WO1998030564A1 - Derives des sulfamides - Google Patents

Derives des sulfamides Download PDF

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Publication number
WO1998030564A1
WO1998030564A1 PCT/KR1998/000003 KR9800003W WO9830564A1 WO 1998030564 A1 WO1998030564 A1 WO 1998030564A1 KR 9800003 W KR9800003 W KR 9800003W WO 9830564 A1 WO9830564 A1 WO 9830564A1
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WO
WIPO (PCT)
Prior art keywords
group
γçö
halogen
mono
alkyl
Prior art date
Application number
PCT/KR1998/000003
Other languages
English (en)
Inventor
Dae Whang Kim
Hae Sung Chang
Young Kwan Ko
Jae Wook Ryu
Jae Chun Woo
Dong Whan Ku
Jin Seok Kim
Original Assignee
Korea Research Institute Of Chemical Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Korea Research Institute Of Chemical Technology filed Critical Korea Research Institute Of Chemical Technology
Priority to AU56808/98A priority Critical patent/AU5680898A/en
Priority to JP10530765A priority patent/JP2000510157A/ja
Publication of WO1998030564A1 publication Critical patent/WO1998030564A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • 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
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to novel sulfonamide derivatives or in particular to novel sulfonamide derivatives of the following formula (1), and their use and composition as agriculturally suitable herbicides.
  • R a represents hydrogen; halogen; oxycarbonyl substituent; aminocarbonyl substituent; C ⁇ ⁇ C ⁇ alkyl group; C ⁇ ⁇ C 3 mono- or polyhalloalkyl group; Ci ⁇ C 3 alkoxy group; G C mono- or polyhalloalkoxy group; nitro group; G ⁇ C 3 alkylthio group; C ⁇ —C 3 polyhalloalkylthio group; C ⁇ ⁇ C 3 alkylsulfonyl group; C ⁇ ⁇ C polyhalloalkylsulfonyl group; cyano group; carboxy group; C ⁇ ⁇ C 4 alkoxycarbonyl group; C 3 ⁇ C alkoxyalkoxycarbonyl group; aminosulfonyl group; formyl group; G ⁇ 0. alkylcarbonyl group; or C —C 3 mono- or polyhalloalkylcarbonyl group;
  • R b represents hydrogen; halogen; O ⁇ C 6 alkyl group; substituted Ci ⁇ C ⁇ halloalkyl group in which one to three substituents are halogen atoms; Ci — C ⁇ alkylcarbonyl group ; G ⁇ C 6 alkoxycarbonyl group; phenyl group; or phenoxy group;
  • R represents hydrogen; halogen; C ⁇ ⁇ C 6 alkyl group; C 3 -C fi cycloalkyl group; or Ci ⁇ C 3 halloalkyl group;
  • E represents N or CH;
  • X, Y and Z independently represent hydrogen; halogen; hydroxy group; carboxy group; G ⁇ G. alkyl group; G ⁇ C6 mono- or polyhalloalkyl group; Ci ⁇ C ⁇ alkoxy group; G ⁇ C ⁇ mono- or polyhalloalkoxy group; phenyl group; substituted phenyl group in which one to five substituents are selected from halogen, nitro group, G ⁇ C 3 alkyl group, and Ci ⁇ C 3 mono- or polyhalloalkyl group; or G ⁇ C 6 alkylthio group.
  • Y and Z may be combined together to form 3 ⁇ 7 membered rings, or combined with one or more hetero atoms selected from nitrogen, oxygen and sulfur to form 3 ⁇ 7 membered heterocycles.
  • the objective of the present invention is to provide novel sulfonamide derivatives having very prominent herbicidal activities toward rice and wheat and also possess a good selectivity for annual and perennial weeds.
  • Another objective of the present invention is to provide herbicidal compositions containing said derivatives as active ingredients.
  • the present invention is related to novel sulfonamide derivatives of the following formula (1).
  • R a , R b , R c , E, X, Y and Z are the same as defined the above formula (1), respectively.
  • R a is hydrogen, halogen, G ⁇ C ⁇ alkyl group, or G ⁇ C 3 mono- or polyhalloalkyl group
  • R b is hydrogen, halogen, G ⁇ C ⁇ alkyl group, substituted G — C ⁇ halloalkyl group in which one to three substituents are selected from halogen atoms, G ⁇ C 3 alkylcarbonyl group, or G ⁇ C ⁇ alkoxycarbonyl group
  • R c is hydrogen, halogen, G ⁇ C ⁇ alkyl group, or G ⁇ C 3 halloalkyl group
  • E is N or CH
  • X, Y and Z are independently selected from hydrogen, halogen, G ⁇ -C ⁇ alkyl group, G ⁇ C ⁇ mono- or polyhalloalkyl group, G ⁇ C ⁇ alkoxy group, or G ⁇ C ⁇ mono- or polyhallo alkoxy group.
  • the sulfonamide derivatives according to the present invention may be prepared by the following reaction schemes
  • reaction scheme 1 is a schematic diagram showing a process for preparing sulfonamide derivatives of the above formula (1) as a target product by means of reacting a compound of the formula (2) and a compound of the formula (3).
  • R a , R b , R c , E, X, Y and Z are the same as defined in the above formula (1), respectively.
  • R a , R b , R c , E, X, Y and Z are the same as defined in the above formula (1), respectively.
  • a process for preparing the sulfonamide derivatives of the above formula (1) according to the present invention is explained in more detail as set forth hereunder.
  • the compounds of the formula (2) is reacted with compounds of the formula (3) in the molar equivalence or excess to obtain sulfonamide derivatives of the above formula (1) as a target product.
  • Such reaction is carried out in an inert solvent such as acetonitrile, N,N- dimethylformamide, N-methyl-2-pyrrolidinone, or tetrahydrofuran. It is preferred to use a acetonitrile.
  • the reaction is carried out in the presence of base. Generally the base are used in one to five molar ratio compared with the compounds of the above formula (2).
  • the reaction temperature is kept at -78 °C ⁇ room temperature. It is heated if necessary.
  • the target compounds can be easily obtained by evaporation and then filter, or work-up, etc.
  • a pure compound may be obtained by extraction using nonaqueous organic solvent such as dichloromethane and purification.
  • the sulfonamide derivatives of the above formula (1) can be easily obtained by purification techniques such as recrystallization or chromatography.
  • R a , R b and R c are the same as defined in the above formula (1), respectively.
  • the quinolinecarbonyl chloride compounds of the above formula (4) may be easily prepared using carboxy compounds of the following formula (5). Further, the above carboxy compounds are prepared by known oxidation of the compounds of the following formula (6). Such oxidation of the methyl group is carried out by the method mentioned in US Patent No. 4,715,889, and explained as shown in the following scheme 4. [Scheme 4]
  • R a , R b and R c are the same as defined in the above formula (1), respectively.
  • R a , R b and R c are the same as defined in the above formula (1), respectively.
  • the compounds of the above formula (3) may be prepared by the method disclosed in literature [Zh. Org. Khim 26(10), 2191 -2198(1990); Chem. Lett 1996, (12), 1077-1078].
  • the compounds of the above formula (3) may be easily prepared by the prior art using the known compounds listed in GB Patent No. 1,424,359, US Patent Nos. 4,511,393, 4,632,696, 4,717,416 and 4,715,889 etc.
  • the sulfonamide derivatives according to the present invention are sufficiently tolerant on most broadleaf and grass crops such as rice, soybeans, cotton and wheat. Such derivatives may also be useful for pre-emergent control of grassy weeds in said crops.
  • the sulfonamide derivatives of the present invention may be applied for instance in the form of wettable powder, dust, granules, solutions, suspensions or emulsifiable concentrates etc.
  • either solid carrier or liquid carrier can be used.
  • liquid carrier water, toluene, xylene, petroleum eyher, oils, acetone, methyl ethyl ketone, cyclohexanone, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, methanol, ethanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol or glycerine etc.
  • water for a diluent of said concentrate.
  • talc talc
  • silica silica
  • chalk siliceous earth
  • lime calcium carbonate
  • bentonite cotton seed hulls
  • wheat powder soy powder
  • sawdust lignin etc.
  • Surfactants including cationic, anionic and nonionic surfactants, can be employed in the instance case.
  • the surfactants diethanolammonium raurylsulfate, alkyl arylsulfonate (such as calcium dodecylbenzenesulfonate), alkylphenol-alkylene oxide adduct, alcohol-alkylene oxide adduct, soaps, alkyl naphthalenesulfonate salt, sulfosuccinate salt, sorbitol ester tert-ammonium salt, polyethylene glycol ester or alkyl phosphate ester salt etc.
  • alkyl arylsulfonate such as calcium dodecylbenzenesulfonate
  • alkylphenol-alkylene oxide adduct such as calcium dodecylbenzenesulfonate
  • alcohol-alkylene oxide adduct such as soaps, alkyl naphthalenesulfonate salt
  • the herbicidal composition according to the present invention may be formulated with other herbicides, insecticides, fungicides, plant growth regulators or fertilizers.
  • the contents of the sulfonamide derivatives of the formula (1), while varying depending on the formulations, is usually from 0.001 to 98 wt%, preferably from 0.01 to 90 wt%.
  • compositions Prior to the use, the compositions are diluted with an inert carrier, such as water etc. Further, the compositions are applied by means of common techniques, such as sprayer, granulator etc.
  • the sulfonamide derivatives according to the present invention are highly active as pre-emergent or post-emergent herbicides or plant growth regulants. When applied in high concentration, said compounds become nonselective herbicide. On the other hand, when applied in low concentration, said compounds become a herbicide with crop selectivity.
  • the possible candidates for the application are corn, wheat, oat, rice, soybean, cotton, etc.
  • the compounds as represented by the above formula (1) under the present invention may have varying herbicidal activity, plant- selectivity, and control spectrum, depending on the type of substituents.
  • weed control under the present invention means suppression activity of the natural growth.
  • the activities herein vary depending on the type of a plant, environment, or application method.
  • the compounds represented by the above formula (1) under the present invention should be applied during the pre-germination stage or before the full-growth for the optimum result.
  • the application amount of the sulfonamide derivatives represented by the above formula(l) is from 0.01 to 10 kg/ha. High concentrates are used for non-selective activity where as low concentrates are used for the plant- selective activity.
  • the water phase was washed with ethyl ether, acidified to pH 3 with 5% hydrochloric acid, and then extracted three times with dichloromethane.
  • the separated organic layers were dried on MgS0 , filtered, and concentrated under reduced pressure.
  • the crude solid was recrystallized using mixture solvent of dimethyl sulfoxide and ethyl ether for crystallization to give 80 mg of the target compound, m.p. : 248 ⁇ 250 ° C
  • the target compound was prepared in the same procedure as described in the example 1, 8-amino-7-chloroquinoline in place of 8-amino-3,7- dichloroquinoline.
  • the target compound was prepared in the same procedure as described in the example 1, 8-amino-7-fluoroquinoline in place of 8-amino-3,7- dichloroquinoline.
  • the target compound was prepared in the same procedure as described in the example 1, 8-amino-7-fluoroquinoline in place of 8-amino-3,7- dichloroquinolihe.
  • EXAMPLE 6 Preparation of N-(7-fluoroquinolin-8-yl)-7-fluoro-5-ethoxy-l,2,4- triazolo [1 ,5-c] py rimidin-2-sulf onamide
  • the target compound was prepared in the same procedure as described in the example 5, 2-chlorosulfonyl-7-fluoro-5-ethoxy-l,2,4-triazolo[l,5- c]pyrimidine in place of 2-chlorosulfonyl-7-fluoro-5-methoxy-l,2,4- triazolo [1 ,5-c] py rimidine.
  • reaction mixture was basified with sodium hydroxide solution and then concentrated under reduced pressure.
  • residue solid was dried in vacuum and recrystallized using mixture solvent of ethyl ether and n-hexane to give 1.3 g of the target compound as a yellow solid.
  • the ingredients are thoroughly blended, hammer-milled until all the solids are essentially under 100 ⁇ , re-blended, sifted through a U.S.S. No. 50 sieve(0.3 mm opening) and packaged.
  • the ingredients are dissolved in the solvent and the solution is sprayed upon de-dusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
  • the ingredients are blended and ground together in a sand mill to produce particles essentially under 5 n.
  • the ingredients are dissolved in water with stirring to produce the solution, which may then be packaged for use.
  • the ingredients are thoroughly blended, passed through an air mill, in order to produce an average particle size under 15 fln, re-blended, sifted through a U.S.S. No. 50 sieve(0.3 mm opening) and packaged.
  • Potassium sulfate 16 wt% The ingredients are blended in a rotating mixer, and water sprayed on to accomplish granulation. When most of the material has reached the target range of from 1.0 to 0.42 cm(U.S.S. No. 18 ⁇ 40 sieve), the granules are removed, dried, and screened. Oversized material is additionally crushed to the target range.
  • TEST 1 Pre-emergence test To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with 5 parts by weight of acetone, 1 part by weight of alkylaryl polyglycol ether as emulsifier was added and the solution diluted with water to the desired concentration. Seeds of the test plants are shown in normal soil and, after 24 hours, watered with the preparation of the active compound.
  • Test plants which had a height of 5 ⁇ 15 cm were sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area.
  • the concentration of i o the spray liquid was so chosen that the particular amounts of active compound desired were applied in 2,000 / of water/ ha.
  • the degree of damage to the plants was rated in % damage in comparison to the development of the untreated control.
  • the figures denote : 15 0% : no action(like untreated control) 20% : slight effect 70% : herbicidal effect 100% : total destruction
  • the active compounds(l) according to the preparation 0 examples exhibited a better herbicidal activity against mono- and dicotyledon weeds.
  • a plastic pot having a surface of 60 cm 2 or 140 cm 2 was filled with a small 5 amount of fertilizer, after then, the sterilized paddy soil of puddled state at the depth of 5 cm.
  • the pot was watered for a day at the depth of 2 cm and the manufactured herbicide was spot-treated on the plant in manner similar to the field condition(4 mg/pot).
  • herbicidal effect was measured by the same survey standard as that for field condition.
  • Table 1 represents pre- and post-emergence herbicidal effect of active ingredients of the present invention.
  • the plant species employed in these tests were selected from the following :

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouveaux dérivés des sulfamides, notamment de nouveaux sulfamides de formule générale (1), dans laquelle R?a, Rb, Rc¿, E, X, Y et Z sont identiques et tels que définis dans la description détaillée de la présente invention; ainsi que leur utilisation comme herbicides pour l'agriculture et une composition les contenant.
PCT/KR1998/000003 1997-01-11 1998-01-10 Derives des sulfamides WO1998030564A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU56808/98A AU5680898A (en) 1997-01-11 1998-01-10 Sulfonamide derivatives
JP10530765A JP2000510157A (ja) 1997-01-11 1998-01-10 スルフォンアミド誘導体

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR19970000557 1997-01-11
KR1997/557 1997-01-11

Publications (1)

Publication Number Publication Date
WO1998030564A1 true WO1998030564A1 (fr) 1998-07-16

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PCT/KR1998/000003 WO1998030564A1 (fr) 1997-01-11 1998-01-10 Derives des sulfamides

Country Status (5)

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JP (1) JP2000510157A (fr)
KR (1) KR100267506B1 (fr)
CN (1) CN1243514A (fr)
AU (1) AU5680898A (fr)
WO (1) WO1998030564A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100295819B1 (ko) * 1998-09-29 2001-09-22 김충섭 신규한 퀴놀린 설포늄염 유도체
US8299056B2 (en) 2008-09-08 2012-10-30 Signal Pharmaceuticals, Llc Aminotriazolopyridines, compositions thereof, and methods of treatment therewith

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5201938A (en) * 1991-07-19 1993-04-13 Dowelanco N-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides
US5447905A (en) * 1994-07-11 1995-09-05 Dowelanco N-indazolyl[1,2,4]triazolo[1,5-C]pyrimidine-2-sulfonamide herbicides
US5461161A (en) * 1994-07-11 1995-10-24 Dowelanco N-pyridinyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides
WO1996001828A1 (fr) * 1994-07-11 1996-01-25 Dowelanco Herbicides au n-pyridimyl [1,2,4] triazolo [1,5-c] pyrimidine-2-sulfonamide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5201938A (en) * 1991-07-19 1993-04-13 Dowelanco N-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides
US5447905A (en) * 1994-07-11 1995-09-05 Dowelanco N-indazolyl[1,2,4]triazolo[1,5-C]pyrimidine-2-sulfonamide herbicides
US5461161A (en) * 1994-07-11 1995-10-24 Dowelanco N-pyridinyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides
WO1996001828A1 (fr) * 1994-07-11 1996-01-25 Dowelanco Herbicides au n-pyridimyl [1,2,4] triazolo [1,5-c] pyrimidine-2-sulfonamide

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE WPIL ON QUESTEL, Week 9310, London: Derwent Publications Ltd., AN 93-076871, Class A01N; & US,A,5 201 938 (DOWELANCO). *
DATABASE WPIL ON QUESTEL, Week 9541, London: Derwent Publications Ltd., AN 95-319903, Class A01N; & US,A,5 447 905 (DOWELANCO). *
DATABASE WPIL ON QUESTEL, Week 9549, London: Derwent Publications Ltd., AN 95-381900, Class A01N; & US,A,5 461 161 (DOWELANCO). *
DATABASE WPIL ON QUESTEL, Week 9610, London: Derwent Publications Ltd., AN 96-097576, Class A01N; & WO,A,96 01828 (DOWELANCO). *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100295819B1 (ko) * 1998-09-29 2001-09-22 김충섭 신규한 퀴놀린 설포늄염 유도체
US8299056B2 (en) 2008-09-08 2012-10-30 Signal Pharmaceuticals, Llc Aminotriazolopyridines, compositions thereof, and methods of treatment therewith

Also Published As

Publication number Publication date
AU5680898A (en) 1998-08-03
JP2000510157A (ja) 2000-08-08
KR19980070447A (ko) 1998-10-26
CN1243514A (zh) 2000-02-02
KR100267506B1 (ko) 2000-11-01

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