FR2513997A1 - Derives de type n-(1-triazole-(1)-yl-2,2,2-trichloroethyl)-carboxamide substitue, procede de leur preparation et composition contre l'oidium les contenant comme ingredients actifs - Google Patents
Derives de type n-(1-triazole-(1)-yl-2,2,2-trichloroethyl)-carboxamide substitue, procede de leur preparation et composition contre l'oidium les contenant comme ingredients actifs Download PDFInfo
- Publication number
- FR2513997A1 FR2513997A1 FR8207493A FR8207493A FR2513997A1 FR 2513997 A1 FR2513997 A1 FR 2513997A1 FR 8207493 A FR8207493 A FR 8207493A FR 8207493 A FR8207493 A FR 8207493A FR 2513997 A1 FR2513997 A1 FR 2513997A1
- Authority
- FR
- France
- Prior art keywords
- triazol
- trichloroethyl
- triazole
- radical
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 241000896238 Oidium Species 0.000 title claims abstract description 27
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000004480 active ingredient Substances 0.000 title description 17
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- -1 RADICAL METHYL Chemical group 0.000 claims abstract description 33
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 150000003254 radicals Chemical class 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011630 iodine Substances 0.000 claims abstract description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical class [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 14
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GUTALTICIZXUBM-UHFFFAOYSA-N n-(1,2,2,2-tetrachloroethyl)formamide Chemical compound ClC(Cl)(Cl)C(Cl)NC=O GUTALTICIZXUBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- BGWBVEWXQAGTJL-UHFFFAOYSA-N 3,3,3-trichloropropanamide Chemical class NC(=O)CC(Cl)(Cl)Cl BGWBVEWXQAGTJL-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- XUPANCKBBOYIKC-UHFFFAOYSA-N chlorocyclohexatriene Chemical compound ClC1=C=CC=C[CH]1 XUPANCKBBOYIKC-UHFFFAOYSA-N 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000003795 chemical substances by application Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 12
- 150000003852 triazoles Chemical group 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 241000209140 Triticum Species 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 9
- 230000003902 lesion Effects 0.000 description 9
- 230000001717 pathogenic effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000235349 Ascomycota Species 0.000 description 8
- 239000007900 aqueous suspension Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 230000000855 fungicidal effect Effects 0.000 description 8
- 239000000417 fungicide Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 240000008067 Cucumis sativus Species 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000227653 Lycopersicon Species 0.000 description 6
- 244000141359 Malus pumila Species 0.000 description 6
- 231100000674 Phytotoxicity Toxicity 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 230000009885 systemic effect Effects 0.000 description 5
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 235000011430 Malus pumila Nutrition 0.000 description 4
- 235000015103 Malus silvestris Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KZKYRHRAVGWEAV-UHFFFAOYSA-N 2,3-dichlorobenzamide Chemical compound NC(=O)C1=CC=CC(Cl)=C1Cl KZKYRHRAVGWEAV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000003898 horticulture Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000002969 morbid Effects 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 241000109329 Rosa xanthina Species 0.000 description 2
- 235000004789 Rosa xanthina Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- KGHXFBVYXDFJGG-UHFFFAOYSA-N (2-carbamoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(N)=O KGHXFBVYXDFJGG-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- WJCKTJBYTQLPKN-UHFFFAOYSA-N 2,4-dichloro-N-(1,2,2,2-tetrachloroethyl)benzamide Chemical compound ClC(C(Cl)(Cl)Cl)NC(C1=C(C=C(C=C1)Cl)Cl)=O WJCKTJBYTQLPKN-UHFFFAOYSA-N 0.000 description 1
- XXFUNTSOBHSMBU-UHFFFAOYSA-N 2,4-dichlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1Cl XXFUNTSOBHSMBU-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- FSCDCEJSHFGIFA-UHFFFAOYSA-N 2,6-dichloro-N-(1,2,2,2-tetrachloroethyl)benzamide Chemical compound ClC(C(Cl)(Cl)Cl)NC(C1=C(C=CC=C1Cl)Cl)=O FSCDCEJSHFGIFA-UHFFFAOYSA-N 0.000 description 1
- JHSPCUHPSIUQRB-UHFFFAOYSA-N 2,6-dichlorobenzamide Chemical compound NC(=O)C1=C(Cl)C=CC=C1Cl JHSPCUHPSIUQRB-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
- NHNAEZDWNCRWRW-UHFFFAOYSA-N 2-bromobenzamide Chemical compound NC(=O)C1=CC=CC=C1Br NHNAEZDWNCRWRW-UHFFFAOYSA-N 0.000 description 1
- WIMNRPIIQQXQLE-UHFFFAOYSA-N 2-chloro-n-(1,2,2,2-tetrachloroethyl)benzamide Chemical compound ClC(Cl)(Cl)C(Cl)NC(=O)C1=CC=CC=C1Cl WIMNRPIIQQXQLE-UHFFFAOYSA-N 0.000 description 1
- KZXYTQOZYCREPI-UHFFFAOYSA-N 2-propan-2-ylbenzamide Chemical compound CC(C)C1=CC=CC=C1C(N)=O KZXYTQOZYCREPI-UHFFFAOYSA-N 0.000 description 1
- ZESWUEBPRPGMTP-UHFFFAOYSA-N 4-nitrobenzamide Chemical compound NC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZESWUEBPRPGMTP-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000218922 Magnoliophyta Species 0.000 description 1
- HXHSJJSCCOVDKR-UHFFFAOYSA-N N-[2,2,2-trichloro-1-(1H-imidazol-2-yl)ethyl]formamide Chemical class N1C(=NC=C1)C(C(Cl)(Cl)Cl)NC=O HXHSJJSCCOVDKR-UHFFFAOYSA-N 0.000 description 1
- 241000317981 Podosphaera fuliginea Species 0.000 description 1
- 241000896203 Podosphaera pannosa Species 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical group O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- CANPFCFJURGKAX-JTQLQIEISA-N iolopride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(O)C(I)=CC=C1OC CANPFCFJURGKAX-JTQLQIEISA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- IMEQPJDEOWUNNN-UHFFFAOYSA-N n-(1,2,2,2-tetrachloroethyl)acetamide Chemical compound CC(=O)NC(Cl)C(Cl)(Cl)Cl IMEQPJDEOWUNNN-UHFFFAOYSA-N 0.000 description 1
- FJGNBLQQJYAXEU-UHFFFAOYSA-N n-(1,2,2,2-tetrachloroethyl)propanamide Chemical compound CCC(=O)NC(Cl)C(Cl)(Cl)Cl FJGNBLQQJYAXEU-UHFFFAOYSA-N 0.000 description 1
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 description 1
- BAULSHLTGVOYKM-UHFFFAOYSA-N n-butylbenzamide Chemical compound CCCCNC(=O)C1=CC=CC=C1 BAULSHLTGVOYKM-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 230000011869 shoot development Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/64—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
-
- 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
Landscapes
- 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56159083A JPS5859975A (ja) | 1981-10-06 | 1981-10-06 | Ｎ−〔１−トリアゾ−ル−（１）−イル−２，２，２−トリクロロエチル〕−置換アミド誘導体及び該誘導体を含有するうどんこ病防除剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2513997A1 true FR2513997A1 (fr) | 1983-04-08 |
| FR2513997B1 FR2513997B1 (enrdf_load_stackoverflow) | 1984-05-25 |
Family
ID=15685850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8207493A Granted FR2513997A1 (fr) | 1981-10-06 | 1982-04-30 | Derives de type n-(1-triazole-(1)-yl-2,2,2-trichloroethyl)-carboxamide substitue, procede de leur preparation et composition contre l'oidium les contenant comme ingredients actifs |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5859975A (enrdf_load_stackoverflow) |
| DE (1) | DE3215771A1 (enrdf_load_stackoverflow) |
| DK (1) | DK179182A (enrdf_load_stackoverflow) |
| FR (1) | FR2513997A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2106895B (enrdf_load_stackoverflow) |
| NL (1) | NL8201794A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05179881A (ja) * | 1991-12-27 | 1993-07-20 | Dia Consultant:Kk | 地盤の連続貫入試験方法及びその装置 |
| JP2650840B2 (ja) * | 1993-12-03 | 1997-09-10 | 和泉オプトパーツ株式会社 | 保安灯 |
| CN104530038A (zh) * | 2014-12-10 | 2015-04-22 | 沈阳药科大学 | 酰胺咪唑类衍生物及其用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE756062A (fr) * | 1969-09-11 | 1971-03-11 | Boehringer Sohn Ingelheim | Derives de 1,1,1-trichlorethane leurs procedes de fabrication et leur utilisation en tant que substances biocides |
| JPS5777678A (en) * | 1980-10-31 | 1982-05-15 | Kureha Chem Ind Co Ltd | N-(1-triazol-(1)-yl-2,2,2-trichloroethyl)-substituted benzamide derivative and agent for controlling powdery mildew containing said derivative |
-
1981
- 1981-10-06 JP JP56159083A patent/JPS5859975A/ja active Granted
-
1982
- 1982-04-22 DK DK179182A patent/DK179182A/da not_active Application Discontinuation
- 1982-04-28 GB GB08212326A patent/GB2106895B/en not_active Expired
- 1982-04-28 DE DE19823215771 patent/DE3215771A1/de not_active Ceased
- 1982-04-29 NL NL8201794A patent/NL8201794A/nl not_active Application Discontinuation
- 1982-04-30 FR FR8207493A patent/FR2513997A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2106895B (en) | 1985-10-23 |
| FR2513997B1 (enrdf_load_stackoverflow) | 1984-05-25 |
| DK179182A (da) | 1983-04-07 |
| GB2106895A (en) | 1983-04-20 |
| DE3215771A1 (de) | 1983-04-21 |
| JPH0226632B2 (enrdf_load_stackoverflow) | 1990-06-12 |
| NL8201794A (nl) | 1983-05-02 |
| JPS5859975A (ja) | 1983-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |