CA1080498A - Herbicides - Google Patents

Herbicides

Info

Publication number: CA1080498A
Authority: CA; Canada
Prior art keywords: chloro; alkyl; hydrogen; halogen; methyl
Prior art date: 1972-11-17
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

CA314,271A

Other languages

English (en)

Inventor

Richard W. Feeny

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.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid 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.)

1972-11-17

Filing date

1978-10-25

Publication date

1980-07-01

1972-11-17 Priority claimed from US00307671A external-priority patent/US3857692A/en

1972-11-17 Priority claimed from US307670A external-priority patent/US3867403A/en

1973-10-23 Priority claimed from CA184,017A external-priority patent/CA1049536A/fr

1978-10-25 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1978-10-25 Priority to CA314,271A priority Critical patent/CA1080498A/fr

1980-07-01 Application granted granted Critical

1980-07-01 Publication of CA1080498A publication Critical patent/CA1080498A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 59
230000002363 herbicidal effect Effects 0.000 title claims abstract description 32
235000007320 Avena fatua Nutrition 0.000 claims abstract description 49
125000000217 alkyl group Chemical group 0.000 claims abstract description 47
241000196324 Embryophyta Species 0.000 claims abstract description 44
-1 dinitrophenyl Chemical group 0.000 claims abstract description 39
239000004009 herbicide Substances 0.000 claims abstract description 36
244000075850 Avena orientalis Species 0.000 claims abstract description 32
239000001257 hydrogen Substances 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
150000003839 salts Chemical class 0.000 claims abstract description 30
235000005373 Uvularia sessilifolia Nutrition 0.000 claims abstract description 29
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 28
229910052736 halogen Inorganic materials 0.000 claims abstract description 25
241001647031 Avena sterilis Species 0.000 claims abstract description 19
235000004535 Avena sterilis Nutrition 0.000 claims abstract description 18
244000025254 Cannabis sativa Species 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 13
150000001450 anions Chemical group 0.000 claims abstract description 8
WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 claims abstract description 6
150000003672 ureas Chemical class 0.000 claims abstract description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 12
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 11
WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 10
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 8
230000003054 hormonal effect Effects 0.000 claims description 8
241000209504 Poaceae Species 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 6
229910001413 alkali metal ion Inorganic materials 0.000 claims description 6
NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 claims description 5
UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 5
MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 claims description 4
HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical class C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
125000005210 alkyl ammonium group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
235000013877 carbamide Nutrition 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 4
150000003918 triazines Chemical class 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000006371 dihalo methyl group Chemical group 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000004970 halomethyl group Chemical group 0.000 claims description 3
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 3
125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 3
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 3
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
235000021317 phosphate Nutrition 0.000 claims description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
TXLBNHKWSHVQKP-UHFFFAOYSA-N (2-amino-3-methoxycarbonylphenyl)-(3-methylphenyl)carbamic acid Chemical compound COC(=O)C1=CC=CC(N(C(O)=O)C=2C=C(C)C=CC=2)=C1N TXLBNHKWSHVQKP-UHFFFAOYSA-N 0.000 claims 1
XZNZJDPPWWFJAL-UHFFFAOYSA-N 3,5-difluoro-4-hydroxybenzonitrile Chemical compound OC1=C(F)C=C(C#N)C=C1F XZNZJDPPWWFJAL-UHFFFAOYSA-N 0.000 claims 1
125000005189 alkyl hydroxy group Chemical group 0.000 claims 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 claims 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 abstract description 2
239000004202 carbamide Substances 0.000 abstract description 2
BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 abstract description 2
CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
150000001875 compounds Chemical class 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
239000004094 surface-active agent Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
229940022682 acetone Drugs 0.000 description 11
125000005843 halogen group Chemical group 0.000 description 8
239000003921 oil Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
229920000056 polyoxyethylene ether Polymers 0.000 description 6
239000007921 spray Substances 0.000 description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 5
241000209140 Triticum Species 0.000 description 5
235000021307 Triticum Nutrition 0.000 description 5
150000001768 cations Chemical class 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
230000009021 linear effect Effects 0.000 description 5
229940051841 polyoxyethylene ether Drugs 0.000 description 5
240000008100 Brassica rapa Species 0.000 description 4
235000011292 Brassica rapa Nutrition 0.000 description 4
235000004977 Brassica sinapistrum Nutrition 0.000 description 4
235000001602 Digitaria X umfolozi Nutrition 0.000 description 4
235000017898 Digitaria ciliaris Nutrition 0.000 description 4
235000005476 Digitaria cruciata Nutrition 0.000 description 4
235000006830 Digitaria didactyla Nutrition 0.000 description 4
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 4
235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
244000058871 Echinochloa crus-galli Species 0.000 description 4
244000025670 Eleusine indica Species 0.000 description 4
235000014716 Eleusine indica Nutrition 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000012085 test solution Substances 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
241000209764 Avena fatua Species 0.000 description 3
241000490495 Barbarea Species 0.000 description 3
235000007563 Barbarea vulgaris Nutrition 0.000 description 3
241001233845 Calepina Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
235000004431 Linum usitatissimum Nutrition 0.000 description 3
240000006240 Linum usitatissimum Species 0.000 description 3
239000005574 MCPA Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
238000003359 percent control normalization Methods 0.000 description 3
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
239000005504 Dicamba Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
244000020551 Helianthus annuus Species 0.000 description 2
235000003222 Helianthus annuus Nutrition 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
240000004713 Pisum sativum Species 0.000 description 2
235000010582 Pisum sativum Nutrition 0.000 description 2
229920001213 Polysorbate 20 Polymers 0.000 description 2
235000007238 Secale cereale Nutrition 0.000 description 2
244000082988 Secale cereale Species 0.000 description 2
240000003461 Setaria viridis Species 0.000 description 2
235000002248 Setaria viridis Nutrition 0.000 description 2
235000010086 Setaria viridis var. viridis Nutrition 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
229940077388 benzenesulfonate Drugs 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
230000009969 flowable effect Effects 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
229940031826 phenolate Drugs 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
239000011734 sodium Substances 0.000 description 2
WZZRJCUYSKKFHO-JTQLQIEISA-N (2s)-2-(n-benzoyl-3,4-dichloroanilino)propanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1N([C@@H](C)C(O)=O)C(=O)C1=CC=CC=C1 WZZRJCUYSKKFHO-JTQLQIEISA-N 0.000 description 1
BGCSXGXXLDPSHB-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;hydroxide Chemical compound [OH-].C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 BGCSXGXXLDPSHB-UHFFFAOYSA-M 0.000 description 1
GBNOSMRRYYJCFQ-UHFFFAOYSA-N 1h-pyrazole;hydrate Chemical compound O.C=1C=NNC=1 GBNOSMRRYYJCFQ-UHFFFAOYSA-N 0.000 description 1
BMTRHSLGCDHDNQ-UHFFFAOYSA-M 2,2-dichloropropanoate;1,2-dimethyl-3,5-diphenylpyrazol-1-ium Chemical compound CC(Cl)(Cl)C([O-])=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 BMTRHSLGCDHDNQ-UHFFFAOYSA-M 0.000 description 1
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
JVKIVZVZEUXPTI-UHFFFAOYSA-M 2-(2,4-dichlorophenoxy)acetate;1,2-dimethyl-3,5-diphenylpyrazol-1-ium Chemical compound [O-]C(=O)COC1=CC=C(Cl)C=C1Cl.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 JVKIVZVZEUXPTI-UHFFFAOYSA-M 0.000 description 1
HABAPWZXRLIZDL-UHFFFAOYSA-N 2-chloro-2-phenoxyacetic acid Chemical compound OC(=O)C(Cl)OC1=CC=CC=C1 HABAPWZXRLIZDL-UHFFFAOYSA-N 0.000 description 1
NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 1
239000004808 2-ethylhexylester Substances 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
DYBIGIADVHIODH-UHFFFAOYSA-N 2-nonylphenol;oxirane Chemical compound C1CO1.CCCCCCCCCC1=CC=CC=C1O DYBIGIADVHIODH-UHFFFAOYSA-N 0.000 description 1
CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
235000011635 Avena sterilis subsp ludoviciana Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
101100270918 Drosophila melanogaster Arp6 gene Proteins 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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
239000004698 Polyethylene Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241001148683 Zostera marina Species 0.000 description 1
238000010669 acid-base reaction Methods 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000009418 agronomic effect Effects 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000005224 alkoxybenzenes Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
125000006226 butoxyethyl group Chemical group 0.000 description 1
UQMRAFJOBWOFNS-UHFFFAOYSA-N butyl 2-(2,4-dichlorophenoxy)acetate Chemical compound CCCCOC(=O)COC1=CC=C(Cl)C=C1Cl UQMRAFJOBWOFNS-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
239000000969 carrier Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
125000003636 chemical group Chemical group 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
HIJIXCXMVYTMCY-UHFFFAOYSA-N diethyl 2-heptylpropanedioate Chemical compound CCCCCCCC(C(=O)OCC)C(=O)OCC HIJIXCXMVYTMCY-UHFFFAOYSA-N 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
239000004491 dispersible concentrate Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000002955 isolation Methods 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
ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
VXAPDXVBDZRZKP-UHFFFAOYSA-N nitric acid phosphoric acid Chemical compound O[N+]([O-])=O.OP(O)(O)=O VXAPDXVBDZRZKP-UHFFFAOYSA-N 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
230000035515 penetration Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000009951 qiqi Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA314,271A 1972-11-17 1978-10-25 Herbicides Expired CA1080498A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA314,271A CA1080498A (fr)	1972-11-17	1978-10-25	Herbicides

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US30768972A	1972-11-17	1972-11-17
US00307671A US3857692A (en)	1972-11-17	1972-11-17	1,2-dimethyl-3,5-diphenylpyrazolium salts and 3,5-dibromo-4-hydroxybenzonitrile herbicidal compositions
US307670A US3867403A (en)	1972-11-17	1972-11-17	1,2-dialkyl-3,5-diphenylpyrazolium salts
CA184,017A CA1049536A (fr)	1972-11-17	1973-10-23	Composes herbicides
CA314,271A CA1080498A (fr)	1972-11-17	1978-10-25	Herbicides

Publications (1)

Publication Number	Publication Date
CA1080498A true CA1080498A (fr)	1980-07-01

Family

ID=27508018

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA314,271A Expired CA1080498A (fr)	1972-11-17	1978-10-25	Herbicides

Country Status (1)

Country	Link
CA (1)	CA1080498A (fr)

1978
- 1978-10-25 CA CA314,271A patent/CA1080498A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-07-02	MKEX	Expiry

Publication	Publication Date	Title
US5403815A (en)	1995-04-04	Triazine derivative and a herbicide comprising the same as an effective ingredient
EP0184385A2 (fr)	1986-06-11	N-[(4,6-diméthoxypyrimidin-2-yl)aminocarbonyl]-3-trifluorométhylpyridine-2-sulfonamide ou ses sels, compositions herbicides le contenant et procédés pour la préparation du composé
JPH02501831A (ja)	1990-06-21	複素環化合物
DK155302B (da)	1989-03-28	N-phenylpyrazolderivater og herbicid med indhold deraf
US4626276A (en)	1986-12-02	Herbicidal trans-2-[(3-chloroallyloxyimino)alkyl]-5-(substitutedsulfinylalkyl)-cyclohexane-1,3-diones and derivatives thereof
HUT52771A (en)	1990-08-28	Herbicide compositions containing pyridine derivatives and process for producing the active components
CS226426B2 (en)	1984-03-19	Herbicide
US4113465A (en)	1978-09-12	Herbicidal formulations
US4235620A (en)	1980-11-25	Azolyl-substituted unsaturated ketones and herbicidal use thereof
US4406688A (en)	1983-09-27	Herbicidal 4-benzoyl-5-phenacyloxy-pyrazole derivatives, composition and method
US3922161A (en)	1975-11-25	Novel herbicidal compositions
CA1049536A (fr)	1979-02-27	Composes herbicides
CA1327578C (fr)	1994-03-08	Composes 2,4-diphenylpyrimidine substitues en 5, leur preparation et leur utilisation
CA1151655A (fr)	1983-08-09	5-amino-4-cyano-1-(2,4,6-trichlorophenyl) pyrazole et ses sels
US4170464A (en)	1979-10-09	Herbicidal combinations
EP0023725A1 (fr)	1981-02-11	Dérivés de diphényléther, procédé pour leur préparation et compositions herbicides les contenant
US3999974A (en)	1976-12-28	Barbituric acid derivatives
HU176749B (en)	1981-05-28	Herbicide compositions containing acetanilide derivatives and process for producing the active agents
US3929451A (en)	1975-12-30	Pre-emergence 1,2-dialkyl-3,5-disubstituted herbicidal compounds and method for using same
EP0647612A1 (fr)	1995-04-12	Aryloxybenzènes comme agents herbicides
US4192669A (en)	1980-03-11	Herbicidal ethers
US5090994A (en)	1992-02-25	Heterocyclic compounds and herbicidal compositions containing the compounds as effective components
US4447260A (en)	1984-05-08	N-Substituted phenyl-1-methylcyclopropanecarboxamides, and their herbicidal use
GB2103610A (en)	1983-02-23	Herbicidal compounds derived from N-sulphonyl-aryloxybenamides and the processes for their preparation and use
US4399072A (en)	1983-08-16	N-Phenyl-N-methylurea derivatives