US3800037A - Insecticidal and acaricidal substituted carbanilic acid esters - Google Patents

Insecticidal and acaricidal substituted carbanilic acid esters Download PDF

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Publication number
US3800037A
US3800037A US00069887A US6988770A US3800037A US 3800037 A US3800037 A US 3800037A US 00069887 A US00069887 A US 00069887A US 6988770 A US6988770 A US 6988770A US 3800037 A US3800037 A US 3800037A
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United States
Prior art keywords
composition
compound
carbamate
propargyl
synergist
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 - Lifetime
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US00069887A
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English (en)
Inventor
H Martin
G Pissiotas
O Rohr
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Novartis Corp
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Ciba Geigy Corp
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Publication date
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Priority to US430284A priority Critical patent/US3860632A/en
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Publication of US3800037A publication Critical patent/US3800037A/en
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Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids

Definitions

  • ABSTRACT Substituted carbanilic acid propargyl esters of the formula in which R,, R and R., which may be the same or different, each represents a hydrogen atom or a halogen atom or an alkyl, alkoxy or halogenalkyl radical each having from one to four carbon atoms or a N0 or SCN group, and R and R which may be the same or different, each represents a hydrogen atom or an alkyl group having from one to four carbon atoms, used as synergistic agents for insecticidally and/or a acaricidally active substances.
  • R R and R which may be the same or different, each represents a hydrogen atom or a halogen atom or an alkyl, alkoxy or halogenalkyl radical each having from one to four carbon atoms or a NO or -SCN group, and R and R which may be the same or different, each represents a hydrogen atom or an alkyl group having from one to four carbon atoms.
  • alkyl and alkoxy groups which are represented by R,, R R R and R may be substituted or unsubstituted, branched or straight-chained. Suitable alkyl and alkoxy groups are, for example, methyl, ethyl and methoxy groups.
  • the compounds of the formula I may be prepared according to methods which are. in themselves, known. for example, by the reaction of an isocyanate of the formula in an inert solvent, for example, benzene, petroleum ether or dimethylformamide, the substituents R R R R and R having the same meanings as those specified for formula I. i
  • the compounds defined by the general formula .I are capable of increasing the activity of insecticidal and/or acaricidal compounds many-fold (synergism). Surprisingly, it has also been found that when using compounds of the formula I, insects or representatives of the order Acarina, which are resistant to carbamates or phosphoric acid esters, can be rendered completely sensitive to these latter compounds.
  • Suitable insecticidally or acaricidally active substances are, for example, the following compounds: 7
  • PHOSPI-IORIC ACID DERIVATIVES Bis-0,0-diethylphosphoric acid anhydride (TEPP) 0,0,0,0-Tetrapropyldithiopyrophosphate Dimethyl( 2,2,2-trichlorol hydroxyethyl )phosphonate (TRICHRORFON) v 1 ,2-Dibromol ,2dichlorethyldimethylphosphate (NALED) 2,2-Dichlorovinyldimethylphosphate F OS) 2-Methoxycarbamyll methylvinyldimethylphosphate (MEVINPI-IOS) Dimethyl-1-methyl-2-(methylcarbamoyl)vinylphosphate cis (MONOCROTOPHOS) 3-(Dimethoxyphosphinyloxy)-N-methyl-N-methoxycis-croton-amide 3-(Dimethoxyphosphinyloxy)-N,N-dimethyl-ciscrotohamide (DICROTOPI-I
  • the ratio of the insecticidally and/or acaricidally active substance to the compounds of the formula I is preferably within the range of from 0.01:10 to 200:1.
  • aphids such as the green peach aphid (Myzus persicae), and the black bean aphid (D0ralisfa bae); scale insects lice such as Aspidiotus hederae, Lecanium hesperidium, Pseudococcus maritimus; Thysanoptera such as Hercinothriosfemoralis, and bugs such as the beet bug (Piesma quadrata) or the bed bug (Cimex lectularius), caterpillars, such as Plutella maculipennis and Lymantria dispar; weevils such as the granary weevil (Calandra granaria) or the Colorado beelle (Leptinotarsa decemlineata), but also varieties which live in soil, such as wireworms (Agriotes sp.) or cockchafer grubs (Me
  • this synergistic mixture is also especially effective in combatting representatives of the order Acarina such as for example Eulaelaps, Echinolaelaps, Laelaps, Haemogamasus, Dermanyssus, Ornithonyssus, Allodermanyssus, in particular Allodermanyssus sanguineus, Pneumonyssus, Amblyomma, Aponomma, Boophilus, Dermacentor, Haemophysalis, Hyalomma, lxodes, Margaropus, Rhipicephalus, Ornithodorus; Octobius, Cheyletidae, for example Cheyletus, Psorergates, Demodicidae, Trombiculidae, for example Trombicula, Eutrombicula, Schongastia, Acomatacurus, Neoschongastia, Euschongastia, Sarcoptiformes for example Notoedre
  • Psoroptidae for example Psoroptes, Chorioptes, otodectes or Tetranychidae, for example Tetranychus telarius; Tetranychus urticae and the like.
  • the mixtures can either be used by themselves or together with suitable carriers and/or additives.
  • Suitable carriers and additives can be solid or liquid and correspond to the substances which are customary in formulation technology, for example, natural or regenerated mineral substances, solvents, dispersing agents, wetting agents, adhesives, thickeners, binders or fertilisers.
  • the methods of application depend on the end uses and must ensure that the active substance can be finely distributed.
  • the content of active substance in the preparations described above is between 01 and 95 percent. At the same time it should be mentioned that in the case of application from aircraft or by means of other suitable application instruments, concentrations of up to 99.5 percent or even a pure active substance may be employed.
  • solvents especially alcohols, for example ethyl alcohol or isopropyl alcohol, ketones, such as acetone or cyclohexanone, aliphatic hydrocarbons, such as kerosene, and cyclic hydrocarbons, such as benzene, toluene, xylene, tetrahydronaphthalene and alkylated naphthalenes, and also chlorinated hydrocarbons, such as tetrachloroethane, ethylene chloride, and finally also mineral and vegetable oils or mixtures of the above mentioned substances.
  • alcohols for example ethyl alcohol or isopropyl alcohol
  • ketones such as acetone or cyclohexanone
  • aliphatic hydrocarbons such as kerosene
  • cyclic hydrocarbons such as benzene, toluene, xylene, tetrahydronaphthalene and alkylated naphthalenes
  • Aqueous preparations are preferably dispersions'
  • the compounds of formula (I) and the active substance, as such or in one of the above mentioned solvents, are homogenised in water, preferably by means of wetting agents or dispersing agents.
  • cationic dispersing agents quaternary ammonium compounds may be mentioned as an example, and amongst anionic dispersing agents, soaps, aliphatic long-chain sulphuric acid monoesters, aliphatic-aromatic sulphonic acids and long-chain alkoxyacetic acids may for example be mentioned; amongst non-ionic dispersing agents, polyglycol ethers of fatty alcohols or ethylene oxide condensation products with p-tert. alkylphenols may be mentioned.
  • Dusting agents can be manufactured by mixing or conjoint grinding of the active substance and the synergistic agent with a solid carrier.
  • Possible carriers are for example: talc, diatomaceous earth, kaolin, bentonite, calcium carbonate, boric acid or tricalcium phosphate, but also wood flour, cork powder, charcoal and other materials of vegetable origin.
  • the substances can also be absorbed on the carriers by means of a volatile solvent.
  • Pulverulent preparations and pastes can be rendered capable of suspension in water, and usable as spraying agents, by the addition of wetting agents and protective colloids.
  • Emulsion Concentrate The easily soluble mixture of active substance and synergistic agentcan also be formulated as an emulsion concentrate in accordance with the following instruction:
  • Granules 7.5 g of a mixture of active substance and synergistic agent are dissolved in 100 ml of acetone and the acetone solution thus obtained is addedto 92 g of granular attapulgite. The whole is well mixed and the solvent is stripped off in a rotary evaporator. Granules containing 7.5 percent of active substance are obtained.
  • results listed in the table represent average values of the percentage destruction of female house flies, from two repeat experiments.
  • An insecticidal and acaricidal composition consisting essentially of equal parts by weight of l) 2-(1,3'-
  • a synergist compound selected from the group consisting of N-( 2-nitrophenyl )-propargyl carbamate, N-( 2-bromopheny1 )-propargyl carbamate, N-( 3-bromophenyl)propargyl carbamate, N-( 2- chlorophenyl propargyl carbamate, N-( 4-chlorophenyl)-propargyl carbamate, N-(2,3-dichlorophenyl)- propargyl carbamate, N-(2.5-dichlorophenyl)proparmethyl-3-chlorophenyl)-propargyl carbamate, N-(2,5- dimethylphenyl)-propargyl carbamate and N-(2- chloro-S-trifluoromethylphenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(2-nitrophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(2-bromophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N( 3-bromophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(2-chlorophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(4-chlorophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(2,3-dichlorophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(2,S-dichlorophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(3,S-dichlorophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(2,4,5-trichlorophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(3-trifluoromethylphenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(3-methylpheny1)-propargyl carbamate.
  • composition of claim 13 in which the synergist compound is N-(4-fluorophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(2-methyl-3-chlorophenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(2,5-dimethylphenyl)-propargyl carbamate.
  • composition of claim 1 in which the synergist compound is N-(2-chloro-5-trifluoromethylphenyl)- propargyl carbamate.
  • An insecticidal and acaricidal composition consisting essentially of equal parts by weight of l) a pesticidal compound selected from the group consisting of l-naphthyl-Nmethyl carbamate, 2-isopropoxyphenyl- N-methyl carbamate, l-Isopropyl-3-methylpyrazol- 5-yl-N,N-dimethyl carbamate, 2- [Propargylmethylamino]-phenyl-N-methylcarbamate, 0,0-Dimethyl-S- (1,2-dicarbethoxyethyl) dithiophosphate, 2-Chloro-2-diethylcarbamoyl- 1 -methlvinyldimethylphosphate, 0,0-Dimethyl-S-[ Z-methoxyl,3,4-thiadiazol-5 (4H)-onyl-4-methyl]dithiophosphate and pyrethrum and (2) N-(2-nitrophenyl)- propargyl carbamate.
  • composition of claim 17 in which the pesticidal compound is l-naphthyl-N-methyl carbamate.
  • composition of claim 17 in which the pesticidal compound is 2-isopropoxyphenyl-N-methyl carbamate.
  • composition of claim 17 in which the pesticidal compound is l-lsopropyl-3-methylpyrazol-5-yl- N,N-dimethylcarbamate.
  • composition of claim 17 in which the pesticidal compound is 2-[propargylmethylamino]-phenyl-N- methylcarbamate.
  • composition of claim 17 in which the pestici dal compound is 0,0-Dimethyl-S-( l ,2-dicarbethoxyethyl) dithiophosphate.
  • composition of claim 17 in which the pesticidal methylvinyldimethylphosphate is pesticidal methylvinyldimethylphosphate.
  • composition of claim 17 in which the pesticidal compound is. O, O Dimethyl-S-[Z-methoxy-l ,3,4-
  • Patent No. 3 a 800 Q Dated Inventor(s) H y rtln 01: a1

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US00069887A 1969-09-04 1970-09-04 Insecticidal and acaricidal substituted carbanilic acid esters Expired - Lifetime US3800037A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US430284A US3860632A (en) 1969-09-04 1974-01-02 N-o-nitrophenylpropargyl-carbamate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1342069A CH526907A (de) 1969-09-04 1969-09-04 Verwendung bestimmter Urethane als Synergisten zu insektizid und/oder akarizid wirkenden Stoffen

Publications (1)

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US3800037A true US3800037A (en) 1974-03-26

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US00069887A Expired - Lifetime US3800037A (en) 1969-09-04 1970-09-04 Insecticidal and acaricidal substituted carbanilic acid esters

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US (1) US3800037A (de)
AT (1) AT303452B (de)
AU (1) AU1951870A (de)
BE (1) BE755687A (de)
BG (1) BG17701A3 (de)
CH (1) CH526907A (de)
DE (1) DE2041986A1 (de)
FR (1) FR2060394B1 (de)
GB (2) GB1329680A (de)
IL (1) IL35193A0 (de)
NL (1) NL7013066A (de)
ZA (1) ZA705956B (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58126856A (ja) * 1982-01-19 1983-07-28 Sumitomo Chem Co Ltd Ｎ―フェニルカーバメート系化合物を有効成分とする農園芸用殺菌剤
JPS58192859A (ja) * 1982-05-04 1983-11-10 Sumitomo Chem Co Ltd Ｎ―フェニルカーバメート系化合物およびそれを有効成分とする農園芸用殺菌剤
US4482546A (en) * 1981-04-16 1984-11-13 Sumitomo Chemical Company, Limited Fungicidal N-phenylcarbamates
WO1992001381A1 (en) * 1990-07-18 1992-02-06 Formulogics, Inc. Method of preparing mixtures of active ingredients and excipients using liquid carbon dioxide
LU102907B1 (en) * 2022-02-03 2023-08-03 Eternygen Uk Ltd C/O Epidarex Capital Citrate transporter modulators and uses thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4977186A (en) * 1988-11-23 1990-12-11 Troy Chemical Corporation Wood preservative and soil treatment composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2526660A (en) * 1946-07-06 1950-10-24 Rohm & Haas Capryldintrophenyl crotonate
GB681376A (en) * 1949-11-23 1952-10-22 Geigy Ag J R Manufacture of heterocyclic carbamic acid derivatives and their use as agents for combating pests
US2788268A (en) * 1955-03-17 1957-04-09 Columbia Southern Chem Corp Novel compositions and their use
US2903478A (en) * 1958-08-07 1959-09-08 Union Carbide Corp alpha-naphthol bicyclic aryl esters of n-substituted carbamic acids
US2990318A (en) * 1958-10-23 1961-06-27 Fmc Corp Synergistic insecticidal compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2526660A (en) * 1946-07-06 1950-10-24 Rohm & Haas Capryldintrophenyl crotonate
GB681376A (en) * 1949-11-23 1952-10-22 Geigy Ag J R Manufacture of heterocyclic carbamic acid derivatives and their use as agents for combating pests
US2788268A (en) * 1955-03-17 1957-04-09 Columbia Southern Chem Corp Novel compositions and their use
US2903478A (en) * 1958-08-07 1959-09-08 Union Carbide Corp alpha-naphthol bicyclic aryl esters of n-substituted carbamic acids
US2990318A (en) * 1958-10-23 1961-06-27 Fmc Corp Synergistic insecticidal compositions

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
The Merck Index, 8th Ed., Merch & Co., Inc. 1968, p. 149. *
The Merck Index, 8th Ed., Merch & Co., Inc. 1968, p. 639. *
The Merck Index, 8th Ed., Merch & Co., Inc. 1968, pp. 30 31. *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4482546A (en) * 1981-04-16 1984-11-13 Sumitomo Chemical Company, Limited Fungicidal N-phenylcarbamates
JPS58126856A (ja) * 1982-01-19 1983-07-28 Sumitomo Chem Co Ltd Ｎ―フェニルカーバメート系化合物を有効成分とする農園芸用殺菌剤
JPS58192859A (ja) * 1982-05-04 1983-11-10 Sumitomo Chem Co Ltd Ｎ―フェニルカーバメート系化合物およびそれを有効成分とする農園芸用殺菌剤
WO1992001381A1 (en) * 1990-07-18 1992-02-06 Formulogics, Inc. Method of preparing mixtures of active ingredients and excipients using liquid carbon dioxide
LU102907B1 (en) * 2022-02-03 2023-08-03 Eternygen Uk Ltd C/O Epidarex Capital Citrate transporter modulators and uses thereof

Also Published As

Publication number Publication date
AU1951870A (en) 1972-03-09
AT303452B (de) 1972-11-27
GB1329680A (en) 1973-09-12
ZA705956B (en) 1971-04-28
DE2041986A1 (de) 1971-03-11
CH526907A (de) 1972-08-31
GB1318439A (en) 1973-05-31
NL7013066A (de) 1971-03-08
FR2060394A1 (de) 1971-06-18
FR2060394B1 (de) 1973-08-10
IL35193A0 (en) 1970-10-30
BE755687A (fr) 1971-03-03
BG17701A3 (bg) 1973-12-25

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