| 摘要 |
<p>#CMT# #/CMT# Use of dithiin-tetracarboximide compounds (I) and dithiin-diisoimide compounds (V) for treating phytopathogenic fungi, is claimed. #CMT# : #/CMT# Use of dithiin-tetracarboximide compounds of formula (I) and dithiin-diisoimide compounds of formula (V) for treating phytopathogenic fungi, is claimed. R 1>, R 2> : H, 1-8C-alkyl (optionally substituted by halo, OR 3> or COR 4>), 3-7C-cycloalkyl (optionally substituted by halo, 1-4C-alkyl or 1-4C-haloalkyl), aryl (optionally substituted by halo, 1-4C-alkyl, 1-4C-haloalkyl, COR 4> or sulfonylamino) or aryl-(1-4C-alkyl); R 3> : H, 1-4C-alkyl, 1-4C-alkyl carbonyl or aryl (optionally substituted by halo, 1-4C-alkyl or 1-4C-haloalkyl); R 4> : OH, 1-4C-alkyl or 1-4C-alkoxy; and n : 0 or 1. Independent claims are included for: (1) an agent for combating phytopathogenic fungi comprising (I), diluents and/or surface active materials; (2) the dithiin-tetracarboximide compounds of formula (Ic); and (3) the dithiin-diisoimide compounds of formula (Va). R1a, R2a : 1-8C-alkyl substituted by F, OR3a or COR4a, 3-7C-cycloalkyl substituted by halo, 1-4C-alkyl or 1-4C-haloalkyl, or aryl-(1-4C-alkyl) substituted by COR4a in alkyl portion, preferably 1-4C-alkyl (optionally substituted by F, OH, CH 3O, C 2H 5O, methylcarbonyloxy, or carboxyl), 3-7C-cycloalkyl (optionally substituted by Cl, CH 3 or CF 3), 1-phenethyl or 2-phenethyl; R3a : 1-4C-alkyl, 1-4C-alkylcarbonyl or aryl (optionally substituted by halo, 1-4C-alkyl or 1-4C-haloalkyl), preferably CH 3, methylcarbonyl or phenyl; R4a : OH, 1-4C-alkyl or 1-4C-alkoxy, preferably OH or CH 3O; and r : 0 (preferred) or 1. Where R1a and R2a are not simultaneously acetoxymethyl (preferred) or methoxymethyl. #CMT#[Image]#/CMT# #CMT#[Image]#/CMT# #CMT#ACTIVITY : #/CMT# Fungicide; Nematocide; Anthelmintic; Insecticide; Acaricide; Antibacterial; Virucide. #CMT#MECHANISM OF ACTION : #/CMT# None given. #CMT#USE : #/CMT# (I) are useful for treating phytopathogenic fungi (claimed) in crop protection, household, hygienic sectors, material protections, greenhouse, forests or horticulture. (I) are useful as: an anthelmintic agent against internal parasites of animals, preferably nematodes; insecticide; and a pigment in electrophotographic photoreceptors, lacquers and polymers. (I) are useful to treat seeds of e.g. wheat, barley, rye, maize, and cotton. (I) are useful to combat mites, bacteria and viruses. The ability of (I) to combat Phytophthora infestans was tested. The results showed that 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetrone at a concentration of 250 ppm exhibited an efficiency of >= 70%. #CMT#ADVANTAGE : #/CMT# (I) exhibit good plant compatibility, and favorable warm-blood toxicity. (I) provides crops with high yields, improve quality, high growth, increased tolerance to high or low temperatures, increased tolerance to dry, water or soil salinity, increased flowering, high nutritional value, high sugar content in fruits, and increased germination. #CMT#ORGANIC CHEMISTRY : #/CMT# Preparation (Disclosed): Preparation of (I) comprises reacting dichloromaleic acid anhydride compound of formula (VI) with an amine compound of formula (R-NH 2) (III) optionally in the presence of a diluent to obtain maleic acid imide compound of formula (VII), subsequently reacting (VII) with a sulfur source (e.g. thiourea or hydrogen sulfide) to obtain dithiin-tetracarboximide compound of formula (Ib) and subsequently oxidizing (Ib) with nitric acid. R : R 1>. #CMT#[Image]#/CMT# #CMT#[Image]#/CMT# #CMT#DEFINITIONS : #/CMT# Preferred Definitions: R 1>, R 2> : H, 1-4C-alkyl (optionally substituted by F, Cl, OH, CH 3O, C 2H 5O, methylcarbonyloxy, or carboxyl), 3-7C-cycloalkyl (optionally substituted by Cl, CH 3 or CF 3), phenyl (optionally substituted by F, Cl, Br, CH 3, CF 3, COR 4> or sulfonylamino), benzyl, 1-phenethyl, 2-phenethyl or 2-methyl-2-phenethyl; R 3> : H, CH 3, methylcarbonyl or phenyl; R 4> : H or CH 3O; and n : 0 or 1. #CMT#ADMINISTRATION : #/CMT# Application of (I) (in the treatment of plant part) is 0.1-10000 (preferably 50-300) g/hectare. Application of (I) (in the seed treatment) is 2-200 (preferably 2.5-12.5) g/kg of seeds. Application of (I) (in the soil treatment) is 0.1-10000 (preferably 1-5000) g/hectare. Application of (I) is spraying, sprinkling, vaporization, atomizing, spreading, foaming, coating or drip irrigation. #CMT#SPECIFIC COMPOUNDS : #/CMT# 41 Compounds (I) are disclosed e.g. 2,6-bis[1-(trifluoromethyl)cyclopropyl]-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetrone of formula (Ia), 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetrone, 2,6-diethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetrone, 2,6-dipropyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetrone and 2,6-di(propan-2-yl)-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetrone. #CMT#[Image]#/CMT# #CMT#EXAMPLE : #/CMT# 1-(Trifluoromethyl)cyclopropylamine (800.7 mg) and diisopropylethylamine (0.85 ml) were added to a solution of succinic-acid anhydride (496 mg) in dioxane (10 ml) under ice cooling (10[deg] C) and stirred for 20 minutes. The mixture was again stirred at 80[deg] C for 20 minutes and cooled. The obtained solution was washed with acetic acid ethyl ester and water. The organic phases were dried and concentrated to obtain 4-oxo-4-{[1-(trifluoromethyl)cyclopropyl]amino}butanoic acid (815.8 mg). Thionylchloride (7.57 ml) was added to a solution of 4-oxo-4-{[1-(trifluoromethyl)cyclopropyl]amino}butanoic acid (0.8 g) in dioxane (2 ml) under ice cooling at (15[deg] C). The obtained mixture was heated over night. The residue was poured on ice, extracted, dried and concentrated with acetic acid ethyl ester to obtain 2,6-bis[1-(trifluoromethyl)cyclopropyl]-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetrone (284 mg).</p> |
