GB1353399A - N,n-disubstituted amidoximes and their derivatives - Google Patents

N,n-disubstituted amidoximes and their derivatives

Info

Publication number
GB1353399A
GB1353399A GB3066971A GB3066971A GB1353399A GB 1353399 A GB1353399 A GB 1353399A GB 3066971 A GB3066971 A GB 3066971A GB 3066971 A GB3066971 A GB 3066971A GB 1353399 A GB1353399 A GB 1353399A
Authority
GB
United Kingdom
Prior art keywords
unsubstituted
halosubstituted
alkyl
aryl
represent
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
GB3066971A
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 GB1353399A publication Critical patent/GB1353399A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/409—Compounds containing the structure P(=X)-X-acyl, P(=X) -X-heteroatom, P(=X)-X-CN (X = O, S, Se)
    • C07F9/4096—Compounds containing the structure P(=X)-X-N (X = O, S, Se)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
    • C07F9/097—Compounds containing the structure P(=O)-O-N
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
    • C07F9/1657—Compounds containing the structure P(=X)n-X-N (X = O, S, Se; n = 0, 1)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32—Esters thereof
    • C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3264—Esters with hydroxyalkyl compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

1353399 Substituted amidoximes and derivatives thereof CIBA-GEIGY AG 30 June 1971 [1 July 1970] 30669/71 Headings C2C and C2P The invention comprises amidoximes of the general formula R 1 R 2 N-C(R 5 )=NOR, wherein R represents a hydrogen atom or a C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 monoalkylcarbamoyl, C 2 -C 6 dialkylcarbamoyl, C 6 -C 10 unsubstituted or halosubstituted arylcarbamoyl, C 1 -C 6 monoalkylthiocarbamoyl, C 2 -C 6 dialkylthiocarbamoyl, C 6 -C 10 arylthiocarbamoyl, unsubstituted or nitro- and trifluoromethyl-substituted C 6 -C 10 aryl, C 2 -C 6 acyl, C 1 -C 6 alkylsulphonyl or C 6 -C 10 arylsulphonyl group or a group of the formula: in which R 3 and R 4 , which may be the same or different, each represent a C 1 -C 6 unsubstituted or halosubstituted alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 unsubstituted or halosubstituted aryl, C 6 -C 10 aryloxy, C 6 -C 10 arylthio, C 7 -C 11 unsubstituted or halosubstituted arylalkyl and X represents an oxygen or sulphur atom; R 1 and R 2 , which may be the same or different, each represent a C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl group, or together with the N atom to which they are bonded represent a heterocyclic ring, and R 5 is a C 1 -C 6 unsubstituted or halosubstituted alkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 unsubstituted or halosubstituted aryl, C 7 -C 11 unsubstituted or halosubstituted arylalkyl group, or together with R 1 and the carbon and nitrogen atom to which they are respectively attached represents a heterocyclic ring with the proviso that R 1 and R 2 cannot both represent methyl groups when R is H and R 5 is phenyl. The compound in which R 1 and R 2 are each methyl, R 5 is phenyl and R is P(O)(OC 6 H 5 ) 2 is obtained by the following reaction steps: Other compounds may be obtained in an analogous manner using appropriate starting materials, the first two steps only being used for products in which R is H and the third step being also necessary when R is as defined (other than H), an appropriate compound RCl being used in this case. The amidoxime products in which R is an N-alkyl- or N-aryl-carbamoyl moiety can be obtained by reacting an amidoxime in which R is H with an appropriate isocyanate RNCO. The products have herbicidal properties and may be used as active ingredients in herbicidal compositions of conventional type which may also contain other pesticidal agents and fertilizers.
GB3066971A 1970-07-01 1971-06-30 N,n-disubstituted amidoximes and their derivatives Expired GB1353399A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US5168870A 1970-07-01 1970-07-01

Publications (1)

Publication Number Publication Date
GB1353399A true GB1353399A (en) 1974-05-15

Family

ID=21972792

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3066971A Expired GB1353399A (en) 1970-07-01 1971-06-30 N,n-disubstituted amidoximes and their derivatives

Country Status (14)

Country Link
US (1) US3717690A (en)
AT (1) AT307801B (en)
BE (1) BE769362A (en)
BG (1) BG18823A3 (en)
CA (1) CA965796A (en)
CH (1) CH562559A5 (en)
DD (1) DD98018A5 (en)
DE (1) DE2132598A1 (en)
FR (1) FR2098121A5 (en)
GB (1) GB1353399A (en)
IL (1) IL37193A (en)
NL (1) NL7109048A (en)
SU (1) SU399092A3 (en)
ZA (1) ZA714292B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4981544A (en) * 1972-12-08 1974-08-06
DE2320371A1 (en) * 1973-04-21 1974-11-07 Celamerck Gmbh & Co Kg THIOPHOSPHONIC ACID ESTER
US4125397A (en) * 1977-01-03 1978-11-14 Chevron Research Company O-Sulfonyl-alpha-halo-2,6-dihalobenzaldoximes
US4123255A (en) * 1977-01-03 1978-10-31 Chevron Research Company O-sulfonyl-alpha-cyano 2,6-dihalobenzaldoximes
US4323686A (en) * 1979-08-23 1982-04-06 Monsanto Company Benzothiazoleethanimidamides
US4283220A (en) * 1979-08-23 1981-08-11 Monsanto Company Imidamides derived from 2-oxo-3-benzothiazoline acetic acid plant growth regulants
US4525357A (en) * 1980-06-27 1985-06-25 Union Carbide Corporation Derivatives of bicyclic 2-iminothiazolidine oximes
US4479946A (en) * 1980-06-27 1984-10-30 Union Carbide Corporation Phosphorus esters of amidoximes, and compositions for and methods of controlling insects using them
US4405632A (en) * 1980-06-27 1983-09-20 Union Carbide Corporation Novel derivatives of bicyclic 2-iminothiazolidine oximes
US4339444A (en) * 1981-04-01 1982-07-13 Union Carbide Corporation Novel oxime-phosphate compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2816128A (en) * 1956-07-27 1957-12-10 Fmc Corp Phosphate esters of oximes
DE1196897B (en) * 1962-08-23 1965-07-15 Bayer Ag Rodenticidal agents

Also Published As

Publication number Publication date
IL37193A0 (en) 1971-08-25
NL7109048A (en) 1972-01-04
DD98018A5 (en) 1973-06-05
CA965796A (en) 1975-04-08
BG18823A3 (en) 1975-03-20
CH562559A5 (en) 1975-06-13
ZA714292B (en) 1972-03-29
FR2098121A5 (en) 1972-03-03
IL37193A (en) 1974-05-16
DE2132598A1 (en) 1972-01-05
AT307801B (en) 1973-06-12
BE769362A (en) 1972-01-03
US3717690A (en) 1973-02-20
SU399092A3 (en) 1973-09-27

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Legal Events

Date Code Title Description
48S Specification amended (sect. 8/1949)
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees