DD145052A5 - Herbizide mittel - Google Patents

Herbizide mittel Download PDF

Info

Publication number: DD145052A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; unbranched; methyl; acetanilide; herbicidal
Prior art date: 1978-07-27

Application number

DD79214610A

Other languages

German (de)

English (en)

Inventor

Karl Eicken

Wolfgang Rohr

Hans J Pander

Bruno Wuerzer

Original Assignee

Basf 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.)

1978-07-27

Filing date

1979-07-25

Publication date

1980-11-19

1979-07-25 Application filed by Basf Ag filed Critical Basf Ag

1980-11-19 Publication of DD145052A5 publication Critical patent/DD145052A5/de

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 48
239000004009 herbicide Substances 0.000 title description 8
-1 acetanilide tetrahydro-1,3-oxazine Chemical compound 0.000 claims abstract description 45
239000003795 chemical substances by application Substances 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 46
230000003042 antagnostic effect Effects 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 15
UFTHEDBYLPFRDP-UHFFFAOYSA-N 5,6-dihydro-2h-oxazine Chemical compound C1CC=CNO1 UFTHEDBYLPFRDP-UHFFFAOYSA-N 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Chemical group 0.000 claims description 4
150000003851 azoles Chemical class 0.000 claims description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 2
239000004480 active ingredient Substances 0.000 abstract description 25
229960001413 acetanilide Drugs 0.000 abstract description 19
239000000203 mixture Substances 0.000 abstract description 18
150000008061 acetanilides Chemical class 0.000 abstract description 17
FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract description 17
240000008042 Zea mays Species 0.000 abstract description 16
239000005557 antagonist Substances 0.000 abstract description 13
LQPOOAJESJYDLS-UHFFFAOYSA-N 1,3-oxazinane Chemical compound C1CNCOC1 LQPOOAJESJYDLS-UHFFFAOYSA-N 0.000 abstract description 12
235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 11
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 5
235000013339 cereals Nutrition 0.000 abstract description 5
235000005822 corn Nutrition 0.000 abstract description 5
230000008635 plant growth Effects 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 29
150000001875 compounds Chemical class 0.000 description 20
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
230000006378 damage Effects 0.000 description 15
239000003921 oil Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000006185 dispersion Substances 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000000729 antidote Substances 0.000 description 7
150000002431 hydrogen Chemical group 0.000 description 7
238000009331 sowing Methods 0.000 description 7
238000012360 testing method Methods 0.000 description 7
241000192043 Echinochloa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
244000038559 crop plants Species 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
235000009973 maize Nutrition 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000011282 treatment Methods 0.000 description 5
241000743985 Alopecurus Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
244000042664 Matricaria chamomilla Species 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
241000209140 Triticum Species 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
235000007244 Zea mays Nutrition 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
240000006122 Chenopodium album Species 0.000 description 3
244000058871 Echinochloa crus-galli Species 0.000 description 3
235000007232 Matricaria chamomilla Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
150000002790 naphthalenes Chemical class 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000002689 soil Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
150000003852 triazoles Chemical class 0.000 description 3
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
BDXJANJAHYKTMI-UHFFFAOYSA-N 2,3,4,5-tetramethyl-1h-pyrrole Chemical compound CC=1NC(C)=C(C)C=1C BDXJANJAHYKTMI-UHFFFAOYSA-N 0.000 description 2
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
ZTLDKLKBIJBLJK-UHFFFAOYSA-N 2-chloro-n-[(4,5-dichloroimidazol-1-yl)methyl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1C(Cl)=C(Cl)N=C1 ZTLDKLKBIJBLJK-UHFFFAOYSA-N 0.000 description 2
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 2
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
QAJJXHRQPLATMK-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole Chemical compound ClC=1N=CNC=1Cl QAJJXHRQPLATMK-UHFFFAOYSA-N 0.000 description 2
XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
241001621841 Alopecurus myosuroides Species 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
235000009344 Chenopodium album Nutrition 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 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
235000017945 Matricaria Nutrition 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
235000011999 Panicum crusgalli Nutrition 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
229920001807 Urea-formaldehyde Polymers 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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239000007859 condensation product Substances 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical class NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
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239000002270 dispersing agent Substances 0.000 description 2
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ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
239000003864 humus Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
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 2
STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
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235000010446 mineral oil Nutrition 0.000 description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
239000006072 paste Substances 0.000 description 2
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239000000725 suspension Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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235000013311 vegetables Nutrition 0.000 description 2
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XVFAWYIDDRHPNV-UHFFFAOYSA-N 1-(3,5-dimethyl-1h-pyrazol-4-yl)ethanone Chemical compound CC(=O)C=1C(C)=NNC=1C XVFAWYIDDRHPNV-UHFFFAOYSA-N 0.000 description 1
PHYOGGZZDVVPBS-UHFFFAOYSA-N 1-(3,5-dimethyl-1h-pyrazol-4-yl)propan-1-one Chemical compound CCC(=O)C=1C(C)=NNC=1C PHYOGGZZDVVPBS-UHFFFAOYSA-N 0.000 description 1
FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
NUGZBVBZIDWZAD-UHFFFAOYSA-N 1h-pyrazole-4-carbonitrile Chemical compound N#CC=1C=NNC=1 NUGZBVBZIDWZAD-UHFFFAOYSA-N 0.000 description 1
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JNTFFNKMQMJJQZ-UHFFFAOYSA-N 3,5-dichloro-1h-1,2,4-triazole Chemical compound ClC1=NNC(Cl)=N1 JNTFFNKMQMJJQZ-UHFFFAOYSA-N 0.000 description 1
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SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 description 1
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238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
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235000013312 flour Nutrition 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
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UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
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235000019253 formic acid Nutrition 0.000 description 1
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150000008282 halocarbons Chemical class 0.000 description 1
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239000006028 limestone Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
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229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
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125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
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150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
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150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
QZHDEAJFRJCDMF-UHFFFAOYSA-N perfluorohexanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
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239000002798 polar solvent Substances 0.000 description 1
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238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004904 shortening Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
125000005624 silicic acid group Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
- 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
- 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
- C07D231/18—One oxygen or sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Toxicology (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (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)
Plural Heterocyclic Compounds (AREA)

DD79214610A 1978-07-27 1979-07-25 Herbizide mittel DD145052A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782832890 DE2832890A1 (de)	1978-07-27	1978-07-27	Herbizide mittel

Publications (1)

Publication Number	Publication Date
DD145052A5 true DD145052A5 (de)	1980-11-19

Family

ID=6045475

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79214610A DD145052A5 (de)	1978-07-27	1979-07-25	Herbizide mittel

Country Status (23)

Country	Link
US (1)	US4295875A (fr)
EP (1)	EP0007588B1 (fr)
JP (1)	JPS5520768A (fr)
AR (1)	AR230274A1 (fr)
AT (1)	ATE66T1 (fr)
AU (1)	AU525577B2 (fr)
BR (1)	BR7904768A (fr)
CA (1)	CA1133902A (fr)
CS (1)	CS213391B2 (fr)
DD (1)	DD145052A5 (fr)
DE (2)	DE2832890A1 (fr)
DK (1)	DK314979A (fr)
ES (1)	ES482839A1 (fr)
GR (1)	GR66644B (fr)
HU (1)	HU181851B (fr)
IL (1)	IL57800A (fr)
MA (1)	MA18536A1 (fr)
NZ (1)	NZ191129A (fr)
PL (1)	PL121169B2 (fr)
PT (1)	PT69976A (fr)
RO (1)	RO76976A (fr)
SU (1)	SU1101173A3 (fr)
ZA (1)	ZA793862B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2948535A1 (de) *	1979-12-03	1981-06-25	Basf Ag, 6700 Ludwigshafen	Dichloracetamide, herbizide mittel, die acetanilide als herbizide wirkstoffe und diese dichloracetamide als antagonistische mittel enthalten, sowie ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses
DE3119077A1 (de) *	1981-05-14	1982-12-02	Basf Ag, 6700 Ludwigshafen	Heterocyclische dihalogenacetmide, verfahren zu ihrer herstellung und herbizide mittel, die acetanilide als herbizide wirkstoffe und diese dihalogenacetamine als antagonistische mittel enthalten
US4601745A (en) *	1983-12-12	1986-07-22	Ciba-Geigy Corporation	Composition for the protection of cultivated plants against the phytotoxic action of herbicides
US4618361A (en) *	1983-12-12	1986-10-21	Ciba-Geigy Corporation	Acylamides and compositions for the protection of cultivated plants against the phytotoxic action of herbicides
US5514678A (en) *	1992-03-26	1996-05-07	E. I. Du Pont De Nemours And Company	Arthropodicidal 1,2,4-triazinyl amides

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3719466A (en) *	1970-04-16	1973-03-06	Gulf Research Development Co	Protection of wheat and grain sorghum from herbicidal injury
CA1174865A (fr) *	1971-04-16	1984-09-25	Ferenc M. Pallos	Herbicides a base de thiolcarbamate contenant un antidote azote
FR2137005B1 (fr) *	1971-05-11	1974-08-23	Delalande Sa
US4021224A (en) *	1971-12-09	1977-05-03	Stauffer Chemical Company	Herbicide compositions
US3989503A (en) *	1972-10-13	1976-11-02	Stauffer Chemical Company	Herbicidal antidote compositions with substituted oxazolidines and thiazolidines
CH574207A5 (fr) *	1973-01-25	1976-04-15	Ciba Geigy Ag
FR2310348A1 (fr) *	1975-05-07	1976-12-03	Ugine Kuhlmann	Nouveaux derives heterocycliques antidotes contre herbicides
DE2648008C3 (de) *	1976-10-23	1980-09-04	Basf Ag, 6700 Ludwigshafen	Acetanilide

1978
- 1978-06-06 GR GR59284A patent/GR66644B/el unknown
- 1978-07-27 DE DE19782832890 patent/DE2832890A1/de active Pending
1979
- 1979-07-10 CA CA331,488A patent/CA1133902A/fr not_active Expired
- 1979-07-13 IL IL57800A patent/IL57800A/xx unknown
- 1979-07-20 AT AT79102556T patent/ATE66T1/de not_active IP Right Cessation
- 1979-07-20 EP EP79102556A patent/EP0007588B1/fr not_active Expired
- 1979-07-20 MA MA18733A patent/MA18536A1/fr unknown
- 1979-07-20 DE DE7979102556T patent/DE2960349D1/de not_active Expired
- 1979-07-25 AU AU49209/79A patent/AU525577B2/en not_active Ceased
- 1979-07-25 BR BR7904768A patent/BR7904768A/pt unknown
- 1979-07-25 DD DD79214610A patent/DD145052A5/de unknown
- 1979-07-25 PT PT69976A patent/PT69976A/pt unknown
- 1979-07-25 AR AR277462A patent/AR230274A1/es active
- 1979-07-25 PL PL1979217380A patent/PL121169B2/pl unknown
- 1979-07-25 RO RO7998267A patent/RO76976A/fr unknown
- 1979-07-26 JP JP9433779A patent/JPS5520768A/ja active Pending
- 1979-07-26 DK DK314979A patent/DK314979A/da not_active Application Discontinuation
- 1979-07-26 ES ES482839A patent/ES482839A1/es not_active Expired
- 1979-07-26 HU HU79BA3825A patent/HU181851B/hu unknown
- 1979-07-26 NZ NZ191129A patent/NZ191129A/xx unknown
- 1979-07-26 CS CS795201A patent/CS213391B2/cs unknown
- 1979-07-27 ZA ZA00793862A patent/ZA793862B/xx unknown
1980
- 1980-03-24 US US06/132,986 patent/US4295875A/en not_active Expired - Lifetime
1981
- 1981-01-09 SU SU813228096A patent/SU1101173A3/ru active

Also Published As

Publication number	Publication date
PL121169B2 (en)	1982-04-30
PT69976A (en)	1979-08-01
MA18536A1 (fr)	1980-04-01
PL217380A2 (fr)	1980-04-21
ES482839A1 (es)	1980-04-16
DK314979A (da)	1980-01-28
HU181851B (en)	1983-11-28
CS213391B2 (en)	1982-04-09
IL57800A (en)	1982-08-31
ATE66T1 (de)	1981-05-15
NZ191129A (en)	1981-10-19
SU1101173A3 (ru)	1984-06-30
JPS5520768A (en)	1980-02-14
EP0007588A1 (fr)	1980-02-06
EP0007588B1 (fr)	1981-05-13
BR7904768A (pt)	1980-04-22
CA1133902A (fr)	1982-10-19
AU4920979A (en)	1980-01-31
AR230274A1 (es)	1984-03-01
ZA793862B (en)	1980-08-27
DE2832890A1 (de)	1980-02-14
AU525577B2 (en)	1982-11-11
RO76976A (fr)	1981-08-30
US4295875A (en)	1981-10-20
DE2960349D1 (en)	1981-08-20
GR66644B (fr)	1981-04-03
IL57800A0 (en)	1979-11-30

Publication	Publication Date	Title
EP0007990B1 (fr)	1981-03-25	Pyrazol-éthers, leur procédé de préparation et herbicides les contenant
DE2648008A1 (de)	1978-05-03	Acetanilide
EP0031042B1 (fr)	1983-01-26	Dérivés de N-dichloroacétyldiazabicyclo, procédé pour leur préparation, herbicides contenant des acétanilides comme herbicides et ces dérives de N-dichloroacétyldiazabicyclo comme antidotes et leur utilisation pour la lutte contre la végétation indésirable
EP0011693A1 (fr)	1980-06-11	N-hétérocycles N-substitués par trifluorométhane-sulfonylaminophényle, leur préparation, compositions les contenant et leur utilisation pour la régulation de la croissance des plantes
EP0071794A1 (fr)	1983-02-16	Dérivés de l'acide 5-amino-1-phényl-pyrazol-4-carboxylique, leur procédé de préparation et leur application comme herbicides
EP0003805A1 (fr)	1979-09-05	Pyridazones et compositions herbicides les contenant
EP0008649B1 (fr)	1982-01-27	Agents herbicides à base d'acétanilides et de la N-isopropyl-N-propargyl-dichloracétamide et procédé de lutte sélective contre la croissance de plantes indésirables
EP0065724B1 (fr)	1984-08-08	Dihalogénoacétamides, procédé pour leur préparation et herbicides contenant acétanilides comme herbicides et dihalogénoacétamides comme antidotes
EP0135838B1 (fr)	1990-04-18	3-Phényl-4-méthoxy carbonylepyrazoles, leur procédé de préparation et leur utilisation dans la lutte contre la croissance de plantes indésirables
EP0368212A2 (fr)	1990-05-16	Agents herbicides, contenant des dérivés des acides 2-(4-hétéroaryloxy)- ou 2-(4-aryloxy)-phénoxy-acétiques ou -propioniques et/ou des dérivés de la cyclohexénone comme matières actives et des dérivés du naphtalène comme antidotes
EP0007588B1 (fr)	1981-05-13	Tétrahydro-1,3-oxazines, compositions herbicides contenant des acétanilides comme agents herbicides et ces tétrahydro-1,3-oxazines comme agents antagonistes et leur application pour la lutte contre la croissance indésirable de plantes
EP0013873B1 (fr)	1982-01-20	Anilides de l'acide N-azolyl acétique, procédé pour leur préparation et leur utilisation comme herbicides
EP0001751A1 (fr)	1979-05-16	Dérivés de N-(imidazolylméthyle)-acétanilide, leur application comme herbicides et procédé pour combattre la croissance de plantes indésirables
EP0007575B1 (fr)	1981-12-23	Compositions herbicides à base d'acétanilides et leur application dans la lutte contre la végétation indésirable
EP0065189B1 (fr)	1986-09-24	Dihalogénoacétamides hétérocycliques, procédé pour leur préparation et herbicide qui contient des acétanilides comme agents herbicides et ce dihalogénoacétamide comme agent antagoniste
DD145050A5 (de)	1980-11-19	Herbizide mittel
DE3600903A1 (de)	1987-07-16	Optisch aktive diazabicycloalkanderivate, ein verfahren zu ihrer herstellung und ihre verwendung zum schutz von kulturpflanzen vor der phytotoxischen wirkung von herbiziden
EP0087048B1 (fr)	1985-04-17	Oximinoacétamilides substituées, leur méthode de préparation ainsi que leur utilisation comme pesticide
EP0009555A1 (fr)	1980-04-16	Agents herbicides à base d'un thiolcarbamate contenant un haloacylamide comme antagoniste et leur utilisation dans un procédé de lutte sélective contre la croissance de plantes indésirables
EP0268295A2 (fr)	1988-05-25	N-Arylsulfonyl-N'-pyrimidyl-(triazinyl)urées
EP0445069A1 (fr)	1991-09-04	Composés hétérocycliques
EP0399394A1 (fr)	1990-11-28	Azolylméthyl-8 quinoléines
DE2843869A1 (de)	1980-04-24	Acetanilide
CS209463B2 (cs)	1981-12-31	Herbicidní prostředek