GB1330667A - N-o-fluorophenylureas their manufacture and their use - Google Patents

N-o-fluorophenylureas their manufacture and their use

Info

Publication number
GB1330667A
GB1330667A GB4861370A GB1330667DA GB1330667A GB 1330667 A GB1330667 A GB 1330667A GB 4861370 A GB4861370 A GB 4861370A GB 1330667D A GB1330667D A GB 1330667DA GB 1330667 A GB1330667 A GB 1330667A
Authority
GB
United Kingdom
Prior art keywords
denotes
alkyl
alkoxy
halogen
reacting
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
Application number
GB4861370A
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.)
Novartis AG
Original Assignee
Ciba Geigy 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.)
Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1330667A publication Critical patent/GB1330667A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

1330667 N-o-fluorophenylureas CIBAGEIGY AG 13 Oct 1970 [13 Oct 1969] 48613/70 Heading C2C [Also in Division A5] Novel N-o-fluorophenylureas of the general formula wherein X denotes O or S, R 1 denotes C 1-4 alkyl optionally substituted by halogen, CN, NO 2 or alkoxy, and/or which may be interrupted one or more times by -O-, -S-, -SO- or -SO 2 -, a C 2-4 alkenyl, optionally substituted by one or more halogen atoms, a C 3-4 alkynyl, -CHO or C 1-4 alkoxy; R 2 denotes H or C 1-4 alkyl, and R 3 , R 4 and R 5 , which may be the same or different, each represents a hydrogen or halogen atom, a C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio, C 1-2 halogenoalkyl, NO 2 , trihalogenomethylthio or sulphonamide group, a phenoxy radical, optionally substituted by one or more of halogen, alkyl, alkoxy, -NO 2 , -CN and -CF 3 groups, or a carbalkoxy radical, with the proviso that an unsubstituted alkyl represented by R 1 has 2 to 4 carbon atoms when R 3 , R 4 and R 5 each denotes a hydrogen atom and X denotes an oxygen atom, may be obtained by reacting an o-fluoro-R 3 , R 4 , R 5 -aniline (a) with phosgene or thiophosgene and reacting the resulting isocyanate or isothiocyanate with R 1 NHR 2 , or (b) with Z-CX-NR 1 R 2 (where Z is Cl, Br or I). N - (o - fluorophenyl) - N<SP>1</SP> - n - butylurea is made by reacting n-butylisocyanate and o-fluoroaniline, and may be converted to N-(o-fluoro-pbromophenyl) - N<SP>1</SP> - n - butylurea by bromination in the presence of glacial acetic acid and sodium acetate. The products have pesticidal, herbicidal and fungicidal activity.
GB4861370A 1969-10-13 1970-10-13 N-o-fluorophenylureas their manufacture and their use Expired GB1330667A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH1529769A CH532358A (en) 1969-10-13 1969-10-13 Herbicidal and fungicidal agent
GB4861370 1970-10-13
BE758433 1970-11-04

Publications (1)

Publication Number Publication Date
GB1330667A true GB1330667A (en) 1973-09-19

Family

ID=27159354

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4861370A Expired GB1330667A (en) 1969-10-13 1970-10-13 N-o-fluorophenylureas their manufacture and their use

Country Status (5)

Country Link
BE (1) BE758433A (en)
CH (1) CH532358A (en)
DE (1) DE2048660A1 (en)
FR (1) FR2065315A5 (en)
GB (1) GB1330667A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4313755A (en) * 1980-07-21 1982-02-02 Shell Oil Company N-Cyclopyopyl-N-(fluorophenyl)-N-acylureas and their herbidical use
CN107278570A (en) * 2017-07-10 2017-10-24 中国计量大学 A kind of method for promoting wild rice stem to tie hay in advance and increase production

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE791449A (en) * 1971-11-17 1973-05-16 Roussel Uclaf NEW SUBSTITUTED UREES AND PROCEDURE
IE62559B1 (en) * 1989-02-02 1995-02-08 Ici Plc Fungicides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4313755A (en) * 1980-07-21 1982-02-02 Shell Oil Company N-Cyclopyopyl-N-(fluorophenyl)-N-acylureas and their herbidical use
CN107278570A (en) * 2017-07-10 2017-10-24 中国计量大学 A kind of method for promoting wild rice stem to tie hay in advance and increase production

Also Published As

Publication number Publication date
CH532358A (en) 1973-01-15
FR2065315A5 (en) 1971-07-23
BE758433A (en) 1971-05-04
DE2048660A1 (en) 1971-06-24

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee