CA1093093A - Chloromethanesulphonic acid anilides and their use as herbicides - Google Patents

Chloromethanesulphonic acid anilides and their use as herbicides

Info

Publication number: CA1093093A
Authority: CA; Canada
Prior art keywords: trifluoromethyl; acid; compound; anilide; reaction
Prior art date: 1977-01-28
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

CA295,807A

Other languages

English (en)

French (fr)

Inventor

Erich Klauke

Engelbert Kuhle

Ludwig Eue

Robert R. Schmidt

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.)

Bayer AG

Original Assignee

Bayer 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.)

1977-01-28

Filing date

1978-01-27

Publication date

1981-01-06

1978-01-27 Application filed by Bayer AG filed Critical Bayer AG

1981-01-06 Application granted granted Critical

1981-01-06 Publication of CA1093093A publication Critical patent/CA1093093A/en

Status Expired legal-status Critical Current

Links

239000004009 herbicide Substances 0.000 title abstract description 7
SGDAONFFHUCRON-UHFFFAOYSA-N 1-chloro-n-phenylmethanesulfonamide Chemical class ClCS(=O)(=O)NC1=CC=CC=C1 SGDAONFFHUCRON-UHFFFAOYSA-N 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 21
MRLIHNLUQICROR-UHFFFAOYSA-N 1-chloro-n-[2-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound FC(F)(F)C1=CC=CC=C1NS(=O)(=O)CCl MRLIHNLUQICROR-UHFFFAOYSA-N 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 54
241000196324 Embryophyta Species 0.000 claims description 22
229920000742 Cotton Polymers 0.000 claims description 4
238000002360 preparation method Methods 0.000 abstract description 8
230000002363 herbicidal effect Effects 0.000 abstract description 5
239000000203 mixture Substances 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 22
-1 chloromethanesulphonic acid 2-trifluoromethyl-4-methylthio-aniline Chemical compound 0.000 description 19
239000003085 diluting agent Substances 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
KQDDQXNVESLJNO-UHFFFAOYSA-N chloromethanesulfonyl chloride Chemical compound ClCS(Cl)(=O)=O KQDDQXNVESLJNO-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000002253 acid Substances 0.000 description 12
230000003647 oxidation Effects 0.000 description 11
238000007254 oxidation reaction Methods 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
ZMHBBQHIIBIBHS-UHFFFAOYSA-N 4-methylsulfanyl-2-(trifluoromethyl)aniline Chemical compound CSC1=CC=C(N)C(C(F)(F)F)=C1 ZMHBBQHIIBIBHS-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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HNJFFPINMBLUBB-UHFFFAOYSA-N 1-chloro-N-[4-methylsulfanyl-2-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound FC(C1=C(NS(=O)(=O)CCl)C=CC(=C1)SC)(F)F HNJFFPINMBLUBB-UHFFFAOYSA-N 0.000 description 4
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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239000000370 acceptor Substances 0.000 description 3
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150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
HMPHJJBZKIZRHG-UHFFFAOYSA-N chloromethanesulfonic acid Chemical compound OS(=O)(=O)CCl HMPHJJBZKIZRHG-UHFFFAOYSA-N 0.000 description 3
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244000272323 Cirsium lanceolatum Species 0.000 description 2
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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
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239000010941 cobalt Substances 0.000 description 1
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150000002430 hydrocarbons Chemical class 0.000 description 1
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229910052742 iron Inorganic materials 0.000 description 1
DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
229920000126 latex Polymers 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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235000012054 meals Nutrition 0.000 description 1
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235000019713 millet Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
229940042472 mineral oil Drugs 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
NKUXJZGXSINEMP-UHFFFAOYSA-N n-propan-2-yl-1,3,5-triazin-2-amine Chemical compound CC(C)NC1=NC=NC=N1 NKUXJZGXSINEMP-UHFFFAOYSA-N 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
239000002420 orchard Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003090 pesticide formulation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
229960003351 prussian blue Drugs 0.000 description 1
239000013225 prussian blue Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
235000009736 ragweed Nutrition 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000011435 rock Substances 0.000 description 1
239000003128 rodenticide Substances 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000013589 supplement Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides

Landscapes

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

CA295,807A 1977-01-28 1978-01-27 Chloromethanesulphonic acid anilides and their use as herbicides Expired CA1093093A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19772703477 DE2703477A1 (de)	1977-01-28	1977-01-28	Chlormethansulfonsaeureanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DEP2703477.1		1977-01-28

Publications (1)

Publication Number	Publication Date
CA1093093A true CA1093093A (en)	1981-01-06

Family

ID=5999761

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA295,807A Expired CA1093093A (en)	1977-01-28	1978-01-27	Chloromethanesulphonic acid anilides and their use as herbicides

Country Status (18)

Country	Link
JP (1)	JPS5395940A (de)
AT (1)	AT357361B (de)
AU (1)	AU516367B2 (de)
BE (1)	BE863388A (de)
BR (1)	BR7800504A (de)
CA (1)	CA1093093A (de)
DE (1)	DE2703477A1 (de)
DK (1)	DK41178A (de)
EG (1)	EG12964A (de)
FR (1)	FR2378754A1 (de)
GB (1)	GB1566842A (de)
HU (1)	HU178434B (de)
IL (1)	IL53887A (de)
IT (1)	IT7819681A0 (de)
NL (1)	NL7800899A (de)
SU (1)	SU654143A3 (de)
TR (1)	TR19388A (de)
ZA (1)	ZA78509B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2845997A1 (de) *	1978-10-23	1980-04-30	Bayer Ag	Pflanzenwachstumsregulierende mittel, verfahren zu ihrer herstellung und ihre verwendung zur regulierung des pflanzenwachstums
DE2845996A1 (de) *	1978-10-23	1980-04-30	Bayer Ag	Herbizide mittel, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von unkraeutern
ZA80273B (en) *	1979-01-29	1981-03-25	Minnesota Mining & Mfg	4-phenylthioalkanesulfonanilides and derivatives thereof
ZA80274B (en) *	1979-01-29	1981-03-25	Minnesota Mining & Mfg	Substituted-4-alkylthioalkane-sulfonanilides and derivatives thereof
US4913728A (en) *	1979-01-29	1990-04-03	Minnesota Mining And Manufacturing Company	Substituted-4-alkylthioalkane-sulfonanilides and operatives
FR2447371A1 (fr) *	1979-01-29	1980-08-22	Minnesota Mining & Mfg	Nouveaux alcanesulfonanilides substitues sur l'azote, composition les contenant et leur application a la modification de la croissance des vegetaux superieurs

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1188591A (fr) *	1956-12-08	1959-09-23	Bayer Ag	Agents de protection contre les parasites des matières textiles et contre l'attaque des bactéries et des moisissures
CH510386A (de) *	1969-04-30	1971-07-31	Ciba Geigy Ag	Verwendung von Halogenmethylsulfanylverbindungen als selektive Herbizide
US3996277A (en) *	1974-11-14	1976-12-07	Minnesota Mining And Manufacturing Company	4-Methylthio-2-trifluoromethylmethanesulfonanilide and derivatives thereof

1977
- 1977-01-28 DE DE19772703477 patent/DE2703477A1/de not_active Withdrawn
1978
- 1978-01-18 SU SU782566500A patent/SU654143A3/ru active
- 1978-01-24 AU AU32675/78A patent/AU516367B2/en not_active Expired
- 1978-01-24 GB GB2818/78A patent/GB1566842A/en not_active Expired
- 1978-01-25 IL IL53887A patent/IL53887A/xx unknown
- 1978-01-25 NL NL7800899A patent/NL7800899A/xx not_active Application Discontinuation
- 1978-01-26 HU HU78BA3621A patent/HU178434B/hu unknown
- 1978-01-26 AT AT56478A patent/AT357361B/de not_active IP Right Cessation
- 1978-01-26 JP JP679078A patent/JPS5395940A/ja active Pending
- 1978-01-26 IT IT7819681A patent/IT7819681A0/it unknown
- 1978-01-26 TR TR19388A patent/TR19388A/xx unknown
- 1978-01-27 DK DK41178A patent/DK41178A/da unknown
- 1978-01-27 ZA ZA00780509A patent/ZA78509B/xx unknown
- 1978-01-27 CA CA295,807A patent/CA1093093A/en not_active Expired
- 1978-01-27 BR BR7800504A patent/BR7800504A/pt unknown
- 1978-01-27 BE BE184682A patent/BE863388A/xx unknown
- 1978-01-27 FR FR7802376A patent/FR2378754A1/fr not_active Withdrawn
- 1978-01-28 EG EG53/78A patent/EG12964A/xx active

Also Published As

Publication number	Publication date
AU516367B2 (en)	1981-05-28
BR7800504A (pt)	1978-09-12
SU654143A3 (ru)	1979-03-25
NL7800899A (nl)	1978-08-01
ATA56478A (de)	1979-11-15
HU178434B (en)	1982-05-28
DK41178A (da)	1978-07-29
AU3267578A (en)	1979-08-02
IL53887A (en)	1981-06-29
BE863388A (fr)	1978-07-27
IL53887A0 (en)	1978-04-30
EG12964A (en)	1980-07-31
AT357361B (de)	1980-07-10
JPS5395940A (en)	1978-08-22
TR19388A (tr)	1979-02-20
IT7819681A0 (it)	1978-01-26
GB1566842A (en)	1980-05-08
DE2703477A1 (de)	1978-08-03
ZA78509B (en)	1978-12-27
FR2378754A1 (fr)	1978-08-25

Legal Events

Date	Code	Title	Description
1998-01-06	MKEX	Expiry

Publication	Publication Date	Title
JP2744064B2 (ja)	1998-04-28	スルホニルアミノカルボニルトリアゾリノン類
US5344814A (en)	1994-09-06	Herbidical 1-(3,4-disubstituted phenyl) tetrazolinones
US4517011A (en)	1985-05-14	N-substituted halogenoacetanilides and their use as herbicides
EP0572855A1 (de)	1993-12-08	1-(3-Halogen-4-substituiertes Phenyl)Tetrazolinonderivate, deren Herstellung und Verwendung als Herbizide
EP0571855A1 (de)	1993-12-01	1-(3-Halogen-4-Trifluormethyl-Phenyl)Tetrazolinonderivate, deren Herstellung und Verwendung als Herbizide
CA1093093A (en)	1981-01-06	Chloromethanesulphonic acid anilides and their use as herbicides
JPH0369906B2 (de)	1991-11-05
US4067724A (en)	1978-01-10	N-(1,2,4-Triazin-5-on-4-yl)-glycines and herbicidal compositions
US4328029A (en)	1982-05-04	N-Pyrimidinylmethyl-haloacetanilide compounds and herbicidal compositions
US4384881A (en)	1983-05-24	Herbicidally active novel benzazol-2-yloxyacetanilides
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