GB1391515A - Herbicidal compositions based on 1,2,3-thiadiazol-5-yl ureas - Google Patents
Herbicidal compositions based on 1,2,3-thiadiazol-5-yl ureasInfo
- Publication number
- GB1391515A GB1391515A GB2920472A GB2920472A GB1391515A GB 1391515 A GB1391515 A GB 1391515A GB 2920472 A GB2920472 A GB 2920472A GB 2920472 A GB2920472 A GB 2920472A GB 1391515 A GB1391515 A GB 1391515A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiadiazol
- prepared
- reaction
- alkyl
- phenyl
- Prior art date
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1391515 4-Substituted-i ,2,3-thiadiazol-5-yI Ureas FMC CORP 22 June 1972 [23 June 1971 27 March 1972] 29204/72 Heading C2C The invention comprises herbicidal compounds of formula where A is a C 1 -C 4 alkyl or alkenyl radical; B is H or CH 3 but where A is other than CH 3 B is H; X is O or S; Y is -OR, -NHR , -NRR<SP>1</SP>, -NH-NH 2 or in which R<SP>1</SP> and R, which may be the same or different, are alkyl, alkenyl, alkynyl or cycloalkyl groups containing up to 12 carbon atoms and may also contain an ether linkage or a hydroxy substituent; Z is -O-, -CH 2 - or absent; and the metallic and amine salts thereof. These may be prepared by (a) aminolysis of phenyl (thiadiazol-5-yl) carbamates substituted in the 4-position with -COOR, e.g. to replace NHCOOPh by NHCON(CH 3 ) 2 ; (b) further aminating such products to replace COOR by CONHR or CONRR<SP>1</SP>; (c) ester interchange of products of (a); and (d) reacting a 4-carbonyl chloride with YH. Thioureas may be prepared by reaction of the corresponding urea with phosphorus pentasulphide, and the salts prepared by reaction with the corresponding base. Herbicidal compositions containing compounds of the invention are particularly effective in the presence of crops such as corn and peanuts. Phenyl (4-alkoxycarbonyl. 1 ,2,3-thiadiazol-5- yl)-carbamates are prepared by reaction of phenyl chloroformate with KSCN and an alkyl diazoacetate. 1,1 - Dimethyl - 3 - (4 - carboxy - 1,2,3- thiadiazol - 5 - yl) - urea was prepared by hydrolysis of its ethyl ester, and was converted to its acid chloride by reaction with 50C1 2 .
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15612571A | 1971-06-23 | 1971-06-23 | |
US23866472A | 1972-03-27 | 1972-03-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1391515A true GB1391515A (en) | 1975-04-23 |
Family
ID=26852893
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2920472A Expired GB1391515A (en) | 1971-06-23 | 1972-06-22 | Herbicidal compositions based on 1,2,3-thiadiazol-5-yl ureas |
Country Status (12)
Country | Link |
---|---|
AR (1) | AR193269A1 (en) |
BE (1) | BE785288A (en) |
CA (1) | CA969952A (en) |
DE (1) | DE2230905A1 (en) |
ES (1) | ES404179A1 (en) |
FR (1) | FR2144276A5 (en) |
GB (1) | GB1391515A (en) |
HU (1) | HU165687B (en) |
IL (1) | IL39536A (en) |
IT (1) | IT956535B (en) |
NL (1) | NL7208606A (en) |
OA (1) | OA04112A (en) |
-
1972
- 1972-05-23 CA CA142,738A patent/CA969952A/en not_active Expired
- 1972-05-25 IL IL39536A patent/IL39536A/en unknown
- 1972-06-13 IT IT25631/72A patent/IT956535B/en active
- 1972-06-21 HU HUFO653A patent/HU165687B/hu unknown
- 1972-06-21 FR FR7222327A patent/FR2144276A5/fr not_active Expired
- 1972-06-22 BE BE785288A patent/BE785288A/en unknown
- 1972-06-22 NL NL7208606A patent/NL7208606A/xx unknown
- 1972-06-22 OA OA54613A patent/OA04112A/en unknown
- 1972-06-22 GB GB2920472A patent/GB1391515A/en not_active Expired
- 1972-06-23 ES ES404179A patent/ES404179A1/en not_active Expired
- 1972-06-23 DE DE19722230905 patent/DE2230905A1/en active Pending
- 1972-07-22 AR AR242685A patent/AR193269A1/en active
Also Published As
Publication number | Publication date |
---|---|
DE2230905A1 (en) | 1972-12-28 |
ES404179A1 (en) | 1975-11-16 |
OA04112A (en) | 1979-11-30 |
NL7208606A (en) | 1972-12-28 |
IL39536A (en) | 1975-04-25 |
HU165687B (en) | 1974-10-28 |
BE785288A (en) | 1972-12-22 |
AR193269A1 (en) | 1973-04-11 |
CA969952A (en) | 1975-06-24 |
FR2144276A5 (en) | 1973-02-09 |
IT956535B (en) | 1973-10-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |