CA1183149A - Herbicide - Google Patents

Herbicide

Info

Publication number: CA1183149A
Authority: CA; Canada
Prior art keywords: alkyl; compound; halogen; coo; formula
Prior art date: 1974-04-10
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

CA000400497A

Other languages

English (en)

Inventor

Karl Matterstock

Peter Langeluddeke

Ernst-Friedrich Schulze

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1974-04-10

Filing date

1982-04-05

Publication date

1985-02-26

1974-04-10 Priority claimed from DE2417487A external-priority patent/DE2417487C2/de

1982-04-05 Application filed by Hoechst AG filed Critical Hoechst AG

1985-02-26 Application granted granted Critical

1985-02-26 Publication of CA1183149A publication Critical patent/CA1183149A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title description 10
230000002363 herbicidal effect Effects 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 26
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000002367 halogens Chemical group 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
150000007529 inorganic bases Chemical class 0.000 claims abstract description 5
150000007530 organic bases Chemical class 0.000 claims abstract description 5
150000001768 cations Chemical class 0.000 claims abstract description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 8
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
241000209504 Poaceae Species 0.000 claims description 20
244000038559 crop plants Species 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 10
-1 halo-(C1-C4)alkoxy Chemical group 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
150000003977 halocarboxylic acids Chemical class 0.000 claims description 2
230000000875 corresponding effect Effects 0.000 claims 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
229940125898 compound 5 Drugs 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
244000025254 Cannabis sativa Species 0.000 abstract description 9
239000004009 herbicide Substances 0.000 abstract description 8
125000005843 halogen group Chemical group 0.000 abstract 3
241000192043 Echinochloa Species 0.000 description 19
239000000126 substance Substances 0.000 description 19
241000196324 Embryophyta Species 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
240000007594 Oryza sativa Species 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
235000007164 Oryza sativa Nutrition 0.000 description 11
239000000047 product Substances 0.000 description 11
235000009566 rice Nutrition 0.000 description 11
239000004480 active ingredient Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
244000062793 Sorghum vulgare Species 0.000 description 9
239000013543 active substance Substances 0.000 description 9
241000894007 species Species 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
235000011684 Sorghum saccharatum Nutrition 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
159000000000 sodium salts Chemical class 0.000 description 8
230000006378 damage Effects 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000000843 powder Substances 0.000 description 7
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235000007320 Avena fatua Nutrition 0.000 description 6
244000068988 Glycine max Species 0.000 description 6
235000010469 Glycine max Nutrition 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
239000007900 aqueous suspension Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 6
240000001592 Amaranthus caudatus Species 0.000 description 5
235000009328 Amaranthus caudatus Nutrition 0.000 description 5
235000004535 Avena sterilis Nutrition 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
235000005775 Setaria Nutrition 0.000 description 5
241000232088 Setaria <nematode> Species 0.000 description 5
240000008042 Zea mays Species 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
YJKIALIXRCSISK-UHFFFAOYSA-N Chlorfenprop-methyl Chemical group COC(=O)C(Cl)CC1=CC=C(Cl)C=C1 YJKIALIXRCSISK-UHFFFAOYSA-N 0.000 description 4
240000005979 Hordeum vulgare Species 0.000 description 4
235000007340 Hordeum vulgare Nutrition 0.000 description 4
241000209082 Lolium Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
235000002017 Zea mays subsp mays Nutrition 0.000 description 4
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
235000005822 corn Nutrition 0.000 description 4
239000008187 granular material Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
240000000411 Sansevieria trifasciata Species 0.000 description 3
240000005498 Setaria italica Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical class O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 3
238000010410 dusting Methods 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
235000002252 panizo Nutrition 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000007921 spray Substances 0.000 description 3
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 description 3
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 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 2
240000008067 Cucumis sativus Species 0.000 description 2
235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
240000003176 Digitaria ciliaris Species 0.000 description 2
235000017898 Digitaria ciliaris Nutrition 0.000 description 2
235000005476 Digitaria cruciata Nutrition 0.000 description 2
235000006830 Digitaria didactyla Nutrition 0.000 description 2
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
235000014716 Eleusine indica Nutrition 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000209048 Poa Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
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239000000654 additive Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 2
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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239000003995 emulsifying agent Substances 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
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238000009331 sowing Methods 0.000 description 2
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QZEDXQFZACVDJE-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 QZEDXQFZACVDJE-UHFFFAOYSA-N 0.000 description 1
MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
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NPNHACUAJQMTLH-UHFFFAOYSA-N 4-[(2,4-dichlorophenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=C(Cl)C=C1Cl NPNHACUAJQMTLH-UHFFFAOYSA-N 0.000 description 1
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235000013311 vegetables Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA000400497A 1974-04-10 1982-04-05 Herbicide Expired CA1183149A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DEP2417487.6		1974-04-10
DE2417487A DE2417487C2 (de)	1974-04-10	1974-04-10	Benzyl-phenoxyalkancarbonsäuren, deren Derivate und Verfahren zu ihrer Herstellung
CA000224168A CA1170470A (fr)	1974-04-10	1975-04-09	Derives herbicides d'acide benzylphenoxy-alcane carboxylique

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000224168A Division CA1170470A (fr)	1974-04-10	1975-04-09	Derives herbicides d'acide benzylphenoxy-alcane carboxylique

Publications (1)

Publication Number	Publication Date
CA1183149A true CA1183149A (fr)	1985-02-26

Family

ID=25667898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000400497A Expired CA1183149A (fr)	1974-04-10	1982-04-05	Herbicide

Country Status (1)

Country	Link
CA (1)	CA1183149A (fr)

1982
- 1982-04-05 CA CA000400497A patent/CA1183149A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-02-26	MKEX	Expiry

Publication	Publication Date	Title
CA1170470A (fr)	1984-07-10	Derives herbicides d'acide benzylphenoxy-alcane carboxylique
US4332960A (en)	1982-06-01	Herbicidal compositions
CA1310970C (fr)	1992-12-01	Utilisation de derives quinoline pour la protection de plantes cultivees
JPH02174754A (ja)	1990-07-06	スルファモイルフェニル尿素
US4175947A (en)	1979-11-27	Phenoxy-phenoxypropionic acid esters
JPH0368862B2 (fr)	1991-10-30
IE44212B1 (en)	1981-09-09	Phenoxypropionic acid derivatives
US4123256A (en)	1978-10-31	N-(4-substituted benzyloxy)phenyl)-N-methyl-N-methoxyurea
JPS62292758A (ja)	1987-12-19	（ｒ）−２−〔４−（５−クロロ−３−フルオロピリジン−２−イルオキシ）−フエノキシ〕−プロピオン酸プロピニルエステル、その製造方法、並びに除草及び植物生長調節用組成物
US4648896A (en)	1987-03-10	2-aryl-4,6-dihalopyrimidines as antidote for protecting cultivated plants from phytotoxic damage caused by herbicides
CA1183149A (fr)	1985-02-26	Herbicide
US4025554A (en)	1977-05-24	Halogeno-acetanilides as herbicides
US3345151A (en)	1967-10-03	Herbicidal composition and method
US4412855A (en)	1983-11-01	2-Chloro-N-(2'-methoxypropyl)- and 2-chloro-N-(2'-ethoxypropyl)-2",6"-dimethyl-acetanilide as long term weed killers
EP0147477B1 (fr)	1987-11-04	Dérivés de pyridyloxybenzanilides et herbicides les contenant
JPS61180740A (ja)	1986-08-13	新規なフエニル酢酸又はフエニルチオ酢酸誘導体とそれを有効成分とする植物生育調節剤
US4163659A (en)	1979-08-07	Stunting plant growth with N-substituted perfluoroalkanesulfonamides
HU181430B (en)	1983-07-28	Process for preparing 3-chloro-2,6-dinitro-n-/substituted phenyl/-4-/trifluoro-methyl/-benzamine derivatives
CS209924B2 (en)	1981-12-31	Herbicide means and method of making the active component
JPS621921B2 (fr)	1987-01-16
US4509975A (en)	1985-04-09	Meta-anilide and meta-anilide urea herbicidal compounds and methods of use
KR790001079B1 (ko)	1979-08-26	벤질-페녹시알칸 카복실산의 제조방법
JPS60172949A (ja)	1985-09-06	アルコキシアミノ−またはポリアルコキシアミノジフエニルエ−テル、その製造方法及びそれを含有する除草剤組成物
US4489010A (en)	1984-12-18	Meta-anilide and meta-anilide urea and urea salt herbicidal compounds and methods of use
JPS6314714B2 (fr)	1988-04-01