FR2310349A1 - S-Triazine (2,4)-dione herbicides prepn. - six-stage process begins with reactn. of alkyl chloroformates with cyanamide and ends with an intermediate guanidine ring closure (BR091176) - Google Patents

S-Triazine (2,4)-dione herbicides prepn. - six-stage process begins with reactn. of alkyl chloroformates with cyanamide and ends with an intermediate guanidine ring closure (BR091176)

Info

Publication number
FR2310349A1
FR2310349A1 FR7613377A FR7613377A FR2310349A1 FR 2310349 A1 FR2310349 A1 FR 2310349A1 FR 7613377 A FR7613377 A FR 7613377A FR 7613377 A FR7613377 A FR 7613377A FR 2310349 A1 FR2310349 A1 FR 2310349A1
Authority
FR
France
Prior art keywords
give
alkyl
cpd
treating
triazine
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.)
Granted
Application number
FR7613377A
Other languages
French (fr)
Other versions
FR2310349B1 (en
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of FR2310349A1 publication Critical patent/FR2310349A1/en
Application granted granted Critical
Publication of FR2310349B1 publication Critical patent/FR2310349B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Prepn. of triazine herbicides of formula (I): (where R' is 2-8C alkyl, 5-8C cycloalkyl, norbornyl, methylcyclohexyl, methylcyclopentyl, phenyl or chlorophenyl; R3 is Me; R4 is 1-4C alkyl) is by (a) treatingcyanamide with an alkyl chloroformate RO2C.Cl to give an alkoxycarbonylcyanamide; (b) treating the prod. with an alkylating agent CH3.Z to give an N-Alkoxy-carbonyl-N-methylcyanamide; (c) treating this cpd. with an amine salt of formula R3R4.NH2 +n.Yn-5 (where n is 1 when Y is Cl-; n is 2 when Y is SO4--) to give a cpd. of formula RO2CN(CH3)C(=NH2)NR3R4 + Yn-; (d) treating this cpd. with an alkali metal hydroxide to give a cpd. of formula: RO2CN(CH3)C(=NH)NR3R4; (e) removing unreacted amine R3R4NH; (f) treating the prod. from (d) with an isocyanate R1.NCO to give a cpd. RO2CN(CH3)C(=NCONHR') NR3R4; (g) treating the prod. with a base M1.OR5 to cyclise it and give (I). (where Z is Br, I or -O3S.OMe; M' is an alkali metal; R is 2-3 C alkyl, R5 is 1-4C alkyl). Process gives increased yields compared with the 5-s stage process of US 3850924, esp. when R is Et. In an example, 1a-methyl-4-cyclohexyl-6-dimethylamino-s-triazine-2, 4(1H,3H)dione was prepd.
FR7613377A 1975-05-05 1976-05-05 S-Triazine (2,4)-dione herbicides prepn. - six-stage process begins with reactn. of alkyl chloroformates with cyanamide and ends with an intermediate guanidine ring closure (BR091176) Granted FR2310349A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US57435175A 1975-05-05 1975-05-05
US67592176A 1976-04-15 1976-04-15

Publications (2)

Publication Number Publication Date
FR2310349A1 true FR2310349A1 (en) 1976-12-03
FR2310349B1 FR2310349B1 (en) 1980-11-07

Family

ID=27076366

Family Applications (2)

Application Number Title Priority Date Filing Date
FR7613377A Granted FR2310349A1 (en) 1975-05-05 1976-05-05 S-Triazine (2,4)-dione herbicides prepn. - six-stage process begins with reactn. of alkyl chloroformates with cyanamide and ends with an intermediate guanidine ring closure (BR091176)
FR7720924A Granted FR2349572A1 (en) 1975-05-05 1977-07-07 PERFECTED PROCESS FOR THE PREPARATION OF N- (CARBAMOYL N-SUBSTITUE-N ', N'-DIALCOYLAMIDINO) -N-ALKYL METHYLCARBAMATES

Family Applications After (1)

Application Number Title Priority Date Filing Date
FR7720924A Granted FR2349572A1 (en) 1975-05-05 1977-07-07 PERFECTED PROCESS FOR THE PREPARATION OF N- (CARBAMOYL N-SUBSTITUE-N ', N'-DIALCOYLAMIDINO) -N-ALKYL METHYLCARBAMATES

Country Status (8)

Country Link
AU (1) AU509813B2 (en)
BR (1) BR7602779A (en)
ES (1) ES447625A1 (en)
FR (2) FR2310349A1 (en)
IE (1) IE44369B1 (en)
MX (1) MX3778E (en)
PH (1) PH14092A (en)
PT (1) PT65067B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106380425A (en) * 2016-08-25 2017-02-08 宿迁市万和泰化工有限公司 Production process of N-(N-cyclohexylamide-N', N'-dmethyl amidine)-N-methyl ethyl carbamate
CN111763158B (en) * 2020-06-24 2022-09-09 江苏蓝丰生物化工股份有限公司 Preparation method of hexazinone intermediate guanidine compound and method for preparing hexazinone

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL42103A (en) * 1972-05-24 1976-05-31 Du Pont 6-amino-s-triazine-2,4-(1h,3h)-diones and corresponding 4-thio compounds,their preparation and their use as herbicides

Also Published As

Publication number Publication date
IE44369B1 (en) 1981-11-04
FR2349572B1 (en) 1981-01-02
ES447625A1 (en) 1977-10-01
FR2349572A1 (en) 1977-11-25
AU509813B2 (en) 1980-05-29
PT65067B (en) 1978-06-03
MX3778E (en) 1981-07-07
PT65067A (en) 1976-06-01
BR7602779A (en) 1976-11-09
PH14092A (en) 1981-02-10
IE44369L (en) 1976-11-05
FR2310349B1 (en) 1980-11-07
AU1362876A (en) 1977-11-10

Similar Documents

Publication Publication Date Title
GB1194835A (en) Novel 1-Amidino-3-Phenyl-Urea Derivatives, the preparation thereof and Compositions containing the same
GB1116694A (en) Novel nitrosocyanoalkylhydrazines
EP0098098A3 (en) Acridinecarboxamide compounds
FR2310349A1 (en) S-Triazine (2,4)-dione herbicides prepn. - six-stage process begins with reactn. of alkyl chloroformates with cyanamide and ends with an intermediate guanidine ring closure (BR091176)
NO923964L (en) ANTIMICROBIAL QUINOLONYL LACTANTS
US3755363A (en) Cyclic cyanodithioimidocarbonate and its preparation
ES364928A1 (en) Herbicidal 2-alkylthio-4 6-diamino-s-triazines
GB1386490A (en) Substituted s-triazines and their use as herbicides
GB1418247A (en) Sulphonyloxy-phenylureas process for their preparation and their use as herbicides
JPS56158797A (en) Novel d-allose derivative and antitumor agnet comprising it as active ingredient
MY117938A (en) (2-morpholinylmethyl) benzamide derivatives
GB1433690A (en) Regeneration of salt baths
GB923398A (en) Diphenyl mono-and bis-formyl guanylhydrazones
GB1083730A (en) Chromone and thiochromone guanylhydrazones
GB1418603A (en) Dichlorothiazolylureas processes for their preparation and their use as herbicides
FR2243936A1 (en) N-s-triazinyl urea herbicides - prepd from 2-amino triazine and alkyl isocyanate or carbamoyl halide
GB1029326A (en) Isoindoline-2-carboxylic acid amides
GB1326461A (en) S-triazine derivatives and their use as herbicides
GB1341486A (en) Process for the production of herbicidally active-2-alkylthio- 4,6-diamino-2-triazines
ES341320A1 (en) Process for the preparation of pyrazinoylguanidines
FR2224467A1 (en) 2-Chlor-4-alkylamin-6-cyanalkyl amino triazines derivs. - prepd. from cyanuric chloride and suitable ketone and ammonium salts
PT65225A (en) Process for preparing 3-(substituted)-2,6-dinitroanilines
ES370564A1 (en) Halo substituted uracils and hydrouracils and preparation of same
WO2003074524A3 (en) Mappicine analogs, intermediates in the synthesis of mappicine analogs and methods of synthesis of mappicine analogs
GB1311913A (en) Herbicidal hydroxyguanidines

Legal Events

Date Code Title Description
ST Notification of lapse