro-2,3-quinolinedicarboximide. After adding 150 mg (2.5 mmol) of n-propylamine to the solution obtained above, a reaction was carried out for 12 hours.

[0302] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 820 mg of the objective compound was obtained as a white crystalline product.

[0303] Property: m.p. 220-222° C.; Yield: 87%

[0304] 1-2. Production of 3-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-1,8-naphthylidine-2-carboxylic acid ethylamide (Compound No. 360)

[0305] In 10 ml of dioxane was dissolved 700 mg (1.91 mmol) of 2,3-carboximide. After adding 95 mg (2.3 mmol) of ethylamine to the solution obtained above, a reaction was carried out for 12 hours.

[0306] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 620 mg of the objective compound was obtained as a white crystalline product.

[0307] Property: m.p. 249-264° C.; Yield: 80%

[0308] 1-3. Production of 3-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-7,8-dihydro-5H-pyrano[4,3-b]pyridine-2-carboxylic acid n-propylamide (Compound No. 462)

[0309] In 10 ml of dioxane was dissolved 770 mg (2.08 mmol) of N-(3-chloro-2,6-diethylphenyl)-7,8-dihydro-5H-pyrano[4,3-b]pyridine-2,3-carboximide. After adding 127 mg (2.3 mmol) of n-propylamine to the solution obtained above, a reaction was carried out for 12 hours.

[0310] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 735 mg of the objective compound was obtained as a white crystalline product.

[0311] Property: m.p. 166-170° C.; Yield: 83%

Example 2

[0312] 2-1. Production of 6-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-2,3-dihydro-1-oxo-thieno[2,3-b]pyridine-5-carboxylic acid n-propylamide (Compound No. 1028)

[0313] In 10 ml of chloroform was dissolved 500 mg (1.16 mmol) of 6-(3-chloro-2,6-diethylphenyl)aminocarbonyl-2,3-dihydrothieno[2,3-b]pyridine-5-carboxylic acid n-propylamide. After adding 200 mg (1.1 mmol) of m-chloroperbenzoic acid to the solution obtained above at 0° C., a reaction was carried out at ambient temperature for 6 hours.

[0314] After completion of the reaction, the reaction mixture was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent, whereby 400 mg of the objective compound was obtained as a white crystalline product.

[0315] Property: m.p. 230-233° C.; Yield: 77%

[0316] 2-2. Production of 6-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-2,3-dihydro-1,1-dioxo-thieno[2,3-b]pyridine-5-carboxylic acid n-propylamide (Compound No. 1040)

[0317] In 10 ml of chloroform was dissolved 500 mg (1.16 mmol) of 6-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-2,3-dihydrothieno[2,3-b]pyridine-5-carboxylic acid n-propylamide. After adding 400 mg (2.2 mmol) of m-chloroperbenzoic acid to the solution obtained above at 0° C., a reaction was carried out at ambient temperature for 6 hours.

[0318] After completion of the reaction, the reaction mixture was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent, whereby 450 mg of the objective compound was obtained as a white crystalline product.

[0319] Property: m.p. 198-200° C.; Yield: 84%

Referential Example 1

Production of 6-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[5,4-b]pyridine-5-carboxylic Acid

[0320] In 100 ml of tetrahydrofuran was dissolved 8.0 g (39.4 mmol) of 1-methyl-pyrazolo[5,4-b]pyridine-5,6-dicarboxylic acid anhydride. After adding 7.23 g (39.4 mmol) of 3-chloro-2,6-diethylaniline to the solution obtained above, a reaction was carried out at ambient temperature for 12 hours.

[0321] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the deposited crystal was washed with a small quantity of ether. Thus, 12.0 g (yield 79%) of the objective compound was obtained.

[0322] —H-NMR[TMS/CDCl3, &dgr; (ppm)]

[0323] 1.21(3H,t,J=7.5 Hz), 1.26(3H,t,J=7.5 Hz),

[0324] 2.63(2H,q,J=7.5 Hz), 2.83(2H,q,J=7.5 Hz),

[0325] 4.27(3H,s), 7.18(1H,d,J=8.4 Hz),

[0326] 7.41(1H,d,J=8.4 Hz), 8.30(1H,s), 9.43(1H,s),

[0327] 10.10 (1H,bs)

Referential Example 2

Production of N-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[5,4-b]pyridine-5,6-carboximide

[0328] In 30 ml of trifluoroacetic acid was dissolved 9.0 g (23.3 mmol) of 6-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[5,4-b]pyridine-5-carboxylic acid. After adding 4.90 g (23.3 mmol) of trifluoroacetic acid anhydride to the solution obtained above, a reaction was carried out under reflux for 4 hours.

[0329] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 8.0 g (yield 93%) of the objective compound was obtained.

[0330] 1H-NMR(TMS/CDCl3, &dgr; (ppm)]

[0331] 1.09(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0332] 2.43(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz),

[0333] 4.34(3H,s), 7.20(1H,d,J=8.4 Hz),

[0334] 7.47(1H,d,J=8.4 Hz), 8.35(1H,s), 8.67(1H,s)

Referential Example 3

Production of N-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[4,5-b]pyridine-5,6-carboximide

[0335] In 30 ml of trifluoroacetic acid was dissolved 7.5 g (19.4 mmol) of 5-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[4,5-b]pyridine-6-carboxylic acid. After adding 4.08 g (19.4 mmol) of trifluoroacetic acid anhydride to the solution obtained above, a reaction was carried out under reflux for 4 hours.

[0336] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 6.5 g (yield 91%) of the objective compound was obtained.

[0337] 1H-NMR[TMS/CDCl3&dgr; (ppm)]

[0338] 1.08(3H,t,J=7.5 Hz), 1.12(3H,t,J=7.5 Hz),

[0339] 2.43(2H,q,J=7.5 Hz), 2.63(2H,q,J=7.5 Hz),

[0340] 4.27(3H,s), 7.20(1H,d,J=8.4 Hz),

[0341] 7.48(1H,d,J=8.4 Hz), 8.37(1H,s), 8.53(1H,s)

[0342] Next, typical preparation examples and test examples of the present invention are shown below. The present invention is by no means limited to these examples.

[0343] In the preparation examples, the term “part” means part by weight.

Preparation Example 1

[0344] 15 Each compound listed in Tables 1 to 14 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl 10 parts ether and calcium alkylbenzenesulfonate

[0345] An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.

Preparation Example 2

[0346] 16 Each compound listed in Tables 1 to 14  3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts

[0347] A dust was prepared by mixing uniformly and grinding the above ingredients.

Preparation Example 3

[0348] 17 Each compound listed in Tables 1 to 14  5 parts Mixed powder of bentonite and clay 90 parts Calcium ligninsulfonate  5 parts

[0349] Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying.

Preparation Example 4

[0350] 18 Each compound listed in Tables 1 to 14 20 parts Mixture of kaolin and synthetic high-dispersion silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate  5 parts

[0351] A wettable powder was prepared by mixing uniformly and grinding the above ingredients.

Test Example 1

Test for Herbicidal Effect on Paddy Field Weeds Before Emergence

[0352] Soil was filled into {fraction (1/10000)} are pots and brought into a state of paddy field, in which seeds of barnyard grass (Echinochloa crus-galli Beauv.) and bulrush (Scirpus juncoides Roxb.) were made to be before germination. The soil in the pots were treated with a solution containing a predetermined dosage of a chemical agent comprising a compound of the present invention listed in Tables 1 to 14.

[0353] Twenty one days after the treatment, the herbicidal effect was investigated, the result was compared with that in untreated plot to calculate the weed-controlling rate, and the herbicidal effect was judged according to the following criterion:

[0354] 5—Weed-killing rate is 100%.

[0355] 4—Weed-killing rate is 90-99%.

[0356] 3—Weed-killing rate is 70-89%.

[0357] 2—Weed-killing rate is 40-69%.

[0358] 1—Weed-killing rate is 1-39%.

[0359] 0—Weed-killing rate is 0%.

[0360] The results are shown in Table 15.

Test Example 2

Test for Herbicidal Effect on Paddy Field Weeds after Emergence

[0361] Soil was filled into {fraction (1/10000)} are pots and brought into a state of paddy field, in which seeds of barnyard grass (Echinochloa crus-galli Beauv.), bulrush (Scirpus juncoides Roxb.) and monochoria (Monochoria vaginalis Presl) were made to reach one-leaved stage. The soil in the pots were treated with a solution containing a predetermined dosage of a chemical agent comprising a compound of the present invention listed in Tables 1 to 14.

[0362] Twenty one days after the treatment, the herbicidal effect was investigated and the result was compared with that in untreated plot to calculate the weed-controlling rate, and the herbicidal effect was judged according to the same criterion as in Test Example 1.

[0363] The results are shown in Table 15. 19 TABLE 15 Pre-emergence treatment Post-emergence treatment Dosage Barnyard Barnyard Mono- No. (kg/ha) grass Bulrush grass Bulrush choria  1 5 5 5 4 4 5  2 5 5 5 4 4 5  3 5 5 5 4 4 5  28 5 3 3 3 3 4  29 5 4 3 3 3 4  30 5 5 4 3 3 5  43 5 4 2 3 2 4  44 5 4 3 3 2 4  53 5 5 2 3 2 4  58 5 4 3 3 3 4  71 5 5 5 3 3 5  97 5 3 1 2 1 3  99 5 5 5 5 5 5 100 5 5 5 5 5 5 101 5 5 5 5 5 5 126 5 3 2 2 1 3 127 5 4 3 4 4 5 128 5 5 5 5 5 5 129 5 5 5 5 5 5 130 5 5 5 5 5 5 157 5 5 5 5 5 5 158 5 5 5 5 5 5 189 5 5 4 4 3 5 200 5 4 2 3 1 3 201 5 3 2 3 1 3 219 5 5 5 4 4 5 224 5 5 3 3 2 3 228 5 5 4 3 2 4 234 5 5 2 3 2 4 243 5 3 1 3 1 3 246 5 4 1 2 1 3 275 5 5 5 5 4 5 276 5 5 5 3 4 5 289 5 5 5 5 4 5 290 5 5 5 5 5 5 291 5 5 4 5 4 5 305 5 5 4 4 3 5 310 5 4 3 3 2 5 334 5 5 4 4 4 5 339 5 4 3 3 2 4 343 5 5 3 3 3 5   359-1 5 5 5 5 5 5   359-2 5 5 5 5 5 5   359-3 5 5 5 5 5 5   359-4 5 5 5 5 5 5   359-5 5 5 5 5 5 5   359-6 5 5 5 5 5 5 360 5 5 5 5 5 5 361 5 5 5 5 5 5 375 5 5 5 5 5 5 388 5 5 5 5 5 5 414 5 5 5 5 5 5 423 5 5 5 5 5 5 431 5 5 5 5 5 5 438 5 5 5 5 5 5 447 5 5 5 5 5 5 450 5 5 5 5 5 5 462 5 5 5 5 5 5 474 5 5 5 5 5 5 486 5 5 5 5 5 5 498 5 5 5 5 5 5 510 5 5 5 5 5 5 519 5 5 5 5 5 5 527 5 5 5 5 5 5 534 5 5 5 5 5 5 558 5 5 5 5 5 5 570 5 5 5 5 5 5 582 5 5 5 5 5 5 606 5 5 5 5 5 5 630 5 5 5 5 5 5 654 5 5 3 3 1 4 678 5 5 5 5 5 5 679 5 5 5 5 5 5 703 5 5 5 5 5 5 724 5 5 5 5 5 5 727 5 5 5 5 5 5 739 5 5 5 5 5 5 760 5 5 5 5 5 5 763 5 4 3 4 3 5 774 5 5 5 5 5 5 775 5 5 5 5 5 5 796 5 5 5 5 5 5 798 5 5 5 5 5 5 799 5 5 5 5 5 5 811 5 5 5 5 5 5 814 5 5 5 5 5 5 824 5 5 5 5 5 5 836 5 5 5 5 5 5 847 5 5 5 5 5 5 870 5 5 5 5 5 5 871 5 5 5 5 5 5 892 5 5 5 5 5 5 894 5 5 5 5 5 5 895 5 5 5 5 5 5 907 5 5 5 5 5 5 919 5 5 5 5 5 5 934 5 5 5 5 5 5 943 5 5 5 5 5 5 955 5 5 5 5 5 5 976 5 5 5 5 5 5 980 5 5 5 5 5 5 992 5 5 5 5 5 5 1016  5 5 5 5 5 5 1028  5 5 5 5 5 5 1040  5 5 5 5 5 5 1052  5 5 5 5 5 5 1064  5 5 5 5 5 5 1085  5 5 5 5 5 5 1087  5 5 5 5 5 5 1088  5 5 5 5 5 5 1112  5 5 5 5 5 5 1124  5 5 5 5 5 5 1136  5 5 5 5 5 5 1148  5 5 5 5 5 5 1160  5 5 5 5 5 5 1171  5 5 5 5 5 5 1173  5 5 5 5 5 5 1197  5 5 5 5 5 5 1209  5 5 5 5 5 5 1233  5 5 5 5 5 5 1245  5 5 5 5 5 5 1269  5 5 5 5 5 5 1294  5 5 5 5 5 5 1305  5 5 5 5 5 5 1306  5 5 5 5 5 5 1311  5 5 5 5 5 5 1314  5 5 5 4 4 5 1315  5 5 5 5 5 5 1318  5 5 4 4 4 5 1327  5 5 4 4 4 5

Test Example 3

Herbicidal Effect on Upland Weeds Before Emergence

[0364] Polyethylene-made vats having a size of 10 cm (length)×20 cm (width)×5 cm (height) were filled with soil, sown with seeds of forxtail grass (Alopecurus aegualis var. amurensis Ohwi); abbreviated to Am), barnyard grass (Echinochloa crus-galli Beauv., abbreviated to Ec), velvetleaf (Abutilon theophtasti L., abbreviated to At), cocklebur (Xanthium strumarium L., abbreviated to Xs), cleavers (Galium aparine L., abbreviated to Ga) and bird's eye speedwell (Veronica persica Poir., abbreviated to Vp) and with seeds of wheat (abbreviated to Wh) and soybean plant (So) as upland crop plants, and then covered with soil. Then, a liquid preparation of an agent comprising a prescribed concentration of a compound of the present invention (the compounds listed in Tables 1-14) as active ingredient was sprayed.

[0365] Fourteen days after the treatment, the herbicidal effect was investigated, from which weed-killing rate was calculated in the same manner as in Test Example 1, and the herbicidal effect was judged.

[0366] At the same time, phytotoxicity to soybean plant and wheat was investigated and judged according to the criterion mentioned below.

[0367] Criterion for judgment of phytotoxicity:

[0368] 5—Crop-killing rate is 100%.

[0369] 4—Crop-killing rate is 90-99%.

[0370] 3—Crop-killing rate is 70-89%.

[0371] 2—Crop-killing rate is 40-69%.

[0372] 1—Crop-killing rate is 1-39%.

[0373] 0—Crop-killing rate is 0-20%

[0374] (No Phytotoxicity).

[0375] The results are summarized in Table 16. 20 TABLE 16 Dosage Phytotoxicity Herbicidal effect No (kg/ha) Wh So Am Ec At Xs Ga Vp  1 5 3 1 4 5 5 5 4 5  2 5 3 1 5 5 5 5 5 5  3 5 2 1 5 5 5 5 5 5  28 5 1 0 4 3 4 3 3 4  29 5 4 1 4 4 5 4 4 5  30 5 3 1 5 5 5 4 4 5  43 5 1 0 4 3 4 3 3 4  44 5 1 0 4 3 4 2 4 4  53 5 1 0 4 4 4 2 3 4  58 5 2 1 4 4 5 4 4 5  71 5 4 0 4 4 5 3 4 5  97 5 1 0 3 2 3 1 1 3  99 5 1 2 4 5 5 5 5 5 100 5 1 3 4 5 5 5 4 5 101 5 2 2 4 5 5 4 4 5 126 5 1 0 3 3 3 2 2 3 127 5 1 1 3 4 3 2 2 4 128 5 2 1 4 4 4 3 4 5 129 5 3 1 5 5 5 5 5 5 130 5 0 0 4 5 5 4 5 5 157 5 3 1 4 5 5 4 4 5 158 5 4 1 4 5 5 4 5 5 189 5 2 0 3 4 4 3 3 4 200 5 0 0 3 3 3 2 2 3 201 5 0 0 3 2 3 2 2 3 219 5 2 1 4 5 5 3 4 5 224 5 1 0 3 4 4 3 3 4 228 5 0 0 3 3 4 2 2 4 234 5 0 0 3 3 3 2 2 3 243 5 0 0 2 3 3 2 2 3 246 5 1 0 3 4 4 3 3 4 275 5 1 0 3 4 4 3 3 4 276 5 2 0 4 5 5 4 4 5 289 5 2 1 4 5 5 3 4 5 290 5 2 1 5 5 5 4 5 5 291 5 1 0 4 5 5 4 5 5 305 5 2 0 4 5 4 3 3 4 310 5 2 0 4 4 4 3 3 4 334 5 2 0 4 4 5 3 3 4 339 5 1 0 4 4 4 2 3 4 343 5 0 0 3 4 3 2 3 4   359-1 5 0 0 5 5 5 5 5 5   359-2 5 0 1 5 5 5 5 5 5   359-3 5 0 0 5 5 5 5 5 5   359-4 5 0 2 5 5 5 5 5 5   359-5 5 0 0 5 5 5 5 5 5   359-6 5 0 0 5 5 5 5 5 5 360 5 4 3 5 5 5 5 5 5 361 5 4 4 5 5 5 5 5 5 375 5 3 3 5 5 5 5 5 5 388 5 5 4 5 5 5 5 5 5 414 5 5 4 5 5 5 5 5 5 423 5 5 4 5 5 5 5 5 5 431 5 3 3 4 5 5 4 4 5 438 5 5 5 5 5 5 5 5 5 447 5 5 4 5 5 5 5 5 5 450 5 4 4 5 5 5 4 4 5 462 5 5 5 5 5 5 5 5 5 474 5 4 3 5 5 5 4 4 5 486 5 4 4 5 5 5 5 5 5 498 5 4 4 5 5 5 4 4 5 510 5 5 4 5 5 5 5 5 5 519 5 5 4 5 5 5 5 5 5 527 5 5 5 5 5 5 4 5 5 534 5 4 3 5 5 5 5 5 5 558 5 5 5 5 5 5 5 5 5 570 5 4 4 5 5 5 5 5 5 582 5 4 4 5 5 5 5 5 5 606 5 4 3 5 5 5 4 4 5 630 5 4 3 5 5 5 4 4 5 654 5 3 1 4 4 5 3 3 4 678 5 4 2 4 5 5 3 3 5 679 5 4 2 4 5 5 4 4 5 703 5 4 2 4 5 5 4 4 5 724 5 4 3 4 4 4 3 4 5 727 5 4 4 5 5 5 4 4 5 739 5 5 4 5 5 5 5 5 5 760 5 4 3 5 5 5 4 5 5 763 5 4 3 4 5 5 4 4 5 774 5 5 4 5 5 5 5 5 5 775 5 5 5 5 5 5 5 5 5 796 5 5 4 5 5 5 4 5 5 798 5 5 4 5 5 5 5 5 5 799 5 5 5 5 5 5 5 5 5 811 5 5 4 5 5 5 5 5 5 814 5 4 3 5 5 5 4 4 5 824 5 5 5 5 5 5 5 5 5 836 5 5 4 5 5 5 5 5 5 847 5 5 4 5 5 5 5 5 5 870 5 4 3 5 5 5 5 5 5 871 5 5 4 5 5 5 5 5 5 892 5 4 3 5 5 5 4 5 5 894 5 5 4 5 5 5 5 5 5 895 5 5 4 5 5 5 5 5 5 907 5 5 4 5 5 5 5 5 5 919 5 5 5 5 5 5 5 5 5 934 5 5 4 5 5 5 4 5 5 943 5 4 3 5 5 5 5 5 5 955 5 5 3 5 5 5 5 5 5 976 5 5 4 5 5 5 5 5 5 980 5 5 4 5 5 5 5 5 5 992 5 5 5 5 5 5 5 5 5 1016  5 5 5 5 5 5 5 5 5 1028  5 5 4 5 5 5 5 5 5 1040  5 5 4 5 5 5 5 5 5 1052  5 5 3 5 5 5 5 5 5 1064  5 5 4 5 5 5 5 5 5 1085  5 5 4 5 5 5 5 5 5 1087  5 5 5 5 5 5 5 5 5 1088  5 5 5 5 5 5 5 5 5 1112  5 5 5 5 5 5 5 5 5 1124  5 5 5 5 5 5 5 5 5 1136  5 5 5 5 5 5 5 5 5 1148  5 5 4 5 5 5 5 5 5 1160  5 5 4 5 5 5 5 5 5 1171  5 5 4 5 5 5 5 4 5 1173  5 5 5 5 5 5 5 5 5 1197  5 5 5 5 5 5 5 5 5 1209  5 5 5 5 5 5 5 5 5 1233  5 5 5 5 5 5 5 5 5 1245  5 5 5 5 5 5 5 5 5 1269  5 5 4 5 5 5 5 5 5 1294  5 5 4 5 5 5 5 5 5 1305  5 5 5 5 5 5 5 5 5 1306  5 5 5 5 5 5 5 5 5 1311  5 5 5 5 5 5 5 5 5 1314  5 4 3 5 5 5 4 4 5 1315  5 5 5 5 5 5 5 5 5 1318  5 5 3 5 5 5 4 4 5 1327  5 5 3 5 5 5 4 4 5

Test Example 4

Herbicidal Effect on Upland Weeds After Emergence

[0376] Polyethylene-made vats having a size of 10 cm (length)×20 cm (width)×5 cm (height) were filled with soil, sown with seeds of the following noxious upland weeds and with seeds of soybean plant and wheat as upland crop plants, and then covered with soil. The plants were made to grow up until they reached the leaf-stages mentioned below, after which an agent comprising a prescribed concentration of a compound of the present invention (listed in Tables 1 to 14) as active ingredient was sprayed.

[0377] Fourteen days after the treatment, the herbicidal effect was investigated, from which weed-killing rate was calculated in the same manner as in Test Example 1 and the results were judged. At the same time, phytotoxicity on soybean plant and wheat was investigated and judged in the same manner as in Test Example 3.

[0378] Sample weeds, their leaf stages, and leaf stages of soybean plant and wheat were as follows: 21 Foxtail grass (Am) 1-2 leaved stage Barnyard grass (Ec) 1-2 leaved stage Velvetleaf (At) 2-leaved stage Cocklebur (Xs) 2-leaved stage Cleavers (Ga) 1-leaved stage Bird's eye speedwell (Vp) Cotyledon to 1-leaved stage Wheat (Eh) 2-leaved stage Soybean plant (So) 1-leaved stage The results are summarized in Table 17.

[0379] 22 TABLE 17 Dosage Phytotoxicity Herbicidal effect No (kg/ha) Wh So Am Ec At Xs Ga Vp  1 5 2 1 3 4 5 4 3 5  2 5 2 1 4 5 5 4 5 5  3 5 3 2 5 5 5 4 5 5  28 5 1 0 2 3 3 2 2 4  29 5 1 0 3 3 4 3 3 4  30 5 2 1 4 4 5 3 3 5  43 5 1 0 2 3 3 2 1 3  44 5 1 0 3 3 3 2 3 4  53 5 1 0 3 3 4 2 2 3  58 5 3 2 4 4 5 3 3 4  71 5 4 2 4 4 4 3 3 5  97 5 0 0 2 2 2 1 1 3  99 5 4 2 4 5 5 4 4 5 100 5 2 3 4 5 5 4 5 5 101 5 3 2 4 5 5 4 4 5 126 5 0 0 2 2 3 1 1 3 127 5 2 1 3 3 3 1 2 3 128 5 2 1 4 4 4 3 3 5 129 5 4 2 5 5 5 5 5 5 130 5 3 1 4 5 5 4 4 5 157 5 3 2 4 5 5 4 4 5 158 5 4 2 4 5 5 4 5 5 189 5 2 0 3 3 4 2 3 4 200 5 0 0 2 3 3 1 1 3 201 5 0 0 3 2 3 1 1 3 219 5 2 1 4 5 5 3 3 5 224 5 2 1 3 4 4 2 2 4 228 5 1 1 3 3 4 1 2 4 234 5 0 0 2 3 3 1 1 3 243 5 0 0 2 3 3 1 1 3 246 5 1 0 3 3 4 2 2 4 275 5 2 1 3 4 4 3 3 4 276 5 3 2 4 5 5 4 4 5 289 5 2 1 4 5 5 3 4 5 290 5 3 2 5 5 5 4 5 5 291 5 2 2 4 5 5 4 4 5 305 5 2 1 3 4 4 2 2 4 310 5 2 0 3 4 4 3 2 3 334 5 2 1 3 4 4 3 3 4 339 5 2 1 3 4 4 2 2 4 343 5 0 0 2 4 3 2 2 3   359-1 5 2 3 5 5 5 5 5 5   359-2 5 3 4 5 5 5 5 5 5   359-3 5 2 3 5 5 5 5 5 5   359-4 5 2 4 5 5 5 5 5 5   359-5 5 3 2 5 5 5 5 5 5   359-6 5 2 3 5 5 5 5 5 5 360 5 4 3 5 5 5 5 4 5 361 5 5 4 5 5 5 5 5 5 375 5 4 4 5 5 5 5 5 5 388 5 5 4 5 5 5 5 5 5 414 5 5 4 5 5 5 5 5 5 423 5 5 4 5 5 5 5 5 5 431 5 4 3 4 4 5 4 4 5 438 5 5 4 5 5 5 5 5 5 447 5 5 4 5 5 5 5 5 5 450 5 4 4 5 5 5 4 4 5 462 5 5 5 5 5 5 5 5 5 474 5 3 3 5 5 5 4 4 5 486 5 4 4 5 5 5 5 5 5 498 5 4 4 5 5 5 4 4 5 510 5 5 4 5 5 5 5 5 5 519 5 5 4 5 5 5 5 5 5 527 5 5 5 5 5 5 4 5 5 534 5 4 4 5 5 5 5 5 5 558 5 5 5 5 5 5 5 5 5 570 5 4 4 5 5 5 4 4 5 582 5 4 4 5 5 5 5 5 5 606 5 4 3 5 5 5 4 4 5 630 5 4 3 5 5 5 4 4 5 654 5 3 2 3 3 4 2 2 4 678 5 4 3 4 5 5 3 3 5 679 5 3 2 4 5 5 4 4 5 703 5 3 2 4 5 5 4 4 5 724 5 3 2 4 4 4 3 4 5 727 5 4 4 5 5 5 4 4 5 739 5 5 4 5 5 5 5 5 5 760 5 4 3 5 5 5 4 5 5 763 5 4 3 4 5 5 4 4 5 774 5 5 4 5 5 5 5 5 5 775 5 5 5 5 5 5 5 5 5 796 5 4 4 5 5 5 4 4 5 798 5 5 4 5 5 5 5 5 5 799 5 5 5 5 5 5 5 5 5 811 5 5 4 5 5 5 4 4 5 814 5 4 3 5 5 5 4 4 5 824 5 5 4 5 5 5 5 5 5 836 5 5 4 5 5 5 5 5 5 847 5 5 4 5 5 5 5 5 5 870 5 4 3 5 5 5 5 5 5 871 5 5 4 5 5 5 5 5 5 892 5 4 3 5 5 5 4 4 5 894 5 5 4 5 5 5 4 5 5 895 5 5 4 5 5 5 5 5 5 907 5 5 4 5 5 5 5 5 5 919 5 5 5 5 5 5 5 5 5 934 5 5 4 5 5 5 4 5 5 943 5 4 4 5 5 5 5 5 5 955 5 5 3 5 5 5 5 5 5 976 5 5 4 5 5 5 5 5 5 980 5 5 4 5 5 5 5 5 5 992 5 5 5 5 5 5 5 5 5 1016  5 5 5 5 5 5 5 5 5 1028  5 5 4 5 5 5 5 4 5 1040  5 5 4 5 5 5 5 5 5 1052  5 5 3 5 5 5 5 5 5 1064  5 5 4 5 5 5 5 5 5 1085  5 5 4 5 5 5 5 4 5 1087  5 5 4 5 5 5 5 5 5 1088  5 5 5 5 5 5 5 5 5 1112  5 5 5 5 5 5 5 5 5 1124  5 5 5 5 5 5 5 5 5 1136  5 5 5 5 5 5 5 5 5 1148  5 5 4 5 5 5 5 5 5 1160  5 5 4 5 5 5 5 5 5 1171  5 4 3 5 5 5 4 4 5 1173  5 5 5 5 5 5 5 5 5 1197  5 5 5 5 5 5 5 5 5 1209  5 5 5 5 5 5 5 5 5 1233  5 5 5 5 5 5 5 5 5 1245  5 5 5 5 5 5 5 5 5 1269  5 5 4 5 5 5 5 5 5 1294  5 5 4 5 5 5 5 5 5 1305  5 5 5 5 5 5 5 5 5 1306  5 5 5 5 5 5 5 5 5 1311  5 5 5 5 5 5 5 5 5 1314  5 4 4 5 5 5 4 4 5 1315  5 5 5 5 5 5 5 5 5 1318  5 4 3 5 5 5 4 5 5 1327  5 4 3 5 5 5 4 5 5

Claims

1. A fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) or a salt thereof:

39

wherein R1 represents hydrogen atom or (C1-C6) alkyl group;

R2 and R3 may be same or different and each represents hydrogen atom, (C1-C8) alkyl group, halo (C1-C6) alkyl group, (C3-C8) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C1-C6) alkoxy group, (C1-C1) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, alkylthio (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, amino (C1-C6) alkyl group, substituted amino (C1-C6) alkyl group substituted with one or two, same or different (C1-C6) alkyl groups, phenyl (C1-C6) alkyl group, substituted phenyl (C1-C6) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups, phenyl (C1-C6) alkoxy group or substituted phenyl (C1-C6) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups; or

R2 and R3, taken conjointly, represent a 5- to 6-membered heterocycle having at least one, same or different heteroatoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, further, the carbon atom or nitrogen atom on said heterocycle may have at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group and halo (C1-C6) alkylthio group;

X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, amino group, substituted amino group substituted with same or different (C1-C6) alkyl groups, cyano (C1-C6) alkyl groups, phenyl (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl groups, (C1-C6) acyl groups, (C1-C6) alkylsulfonyl groups or halo (C1-C6) alkylsulfonyl groups, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C1) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenyl (C1-C6) alkyl group or substituted phenyl (C1-C6) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group; and

40

represents Q1, Q2, Q3, Q4, Q5, Q6 Q7, Q8, Q9, Q10, Q11, Q12, Q13 or Q14, wherein:

Q1 is a group of the following formula:

41

wherein Y represents hydrogen atom, halogen atom, nitro group, cyano group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, amino group, substituted amino group having at least one, same or different substituents selected from the group consisting of (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkoxyaminocarbonyl group, (C1-C6) acyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl (C1-C6) alkyl group, (C3-C5) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C1-C6) alkyl groups; and

R4 represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, methylenedioxy group, amino group and substituted amino group substituted with at least one, same or different (C1-C6) alkyl groups, cyano (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl groups, (C1-C6) alkoxyaminocarbonyl groups, (C1-C6) acyl groups, (C1-C6) alkylsulfonyl groups, halo (C1-C6) alkylsulfonyl groups or phenyl (C1-C6) alkyl groups;

Q2 is a group of the following formula:

42

wherein at least one of A, B, D and E represent a nitrogen atom, and the others of A, B, D and E represent C-R5 wherein R5 represents hydrogen atom, halogen atom, nitro group, cyano group, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C1) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, amino group or substituted amino group having at least one, same or different substituents selected from the group consisting of (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkoxyaminocarbonyl group, (C1-C6) acyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl (C1-C6) alkyl group; and Y is as defined above;

Q3 is a group of the following formula:

43

wherein at least one of F, G, J and K represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N-R6 wherein R6 represents hydrogen atom, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylsulfonyl group or halo (C1-C6) alkylsulfonyl group, and the others of F, G, J and K each represents C—(R7)R8 wherein R7 and R8 may be same or different and represent hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, phenyl (C1-C6) alkyl group, substituted phenyl (C1-C6) alkyl group substituted with at least one, same or different halogen atoms or (C1-C6) alkyl groups, amino (C1-C6) alkyl group, substituted amino (C1-C6) alkyl group substituted with at least one, same or different (C1-C6) alkyl groups or phenyl (C1-C6) alkoxy group; and Y is as defined above; and G and J may be taken conjointly to represent CH═CH;

Q4 is a group of the following formula:

44

wherein R9 is same or different and represents halogen atom, nitro group, cyano group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C1) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, amino group, substituted amino group substituted with at least one, same or different substituents selected from the group consisting of (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkoxyaminocarbonyl group, (C1-C6) acyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl (C1-C6) alkyl group, (C3-C5) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C1-C6) alkyl groups; m represents an integer of 0 to 2;

Z represents oxygen atom, sulfur atom or N-R10 wherein R10 represents hydrogen atom, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group or (C1-C6) alkylthio (C1-C6) alkyl group; and Y is as defined above;

Q5 is a group of the following formula:

45

wherein R9, Y, Z and m are as defined above;

Q6 is a group of the following formula:

46

wherein R9, Y, Z and m are as defined above;

Q7 is a group of the following formula:

47

wherein at least one of L, M and T represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N—R11 wherein R11 represents hydrogen atom, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C1) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group or (C1-C6) alkylthio (C1-C6) alkyl group, and the others of L, M and T each represents C—(R12)R13 wherein R12 and R13 may be same or different and each represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, phenyl (C1-C6) alkyl group, substituted phenyl (C1-C1) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups, phenyl (C1-C6) alkoxy group, substituted phenyl (C1-C6) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups, amino (C1-C6) alkyl group or substituted amino (C1-C6) alkyl group substituted with at least one, same or different (C1-C6) alkyl groups;

Q8 is a group of the following formula:

48

wherein R14 represents hydrogen atom or is the same as R9, and Y and Z are as defined above;

Q9 is a group of the following formula:

49

wherein R14, Y and Z are as defined above;

Q10 is a group of the following formula:

50

wherein R14, Y and Z are as defined above;

Q11 is a group of the following formula:

51

wherein R Y and Z are as defined above;

Q12 is a group of the following formula:

52

wherein R14, Y and Z are as defined above;

Q13 is a group of the following formula:

53

wherein R14, Y and Z are as defined above; and

Q14 is a group of the following formula:

54

wherein R9 is as defined above and n represents an integer of 0 to 4.

2. A fused heterocyclic dicarboxylic acid diamide derivative or a salt thereof according to claim 1, wherein:

R1 represents hydrogen atom;

R2 and R3 may be same or different and each represents hydrogen atom, (C1-C8) alkyl group or (C3-C8) cycloalkyl group; and

X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group and (C1-C6) alkoxycarbonyl group; and

55

represents Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13 or Q14, wherein

Q1 is a group of the following formula:

56

wherein Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group;

R4 represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, hydroxyl group, (C1-C6) alkoxy group and methylenedioxy group;

Q2 is a group of the following formula:

57

wherein A represents nitrogen atom; B, D or E represents C—R5 wherein R5 represents hydrogen atom, halogen atom, (C1-C6) alkyl group or halo (C1-C1) alkyl group; and Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C1) cycloalkyl group;

Q3 is a group of the following formula:

58

wherein at least one of F, G, J and K represents oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N-R6 wherein R6 represents hydrogen atom, (C1-C6) alkyl group or halo (C1-C6) alkyl group, and the others of F, G, J and K represent C—(R7)R8 wherein R7 and R8 represent hydrogen atom; and Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and G and J may be taken conjointly to form CH═CH;

Q4 is a group of the following formula:

59

wherein R9 is same or different and represents halogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; m represents an integer of 0 to 2; Z represents oxygen atom, sulfur atom or N—R10 wherein R10 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group;

Q5 is a group of the following formula:

60

wherein R9 is same or different and represents halogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; m represents an integer of 0 to 2; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents oxygen atom or sulfur atom;

Q6 is a group of the following formula:

61

wherein R9 is same or different and represents halogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; m represents an integer of 0 to 2; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents oxygen atom, sulfur atom or N—R10 wherein R10 is as defined above;

Q7 is a group of the following formula:

62

wherein at least one of L, M and T represents oxygen atom, sulfur atom, sulfinyl group, sulfonyl group or N—R11 wherein R11 represents hydrogen atom, (C1-C6) alkyl group or halo (C1-C6) alkyl group; and the others of L, M and T represent C—(R12)R13 wherein R12 and R13 may be same or different and represent hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C1-C6) alkoxy group; and Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group;

Q8 is a group of the following formula:

63

wherein R14 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents oxygen atom, sulfur atom or N-R10 wherein R10 is as defined above;

Q9 is a group of the following formula:

64

wherein R 14 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents N-R10 wherein R10 is as defined above;

Q10 is a group of the following formula:

65

wherein R14 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents N-R10 wherein R10 is as defined above;

Q11 is a group of the following formula:

66

wherein R14 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents N-R10 wherein R10 is as defined above;

Q12 is a group of the following formula:

67

wherein R14 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents N-R10 wherein R10 is as defined above;

Q13 is a group of the following formula:

68

wherein R14 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents N-R10 wherein R10 is as defined above; and

Q14 is a group of the following formula:

69

wherein R9 is same or different and represents halogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and m represents an integer of 0 to 2.

3. A fused heterocyclic dicarboxylic acid diamide derivative or a salt thereof according to claim 2, wherein R1 represents hydrogen atom; R2 represents hydrogen atom; R3 represents hydrogen atom, (C1-C8) alkyl group or (C3-C8) cycloalkyl group; X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group and halo (C1-C6) alkoxy group; and

70

represents Q1, Q2, Q3, Q4, Q5, Q7, Q8,or Q11, wherein:

Q1 is a group of the following formula:

71

wherein Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and R4 represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, hydroxyl group, (C1-C6) alkoxy group and methylenedioxy group;

Q2 is a group of the following formula:

72

wherein A represents nitrogen atom; B, D or E represents C—R5 wherein R5 represents hydrogen atom, halogen atom, (C1-C6) alkyl group or halo (C1-C6) alkyl group; and Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group;

Q3 is a group of the following formula:

73

wherein at least one of F, G, J and K represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N—R6 wherein R6 represents hydrogen atom, (C1-C6) alkyl group or halo (C1-C6) alkyl group, and the others of F, G, J and K represent C—(R7)R8 wherein R7 and R8 represent hydrogen atom; and Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; further G and J may be taken conjointly to form CH═CH;

Q4 is a group of the following formula:

74

wherein R9 is same or different and represents halogen atom, (C1-C6) alkyl group or (C3-C1) cycloalkyl group; m represents an integer of 0 to 2; Z represents oxygen atom, sulfur atom or N—R10 wherein R10 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group;

Q5 is a group of the following formula:

75

wherein R9 is same or different and represents halogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; m represents an integer of 0 to 2; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents oxygen atom, sulfur atom or N-R10 wherein R10 is as defined above;

Q7 is a group of the following formula:

76

wherein at least one of L, M and T represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group or N-R11 wherein R11 represents hydrogen atom, (C1-C6) alkyl group or halo (C1-C6) alkyl group, and the others of L, M and T represent C—(R12) R13 wherein R12 and R13 may be same or different and each represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C1-C6) alkoxy group; and Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group;

Q8 is a group of the following formula:

77

wherein R14 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents oxygen atom, sulfur atom or N—R10 wherein R10 is as defined above; and

Q11 is a group of the following formula:

78

wherein R14 represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group or (C3-C6) cycloalkyl group; Y represents hydrogen atom, (C1-C6) alkyl group or (C3-C6) cycloalkyl group; and Z represents N-R10 wherein R10 is as defined above.

4. A herbicide characterized by containing a fused heterocyclic dicarboxylic acid diamide derivative or a salt thereof according to any of claims 1 to 3 as an active ingredient.

5. A method for using a herbicide characterized by applying an effective amount of a herbicide according to claim 4 to a weed or a soil for the purpose of controlling a weed undesirable for the growth of useful plants.