GB1576508A - 4,5 - dichloroimidazole derivatives and their use as plant protection agents - Google Patents
4,5 - dichloroimidazole derivatives and their use as plant protection agents Download PDFInfo
- Publication number
- GB1576508A GB1576508A GB42078/77A GB4207877A GB1576508A GB 1576508 A GB1576508 A GB 1576508A GB 42078/77 A GB42078/77 A GB 42078/77A GB 4207877 A GB4207877 A GB 4207877A GB 1576508 A GB1576508 A GB 1576508A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- imidazole
- dichloro
- alkyl
- carboxylic acid
- 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
- QAJJXHRQPLATMK-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole Chemical class ClC=1N=CNC=1Cl QAJJXHRQPLATMK-UHFFFAOYSA-N 0.000 title claims description 13
- 239000011814 protection agent Substances 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 82
- -1 alkali metal salt Chemical class 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 241000196324 Embryophyta Species 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 31
- 239000003085 diluting agent Substances 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- IXMKNMGPLCJFEC-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole-2-carboxylic acid Chemical class OC(=O)C1=NC(Cl)=C(Cl)N1 IXMKNMGPLCJFEC-UHFFFAOYSA-N 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 241000238631 Hexapoda Species 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 230000006378 damage Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 230000012010 growth Effects 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- POSXJXNJTWKUGW-UHFFFAOYSA-N 4,5-dichloro-2-(dichloromethylidene)imidazole Chemical compound ClC(Cl)=C1N=C(Cl)C(Cl)=N1 POSXJXNJTWKUGW-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- JSDKSPDWWXDALY-UHFFFAOYSA-N ethoxymethyl 4,5-dichloro-1H-imidazole-2-carboxylate Chemical compound C(C)OCOC(=O)C=1NC(=C(N=1)Cl)Cl JSDKSPDWWXDALY-UHFFFAOYSA-N 0.000 description 12
- KSLLYIVFPUJDMX-UHFFFAOYSA-N 4,5-dichloro-2-(trichloromethyl)-1h-imidazole Chemical compound ClC=1N=C(C(Cl)(Cl)Cl)NC=1Cl KSLLYIVFPUJDMX-UHFFFAOYSA-N 0.000 description 10
- 125000003963 dichloro group Chemical group Cl* 0.000 description 10
- BPNNULHRWUWMFE-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole-2-carbonitrile Chemical compound ClC=1N=C(C#N)NC=1Cl BPNNULHRWUWMFE-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 244000075850 Avena orientalis Species 0.000 description 5
- 244000062793 Sorghum vulgare Species 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
- GCDQPMGGTPNOAX-UHFFFAOYSA-N 4,5-dichloro-1-(ethoxymethyl)imidazole-2-carbonitrile Chemical compound CCOCN1C(Cl)=C(Cl)N=C1C#N GCDQPMGGTPNOAX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 241000219146 Gossypium Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229950005499 carbon tetrachloride Drugs 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FDBJLOZBFGDENU-UHFFFAOYSA-N 4,5-dichloro-n-formyl-n-propan-2-yl-1h-imidazole-2-carboxamide Chemical compound CC(C)N(C=O)C(=O)C1=NC(Cl)=C(Cl)N1 FDBJLOZBFGDENU-UHFFFAOYSA-N 0.000 description 3
- LOLXKUPEIGLGAP-UHFFFAOYSA-N 4,5-dichloro-n-propan-2-yl-1h-imidazole-2-carboxamide Chemical compound CC(C)NC(=O)C1=NC(Cl)=C(Cl)N1 LOLXKUPEIGLGAP-UHFFFAOYSA-N 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 235000014716 Eleusine indica Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000748465 Galinsoga Species 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 3
- XUXJHBAJZQREDB-UHFFFAOYSA-N methylbutylamide Natural products CCC(C)C(N)=O XUXJHBAJZQREDB-UHFFFAOYSA-N 0.000 description 3
- KVTGAKFJRLBHLU-UHFFFAOYSA-N n-propan-2-ylformamide Chemical compound CC(C)NC=O KVTGAKFJRLBHLU-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical class OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 description 2
- PHVQRFOAVGUKQP-UHFFFAOYSA-N 4,5-dichloro-1-(methoxymethyl)imidazole-2-carbonitrile Chemical compound COCN1C(Cl)=C(Cl)N=C1C#N PHVQRFOAVGUKQP-UHFFFAOYSA-N 0.000 description 2
- ILZVPHDSQNNZBX-UHFFFAOYSA-N 4,5-dichloro-2-(trifluoromethyl)-1h-imidazole Chemical compound FC(F)(F)C1=NC(Cl)=C(Cl)N1 ILZVPHDSQNNZBX-UHFFFAOYSA-N 0.000 description 2
- SSIGRKITSMOIDW-UHFFFAOYSA-N 4,5-dichloro-n,n-di(propan-2-yl)-1h-imidazole-2-carboxamide Chemical compound CC(C)N(C(C)C)C(=O)C1=NC(Cl)=C(Cl)N1 SSIGRKITSMOIDW-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241000234282 Allium Species 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 2
- 241001666377 Apera Species 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000005340 Asparagus officinalis Nutrition 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 241000132570 Centaurea Species 0.000 description 2
- 241000219312 Chenopodium Species 0.000 description 2
- 244000281762 Chenopodium ambrosioides Species 0.000 description 2
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
- 244000272323 Cirsium lanceolatum Species 0.000 description 2
- 235000010856 Cirsium lanceolatum Nutrition 0.000 description 2
- 241000208175 Daucus Species 0.000 description 2
- 244000294661 Emex spinosa Species 0.000 description 2
- 235000006369 Emex spinosa Nutrition 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241001290564 Fimbristylis Species 0.000 description 2
- 240000005702 Galium aparine Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- 241000520028 Lamium Species 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- 241001330453 Paspalum Species 0.000 description 2
- 241000219843 Pisum Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000209056 Secale Species 0.000 description 2
- 244000275012 Sesbania cannabina Species 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- 235000017967 Sphenoclea zeylanica Nutrition 0.000 description 2
- 244000273618 Sphenoclea zeylanica Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 241000219422 Urtica Species 0.000 description 2
- 240000005592 Veronica officinalis Species 0.000 description 2
- 241001506766 Xanthium Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 2
- WMJKNBGRUCPGLN-UHFFFAOYSA-N butan-2-yl 4,5-dichloro-1h-imidazole-2-carboxylate Chemical compound CCC(C)OC(=O)C1=NC(Cl)=C(Cl)N1 WMJKNBGRUCPGLN-UHFFFAOYSA-N 0.000 description 2
- 125000006226 butoxyethyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 241001233957 eudicotyledons Species 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- OAQLCSHKZXOBLW-UHFFFAOYSA-N propan-2-yl 4,5-dichloro-1h-imidazole-2-carboxylate Chemical compound CC(C)OC(=O)C1=NC(Cl)=C(Cl)N1 OAQLCSHKZXOBLW-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JZKRKFJKCWQXGD-UHFFFAOYSA-N (4,5-dichloro-1h-imidazol-2-yl)-morpholin-4-ylmethanone Chemical compound N1C(Cl)=C(Cl)N=C1C(=O)N1CCOCC1 JZKRKFJKCWQXGD-UHFFFAOYSA-N 0.000 description 1
- GXHPCVJGAHVTGO-UHFFFAOYSA-N 1,1,1-trichloro-2-(chloromethoxy)ethane Chemical compound ClCOCC(Cl)(Cl)Cl GXHPCVJGAHVTGO-UHFFFAOYSA-N 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- DXVFNVVZTIAYDC-UHFFFAOYSA-N 1,3,5-trichloro-2-(chloromethoxy)benzene Chemical compound ClCOC1=C(Cl)C=C(Cl)C=C1Cl DXVFNVVZTIAYDC-UHFFFAOYSA-N 0.000 description 1
- UYQMOVZSNGYALK-UHFFFAOYSA-N 1-(chloromethoxy)-2-ethylsulfanylethane Chemical compound CCSCCOCCl UYQMOVZSNGYALK-UHFFFAOYSA-N 0.000 description 1
- RRRBNCDKPVHUNU-UHFFFAOYSA-N 1-(chloromethoxy)-2-methylpropane Chemical compound CC(C)COCCl RRRBNCDKPVHUNU-UHFFFAOYSA-N 0.000 description 1
- AGDIDCDJVCRQCJ-UHFFFAOYSA-N 1-(chloromethoxy)hexane Chemical compound CCCCCCOCCl AGDIDCDJVCRQCJ-UHFFFAOYSA-N 0.000 description 1
- DWEGZHKHRPLUST-UHFFFAOYSA-N 1-(chloromethoxymethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(COCCl)=C1 DWEGZHKHRPLUST-UHFFFAOYSA-N 0.000 description 1
- DNZXMWKFPMIKRG-UHFFFAOYSA-N 1-(chloromethoxymethyl)-4-methoxybenzene Chemical compound COC1=CC=C(COCCl)C=C1 DNZXMWKFPMIKRG-UHFFFAOYSA-N 0.000 description 1
- IFMYFXJJIIGOIS-UHFFFAOYSA-N 1-(pyridin-3-ylmethyl)piperidin-4-amine;trihydrochloride Chemical compound Cl.Cl.Cl.C1CC(N)CCN1CC1=CC=CN=C1 IFMYFXJJIIGOIS-UHFFFAOYSA-N 0.000 description 1
- LUTWEKBTDWRTSE-UHFFFAOYSA-N 1-chloro-2-(chloromethoxy)ethane Chemical compound ClCCOCCl LUTWEKBTDWRTSE-UHFFFAOYSA-N 0.000 description 1
- MGJBSBASPDTFCV-UHFFFAOYSA-N 2,2-dimethylpropyl 4,5-dichloro-1h-imidazole-2-carboxylate Chemical compound CC(C)(C)COC(=O)C1=NC(Cl)=C(Cl)N1 MGJBSBASPDTFCV-UHFFFAOYSA-N 0.000 description 1
- FCFQBSFFWBHUQI-UHFFFAOYSA-N 2,4,5-trichloro-1-(ethoxymethyl)imidazole Chemical compound CCOCN1C(Cl)=NC(Cl)=C1Cl FCFQBSFFWBHUQI-UHFFFAOYSA-N 0.000 description 1
- KPUQILRBGVUAFH-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethoxy)benzene Chemical compound ClCOC1=CC=C(Cl)C=C1Cl KPUQILRBGVUAFH-UHFFFAOYSA-N 0.000 description 1
- GSGPUGZLDGHFDO-UHFFFAOYSA-N 2-(chloromethoxy)propane Chemical compound CC(C)OCCl GSGPUGZLDGHFDO-UHFFFAOYSA-N 0.000 description 1
- KJMXVHBTWJSSBL-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-imidazole Chemical compound FC(F)(F)C1=NC=CN1 KJMXVHBTWJSSBL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OENYNJCXBYNSLP-UHFFFAOYSA-N 2-methoxyethyl 4,5-dichloro-1h-imidazole-2-carboxylate Chemical compound COCCOC(=O)C1=NC(Cl)=C(Cl)N1 OENYNJCXBYNSLP-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- SWEUGVWEJFPDTD-UHFFFAOYSA-N 4,5-dichloro-1-(chloromethyl)-2-(trifluoromethyl)imidazole Chemical compound FC(F)(F)C1=NC(Cl)=C(Cl)N1CCl SWEUGVWEJFPDTD-UHFFFAOYSA-N 0.000 description 1
- LIXFBBSTBMFPPQ-UHFFFAOYSA-N 4,5-dichloro-1-(cyclohexyloxymethyl)imidazole-2-carbonitrile Chemical compound ClC1=C(Cl)N=C(C#N)N1COC1CCCCC1 LIXFBBSTBMFPPQ-UHFFFAOYSA-N 0.000 description 1
- MSGMEYRYLDDYOD-UHFFFAOYSA-N 4,5-dichloro-1-(cyclopentyloxymethyl)imidazole-2-carbonitrile Chemical compound ClC1=C(Cl)N=C(C#N)N1COC1CCCC1 MSGMEYRYLDDYOD-UHFFFAOYSA-N 0.000 description 1
- YTFKLHAAKIOBAB-UHFFFAOYSA-N 4,5-dichloro-1-(ethoxymethyl)-n,n-diethylimidazole-2-carboxamide Chemical compound CCOCN1C(Cl)=C(Cl)N=C1C(=O)N(CC)CC YTFKLHAAKIOBAB-UHFFFAOYSA-N 0.000 description 1
- IBCSGMVTUAFCSI-UHFFFAOYSA-N 4,5-dichloro-1-(ethoxymethyl)-n,n-dimethylimidazole-2-carboxamide Chemical compound CCOCN1C(Cl)=C(Cl)N=C1C(=O)N(C)C IBCSGMVTUAFCSI-UHFFFAOYSA-N 0.000 description 1
- SNWPTLYYNGTBSO-UHFFFAOYSA-N 4,5-dichloro-1-(ethoxymethyl)-n-(3-methoxypropyl)imidazole-2-carboxamide Chemical compound CCOCN1C(Cl)=C(Cl)N=C1C(=O)NCCCOC SNWPTLYYNGTBSO-UHFFFAOYSA-N 0.000 description 1
- XTJNMQOWWBURFW-UHFFFAOYSA-N 4,5-dichloro-1-(ethoxymethyl)-n-[[4-(trifluoromethyl)phenyl]methyl]imidazole-2-carboxamide Chemical compound CCOCN1C(Cl)=C(Cl)N=C1C(=O)NCC1=CC=C(C(F)(F)F)C=C1 XTJNMQOWWBURFW-UHFFFAOYSA-N 0.000 description 1
- ZTRRQOHYXMHFEE-UHFFFAOYSA-N 4,5-dichloro-1-(ethoxymethyl)-n-ethylimidazole-2-carboxamide Chemical compound CCNC(=O)C1=NC(Cl)=C(Cl)N1COCC ZTRRQOHYXMHFEE-UHFFFAOYSA-N 0.000 description 1
- LBJUQPRDPLOQBH-UHFFFAOYSA-N 4,5-dichloro-1-(ethoxymethyl)-n-methylimidazole-2-carboxamide Chemical compound CCOCN1C(Cl)=C(Cl)N=C1C(=O)NC LBJUQPRDPLOQBH-UHFFFAOYSA-N 0.000 description 1
- RTZTUZCVTZCYIF-UHFFFAOYSA-N 4,5-dichloro-1-(methoxymethyl)-2-(trifluoromethyl)imidazole Chemical compound COCN1C(Cl)=C(Cl)N=C1C(F)(F)F RTZTUZCVTZCYIF-UHFFFAOYSA-N 0.000 description 1
- VFYYNGBISWBXDS-UHFFFAOYSA-N 4,5-dichloro-1-(phenylmethoxymethyl)imidazole-2-carbonitrile Chemical compound ClC1=C(Cl)N=C(C#N)N1COCC1=CC=CC=C1 VFYYNGBISWBXDS-UHFFFAOYSA-N 0.000 description 1
- SVZKYUGFOIOVFE-UHFFFAOYSA-N 4,5-dichloro-1-(propan-2-yloxymethyl)imidazole-2-carbonitrile Chemical compound CC(C)OCN1C(Cl)=C(Cl)N=C1C#N SVZKYUGFOIOVFE-UHFFFAOYSA-N 0.000 description 1
- PHGLSKNLULFMSY-UHFFFAOYSA-N 4,5-dichloro-1-(propoxymethyl)imidazole-2-carbonitrile Chemical compound CCCOCN1C(Cl)=C(Cl)N=C1C#N PHGLSKNLULFMSY-UHFFFAOYSA-N 0.000 description 1
- BRRRXHKIEVPGBP-UHFFFAOYSA-N 4,5-dichloro-N-(4-methoxyphenyl)-1H-imidazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=NC(Cl)=C(Cl)N1 BRRRXHKIEVPGBP-UHFFFAOYSA-N 0.000 description 1
- SUVMCTQZWMYEAI-UHFFFAOYSA-N 4,5-dichloro-n,n-diethyl-1h-imidazole-2-carboxamide Chemical compound CCN(CC)C(=O)C1=NC(Cl)=C(Cl)N1 SUVMCTQZWMYEAI-UHFFFAOYSA-N 0.000 description 1
- LSFNFJXMJIBOAH-UHFFFAOYSA-N 4,5-dichloro-n,n-dimethyl-1h-imidazole-2-carboxamide Chemical compound CN(C)C(=O)C1=NC(Cl)=C(Cl)N1 LSFNFJXMJIBOAH-UHFFFAOYSA-N 0.000 description 1
- XUOAGBQIDQVKEX-UHFFFAOYSA-N 4,5-dichloro-n-(2-chlorophenyl)-1h-imidazole-2-carboxamide Chemical compound N1C(Cl)=C(Cl)N=C1C(=O)NC1=CC=CC=C1Cl XUOAGBQIDQVKEX-UHFFFAOYSA-N 0.000 description 1
- MQAKFUPSOLJMCH-UHFFFAOYSA-N 4,5-dichloro-n-[(4-chlorophenyl)methyl]-1-(ethoxymethyl)imidazole-2-carboxamide Chemical compound CCOCN1C(Cl)=C(Cl)N=C1C(=O)NCC1=CC=C(Cl)C=C1 MQAKFUPSOLJMCH-UHFFFAOYSA-N 0.000 description 1
- KGBYGVGVDLHOSP-UHFFFAOYSA-N 4,5-dichloro-n-[(4-methoxyphenyl)methyl]-1h-imidazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=NC(Cl)=C(Cl)N1 KGBYGVGVDLHOSP-UHFFFAOYSA-N 0.000 description 1
- GCLSLQIIZKHMRI-UHFFFAOYSA-N 4,5-dichloro-n-cyclohexyl-1h-imidazole-2-carboxamide Chemical compound N1C(Cl)=C(Cl)N=C1C(=O)NC1CCCCC1 GCLSLQIIZKHMRI-UHFFFAOYSA-N 0.000 description 1
- BNNUWAAJAJMGMQ-UHFFFAOYSA-N 4,5-dichloro-n-cyclopentyl-1-(ethoxymethyl)imidazole-2-carboxamide Chemical compound CCOCN1C(Cl)=C(Cl)N=C1C(=O)NC1CCCC1 BNNUWAAJAJMGMQ-UHFFFAOYSA-N 0.000 description 1
- HJVOPEVYKDFNEY-UHFFFAOYSA-N 4,5-dichloro-n-cyclopentyl-1h-imidazole-2-carboxamide Chemical compound N1C(Cl)=C(Cl)N=C1C(=O)NC1CCCC1 HJVOPEVYKDFNEY-UHFFFAOYSA-N 0.000 description 1
- YKKDKYKWZFYLIM-UHFFFAOYSA-N 4,5-dichloro-n-ethyl-1h-imidazole-2-carboxamide Chemical compound CCNC(=O)C1=NC(Cl)=C(Cl)N1 YKKDKYKWZFYLIM-UHFFFAOYSA-N 0.000 description 1
- WIHWJFQDBNHAOY-UHFFFAOYSA-N 4,5-dichloro-n-methyl-1h-imidazole-2-carboxamide Chemical compound CNC(=O)C1=NC(Cl)=C(Cl)N1 WIHWJFQDBNHAOY-UHFFFAOYSA-N 0.000 description 1
- PWLSRLAPJWZJHA-UHFFFAOYSA-N 4-chloro-1-(chloromethoxy)-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1OCCl PWLSRLAPJWZJHA-UHFFFAOYSA-N 0.000 description 1
- BQRBAXFOPZRMCU-UHFFFAOYSA-N 5-chloro-1h-imidazole Chemical compound ClC1=CN=CN1 BQRBAXFOPZRMCU-UHFFFAOYSA-N 0.000 description 1
- XHZHVQQDASRBHW-UHFFFAOYSA-N 5-chloro-1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC(Cl)=CN1 XHZHVQQDASRBHW-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 241000209136 Agropyron Species 0.000 description 1
- 241000743339 Agrostis Species 0.000 description 1
- 240000007241 Agrostis stolonifera Species 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 241000743987 Alopecurus pratensis Species 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
- 240000008575 Ammannia baccifera Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 241000404028 Anthemis Species 0.000 description 1
- 235000007639 Anthemis cotula Nutrition 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
- 244000003416 Asparagus officinalis Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000611157 Brachiaria Species 0.000 description 1
- 241000339490 Brachyachne Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- RCUIOTMPQCRWHE-UHFFFAOYSA-N CC1=CC=C(NC(=O)C=2NC(=C(N=2)Cl)Cl)C=C1 Chemical compound CC1=CC=C(NC(=O)C=2NC(=C(N=2)Cl)Cl)C=C1 RCUIOTMPQCRWHE-UHFFFAOYSA-N 0.000 description 1
- ZEMGEMNRZLQAOH-UHFFFAOYSA-N CSCCN.OC(C(N1)=NC(Cl)=C1Cl)=O Chemical compound CSCCN.OC(C(N1)=NC(Cl)=C1Cl)=O ZEMGEMNRZLQAOH-UHFFFAOYSA-N 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000320316 Carduus Species 0.000 description 1
- 241001049165 Caria Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 240000000005 Chenopodium berlandieri Species 0.000 description 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- PKKOQYHJAZRPKV-UHFFFAOYSA-N ClC1=CC=C(NC(=O)C=2N(C(=C(N=2)Cl)Cl)COCC)C=C1 Chemical compound ClC1=CC=C(NC(=O)C=2N(C(=C(N=2)Cl)Cl)COCC)C=C1 PKKOQYHJAZRPKV-UHFFFAOYSA-N 0.000 description 1
- PBRDNTWCHQSGQX-UHFFFAOYSA-N ClC=1C=C(NC(=O)C=2N(C(=C(N=2)Cl)Cl)COCC)C=CC=1Cl Chemical compound ClC=1C=C(NC(=O)C=2N(C(=C(N=2)Cl)Cl)COCC)C=CC=1Cl PBRDNTWCHQSGQX-UHFFFAOYSA-N 0.000 description 1
- 235000010071 Cucumis prophetarum Nutrition 0.000 description 1
- 244000024469 Cucumis prophetarum Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 244000052363 Cynodon dactylon Species 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 235000002848 Cyperus flabelliformis Nutrition 0.000 description 1
- 240000001505 Cyperus odoratus Species 0.000 description 1
- 241000320605 Dactyloctenium Species 0.000 description 1
- 240000006541 Dactyloctenium aegyptium Species 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 235000001248 Dentaria laciniata Nutrition 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 244000127993 Elaeis melanococca Species 0.000 description 1
- 241000202829 Eleocharis Species 0.000 description 1
- 244000139825 Eleocharis ochrostachys Species 0.000 description 1
- 235000007351 Eleusine Nutrition 0.000 description 1
- 241000209215 Eleusine Species 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 241000816457 Galeopsis Species 0.000 description 1
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 1
- 244000214240 Galinsoga parviflora Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 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 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- 241001327265 Ischaemum Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000208822 Lactuca Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000017074 Lepidium campestre Nutrition 0.000 description 1
- 244000136541 Lepidium campestre Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 240000007038 Lindernia dubia Species 0.000 description 1
- 241000208204 Linum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 235000002262 Lycopersicon Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 240000000982 Malva neglecta Species 0.000 description 1
- 235000000060 Malva neglecta Nutrition 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 244000070788 Milium effusum Species 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- JWOUVXSDAIIATJ-UHFFFAOYSA-N NCC1=CC=C(C(F)(F)F)C=C1.OC(C(N1)=NC(Cl)=C1Cl)=O Chemical compound NCC1=CC=C(C(F)(F)F)C=C1.OC(C(N1)=NC(Cl)=C1Cl)=O JWOUVXSDAIIATJ-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WBIXHWOSMPOVGX-UHFFFAOYSA-N OC(=O)C1=NC(Cl)=C(Cl)N1.NC1=CC=C(Cl)C(C(F)(F)F)=C1 Chemical compound OC(=O)C1=NC(Cl)=C(Cl)N1.NC1=CC=C(Cl)C(C(F)(F)F)=C1 WBIXHWOSMPOVGX-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000007199 Panicum miliaceum Nutrition 0.000 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 241000209048 Poa Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 241001310793 Podium Species 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 241000490453 Rorippa Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000341978 Rotala Species 0.000 description 1
- 241000209051 Saccharum Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000009132 Sagittaria sagittifolia Species 0.000 description 1
- 241000202758 Scirpus Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 241000488874 Sonchus Species 0.000 description 1
- 244000111146 Sonchus arvensis Species 0.000 description 1
- 235000008132 Sonchus arvensis ssp. uliginosus Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- 241001521331 Urochloa Species 0.000 description 1
- 241000159750 Urtica cannabina Species 0.000 description 1
- 240000001261 Urtica urens Species 0.000 description 1
- 235000005545 Veronica americana Nutrition 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 244000193174 agave Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 235000006263 bur ragweed Nutrition 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- GYCLGFVWNVHUPA-UHFFFAOYSA-N chloromethoxycyclohexane Chemical compound ClCOC1CCCCC1 GYCLGFVWNVHUPA-UHFFFAOYSA-N 0.000 description 1
- ZQZBBQNLHWBXPW-UHFFFAOYSA-N chloromethoxycyclopentane Chemical compound ClCOC1CCCC1 ZQZBBQNLHWBXPW-UHFFFAOYSA-N 0.000 description 1
- LADPCMZCENPFGV-UHFFFAOYSA-N chloromethoxymethylbenzene Chemical compound ClCOCC1=CC=CC=C1 LADPCMZCENPFGV-UHFFFAOYSA-N 0.000 description 1
- QZZVDGKPSLFMGA-UHFFFAOYSA-N chloromethoxymethylcyclohexane Chemical compound ClCOCC1CCCCC1 QZZVDGKPSLFMGA-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 235000003488 common ragweed Nutrition 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- VJPHAMJNGICSLT-UHFFFAOYSA-N cyclohexanecarboxylic acid N-methylamide Natural products CNC(=O)C1CCCCC1 VJPHAMJNGICSLT-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- VLUBCRVJZVBQGI-UHFFFAOYSA-N ethyl 4,5-dichloro-1h-imidazole-2-carboxylate Chemical compound CCOC(=O)C1=NC(Cl)=C(Cl)N1 VLUBCRVJZVBQGI-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- GLHMGLRXTSXOAB-UHFFFAOYSA-N hexyl 4,5-dichloro-1h-imidazole-2-carboxylate Chemical compound CCCCCCOC(=O)C1=NC(Cl)=C(Cl)N1 GLHMGLRXTSXOAB-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- PFDAEWQJCFLSGX-UHFFFAOYSA-N methyl 4,5-dichloro-1h-imidazole-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(Cl)N1 PFDAEWQJCFLSGX-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- ALJAACCRTQOYEJ-UHFFFAOYSA-N n-(4-chlorophenyl)-1h-imidazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=NC=CN1 ALJAACCRTQOYEJ-UHFFFAOYSA-N 0.000 description 1
- WZIXEPQIRVLZID-UHFFFAOYSA-N n-benzyl-4,5-dichloro-1-(ethoxymethyl)imidazole-2-carboxamide Chemical compound CCOCN1C(Cl)=C(Cl)N=C1C(=O)NCC1=CC=CC=C1 WZIXEPQIRVLZID-UHFFFAOYSA-N 0.000 description 1
- QRYOOMKQVAYBHS-UHFFFAOYSA-N n-benzyl-4,5-dichloro-1h-imidazole-2-carboxamide Chemical compound N1C(Cl)=C(Cl)N=C1C(=O)NCC1=CC=CC=C1 QRYOOMKQVAYBHS-UHFFFAOYSA-N 0.000 description 1
- ANORDWOIBSUYBN-UHFFFAOYSA-N n-chloro-1-phenylmethanamine Chemical compound ClNCC1=CC=CC=C1 ANORDWOIBSUYBN-UHFFFAOYSA-N 0.000 description 1
- DYUSVPKMWAMYDH-UHFFFAOYSA-N n-ethoxyethanamine Chemical compound CCNOCC DYUSVPKMWAMYDH-UHFFFAOYSA-N 0.000 description 1
- MZPAQCAPWLAKSD-UHFFFAOYSA-N n-phenyl-1h-pyrrole-2-carboxamide Chemical compound C=1C=CNC=1C(=O)NC1=CC=CC=C1 MZPAQCAPWLAKSD-UHFFFAOYSA-N 0.000 description 1
- RKBZTAFUUBPJOI-UHFFFAOYSA-N n-tert-butyl-1h-imidazole-2-carboxamide Chemical compound CC(C)(C)NC(=O)C1=NC=CN1 RKBZTAFUUBPJOI-UHFFFAOYSA-N 0.000 description 1
- RCUVNLUSDCTIFE-UHFFFAOYSA-N n-tert-butyl-4,5-dichloro-1h-imidazole-2-carboxamide Chemical compound CC(C)(C)NC(=O)C1=NC(Cl)=C(Cl)N1 RCUVNLUSDCTIFE-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- AZYLLVUWUFRQQB-UHFFFAOYSA-N prop-2-ynyl 4,5-dichloro-1h-imidazole-2-carboxylate Chemical compound ClC=1N=C(C(=O)OCC#C)NC=1Cl AZYLLVUWUFRQQB-UHFFFAOYSA-N 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KAVLDJDIIUFSCM-UHFFFAOYSA-N tert-butyl 4,5-dichloro-1h-imidazole-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=NC(Cl)=C(Cl)N1 KAVLDJDIIUFSCM-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- C07D233/66—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 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
- C07D233/68—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—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 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762646144 DE2646144A1 (de) | 1976-10-13 | 1976-10-13 | 4,5-dichlor-imidazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1576508A true GB1576508A (en) | 1980-10-08 |
Family
ID=5990351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42078/77A Expired GB1576508A (en) | 1976-10-13 | 1977-10-10 | 4,5 - dichloroimidazole derivatives and their use as plant protection agents |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4178166A (enExample) |
| JP (1) | JPS5350164A (enExample) |
| AU (1) | AU2966277A (enExample) |
| BE (1) | BE859629A (enExample) |
| BR (1) | BR7706803A (enExample) |
| CA (1) | CA1100977A (enExample) |
| DD (1) | DD133036A5 (enExample) |
| DE (1) | DE2646144A1 (enExample) |
| DK (1) | DK452577A (enExample) |
| ES (1) | ES463162A1 (enExample) |
| FR (1) | FR2367752A1 (enExample) |
| GB (1) | GB1576508A (enExample) |
| IL (1) | IL53089A0 (enExample) |
| NL (1) | NL7711209A (enExample) |
| PL (1) | PL103698B1 (enExample) |
| PT (1) | PT67151B (enExample) |
| SE (1) | SE7711482L (enExample) |
| SU (1) | SU665777A3 (enExample) |
| TR (1) | TR19489A (enExample) |
| ZA (1) | ZA776076B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2646144A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 4,5-dichlor-imidazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| US4571257A (en) * | 1985-05-06 | 1986-02-18 | Stauffer Chemical Company | Herbicidal esters of N-substituted 2-bromo-4-methylimidazole-5-carboxylic acid |
| JP4770821B2 (ja) | 2007-11-16 | 2011-09-14 | パナソニック株式会社 | 電気掃除機 |
| JP5454458B2 (ja) * | 2010-11-25 | 2014-03-26 | 信越化学工業株式会社 | ポジ型レジスト材料及びパターン形成方法 |
| ES2649937T3 (es) | 2010-12-21 | 2018-01-16 | Bayer Cropscience Lp | Mutantes tipo papel de lija de Bacillus y procedimientos de uso de los mismos para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas |
| MX2014002890A (es) | 2011-09-12 | 2015-01-19 | Bayer Cropscience Lp | Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos. |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1404757A (fr) * | 1963-07-01 | 1965-07-02 | Shell Int Research | Compositions empêchant la croissance des plantes nuisibles |
| GB1154722A (en) * | 1965-07-08 | 1969-06-11 | Boots Pure Drug Co Ltd | 2,4,5-Tribromoimidazole Derivatives and Compositions thereof |
| US3435050A (en) * | 1966-04-08 | 1969-03-25 | Dow Chemical Co | 2,4,5-trichloroimidazole and method of preparation |
| CH485733A (de) * | 1967-04-26 | 1970-02-15 | Agripat Sa | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
| CH528514A (de) * | 1969-05-22 | 1972-09-30 | Bayer Ag | Verfahren zur Herstellung von Acylimidazolen |
| US3759948A (en) * | 1969-06-25 | 1973-09-18 | Merck & Co Inc | Non-steroid anti-inflammatory compounds |
| US3996366A (en) * | 1973-11-19 | 1976-12-07 | The Boots Company Limited | Thio derivatives of imidazol-1-yl carboxamides |
| US4134983A (en) * | 1975-03-03 | 1979-01-16 | Merck & Co., Inc. | 3-amino-2-or-propoxyaryl substituted imidazoles |
| DE2646144A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 4,5-dichlor-imidazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| US4185991A (en) * | 1976-10-13 | 1980-01-29 | Bayer Aktiengesellschaft | 4,5-Dichloro-imidazole derivatives and their use as herbicides |
-
1976
- 1976-10-13 DE DE19762646144 patent/DE2646144A1/de not_active Withdrawn
-
1977
- 1977-09-21 US US05/835,095 patent/US4178166A/en not_active Expired - Lifetime
- 1977-10-05 SU SU772528102A patent/SU665777A3/ru active
- 1977-10-10 IL IL53089A patent/IL53089A0/xx unknown
- 1977-10-10 DD DD7700201434A patent/DD133036A5/xx unknown
- 1977-10-10 GB GB42078/77A patent/GB1576508A/en not_active Expired
- 1977-10-12 BR BR7706803A patent/BR7706803A/pt unknown
- 1977-10-12 NL NL7711209A patent/NL7711209A/xx not_active Application Discontinuation
- 1977-10-12 ZA ZA00776076A patent/ZA776076B/xx unknown
- 1977-10-12 PL PL1977201462A patent/PL103698B1/pl unknown
- 1977-10-12 TR TR19489A patent/TR19489A/xx unknown
- 1977-10-12 BE BE181659A patent/BE859629A/xx unknown
- 1977-10-12 CA CA288,546A patent/CA1100977A/en not_active Expired
- 1977-10-12 FR FR7730723A patent/FR2367752A1/fr active Granted
- 1977-10-12 DK DK452577A patent/DK452577A/da unknown
- 1977-10-12 SE SE7711482A patent/SE7711482L/xx unknown
- 1977-10-12 PT PT67151A patent/PT67151B/pt unknown
- 1977-10-13 JP JP12193977A patent/JPS5350164A/ja active Pending
- 1977-10-13 AU AU29662/77A patent/AU2966277A/en active Pending
- 1977-10-13 ES ES463162A patent/ES463162A1/es not_active Expired
-
1979
- 1979-04-30 US US06/034,712 patent/US4268681A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5350164A (en) | 1978-05-08 |
| BE859629A (fr) | 1978-04-12 |
| PL103698B1 (pl) | 1979-07-31 |
| ZA776076B (en) | 1978-09-27 |
| AU2966277A (en) | 1979-04-26 |
| DD133036A5 (de) | 1978-11-29 |
| SE7711482L (sv) | 1978-04-14 |
| BR7706803A (pt) | 1978-07-04 |
| DK452577A (da) | 1978-04-14 |
| CA1100977A (en) | 1981-05-12 |
| IL53089A0 (en) | 1977-12-30 |
| DE2646144A1 (de) | 1978-04-20 |
| US4178166A (en) | 1979-12-11 |
| PL201462A1 (pl) | 1978-06-19 |
| TR19489A (tr) | 1979-04-17 |
| NL7711209A (nl) | 1978-04-17 |
| PT67151B (de) | 1979-03-19 |
| ES463162A1 (es) | 1978-07-16 |
| US4268681A (en) | 1981-05-19 |
| SU665777A3 (ru) | 1979-05-30 |
| PT67151A (de) | 1977-11-01 |
| FR2367752B1 (enExample) | 1981-07-24 |
| FR2367752A1 (fr) | 1978-05-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1576510A (en) | 4,5 - dichloroimidazole - 1 - carboxylic acid aryl esters and their use a splant protection agents | |
| JPH0377873A (ja) | ３‐アミノ‐５‐アミノカルボニル‐１，２，４‐トリアゾール誘導体 | |
| KR920005414B1 (ko) | 5-할로게노알킬-1, 3, 4-티아디아졸-2-일옥시아세트 아미드의 제조방법 | |
| US4517011A (en) | N-substituted halogenoacetanilides and their use as herbicides | |
| EP0572855A1 (en) | 1-(3-Halo-4-substituted phenyl)tetrazolinone derivatives, their preparation and their use as herbicides | |
| EP0571855A1 (en) | 1-(3-Halo-4-trifluoromethyl-phenyl)tetrazolinone derivatives, their preparation and their use as herbicides | |
| GB1576508A (en) | 4,5 - dichloroimidazole derivatives and their use as plant protection agents | |
| US4623377A (en) | 1,2,3,4-tetrahydroquinolin-1-ylcarbonylimidazoles and herbicidal use thereof | |
| US4185991A (en) | 4,5-Dichloro-imidazole derivatives and their use as herbicides | |
| JPH0651688B2 (ja) | ４．５―ジ置換１．３―チアゾル―２―イル―オキシアセタミド類 | |
| US4067724A (en) | N-(1,2,4-Triazin-5-on-4-yl)-glycines and herbicidal compositions | |
| US4505739A (en) | Herbicidal 5-t-butyl-3-(N-alkanoylamino)pyrazoles | |
| US4470842A (en) | Herbicidally active novel 3-alken(in)yl-mercapto(amino)-4-amino-6-tert-butyl-1,2,4-triazin-5-ones | |
| US4058525A (en) | 4-Amino-5-thione-1,2,4-triazines | |
| US4565566A (en) | Imidazo-pyrrolo-pyridine derivatives useful as herbicidal agents | |
| GB1566842A (en) | Chloromethane-sulphonic acid anilides and their use as herbicides | |
| US4386953A (en) | Herbicidally active substituted 6-halogeno-tert.-butyl-1,2,4-triazin-5-ones | |
| EP0477677B1 (en) | Herbicidally active benzoxazines | |
| US4233058A (en) | 4,5-Dichloro-imidazole-1-carboxylic acid aryl esters and their use as plant protection agents | |
| US4127404A (en) | 4-Amino-1,2,4-triazin-5-one compounds and herbicidal compositions | |
| US4187101A (en) | 1-Acyloxymethyl-4,5-dichloro-imidazole derivatives and their use as herbicides | |
| US4177055A (en) | 1-Acyloxymethyl-4,5-dichloro-imidazole-2-carboxylic acid derivatives and their use as plant protection agents | |
| US4402732A (en) | Herbicidally active dihalogenated imidazolecarboxylic acid amides, compositions and use | |
| US4726834A (en) | Herbicidal benzodisultam derivatives, composition, and method of use therefor | |
| US5158600A (en) | Herbicidal 3-hydroxy-2-cyclohexen-1-ones |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |