PL140272B1 - Herbicide and method of manufacture of novel derivatives of chloroacetamide - Google Patents
Herbicide and method of manufacture of novel derivatives of chloroacetamide Download PDFInfo
- Publication number
- PL140272B1 PL140272B1 PL83240481A PL24048183A PL140272B1 PL 140272 B1 PL140272 B1 PL 140272B1 PL 83240481 A PL83240481 A PL 83240481A PL 24048183 A PL24048183 A PL 24048183A PL 140272 B1 PL140272 B1 PL 140272B1
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- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 title claims description 5
- 239000004009 herbicide Substances 0.000 title claims description 5
- 230000002363 herbicidal effect Effects 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 C1-3-alkyl radical Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 8
- 239000003085 diluting agent Substances 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 238000007126 N-alkylation reaction Methods 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- A01N43/10—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 with sulfur as the ring hetero atom
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- 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
- A01N43/24—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 two or more hetero atoms
- A01N43/26—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 two or more hetero atoms five-membered rings
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- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
- A01N43/74—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 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- 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
- A01N43/74—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 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- 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
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- 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
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- 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
- A01N43/82—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 three ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/14—Nitrogen atoms
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- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/66—Nitrogen atoms
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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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)
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- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Przedmiotem wynalazku jest srodek chwastobójczy i sposób wytwarzania nowych pochod¬ nych chloroacetamidu stanowiacych substancje czynna. Nowe zwiazki przedstawione sa wzo¬ rem 1, w którym Ar oznacza grupe tiofenu lub izotiazolu zwiazana poprzez pierscieniowy atom wegla z atomem azotu grupy N/Y/COCJ^Cl, z która jest polaczona, przy czym grupa Ar moze byc niepodstawiona lub podstawiona jednym lub kilkoma podstawnikami, takimi jak atomy chlorowca, np. fluor, chlor i brom; rodniki C1-Zf-alkilowe, grupy Cg^-alkanoilowe, grupy C/«NOC1-Zf-alkilo/-C1^-alkilowe, C/O-C^-alkilo^-O, ,-alkilowe, 0,^-alkil-S, C1-Zf-alkil-S0, C^-alkoksy-karbonylowe i/lub grupy C^-alkoksylowe, Y oznacza grupe weglowodorowa, taka jak rodnik C^g-alkilowy, C^g-alkenylowy, C, 8-alkinylowy, przy czym taka grupa weglowodorowa jest niepodstawiona lub podstawiona chlorowcem, takim jak fluor, chlor lub brom, albo oznacza grupe Ctl/R^/-CQY^9 w której R-| oznacza atom wodoru lub rodnik C^-alkilowy, a Y1 oznacza grupe C^-alkoksylowa, CL^-alkinyloksylowa, C^-alkiloaminowa dwu-ZC^-alkiloZ-aminowa lub grupe NH-N«C/C1 ,-alkilowa/2, albo ozna¬ cza grupe R^-Az, w której R2 oznacza grupe CK2 lub CH2-CH2 niepodstawiona lub podstawio¬ na rodnikiem C^c-alkilowym, a Az oznacza aromatyczny pierscien heterocykliczny, taki Jak diazol lub triazol, zwiazany poprzez jeden ze swych atomów azotu z TU, 5-czlonowy pier¬ scien heterocykliczny zwiazany poprzez pierscieniowy atom wegla z R^ i posiadajacy 1-3 heteroatomy, takie jak tlen, siarka lub azot, albo grupa pirymidylowa, albo Y oznacza grupe A-O-R*, w której R, oznacza atom wodoru lub rodnik Cj o-alkilowy, niepodstawiony lub podstawiony chlorowcem, grupa cyjanowa lub alkoksylowa, C1 «-alkilenowa niepodsta¬ wiona albo podstawiona grupa C^-alkoksylowa, przy czym A moze byc polaczone z R, two¬ rzac nasycony, zawierajacy tlen pierscien heterocykliczny zawierajacy 1 lub 2 atomy tle¬ nu jako heteroatomy, przy czym atomy azotu i tlenu, które sa zwiazane z A, rozdzielone sa przez 1 lub 2 atomy wegla, albo Y oznacza grupe o wzorze 2, w którym R^ oznacza rod¬ nik C^-alkiIowy, a FL i Re' niezaleznie od siebie oznaczaja wodór lub rodnik metylowy.2 140 272 Jako ewentualne podstawniki Ar nie wystepujace w pozycji orto w stosunku do N-pod- stawionej grupy chloroacetyloaminowej wymienia sie korzystnie rodniki C^^-alkilowe, np. rodnik metylowy, atomy chlorowca, np. chloru, bromu, oraz grupy C^-alkoksykarbo- nylowe, np. COOCH*. N-podstawiona grupa chioroacetyloaminowa jest korzystnie zwiazana z pierscieniowym atomem wegla w pozycjip w stosunku do heteroatomów w pierscieniu, tak wiec w pozycji 3, gdy Ar stanowi tiofen i w pozycji 4, gdy Ar oznacza izotiazol. Korzy¬ stna podgrupa tej ostatniej grupy sa zwiazki, w których grupa Ar jest podstawiona w po¬ zycji orto, zwlaszcza w pozycji orto-orto w stosunku do N-podstawionej grupy acetyloami- nowej, szczególnie gdy podstawniki sa wybrane z grupy wyzej podanej. Atom azotu w pier¬ scieniu moze byc niepodstawiony lub podstawiony. Jezeli jest podstawiony, to korzystnie jest podstawiony rodnikiem C^^-alkilowym, zwlaszcza metylowym lub etylowym. Szczególnie korzystna podgrupa zwiazków o wzorze 1 sa zwiazki, w których Ar stanowi tiofen, zwlasz¬ cza zas oznacza grupe 3-tienylowa co najmniej 2,4-dwupodstawiona, a zwlaszcza zwiazki 3-tienylowe, w których podstawniki w pozycji 2 i 4 stanowia rodniki C^^-alkilowe i gru¬ py C^^-alkoksylowe.W przypadku, gdy Y, R*, R^ oznaczaja grupy weglowodorowe podstawione chlorowcem, ta¬ kim chlorowcem korzystnie jest chlor lub brom, tak podstawiona grupa weglowodorowa Jest korzystnie monopodstawiona. Jezeli Y oznacza grupe weglowodorowa podstawiona chlorowcem, to chlorowiec na ogól korzystnie nie wystepuje w pozycji 1, o ile przewidziane jest sto¬ sowanie tego zwiazku jako herbicydu (takie 1-chlorowcowane zwiazki sa na ogól nietrwale, stanowia one jednak cenne produkty posrednie do produkcji innych zwiazków o wzorze 1, np. takich, w których Y oznacza grupe alkoksyalkilowa lub pirazolilometylowa); korzyst¬ nym przykladem takiego znaczenia Y jest grupa 2-chloroetylowa.W przypadku, gdy Y, R,, R^ oznaczaja rodniki C|_Q-alkilowe, C«_8-alkenylowe lub C^g-alkinylowe, zawieraja one korzystnie do 5 atomów wegla. W przypadku, gdy R1 oznacza rodnik C1-5-alkilowy, jest to korzystnie rodnik metylowy lub etylowy, zwlaszcza metylo¬ wy. W przypadku, gdy R2 oznacza grupe CH2, moze ona byó podstawiona przez 1 lub 2, ko¬ rzystnie przez 1 rodnik C^ --alkilowy. W przypadku, gdy R^ oznacza grupe CH2CH2» m PL PL PL
Claims (10)
1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych chloroacetamidu o wzorze 1, w którym Ar ozna¬ cza grupe tiofenu lub izotiazolu zwiazana poprzez pierscieniowy atom wegla z atomem azotu grupy N/Y/COCHpCl, z która jest polaczona, przy czym grupa Ar moze byc niepodstawiona lub podstawiona przez jeden lub wiecej podstawników, takich jak atomy chlorowca, np. fluoru, chloru i bromu, grupy C^-alkilowe, Cp_^-alkanoilowe, C/«N0Cj_/+-alkilo/-C] ,-alkilowe, C/OC^-alkilo^-C^,-alkilowe, C^-alkil-S, C1-B^-alkil-S0, C^-alkoksykarbonylowe i/lub C^-alkoksylowe, Y oznacza grupe weglowodorowa, taka jak rodnik C^g-alkilowy, CL g-alkenylowy, CL g-alkinylowy, przy czym taka grupa weglowodorowa jest niepodstawiona albo podstawiona chlorowcem, takim jak fluor, chlor lub brom, albo oznacza grupe CH/R^/-C0Y^f w której R,, oznacza atom wodoru lub rodnik C| --alkilowy, a Y^ oznacza grupe C1 c-alkoksylowaf C, c-alkinyloksylowa, C^-alkiloaminowa, dwu/C^-alkiW-aminowa, NH-N-C/Oj ,-alkilowa/2 albo Y oznacza grupe R2-Az, w której R2 oznacza rodnik CH2 lub CH2-CH2 niepodstawiony lub podstawiony rodnikiem ^ e-alkilowym, a Az oznacza aromatyczny pierscien heterocykliczny, taki jak diazol lub triazol zwiazany z Rp poprzez jeden ze swych atomów azotu, 5-czlonowy pierscien heterocykliczny zwiazany z Rp poprzez pierscieniowy atom wegla i zawierajacy 1-3 heteroatomy, takie jak tlen, siarka lub azot, albo grupe pirymidylowa, albo Y oznacza grup^ A-O-Rz* w której R, oznacza atom wodoru albo rodnik Cj ^-alkilowy niepodstawiony lub podstawiony chlorowcem, grupa cyjanowa lub alkoksylowa, a A oznacza grupe C^ o-alkilenowa niepodstawiona albo podstawiona grupa ^ .-alkoksylowa, przy czym A moze byc zwiazane z R, tworzac nasycony, zawierajacy tlen pierscien heterocykliczny zawierajacy 1 lub 2 atomy tlenu jako heteroatomy, przy czym atomy azotu i tlenu, które sa polaczone z A sa rozdzielone 1 lub 2 atomami wegla, albo oznacza grupe o wzorze 2, w której R^ oznacza ro¬ dnik C* --alkilowy, a Re i RJ niezaleznie od siebie oznaczaja atom wodoru lub rodnik me¬ tylowy, znamienny tym, ze zwiazek o wzorze 3, w którym Ar ma znaczenie wy¬ zej podane, poddaje sie reakcji ze zwiazkiem o wzorze kf w którym Y ma znaczenie wyzej po¬ dane, a L oznacza grupe odszczepialna zdolna do odszczepienia w warunkach reakcji N-alki- lowania.
2. srodek chwastobójczy zawierajacy substancje czynna i dopuszczalny w srodkach chwa¬ stobójczych rozcienczalnik, znamienny tym, ze- jako substancje czynna zawie¬ ra nowe pochodne chloroacetamidu o wzorze 1, w którym Ar oznacza grupe tiofenu lub izo¬ tiazolu zwiazana poprzez pierscieniowy atom wegla z atomem azotu grupy N/Y/C0CH2C1, z któ¬ ra jest polaczona, przy czym grupa Ar moze byc niepodstawiona lub podstawiona przez jeden lub wiecej podstawników, takich jak atomy chlorowca, np. fluoru, chloru i bromu, grupy10 1^0 272 C^-alkilowe, C2_^-alkanoilowe, CZ-NOC^-alkilo/Cj^-alkilowe, C/OC^-alkilo/^-C^- -alkilowe, G^-alkil-S, C^^-alkil-SO, C^-alkoksykarbonylowe i/lub C^-alkoksylowe, Y oznacza grupe weglowodorowa, taka jak rodnik C^g-alkilowy, C* Q-alkenylowy, Cj_Q-alki- nylowy, przy czym taka grupa weglowodorowa jest niepodstawiona albo podstawiona chlorow¬ cem, takim jak fluor, chlor lub brom, albo oznacza grupe CH/R-j/-C0Y1f w której Hj oznacza atom wodoru lub rodnik C^ c-alkilowy, a Y1 oznacza grupe C^ --alkoksylowa, C» c-alkinylo- ksylowa, a^-alkiloaminowa, dwu-Zc^^-alkil ©/-aminowa, NH-NsC/C^,-alkilowa^, albo Y oznacza grupe F^-Az, w której F^ oznacza rodnik CH2 lub CH2-CH2 niePocistawioRy lub pod¬ stawiony rodnikiem C^ ^-alkilowym, a Az oznacza aromatyczny pierscien heterocykliczny, taki jak diazol lub triazol zwiazany z .^ poprzez jeden ze swych atomów azotu, 5-czlono- wy pierscien heterocykliczny zwiazany z R^ poprzez pierscieniowy atom wegla i zawieraja¬ cy 1-3 heteroatomy, takie jak tlen, siarka lub azot, albo grupe pirymidylowa albo Y ozna¬ cza grupe A-O-R*, w której R- oznacza atom wodoru albo rodnik Cj o-alkilowy niepodstawio- ny lub podstawiony chlorowcem, grupa cyjanowa lub alkoksylowa, a A oznacza grupe C^g-al- Jcil*nowa niepodstawiona albo podstawiona grupa Gj c-alkoksylowa, przy czym A moze byc zwiazane z R» tworzac nasycony, zawierajacy tlen pierscien heterocykliczny zawierajacy 1 lub 2 atomy tlenu jako heteroatomy, przy czym atomy azotu i tlenu, które sa polaczone z A, sa rozdzielone 1 lub 2 atomami wegla, albo oznacza grupe o wzorze 2, w której R^ oznacza rodnik ^ =-alkilowy, a FU i Rj niezaleznie od siebie oznaczaja atom wodoru lub rodnik metylowy,
3. Srodek wedlug zastrz. 2, znamienny tym, ze zawiera zwiazek o wzo¬ rze 1, w którym Ar jest co najmniej dwupodstawiony w pozycji o, o'do grupy chioroaceta¬ midowej podstawnikami okreslonymi w zastrz. 1, a ewentualny dodatkowy podstawnik tego pierscienia heteroaromatycznego wybrany jest z grupy obejmujacej rodnik C^^-alkilowy, chlorowiec i grupe C^^-alkoksykarbonylowa.
4. srodek wedlug zastrz. 2, znamienny tym, ze zawiera zwiazki o wzo¬ rze 1, w którym Rp oznacza CK2 lub CH/CH*/, Az oznacza grupe 1-pirazolilowa lub 3,5^-dwu- metylo-1-pirazolilcwa, A oznacza CH2, CH2-CH2 lub ich monometylowana pochodna, a R, oznacza rodnik C^-alkilowy.
5. srodek wedlug zastrz. U9 znamienny tym, ze zawiera zwiazek o wzorze 1, w którym Ar oznacza grupe 3-tienylowa, 2,k-dwup odstawiona podstawnikami takimi, jak grupa Cj^-alkilowa i C^-alkoksylc^a.
6. Srodek wedlug zastrz. 59 znamienny tym, ze zawiera zwiazek o //zorze 1, w który™ Ar i Y maja odpowiednio nastepujace znaczenia: a/ 2,^-dwumetylc-3-yl i pira- zolilo-1-metyl, b/ 2,k-dwun:etylo-ti?n-3-yl i 1-/pirazolilc-1/-etyl, 0/ 2,4-dwumetylo¬ wi en-3-yl i CHgOCgH^,. d/ 2,4-dvunetylc-tien-3-yl i C^OC^n, e/ 2-n:etylo-4-etylc-tier.- -3-y1 i CHgOCgKct £/ 2-metylc-^-metoksy-tien-3-yl i pirazolilo-i-metyl i g/ 2-metylo-^- -metoksy-tien-3-yl i CH2CH20C2K5 *
7. srodek wedlug zastrz. 5, znamienny tym, ze zawiera zwiazek o wzorze 1, w którym Ar oznacza grupe 2,4-dwumetylo-tien-3-ylowa, a Y oznacza grupe CH/CH»/CH20CH,.
8. srodek wedlug zastrz. 2, znamienny tym, ze zawiera 0,01-99 % wago¬ wych substancji czynnej, 0-20 % wagowych dopuszczalnego w srodkach chwastobójczych srod¬ ka powierzchniowo czynnego i 1-99,99 % wagowych dopuszczalnego w srodkach chwastobój¬ czych rozcienczalnika lub rozcienczalników.
9. » srodek wedlug zastrz. 8, znamienny tym, ze zawiera 10-80 % wagowych substancji czynnej.
10. Srodek wedlug zastrz. 8, znamienny tym, ze zawiera 0,01 - 25 % wa¬ gowych substancji czynnej.140 272 Ar N- WZÓR 1 C0CH2CI ¦Y CH — C = NORA R5 Ri WZdR2 Ar NH COCH2Cl WZ0R3 LY WZÓR 4 /N=l CH(CH3) N 1 WZÓR 5 CH, Ti N O—Me ¦S* WZÓR 6 N N CH, Ji "0 WZÓR 7 Et N— CH2 l^N •Me WZÓR 8 N N S' CH2 VcJ Me WZÓR 9140 272 N N J Ji CH- H WZÓR 10 N N ¦Me SMe Me WZÓR 11 CH 2 i / WZÓR 12 CH^ O j WZÓR 13 Pracownia Poligraficzna UF PRL. Naklad 100 egz. Cena 130 zl PL PL PL PL
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GB8203636 | 1982-02-09 | ||
GB8226006 | 1982-09-13 |
Publications (2)
Publication Number | Publication Date |
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PL240481A1 PL240481A1 (en) | 1984-10-08 |
PL140272B1 true PL140272B1 (en) | 1987-04-30 |
Family
ID=26281932
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL83240481A PL140272B1 (en) | 1982-02-09 | 1983-02-08 | Herbicide and method of manufacture of novel derivatives of chloroacetamide |
Country Status (22)
Country | Link |
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JP (1) | JPH0645617B2 (pl) |
KR (1) | KR880002359B1 (pl) |
AU (1) | AU566009B2 (pl) |
BG (1) | BG60498B2 (pl) |
BR (1) | BR8300630A (pl) |
CA (1) | CA1248538A (pl) |
CH (1) | CH655312A5 (pl) |
CZ (1) | CZ278361B6 (pl) |
DE (1) | DE3303388C2 (pl) |
DK (2) | DK53583A (pl) |
EG (1) | EG16720A (pl) |
ES (1) | ES519588A0 (pl) |
FR (2) | FR2530631B1 (pl) |
HU (1) | HU193036B (pl) |
IE (1) | IE55108B1 (pl) |
IL (1) | IL67852A (pl) |
IT (1) | IT1163085B (pl) |
MY (1) | MY8700168A (pl) |
NL (2) | NL190919C (pl) |
PL (1) | PL140272B1 (pl) |
SK (1) | SK86783A3 (pl) |
TR (1) | TR21805A (pl) |
Families Citing this family (7)
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DE59408196D1 (de) * | 1993-03-22 | 1999-06-10 | Novartis Ag | Selektiv-herbizides Mittel |
EP2052606A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
DE102008037620A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
EA025009B1 (ru) | 2010-10-15 | 2016-11-30 | Байер Интеллектуэль Проперти Гмбх | Применение als ингибиторных гербицидов для контроля нежелательной вегетации в растениях beta vulgaris, толерантных к als ингибиторным гербицидам |
CA2834965C (en) | 2011-05-04 | 2019-08-20 | Bayer Intellectual Property Gmbh | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant brassica, such as b. napus, plants |
ES2687545T5 (es) | 2012-12-13 | 2022-08-31 | Bayer Cropscience Ag | Uso de herbicidas inhibidores de ALS para el control de vegetación indeseada en plantas Beta vulgaris tolerantes a herbicidas inhibidores de ALS |
AR127377A1 (es) | 2021-10-15 | 2024-01-17 | Kws Saat Se & Co Kgaa | Mutantes de beta vulgaris tolerantes a herbicidas inhibidores de als |
Family Cites Families (10)
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NL157008B (nl) * | 1966-02-01 | 1978-06-15 | Monsanto Co | Werkwijze voor het bereiden van een preparaat met fytotoxische werking, gevormde preparaten met deze werking, alsmede werkwijze voor het bereiden van n-digesubstitueerde alfa-chlooraceetamidederivaten. |
US3749775A (en) | 1969-07-07 | 1973-07-31 | Stauffer Chemical Co | Insecticidal 2-aminothiazole phosphates and phosphonates |
JPS4975572A (pl) * | 1972-08-31 | 1974-07-20 | ||
JPS5031039A (pl) * | 1973-07-27 | 1975-03-27 | ||
GB1497536A (en) * | 1973-12-17 | 1978-01-12 | Lilly Industries Ltd | 2-acylaminooxazoles methods for their preparation and their use |
GB1548398A (en) * | 1975-06-05 | 1979-07-11 | Lilly Industries Ltd | Acylamino pyrroles furans and thiophenes |
GB1552125A (en) * | 1975-06-07 | 1979-09-05 | Lilly Industries Ltd | 2-acylamino oxazoles |
US4155744A (en) * | 1977-06-17 | 1979-05-22 | Monsanto Company | Herbicidal α-haloacetamides |
JPS572276A (en) * | 1980-06-07 | 1982-01-07 | Otsuka Chem Co Ltd | 1-methyl-5- n-alkyl-n-chloroacetylamino pyrazole-4- carboxylic acid ester derivative, its preparation, and herbicide for paddy rice field |
JPS588087A (ja) * | 1981-07-03 | 1983-01-18 | Toyama Chem Co Ltd | 新規セフアロスポリン類およびその中間体 |
-
1983
- 1983-01-31 CH CH536/83A patent/CH655312A5/de not_active IP Right Cessation
- 1983-02-02 DE DE3303388A patent/DE3303388C2/de not_active Expired - Lifetime
- 1983-02-04 NL NL8300427A patent/NL190919C/xx not_active IP Right Cessation
- 1983-02-07 IL IL67852A patent/IL67852A/xx not_active IP Right Cessation
- 1983-02-07 AU AU11194/83A patent/AU566009B2/en not_active Expired
- 1983-02-07 ES ES519588A patent/ES519588A0/es active Granted
- 1983-02-08 DK DK53583A patent/DK53583A/da not_active IP Right Cessation
- 1983-02-08 BR BR8300630A patent/BR8300630A/pt not_active IP Right Cessation
- 1983-02-08 IT IT19474/83A patent/IT1163085B/it active Protection Beyond IP Right Term
- 1983-02-08 KR KR1019830000493A patent/KR880002359B1/ko not_active IP Right Cessation
- 1983-02-08 DK DK053583D patent/DK171559B1/da not_active IP Right Cessation
- 1983-02-08 IE IE247/83A patent/IE55108B1/en not_active IP Right Cessation
- 1983-02-08 HU HU83429A patent/HU193036B/hu unknown
- 1983-02-08 CZ CS83867A patent/CZ278361B6/cs not_active IP Right Cessation
- 1983-02-08 TR TR21805A patent/TR21805A/xx unknown
- 1983-02-08 PL PL83240481A patent/PL140272B1/pl unknown
- 1983-02-08 JP JP58019535A patent/JPH0645617B2/ja not_active Expired - Lifetime
- 1983-02-08 CA CA000421147A patent/CA1248538A/en not_active Expired
- 1983-02-08 SK SK867-83A patent/SK86783A3/sk unknown
- 1983-02-09 EG EG85/83A patent/EG16720A/xx active
- 1983-05-09 FR FR8307966A patent/FR2530631B1/fr not_active Expired
- 1983-05-09 FR FR8307965A patent/FR2523967B1/fr not_active Expired
-
1987
- 1987-12-30 MY MY168/87A patent/MY8700168A/xx unknown
-
1994
- 1994-02-14 BG BG98475A patent/BG60498B2/bg unknown
-
2002
- 2002-09-30 NL NL350007C patent/NL350007I2/nl unknown
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