DE3032259A1 - Herbizide mittel auf der basis von cyclohexan-1,3- dion-derivaten und 3,6-dichlor-2-picolinsaeurederivaten - Google Patents
Herbizide mittel auf der basis von cyclohexan-1,3- dion-derivaten und 3,6-dichlor-2-picolinsaeurederivatenInfo
- Publication number
- DE3032259A1 DE3032259A1 DE19803032259 DE3032259A DE3032259A1 DE 3032259 A1 DE3032259 A1 DE 3032259A1 DE 19803032259 DE19803032259 DE 19803032259 DE 3032259 A DE3032259 A DE 3032259A DE 3032259 A1 DE3032259 A1 DE 3032259A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- methyl
- carbon atoms
- cyclohexane
- phenyl
- 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.)
- Withdrawn
Links
- 239000002253 acid Substances 0.000 title claims description 21
- 239000004009 herbicide Substances 0.000 title claims description 18
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 title claims description 10
- SXDFGRKJVDBFML-UHFFFAOYSA-N 3,6-dichloro-2-methylpyridine Chemical compound CC1=NC(Cl)=CC=C1Cl SXDFGRKJVDBFML-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 63
- -1 methoxy-substituted phenyl Chemical group 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 230000002363 herbicidal effect Effects 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000003863 ammonium salts Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical class OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- JEFHGYSGNIFAEY-UHFFFAOYSA-N 2-[1-(ethoxyamino)butylidene]-5-(2-ethylsulfanylpropyl)cyclohexane-1,3-dione Chemical compound CCONC(CCC)=C1C(=O)CC(CC(C)SCC)CC1=O JEFHGYSGNIFAEY-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- AFZMKBLOQNTBOT-UHFFFAOYSA-N 3,4-dichloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(Cl)=C1Cl AFZMKBLOQNTBOT-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 35
- 239000004480 active ingredient Substances 0.000 description 34
- 150000001408 amides Chemical class 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 18
- 239000003921 oil Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 230000006378 damage Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000004702 methyl esters Chemical class 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 240000002791 Brassica napus Species 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 4
- 241000209219 Hordeum Species 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 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
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 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 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 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 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-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
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 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
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- CSPPKDPQLUUTND-UHFFFAOYSA-N chembl3186232 Chemical compound CCON=C(CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
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- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
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- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
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- WDRGQGLIUAMOOC-UHFFFAOYSA-N 2-benzamidooxyacetic acid Chemical compound OC(=O)CONC(=O)C1=CC=CC=C1 WDRGQGLIUAMOOC-UHFFFAOYSA-N 0.000 description 1
- QMTFTRRIGOCPAU-UHFFFAOYSA-N 2-ethoxy-3,3,5-trimethyl-2h-1-benzofuran Chemical compound C1=C(C)C=C2C(C)(C)C(OCC)OC2=C1 QMTFTRRIGOCPAU-UHFFFAOYSA-N 0.000 description 1
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
- FYEWDLAVQKIKQE-UHFFFAOYSA-N 2-methyl-4-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazinane-3,5-dione Chemical compound O=C1N(C)OCC(=O)N1C1=CC=CC(C(F)(F)F)=C1 FYEWDLAVQKIKQE-UHFFFAOYSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical compound C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
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- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000009736 wetting Methods 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803032259 DE3032259A1 (de) | 1980-08-27 | 1980-08-27 | Herbizide mittel auf der basis von cyclohexan-1,3- dion-derivaten und 3,6-dichlor-2-picolinsaeurederivaten |
| GR65477A GR81312B (enExample) | 1980-08-27 | 1981-07-10 | |
| AT81105561T ATE7839T1 (de) | 1980-08-27 | 1981-07-15 | Herbizide mittel auf der basis von cyclohexan-1,3-dion-derivaten und 3,6-dichlor-2picolins[urederivaten. |
| DE8181105561T DE3164152D1 (en) | 1980-08-27 | 1981-07-15 | Herbicidal agents on the the basis of cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic-acid derivatives |
| EP81105561A EP0046503B1 (de) | 1980-08-27 | 1981-07-15 | Herbizide Mittel auf der Basis von Cyclohexan-1,3-dion-derivaten und 3,6-Dichlor-2-picolinsäurederivaten |
| IL63507A IL63507A0 (en) | 1980-08-27 | 1981-08-05 | Herbicides based on cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic acid derivatives |
| CA000383564A CA1169263A (en) | 1980-08-27 | 1981-08-10 | Herbicides based on cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic acid derivatives |
| US06/294,238 US4427440A (en) | 1980-08-27 | 1981-08-19 | Herbicides based on cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic acid derivatives |
| AR286508A AR231897A1 (es) | 1980-08-27 | 1981-08-21 | Composicion herbicida a base de 2-(1-(alcoxialquiliden)-5-(alquiltioalquil)-ciclohexan-1,3-diona y acido 3,6 dicloro-2-picolinico |
| IE1956/81A IE51574B1 (en) | 1980-08-27 | 1981-08-26 | Herbicides based on cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic acid derivatives |
| JP56132653A JPS5772902A (en) | 1980-08-27 | 1981-08-26 | Herbicide based on cyclohexane-1,3-dione derivative and 3,6-dichloro-2-picolinic acid derivative |
| HU812470A HU188552B (en) | 1980-08-27 | 1981-08-26 | Herbicide compositions containing cyclohexane-1,3-dione derivatives and 3,6-dichloro-picolinic acid derivative simultaneously |
| DK377781A DK377781A (da) | 1980-08-27 | 1981-08-26 | Herbicide midler paa basis af et cyclohexan-1,3-dion-derivat og et 3,6-dichlor-2-picolinsyre-derivat |
| AU74631/81A AU545010B2 (en) | 1980-08-27 | 1981-08-26 | Herbicides based on cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic acid derivatives |
| ZA815901A ZA815901B (en) | 1980-08-27 | 1981-08-26 | Herbicides based on cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic acid derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803032259 DE3032259A1 (de) | 1980-08-27 | 1980-08-27 | Herbizide mittel auf der basis von cyclohexan-1,3- dion-derivaten und 3,6-dichlor-2-picolinsaeurederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3032259A1 true DE3032259A1 (de) | 1982-04-08 |
Family
ID=6110495
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803032259 Withdrawn DE3032259A1 (de) | 1980-08-27 | 1980-08-27 | Herbizide mittel auf der basis von cyclohexan-1,3- dion-derivaten und 3,6-dichlor-2-picolinsaeurederivaten |
| DE8181105561T Expired DE3164152D1 (en) | 1980-08-27 | 1981-07-15 | Herbicidal agents on the the basis of cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic-acid derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181105561T Expired DE3164152D1 (en) | 1980-08-27 | 1981-07-15 | Herbicidal agents on the the basis of cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic-acid derivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4427440A (enExample) |
| EP (1) | EP0046503B1 (enExample) |
| JP (1) | JPS5772902A (enExample) |
| AR (1) | AR231897A1 (enExample) |
| AT (1) | ATE7839T1 (enExample) |
| AU (1) | AU545010B2 (enExample) |
| CA (1) | CA1169263A (enExample) |
| DE (2) | DE3032259A1 (enExample) |
| DK (1) | DK377781A (enExample) |
| GR (1) | GR81312B (enExample) |
| HU (1) | HU188552B (enExample) |
| IE (1) | IE51574B1 (enExample) |
| IL (1) | IL63507A0 (enExample) |
| ZA (1) | ZA815901B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3219315A1 (de) * | 1982-05-22 | 1983-11-24 | Basf Ag, 6700 Ludwigshafen | Cyclohexan-1,3-dion-derivate |
| US4631081A (en) * | 1982-09-29 | 1986-12-23 | Ici Australia Limited | Herbicidal cyclohexane-1,3-dione derivatives |
| DE3332272A1 (de) * | 1983-09-07 | 1985-03-21 | Bayer Ag, 5090 Leverkusen | Herbizide mittel enthaltend metribuzin in kombination mit pyridincarbonsaeureamiden |
| US4626276A (en) * | 1984-06-11 | 1986-12-02 | Chevron Research Company | Herbicidal trans-2-[(3-chloroallyloxyimino)alkyl]-5-(substitutedsulfinylalkyl)-cyclohexane-1,3-diones and derivatives thereof |
| DE3433541A1 (de) * | 1984-09-13 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Herbizide mittel enthaltend photosynthesehemmer-herbizide in kombination mit carbamat-derivaten |
| ATE93680T1 (de) * | 1985-12-30 | 1993-09-15 | Stauffer Chemical Co | Synergistische, herbizide kombinationen und verfahren zur anwendung. |
| PL204338B1 (pl) * | 1999-10-14 | 2010-01-29 | Basf Ag | Synergiczny środek chwastobójczy i sposób zwalczania niepożądanych roślin |
| RU2213451C1 (ru) * | 2002-02-19 | 2003-10-10 | Закрытое акционерное общество "Щелково Агрохим" | Гербицидный состав |
| RU2320170C1 (ru) * | 2006-07-19 | 2008-03-27 | Государственное учреждение "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством" (НИТИГ) | Гербицидный состав |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1228848B (de) | 1963-03-25 | 1966-11-17 | Dow Chemical Co | Verwendung von 3, 6-Dichlor-2-picolinsaeureverbindungen als Totalherbizid |
| JPS5931481B2 (ja) * | 1974-09-20 | 1984-08-02 | 日本曹達株式会社 | シクロヘキサンジオン系除草剤組成物 |
| IL54560A (en) | 1977-05-23 | 1981-06-29 | Nippon Soda Co | Substituted 2-aminoalkylidene-1,3-cyclohexanediones,their preparation and their use as herbicides |
-
1980
- 1980-08-27 DE DE19803032259 patent/DE3032259A1/de not_active Withdrawn
-
1981
- 1981-07-10 GR GR65477A patent/GR81312B/el unknown
- 1981-07-15 AT AT81105561T patent/ATE7839T1/de not_active IP Right Cessation
- 1981-07-15 DE DE8181105561T patent/DE3164152D1/de not_active Expired
- 1981-07-15 EP EP81105561A patent/EP0046503B1/de not_active Expired
- 1981-08-05 IL IL63507A patent/IL63507A0/xx not_active IP Right Cessation
- 1981-08-10 CA CA000383564A patent/CA1169263A/en not_active Expired
- 1981-08-19 US US06/294,238 patent/US4427440A/en not_active Expired - Fee Related
- 1981-08-21 AR AR286508A patent/AR231897A1/es active
- 1981-08-26 IE IE1956/81A patent/IE51574B1/en unknown
- 1981-08-26 AU AU74631/81A patent/AU545010B2/en not_active Ceased
- 1981-08-26 ZA ZA815901A patent/ZA815901B/xx unknown
- 1981-08-26 HU HU812470A patent/HU188552B/hu not_active IP Right Cessation
- 1981-08-26 JP JP56132653A patent/JPS5772902A/ja active Pending
- 1981-08-26 DK DK377781A patent/DK377781A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK377781A (da) | 1982-02-28 |
| JPS5772902A (en) | 1982-05-07 |
| IE811956L (en) | 1982-02-27 |
| CA1169263A (en) | 1984-06-19 |
| AU545010B2 (en) | 1985-06-27 |
| GR81312B (enExample) | 1984-12-11 |
| HU188552B (en) | 1986-04-28 |
| IE51574B1 (en) | 1987-01-21 |
| ATE7839T1 (de) | 1984-06-15 |
| AR231897A1 (es) | 1985-04-30 |
| EP0046503B1 (de) | 1984-06-13 |
| US4427440A (en) | 1984-01-24 |
| AU7463181A (en) | 1982-03-04 |
| ZA815901B (en) | 1982-09-29 |
| DE3164152D1 (en) | 1984-07-19 |
| IL63507A0 (en) | 1981-11-30 |
| EP0046503A1 (de) | 1982-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |