IE51574B1 - Herbicides based on cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic acid derivatives - Google Patents
Herbicides based on cyclohexane-1,3-dione derivatives and 3,6-dichloro-2-picolinic acid derivativesInfo
- Publication number
- IE51574B1 IE51574B1 IE1956/81A IE195681A IE51574B1 IE 51574 B1 IE51574 B1 IE 51574B1 IE 1956/81 A IE1956/81 A IE 1956/81A IE 195681 A IE195681 A IE 195681A IE 51574 B1 IE51574 B1 IE 51574B1
- Authority
- IE
- Ireland
- Prior art keywords
- carbon atoms
- formula
- acid
- alkyl
- salts
- Prior art date
Links
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000004009 herbicide Substances 0.000 title abstract description 17
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical class OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 title abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- -1 benzylsubstituted ammonium Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052751 metal Chemical class 0.000 claims description 8
- 239000002184 metal Chemical class 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229940081066 picolinic acid Drugs 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 abstract description 5
- 239000004480 active ingredient Substances 0.000 description 28
- 150000002148 esters Chemical class 0.000 description 27
- 150000001408 amides Chemical class 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 18
- 239000003921 oil Substances 0.000 description 12
- 230000006378 damage Effects 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 5
- 244000038559 crop plants Species 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000002747 voluntary effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 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
- 239000004615 ingredient Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 229940057054 1,3-dimethylurea Drugs 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
- 241000335053 Beta vulgaris Species 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 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
- 241000192043 Echinochloa Species 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
- 241000209504 Poaceae Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- CSPPKDPQLUUTND-UHFFFAOYSA-N chembl3186232 Chemical class 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
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 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
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 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
- 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
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- AZJDTZGAPLVMTK-UHFFFAOYSA-N (2-ethoxy-3,3-dimethyl-2H-1-benzofuran-5-yl)methyl-methylsulfamic acid Chemical compound C1=C(CN(C)S(O)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 AZJDTZGAPLVMTK-UHFFFAOYSA-N 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 1
- 239000002794 2,4-DB Substances 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- KGKGSIUWJCAFPX-UHFFFAOYSA-N 2,6-dichlorothiobenzamide Chemical compound NC(=S)C1=C(Cl)C=CC=C1Cl KGKGSIUWJCAFPX-UHFFFAOYSA-N 0.000 description 1
- QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 1
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- TVYKPDXUGWDUJO-UHFFFAOYSA-N 2-N,4-N-diethyl-6-methoxy-1,3,5-triazine-2,4-diamine 6-methoxy-2-N,4-N-di(propan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound COC1=NC(=NC(=N1)NC(C)C)NC(C)C.COC1=NC(=NC(=N1)NCC)NCC TVYKPDXUGWDUJO-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
- KQMICYCEDQXQRA-UHFFFAOYSA-N 2-cyclohexyl-4,5-dimethoxypyridazin-3-one 4,5-dimethoxy-2-phenylpyridazin-3-one 4,5-dimethoxy-2-[3-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound COC=1C(N(N=CC1OC)C1=CC(=CC=C1)C(F)(F)F)=O.COC=1C(N(N=CC1OC)C1CCCCC1)=O.COC=1C(N(N=CC1OC)C1=CC=CC=C1)=O KQMICYCEDQXQRA-UHFFFAOYSA-N 0.000 description 1
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- 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 class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
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- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
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- KRJXZNYCDUNVKJ-UHFFFAOYSA-N ethyl 2-methylidene-4-[4-(trifluoromethyl)phenoxy]pentanoate methyl 2-(N-benzoyl-3-chloro-4-fluoroanilino)propanoate propan-2-yl 2-(N-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound FC(C1=CC=C(OC(CC(=C)C(=O)OCC)C)C=C1)(F)F.C(C1=CC=CC=C1)(=O)N(C(C(=O)OC(C)C)C)C1=CC(=C(C=C1)F)Cl.C(C1=CC=CC=C1)(=O)N(C(C(=O)OC)C)C1=CC(=C(C=C1)F)Cl KRJXZNYCDUNVKJ-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- NEZZENXMNNWRLE-UHFFFAOYSA-N n-(4-chlorophenyl)-n-(dimethylcarbamoyl)benzamide Chemical compound C=1C=C(Cl)C=CC=1N(C(=O)N(C)C)C(=O)C1=CC=CC=C1 NEZZENXMNNWRLE-UHFFFAOYSA-N 0.000 description 1
- QHLFJSMAWAWVRU-UHFFFAOYSA-N n-(5-chloro-4-methyl-1,3-thiazol-2-yl)propanamide Chemical compound CCC(=O)NC1=NC(C)=C(Cl)S1 QHLFJSMAWAWVRU-UHFFFAOYSA-N 0.000 description 1
- HLWWUAGXWCWAKG-UHFFFAOYSA-N n-ethyl-1,3,5-triazin-2-amine Chemical group CCNC1=NC=NC=N1 HLWWUAGXWCWAKG-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 101150032584 oxy-4 gene Proteins 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 150000003378 silver Chemical class 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
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 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
- 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
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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)
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE811956L IE811956L (en) | 1982-02-27 |
| IE51574B1 true IE51574B1 (en) | 1987-01-21 |
Family
ID=6110495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4427440A (en:Method) |
| EP (1) | EP0046503B1 (en:Method) |
| JP (1) | JPS5772902A (en:Method) |
| AR (1) | AR231897A1 (en:Method) |
| AT (1) | ATE7839T1 (en:Method) |
| AU (1) | AU545010B2 (en:Method) |
| CA (1) | CA1169263A (en:Method) |
| DE (2) | DE3032259A1 (en:Method) |
| DK (1) | DK377781A (en:Method) |
| GR (1) | GR81312B (en:Method) |
| HU (1) | HU188552B (en:Method) |
| IE (1) | IE51574B1 (en:Method) |
| IL (1) | IL63507A0 (en:Method) |
| ZA (1) | ZA815901B (en:Method) |
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 |
| ES2058417T3 (es) * | 1985-12-30 | 1994-11-01 | Stauffer Chemical Co | Combinaciones herbicidas sinergisticas y metodo de aplicacion. |
| EA022145B1 (ru) * | 1999-10-14 | 2015-11-30 | Басф Се | Синергетические гербицидные композиции и способы их применения |
| 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 |
| US4249937A (en) | 1977-05-23 | 1981-02-10 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
-
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 EP EP81105561A patent/EP0046503B1/de not_active Expired
- 1981-07-15 AT AT81105561T patent/ATE7839T1/de not_active IP Right Cessation
- 1981-07-15 DE DE8181105561T patent/DE3164152D1/de not_active Expired
- 1981-08-05 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 JP JP56132653A patent/JPS5772902A/ja active Pending
- 1981-08-26 DK DK377781A patent/DK377781A/da not_active Application Discontinuation
- 1981-08-26 IE IE1956/81A patent/IE51574B1/en unknown
- 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 AU AU74631/81A patent/AU545010B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ZA815901B (en) | 1982-09-29 |
| DE3164152D1 (en) | 1984-07-19 |
| AR231897A1 (es) | 1985-04-30 |
| DE3032259A1 (de) | 1982-04-08 |
| JPS5772902A (en) | 1982-05-07 |
| EP0046503B1 (de) | 1984-06-13 |
| HU188552B (en) | 1986-04-28 |
| EP0046503A1 (de) | 1982-03-03 |
| ATE7839T1 (de) | 1984-06-15 |
| DK377781A (da) | 1982-02-28 |
| CA1169263A (en) | 1984-06-19 |
| AU545010B2 (en) | 1985-06-27 |
| AU7463181A (en) | 1982-03-04 |
| IE811956L (en) | 1982-02-27 |
| GR81312B (en:Method) | 1984-12-11 |
| US4427440A (en) | 1984-01-24 |
| IL63507A0 (en) | 1981-11-30 |
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