CA1210013A - 2-halogenoacetamides herbicides - Google Patents

2-halogenoacetamides herbicides

Info

Publication number: CA1210013A
Authority: CA; Canada
Prior art keywords: radical; compound; pyrazol; dimethyl; ylmethyl
Prior art date: 1980-12-01
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

Application number

CA000391186A

Other languages

English (en)

Inventor

John P. Chupp

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Monsanto Co

Original Assignee

Monsanto Co

Priority date (The priority date 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 date listed.)

1980-12-01

Filing date

1981-11-30

Publication date

1986-08-19

1981-11-30 Application filed by Monsanto Co filed Critical Monsanto Co

1986-08-19 Application granted granted Critical

1986-08-19 Publication of CA1210013A publication Critical patent/CA1210013A/fr

Status Expired legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title description 13
150000001875 compounds Chemical class 0.000 claims abstract description 69
125000002015 acyclic group Chemical group 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
125000001246 bromo group Chemical group Br* 0.000 claims abstract description 5
125000002346 iodo group Chemical group I* 0.000 claims abstract description 5
125000003226 pyrazolyl group Chemical class 0.000 claims abstract description 5
125000001425 triazolyl group Chemical class 0.000 claims abstract description 5
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
125000002883 imidazolyl group Chemical class 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 25
VJZOXIHNSXJJFQ-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylcyclohexen-1-yl)-n-(pyrazol-1-ylmethyl)acetamide Chemical compound CC1CCCC(C)=C1N(C(=O)CCl)CN1N=CC=C1 VJZOXIHNSXJJFQ-UHFFFAOYSA-N 0.000 claims description 4
229940126062 Compound A Drugs 0.000 claims 5
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 5
WUEMZIIALAGOJA-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylpent-2-en-3-yl)-N-(pyrazol-1-ylmethyl)acetamide Chemical compound CC(=C(C(C)C)N(C(CCl)=O)CN1N=CC=C1)C WUEMZIIALAGOJA-UHFFFAOYSA-N 0.000 claims 2
PMAQXXFBIIXMFX-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylcyclohexen-1-yl)-N-(1,2,4-triazol-1-ylmethyl)acetamide Chemical compound CC1=C(C(CCC1)C)N(C(CCl)=O)CN1N=CN=C1 PMAQXXFBIIXMFX-UHFFFAOYSA-N 0.000 claims 2
HMAJVEGVCPBDNE-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylcyclohexen-1-yl)-N-(imidazol-1-ylmethyl)acetamide Chemical compound CC1=C(C(CCC1)C)N(C(CCl)=O)CN1C=NC=C1 HMAJVEGVCPBDNE-UHFFFAOYSA-N 0.000 claims 2
UKDSOYQNYCVJCC-UHFFFAOYSA-N 2-chloro-n-(3-methylbut-2-en-2-yl)-n-(pyrazol-1-ylmethyl)acetamide Chemical compound CC(C)=C(C)N(C(=O)CCl)CN1C=CC=N1 UKDSOYQNYCVJCC-UHFFFAOYSA-N 0.000 claims 2
ZIEOQCSWXWNYOF-UHFFFAOYSA-N 2-chloro-N-(2,5-dimethylcyclopenten-1-yl)-N-(pyrazol-1-ylmethyl)acetamide Chemical compound CC1=C(C(CC1)C)N(C(CCl)=O)CN1N=CC=C1 ZIEOQCSWXWNYOF-UHFFFAOYSA-N 0.000 claims 1
239000004009 herbicide Substances 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 3
230000001747 exhibiting effect Effects 0.000 abstract 1
-1 N-azolylmethyl Chemical group 0.000 description 74
239000000203 mixture Substances 0.000 description 36
239000004480 active ingredient Substances 0.000 description 22
239000000047 product Substances 0.000 description 19
241000196324 Embryophyta Species 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
239000004606 Fillers/Extenders Substances 0.000 description 11
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
239000002689 soil Substances 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
239000007787 solid Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
125000004433 nitrogen atom Chemical group N* 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
239000004927 clay Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000002671 adjuvant Substances 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
229960000892 attapulgite Drugs 0.000 description 5
239000002270 dispersing agent Substances 0.000 description 5
229910052625 palygorskite Inorganic materials 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
239000000080 wetting agent Substances 0.000 description 5
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
235000013877 carbamide Nutrition 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
239000002245 particle Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 3
FDWNCOLDJCZPNR-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)acetamide Chemical compound ClCNC(=O)CCl FDWNCOLDJCZPNR-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
150000008061 acetanilides Chemical class 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
241000894007 species Species 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
240000000321 Abutilon grandifolium Species 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241001148727 Bromus tectorum Species 0.000 description 2
240000006122 Chenopodium album Species 0.000 description 2
235000009344 Chenopodium album Nutrition 0.000 description 2
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
240000001549 Ipomoea eriocarpa Species 0.000 description 2
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
229920001732 Lignosulfonate Polymers 0.000 description 2
235000003403 Limnocharis flava Nutrition 0.000 description 2
235000012629 Mentha aquatica Nutrition 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
240000000275 Persicaria hydropiper Species 0.000 description 2
235000017337 Persicaria hydropiper Nutrition 0.000 description 2
229920003171 Poly (ethylene oxide) Chemical class 0.000 description 2
235000004442 Polygonum persicaria Nutrition 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
244000067505 Xanthium strumarium Species 0.000 description 2
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
UIRJMLHBEQOZOJ-UHFFFAOYSA-N [N].CC(N)=O Chemical group [N].CC(N)=O UIRJMLHBEQOZOJ-UHFFFAOYSA-N 0.000 description 2
150000003869 acetamides Chemical class 0.000 description 2
229960001413 acetanilide Drugs 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
125000003710 aryl alkyl group 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
CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 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
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229940061627 chloromethyl methyl ether Drugs 0.000 description 2
239000002361 compost Substances 0.000 description 2
230000003750 conditioning effect Effects 0.000 description 2
125000000392 cycloalkenyl group Chemical group 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000000428 dust Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 2
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125000001188 haloalkyl group Chemical group 0.000 description 2
239000003864 humus Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
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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 2
235000014666 liquid concentrate Nutrition 0.000 description 2
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GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
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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 2
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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
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
HHBOUFYYHJJTNU-UHFFFAOYSA-N 1,3,6-thiadiazepane-2,7-dithione Chemical class S=C1NCCNC(=S)S1 HHBOUFYYHJJTNU-UHFFFAOYSA-N 0.000 description 1
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
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HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-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
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
OQIZZFNNHRWHCC-UHFFFAOYSA-N 2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxypropan-2-yl)acetamide 2-chloro-N-phenyl-N-propan-2-ylacetamide Chemical compound CC1=C(N(C(CCl)=O)C(C)(C)OC)C(=CC=C1)CC.C(C)C1=C(N(C(CCl)=O)COC)C(=CC=C1)CC.C(C)(C)N(C1=CC=CC=C1)C(CCl)=O OQIZZFNNHRWHCC-UHFFFAOYSA-N 0.000 description 1
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MGYVMWSVPYDBNK-UHFFFAOYSA-N 2-chloro-n-(3-methylbut-2-en-2-yl)acetamide Chemical compound CC(C)=C(C)NC(=O)CCl MGYVMWSVPYDBNK-UHFFFAOYSA-N 0.000 description 1
FVNMFOXLAIDRMW-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2,6-dimethylcyclohexen-1-yl)acetamide Chemical compound CC1CCCC(C)=C1N(CCl)C(=O)CCl FVNMFOXLAIDRMW-UHFFFAOYSA-N 0.000 description 1
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 1
101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
AXMJOLDHDBXYID-UHFFFAOYSA-N NC1=C(C(N(N=C1)C1=CC=CC=C1)=O)Cl.ClC1=NC(=NC(=N1)NCC)NCC.ClC1=NC(=NC(=N1)NC(C)C)NC(C)C.ClC1=NC(=NC(=N1)NCC)NC(C)C Chemical compound NC1=C(C(N(N=C1)C1=CC=CC=C1)=O)Cl.ClC1=NC(=NC(=N1)NCC)NCC.ClC1=NC(=NC(=N1)NC(C)C)NC(C)C.ClC1=NC(=NC(=N1)NCC)NC(C)C AXMJOLDHDBXYID-UHFFFAOYSA-N 0.000 description 1
JVMZCAFACAWHMQ-UHFFFAOYSA-N NC1=NNC=N1.CC1=NN=C(C(N1N)=O)C1=CC=CC=C1 Chemical compound NC1=NNC=N1.CC1=NN=C(C(N1N)=O)C1=CC=CC=C1 JVMZCAFACAWHMQ-UHFFFAOYSA-N 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
241000209117 Panicum Species 0.000 description 1
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
235000004443 Ricinus communis Nutrition 0.000 description 1
241000533293 Sesbania emerus Species 0.000 description 1
240000002439 Sorghum halepense Species 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
XJCLWVXTCRQIDI-UHFFFAOYSA-N Sulfallate Chemical compound CCN(CC)C(=S)SCC(Cl)=C XJCLWVXTCRQIDI-UHFFFAOYSA-N 0.000 description 1
WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
LPEFIBBNXNSFMB-UHFFFAOYSA-N [Na].ClC1=C(C#N)C(=CC=C1)Cl Chemical compound [Na].ClC1=C(C#N)C(=CC=C1)Cl LPEFIBBNXNSFMB-UHFFFAOYSA-N 0.000 description 1
230000009418 agronomic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000006231 alkoxy propyl group Chemical group 0.000 description 1
125000004848 alkoxyethyl group Chemical group 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000002518 antifoaming agent Substances 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
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
JAMFGQBENKSWOF-UHFFFAOYSA-N bromo(methoxy)methane Chemical compound COCBr JAMFGQBENKSWOF-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
RNWGYDIGXJHCHP-UHFFFAOYSA-L calcium;dodecane-1-sulfonate Chemical compound [Ca+2].CCCCCCCCCCCCS([O-])(=O)=O.CCCCCCCCCCCCS([O-])(=O)=O RNWGYDIGXJHCHP-UHFFFAOYSA-L 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 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
IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 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
IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 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
238000000921 elemental analysis Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
230000035784 germination Effects 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
230000012010 growth Effects 0.000 description 1
125000000262 haloalkenyl group Chemical group 0.000 description 1
125000000232 haloalkynyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052900 illite Inorganic materials 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000002386 leaching Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
QYPPRTNMGCREIM-UHFFFAOYSA-M methylarsonate(1-) Chemical compound C[As](O)([O-])=O QYPPRTNMGCREIM-UHFFFAOYSA-M 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910052901 montmorillonite Inorganic materials 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
150000002825 nitriles Chemical class 0.000 description 1
XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
150000002829 nitrogen Chemical class 0.000 description 1
VGIBGUSAECPPNB-UHFFFAOYSA-L nonaaluminum;magnesium;tripotassium;1,3-dioxido-2,4,5-trioxa-1,3-disilabicyclo[1.1.1]pentane;iron(2+);oxygen(2-);fluoride;hydroxide Chemical compound [OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[F-].[Mg+2].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[K+].[K+].[K+].[Fe+2].O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2 VGIBGUSAECPPNB-UHFFFAOYSA-L 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
238000003359 percent control normalization Methods 0.000 description 1
239000000575 pesticide 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
230000000704 physical effect Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229940072033 potash Drugs 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
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
229940043267 rhodamine b Drugs 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000002226 simultaneous effect Effects 0.000 description 1
229920005552 sodium lignosulfonate Polymers 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
239000012265 solid product Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- 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
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000391186A 1980-12-01 1981-11-30 2-halogenoacetamides herbicides Expired CA1210013A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US21160980A	1980-12-01	1980-12-01
US211,609		1980-12-01

Publications (1)

Publication Number	Publication Date
CA1210013A true CA1210013A (fr)	1986-08-19

Family

ID=22787637

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000391186A Expired CA1210013A (fr)	1980-12-01	1981-11-30	2-halogenoacetamides herbicides

Country Status (34)

Country	Link
JP (1)	JPS57120558A (fr)
AR (1)	AR227948A1 (fr)
AT (1)	AT381003B (fr)
AU (1)	AU542333B2 (fr)
BE (1)	BE891291A (fr)
BR (1)	BR8107776A (fr)
CA (1)	CA1210013A (fr)
CH (1)	CH650778A5 (fr)
CS (1)	CS226040B2 (fr)
DD (1)	DD201092A5 (fr)
DE (1)	DE3147400A1 (fr)
DK (1)	DK530081A (fr)
EG (1)	EG15686A (fr)
FI (1)	FI813830L (fr)
FR (1)	FR2495148A1 (fr)
GB (1)	GB2092131B (fr)
GR (1)	GR78298B (fr)
HU (1)	HU188304B (fr)
IL (1)	IL64403A (fr)
IT (1)	IT1195300B (fr)
KE (1)	KE3567A (fr)
MY (1)	MY8600280A (fr)
NL (1)	NL8105374A (fr)
NO (1)	NO814075L (fr)
NZ (1)	NZ199110A (fr)
PH (1)	PH19882A (fr)
PL (1)	PL130538B1 (fr)
PT (1)	PT74065B (fr)
RO (1)	RO83715B (fr)
SE (1)	SE8107143L (fr)
SU (1)	SU1228773A3 (fr)
TR (1)	TR21232A (fr)
ZA (1)	ZA818301B (fr)
ZW (1)	ZW29081A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3524918A1 (de) *	1985-07-12	1987-01-15	Basf Ag	Chinolin-8-carbonsaeureazolide, ein verfahren zu ihrer herstellung und ihre verwendung als herbizide

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2842315A1 (de) *	1978-09-28	1980-04-17	Bayer Ag	N-(1,2-azolyl)alkyl-halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2854598A1 (de) *	1978-12-18	1980-07-03	Basf Ag	N-substituierte carbonsaeureanilide, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
EP0029011A1 (fr) *	1979-11-13	1981-05-20	Ciba-Geigy Ag	N-(azolyl-1-éth-1'-yl)-halogénacétanilides, leur préparation et leur utilisation comme herbicides

1981
- 1981-11-24 AR AR287555A patent/AR227948A1/es active
- 1981-11-27 PH PH26547A patent/PH19882A/en unknown
- 1981-11-27 NL NL8105374A patent/NL8105374A/nl not_active Application Discontinuation
- 1981-11-30 EG EG703/81A patent/EG15686A/xx active
- 1981-11-30 FI FI813830A patent/FI813830L/fi not_active Application Discontinuation
- 1981-11-30 DD DD81235246A patent/DD201092A5/de not_active IP Right Cessation
- 1981-11-30 AU AU78109/81A patent/AU542333B2/en not_active Ceased
- 1981-11-30 CS CS818832A patent/CS226040B2/cs unknown
- 1981-11-30 GR GR66654A patent/GR78298B/el unknown
- 1981-11-30 CA CA000391186A patent/CA1210013A/fr not_active Expired
- 1981-11-30 DE DE19813147400 patent/DE3147400A1/de not_active Withdrawn
- 1981-11-30 NZ NZ199110A patent/NZ199110A/en unknown
- 1981-11-30 IL IL64403A patent/IL64403A/xx unknown
- 1981-11-30 GB GB8136034A patent/GB2092131B/en not_active Expired
- 1981-11-30 RO RO105906A patent/RO83715B/ro unknown
- 1981-11-30 FR FR8122416A patent/FR2495148A1/fr active Granted
- 1981-11-30 DK DK530081A patent/DK530081A/da not_active Application Discontinuation
- 1981-11-30 ZA ZA818301A patent/ZA818301B/xx unknown
- 1981-11-30 SE SE8107143A patent/SE8107143L/xx not_active Application Discontinuation
- 1981-11-30 PT PT74065A patent/PT74065B/pt unknown
- 1981-11-30 AT AT0513281A patent/AT381003B/de not_active IP Right Cessation
- 1981-11-30 CH CH7661/81A patent/CH650778A5/de not_active IP Right Cessation
- 1981-11-30 ZW ZW290/81A patent/ZW29081A1/xx unknown
- 1981-11-30 IT IT25350/81A patent/IT1195300B/it active
- 1981-11-30 BE BE0/206691A patent/BE891291A/fr not_active IP Right Cessation
- 1981-11-30 BR BR8107776A patent/BR8107776A/pt unknown
- 1981-11-30 SU SU813356856A patent/SU1228773A3/ru active
- 1981-11-30 NO NO814075A patent/NO814075L/no unknown
- 1981-11-30 HU HU813592A patent/HU188304B/hu unknown
- 1981-11-30 PL PL1981234034A patent/PL130538B1/pl unknown
- 1981-11-30 TR TR21232A patent/TR21232A/xx unknown
- 1981-11-30 JP JP56190947A patent/JPS57120558A/ja active Pending
1985
- 1985-10-08 KE KE3567A patent/KE3567A/xx unknown
1986
- 1986-12-30 MY MY280/86A patent/MY8600280A/xx unknown

Also Published As

Publication number	Publication date
AT381003B (de)	1986-08-11
CS226040B2 (en)	1984-03-19
DE3147400A1 (de)	1982-07-08
DD201092A5 (de)	1983-07-06
EG15686A (en)	1986-09-30
AU7810981A (en)	1982-06-10
PT74065A (en)	1981-12-01
ATA513281A (de)	1986-01-15
IT1195300B (it)	1988-10-12
PL130538B1 (en)	1984-08-31
GR78298B (fr)	1984-09-26
SU1228773A3 (ru)	1986-04-30
GB2092131B (en)	1985-06-26
MY8600280A (en)	1986-12-31
RO83715A (fr)	1984-10-31
ZA818301B (en)	1983-04-27
CH650778A5 (de)	1985-08-15
FR2495148B1 (fr)	1984-04-13
AR227948A1 (es)	1982-12-30
PL234034A1 (fr)	1982-07-05
SE8107143L (sv)	1982-07-12
AU542333B2 (en)	1985-02-21
HU188304B (en)	1986-04-28
IT8125350A0 (it)	1981-11-30
NL8105374A (nl)	1982-07-01
BR8107776A (pt)	1982-08-31
PH19882A (en)	1986-08-13
TR21232A (tr)	1984-02-06
BE891291A (fr)	1982-06-01
DK530081A (da)	1982-06-02
IL64403A0 (en)	1982-02-28
FR2495148A1 (fr)	1982-06-04
PT74065B (en)	1985-01-04
NZ199110A (en)	1984-10-19
JPS57120558A (en)	1982-07-27
RO83715B (ro)	1984-11-30
IL64403A (en)	1985-02-28
GB2092131A (en)	1982-08-11
ZW29081A1 (en)	1982-05-26
NO814075L (no)	1982-06-02
KE3567A (en)	1985-11-08
FI813830L (fi)	1982-06-02

Publication	Publication Date	Title
US4826529A (en)	1989-05-02	Substituted tetrazolinones and herbicidal compositions thereof
CA2092083C (fr)	1998-07-14	Derives de substitution d'arylhaloalkylpyrazoles herbicides
US5084083A (en)	1992-01-28	Herbicidal compositions
CA1162192A (fr)	1984-02-14	Derives d'aminopropiophenone, methodes de preparation et utilisation comme fongicides
PL115642B1 (en)	1981-04-30	Pesticide
US5675017A (en)	1997-10-07	Herbicidal substituted 3-aryl-pyrazoles
US4618679A (en)	1986-10-21	3,5-dicarboxylic acid esters of 2,6-bis(fluoro-alkyl)-2,6-bis(hydroxy) piperidines
US4622061A (en)	1986-11-11	Herbicidal 2-haloacetamides
CA1210013A (fr)	1986-08-19	2-halogenoacetamides herbicides
EP0295233A2 (fr)	1988-12-14	3-(4-Nitrophénoxy)pyrazoles et leur utilisation comme herbicides
US5045106A (en)	1991-09-03	Herbicidal substituted pyrazoles
US4451285A (en)	1984-05-29	Herbicidal 2-haloacetanilides
US4731451A (en)	1988-03-15	N-((2-oxo-3(2H)benzothiazolyl)methyl)-2-chloroacetanilides
US4461642A (en)	1984-07-24	Herbicidal compositions and method
US4345938A (en)	1982-08-24	Herbicidal 2-haloacetanilides
US4567299A (en)	1986-01-28	Herbicidal 2-haloacetanilides
US4242123A (en)	1980-12-30	Herbicidal composition and method of use
US4606759A (en)	1986-08-19	Herbicidal 2-haloacetanilides
US4816062A (en)	1989-03-28	Herbicidal compositions and method containing 3,5-dicarboxylic acid esters of 2,6-bis-(fluoro-alkyl) tetrahydropyrans
US4242122A (en)	1980-12-30	Herbicidal meta-bifunctional benzenes
US4055414A (en)	1977-10-25	Herbicidal composition and method of use
CA1131661A (fr)	1982-09-14	2-haloacetanilides alcoxyles en ortho, methode de preparation et utilisation comme herbicides
GB2072183A (en)	1981-09-30	Herbicidal 2-Haloacetanilides
GB2072655A (en)	1981-10-07	Novel ortho-alkoxy-substituted 2- haloacetanilides, their method of preparation and their use as herbicides
NZ203491A (en)	1985-07-12	1,4-thiazine derivatives and herbicidal compositions

Legal Events

Date	Code	Title	Description
2003-08-19	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20030819