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US20030073582A1 - Fused heterocyclic dicarboxylic acid diamide derivatives or salts thereof, herbicide and method for using the same - Google Patents

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

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US20030073582A1
US20030073582A1 US10/133,444 US13344402A US2003073582A1 US 20030073582 A1 US20030073582 A1 US 20030073582A1 US 13344402 A US13344402 A US 13344402A US 2003073582 A1 US2003073582 A1 US 2003073582A1
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group
alkyl group
halo
alkyl
cycloalkyl
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US10/133,444
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Hideo Takaishi
Takeshi Katsuhira
Hiroshi Yamaguchi
Youichi Kawabata
Hiroto Harayama
Yoshiki Oda
Masahiko Murai
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Nihon Nohyaku Co Ltd
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Assigned to NIHON HOHYAKU CO., LTD. reassignment NIHON HOHYAKU CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ODA, YOSHIKI, KATSUHIRA, TAKESHI, KAWABATA, YOUICHI, MURAI, MASAHIKO, RARAYAMA, HIROTO, TAKAISHI, HIDEO, YAMAGUCHI, HIROSHI
Publication of US20030073582A1 publication Critical patent/US20030073582A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • 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.
  • JP-A-6-2519 there is mentioned that pyrazinedicarboxylic acid diamide derivatives are useful as herbicide.
  • JP-A-9-323974 there is mentioned that pyridinedicarboxylic acid diamide derivatives are useful as herbicide.
  • the present invention relates to fused heterocyclic dicarboxylic acid diamide derivatives represented by the following general formula (I):
  • R 1 represents hydrogen atom or (C 1 -C 6 ) alkyl group
  • R 2 and R 3 may be same or different and each represents hydrogen atom, (C 1 -C 8 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 3 -C 8 ) cycloalkyl group, (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylthio group, alkylthio (C 1 -C 6 ) alkyl group, cyano (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl
  • R 2 and R 3 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, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkylthio group and halo (C 1 -C 6 ) alkylthio group;
  • X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkylthio group, halo (C 1 -C 1 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, halo (C 1 -C 6 ) alkyl
  • [0009] represents Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 , Q 8 , Q 9 , Q 10 , Q 11 , Q 12 , Q 13 or Q 14 , wherein:
  • Q 1 is a group of the following formula:
  • Y represents hydrogen atom, halogen atom, nitro group, cyano group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, (C 1 -C 1 ) alkoxy group, halo (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylthio group, halo (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, halo (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulf
  • R 4 represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, hydroxyl group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, (c 3 -c 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkoxy (C 1 -C 1 ) alkyl group, (C 1 -C 6 ) alkylthio group, halo (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, halo (C 1 -C 6 ) alkylsulfinyl group, hal
  • Q 2 is a group of the following formula:
  • A, B, D and E represent a nitrogen atom
  • the others of A, B, D and E represent C-R 5 wherein R 5 represents hydrogen atom, halogen atom, nitro group, cyano group, hydroxyl group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, (C 3 -C 1 ) cycloalkyl (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylthio group, halo (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfiny
  • Q 3 is a group of the following formula:
  • F, G, J and K represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N-R 6 wherein R 6 represents hydrogen atom, hydroxyl group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxycarbonyl group, (C 1 -C 6 ) alkylsulfonyl group or halo (C 1
  • Q 4 is a group of the following formula:
  • R 9 is same or different and represents halogen atom, nitro group, cyano group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxycarbonyl group, (C 1 -C 6 ) alkylthio group, halo (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, halo (C 1 -C 6 ) alkylsulfinyl group, hal
  • Z represents oxygen atom, sulfur atom or N-R 10 wherein R 10 represents hydrogen atom, hydroxyl group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxycarbonyl group, (C 1 -C 6 ) alkylsulfonyl group, halo (C 1 -C 6 ) alkylsulfonyl group or (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group; and Y is as defined above;
  • Q 5 is a group of the following formula:
  • R 9 , Y, Z and m are as defined above;
  • Q 6 is a group of the following formula:
  • R 9 , Y, Z and m are as defined above;
  • Q 7 is a group of the following formula:
  • L, M and T represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N—R 11 wherein R 11 represents hydrogen atom, hydroxyl group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) cycloalkyl group, (C 1 -C 1 ) cycloalkyl (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxycarbonyl group, (C 1 -C 6 ) alkylsulfonyl group, halo (C 1 -C 6 ) alkylsulfonyl group or (C 1 -C 6 ) alkylthi
  • Q 8 is a group of the following formula:
  • R 14 represents hydrogen atom or is the same as R 9 , and Y and Z are as defined above;
  • Q 9 is a group of the following formula:
  • R 14 , Y and Z are as defined above;
  • Q 10 is a group of the following formula:
  • R 14 , Y and Z are as defined above;
  • Q 1 is a group of the following formula:
  • R 14 Y and Z are as defined above;
  • Q 12 is a group of the following formula:
  • R 14 , Y and Z are as defined above;
  • Q 13 is a group of the following formula:
  • R 14 , Y and Z are as defined above;
  • Q 14 is a group of the following formula:
  • R 9 is as defined above and n represents an integer of 0 to 4.
  • salts of said compounds a herbicide containing said compound as an active ingredient, and a method for using said herbicide.
  • halogen atom means chlorine atom, bromine atom, iodine atom or fluorine atom;
  • C 1 -C 8 means that the number of carbon atoms is 1 to 8;
  • the term (C 1 -C 8 ) alkyl group for example, means a straight chain or branched chain alkyl group having 1 to 8 carbon atoms;
  • the term “halo (C 1 -C 6 ) 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.
  • 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
  • salts of metal ions such as sodium ion, potassium ion, calcium ion and the like
  • Q 2 , Q 3 , Q 4 , Q 6 , Q 7 , Q 8 , Q 11 or the like can be referred to.
  • cases where X is substituted at the 2- and 3-positions or at the 2-, 3- and 6-positions can be referred to.
  • fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) can be produced, for example, according to the production process schematically shown below.
  • hal represents a halogen atom.
  • 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.
  • inert solvents 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.
  • 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).
  • 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.
  • 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.
  • 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.
  • 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.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like
  • aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and the like
  • 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).
  • the dehydrating agent is used in an equimolar quantity.
  • 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.
  • the reaction time may vary with scale and temperature of the reaction, and it ranges from several minutes to 48 hours.
  • 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.
  • any inert solvent may be used so far as it does not obstruct progress of the reaction greatly.
  • 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.
  • aromatic hydrocarbons such as benzene, toluene, xylene and the like
  • halogenated hydrocarbons such as methylene chlor
  • 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.
  • 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.
  • the reaction time may vary with scale and temperature of the reaction, and it ranges from several minutes to 48 hours.
  • 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.
  • 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.
  • 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.
  • the inert solvents usable in this reaction the inert solvents exemplified in B and pyridines can be referred to.
  • 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.
  • a base must be used for the purpose of generating a free amine in the reaction system.
  • an inorganic amine or an organic amine can be used.
  • 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.
  • 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.
  • 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.
  • the reaction time may vary with temperature and scale of the reaction, and it ranges from several minutes to 48 hours.
  • 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.
  • 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.
  • 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
  • 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 (
  • 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.
  • 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.
  • 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.
  • the time of application is not limited thereto, but it is also possible to control the weeds in the growth stage.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 dimethyl
  • a surfactant is used.
  • 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.
  • adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohols, turpentine, bran oil, bentonite and ligninsulfonates.
  • adjuvants such as waxes, stearates and alkyl phosphates.
  • Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products.
  • Adjuvants such as silicone oil may also be used as a defoaming agent.
  • the content of the active ingredient may be varied according to the need.
  • the suitable content thereof is from 0.01 to 50% by weight.
  • the suitable content is from 0.01 to 50% by weight.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • part means part by weight.
  • An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.
  • a dust was prepared by mixing uniformly and grinding the above ingredients.
  • 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.
  • a wettable powder was prepared by mixing uniformly and grinding the above ingredients.
  • 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.
  • 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.

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Abstract

A fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I):
Figure US20030073582A1-20030417-C00001
wherein R1 is H, (C1-C6) alkyl; R2 and R3 are H, (halo) (C1-C6) alkyl, (C3-C1) cycloalkyl, substituted amino (C1-C6) alkyl, (substituted) phenyl (C1-C1) alkyl, (substituted) phenyl (C1-C6) alkoxy or the like or R2 and R3, taken conjointly, represent a (substituted) 5- or 6-membered heterocycle having at least one of O, S and N; X is H, halogen, NO2, CN, (C1-C6) alkyl, (substituted) phenyl, (substituted) phenoxy or the like;
Figure US20030073582A1-20030417-C00002
is
Figure US20030073582A1-20030417-C00003
or the like wherein Y, R4 and R9 are H, halogen, NO2, CN, (C1-C6) alkyl or the like, and A, B, D, E, F, G, J and K are O, S, N, sulfinyl or the like; and a herbicide containing said derivative as active ingredient.

Description

    TECHNICAL FIELD
  • 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. [0001]
    • BACKGROUND ART
  • 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. [0002]
    • DISCLOSURE OF THE INVENTION
  • 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. [0003]
  • The present invention relates to fused heterocyclic dicarboxylic acid diamide derivatives represented by the following general formula (I): [0004]
    Figure US20030073582A1-20030417-C00004
  • wherein R[0005] 1 represents hydrogen atom or (C1-C6) alkyl group;
  • R[0006] 2 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
  • R[0007] 2 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, (C[0008] 1-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
    Figure US20030073582A1-20030417-C00005
  • represents Q[0009] 1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13 or Q14, wherein:
  • Q[0010] 1 is a group of the following formula:
    Figure US20030073582A1-20030417-C00006
  • wherein Y represents hydrogen atom, halogen atom, nitro group, cyano group, (C[0011] 1-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
  • R[0012] 4 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;
  • Q[0013] 2 is a group of the following formula:
    Figure US20030073582A1-20030417-C00007
  • 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-R[0014] 5 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;
  • Q[0015] 3 is a group of the following formula:
    Figure US20030073582A1-20030417-C00008
  • wherein at least one of F, G, J and K represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N-R[0016] 6 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;
  • Q[0017] 4 is a group of the following formula:
    Figure US20030073582A1-20030417-C00009
  • wherein R[0018] 9 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;
  • Z represents oxygen atom, sulfur atom or N-R[0019] 10 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;
  • Q[0020] 5 is a group of the following formula:
    Figure US20030073582A1-20030417-C00010
  • wherein R[0021] 9, Y, Z and m are as defined above;
  • Q[0022] 6 is a group of the following formula:
    Figure US20030073582A1-20030417-C00011
  • wherein R[0023] 9, Y, Z and m are as defined above;
  • Q[0024] 7 is a group of the following formula:
    Figure US20030073582A1-20030417-C00012
  • wherein at least one of L, M and T represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N—R[0025] 11 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;
  • Q[0026] 8 is a group of the following formula:
    Figure US20030073582A1-20030417-C00013
  • wherein R[0027] 14 represents hydrogen atom or is the same as R9, and Y and Z are as defined above;
  • Q[0028] 9 is a group of the following formula:
    Figure US20030073582A1-20030417-C00014
  • wherein R[0029] 14, Y and Z are as defined above;
  • Q[0030] 10 is a group of the following formula:
    Figure US20030073582A1-20030417-C00015
  • wherein R[0031] 14, Y and Z are as defined above;
  • Q[0032] 1 is a group of the following formula:
    Figure US20030073582A1-20030417-C00016
  • wherein R[0033] 14 Y and Z are as defined above;
  • Q[0034] 12 is a group of the following formula:
    Figure US20030073582A1-20030417-C00017
  • wherein R[0035] 14, Y and Z are as defined above;
  • Q[0036] 13 is a group of the following formula:
    Figure US20030073582A1-20030417-C00018
  • wherein R[0037] 14, Y and Z are as defined above; and
  • Q[0038] 14 is a group of the following formula:
    Figure US20030073582A1-20030417-C00019
  • wherein R[0039] 9 is as defined above and n represents an integer of 0 to 4; and
  • salts of said compounds, a herbicide containing said compound as an active ingredient, and a method for using said herbicide. [0040]
  • 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 (C[0041] 1-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.
  • 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. [0042]
  • As a preferable embodiment of the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I), a case where R[0043] 1 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
    Figure US20030073582A1-20030417-C00020
  • is Q[0044] 2, 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.
  • 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. [0045]
  • Production Process [0046]
    Figure US20030073582A1-20030417-C00021
  • wherein R[0047] 2, R3, X and
    Figure US20030073582A1-20030417-C00022
  • are as defined above, and hal represents a halogen atom. [0048]
  • 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. [0049]
  • A. General formula (VIII)→General formula (VII) [0050]
  • 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. [0051]
  • 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). [0052]
  • 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. [0053]
  • 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. [0054]
  • It is also possible to use the product obtained in this step in the subsequent reaction without isolation. [0055]
  • B. General formula (VII)→General formula (VI) [0056]
  • 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. [0057]
  • It is also possible to replace the inert solvent with an excessive quantity of the dehydrating agent. [0058]
  • 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. [0059]
  • 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. [0060]
  • The reaction time may vary with scale and temperature of the reaction, and it ranges from several minutes to 48 hours. [0061]
  • 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. [0062]
  • 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. [0063]
  • It is also possible to use the objective product in the subsequent reaction without isolation. [0064]
  • C. General formula (VI)→General formula (IV-1)+General formula (IV-2) [0065]
  • 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. [0066]
  • 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. [0067]
  • 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. [0068]
  • The reaction time may vary with scale and temperature of the reaction, and it ranges from several minutes to 48 hours. [0069]
  • 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. [0070]
  • It is also possible to use the objective product in the subsequent reaction without isolation. [0071]
  • D. General formula (IV-1) +General formula (IV-2)→General formula (III) [0072]
  • 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. [0073]
  • Hereunder are shown typical examples of the imide represented by general formula (III). [0074]
  • (1). N-(3-Chloro-2,6-diethylphenyl)-1,3-dimethylpyrazolo[5,4-b]pyridine-5,6-dicarboximide [0075] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.09(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz), [0076]
  • 2.43(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz), [0077]
  • 2.69(3H,s), 4.26(3H,s), 7.21(1H,d,J=8.4 Hz), [0078]
  • 7.47(1H,d,J=8.4 Hz), 8.61(1H,s) [0079]
  • (2). N-(3-chloro-2,6-diethylphenyl)thieno[3,2-b]pyridine-5,6-dicarboximide [0080] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 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), [0081]
  • 7.20(1H,d,J=8.4 Hz), 7.47(1H,d,J=8.4 Hz), [0082]
  • 7.90(1H,d,J=5.7 Hz), 8.17(1H,d,J=5.7 Hz), [0083]
  • 8.79(1H,s). [0084]
  • (3). N-(3-chloro-2,6-diethylphenyl)-2,3-dihydrothieno-[3,2-b]pyridine-5,6-dicarboximide [0085] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.06(3H,t,J=7.5 Hz), 1.12(3H,t,J=7.5 Hz), [0086]
  • 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), [0087]
  • 7.44(1H,d,J=8.4 Hz), 7.95(1H,s). [0088]
  • (4). N-(3-chloro-2,6-diethylphenyl)-2,3-dihydrothieno-[2,3-b]pyridine-5,6-dicarboximide [0089] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.05(3H,t,J=7.5 Hz), 1.11(3H,t,J=7.5 Hz), [0090]
  • 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), [0091]
  • 7.43(1H,d,J=8.4 Hz), 7.85(1H,s). [0092]
  • (5). N-(3-chloro-2,6-diethylphenyl)-furo[2,3-b]pyridine-5,6-dicarboximide [0093] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.08(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz), [0094]
  • 2.43(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz), [0095]
  • 7.11(1H,d,J=2.6 Hz), 7.24(1H,d,J=8.4 Hz), [0096]
  • 7.47(1H,d,J=8.4 Hz), 8.05(1H,d,J=2.6 Hz), [0097]
  • 8.53(1H,s). [0098]
  • (6). N-(3-chloro-2,6-diethylphenyl)-1-methyl-pyrrolo-[3,2-b]pyridine-5,6-dicarboximide [0099]
  • [0100] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.04(3H,t,J=7.5 Hz), 1.08(3H,t,J=7.5 Hz), [0101]
  • 2.45(2H,q,J=7.5 Hz), 2.65(2H,q,J=7.5 Hz), [0102]
  • 3.93(3H,s), 6.95(1H,d,J=0.6 Hz), [0103]
  • 7.15(1H,d,J=8.0 Hz), 7.38(1H,d,J=8.0 Hz), [0104]
  • 7.61(1H,d,J=0.6 Hz), 8.17(1H,s). [0105]
  • (7). N-(3-chloro-2,6-diethylphenyl)-1-methoxy-pyrrolo-[3,2-b]pyridine-5,6-dicarboximide [0106]
  • [0107] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.06(3H,t,J=7.5 Hz), 1.11(3H,t,J=7.5 Hz), [0108]
  • 2.42(2H,q,J=7.5 Hz), 2.65(2H,q,J=7.5 Hz), [0109]
  • 4.21(3H,s), 6.90(1H,d,J=0.6 Hz), [0110]
  • 7.15(1H,d,J=8.0 Hz), 7.38(1H,d,J=8.0 Hz), [0111]
  • 7.81(1H,d,J=0.6 Hz), 8.32(1H,s) [0112]
  • (8). N-(3-chloro-2,6-diethylphenyl)-1,8-naphthylidine-2,3-dicarboximide [0113]
  • [0114] 1H-NMR [TMS/CDCl3, δ (ppm)
  • 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz), [0115]
  • 2.43(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz), [0116]
  • 7.24(1H,d,J=8.4 Hz), 7.52(1H,d,J=8.4 Hz), [0117]
  • 8.05(1H,dd,J=2.9 and 7.9 Hz), 8.81(1H,d,J=7.9 Hz), [0118]
  • 9.04(1H,s), 9.62(1H,d,J=2.9 Hz). [0119]
  • (9). N-(3-chloro-2,6-diethylphenyl)-5-oxo-5,6,7,8-tetrahydroquinoline-2,3-dicarboximide [0120]
  • [0121] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz), [0122]
  • 2.30(2H,m), 2.43(2H,q,J=7.5 Hz), 2.48(2H,m), [0123]
  • 2.61(2H,q,J=7.5 Hz), 2.85(2H,m), [0124]
  • 7.19(1H,d,J=8.4 Hz), 7.42(1H,d,J=8.4 Hz), [0125]
  • 8.89(1H,s). [0126]
  • (10). N-(3-chloro-2,6-diethylphenyl)-6-methyl-5,6,7,8-tetrahydro-1,6-naphthylidine-2,3-dicarboximide [0127]
  • [0128] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz), [0129]
  • 2.33(2H,q,J=7.5 Hz), 2.52(2H,q,J=7.5 Hz), [0130]
  • 2.95(3H,s), 3.00-3.12(4H,m), 3.54(2H,m), [0131]
  • 7.15(1H,d,J=8.4 Hz), 7.42(1H,d,J=8.4 Hz), [0132]
  • 8.02(1H,s). [0133]
  • (11). N-(3-chloro-2,6-diethylphenyl)-7,8-dihydro-5H-thiopyrano[4,3-b]pyridine-2,3-dicarboximide [0134]
  • [0135] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.08(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz), [0136]
  • 2.39(2H,q,J=7.5 Hz), 2.58(2H,q,J=7.5 Hz), [0137]
  • 3.11(2H,t,J=5.8 Hz), 3.52(2H,t,J=5.8 Hz), [0138]
  • 3.97(2H,s), 7.19(1H,d,J=8.4 Hz), [0139]
  • 7.46(1H,d,J=8.4 Hz), 8.08(1H,s). [0140]
  • (12). N-(3-chloro-2,6-diethylphenyl)-7,8-dihydro-5H-pyrano[4,3-b]pyridine-2,3-dicarboximide [0141]
  • [0142] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.07(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz), [0143]
  • 2.39(2H,q,J=7.5 Hz), 2.58(2H,q,J=7.5 Hz), [0144]
  • 3.31(2H,t,J=6.2 Hz), 4.15(2H,t,J=6.2 Hz), [0145]
  • 4.96(2H,s), 7.18(1H,d,J=8.4 Hz), [0146]
  • 7.46(1H,d,J=8.4 Hz), 7.90(1H,s). [0147]
  • (13). N-(3-chloro-2,6-diethylphenyl)-2,3-quinoxaline-dicarboximide [0148]
  • [0149] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.11(3H,t,J=7.5 Hz), 1.16(3H,t,J=7.5 Hz), [0150]
  • 2.46(2H,q,J=7.5 Hz), 2.64(2H,q,J=7.5 Hz), [0151]
  • 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). [0152]
  • (14). N-(3-chloro-2-methylphenyl)-2,3-quinoxaline-dicarboximide [0153]
  • [0154] 1H-NMR [TMS/CDC3, δ (ppm)]
  • 2.29(3H,s), 7.24(1H,d,J=8.0 Hz), [0155]
  • 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). [0156]
  • (15). N-(3-chloro-2,6-diethylphenyl)-5-fluoro-2,3-quinolinedicarboximide [0157]
  • mp 116-118° C. [0158]
  • (16). N-(3-chloro-2,6-diethylphenyl)-6-fluoro-2,3-quinolinedicarboximide [0159]
  • [0160] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.09(3H,t,J=7.8 Hz), 1.14(3H,t,J=7.5 Hz), [0161]
  • 2.44(2H,q,J=7.5 Hz), 2.56-2.68(2H,m), [0162]
  • 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). [0163]
  • (17). N-(3-chloro-2,6-diethylphenyl)-7-fluoro-2,3-quinolinedicarboximide [0164]
  • [0165] 1H-NMR [TMS/CDCl3δ (ppm)]
  • 1.09(3H,t,J=7.8 Hz), 1.14(3H,t,J=7.5 Hz), [0166]
  • 2.44(2H,q,J=7.5 Hz), 2.56-2.68(2H,m), [0167]
  • 7.22(1H,d,J=8.1 Hz), 7.48(1H,d,J=8.1 Hz), [0168]
  • 7.63(1H,ddd,J=2.4, 8.1 and 9.3 Hz), [0169]
  • 8.12(1H,dd,J=2.4 and 9.6 Hz), 8.16(1H,dd,J=5.7 and [0170]
  • 9.3 Hz), 8.81(1H,s). [0171]
  • (18). N-(4-trifluoromethoxyphenyl)-7-fluoro-2,3-quinolinedicarboximide [0172]
  • mp 264-266° C. [0173]
  • (19). N-(4-trifluoromethoxyphenyl)-6-fluoro-2,3-quinolinedicarboximide [0174]
  • mp 287-289° C. [0175]
  • (20). N-(4-trifluoromethoxyphenyl)-5-fluoro-2,3-quinolinedicarboximide [0176]
  • [0177] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 7.39-7.43(2H,m), 7.51(1H,ddd,J=0.9, 7.8 and [0178]
  • 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), [0179]
  • 9.09(1H,d,J=0.9 Hz). [0180]
  • (21). N-(2-methyl-4-pentafluoroethylphenyl)-6-fluoro-2,3-quinolinedicarboximide [0181]
  • [0182] 1H-NMR [TMS/CDC3, δ (ppm)]
  • 2.33(3H,s), 7.43(1H,d,J=8.4 Hz), [0183]
  • 7.62(1H,d,J=8.4 Hz), 7.64(1H,s), 7.81-7.72(2H,m), [0184]
  • 8.50(1H,dd,J=5.4 and 9.0 Hz), 8.77(1H,s). [0185]
  • (22). N-(3-chloro-2,6-diethylphenyl)-5-chloro-2,3-quinolinedicarboximide [0186]
  • [0187] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.10(3H,t,J=7.5 Hz), 1.15(3H,t,J=7.5 Hz), [0188]
  • 2.45(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz), [0189]
  • 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), [0190]
  • 9.29(1H,s). [0191]
  • (23). N-(3-chloro-2,6-diethylphenyl)-6-chloro-2,3-quinolinedicarboximide [0192]
  • [0193] 1H-NMR [TMS/d6-DMSO, δ (ppm)]
  • 0.99(3H,t,J=7.5 Hz), 1.04(3H,t,J=7.5 Hz), [0194]
  • 2.40(2H,q,J=7.5 Hz), 2.60(2H,q,J=7.5 Hz), [0195]
  • 7.36(1H,d,J=8.5 Hz), 7.61(1H,d,J=8.5 Hz), [0196]
  • 8.09(1H,d,J=8.1 Hz), 8.40(1H,d,J=8.1 Hz), [0197]
  • 8.52(1H,s), 9.15(1H,s). [0198]
  • (24). N-(3-chloro-methylphenyl)-6-chloro-2,3-quinolinedicarboximide [0199]
  • [0200] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 2.27(3H,s), 7.20(1H,d,J=7.8 Hz), [0201]
  • 7.32(1H,t,J=7.8 Hz), 7.53(1H,d,J=7.8 Hz), [0202]
  • 7.93(1H,dd,J=2.0 and 8.0 Hz), 8.11(1H,d,J=2.0 Hz), [0203]
  • 8.42(1H,d,J=8.0 Hz), 8.71(1H,s). [0204]
  • (25). N-(3-chloro-2,6-diethylphenyl)-7-chloro-2,3-quinolinedicarboximide [0205]
  • [0206] 1H-NMR [TMS/d6-DMSO, δ (ppm)]
  • 0.99(3H,t,J=7.5 Hz), 1.04(3H,t,J=7.5 Hz), [0207]
  • 2.45(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz), [0208]
  • 7.37(1H,d,J=8.5 Hz), 7.62(1H,d,J=8.5 Hz), [0209]
  • 7.99(1H,dd,J=2.5 and 8.5 Hz), 8.43(1H,d,J=8.5 Hz), [0210]
  • 8.48(1H,d,J=2.5 Hz), 9.24(1H,s). [0211]
  • (26). N-(3-chloro-2,6-diethylphenyl)-5-methyl-2,3-quinolinedicarboximide [0212]
  • mp 178-180° C. [0213]
  • (27). N-(3-chloro-2,6-diethylphenyl)-6-methyl-2,3-quinolinedicarboximide [0214]
  • [0215] 1H-NMR [TMS/CDCl3δ (ppm)]
  • 1.10(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz), [0216]
  • 2.45(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz), [0217]
  • 2.65(3H,s), 7.21(1H,d,J=8.5 Hz), [0218]
  • 7.47(1H,d,J=8.5 Hz), 7.80(1H,d,J=8.0 Hz), [0219]
  • 7.88(1H,s), 8.37(1H,d,J=8.0 Hz), 8.71(1H,s). [0220]
  • (28). N-(3-chloro-2,6-diethylphenyl)-8-methyl-2,3-quinolinedicarboximide [0221]
  • [0222] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.00(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz), [0223]
  • 2.45(2H,q,J=7.5 Hz), 2.60(2H,q,J=7.5 Hz), [0224]
  • 2.95(3H,s), 7.20(1H,d,J=8.5 Hz), [0225]
  • 7.40(1H,d,J=8.5 Hz), 7.70(1H,t,J=8.0 Hz), [0226]
  • 7.95(1H,d,J=8.0 HZ), 8.75(1H,s). [0227]
  • (29). N-(3-chloro-2-methylphenyl)-6-methyl-2,3-quinolinedicarboximide [0228]
  • [0229] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 2.26(3H,s), 2.65(3H,s), 7.20(1H,d,J=8.5 Hz), [0230]
  • 7.30(1H,t,J=8.5 Hz), 7.51(1H,d,J=8.5 Hz), [0231]
  • 7.85(1H,d,J=8.0 Hz), 7.87(1H,s), [0232]
  • 8.35(1H,d,J=8.0 Hz), 8.69(1H,s). [0233]
  • (30). N-(3-chloro-2,6-diethylphenyl)-6-hydroxy-2,3-quinolinedicarboximide [0234]
  • [0235] 1H-NMR [TMS/CDCl3, 6 (ppm)]
  • 1.06(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz), [0236]
  • 2.45(2H,q,J=7.5 Hz), 2.65(2H,q,J=7.5 Hz), [0237]
  • 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), [0238]
  • 8.38(1H,d,J=8.5 Hz), 8.62(1H,s). [0239]
  • (31). N-(3-chloro-2,6-diethylphenyl)-6-methoxy-2,3-quinolinedicarboximide [0240]
  • [0241] 1H-NMR [TMS/d6-DMSO, δ (ppm)]
  • 1.10(3H,t,J=7.5 Hz), 1.18(3H,t,J=7.5 Hz), [0242]
  • 2.50(2H,q,J=7.5 Hz), 2.87(2H,q,J=7.5 Hz), [0243]
  • 3.95(1H,s), 7.21(1H,d,J=8.5 Hz), [0244]
  • 7.35(1H,d,J=8.5 Hz), 8.05(1H,d,J=8.0 Hz), [0245]
  • 8.86(1H,s), 9.24(1H,s), 10.28(1H,d,J=8.0 Hz). [0246]
  • (32). N-(3-chloro-2,6-diethylphenyl)-6,7-dimethoxy-2,3-quinolinedicarboximide [0247]
  • [0248] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.09(3H,t,J=7.8 Hz), 1.14(3H,t,J=7.8 Hz), [0249]
  • 2.45(2H,q,J=7.8 Hz), 2.63(2H,q,J=7.8 Hz), [0250]
  • 4.10(6H,s), 7.20(1H,d,J=8.5 Hz), 7.28(1H,s), [0251]
  • 7.45(1H,d,J=8.5 Hz), 7.76(1H,s), 8.58(1H,s). [0252]
  • (33). N-(3-chloro-2,6-diethylphenyl)-6,7-methylenedioxy-2,3-quinolinedicarboximide [0253]
  • [0254] 1H-NMR [TMS/CDCl3, δ (ppm)]
  • 1.09(3H,t,J=7.5 Hz), 1.15(3H,t,J=7.5 Hz), [0255]
  • 2.45(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz), [0256]
  • 6.27(2H,s), 7.20(1H,d,J=8.5 Hz), 7.32(1H,s), [0257]
  • 7.45(1H,d,J=8.5 Hz), 7.71(1H,s), 8.55(1H,s). [0258]
  • 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. [0259]
  • E. General Formula (III)→General Formula (I-1) [0260]
  • As the inert solvents usable in this reaction, the inert solvents exemplified in B and pyridines can be referred to. [0261]
  • 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. [0262]
  • 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. [0263]
  • 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. [0264]
  • The reaction time may vary with temperature and scale of the reaction, and it ranges from several minutes to 48 hours. [0265]
  • 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. [0266]
  • 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 [0267]
    Figure US20030073582A1-20030417-C00023
    Figure US20030073582A1-20030417-C00024
    TABLE 1
    Figure US20030073582A1-20030417-C00025
    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]
    TABLE 2
    Figure US20030073582A1-20030417-C00026
    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]
    TABLE 3
    Figure US20030073582A1-20030417-C00027
    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]
    TABLE 4
    Figure US20030073582A1-20030417-C00028
    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]
    TABLE 5
    Figure US20030073582A1-20030417-C00029
    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]
    TABLE 6
    Figure US20030073582A1-20030417-C00030
    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]
    TABLE 7
    Figure US20030073582A1-20030417-C00031
    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]
    TABLE 8
    Figure US20030073582A1-20030417-C00032
    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]
    TABLE 9
    Figure US20030073582A1-20030417-C00033
    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]
    TABLE 10
    Figure US20030073582A1-20030417-C00034
    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]
    TABLE 11
    Figure US20030073582A1-20030417-C00035
    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]
    TABLE 12
    Figure US20030073582A1-20030417-C00036
    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]
    TABLE 13
    Figure US20030073582A1-20030417-C00037
    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]
    TABLE 14
    Figure US20030073582A1-20030417-C00038
    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
  • 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 ([0281] 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.
  • 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. [0282]
  • 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. [0283]
  • 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. [0284]
  • 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. [0285]
  • 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. [0286]
  • 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. [0287]
  • 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. [0288]
  • 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. [0289]
  • 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. [0290]
  • 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. [0291]
  • To improve the flowability of a solid product, there may be used adjuvants such as waxes, stearates and alkyl phosphates. [0292]
  • Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products. [0293]
  • Adjuvants such as silicone oil may also be used as a defoaming agent. [0294]
  • 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. [0295]
  • 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. [0296]
  • 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. [0297]
  • 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.[0298]
    • EXAMPLES
  • Next, typical examples of the present invention and referential examples are presented below. The present invention is by no means limited by these examples. [0299]
    • Example 1
  • 1-1. Production of 3-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-7-fluoro-2-quinolinecarboxylic acid n-propylamide (Compound No. 158) [0300]
  • 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. [0301]
  • 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. [0302]
  • Property: m.p. 220-222° C.; Yield: 87% [0303]
  • 1-2. Production of 3-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-1,8-naphthylidine-2-carboxylic acid ethylamide (Compound No. 360) [0304]
  • 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. [0305]
  • 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. [0306]
  • Property: m.p. 249-264° C.; Yield: 80% [0307]
  • 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) [0308]
  • 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. [0309]
  • 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. [0310]
  • Property: m.p. 166-170° C.; Yield: 83% [0311]
    • Example 2
  • 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) [0312]
  • 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. [0313]
  • 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. [0314]
  • Property: m.p. 230-233° C.; Yield: 77% [0315]
  • 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) [0316]
  • 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. [0317]
  • 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. [0318]
  • Property: m.p. 198-200° C.; Yield: 84% [0319]
    • Referential Example 1 Production of 6-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[5,4-b]pyridine-5-carboxylic Acid
  • 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. [0320]
  • 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. [0321]
  • [0322] —H-NMR[TMS/CDCl3, δ (ppm)]
  • 1.21(3H,t,J=7.5 Hz), 1.26(3H,t,J=7.5 Hz), [0323]
  • 2.63(2H,q,J=7.5 Hz), 2.83(2H,q,J=7.5 Hz), [0324]
  • 4.27(3H,s), 7.18(1H,d,J=8.4 Hz), [0325]
  • 7.41(1H,d,J=8.4 Hz), 8.30(1H,s), 9.43(1H,s), [0326]
  • 10.10 (1H,bs) [0327]
    • Referential Example 2 Production of N-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[5,4-b]pyridine-5,6-carboximide
  • 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. [0328]
  • 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. [0329]
  • [0330] 1H-NMR(TMS/CDCl3, δ (ppm)]
  • 1.09(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz), [0331]
  • 2.43(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz), [0332]
  • 4.34(3H,s), 7.20(1H,d,J=8.4 Hz), [0333]
  • 7.47(1H,d,J=8.4 Hz), 8.35(1H,s), 8.67(1H,s) [0334]
    • Referential Example 3 Production of N-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[4,5-b]pyridine-5,6-carboximide
  • 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. [0335]
  • 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. [0336]
  • [0337] 1H-NMR[TMS/CDCl3δ (ppm)]
  • 1.08(3H,t,J=7.5 Hz), 1.12(3H,t,J=7.5 Hz), [0338]
  • 2.43(2H,q,J=7.5 Hz), 2.63(2H,q,J=7.5 Hz), [0339]
  • 4.27(3H,s), 7.20(1H,d,J=8.4 Hz), [0340]
  • 7.48(1H,d,J=8.4 Hz), 8.37(1H,s), 8.53(1H,s) [0341]
  • 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. [0342]
  • In the preparation examples, the term “part” means part by weight. [0343]
    • Preparation Example 1
  • [0344]
    Each compound listed in Tables 1 to 14 50 parts
    Xylene 40 parts
    Mixture of polyoxyethylene nonylphenyl 10 parts
    ether and calcium alkylbenzenesulfonate
  • An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution. [0345]
    • Preparation Example 2
  • [0346]
    Each compound listed in Tables 1 to 14  3 parts
    Clay powder 82 parts
    Diatomaceous earth powder 15 parts
  • A dust was prepared by mixing uniformly and grinding the above ingredients. [0347]
    • Preparation Example 3
  • [0348]
    Each compound listed in Tables 1 to 14  5 parts
    Mixed powder of bentonite and clay 90 parts
    Calcium ligninsulfonate  5 parts
  • 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. [0349]
    • Preparation Example 4
  • [0350]
    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
  • A wettable powder was prepared by mixing uniformly and grinding the above ingredients. [0351]
    • Test Example 1 Test for Herbicidal Effect on Paddy Field Weeds Before Emergence
  • Soil was filled into {fraction (1/10000)} are pots and brought into a state of paddy field, in which seeds of barnyard grass ([0352] 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.
  • 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: [0353]
  • 5—Weed-killing rate is 100%. [0354]
  • 4—Weed-killing rate is 90-99%. [0355]
  • 3—Weed-killing rate is 70-89%. [0356]
  • 2—Weed-killing rate is 40-69%. [0357]
  • 1—Weed-killing rate is 1-39%. [0358]
  • 0—Weed-killing rate is 0%. [0359]
  • The results are shown in Table 15. [0360]
    • Test Example 2 Test for Herbicidal Effect on Paddy Field Weeds after Emergence
  • Soil was filled into {fraction (1/10000)} are pots and brought into a state of paddy field, in which seeds of barnyard grass ([0361] 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.
  • 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. [0362]
  • The results are shown in Table 15. [0363]
    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
  • 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 ([0364] 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.
  • 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. [0365]
  • At the same time, phytotoxicity to soybean plant and wheat was investigated and judged according to the criterion mentioned below. [0366]
  • Criterion for judgment of phytotoxicity: [0367]
  • 5—Crop-killing rate is 100%. [0368]
  • 4—Crop-killing rate is 90-99%. [0369]
  • 3—Crop-killing rate is 70-89%. [0370]
  • 2—Crop-killing rate is 40-69%. [0371]
  • 1—Crop-killing rate is 1-39%. [0372]
  • 0—Crop-killing rate is 0-20% [0373]
  • (No Phytotoxicity). [0374]
  • The results are summarized in Table 16. [0375]
    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
  • 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. [0376]
  • 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. [0377]
  • Sample weeds, their leaf stages, and leaf stages of soybean plant and wheat were as follows: [0378]
    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
  • [0379]
    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 (5)

1. A fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) or a salt thereof:
Figure US20030073582A1-20030417-C00039
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
Figure US20030073582A1-20030417-C00040
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:
Figure US20030073582A1-20030417-C00041
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:
Figure US20030073582A1-20030417-C00042
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:
Figure US20030073582A1-20030417-C00043
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:
Figure US20030073582A1-20030417-C00044
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:
Figure US20030073582A1-20030417-C00045
wherein R9, Y, Z and m are as defined above;
Q6 is a group of the following formula:
Figure US20030073582A1-20030417-C00046
wherein R9, Y, Z and m are as defined above;
Q7 is a group of the following formula:
Figure US20030073582A1-20030417-C00047
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:
Figure US20030073582A1-20030417-C00048
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:
Figure US20030073582A1-20030417-C00049
wherein R14, Y and Z are as defined above;
Q10 is a group of the following formula:
Figure US20030073582A1-20030417-C00050
wherein R14, Y and Z are as defined above;
Q11 is a group of the following formula:
Figure US20030073582A1-20030417-C00051
wherein R Y and Z are as defined above;
Q12 is a group of the following formula:
Figure US20030073582A1-20030417-C00052
wherein R14, Y and Z are as defined above;
Q13 is a group of the following formula:
Figure US20030073582A1-20030417-C00053
wherein R14, Y and Z are as defined above; and
Q14 is a group of the following formula:
Figure US20030073582A1-20030417-C00054
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
Figure US20030073582A1-20030417-C00055
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:
Figure US20030073582A1-20030417-C00056
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:
Figure US20030073582A1-20030417-C00057
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:
Figure US20030073582A1-20030417-C00058
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:
Figure US20030073582A1-20030417-C00059
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:
Figure US20030073582A1-20030417-C00060
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:
Figure US20030073582A1-20030417-C00061
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:
Figure US20030073582A1-20030417-C00062
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:
Figure US20030073582A1-20030417-C00063
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:
Figure US20030073582A1-20030417-C00064
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:
Figure US20030073582A1-20030417-C00065
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:
Figure US20030073582A1-20030417-C00066
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:
Figure US20030073582A1-20030417-C00067
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:
Figure US20030073582A1-20030417-C00068
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:
Figure US20030073582A1-20030417-C00069
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
Figure US20030073582A1-20030417-C00070
represents Q1, Q2, Q3, Q4, Q5, Q7, Q8,or Q11, wherein:
Q1 is a group of the following formula:
Figure US20030073582A1-20030417-C00071
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:
Figure US20030073582A1-20030417-C00072
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:
Figure US20030073582A1-20030417-C00073
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:
Figure US20030073582A1-20030417-C00074
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:
Figure US20030073582A1-20030417-C00075
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:
Figure US20030073582A1-20030417-C00076
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:
Figure US20030073582A1-20030417-C00077
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:
Figure US20030073582A1-20030417-C00078
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.
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