DD143846A5 - Verwendung von n,n-diallyl-dichloracetamid - Google Patents

Verwendung von n,n-diallyl-dichloracetamid Download PDF

Info

Publication number: DD143846A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; alkyl; methyl; acid; optionally substituted
Prior art date: 1978-06-28

Application number

DD79213878A

Other languages

German (de)

English (en)

Inventor

Robert R Schmidt

Wilfried Faust

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1978-06-28

Filing date

1979-06-25

Publication date

1980-09-17

1979-06-25 Application filed by Bayer Ag filed Critical Bayer Ag

1980-09-17 Publication of DD143846A5 publication Critical patent/DD143846A5/de

Links

YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 title abstract description 6
239000000729 antidote Substances 0.000 claims abstract description 30
-1 H a logenalkyl Chemical group 0.000 claims description 50
125000000217 alkyl group Chemical group 0.000 claims description 40
239000002253 acid Substances 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 28
150000002367 halogens Chemical class 0.000 claims description 24
125000001188 haloalkyl group Chemical group 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
229910052751 metal Chemical class 0.000 claims description 15
239000002184 metal Chemical class 0.000 claims description 15
150000002431 hydrogen Chemical class 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 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
244000038559 crop plants Species 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000003107 substituted aryl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
150000008061 acetanilides Chemical class 0.000 abstract description 20
230000006378 damage Effects 0.000 abstract description 9
239000000460 chlorine Substances 0.000 description 95
125000004432 carbon atom Chemical group C* 0.000 description 41
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
150000001875 compounds Chemical class 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
238000000034 method Methods 0.000 description 32
230000002363 herbicidal effect Effects 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
241000196324 Embryophyta Species 0.000 description 21
239000000203 mixture Substances 0.000 description 20
239000004480 active ingredient Substances 0.000 description 18
229910052801 chlorine Inorganic materials 0.000 description 18
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 17
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
238000002360 preparation method Methods 0.000 description 17
239000003960 organic solvent Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
239000011230 binding agent Substances 0.000 description 13
229910052731 fluorine Inorganic materials 0.000 description 13
239000011737 fluorine Substances 0.000 description 13
125000005843 halogen group Chemical group 0.000 description 13
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
125000001309 chloro group Chemical group Cl* 0.000 description 12
239000007858 starting material Substances 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
239000004009 herbicide Substances 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
239000000243 solution Substances 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000000706 filtrate Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
229930040373 Paraformaldehyde Natural products 0.000 description 5
240000008042 Zea mays Species 0.000 description 5
235000002017 Zea mays subsp mays Nutrition 0.000 description 5
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
239000013078 crystal Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000008187 granular material Substances 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
229920002866 paraformaldehyde Polymers 0.000 description 5
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001448 anilines Chemical class 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
150000002429 hydrazines Chemical class 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
239000003921 oil Substances 0.000 description 4
238000005554 pickling Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000000725 suspension Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
241000219318 Amaranthus Species 0.000 description 3
241000192043 Echinochloa Species 0.000 description 3
241000219146 Gossypium Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000209094 Oryza Species 0.000 description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
229960001413 acetanilide Drugs 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000969 carrier Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
235000009973 maize Nutrition 0.000 description 3
DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
238000009331 sowing Methods 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 2
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
JAVFLGCTQKOUTK-UHFFFAOYSA-N 2-(2,6-diethylanilino)acetohydrazide Chemical compound CCC1=CC=CC(CC)=C1NCC(=O)NN JAVFLGCTQKOUTK-UHFFFAOYSA-N 0.000 description 2
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical class [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
239000004606 Fillers/Extenders Substances 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 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 description 2
235000021506 Ipomoea Nutrition 0.000 description 2
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UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
241000209117 Panicum Species 0.000 description 2
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
241000209504 Poaceae Species 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
235000007201 Saccharum officinarum Nutrition 0.000 description 2
241000207763 Solanum Species 0.000 description 2
235000002634 Solanum Nutrition 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
229910052783 alkali metal Chemical group 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
150000001340 alkali metals Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
229940075522 antidotes Drugs 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
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229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000007872 degassing Methods 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
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239000000975 dye Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
238000002955 isolation Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
150000004866 oxadiazoles Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
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OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- 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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- 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
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
- 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

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DD79213878A 1978-06-28 1979-06-25 Verwendung von n,n-diallyl-dichloracetamid DD143846A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782828303 DE2828303A1 (de)	1978-06-28	1978-06-28	Verwendung von n,n-diallyl-dichloracetamid zur verbesserung der kulturpflanzen- vertraeglichkeit von herbizid wirksamen acetaniliden

Publications (1)

Publication Number	Publication Date
DD143846A5 true DD143846A5 (de)	1980-09-17

Family

ID=6042970

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79213878A DD143846A5 (de)	1978-06-28	1979-06-25	Verwendung von n,n-diallyl-dichloracetamid

Country Status (16)

Country	Link
US (1)	US4312664A (fr)
EP (1)	EP0006541A3 (fr)
JP (1)	JPS557279A (fr)
AU (1)	AU4843479A (fr)
BR (1)	BR7904079A (fr)
CA (1)	CA1128765A (fr)
DD (1)	DD143846A5 (fr)
DE (1)	DE2828303A1 (fr)
DK (1)	DK272579A (fr)
ES (1)	ES481983A1 (fr)
IL (1)	IL57641A0 (fr)
PL (1)	PL216609A1 (fr)
PT (1)	PT69789A (fr)
RO (1)	RO75806A (fr)
TR (1)	TR19972A (fr)
ZA (1)	ZA793211B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2930448A1 (de) *	1979-07-26	1981-02-26	Bayer Ag	Gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide
DE3035394A1 (de) *	1980-09-19	1982-05-06	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von pyrazol
HU194686B (en) *	1985-05-10	1988-03-28	Eszakmagyar Vegyimuevek	Herbicidal composition of prolonged action, comprising alpha-chlorine-acetanilide derivatives as active substance
KR100724676B1 (ko) *	2000-02-16	2007-06-07	이시하라 산교 가부시끼가이샤	페나실아민 유도체, 이들의 제조 방법 및 이들을 함유하는유해 생물 방제제
JP4799744B2 (ja) *	2000-02-16	2011-10-26	石原産業株式会社	フェナシルアミン誘導体、それらの製造方法及びそれらを含有する有害生物防除剤

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1174865A (fr) *	1971-04-16	1984-09-25	Ferenc M. Pallos	Herbicides a base de thiolcarbamate contenant un antidote azote
US3907544A (en) *	1971-06-01	1975-09-23	Monsanto Co	Herbicidal 2-halo-N-(cyclicimidoalkylene)-substituted acetanilides
US3769301A (en) *	1971-06-01	1973-10-30	Monsanto Co	Herbicidal-n-(acyl-tertiary-amidoalkyl)anilides
CH574207A5 (fr) *	1973-01-25	1976-04-15	Ciba Geigy Ag
US4053297A (en) *	1975-04-21	1977-10-11	Velsicol Chemical Corporation	Selective herbicidal compositions
US4055410A (en) *	1976-03-15	1977-10-25	E. I. Du Pont De Nemours And Company	Substituted bromo- or chloroacetamide herbicides
DE2648008C3 (de) *	1976-10-23	1980-09-04	Basf Ag, 6700 Ludwigshafen	Acetanilide
IL53938A0 (en) *	1977-02-02	1978-04-30	Bayer Ag	Novel n-substituted halogenoacetanilides, their preparation and their use as herbicides
DE2726253A1 (de) *	1977-06-10	1978-12-21	Bayer Ag	N-acylmethyl-chloracetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2805757A1 (de) *	1978-02-10	1979-08-16	Bayer Ag	N-azolylalkyl-halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide

1978
- 1978-06-28 DE DE19782828303 patent/DE2828303A1/de not_active Withdrawn
1979
- 1979-06-04 US US06/045,371 patent/US4312664A/en not_active Expired - Lifetime
- 1979-06-15 EP EP79101942A patent/EP0006541A3/fr not_active Withdrawn
- 1979-06-20 PT PT69789A patent/PT69789A/pt unknown
- 1979-06-25 IL IL7957641A patent/IL57641A0/xx unknown
- 1979-06-25 DD DD79213878A patent/DD143846A5/de unknown
- 1979-06-26 PL PL21660979A patent/PL216609A1/xx unknown
- 1979-06-26 TR TR19972A patent/TR19972A/xx unknown
- 1979-06-26 JP JP7976479A patent/JPS557279A/ja active Pending
- 1979-06-27 AU AU48434/79A patent/AU4843479A/en not_active Abandoned
- 1979-06-27 BR BR7904079A patent/BR7904079A/pt unknown
- 1979-06-27 CA CA330,707A patent/CA1128765A/fr not_active Expired
- 1979-06-27 ES ES481983A patent/ES481983A1/es not_active Expired
- 1979-06-27 DK DK272579A patent/DK272579A/da unknown
- 1979-06-27 ZA ZA793211A patent/ZA793211B/xx unknown
- 1979-06-28 RO RO7997985A patent/RO75806A/fr unknown

Also Published As

Publication number	Publication date
JPS557279A (en)	1980-01-19
RO75806A (fr)	1981-02-28
AU4843479A (en)	1980-01-03
PL216609A1 (fr)	1980-03-24
CA1128765A (fr)	1982-08-03
DE2828303A1 (de)	1980-01-17
US4312664A (en)	1982-01-26
BR7904079A (pt)	1980-03-25
DK272579A (da)	1979-12-29
PT69789A (en)	1979-07-01
ZA793211B (en)	1980-08-27
TR19972A (tr)	1980-06-02
ES481983A1 (es)	1980-02-16
IL57641A0 (en)	1979-10-31
EP0006541A2 (fr)	1980-01-09
EP0006541A3 (fr)	1980-01-23

Publication	Publication Date	Title
EP0185256B1 (fr)	1991-01-30	Dérivés de triazole, leur préparation et leur utilisation comme pesticides
DD144350A5 (de)	1980-10-15	Mittel zur verhuetung von herbizidschaeden an kulturpflanzen
DE2828265A1 (de)	1980-01-17	Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen acetaniliden
DE2832234A1 (de)	1980-01-31	Alpha -azolyl-keto-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
EP0003539B1 (fr)	1981-04-08	N-Azolylalcoyl-halogénoacétanilides, leur procédé de synthèse ainsi que leur utilisation comme herbicides
EP0006542A2 (fr)	1980-01-09	Utilisation de la N-dichloracétyl-1,2,3,4-tétrahydroquinoline comme antidote pour la protection des cultures contre les dégâts occasionnés par les herbicides à base d'acétanilides; combinaisons herbicides ainsi obtenues et procédé pour leur préparation
EP0014880B1 (fr)	1982-09-22	Amides d'acides phénoxycarboxyliques, procédé pour leur préparation et leur utilisation comme herbicides
EP0023305A1 (fr)	1981-02-04	Utilisation de N,N'-bis-(halogène acyle)-diaza-cycloalcanes comme antidotes pour la protection de plantes cultivées contre des dommages causés par des herbicides
US4312664A (en)	1982-01-26	Compositions and methods for improving the tolerance by crop plants of herbicidally active acetanilides
EP0023308B1 (fr)	1982-12-22	N-acyl-pipéridonecétals, procédé pour leur préparation et leur utilisation comme antidotes pour la protection des plantes cultivées contre les dommages causés par les herbicides
EP0008091B1 (fr)	1981-08-12	N-Pyrazolylméthyl-halogénoacétanilides substituées, procédé pour leur préparation ainsi que leur utilisation comme herbicides
EP0023306A1 (fr)	1981-02-04	N-(Alpha-chloropropionyl)-1,2,3,4-tétrahydro-quinaldine, procédé pour sa préparation et son utilisation comme antidote pour la protection des cultures contre les dommages causés par les herbicides
EP0023307A1 (fr)	1981-02-04	N-(alpha-chloropropionyl)-1,2,3,4-tétrahydroisoquinoléine, procédé pour sa préparation et son utilisation comme antidote pour la protection des plantes cultivées contre les dommages causés par les herbicides
EP0069848A2 (fr)	1983-01-19	Ethers alcoyliques substitués d'azolyl-phénoxyphényl, procédé de leur préparation et leur application comme herbicide et régulateur de croissance de plantes
EP0036544A1 (fr)	1981-09-30	Procédé pour la préparation de N-azolylméthyl halogénoacétanilides substitués
EP0023287B1 (fr)	1983-02-09	Antidote pour la protection de plantes cultivées contre des dommages causés par des herbicides
DE2805756A1 (de)	1979-08-16	N-azolylalkyl-aniline sowie verfahren zu ihrer herstellung
DE2922759A1 (de)	1980-12-11	N-oximinoalkyl-anilide, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
DE2842315A1 (de)	1980-04-17	N-(1,2-azolyl)alkyl-halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2938155A1 (de)	1981-04-23	N-acyl-piperidone, verfahren zu deren herstellung und deren verwendung als gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide
DE2931665A1 (de)	1981-02-19	Imidazolyl-enolether, verfahren zu ihrer herstellung und ihre verwendung als fungizide
EP0073880A2 (fr)	1983-03-16	Esters alcoyliques substitués d'azolyl-phénoxyphénoxy acide alcane carbonique, procédé pour leur préparation et leur application herbicide et régulatrice de croissance de plantes
DE3035356A1 (de)	1982-05-06	Heterocyclisch substituierte amide, verfahren zu deren herstellung und deren verwendung als gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide
DE3122175A1 (de)	1982-12-23	Substituierte phenoxyphenoxyalkancarbonsaeure-azolylalkylester, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide und pflanzenwuchsregulatoren
DE3122152A1 (de)	1982-12-23	Substituierte phenoxybenzoesaeure-azolylalkylester, verfahren zu ihrer herstellung und ihre verwendung als herbizide