IL36458A - Carbamoyl oximes, their preparation and use to fight fungi and phytopathogenic viruses - Google Patents
Carbamoyl oximes, their preparation and use to fight fungi and phytopathogenic virusesInfo
- Publication number
- IL36458A IL36458A IL36458A IL3645871A IL36458A IL 36458 A IL36458 A IL 36458A IL 36458 A IL36458 A IL 36458A IL 3645871 A IL3645871 A IL 3645871A IL 36458 A IL36458 A IL 36458A
- Authority
- IL
- Israel
- Prior art keywords
- carbamoyl
- oxime
- formula
- nonanone
- bornyl
- Prior art date
Links
- 241000233866 Fungi Species 0.000 title claims description 13
- 241000700605 Viruses Species 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 9
- 230000003032 phytopathogenic effect Effects 0.000 title claims description 8
- 239000013543 active substance Substances 0.000 claims description 37
- -1 carbamoyl oximes Chemical class 0.000 claims description 27
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 239000000969 carrier Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
- CBERVMGFVLWZSU-UHFFFAOYSA-N 3,5,5-trimethylcyclohexene Chemical compound CC1CC(C)(C)CC=C1 CBERVMGFVLWZSU-UHFFFAOYSA-N 0.000 description 39
- 239000003795 chemical substances by application Substances 0.000 description 20
- 208000015181 infectious disease Diseases 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 16
- 239000000725 suspension Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 240000008067 Cucumis sativus Species 0.000 description 8
- 239000006072 paste Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 241000221785 Erysiphales Species 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 235000009849 Cucumis sativus Nutrition 0.000 description 6
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- CHOOCIQDWNAXQQ-UHFFFAOYSA-N 1,5,5-trimethylcyclohexene Chemical compound CC1=CCCC(C)(C)C1 CHOOCIQDWNAXQQ-UHFFFAOYSA-N 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000010410 dusting Methods 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 241000221577 Uromyces appendiculatus Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000233679 Peronosporaceae Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 240000006677 Vicia faba Species 0.000 description 3
- 235000010749 Vicia faba Nutrition 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JCRNSBKSAQHNIN-UHFFFAOYSA-N 2,4-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC(CCCC)=C21 JCRNSBKSAQHNIN-UHFFFAOYSA-N 0.000 description 2
- FBAAWFXZNSCIGK-UHFFFAOYSA-N 3-isocyanato-4,7,7-trimethylbicyclo[2.2.1]heptane Chemical compound C1CC2(C)C(N=C=O)CC1C2(C)C FBAAWFXZNSCIGK-UHFFFAOYSA-N 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 244000203593 Piper nigrum Species 0.000 description 2
- 241000221535 Pucciniales Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229940115440 aluminum sodium silicate Drugs 0.000 description 2
- 235000019993 champagne Nutrition 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DFMZGZYTSBUWAH-UHFFFAOYSA-N n-nonan-5-ylidenehydroxylamine Chemical compound CCCCC(=NO)CCCC DFMZGZYTSBUWAH-UHFFFAOYSA-N 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000429 sodium aluminium silicate Substances 0.000 description 2
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 230000003253 viricidal effect Effects 0.000 description 2
- VTWKXBJHBHYJBI-VURMDHGXSA-N (nz)-n-benzylidenehydroxylamine Chemical compound O\N=C/C1=CC=CC=C1 VTWKXBJHBHYJBI-VURMDHGXSA-N 0.000 description 1
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GQVLBFQEABXQDC-UHFFFAOYSA-N 3,3,5-trimethylcyclohexene Chemical compound CC1CC=CC(C)(C)C1 GQVLBFQEABXQDC-UHFFFAOYSA-N 0.000 description 1
- OVMVMMNHNMZUAS-UHFFFAOYSA-N 4-methyl-1,3-dithiolane-2-thione Chemical group CC1CSC(=S)S1 OVMVMMNHNMZUAS-UHFFFAOYSA-N 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000002567 Capsicum annuum Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000723762 Potato virus Y Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 235000002560 Solanum lycopersicum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 241000723873 Tobacco mosaic virus Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000221576 Uromyces Species 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- OKSRBEMKUSZPOX-UHFFFAOYSA-N aluminum;sodium;silicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])([O-])[O-] OKSRBEMKUSZPOX-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- OKVYEXCEUZCQEH-UHFFFAOYSA-N benzenesulfonic acid;formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.OS(=O)(=O)C1=CC=CC=C1.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 OKVYEXCEUZCQEH-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- DSSYKIVIOFKYAU-UHFFFAOYSA-N bornanone Natural products C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
- PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide 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
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000012219 potassium aluminium silicate Nutrition 0.000 description 1
- 239000000441 potassium aluminium silicate Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 101150068774 thyX gene Proteins 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH431970A CH536286A (de) | 1970-03-23 | 1970-03-23 | Verfahren zur Herstellung von neuen Carbamoyl-oximen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL36458A0 IL36458A0 (en) | 1971-05-26 |
| IL36458A true IL36458A (en) | 1974-10-22 |
Family
ID=4273860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL36458A IL36458A (en) | 1970-03-23 | 1971-03-22 | Carbamoyl oximes, their preparation and use to fight fungi and phytopathogenic viruses |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3843724A (de) |
| AT (2) | AT306049B (de) |
| BE (1) | BE764620A (de) |
| CA (1) | CA975791A (de) |
| CH (1) | CH536286A (de) |
| DE (1) | DE2113752C3 (de) |
| DK (1) | DK129578B (de) |
| ES (1) | ES389427A1 (de) |
| FR (1) | FR2084981A5 (de) |
| GB (1) | GB1351473A (de) |
| IL (1) | IL36458A (de) |
| NL (1) | NL7103833A (de) |
| SE (1) | SE375525B (de) |
| SU (1) | SU370751A3 (de) |
| ZA (1) | ZA711848B (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932509A (en) * | 1970-03-23 | 1976-01-13 | Ciba-Geigy Corporation | Carbamoyloximes derivatives |
| US3875232A (en) * | 1971-04-08 | 1975-04-01 | Diamond Shamrock Corp | AC Ketoxime carbamates |
| US3968240A (en) * | 1972-03-16 | 1976-07-06 | Somar Manufacturing Co., Ltd. | α-Chloro-o-acylbenzaldoxime derivatives as slime control agents |
| US4018645A (en) * | 1972-03-16 | 1977-04-19 | Somar Manufacturing Co., Ltd. | Method of controlling slime during paper manufacture using alpha-chloro-acylbenzaldoxime derivatives |
| DE2841714A1 (de) * | 1978-09-25 | 1980-04-10 | Basf Ag | Verfahren zur herstellung von 2,2- dimethyl-4-cyan-butyraldoxim-n-methyl- carbamat |
| DE3019491C2 (de) * | 1980-05-22 | 1985-02-21 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von Oximcarbamaten |
| DE3144600A1 (de) * | 1981-11-10 | 1983-05-19 | Hoechst Ag, 6230 Frankfurt | "carbamoyloxime, verfahren zu ihrer herstellung und ihre verwendung als herbizide" |
| CN1104411C (zh) * | 1998-02-27 | 2003-04-02 | 中国农业大学 | (E)－O－酰基－α－氧代环十二酮肟,其制备方法和作为除草剂的用途 |
| CN100357262C (zh) * | 2002-05-10 | 2007-12-26 | 中国农业大学 | (E)－O－(烃基)－α－氧代环十二酮肟,其制备方法和作为杀真菌剂的用途 |
-
1970
- 1970-03-23 CH CH431970A patent/CH536286A/de not_active IP Right Cessation
-
1971
- 1971-03-15 US US00124527A patent/US3843724A/en not_active Expired - Lifetime
- 1971-03-18 DK DK132071AA patent/DK129578B/da unknown
- 1971-03-18 SE SE7103509A patent/SE375525B/xx unknown
- 1971-03-22 CA CA108,324A patent/CA975791A/en not_active Expired
- 1971-03-22 AT AT243371A patent/AT306049B/de not_active IP Right Cessation
- 1971-03-22 DE DE2113752A patent/DE2113752C3/de not_active Expired
- 1971-03-22 BE BE764620A patent/BE764620A/xx unknown
- 1971-03-22 IL IL36458A patent/IL36458A/en unknown
- 1971-03-22 ZA ZA711848A patent/ZA711848B/xx unknown
- 1971-03-22 ES ES389427A patent/ES389427A1/es not_active Expired
- 1971-03-22 FR FR7109960A patent/FR2084981A5/fr not_active Expired
- 1971-03-22 AT AT146072A patent/AT313638B/de not_active IP Right Cessation
- 1971-03-22 NL NL7103833A patent/NL7103833A/xx unknown
- 1971-03-23 SU SU1634592A patent/SU370751A3/ru active
- 1971-04-19 GB GB2489771*A patent/GB1351473A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2113752B2 (de) | 1974-05-30 |
| AT313638B (de) | 1974-02-25 |
| CA975791A (en) | 1975-10-07 |
| SU370751A3 (de) | 1973-02-15 |
| NL7103833A (de) | 1971-09-27 |
| SE375525B (de) | 1975-04-21 |
| US3843724A (en) | 1974-10-22 |
| CH536286A (de) | 1973-04-30 |
| DK129578C (de) | 1975-03-24 |
| ES389427A1 (es) | 1974-03-16 |
| ZA711848B (en) | 1971-12-29 |
| AT306049B (de) | 1973-03-26 |
| DK129578B (da) | 1974-10-28 |
| FR2084981A5 (de) | 1971-12-17 |
| IL36458A0 (en) | 1971-05-26 |
| DE2113752C3 (de) | 1975-01-16 |
| BE764620A (fr) | 1971-09-22 |
| DE2113752A1 (de) | 1971-10-07 |
| GB1351473A (en) | 1974-05-01 |
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