PL86814B1 - - Google Patents

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Publication number
PL86814B1
PL86814B1 PL1973161700A PL16170073A PL86814B1 PL 86814 B1 PL86814 B1 PL 86814B1 PL 1973161700 A PL1973161700 A PL 1973161700A PL 16170073 A PL16170073 A PL 16170073A PL 86814 B1 PL86814 B1 PL 86814B1
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PL
Poland
Prior art keywords
formula
carbon atoms
alkyl radical
oxygen
group
Prior art date
Application number
PL1973161700A
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Polish (pl)
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.)
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Publication date
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Publication of PL86814B1 publication Critical patent/PL86814B1/pl

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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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/6533—Six-membered rings
    • 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
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • 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
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/59—Hydrogenated pyridine rings

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  • 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Przedmiotem wynalazku jest srodek owadobój¬ czy i roztoczobójczy zawierajacy jako substancje czynna nowe dwufpodstawdone N-/aminometyiide- no/-imidy estrów kwasów tMo/tiono/-fosforowych oraz znane nosniki. Wiadomo juz (ogloszeniowy opsls patentowy RFN nr 2 014 027) ze N-acetyloami- dy estrów kwasów 0,S-dwualkilotiolofosforowych, np. N-acetyloamid estru kwasu 0-metylo-lub -0- -etylo-S-metylotiolofosforowego, maja wlasciwosci owadobójcze i roztoczobójcze.Stwierdzono, ze nowe dwupodstawione N-/ami- nometylideno/-imidy estrów kwasów tiolo/tino/-fo- sforowych o wzorze 1, w którym R oznacza rodnik alkilowy o 1—6 atomach wegla, R' oznacza rodnik alkilowy o 1—6 atomach wegla, rodnik alkenylo- wy lub alkinylowy o 2—6 atomach wegla, grupe alkilomerkaptoalkilowa o 1—4 atomach wegla w kazdym rodniku alkilowym, lub grupe N-alkilo- karlbamoilometylowa, R" i Rw oznaczaja takie sa¬ me lub rózne rodniki alkilowe lub alkenylowe o 2—6 atomach wegla lub razem z atomem azotu moga tworzyc pierscien heterocykliczny, zawieraja¬ cy dodatkowe atomy tlenu, siarki lub azotu, a X oznacza atom* tlenu lub siarki, wykazuja doskonale dzialanie owadobójcze i roztoczobójcze.Nowe dwupodstawione N-/aminometylideno/- -imidy esltrów kwasów tiolo/tiono/^fosiforowych o wzonze 1 ottrzyimuje sie w sposób polegajacy na tym, ze a) estry alkilowe kwasów fosforyloimino- mrówkowych o wzorze 2, w którym R, R' i X maja wyzej podane znaczenie i Alk oznacza niz¬ szy rodnik alkilowy, poddaje sie reakcji z dru- gorzedowymi aminami o wzorze 3, w którym iR" i R"' ma wyzej podane znaczenlLe, lub b) amidy esitrów kfwaisu tiolo/tiono/-tfGstforowego o wzorze.4, w kltórym X, R i R' maja wyizejThe subject of the invention is an insecticide and acaricide containing as active ingredients new disubstituted N- (aminomethidide) -imides of t-Mo (thione) -phosphoric acid esters and known carriers. It is already known (German patent advertisement No. 2 014 027) that N-acetylamide esters of 0, S-dialkylthiolphosphoric acid esters, e.g. N-acetylamide ester of 0-methyl-or -O-ethyl-S-methylthiolophosphoric acid, have Insecticides and acaricides. It has been found that the new disubstituted N- (amino-methylidene) -imides of thiol / thino / -phosphoric acid esters of the formula I, in which R is an alkyl radical of 1-6 carbon atoms, R 'is an alkyl radical with 1-6 carbon atoms, alkenyl or alkynyl radical with 2-6 carbon atoms, alkylmercaptoalkyl group with 1-4 carbon atoms in each alkyl radical, or N-alkylcarbamoylmethyl group, R "and Rw are the same or various alkyl or alkenyl radicals with 2 to 6 carbon atoms or together with the nitrogen atom can form a heterocyclic ring containing additional oxygen, sulfur or nitrogen atoms, and X is oxygen or sulfur, exhibit excellent insecticidal and acaricidal activity. disubstituted N- (aminomethylidene) -imides thiol (thio) phosphoric acid esters of formula 1 are obtained in such a way that a) alkyl esters of phosphoryliminoformic acids of formula II, in which R, R 'and X have the meaning given above and Alk is the lower the alkyl radical is reacted with the secondary amines of formula III, in which R "and R" 'have the meanings given above, or b) thiol / thio / -tfGsthoric acid ester amides of formula 4, in which X, R and R 'are higher

Claims (1)

1. Zastrzezenie patentowe Srodek owadobójczy i roztoczobójczy, znamienny tym, ze jako substancje czynna zawiera dwupod- stawione N-/aminometylideno/-imidy estrów kwa¬ sów tiolo/tiono/-fosforowych o wzorze 1, w któ¬ rym R oznacza rodnik alkilowy o 1—6 atomach wegla, R' oznacza rodnik alkilowy o 1—6 atomach wegla, rodnik alkenylowy lub alkinylowy o 2—6 atomach wegla, grupe alkilomerkaptoalkilowa o 16 1—4 atomach wegla w kazdym rodniku alkilowym lub grupe N-alkilokarbamoilometylowa, R" i R'" oznaczaja takie same lub rózne rcdniki alkilowe lub alkenylowe o 2—6 atomach wegla lub razem z atomem azotu moga tworzyc pierscien hetero¬ cykliczny zawierajacy dodatkowo jako heteroato¬ my tlenu, siarki lub azotu, a X oznacza atom tlenu lub siarki, oraz znane rozcienczalniki i/lub srodki powierzchrtiowoczynne. ^Np-N-CH-r/*" R°)P-N-CH-0-Alk CH3O, S \p-N=CH-N(C2H5)2 CH3S/ Wzór i Wzór 2 Wzór 7 H-N / R" \d« P0v X }P-NH2 R'5/ C2H5O. 0 yh-H-CH-N(C2H5)2 CH3SX wzór 3 Wzór A Wzór 8 R«' X W\j? 9 OALk CW3S / P-NH-C-CH3 CH30^ 0 ^}P-N-CH-N(C2H5)2 Wzór 5 Wzór 6 Wzór 986 814 C* PLClaim 1. An insecticide and acaricide, characterized in that the active ingredient is di-substituted N- (aminomethylidene) -imides of thiol / thione / phosphoric acid esters of the formula I, in which R is an alkyl radical of 1-6 carbon atoms, R 'represents an alkyl radical of 1-6 carbon atoms, an alkenyl or alkynyl radical of 2-6 carbon atoms, an alkylmercaptoalkyl group of 16 1-4 carbon atoms in each alkyl radical or a N-alkylcarbamoylmethyl group, R " and R '"represent the same or different alkyl or alkenyl radicals with 2 to 6 carbon atoms or together with the nitrogen atom they can form a heterocyclic ring containing additionally oxygen, sulfur or nitrogen heteroatoms, and X represents an oxygen or sulfur atom, and known diluents and / or surfactants. ^ Np-N-CH-r / * "R °) PN-CH-0-Alk CH3O, S \ pN = CH-N (C2H5) 2 CH3S / Formula and Formula 2 Formula 7 HN / R" \ d «P0v X} P-NH2 R'5 / C2H5O. 0 yh-H-CH-N (C2H5) 2 CH3SX Formula 3 Formula A Formula 8 R «'X W \ j? 9 OALk CW3S / P-NH-C-CH3 CH30 ^ 0 ^} P-N-CH-N (C2H5) 2 Formula 5 Formula 6 Formula 986 814 C * PL
PL1973161700A 1972-04-06 1973-04-04 PL86814B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2216552A DE2216552C3 (en) 1972-04-06 1972-04-06 Disubstituted N- [aminomethylidene] -thiol- (thiono) -phosphoric acid esterimides, process for their preparation and their use as insecticides and acaricides

Publications (1)

Publication Number Publication Date
PL86814B1 true PL86814B1 (en) 1976-06-30

Family

ID=5841151

Family Applications (1)

Application Number Title Priority Date Filing Date
PL1973161700A PL86814B1 (en) 1972-04-06 1973-04-04

Country Status (21)

Country Link
JP (2) JPS4913122A (en)
AT (1) AT322908B (en)
BE (1) BE797792A (en)
BR (1) BR7302379D0 (en)
CH (1) CH582994A5 (en)
CS (2) CS183687B2 (en)
DD (1) DD107934A5 (en)
DE (1) DE2216552C3 (en)
DK (1) DK134320C (en)
EG (1) EG10754A (en)
ES (2) ES413374A1 (en)
FR (1) FR2179214B1 (en)
GB (1) GB1377329A (en)
HU (1) HU168160B (en)
IL (1) IL41933A (en)
IT (1) IT981879B (en)
NL (1) NL7304849A (en)
PL (1) PL86814B1 (en)
RO (2) RO62884A (en)
TR (1) TR17151A (en)
ZA (1) ZA732384B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RO65820A (en) * 1974-09-12 1980-06-15 Bayer A.G.,De PROCESS FOR PREPARING NEW PHOSPHORIC ESTERS
JPS5423479U (en) * 1977-07-19 1979-02-15
DE2737403A1 (en) * 1977-08-19 1979-02-22 Bayer Ag N- (AMINOMETHYLENE) - (MONO- AND DITHIO) -PHOSPHORSAEUREDIESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES
LU85892A1 (en) * 1985-05-10 1986-12-05 Wurth Paul Sa METHOD FOR CONTROLLING THE LOADING OF A TANK OVEN

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121084A (en) * 1962-09-17 1964-02-11 Du Pont Selected n, n, n'-trisubstituted amidines and their preparation by reaction of compounds with-nh2 groups with amide acetals
DE2118469C3 (en) * 1971-04-16 1980-02-14 Bayer Ag, 5090 Leverkusen N- (Dimenthylaminomethyliden) -thiol (thiono) phosphoric acid ester imides, process for their preparation and their use as insecticides and acaricides
BE792901A (en) * 1971-12-17 1973-06-18 Ciba Geigy PHOSPHOROUS AMIDINES AND PESTICIDE PRODUCTS CONTAINING THEM

Also Published As

Publication number Publication date
TR17151A (en) 1974-04-25
BR7302379D0 (en) 1974-02-07
IT981879B (en) 1974-10-10
DE2216552B2 (en) 1980-03-06
JPS4913336A (en) 1974-02-05
CH582994A5 (en) 1976-12-31
BE797792A (en) 1973-10-05
FR2179214A1 (en) 1973-11-16
CS183697B2 (en) 1978-07-31
AU5422973A (en) 1974-10-10
DE2216552C3 (en) 1980-10-30
ES413374A1 (en) 1976-06-16
IL41933A (en) 1977-10-31
IL41933A0 (en) 1973-06-29
DK134320C (en) 1977-04-12
EG10754A (en) 1976-11-30
DE2216552A1 (en) 1973-10-11
DD107934A5 (en) 1974-08-20
ES440270A1 (en) 1977-03-16
GB1377329A (en) 1974-12-11
DK134320B (en) 1976-10-18
RO62884A (en) 1978-01-15
CS183687B2 (en) 1978-07-31
AT322908B (en) 1975-06-10
RO65819A (en) 1981-07-30
JPS4913122A (en) 1974-02-05
ZA732384B (en) 1974-01-30
HU168160B (en) 1976-03-28
NL7304849A (en) 1973-10-09
FR2179214B1 (en) 1977-02-04

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