DE2856651C2 - - Google Patents
Info
- Publication number
- DE2856651C2 DE2856651C2 DE2856651A DE2856651A DE2856651C2 DE 2856651 C2 DE2856651 C2 DE 2856651C2 DE 2856651 A DE2856651 A DE 2856651A DE 2856651 A DE2856651 A DE 2856651A DE 2856651 C2 DE2856651 C2 DE 2856651C2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- active ingredient
- alkyl
- water
- acetamides
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 description 23
- -1 cyclohexen-1-yl Chemical group 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 230000002363 herbicidal effect Effects 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- 240000008042 Zea mays Species 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 235000010469 Glycine max Nutrition 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- POSWICCRDBKBMH-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-one Chemical compound CC1CC(=O)CC(C)(C)C1 POSWICCRDBKBMH-UHFFFAOYSA-N 0.000 description 4
- 241000335053 Beta vulgaris Species 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 235000006008 Brassica napus var napus Nutrition 0.000 description 3
- 240000000385 Brassica napus var. napus Species 0.000 description 3
- 240000008100 Brassica rapa Species 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 241000743985 Alopecurus Species 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 235000021533 Beta vulgaris Nutrition 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 235000011292 Brassica rapa Nutrition 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 235000007244 Zea mays Nutrition 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 150000003997 cyclic ketones Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 241001233957 eudicotyledons Species 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YPMLWHBHSHOUII-UHFFFAOYSA-N 2-chloro-n-(2,4-dimethylpent-2-en-3-yl)-n-(2-methoxyethyl)acetamide Chemical compound COCCN(C(=O)CCl)C(C(C)C)=C(C)C YPMLWHBHSHOUII-UHFFFAOYSA-N 0.000 description 1
- UTISTFQIYWCFMT-UHFFFAOYSA-N 2-chloro-n-methyl-n-(3,3,5-trimethylcyclohexen-1-yl)acetamide Chemical compound CC1CC(N(C)C(=O)CCl)=CC(C)(C)C1 UTISTFQIYWCFMT-UHFFFAOYSA-N 0.000 description 1
- XLMQJWNLZNQANL-UHFFFAOYSA-N 2-chloro-n-methyl-n-(3,5,5-trimethylcyclohexen-1-yl)acetamide Chemical compound CC1CC(C)(C)CC(N(C)C(=O)CCl)=C1 XLMQJWNLZNQANL-UHFFFAOYSA-N 0.000 description 1
- GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 241000404028 Anthemis Species 0.000 description 1
- 235000005637 Brassica campestris Nutrition 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 240000003538 Chamaemelum nobile Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 1
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 1
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 1
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 1
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 1
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 1
- 235000013603 Digitaria ischaemum Nutrition 0.000 description 1
- 241000035632 Digitaria ischaemum Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 239000005508 Dimethachlor Substances 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 235000009193 Lamium purpureum Nutrition 0.000 description 1
- 240000006503 Lamium purpureum Species 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 235000002560 Solanum lycopersicum Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N37/20—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 containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782856651 DE2856651A1 (de) | 1978-12-29 | 1978-12-29 | Alpha -substituierte n-(trimethyl- cycloalkenyl)-n-alkyl-acetamide und deren verwendung in phytotoxischen zubereitungen |
| TR20508A TR20508A (tr) | 1978-12-29 | 1979-12-08 | Ikameli n-(trimetil-sikloalkenil)n-alkilasetamid'ler ve bunlarin fitatoksik mamullerde kullanilmalari |
| CA000342460A CA1135720A (en) | 1978-12-29 | 1979-12-21 | .alpha.-SUBSTITUTED N-(TRIMETHYLCYCLOALKENYL)-N- ALKYLACETAMIDES AND THEIR USE IN PHYTOTOXIC PREPARATIONS |
| BR7908491A BR7908491A (pt) | 1978-12-29 | 1979-12-26 | Compostos de n-(trimetil-cicloalquenil)-n-alquil acetamidas alfa-substituidas,misturas dos mesmos bem como processo para o tratamento seletivo de cultivos de plantas uteis |
| EP79105383A EP0013429B1 (de) | 1978-12-29 | 1979-12-27 | Vorlauf- und Nachlauf-Herbizide, deren aktive Substanz ein N-(Trimethyl-cyclohexen-1-yl)-N-isopropy-alpha-chloracetamid ist |
| DE7979105383T DE2965973D1 (en) | 1978-12-29 | 1979-12-27 | Alpha-substituted n-(trimethyl-cycloalkenyl)-n-alkyl acetamides and their use in phytotoxic compositions |
| DD79218168A DD148288A1 (de) | 1978-12-29 | 1979-12-27 | Verfahren zur selektiven behandlung von nutzpflanzenkulturen |
| BG046084A BG33881A3 (en) | 1978-12-29 | 1979-12-27 | Herbicide means and method for cultural plants treatment |
| IL59050A IL59050A (en) | 1978-12-29 | 1979-12-28 | N-substituted n-(trimethylcycloalkenyl)-acetamides and their use as herbicides |
| US06/108,226 US4319918A (en) | 1978-12-29 | 1979-12-28 | α-Substituted N-(trimethylcycloalkenyl)-N-alkylacetamides and their use in phytotoxic preparations |
| ZA00797057A ZA797057B (en) | 1978-12-29 | 1979-12-28 | Alpha-substituted n-(trimethylcyclo-alkenyl)-n-alkylacetamides and their use in phytotoxic preparations |
| JP17053879A JPS5592351A (en) | 1978-12-29 | 1979-12-28 | Alphaasubstituted nn*trimethyllcycloalkenyl** nnalkyllacetoamides and selective herbicide containing them |
| EG778/78A EG14212A (en) | 1978-12-29 | 1979-12-29 | Alpha-substituted n-(trimethylcycloalkenyl)-n-alkyl acetamides |
| IN1361/CAL/79A IN151526B (en, 2012) | 1978-12-29 | 1979-12-29 | |
| ZM33/80A ZM3380A1 (en) | 1978-12-29 | 1980-03-12 | Alpha-substituted n-(trimethyleyeloalkenyl)-n-alkylacetamides and their use in phytotoxie preparations |
| SU813318799A SU1288182A1 (ru) | 1978-12-29 | 1981-02-12 | " -гaлoгehпpoизboдhыe -зameщehhыx -/tpиmetилциkлoaлkeh-1-ил/aцetamидob,пpoяbляющиe гepбицидhую aktиbhoctь" |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782856651 DE2856651A1 (de) | 1978-12-29 | 1978-12-29 | Alpha -substituierte n-(trimethyl- cycloalkenyl)-n-alkyl-acetamide und deren verwendung in phytotoxischen zubereitungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2856651A1 DE2856651A1 (de) | 1980-07-10 |
| DE2856651C2 true DE2856651C2 (en, 2012) | 1989-06-22 |
Family
ID=6058661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782856651 Granted DE2856651A1 (de) | 1978-12-29 | 1978-12-29 | Alpha -substituierte n-(trimethyl- cycloalkenyl)-n-alkyl-acetamide und deren verwendung in phytotoxischen zubereitungen |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5592351A (en, 2012) |
| DE (1) | DE2856651A1 (en, 2012) |
| SU (1) | SU1288182A1 (en, 2012) |
| ZA (1) | ZA797057B (en, 2012) |
| ZM (1) | ZM3380A1 (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3419050A1 (de) * | 1984-05-22 | 1985-11-28 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Herbizides mittel |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES336244A1 (es) * | 1966-02-01 | 1967-12-16 | Monsanto Co | Procedimiento para preparar una composicion fitotoxica. |
| US3574746A (en) * | 1967-06-05 | 1971-04-13 | Monsanto Co | N-(cycloalken-1-yl) alpha-haloacetamides |
| BE756119R (fr) * | 1969-09-15 | 1971-03-15 | Monsanto Co | Procedes de preparation d'alpha-chloroacetamides, nouveaux produits et compositions phytotoxiques ainsi |
| US4021224A (en) * | 1971-12-09 | 1977-05-03 | Stauffer Chemical Company | Herbicide compositions |
| US3867444A (en) * | 1972-07-17 | 1975-02-18 | Stauffer Chemical Co | Schiff{3 s base dichloroacetamides |
| US3931313A (en) * | 1972-07-17 | 1976-01-06 | Stauffer Chemical Company | Schiff's base dichloroacetamides |
-
1978
- 1978-12-29 DE DE19782856651 patent/DE2856651A1/de active Granted
-
1979
- 1979-12-28 ZA ZA00797057A patent/ZA797057B/xx unknown
- 1979-12-28 JP JP17053879A patent/JPS5592351A/ja active Granted
-
1980
- 1980-03-12 ZM ZM33/80A patent/ZM3380A1/xx unknown
-
1981
- 1981-02-12 SU SU813318799A patent/SU1288182A1/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA797057B (en) | 1981-04-29 |
| ZM3380A1 (en) | 1980-11-21 |
| JPS5592351A (en) | 1980-07-12 |
| SU1288182A1 (ru) | 1987-02-07 |
| JPH0114217B2 (en, 2012) | 1989-03-10 |
| DE2856651A1 (de) | 1980-07-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0036390B1 (de) | Diphenyläther-Harnstoffe mit herbizider Wirkung | |
| EP0028829B1 (de) | Harnstoffe mit cyclischen Substituenten, ihre Herstellung und Verwendung als Herbizide | |
| EP0132512A1 (de) | Verwendung von in 2-Stellung mit (substituierten) Aminogruppen substituierten 4-DL-Alkylester-alpha-alaninyl-6-chlor-s-Triazinen als Herbizide, insbesondere gegen Flughafer | |
| EP0136455A1 (de) | Substituierte Phenylsulfonylguanidin-Derivate | |
| EP0013429B1 (de) | Vorlauf- und Nachlauf-Herbizide, deren aktive Substanz ein N-(Trimethyl-cyclohexen-1-yl)-N-isopropy-alpha-chloracetamid ist | |
| DE2219923C3 (de) | Substituierte O- [Aminosulfonyl] -glykolsäureamide | |
| DE1812497C3 (de) | N-Phosphinothioyl-thiomethyl-carbonyl-piperidine, Verfahren zu ihrer Herstellung und diese enthaltende Mittel | |
| DE2856651C2 (en, 2012) | ||
| DE2044735C3 (de) | Phenylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel | |
| DE2943703A1 (de) | 6h-1,2,4,6-thiatriazin-1,1-dioxide, herbizide, die diese verbindungen enthalten, ihre anwendung als herbizide und verfahren zu ihrer herstellung | |
| EP0153601B1 (de) | 2-Alkoxyaminosulfonylbenzolsulfonyl-harnstoff-Derivate | |
| EP0062254A1 (de) | Substituierte Acetanilide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide | |
| DE2050979C2 (de) | 3-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)-harnstoffverbindungen | |
| EP0148498A1 (de) | Neue Sulfonylguanidin-Derivate | |
| DE2114774C3 (de) | m-(Halogenalkenyloxy)-phenyIharnstoffe, Verfahren zu ihrer Herstellung und sie enthaltende herbizide Mittel | |
| DE1300727B (de) | Verwendung von Dinitroanilinderivaten als selektive Vorauflaufherbizide | |
| DE2163381A1 (de) | Herbizide Komposition | |
| EP0126891B1 (de) | Alpha-alkoxylierte N-(3,3,5-bwz. 3,5,5-Trimethylcyclohexen-1-yl)-N-alkyl- oder -N-allyl-acetamide und deren Verwendung in phytotoxischen Zubereitungen | |
| EP0016731B1 (de) | Meta-Cyanoalkoxy-Phenylharnstoffe mit herbizider Wirkung, deren Herstellung und sie enthaltende Mittel | |
| DE2850902A1 (de) | Neue phenoxy-phenoxi-propionsaeureamide und ihre verwendung als herbizide | |
| DE2940231A1 (de) | (alpha)-substituierte n-(trimethylcycloalkenyl)-n-alkyl-acetamide und deren verwendung in phytotoxischen zubereitungen | |
| DE2803662A1 (de) | Chloracetanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel | |
| DD146540A5 (de) | Herbizides mittel | |
| EP0189800A2 (de) | Thiocyanatomethylthio-Gruppen enthaltende Verbindungen | |
| DE2608473A1 (de) | N-methylcarbanilsaeure- eckige klammer auf 3-(aethoxycarbonylamino)-phenyl eckige klammer zu -ester als baumwollherbizides mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8181 | Inventor (new situation) |
Free format text: BALTRUSCHAT, HELMUT, DR. BELLUT, HANS, DIPL.-CHEM. DR., 4408 DUELMEN, DE SCHNURBUSCH, HORST, DIPL.-CHEM. DR., 4690 HERNE, DE |
|
| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: HUELS AG, 4370 MARL, DE RUHR-STICKSTOFF AG, 4630 B |
|
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8330 | Complete disclaimer |