CA2236592C - Synergistic herbicidal mixtures - Google Patents

Synergistic herbicidal mixtures Download PDF

Info

Publication number: CA2236592C
Authority: CA; Canada
Prior art keywords: rates; colby; dosage; mixtures; loo
Prior art date: 1995-11-15
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 - Lifetime

Application number

CA002236592A

Other languages

English (en)

French (fr)

Other versions

CA2236592A1 (en

Inventor

Richard Rees

Jurgen Bohner

Eberhard Richter

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.)

Yashima Chemical Industrial Co Ltd

Original Assignee

Hoechst Schering Agrevo GmbH

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.)

1995-11-15

Filing date

1996-11-12

Publication date

2005-01-04

1996-11-12 Application filed by Hoechst Schering Agrevo GmbH filed Critical Hoechst Schering Agrevo GmbH

1997-05-22 Publication of CA2236592A1 publication Critical patent/CA2236592A1/en

2005-01-04 Application granted granted Critical

2005-01-04 Publication of CA2236592C publication Critical patent/CA2236592C/en

2016-11-12 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 67
230000002363 herbicidal effect Effects 0.000 title claims abstract description 15
230000002195 synergetic effect Effects 0.000 title abstract description 49
241000196324 Embryophyta Species 0.000 claims abstract description 14
LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 claims abstract description 9
VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims abstract description 8
235000007164 Oryza sativa Nutrition 0.000 claims abstract description 8
QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 claims abstract description 7
JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 claims abstract description 7
UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 claims abstract description 7
MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 claims abstract description 7
ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims abstract description 7
-1 daimuro n Chemical compound 0.000 claims abstract description 7
ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 claims abstract description 7
VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 claims abstract description 7
BDQWWOHKFDSADC-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylphenoxy)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C)OC1=CC=C(Cl)C(C)=C1Cl BDQWWOHKFDSADC-UHFFFAOYSA-N 0.000 claims abstract description 6
NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 claims abstract description 6
239000005469 Azimsulfuron Substances 0.000 claims abstract description 6
OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 claims abstract description 6
BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 claims abstract description 6
UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 claims abstract description 6
LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 claims abstract description 6
QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims abstract description 6
WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims abstract description 6
239000004009 herbicide Substances 0.000 claims abstract description 6
DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 claims abstract description 6
FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 claims abstract description 6
FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 claims abstract description 6
235000009566 rice Nutrition 0.000 claims abstract description 6
239000005472 Bensulfuron methyl Substances 0.000 claims abstract description 5
239000005502 Cyhalofop-butyl Substances 0.000 claims abstract description 5
TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 claims abstract description 5
PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 claims abstract description 5
SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 claims abstract description 5
CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 claims abstract description 5
WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims abstract description 5
XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 claims abstract description 5
HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 claims abstract description 5
BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims abstract description 5
XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 claims abstract description 5
CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims abstract description 5
MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 claims abstract description 5
PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims abstract description 5
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 claims abstract description 5
239000005484 Bifenox Substances 0.000 claims abstract description 4
239000005574 MCPA Substances 0.000 claims abstract description 4
239000005588 Oxadiazon Substances 0.000 claims abstract description 4
239000005618 Sulcotrione Substances 0.000 claims abstract description 4
239000005567 Imazosulfuron Substances 0.000 claims abstract description 3
NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 claims abstract description 3
BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims abstract description 3
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims abstract description 3
NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 7
238000000034 method Methods 0.000 claims description 6
239000005476 Bentazone Substances 0.000 claims description 5
WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 claims description 5
YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 claims description 5
KDWQYMVPYJGPHS-UHFFFAOYSA-N Thenylchlor Chemical compound C1=CSC(CN(C(=O)CCl)C=2C(=CC=CC=2C)C)=C1OC KDWQYMVPYJGPHS-UHFFFAOYSA-N 0.000 claims description 5
CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 5
HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims description 5
QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 5
XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 claims description 5
239000005591 Pendimethalin Substances 0.000 claims description 3
241000209094 Oryza Species 0.000 claims 2
240000007594 Oryza sativa Species 0.000 abstract description 7
239000002253 acid Substances 0.000 abstract description 3
239000000470 constituent Substances 0.000 abstract 2
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150000002825 nitriles Chemical class 0.000 abstract 1
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239000000969 carrier Substances 0.000 description 4
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238000002360 preparation method Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
241000234653 Cyperus Species 0.000 description 3
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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150000003839 salts Chemical class 0.000 description 3
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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150000007513 acids Chemical class 0.000 description 2
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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241000232088 Setaria <nematode> Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
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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
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MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

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)

CA002236592A 1995-11-15 1996-11-12 Synergistic herbicidal mixtures Expired - Lifetime CA2236592C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19544393A DE19544393A1 (de)	1995-11-15	1995-11-15	Synergistische herbizide Mischungen
DE19544393.4		1995-11-15
PCT/EP1996/004935 WO1997017852A1 (de)	1995-11-15	1996-11-12	Synergistische herbizide mischungen

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1996
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- 1996-11-12 ES ES96938177T patent/ES2178720T3/es not_active Expired - Lifetime
- 1996-11-12 KR KR10-1998-0703305A patent/KR100427960B1/ko not_active Expired - Lifetime
- 1996-11-12 CN CN96198102A patent/CN1084148C/zh not_active Expired - Lifetime
- 1996-11-12 AU AU75696/96A patent/AU711841B2/en not_active Expired
- 1996-11-12 BR BR9611478A patent/BR9611478A/pt not_active IP Right Cessation
- 1996-11-12 US US09/068,137 patent/US6013605A/en not_active Expired - Lifetime
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- 1996-11-12 RU RU98111619/04A patent/RU2170017C2/ru not_active IP Right Cessation
- 1996-11-12 JP JP51856597A patent/JP3920341B2/ja not_active Expired - Lifetime
- 1996-11-12 DE DE59609348T patent/DE59609348D1/de not_active Expired - Fee Related
- 1996-11-12 TR TR1998/00794T patent/TR199800794T2/xx unknown
- 1996-11-12 EP EP96938177A patent/EP0863705B1/de not_active Expired - Lifetime
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- 1996-11-13 MY MYPI96004700A patent/MY114731A/en unknown
- 1996-11-14 ZA ZA969564A patent/ZA969564B/xx unknown
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1998
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Also Published As

Publication number	Publication date
AU711841B2 (en)	1999-10-21
JP2000500445A (ja)	2000-01-18
US6013605A (en)	2000-01-11
TR199800794T2 (xx)	1998-08-21
RU2170017C2 (ru)	2001-07-10
KR100427960B1 (ko)	2005-01-15
ES2178720T3 (es)	2003-01-01
MY114731A (en)	2002-12-31
CA2236592A1 (en)	1997-05-22
UA48203C2 (uk)	2002-08-15
KR19990067314A (ko)	1999-08-16
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Publication	Publication Date	Title
CA2236592C (en)	2005-01-04	Synergistic herbicidal mixtures
KR101068775B1 (ko)	2011-09-30	제초제 조성물
EP1209972B1 (en)	2003-05-28	Herbicidal composition
US5759955A (en)	1998-06-02	Herbicidal agents based on heteroaryloxyacetamides
AU2002311427B2 (en)	2007-11-22	Synergistic herbicidal compostions comprising mesotrione
HRP20010104A2 (en)	2002-02-28	Herbicides with acylated aminophenylsulfonyl urea
PL209961B1 (pl)	2011-11-30	Środki chwastobójcze zawierające podstawiony tien-3-ylosulfonyloamino(tio)karbonylotriazolin(ti)on, zastosowanie środków, sposób zwalczania niepożądanych roślin i sposób wytwarzania środków chwastobójczych
MXPA02004012A (es)	2002-10-23	Agentes herbicidas sinergisticos que contienen herbicidas del grupo de los inhibidores de hidroxifenilpiruvato dioxigenasa.
PL176089B1 (pl)	1999-04-30	Synergistyczny środek chwastobójczy oraz sposób zwalczania niepożądanej roślinności
PL220844B1 (pl)	2016-01-29	Kompozycja herbicydów na bazie sulfonylomoczników, sposób zwalczania szkodliwych roślin i zastosowanie kompozycji herbicydów
KR101148323B1 (ko)	2012-05-25	신규한 완화제 및 이의 용도
ZA200403326B (en)	2005-03-30	Synergistic herbicidal compositions comprising herbicides from the group of the benzoylpyrazoles
US6239070B1 (en)	2001-05-29	Herbicidal mixtures
AU652481B2 (en)	1994-08-25	Synergistic herbicidal compositions
JP3300008B2 (ja)	2002-07-08	除草剤組成物、および雑草を防除する方法
JPH04224504A (ja)	1992-08-13	除草作用を有する組成物および雑草を防除するための方法
KR100479612B1 (ko)	2005-06-17	1-(2-클로로-페닐)-4-(n-사이클로헥실-n-에틸-아미노카보닐)-1,4-디하이드로-5h-테트라졸-5-온및프로파닐을기본으로한선택적제초제
JPS59130803A (ja)	1984-07-27	トリアジン誘導体とレシチンまたはリノ−ル酸との組み合わせを含有する選択的除草剤
KR960007693B1 (ko)	1996-06-08	제초제
RU2269263C2 (ru)	2006-02-10	Синергетическое гербицидное средство, включающее 2-(4-тиокарбамоил-2-фтор-5-этилсульфониламино-фенил)-4-метил-5-трифторметил-2,4-дигидро-3н-1,2,4-триазол-3-он, и способ борьбы с нежелательными растениями
SI9200224A (en)	1993-03-31	Synergistic herbicidal compositions