US3846466A - Esters of di-(thiocarbamoyl)ethylene as juvenile hormone mimicking agents for control of insects - Google Patents
Esters of di-(thiocarbamoyl)ethylene as juvenile hormone mimicking agents for control of insects Download PDFInfo
- Publication number
- US3846466A US3846466A US00257092A US25709272A US3846466A US 3846466 A US3846466 A US 3846466A US 00257092 A US00257092 A US 00257092A US 25709272 A US25709272 A US 25709272A US 3846466 A US3846466 A US 3846466A
- Authority
- US
- United States
- Prior art keywords
- sulfur
- carbon atoms
- alkyl
- compound
- hydrogen
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/18—Esters of dithiocarbamic acids
- C07C333/20—Esters of dithiocarbamic acids having nitrogen atoms of dithiocarbamate groups bound to hydrogen atoms or to acyclic carbon atoms
Definitions
- ABSTRACT Compounds having the formula in which R is alkyl having 1 to 8 carbon atoms, R is hydrogen or alkyl having 1 to 4 carbon atoms, R is hydrogen or alkyl having 1 to 4 carbon atoms, R is alkyl having I to 8 carbon atoms, X is oxygen or sulfur and X is oxygen or sulfur.
- the compounds of the present invention are believed to have the further advantages that they are non-toxic to warm blooded animals and are highly effective in controlling insects at low dosages.
- One embodiment of the present invention is concerned with novel pesticidal compositions.
- the invention is concerned with the active pesticidal component of such compositions.
- the invention is concerned with a process for controlling insects by hindering or impeding the metamorphosis and reproduction of the insects.
- the compounds of the present invention that are useful in controlling insects are those having the formula in which R is alkyl having 1 to 8 carbon atoms, preferably 2 to 6 carbon atoms; R is hydrogen or alkyl having I to 4 carbon atoms, preferably hydrogen; R is hydrogen or, preferably, alkyl having 1 to 4 carbon atoms, preferably 1 to 3 carbon atoms; R is alkyl having 1 to 8 carbon atoms, preferably 2 to 6 carbon atoms; X is' oxygen or sulfur and X is oxygen or sulfur.
- the above compounds are useful in impeding the metamorphosis and/or the reproduction of-insects.
- the activity of the compounds is such that insects at any stage of their development can be effectively treated therewith.
- the compounds of this invention can be prepared by the following reaction:
- the reaction is carried out in a solvent such as water, with stirring by slowing adding the alkyl chloro(thio)formate or mixture of alkyl chloro(thio)- formates to the diamine in the presence of an acid acceptor, such as a solution of NaOH, at a temperature around 0C. followed by stirring at room temperature to complete the exothermic reaction.
- an acid acceptor such as a solution of NaOH
- the reaction product is recovered by conventional techniques such as extracting with methylene chloride, washing the solvent phase with water, followed by drying with anhydrous MgSO Finally, the solvent is filtered and removed by vacuum stripping.
- the reaction is carried out using equal mole amounts of the reactants, although a slight excess of a reactant can be used.
- Example I v N,N-diethyl-l ,2-bis(n-propylthiocarbamoyl) ethane C2115 C2H5 2.9 grams (0.025 mole), N,N-diethyl ethylene diamine, 25 milliliters water, 4.0 grams (50 percent) NaOH solution (0.05 mole) are mixed in a 3-neck flask equipped with a dropping funnel and a mechanical stirrer and stirring in an ice bath. 6.9 grams (0.05 mole) n-propylchlorothiolformate are slowly dropped into the mixture causing a exothermic reaction. The ice bath is removed and the reaction mixture is stirred at room temperature for A hour.
- reaction product is recovered by extracting with 100 milliliters c1-nc1, and then washing it with milliliters water, followed by drying with MgSO The organic phase is filtered and stripped by yield 6.9 grams of the desired product.
- N P-1.5022. LR. and n.m.r. analysis confirm the structure.
- the degree of activity of a candidate compound to hinder or impede the metamorphosis of insects is measured by treating the penultimate larval stage of a representative insect with the compound and examining it after its last molt toward the adult form for retention of immature features.
- the compounds of this invention are generally embodied-into a form suitable for convenient application.
- the compounds can be embodied into pesticidal composition which are provided in the form of emulsions, suspensions, solutions, dusts, and aerosol sprays.
- such compositions will contain, in addition to the active compound, the adjuvants which are found normally in pesticide preparations.
- the active compounds of this invention can be employed as the sole pesticide component or they can be used in admixture with other compounds having similar utility.
- the pesticide compositions of this invention can contain, as adjuvants, organic solvents, such as sesame oil, xylene range solvents, heavy petroleum, etc., water; emulsifying agents; surface active agents; talc; pyrophyllite; diatomite; gypsum; clays; propellants, such as dichlorodifluoromethane, etc.
- organic solvents such as sesame oil, xylene range solvents, heavy petroleum, etc.
- emulsifying agents such as sesame oil, xylene range solvents, heavy petroleum, etc.
- surface active agents such as sesame oil, xylene range solvents, heavy petroleum, etc.
- talc emulsifying agents
- pyrophyllite pyrophyllite
- diatomite gypsum
- clays gypsum
- propellants such as dichlorodifluoromethane
- Thecompounds can also be combined with baits in a conventional manner.
- the active pesticide compound will be embodied in the form of a liquid composition, for example, an emulsion, suspension, or aerosol spray. While the concentration of the active pesticide in the present compositions can vary within rather wide limits, ordinarily the pesticide compound will comprise not more than about 50 percent by weight of the composition. Preferably, however, the pesticide compositions of this invention will be in the form of solutions or suspensions containing about 0.1 to 1.0 percent by weight of the active pesticide compound.
- R is alkyl having 2 to 6 carbon atoms;
- R is hydrogen or alkyl having 1 to 4 carbon atoms;
- R is alkyl having 1 to 4 carbon atoms;
- R is alkyl having 2 to 6 carbon atoms;
- X is sulfur and X is sulfur.
- R is alkyl having 2 to 6 carbon atoms
- R is hydrogen
- R is alkyl having 1 to 3 carbon atoms
- R is alkyl having 2 to 6 carbon atoms
- X is sulfur and X is sulfur.
- R is alkyl having 2 to 6 carbon atoms
- R is alkyl having 1 to 3 carbon atoms
- R is alkyl having 1 to 3 carbon atoms
- R is alkyl having 2 to 6 carbon atoms
- X is sulfur and X is sulfur.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (20)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00257092A US3846466A (en) | 1972-05-26 | 1972-05-26 | Esters of di-(thiocarbamoyl)ethylene as juvenile hormone mimicking agents for control of insects |
AR248182A AR204508A1 (es) | 1972-05-26 | 1973-01-01 | Compuesto de 1,2-bis(alquil(tio)carbamoil)etano plaguicida sin accion terapeutica |
GB2097473A GB1385602A (en) | 1972-05-26 | 1973-05-03 | Certain non-terpenoid juvenile hormone mimicking compounds and their use in controlling insects |
DE2324020A DE2324020A1 (de) | 1972-05-26 | 1973-05-12 | Nicht-terpenoide, das juvenilhormon nachahmende verbindungen und deren verwendung zur insektenbekaempfung |
ZA733452A ZA733452B (en) | 1972-05-26 | 1973-05-22 | Certain non-terpenoid juvenile hormone mimicking compounds and their use in controlling insects |
CA171,963A CA1010052A (en) | 1972-05-26 | 1973-05-22 | Certain non-terpenoid juvenile hormone mimicking compounds and their use in controlling insects |
CS3675A CS178426B2 (es) | 1972-05-26 | 1973-05-22 | |
JP48056430A JPS4941529A (es) | 1972-05-26 | 1973-05-22 | |
AU56042/73A AU469589B2 (en) | 1972-05-26 | 1973-05-23 | Certain non-terpenoid juvenile hormone mimicking compounds and their use in controlling insects |
CH736573A CH574209A5 (es) | 1972-05-26 | 1973-05-23 | |
FR7318977A FR2189386B1 (es) | 1972-05-26 | 1973-05-24 | |
GT197328916A GT197328916A (es) | 1972-05-26 | 1973-05-24 | Ciertos compuestos plaguicidas |
IT50192/73A IT985198B (it) | 1972-05-26 | 1973-05-24 | Composti di etano metodo per prepararli ed insetticidi che li contengono |
NL7307336A NL7307336A (es) | 1972-05-26 | 1973-05-25 | |
IL42356A IL42356A0 (en) | 1972-05-26 | 1973-05-25 | Non-terpenoid juvenile hormone mimicking compounds and their use in controlling insects |
DD171091A DD104695A5 (es) | 1972-05-26 | 1973-05-25 | |
BE131536A BE800053A (fr) | 1972-05-26 | 1973-05-25 | Composes non terpenoides contrefaisant des hormones juveniles et leur utilisation dans la destruction d'insectes |
BR3867/73A BR7303867D0 (pt) | 1972-05-26 | 1973-05-25 | Processo de fabricacao de compostos pesticidas bem como de controle de insetos |
RO7374927A RO71925A (ro) | 1972-05-26 | 1973-05-26 | Procedeu de preparare a unor derivati ai acidului tiocarbonic |
US491919A US3917844A (en) | 1972-05-26 | 1974-07-25 | Certain non-terpenoid juvenile hormone mimicking compounds and their use in controlling insects |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00257092A US3846466A (en) | 1972-05-26 | 1972-05-26 | Esters of di-(thiocarbamoyl)ethylene as juvenile hormone mimicking agents for control of insects |
Publications (1)
Publication Number | Publication Date |
---|---|
US3846466A true US3846466A (en) | 1974-11-05 |
Family
ID=22974851
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00257092A Expired - Lifetime US3846466A (en) | 1972-05-26 | 1972-05-26 | Esters of di-(thiocarbamoyl)ethylene as juvenile hormone mimicking agents for control of insects |
Country Status (19)
Country | Link |
---|---|
US (1) | US3846466A (es) |
JP (1) | JPS4941529A (es) |
AR (1) | AR204508A1 (es) |
AU (1) | AU469589B2 (es) |
BE (1) | BE800053A (es) |
BR (1) | BR7303867D0 (es) |
CA (1) | CA1010052A (es) |
CH (1) | CH574209A5 (es) |
CS (1) | CS178426B2 (es) |
DD (1) | DD104695A5 (es) |
DE (1) | DE2324020A1 (es) |
FR (1) | FR2189386B1 (es) |
GB (1) | GB1385602A (es) |
GT (1) | GT197328916A (es) |
IL (1) | IL42356A0 (es) |
IT (1) | IT985198B (es) |
NL (1) | NL7307336A (es) |
RO (1) | RO71925A (es) |
ZA (1) | ZA733452B (es) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3960917A (en) * | 1975-05-05 | 1976-06-01 | Stauffer Chemical Company | Bis-cycloalkylthiocarbamates |
US4056627A (en) * | 1975-05-05 | 1977-11-01 | Stauffer Chemical Company | Bis-cycloalkylthiocarbamates as insect control agents |
US4165310A (en) * | 1978-07-31 | 1979-08-21 | Monsanto Company | Scorch inhibited vulcanizable rubber compositions containing carbamic acid esters |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008034787A2 (en) | 2006-09-18 | 2008-03-27 | Basf Se | Pesticidal mixtures comprising an anthranilamide insecticide and a fungicide |
EP2164323A1 (en) | 2006-12-15 | 2010-03-24 | Rohm and Haas Company | Mixtures comprising 1-methylcyclopropene |
WO2008095913A2 (en) | 2007-02-06 | 2008-08-14 | Basf Se | Pesticidal mixtures |
JP2010524483A (ja) | 2007-04-23 | 2010-07-22 | ビーエーエスエフ ソシエタス・ヨーロピア | 化学物質とトランスジェニック改変とを組み合わせることによる植物生産性の増強 |
PL2205082T3 (pl) | 2007-09-26 | 2012-08-31 | Basf Se | Trójskładnikowe kompozycje grzybobójcze zawierające boskalid i chlorotalonil |
WO2011026796A1 (en) | 2009-09-01 | 2011-03-10 | Basf Se | Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi |
KR20130132942A (ko) | 2010-12-20 | 2013-12-05 | 바스프 에스이 | 피라졸 화합물을 포함하는 살충 활성 혼합물 |
EP2481284A3 (en) | 2011-01-27 | 2012-10-17 | Basf Se | Pesticidal mixtures |
EP2688405B1 (en) | 2011-03-23 | 2017-11-22 | Basf Se | Compositions containing polymeric, ionic compounds comprising imidazolium groups |
CN103987261A (zh) | 2011-09-02 | 2014-08-13 | 巴斯夫欧洲公司 | 包含芳基喹唑啉酮化合物的农业混合物 |
BR122019015138B1 (pt) | 2012-06-20 | 2020-04-07 | Basf Se | mistura pesticida, composição, composição agrícola, métodos para o combate ou controle das pragas de invertebrados, para a proteção dos vegetais em crescimento ou dos materias de propagação vegetal, para a proteção de material de propagação vegetal, uso de uma mistura pesticida e métodos para o combate dos fungos fitopatogênicos nocivos e para proteger vegetais de fungos fitopatogênicos nocivos |
US20150257383A1 (en) | 2012-10-12 | 2015-09-17 | Basf Se | Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material |
US10759767B2 (en) | 2012-12-20 | 2020-09-01 | BASF Agro B.V. | Compositions comprising a triazole compound |
EP2783569A1 (en) | 2013-03-28 | 2014-10-01 | Basf Se | Compositions comprising a triazole compound |
EP2835052A1 (en) | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
EP3046915A1 (en) | 2013-09-16 | 2016-07-27 | Basf Se | Fungicidal pyrimidine compounds |
EP2979549A1 (en) | 2014-07-31 | 2016-02-03 | Basf Se | Method for improving the health of a plant |
RU2707051C2 (ru) | 2014-10-24 | 2019-11-21 | Басф Се | Неамфолитные, кватернизируемые и водорастворимые полимеры для модифицирования поверхностного заряда твердых частиц |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB599179A (en) * | 1945-10-03 | 1948-03-05 | John Woolley Batty | Thiolcarbamic esters |
US3056822A (en) * | 1958-09-22 | 1962-10-02 | Monsanto Chemicals | Bis(haloalkenyl)polymethylenebis-(dithiocarbamates) |
GB917869A (en) * | 1959-10-20 | 1963-02-06 | Ici Ltd | Improvements in and relating to production of urethanes |
GB918892A (en) * | 1960-01-29 | 1963-02-20 | Olin Mathieson | Method of manufacturing heat exchangers |
DE1161255B (de) * | 1962-05-07 | 1964-01-16 | Bayer Ag | Verbessertes Verfahren zur Herstellung von N-substituierten Thiocarbaminsaeure-S-estern |
US3344163A (en) * | 1962-11-24 | 1967-09-26 | Bayer Ag | Bis-dithiocarbamic acid ester derivatives |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE631961A (es) * | ||||
US3226428A (en) * | 1962-07-19 | 1965-12-28 | Sidney L Vail | Biscarbamate-formaldehyde adducts |
-
1972
- 1972-05-26 US US00257092A patent/US3846466A/en not_active Expired - Lifetime
-
1973
- 1973-01-01 AR AR248182A patent/AR204508A1/es active
- 1973-05-03 GB GB2097473A patent/GB1385602A/en not_active Expired
- 1973-05-12 DE DE2324020A patent/DE2324020A1/de active Pending
- 1973-05-22 CA CA171,963A patent/CA1010052A/en not_active Expired
- 1973-05-22 ZA ZA733452A patent/ZA733452B/xx unknown
- 1973-05-22 JP JP48056430A patent/JPS4941529A/ja active Pending
- 1973-05-22 CS CS3675A patent/CS178426B2/cs unknown
- 1973-05-23 CH CH736573A patent/CH574209A5/xx not_active IP Right Cessation
- 1973-05-23 AU AU56042/73A patent/AU469589B2/en not_active Expired
- 1973-05-24 GT GT197328916A patent/GT197328916A/es unknown
- 1973-05-24 IT IT50192/73A patent/IT985198B/it active
- 1973-05-24 FR FR7318977A patent/FR2189386B1/fr not_active Expired
- 1973-05-25 IL IL42356A patent/IL42356A0/xx unknown
- 1973-05-25 BR BR3867/73A patent/BR7303867D0/pt unknown
- 1973-05-25 DD DD171091A patent/DD104695A5/xx unknown
- 1973-05-25 BE BE131536A patent/BE800053A/xx unknown
- 1973-05-25 NL NL7307336A patent/NL7307336A/xx unknown
- 1973-05-26 RO RO7374927A patent/RO71925A/ro unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB599179A (en) * | 1945-10-03 | 1948-03-05 | John Woolley Batty | Thiolcarbamic esters |
US3056822A (en) * | 1958-09-22 | 1962-10-02 | Monsanto Chemicals | Bis(haloalkenyl)polymethylenebis-(dithiocarbamates) |
GB917869A (en) * | 1959-10-20 | 1963-02-06 | Ici Ltd | Improvements in and relating to production of urethanes |
GB918892A (en) * | 1960-01-29 | 1963-02-20 | Olin Mathieson | Method of manufacturing heat exchangers |
DE1161255B (de) * | 1962-05-07 | 1964-01-16 | Bayer Ag | Verbessertes Verfahren zur Herstellung von N-substituierten Thiocarbaminsaeure-S-estern |
US3344163A (en) * | 1962-11-24 | 1967-09-26 | Bayer Ag | Bis-dithiocarbamic acid ester derivatives |
Non-Patent Citations (3)
Title |
---|
Bachmann et al., J. Amer. Chem. Soc. 3,132 3,134. * |
Curry et al., J. Amer. Chem. Soc. 5,043 5,046. * |
Martin et al., pgs. 23 30, Chem. Ber. 102 (1969). * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3960917A (en) * | 1975-05-05 | 1976-06-01 | Stauffer Chemical Company | Bis-cycloalkylthiocarbamates |
US4056627A (en) * | 1975-05-05 | 1977-11-01 | Stauffer Chemical Company | Bis-cycloalkylthiocarbamates as insect control agents |
US4165310A (en) * | 1978-07-31 | 1979-08-21 | Monsanto Company | Scorch inhibited vulcanizable rubber compositions containing carbamic acid esters |
Also Published As
Publication number | Publication date |
---|---|
BR7303867D0 (pt) | 1974-01-08 |
FR2189386B1 (es) | 1977-02-11 |
IT985198B (it) | 1974-11-30 |
ZA733452B (en) | 1974-04-24 |
CS178426B2 (es) | 1977-09-15 |
IL42356A0 (en) | 1973-07-30 |
FR2189386A1 (es) | 1974-01-25 |
AU5604273A (en) | 1974-11-28 |
GB1385602A (en) | 1975-02-26 |
GT197328916A (es) | 1974-11-15 |
AU469589B2 (en) | 1976-02-19 |
NL7307336A (es) | 1973-11-28 |
JPS4941529A (es) | 1974-04-18 |
CA1010052A (en) | 1977-05-10 |
DD104695A5 (es) | 1974-03-20 |
AR204508A1 (es) | 1976-02-12 |
RO71925A (ro) | 1982-05-10 |
CH574209A5 (es) | 1976-04-15 |
BE800053A (fr) | 1973-11-26 |
DE2324020A1 (de) | 1973-12-06 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: ICI AMERICAS INC., A DE CORP., DELAWARE Free format text: CHANGE OF NAME;ASSIGNOR:STAUFFER CHEMICAL COMPANY;REEL/FRAME:005197/0025 Effective date: 19890815 |