DE2613167A1 - Oximcarbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozide - Google Patents
Oximcarbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozideInfo
- Publication number
- DE2613167A1 DE2613167A1 DE19762613167 DE2613167A DE2613167A1 DE 2613167 A1 DE2613167 A1 DE 2613167A1 DE 19762613167 DE19762613167 DE 19762613167 DE 2613167 A DE2613167 A DE 2613167A DE 2613167 A1 DE2613167 A1 DE 2613167A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- oximino
- dimethyl
- spp
- diluent
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 43
- 150000002923 oximes Chemical class 0.000 title claims description 19
- 239000005645 nematicide Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000642 acaricide Substances 0.000 title description 3
- 239000002917 insecticide Substances 0.000 title description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title 1
- -1 Oxime carbamates Chemical class 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 25
- 239000003085 diluting agent Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 21
- 239000011230 binding agent Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 241000238631 Hexapoda Species 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 8
- 241000244206 Nematoda Species 0.000 claims description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- 230000000895 acaricidal effect Effects 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000012312 sodium hydride Substances 0.000 claims description 7
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 7
- 230000000749 insecticidal effect Effects 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 241000238876 Acari Species 0.000 claims description 4
- JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical compound COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 241000341511 Nematodes Species 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 53
- 239000001273 butane Substances 0.000 description 42
- 239000001294 propane Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 238000012360 testing method Methods 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000003995 emulsifying agent Substances 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 230000006378 damage Effects 0.000 description 7
- 229910052751 metal Chemical class 0.000 description 7
- 239000002184 metal Chemical class 0.000 description 7
- 230000001069 nematicidal effect Effects 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- 230000009885 systemic effect Effects 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 5
- DKEKURXRUXRNES-UHFFFAOYSA-N bis(1h-pyrrol-2-yl)methanone Chemical class C=1C=CNC=1C(=O)C1=CC=CN1 DKEKURXRUXRNES-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
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- 241001608567 Phaedon cochleariae Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
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- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- 238000001953 recrystallisation Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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- 239000012973 diazabicyclooctane Substances 0.000 description 3
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- 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
- 239000004579 marble Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- BJEPVURQDBDEAZ-UHFFFAOYSA-N n-(1-chloro-3,3-dimethylbutan-2-ylidene)hydroxylamine Chemical compound CC(C)(C)C(CCl)=NO BJEPVURQDBDEAZ-UHFFFAOYSA-N 0.000 description 1
- QGRBGPKKFIYPSW-UHFFFAOYSA-N n-ethyl-n-(methoxymethyl)ethanamine Chemical compound CCN(CC)COC QGRBGPKKFIYPSW-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VYPHMDCIYPHFKS-UHFFFAOYSA-N trifluoro(isocyanato)methane Chemical compound FC(F)(F)N=C=O VYPHMDCIYPHFKS-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- 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
- C07D231/16—Halogen atoms or nitro radicals
-
- 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
- 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
- C07D233/66—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 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
-
- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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
- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
-
- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur 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
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (24)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19762613167 DE2613167A1 (de) | 1976-03-27 | 1976-03-27 | Oximcarbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozide |
NO77770874A NO770874L (no) | 1976-03-27 | 1977-03-11 | Oksimcarbamater og deres anvendelse som insekticider, akaricider og nematocider. |
RO7789706A RO70570A (fr) | 1976-03-27 | 1977-03-18 | Procede de preparation des carbamates d'oxymes |
CS771903A CS191336B2 (en) | 1976-03-27 | 1977-03-22 | Insecticide,acricide and nematocide means and method of making the active substances |
SU772462916A SU736857A3 (ru) | 1976-03-27 | 1977-03-23 | Инсектоакарицидонематоцидное средство |
SE7703387A SE7703387L (sv) | 1976-03-27 | 1977-03-24 | Oximkarbamater till anvendning som insekticider, akaricider och nematocider och sett for deras framstellning |
AU23601/77A AU2360177A (en) | 1976-03-27 | 1977-03-24 | Oxime carbamates |
NL7703204A NL7703204A (nl) | 1976-03-27 | 1977-03-24 | Oximecarbamaten, een werkwijze voor de bereiding daarvan en de toepassing daarvan als insecticide, acaricide en nematocide. |
GB12448/77A GB1534477A (en) | 1976-03-27 | 1977-03-24 | Oximecarbamates and their use as insecticides,acaricides and nematicides |
NZ183684A NZ183684A (en) | 1976-03-27 | 1977-03-24 | Cyclic azo-substituted-(carbamoyl hydroxyimino)-alkanes and nematicidal and arthropodicidal compositions |
PT66347A PT66347B (en) | 1976-03-27 | 1977-03-24 | Process for preparing an insecticidal acaricidal and nematicidal composition containing oxime carbamates and salts an complexes of metal thereof |
TR19212A TR19212A (tr) | 1976-03-27 | 1977-03-25 | Oksim-karbamatlar,bunlarin hazirlanisina ait usuller ve bunlarin ensektisidler akarisidler ve nematosidler olarak kullanilmalari |
BR1885/77A BR7701885A (pt) | 1976-03-27 | 1977-03-25 | Carbamatos de oxima processos para sua preparacao composicoes inseticidas acaricidas e nematicidas e seu emprego |
AT210677A AT353552B (de) | 1976-03-27 | 1977-03-25 | Insektizides, akarizides und nematozides mittel |
DK132177A DK132177A (da) | 1976-03-27 | 1977-03-25 | Oximcarbamater fremgangsmade til deres fremstilling og deres anvendelse som insecticider acaricider og nematodicider |
DD7700198076A DD131711A5 (de) | 1976-03-27 | 1977-03-25 | Insektizide,akarizide und nematozide mittel |
FR7709114A FR2345435A1 (fr) | 1976-03-27 | 1977-03-25 | Nouveaux carbamates d'oximes, leur procede de preparation et leur application comme insecticides, acaricides et nematicides |
ES457197A ES457197A1 (es) | 1976-03-27 | 1977-03-25 | Procedimiento para preparar carbamatos de oxima. |
IL7751738A IL51738A0 (en) | 1976-03-27 | 1977-03-25 | Novel oxime-carbamates their preparation and their use as insecticides acaricides and nematicides |
BE176134A BE852897A (fr) | 1976-03-27 | 1977-03-25 | Nouveaux carbamates d'oximes |
JP3283477A JPS52116464A (en) | 1976-03-27 | 1977-03-26 | Novel oximecarbamate*prepatation thereof and its use as insecticide*acaricide and nematocide |
PL1977196944A PL101584B1 (pl) | 1976-03-27 | 1977-03-26 | An insecticide,an acaricide and a nematocide |
EG171/77A EG12606A (en) | 1976-03-27 | 1977-03-26 | Novel oxime carbamates and their use as insecticides acaricides and nematicides |
ZA00771811A ZA771811B (en) | 1976-03-27 | 1977-08-25 | Novel oxime-carbamates and their use as insecticides,acaricides and nematicides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19762613167 DE2613167A1 (de) | 1976-03-27 | 1976-03-27 | Oximcarbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozide |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2613167A1 true DE2613167A1 (de) | 1977-10-06 |
Family
ID=5973635
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19762613167 Pending DE2613167A1 (de) | 1976-03-27 | 1976-03-27 | Oximcarbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozide |
Country Status (23)
Country | Link |
---|---|
JP (1) | JPS52116464A (fr) |
AT (1) | AT353552B (fr) |
AU (1) | AU2360177A (fr) |
BE (1) | BE852897A (fr) |
BR (1) | BR7701885A (fr) |
CS (1) | CS191336B2 (fr) |
DD (1) | DD131711A5 (fr) |
DE (1) | DE2613167A1 (fr) |
DK (1) | DK132177A (fr) |
EG (1) | EG12606A (fr) |
ES (1) | ES457197A1 (fr) |
FR (1) | FR2345435A1 (fr) |
GB (1) | GB1534477A (fr) |
IL (1) | IL51738A0 (fr) |
NL (1) | NL7703204A (fr) |
NO (1) | NO770874L (fr) |
NZ (1) | NZ183684A (fr) |
PL (1) | PL101584B1 (fr) |
PT (1) | PT66347B (fr) |
RO (1) | RO70570A (fr) |
SE (1) | SE7703387L (fr) |
TR (1) | TR19212A (fr) |
ZA (1) | ZA771811B (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0005249A2 (fr) * | 1978-05-10 | 1979-11-14 | Bayer Ag | Carbamates substitués d'alkanyl-azolyl-oximes, procédé pour leur préparation et leur utilisation comme insecticides, acaricides et nématocides |
EP0005780A1 (fr) * | 1978-06-03 | 1979-12-12 | Bayer Ag | Thio-bis-amines N,N' asymétriquement substituées, procédé pour leur préparation ainsi que leur application comme insecticides, acaricides et nématocides |
EP0031911A2 (fr) * | 1979-12-19 | 1981-07-15 | Bayer Ag | Triazolylméthyl-tert.-butyl-cétones substituées, procédé pour leur préparation ainsi que leur utilisation comme agents protecteurs des plantes et comme intermédiaires |
EP0090936A2 (fr) * | 1982-03-06 | 1983-10-12 | Bayer Ag | Ethers azolyléthyle-oximinoalkyl substitués, leur procédé de préparation et leur application comme fongicides |
EP0094572A2 (fr) * | 1982-05-19 | 1983-11-23 | Bayer Ag | Dérivés de l'1-azolyl-2-oximino-butane, leur procédé de fabrication et leur application comme fongicides et agents régulateurs de croissance des plantes |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4353915A (en) * | 1977-02-04 | 1982-10-12 | Bayer Aktiengesellschaft | Combating pests with 2-(azol-1-yl)-aldoxime-carbamates |
GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3634447A (en) * | 1969-10-08 | 1972-01-11 | American Cyanamid Co | Substituted nitroimidazoles and method of preparing the same |
US3711495A (en) * | 1970-01-07 | 1973-01-16 | Merck & Co Inc | Isoxazalin-3-yl-substituted-5-nitroimidazoles |
DE2311177A1 (de) * | 1973-03-07 | 1974-09-19 | Hoechst Ag | O-(dialkylaminoalkyl)-1-alkyl-5nitroimidazol-(2)-aldoxime und verfahren zu ihrer herstellung |
-
1976
- 1976-03-27 DE DE19762613167 patent/DE2613167A1/de active Pending
-
1977
- 1977-03-11 NO NO77770874A patent/NO770874L/no unknown
- 1977-03-18 RO RO7789706A patent/RO70570A/fr unknown
- 1977-03-22 CS CS771903A patent/CS191336B2/cs unknown
- 1977-03-24 AU AU23601/77A patent/AU2360177A/en not_active Expired
- 1977-03-24 NL NL7703204A patent/NL7703204A/xx not_active Application Discontinuation
- 1977-03-24 PT PT66347A patent/PT66347B/pt unknown
- 1977-03-24 SE SE7703387A patent/SE7703387L/xx unknown
- 1977-03-24 NZ NZ183684A patent/NZ183684A/xx unknown
- 1977-03-24 GB GB12448/77A patent/GB1534477A/en not_active Expired
- 1977-03-25 TR TR19212A patent/TR19212A/xx unknown
- 1977-03-25 DD DD7700198076A patent/DD131711A5/xx unknown
- 1977-03-25 IL IL7751738A patent/IL51738A0/xx unknown
- 1977-03-25 FR FR7709114A patent/FR2345435A1/fr not_active Withdrawn
- 1977-03-25 ES ES457197A patent/ES457197A1/es not_active Expired
- 1977-03-25 BE BE176134A patent/BE852897A/fr unknown
- 1977-03-25 AT AT210677A patent/AT353552B/de not_active IP Right Cessation
- 1977-03-25 BR BR1885/77A patent/BR7701885A/pt unknown
- 1977-03-25 DK DK132177A patent/DK132177A/da not_active IP Right Cessation
- 1977-03-26 PL PL1977196944A patent/PL101584B1/pl unknown
- 1977-03-26 JP JP3283477A patent/JPS52116464A/ja active Pending
- 1977-03-26 EG EG171/77A patent/EG12606A/xx active
- 1977-08-25 ZA ZA00771811A patent/ZA771811B/xx unknown
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0005249A2 (fr) * | 1978-05-10 | 1979-11-14 | Bayer Ag | Carbamates substitués d'alkanyl-azolyl-oximes, procédé pour leur préparation et leur utilisation comme insecticides, acaricides et nématocides |
EP0005249A3 (en) * | 1978-05-10 | 1979-11-28 | Bayer Aktiengesellschaft | Substituted alkanyl-azolyl carbamates, process for their preparation and their use as insecticides, acaricides and nematocides |
US4344953A (en) * | 1978-05-10 | 1982-08-17 | Bayer Aktiengesellschaft | Combating pests with substituted alkanylazolyl oxime-carbamates |
EP0005780A1 (fr) * | 1978-06-03 | 1979-12-12 | Bayer Ag | Thio-bis-amines N,N' asymétriquement substituées, procédé pour leur préparation ainsi que leur application comme insecticides, acaricides et nématocides |
EP0031911A2 (fr) * | 1979-12-19 | 1981-07-15 | Bayer Ag | Triazolylméthyl-tert.-butyl-cétones substituées, procédé pour leur préparation ainsi que leur utilisation comme agents protecteurs des plantes et comme intermédiaires |
EP0031911A3 (en) * | 1979-12-19 | 1981-07-22 | Bayer Ag | Substituted triazolylmethyl-tert.-butyl-ketones, process for their preparation and their use as plant protecting agents as well as intermediates |
EP0090936A2 (fr) * | 1982-03-06 | 1983-10-12 | Bayer Ag | Ethers azolyléthyle-oximinoalkyl substitués, leur procédé de préparation et leur application comme fongicides |
EP0090936A3 (en) * | 1982-03-06 | 1983-11-09 | Bayer Ag | Substituted azolylethyl-oximinoalkyl ethers, process for their preparation and their use as fungicides |
US4489081A (en) * | 1982-03-06 | 1984-12-18 | Bayer Aktiengesellschaft | Fungicidally active novel substituted azolylethyl oximinoalkyl ethers |
US4582846A (en) * | 1982-03-06 | 1986-04-15 | Bayer Aktiengesellschaft | Fungicidally active novel substituted azolylethyl oximinoalkyl ethers |
EP0094572A2 (fr) * | 1982-05-19 | 1983-11-23 | Bayer Ag | Dérivés de l'1-azolyl-2-oximino-butane, leur procédé de fabrication et leur application comme fongicides et agents régulateurs de croissance des plantes |
EP0094572A3 (en) * | 1982-05-19 | 1984-02-22 | Bayer Ag | 1-azolyl-oximino-butane derivatives, process for their preparation and their use as fungicides and plant growth regulators |
Also Published As
Publication number | Publication date |
---|---|
DD131711A5 (de) | 1978-07-19 |
NZ183684A (en) | 1979-10-25 |
PT66347B (en) | 1978-08-16 |
BR7701885A (pt) | 1978-02-08 |
ES457197A1 (es) | 1978-08-16 |
BE852897A (fr) | 1977-09-26 |
RO70570A (fr) | 1982-09-09 |
NO770874L (no) | 1977-09-28 |
TR19212A (tr) | 1978-06-07 |
DK132177A (da) | 1977-09-28 |
ZA771811B (en) | 1978-02-22 |
NL7703204A (nl) | 1977-09-29 |
JPS52116464A (en) | 1977-09-29 |
AU2360177A (en) | 1978-09-28 |
FR2345435A1 (fr) | 1977-10-21 |
CS191336B2 (en) | 1979-06-29 |
IL51738A0 (en) | 1977-05-31 |
PL101584B1 (pl) | 1979-01-31 |
AT353552B (de) | 1979-11-26 |
PT66347A (en) | 1977-04-01 |
EG12606A (en) | 1980-03-31 |
ATA210677A (de) | 1979-04-15 |
PL196944A1 (pl) | 1978-01-02 |
GB1534477A (en) | 1978-12-06 |
SE7703387L (sv) | 1977-09-28 |
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