CA1221379A - Herbicidal 2-haloacetanilides - Google Patents
Herbicidal 2-haloacetanilidesInfo
- Publication number
- CA1221379A CA1221379A CA000373323A CA373323A CA1221379A CA 1221379 A CA1221379 A CA 1221379A CA 000373323 A CA000373323 A CA 000373323A CA 373323 A CA373323 A CA 373323A CA 1221379 A CA1221379 A CA 1221379A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- compound
- ethyl
- chloroacetanilide
- methoxy
- 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
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 318
- 241000196324 Embryophyta Species 0.000 claims abstract description 95
- 244000068988 Glycine max Species 0.000 claims abstract description 49
- 235000010469 Glycine max Nutrition 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 40
- 235000005853 Cyperus esculentus Nutrition 0.000 claims abstract description 31
- 241000508725 Elymus repens Species 0.000 claims abstract description 30
- 229920000742 Cotton Polymers 0.000 claims abstract description 27
- 240000001505 Cyperus odoratus Species 0.000 claims abstract description 27
- 240000006394 Sorghum bicolor Species 0.000 claims abstract description 17
- 244000105624 Arachis hypogaea Species 0.000 claims abstract description 13
- 235000020232 peanut Nutrition 0.000 claims abstract description 13
- 241000533293 Sesbania emerus Species 0.000 claims abstract description 12
- 235000006923 Sorghum x drummondii Nutrition 0.000 claims abstract description 10
- 241001300479 Macroptilium Species 0.000 claims abstract description 6
- 240000006410 Sida spinosa Species 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 235000010823 Digitaria sanguinalis Nutrition 0.000 claims description 16
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- 240000006122 Chenopodium album Species 0.000 claims description 14
- 235000009344 Chenopodium album Nutrition 0.000 claims description 14
- 235000001602 Digitaria X umfolozi Nutrition 0.000 claims description 14
- 235000017898 Digitaria ciliaris Nutrition 0.000 claims description 14
- 235000005476 Digitaria cruciata Nutrition 0.000 claims description 14
- 235000006830 Digitaria didactyla Nutrition 0.000 claims description 14
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 claims description 14
- 235000014716 Eleusine indica Nutrition 0.000 claims description 14
- 240000007594 Oryza sativa Species 0.000 claims description 12
- 235000007164 Oryza sativa Nutrition 0.000 claims description 12
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 235000007189 Oryza longistaminata Nutrition 0.000 claims description 11
- 244000036975 Ambrosia artemisiifolia Species 0.000 claims description 10
- 241000209504 Poaceae Species 0.000 claims description 10
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 claims description 9
- 240000001451 Rottboellia cochinchinensis Species 0.000 claims description 9
- 235000003484 annual ragweed Nutrition 0.000 claims description 9
- 235000006263 bur ragweed Nutrition 0.000 claims description 9
- 235000003488 common ragweed Nutrition 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 235000009736 ragweed Nutrition 0.000 claims description 9
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 8
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 8
- 235000021536 Sugar beet Nutrition 0.000 claims description 8
- 235000021307 Triticum Nutrition 0.000 claims description 8
- 241000044594 Urochloa plantaginea Species 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- YGTYRMDZBFYUCE-UHFFFAOYSA-N 2-chloro-n-(2-methoxy-6-methylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound COC1=CC=CC(C)=C1N(COC(C)C)C(=O)CCl YGTYRMDZBFYUCE-UHFFFAOYSA-N 0.000 claims description 7
- 240000001592 Amaranthus caudatus Species 0.000 claims description 7
- 235000009328 Amaranthus caudatus Nutrition 0.000 claims description 7
- 240000008853 Datura stramonium Species 0.000 claims description 7
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 7
- 240000001549 Ipomoea eriocarpa Species 0.000 claims description 6
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 claims description 6
- 235000005489 dwarf bean Nutrition 0.000 claims description 6
- 244000013123 dwarf bean Species 0.000 claims description 6
- UAHGQVFLBQXPMP-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-(2-methyl-6-propan-2-yloxyphenyl)acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1OC(C)C UAHGQVFLBQXPMP-UHFFFAOYSA-N 0.000 claims description 5
- 240000000321 Abutilon grandifolium Species 0.000 claims description 5
- 240000005979 Hordeum vulgare Species 0.000 claims description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 5
- 235000003403 Limnocharis flava Nutrition 0.000 claims description 5
- 241000209117 Panicum Species 0.000 claims description 5
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 claims description 5
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 claims description 5
- JCBJJXRYZQVZLI-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-(2-methoxy-6-methylphenyl)acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1OC JCBJJXRYZQVZLI-UHFFFAOYSA-N 0.000 claims description 4
- AZQWARXJQFTYKL-UHFFFAOYSA-N N-(butan-2-yloxymethyl)-2-chloro-N-(2-ethoxy-6-methylphenyl)acetamide Chemical compound C(C)OC1=C(N(C(CCl)=O)COC(CC)C)C(=CC=C1)C AZQWARXJQFTYKL-UHFFFAOYSA-N 0.000 claims description 4
- NHZRBSHFSUTGIW-UHFFFAOYSA-N n-(butan-2-yloxymethyl)-2-chloro-n-(2-methoxy-6-methylphenyl)acetamide Chemical compound CCC(C)OCN(C(=O)CCl)C1=C(C)C=CC=C1OC NHZRBSHFSUTGIW-UHFFFAOYSA-N 0.000 claims description 4
- PCPOAVKGDVIQOO-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-(2-methyl-6-propoxyphenyl)acetamide Chemical compound CCCOC1=CC=CC(C)=C1N(COCC)C(=O)CCl PCPOAVKGDVIQOO-UHFFFAOYSA-N 0.000 claims description 3
- 241001290610 Abildgaardia Species 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- LVLRQPAKYWRZEB-UHFFFAOYSA-N 2-chloro-N-(2-ethoxy-6-methylphenyl)-N-(prop-2-ynoxymethyl)acetamide Chemical compound C(C)OC1=C(N(C(CCl)=O)COCC#C)C(=CC=C1)C LVLRQPAKYWRZEB-UHFFFAOYSA-N 0.000 claims 3
- XFRZNVSLFMONEF-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methoxyphenyl)-N-(propan-2-yloxymethyl)acetamide Chemical compound COC1=C(N(C(CCl)=O)COC(C)C)C(=CC=C1)CC XFRZNVSLFMONEF-UHFFFAOYSA-N 0.000 claims 3
- QAZIQQHUNGBDPB-UHFFFAOYSA-N 2-chloro-N-(2-methyl-6-propan-2-yloxyphenyl)-N-(propoxymethyl)acetamide Chemical compound C(C)(C)OC1=C(N(C(CCl)=O)COCCC)C(=CC=C1)C QAZIQQHUNGBDPB-UHFFFAOYSA-N 0.000 claims 2
- 244000299507 Gossypium hirsutum Species 0.000 claims 2
- 244000098338 Triticum aestivum Species 0.000 claims 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 claims 1
- 235000004135 Amaranthus viridis Nutrition 0.000 claims 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 claims 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 claims 1
- 240000003176 Digitaria ciliaris Species 0.000 claims 1
- 244000058871 Echinochloa crus-galli Species 0.000 claims 1
- 241000380130 Ehrharta erecta Species 0.000 claims 1
- 235000012629 Mentha aquatica Nutrition 0.000 claims 1
- 240000000275 Persicaria hydropiper Species 0.000 claims 1
- 235000017337 Persicaria hydropiper Nutrition 0.000 claims 1
- 235000004442 Polygonum persicaria Nutrition 0.000 claims 1
- 244000067505 Xanthium strumarium Species 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 244000038559 crop plants Species 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 76
- 241000219146 Gossypium Species 0.000 abstract description 25
- 239000004480 active ingredient Substances 0.000 abstract description 23
- 240000002439 Sorghum halepense Species 0.000 abstract description 9
- 238000012360 testing method Methods 0.000 description 90
- 239000002689 soil Substances 0.000 description 51
- 230000000694 effects Effects 0.000 description 43
- -1 alkoxymethyl radical Chemical class 0.000 description 21
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 244000152970 Digitaria sanguinalis Species 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000004927 clay Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 241000192043 Echinochloa Species 0.000 description 11
- 239000004606 Fillers/Extenders Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000005416 organic matter Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 241000282320 Panthera leo Species 0.000 description 8
- 231100000817 safety factor Toxicity 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- 244000075634 Cyperus rotundus Species 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 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 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 244000062793 Sorghum vulgare Species 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 241000482268 Zea mays subsp. mays Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000010348 incorporation Methods 0.000 description 7
- 235000019713 millet Nutrition 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 241000894007 species Species 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 241001584884 Urochloa texana Species 0.000 description 6
- HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical group [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 6
- 238000003973 irrigation Methods 0.000 description 6
- 239000003380 propellant Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241001506766 Xanthium Species 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 4
- 238000007126 N-alkylation reaction Methods 0.000 description 4
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000002262 irrigation Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920001732 Lignosulfonate Polymers 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
- 241001148659 Panicum dichotomiflorum Species 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 229960000892 attapulgite Drugs 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000001473 noxious effect Effects 0.000 description 3
- 229910052625 palygorskite Inorganic materials 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 2
- 235000009434 Actinidia chinensis Nutrition 0.000 description 2
- 244000298697 Actinidia deliciosa Species 0.000 description 2
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001137251 Corvidae Species 0.000 description 2
- 241000490229 Eucephalus Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000017016 Setaria faberi Nutrition 0.000 description 2
- 241000820191 Setaria magna Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 150000008061 acetanilides Chemical class 0.000 description 2
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 2
- 150000003931 anilides Chemical group 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- JAMFGQBENKSWOF-UHFFFAOYSA-N bromo(methoxy)methane Chemical compound COCBr JAMFGQBENKSWOF-UHFFFAOYSA-N 0.000 description 2
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 239000002361 compost Substances 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 239000003864 humus Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000010871 livestock manure Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000010076 replication Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 239000010455 vermiculite Substances 0.000 description 2
- 229910052902 vermiculite Inorganic materials 0.000 description 2
- 235000019354 vermiculite Nutrition 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
- UHYKZPWOHVTEQB-UHFFFAOYSA-N 2-chloro-3-methoxy-N-phenylpropanamide Chemical compound COCC(Cl)C(=O)NC1=CC=CC=C1 UHYKZPWOHVTEQB-UHFFFAOYSA-N 0.000 description 1
- UVCLAMFLZZCURV-UHFFFAOYSA-N 2-chloro-N-(2-methyl-6-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=C(NC(=O)CCl)C(C)=CC=C1 UVCLAMFLZZCURV-UHFFFAOYSA-N 0.000 description 1
- KYDCMPAYVZHPHQ-UHFFFAOYSA-N 2-chloro-N-phenyl-3-propan-2-yloxypropanamide Chemical compound CC(C)OCC(Cl)C(=O)NC1=CC=CC=C1 KYDCMPAYVZHPHQ-UHFFFAOYSA-N 0.000 description 1
- JJXXUVSBKXEQBX-UHFFFAOYSA-N 2-chloro-N-phenyl-3-propoxypropanamide Chemical compound C(CC)OCC(C(=O)NC1=CC=CC=C1)Cl JJXXUVSBKXEQBX-UHFFFAOYSA-N 0.000 description 1
- IYLMCARCSCXVNP-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound CC(C)OCN(C(=O)CCl)C1=C(C)C=CC=C1C IYLMCARCSCXVNP-UHFFFAOYSA-N 0.000 description 1
- OTBNGXQXOSRONR-UHFFFAOYSA-N 2-chloro-n-(2-ethoxyethyl)-n-(2-methoxy-6-methylphenyl)acetamide Chemical compound CCOCCN(C(=O)CCl)C1=C(C)C=CC=C1OC OTBNGXQXOSRONR-UHFFFAOYSA-N 0.000 description 1
- SWQNAOCHGBVVSE-UHFFFAOYSA-N 2-chloro-n-(2-methoxy-6-methylphenyl)-n-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C1=C(C)C=CC=C1OC SWQNAOCHGBVVSE-UHFFFAOYSA-N 0.000 description 1
- HHRZBYFCNZFYAB-UHFFFAOYSA-N 2-chloro-n-(2-methoxy-6-methylphenyl)acetamide Chemical compound COC1=CC=CC(C)=C1NC(=O)CCl HHRZBYFCNZFYAB-UHFFFAOYSA-N 0.000 description 1
- NNVRQGZJHLEKBG-UHFFFAOYSA-N 2-chloro-n-(2-methoxyethyl)-n-(2-methoxy-6-methylphenyl)acetamide Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1OC NNVRQGZJHLEKBG-UHFFFAOYSA-N 0.000 description 1
- HKOJYPPTIPJZAZ-UHFFFAOYSA-N 2-methoxy-6-methylaniline Chemical compound COC1=CC=CC(C)=C1N HKOJYPPTIPJZAZ-UHFFFAOYSA-N 0.000 description 1
- JDXQHFXXWWIZKT-UHFFFAOYSA-N 2-n,4-n-diethyl-1,3,5-triazine-2,4-diamine Chemical compound CCNC1=NC=NC(NCC)=N1 JDXQHFXXWWIZKT-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-M 2-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-M 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- 241000931526 Acer campestre Species 0.000 description 1
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000499945 Amaryllis Species 0.000 description 1
- 244000261411 Astragalus glycyphyllos Species 0.000 description 1
- 235000010110 Astragalus glycyphyllos Nutrition 0.000 description 1
- 101100004280 Caenorhabditis elegans best-2 gene Proteins 0.000 description 1
- 101100495256 Caenorhabditis elegans mat-3 gene Proteins 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
- 101100020630 Dietzia sp. (strain CQ4) lbtA gene Proteins 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 241000982822 Ficus obtusifolia Species 0.000 description 1
- 241001481828 Glyptocephalus cynoglossus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000976924 Inca Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241001233242 Lontra Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 244000007853 Sarothamnus scoparius Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- 241000244317 Tillandsia usneoides Species 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- IVUXTESCPZUGJC-UHFFFAOYSA-N chloroxuron Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1OC1=CC=C(Cl)C=C1 IVUXTESCPZUGJC-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000036576 dermal application Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 229940113724 end-itch Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- UUSXSNJAQDJKCG-UHFFFAOYSA-N iodo(methoxy)methane Chemical class COCI UUSXSNJAQDJKCG-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- 239000001115 mace Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- VULHYRAYXYTONQ-UHFFFAOYSA-N n-phenylmethanimine Chemical compound C=NC1=CC=CC=C1 VULHYRAYXYTONQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 235000015108 pies Nutrition 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- AUPJTDWZPFFCCP-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCN(C)CCS([O-])(=O)=O AUPJTDWZPFFCCP-GMFCBQQYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000005690 transetherification reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13369580A | 1980-03-25 | 1980-03-25 | |
| US133,695 | 1980-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1221379A true CA1221379A (en) | 1987-05-05 |
Family
ID=22459883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000373323A Expired CA1221379A (en) | 1980-03-25 | 1981-03-18 | Herbicidal 2-haloacetanilides |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS56145252A (cs) |
| AT (1) | AT374659B (cs) |
| AU (1) | AU536794B2 (cs) |
| BE (1) | BE887995A (cs) |
| BG (1) | BG35893A3 (cs) |
| BR (1) | BR8101604A (cs) |
| CA (1) | CA1221379A (cs) |
| CH (1) | CH645878A5 (cs) |
| CS (1) | CS226729B2 (cs) |
| DD (1) | DD157298A5 (cs) |
| DE (1) | DE3110525C2 (cs) |
| DK (1) | DK120581A (cs) |
| FI (1) | FI73971C (cs) |
| FR (1) | FR2479205A1 (cs) |
| GB (1) | GB2072175B (cs) |
| GR (1) | GR66542B (cs) |
| HU (1) | HU189495B (cs) |
| IE (1) | IE51103B1 (cs) |
| IL (1) | IL62409A (cs) |
| IT (1) | IT1144661B (cs) |
| LU (1) | LU83237A1 (cs) |
| MA (1) | MA19101A1 (cs) |
| NL (1) | NL8101327A (cs) |
| NO (1) | NO151586C (cs) |
| NZ (1) | NZ196540A (cs) |
| PL (1) | PL125377B1 (cs) |
| PT (1) | PT72678B (cs) |
| RO (3) | RO85530B (cs) |
| SE (1) | SE8101729L (cs) |
| TR (1) | TR20885A (cs) |
| ZA (1) | ZA811801B (cs) |
| ZW (1) | ZW5881A1 (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1144666B (it) * | 1980-03-25 | 1986-10-29 | Monsanto Co | Derivati di n-alcossimetil-2-aloacetanilidi erbicidi |
| FR2479201B1 (fr) * | 1980-03-25 | 1985-05-31 | Monsanto Co | Composes de n-hydrocarbyloxymethyl-2-haloacetanilides et compositions herbicides les renfermant |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547620A (en) * | 1969-01-23 | 1970-12-15 | Monsanto Co | N-(oxamethyl)alpha-halo-acetanilide herbicides |
| US4258196A (en) * | 1978-04-17 | 1981-03-24 | Monsanto Company | Process for the production of tertiary 2-haloacetamides |
| IT1144666B (it) * | 1980-03-25 | 1986-10-29 | Monsanto Co | Derivati di n-alcossimetil-2-aloacetanilidi erbicidi |
| FR2479201B1 (fr) * | 1980-03-25 | 1985-05-31 | Monsanto Co | Composes de n-hydrocarbyloxymethyl-2-haloacetanilides et compositions herbicides les renfermant |
-
1981
- 1981-03-18 CS CS811978A patent/CS226729B2/cs unknown
- 1981-03-18 LU LU83237A patent/LU83237A1/fr unknown
- 1981-03-18 IE IE594/81A patent/IE51103B1/en unknown
- 1981-03-18 RO RO109606A patent/RO85530B/ro unknown
- 1981-03-18 JP JP3807481A patent/JPS56145252A/ja active Pending
- 1981-03-18 FI FI810833A patent/FI73971C/fi not_active IP Right Cessation
- 1981-03-18 BR BR8101604A patent/BR8101604A/pt unknown
- 1981-03-18 MA MA19307A patent/MA19101A1/fr unknown
- 1981-03-18 GB GB8108376A patent/GB2072175B/en not_active Expired
- 1981-03-18 BG BG051261A patent/BG35893A3/xx unknown
- 1981-03-18 FR FR8105443A patent/FR2479205A1/fr active Granted
- 1981-03-18 DK DK120581A patent/DK120581A/da not_active Application Discontinuation
- 1981-03-18 ZA ZA00811801A patent/ZA811801B/xx unknown
- 1981-03-18 PL PL1981230200A patent/PL125377B1/pl unknown
- 1981-03-18 DE DE3110525A patent/DE3110525C2/de not_active Expired
- 1981-03-18 NZ NZ196540A patent/NZ196540A/xx unknown
- 1981-03-18 IL IL62409A patent/IL62409A/xx unknown
- 1981-03-18 DD DD81228414A patent/DD157298A5/de unknown
- 1981-03-18 AU AU68483/81A patent/AU536794B2/en not_active Ceased
- 1981-03-18 NL NL8101327A patent/NL8101327A/nl not_active Application Discontinuation
- 1981-03-18 CA CA000373323A patent/CA1221379A/en not_active Expired
- 1981-03-18 IT IT8120411A patent/IT1144661B/it active
- 1981-03-18 RO RO109605A patent/RO85529B/ro unknown
- 1981-03-18 GR GR64438A patent/GR66542B/el unknown
- 1981-03-18 ZW ZW58/81A patent/ZW5881A1/xx unknown
- 1981-03-18 HU HU81687A patent/HU189495B/hu unknown
- 1981-03-18 PT PT72678A patent/PT72678B/pt unknown
- 1981-03-18 SE SE8101729A patent/SE8101729L/ not_active Application Discontinuation
- 1981-03-18 AT AT0126081A patent/AT374659B/de not_active IP Right Cessation
- 1981-03-18 RO RO81103727A patent/RO81726A/ro unknown
- 1981-03-18 BE BE0/204162A patent/BE887995A/fr not_active IP Right Cessation
- 1981-03-18 NO NO810926A patent/NO151586C/no unknown
- 1981-03-18 CH CH184881A patent/CH645878A5/de not_active IP Right Cessation
- 1981-03-18 TR TR20885A patent/TR20885A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2029765C1 (ru) | Производные сим-триазинил сульфонилмочевины, композиция для борьбы с ростом нежелательной растительности и способ борьбы с ростом нежелательной растительности | |
| CA1295618C (en) | Insecticidal n'-substituted-n-acyl -n'-alkylcarbonylhydrazines | |
| CA1092153A (en) | Benzensulfonamide derivatives | |
| EP0171768A1 (en) | Substituted propargyloxyacetonitrile derivatives, process for production thereof, and herbicide and agricultural-horticultural fungicide comprising said derivatives as active ingredients | |
| US3403180A (en) | 4-trifluoromethyl-2, 6-dinitroanilines | |
| US4251263A (en) | N-substituted, 2-phenoxynicotinamide compounds and the herbicidal use thereof | |
| AU628349B2 (en) | Insecticidaln'-substituted-n-alkylcarbonyl-n'- acylhydrazines and n'-substituted-n-acyl-n'- alkylcarbonylhydrazines | |
| US3403994A (en) | Herbicidal method | |
| US4945113A (en) | herbicidal sulfonamide derivatives | |
| EP0205271B1 (en) | N-(3-chloro-4-isopropylphenyl)carboxamides, process for producing them, and selective herbicides containing them | |
| CA1221379A (en) | Herbicidal 2-haloacetanilides | |
| US3238222A (en) | (n-3, 4-disubstituted phenyl-3 and/or omega methyl-2-pyrrolidinones and piperidones) | |
| US4465509A (en) | Urea compounds and herbicidal compositions containing them | |
| US4353920A (en) | Use of selected 3-trihalomethyl-5-ureido-1,2,4-oxadiazoles and -1,2,4-thiadiazoles as agricultural viricides | |
| US4345938A (en) | Herbicidal 2-haloacetanilides | |
| GB2068949A (en) | 2-nitro-5-(substituted-phenoxy phenylalkanone oxime and imine derivatives as herbicides | |
| US4264777A (en) | Herbicidal diphenyl ether compound | |
| US4758263A (en) | 2-(2,5-difluorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5 diones | |
| US4761176A (en) | Herbicidal 2-haloacetanilides | |
| US4731109A (en) | Herbicidal 2-haloacetanilides | |
| CA1221380A (en) | Herbicidal 2-haloacetanilides | |
| US4579969A (en) | Substituted 1,3-dibenzylureas and herbicidal compositions containing them | |
| US4567299A (en) | Herbicidal 2-haloacetanilides | |
| US4606759A (en) | Herbicidal 2-haloacetanilides | |
| CA1206165A (en) | Herbicidal 2-haloacetanilides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20040505 |