CS195314B2 - Fungicide and method of preparing active components therrefor - Google Patents
Fungicide and method of preparing active components therrefor Download PDFInfo
- Publication number
- CS195314B2 CS195314B2 CS766331A CS633176A CS195314B2 CS 195314 B2 CS195314 B2 CS 195314B2 CS 766331 A CS766331 A CS 766331A CS 633176 A CS633176 A CS 633176A CS 195314 B2 CS195314 B2 CS 195314B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- formula
- compound
- active ingredient
- hydrogen
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 239000000417 fungicide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- -1 R 2 is H Chemical class 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 235000005985 organic acids Nutrition 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
- 150000007524 organic acids Chemical class 0.000 claims abstract description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
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- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
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- 239000013543 active substance Substances 0.000 description 14
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- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
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- 239000003337 fertilizer Substances 0.000 description 1
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- 238000000227 grinding Methods 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 238000002372 labelling Methods 0.000 description 1
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- 229960004194 lidocaine Drugs 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
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- USFXBLZOHXOMJV-UHFFFAOYSA-N methyl 2-(n-[2-(diethylamino)acetyl]-2,6-dimethylanilino)propanoate Chemical compound CCN(CC)CC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C USFXBLZOHXOMJV-UHFFFAOYSA-N 0.000 description 1
- UDQSUVSKEUFDJI-UHFFFAOYSA-N methyl 2-[3-acetyl-2,6-dimethyl-N-(1,2,4-triazol-1-yl)anilino]propanoate Chemical compound COC(=O)C(C)N(C1=C(C(=CC=C1C)C(C)=O)C)N1N=CN=C1 UDQSUVSKEUFDJI-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 150000007530 organic bases Chemical class 0.000 description 1
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- LJQYIUMTASPIJR-UHFFFAOYSA-M sodium (2,3-dibutylnaphthalen-1-yl) sulfate Chemical compound [Na+].C1=CC=C2C(OS([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 LJQYIUMTASPIJR-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical group [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/38—Halogen atoms or nitro radicals
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1265075A CH597757A5 (en) | 1975-09-30 | 1975-09-30 | N-Amino N-alkoxy-carbonyl-alkyl anilines |
| CH1265175A CH597755A5 (en) | 1975-09-30 | 1975-09-30 | N-Amino N-alkoxy-carbonyl-alkyl anilines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195314B2 true CS195314B2 (en) | 1980-01-31 |
Family
ID=25710683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS766331A CS195314B2 (en) | 1975-09-30 | 1976-09-30 | Fungicide and method of preparing active components therrefor |
Country Status (27)
| Country | Link |
|---|---|
| US (4) | US4098895A (da) |
| JP (1) | JPS5242833A (da) |
| AR (1) | AR219908A1 (da) |
| AT (1) | AT350841B (da) |
| AU (1) | AU505869B2 (da) |
| BG (1) | BG27521A3 (da) |
| BR (1) | BR7606535A (da) |
| CA (1) | CA1064952A (da) |
| CS (1) | CS195314B2 (da) |
| DD (1) | DD128533A5 (da) |
| DE (1) | DE2643477A1 (da) |
| DK (1) | DK154651C (da) |
| EG (1) | EG12289A (da) |
| ES (1) | ES451935A1 (da) |
| FR (1) | FR2326411A1 (da) |
| GB (1) | GB1524599A (da) |
| HU (1) | HU175216B (da) |
| IE (1) | IE43632B1 (da) |
| IL (1) | IL50573A (da) |
| LU (1) | LU75895A1 (da) |
| NL (1) | NL7610793A (da) |
| NZ (1) | NZ182186A (da) |
| PH (1) | PH13696A (da) |
| PL (1) | PL112515B1 (da) |
| PT (1) | PT65655B (da) |
| SE (1) | SE434636B (da) |
| SU (1) | SU824877A3 (da) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2648008C3 (de) * | 1976-10-23 | 1980-09-04 | Basf Ag, 6700 Ludwigshafen | Acetanilide |
| EP0000539A1 (en) * | 1977-07-27 | 1979-02-07 | Ciba-Geigy Ag | Copper complexes of N-pyrazole, N-imidazole and N-triazole acetanilides, their preparation and their use as fungicides |
| US4325729A (en) * | 1977-12-13 | 1982-04-20 | Ciba-Geigy Corporation | Herbicidal and plant growth regulating pyridyloxy-phenoxy-propionic acid derivatives |
| BG28977A3 (en) * | 1978-02-02 | 1980-08-15 | Montedison Spa | Fungicide means and method for fungus fighting |
| DE2836158A1 (de) * | 1978-08-18 | 1980-02-28 | Bayer Ag | N-oxalyl-derivate von n-phenyl-aminosaeure(n)(estern), verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| CH637368A5 (de) * | 1978-10-27 | 1983-07-29 | Ciba Geigy Ag | Anilinderivate und daraus hergestellte schaedlingsbekaempfungsmittel. |
| CH641760A5 (de) * | 1978-11-27 | 1984-03-15 | Ciba Geigy Ag | Schaedlingsbekaempfungsmittel. |
| DE2901593A1 (de) * | 1979-01-17 | 1980-08-07 | Basf Ag | N-azolylessigsaeureanilide |
| US4221584A (en) * | 1979-02-09 | 1980-09-09 | Chevron Research Company | Herbicidal and plant-growth-regulating N-(heterocyclyl)-methylacetanilides |
| DE2932643A1 (de) * | 1979-08-11 | 1981-02-26 | Bayer Ag | N-pyrimidinylmethyl-halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| MA19111A1 (fr) * | 1979-10-26 | 1981-12-31 | Ciba Geigy Ag | Derives de l'homoserine,procede pour leur preparation et leur utilisation en tant que microbicides |
| DE2948704A1 (de) | 1979-12-04 | 1981-06-11 | Basf Ag, 6700 Ludwigshafen | N-substituierte 2-methylnaphthylamide, verfahren zu ihrer herstellung und diese enthaltende fungizide |
| MA19215A1 (fr) * | 1980-07-25 | 1982-04-01 | Ciba Geigy Ag | Nouveaux derives arylamines,procede pour leur fabrication et utilisation en tant que microbicides . |
| US4377587A (en) * | 1980-07-25 | 1983-03-22 | Ciba-Geigy Corporation | Arylamine derivatives and use thereof as microbicides |
| US4382954A (en) * | 1982-01-27 | 1983-05-10 | Chevron Research Company | Fungicidal N-1-substituted cyclopropyl-N-acyl-2,6-dialkylaniline |
| US4654783A (en) * | 1982-07-26 | 1987-03-31 | Data General Corporation | Unique process for loading a microcode control store in a data processing system |
| JPH0610217B2 (ja) * | 1984-04-25 | 1994-02-09 | 日本油脂株式会社 | 共重合体の製造方法 |
| US5212319A (en) * | 1990-02-26 | 1993-05-18 | Eli Lilly And Company | Intermediates to 4-amino-hexahydrobenz[cd]indoles and processes therefor |
| US10543481B2 (en) | 2011-08-19 | 2020-01-28 | Trustees Of Princeton Univesity | Targeted, metal-catalyzed fluorination of complex compounds with fluoride ion via decarboxylation |
| CN106243053B (zh) * | 2016-09-12 | 2018-09-28 | 三峡大学 | 一种三唑酰胺酮类杀菌剂，合成方法及其应用 |
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| US3124586A (en) * | 1964-03-10 | Conhz | ||
| US2676188A (en) * | 1950-12-16 | 1954-04-20 | American Home Prod | Acylated glycinamides |
| US2813861A (en) * | 1956-03-27 | 1957-11-19 | Endo Lab | Pyrrolidino-2, 6-dimethyl anilide salt of 8-[2'-methoxy-3'-(7-theophyllinyl mercuri)] propyl-coumarin-3-carboxylic acid |
| GB840361A (en) * | 1957-10-31 | 1960-07-06 | Astra Apotekarnes Kem Fab | New morpholinoacyl anilides and methods for their preparation |
| US3361626A (en) * | 1964-04-16 | 1968-01-02 | Merck & Co Inc | Method of inhibiting bacteria with tetramic acid and derivatives thereof |
| FR96375E (fr) * | 1967-12-27 | 1972-06-16 | American Cyanamid Co | Nouveaux colorants contenant des groupes méthylol ou alkoxyméthyle réactifs. |
| US3712805A (en) * | 1967-12-28 | 1973-01-23 | Shell Oil Co | Weed control employing n,n-disubstituted amino acid herbicides |
| NO122188B (da) | 1968-04-18 | 1971-06-01 | Shell Nv | |
| DE2212268C3 (de) * | 1971-03-15 | 1979-09-13 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | N-Halogenacetylanilinoessigsäureester, Verfahren zu deren Herstellung und diese enthaltende herbicide Massen |
| US3830841A (en) * | 1971-06-01 | 1974-08-20 | Monsanto Co | Herbicidal anilides |
| CA1257608A (en) * | 1972-03-10 | 1989-07-18 | Anthony B. Clayton | Certain n-phenyl amines and their use as herbicides |
| SE397191B (sv) * | 1972-10-13 | 1977-10-24 | Ciba Geigy Ag | N-(1'-alkoxikarbonyl-etyl)-n-haloacetyl-2,6-dialkylaniliner till anvendning som fungicid |
| AR205617A1 (es) * | 1973-01-08 | 1976-05-21 | Astra Pharma Prod | Procedimiento para la preparacion de derivados de aminoacilanidas primarias |
| US4008066A (en) * | 1974-04-08 | 1977-02-15 | Ciba-Geigy Corporation | Phenylaminoacetamides for regulating plant growth |
| US3944607A (en) * | 1974-10-17 | 1976-03-16 | Chevron Research Company | Herbicidal N-(N'-alkynylcarbamylmethyl)-2,6-dialkyl-α-haloacetanilides |
| US4242512A (en) * | 1979-08-06 | 1980-12-30 | Morishita Pharmaceutical Co., Ltd. | Novel thioamide derivatives containing a pyridazine group |
-
1976
- 1976-09-24 US US05/726,320 patent/US4098895A/en not_active Expired - Lifetime
- 1976-09-27 DE DE19762643477 patent/DE2643477A1/de active Granted
- 1976-09-28 CA CA262,217A patent/CA1064952A/en not_active Expired
- 1976-09-28 AR AR264879A patent/AR219908A1/es active
- 1976-09-28 LU LU75895A patent/LU75895A1/xx unknown
- 1976-09-28 DD DD7600195019A patent/DD128533A5/xx unknown
- 1976-09-28 FR FR7629115A patent/FR2326411A1/fr active Granted
- 1976-09-28 SE SE7610728A patent/SE434636B/xx not_active IP Right Cessation
- 1976-09-28 BG BG7634301A patent/BG27521A3/xx unknown
- 1976-09-29 IE IE2150/76A patent/IE43632B1/en not_active IP Right Cessation
- 1976-09-29 HU HU76CI1689A patent/HU175216B/hu not_active IP Right Cessation
- 1976-09-29 EG EG597/76A patent/EG12289A/xx active
- 1976-09-29 DK DK438776A patent/DK154651C/da not_active IP Right Cessation
- 1976-09-29 PT PT65655A patent/PT65655B/pt unknown
- 1976-09-29 AU AU18222/76A patent/AU505869B2/en not_active Expired
- 1976-09-29 ES ES451935A patent/ES451935A1/es not_active Expired
- 1976-09-29 IL IL50573A patent/IL50573A/xx unknown
- 1976-09-29 GB GB40477/76A patent/GB1524599A/en not_active Expired
- 1976-09-29 AT AT722076A patent/AT350841B/de not_active IP Right Cessation
- 1976-09-29 NZ NZ182186A patent/NZ182186A/xx unknown
- 1976-09-29 NL NL7610793A patent/NL7610793A/xx not_active Application Discontinuation
- 1976-09-29 PH PH18958A patent/PH13696A/en unknown
- 1976-09-29 PL PL1976192722A patent/PL112515B1/pl not_active IP Right Cessation
- 1976-09-30 JP JP51117899A patent/JPS5242833A/ja active Granted
- 1976-09-30 SU SU762407099A patent/SU824877A3/ru active
- 1976-09-30 BR BR7606535A patent/BR7606535A/pt unknown
- 1976-09-30 CS CS766331A patent/CS195314B2/cs unknown
-
1979
- 1979-05-14 US US06/039,012 patent/US4244962A/en not_active Expired - Lifetime
-
1980
- 1980-09-05 US US06/184,505 patent/US4349550A/en not_active Expired - Lifetime
- 1980-11-10 US US06/205,356 patent/US4402953A/en not_active Expired - Lifetime
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