US3763143A - 1 - (alkyleneiminocarbonyl)-n-(substituted carbamoyloxy)thioformimidates - Google Patents

1 - (alkyleneiminocarbonyl)-n-(substituted carbamoyloxy)thioformimidates Download PDF

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Publication number
US3763143A
US3763143A US00223001A US3763143DA US3763143A US 3763143 A US3763143 A US 3763143A US 00223001 A US00223001 A US 00223001A US 3763143D A US3763143D A US 3763143DA US 3763143 A US3763143 A US 3763143A
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United States
Prior art keywords
thioformimidate
methyl
thioformimidates
alkyleneiminocarbonyl
piperidinocarbonyl
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Expired - Lifetime
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US00223001A
Inventor
J Buchanan
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EIDP Inc
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EI Du Pont de Nemours and Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
    • C07D203/18—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carboxylic acids, or by sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
    • C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Definitions

  • R is alkyl of 1 through 4 carbon atoms or alkenyl of 3 through 4 carbon atoms
  • R is alkyl of 1 through 3 carbon atoms, allyl or pro- R is hydrogen or methyl
  • R and R are joined and are alkylene of 2 through 6 carbon atoms.
  • Methyl 1- (aziridinocarbonyl) -N- (methylcarbamoyloxy) thioformimidate Methyl 1- (hexahydro azepinocarbonyl) -N- (methylcarbamoyloxy) thioformimidate Methyl 1- pyrrolidinocarbonyl) -N- (methylcarb amoyloxy) thioformimidate Ethyl 1- pip eridinocarb onyl) -N- allylcarbamoyloxy) thioformimidate p CC Ethyl l- (piperidinocarbonyl -N- (butylcarbamoyloxy) thioformimidate Butyl 1- (piperidinocarbonyl) -N- (methylcarb amoyloxy) thioformimidate Butyl 1- (piperidinocarbonyl) -N- (butylcarb amoyloxy) thi
  • R is alkyl of 1 through 4 carbon atoms or alkenyl of 3 through 4 carbon atoms
  • R is alkyl of 1 through 3 carbon atoms, allyl or pro- R is hydrogen or methyl
  • R and R are joined and are alkylene of 2 through 6 carbon atoms.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1-(ALKYLENEIMINOCARBONYL)-N-(SUBSTITUTED CARBAMOYLOXY)THIOFORMIMIDATES SUCH AS METHYL 1-(PYRROLIDINOCARBONYL)-N-(METHYLCARBAMOYLOXY)THIOFORMIMIDATE WHICH ARE USEFUL IN PREVENTING THE DESTRUCTIVE EFFECTS OF PESTS SUCH AS INSECTS, TICKS, MITES AND NEMATODES.

Description

United States Patent Int. (:1. C07d 23/06, 27/04, 29/36 U.S. Cl. 260239 E 9 Claims ABSTRACT OF THE DISCLOSURE 1-(alkyleneiminocarbonyl)-N-(substituted carbamoyloxy)thioformimidates such as methyl l-(pyrrolidinocarbonyl) -N- (methylcarbamoyloxy) thioformimidate which are useful in preventing the destructive effects of pests such as insects, ticks, mites and nematodes.
CROSS-REFERENCE TO RELATED APPLICATIONS This application is a division of application Ser. No. 851,531, filed July 9, 1969", now U.S. Pat. 3,658,870, which is in turn a division of application Ser. No. 728,739, filed May 13, 1968, now U.S. Pat. 3,530,220, which is in turn a continuation-in-part of application Ser. No. 647,- 234, filed June 19, 1967, now abandoned.
SUMMARY OF THE INVENTION This invention is a class of compounds of the formula:
wherein R is alkyl of 1 through 4 carbon atoms or alkenyl of 3 through 4 carbon atoms;
R, is alkyl of 1 through 3 carbon atoms, allyl or pro- R is hydrogen or methyl; and
R and R are joined and are alkylene of 2 through 6 carbon atoms.
The background of this invention, and the manner and process of making and using it, are described in US. Pat. 3,530,220, the disclosure of which is incorporated by reference. Some representative compounds of this invention are listed below:
Methyl 1- (aziridinocarbonyl) -N- (methylcarbamoyloxy) thioformimidate Methyl 1- (hexahydro azepinocarbonyl) -N- (methylcarbamoyloxy) thioformimidate Methyl 1- pyrrolidinocarbonyl) -N- (methylcarb amoyloxy) thioformimidate Ethyl 1- pip eridinocarb onyl) -N- allylcarbamoyloxy) thioformimidate p CC Ethyl l- (piperidinocarbonyl -N- (butylcarbamoyloxy) thioformimidate Butyl 1- (piperidinocarbonyl) -N- (methylcarb amoyloxy) thioformimidate Butyl 1- (piperidinocarbonyl) -N- (butylcarb amoyloxy) thioformimidate Methyl l-piperidinocarbonyl-N-(dimethylcarbamoyloxy) thioformimidate The above named compounds are disclosed in Tables II and III which appear in columns 11 through 14 of U.S. Pat. 3,530,220.
I claim:
1. A compound of the formula:
R is alkyl of 1 through 4 carbon atoms or alkenyl of 3 through 4 carbon atoms;
R, is alkyl of 1 through 3 carbon atoms, allyl or pro- R is hydrogen or methyl; and
R and R are joined and are alkylene of 2 through 6 carbon atoms.
2. The compound of claim 1 which is methyl l-(aziridinocarbonyl) N (methylcarbamoyloxy)thioformimidate.
3. The compound of claim 1 which is methyl l-(hexahydroazepinocarbonyl) N (methylcarbamoyloxy)thioformimidate.
4. The compound of claim 1 which is methyl l-(pyrrolidinocarbonyl) N (methylcarbamoyloxy)thioformimidate.
5. The compound of claim 1 which is ethyl l-(piperidinocarbonyl) N (allylcarbamoyloxy)thioformimidate.
6. The compound of claim 1 which is ethyl l-(piperidinocarbonyl) N (butylcarbamoyloxy)thioformimidate.
7. The compound of claim 1 which is butyl l-(piperidinocarbonyl) N (methylcarbamoyloxy)thioformimidate.
8. The compound of claim 1 which is butyl l-(piperidinocarbonyl) N (butylcarbamoyloxy)thioiormimidate.
9. The compound of claim 1 which is methyl l-piperidinocarbonyl N (dimethylcarbamoyloxy)thioformimidate.
References Cited FOREIGN PATENTS 6615725 5/1967 Netherlands 260453 R ALTON D. ROLLlINS, Primary Examiner U.S. Cl. X.R.
260239 A, 239 BF, 293.85, 326.3
US00223001A 1967-06-19 1972-02-02 1 - (alkyleneiminocarbonyl)-n-(substituted carbamoyloxy)thioformimidates Expired - Lifetime US3763143A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US64723467A 1967-06-19 1967-06-19
US72873968A 1968-05-13 1968-05-13
US85153169A 1969-07-09 1969-07-09
US22300172A 1972-02-02 1972-02-02

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US3763143A true US3763143A (en) 1973-10-02

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4316911A (en) * 1980-11-03 1982-02-23 E. I. Du Pont De Nemours And Company Ureidosulfenyl carbamate nematicides
US20030100604A1 (en) * 2000-03-28 2003-05-29 Reiner Fischer Active substance combinations having insecticidal and acaricidal properties
US6576661B1 (en) 1999-11-09 2003-06-10 Bayer Aktiengesellschaft Active ingredient combination having insecticidal and acaricidal characteristics
US7060692B2 (en) 2000-08-31 2006-06-13 Bayer Cropscience Ag Active ingredient combinations comprising insecticidal and acaricidal properties

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4316911A (en) * 1980-11-03 1982-02-23 E. I. Du Pont De Nemours And Company Ureidosulfenyl carbamate nematicides
US6576661B1 (en) 1999-11-09 2003-06-10 Bayer Aktiengesellschaft Active ingredient combination having insecticidal and acaricidal characteristics
US6818670B2 (en) 1999-11-09 2004-11-16 Bayer Aktiengesellschaft Active ingredient combination having insecticidal and acaricidal characteristics
US20030100604A1 (en) * 2000-03-28 2003-05-29 Reiner Fischer Active substance combinations having insecticidal and acaricidal properties
US6900190B2 (en) 2000-03-28 2005-05-31 Bayer Aktiengesellschaft Active substance combinations having insecticidal and acaricidal properties
US7060692B2 (en) 2000-08-31 2006-06-13 Bayer Cropscience Ag Active ingredient combinations comprising insecticidal and acaricidal properties

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