Insecticidal Ureas and thioureas

• US 4,833,151 A
• Filed: 05/28/1986
• Issued: 05/23/1989
• Est. Priority Date: 05/15/1970
• Status: Expired due to Term

• Current Assignee: Deutsche Bank AG, New York Branch (Deutsche Bank)
• Original Assignee: Duphar International Research B.V. (Abbott Laboratories Incorporated)
• Inventors: Mulder, Rudolf, Wellinga, Kobus
• Primary Examiner(s): Schenkman, Leonard
• Application Number:
  US06/867,695
• Time in Patent Office: 1,091 Days
• Field of Search: 514/344, 514/353, 514/522, 514/584, 514/594, 514/595
• US Class Current: 514/344
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/88 six-membered rings with three ring hetero atoms
• CPC Class Codes: A01N 47/34 containing the groups , e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
• CPC Class Codes: C07C 275/54 Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
• CPC Class Codes: C07D 233/66 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
• CPC Class Codes: C07D 233/72 Two oxygen atoms, e.g. hydantoin
• CPC Class Codes: C07D 273/04 Six-membered rings
• CPC Class Codes: H01L 27/00 Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate details thereof H01L23/00, H01L29/00 - H10K10/00; assemblies consisting of a plurality of individual solid state devices H01L25/00
• CPC Class Codes: Y10S 516/01 Wetting, emulsifying, dispersing, or stabilizing agents

Abstract

Certain organic compounds derived from urea or thio-urea having insectical activity and methods of their preparation are disclosed. The compounds according to the invention have been found to interfere with the mechanism of metamorphoses which occurs in insects. Hence, the substances according to the invention are specifically active against insects. Owing to this specificity and because of the absence of phytotoxicity effects, the compounds of this invention are of prime importance.

Claims

1. An insecticidal composition comprising an inert carrier and an insecticidally effective amount, as active ingredient, of a compound of the formula ##STR38## wherein A is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group;

B also is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, with the proviso that A and B are not both a hydrogen atom;

R is a hydrogen atom, an alkyl group, a hydroxy group, an alkoxy group, an alkoxymethyl group, an acyl group, or an alkoxycarbonyl group;

X and Y each are an oxygen atom or a sulfur atom;

R₁ is a hydrogen atom, an alkyl group that may be substituted with halogen, with alkoxy, with alkylthio, or with cyano, a 1-cycloalkenyl group, a benzyl group that may be substituted with halogen, a hydroxy group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an alkoxythiocarbonyl group, an alkylsulfonyl group, or a phenylsulfonyl group; and

R₂ is a substituted or non-substituted phenyl group or a pyridyl group that may be substituted with halogen, with nitro, with cyano, or with halogenated alkyl;

with the proviso that the active ingredient comprises a compound that is not included in any of the following paragraphs;

(1) A and B are each independently selected from the group consisting of chlorine, fluorine, and methyl, R₁ is selected from the group consisting of hydrogen and lower alkyl, R₂ is a phenyl group substituted with 1-3 substituents selected from the group consisting of halogen, alkyl of 1-15 carbons, halogen derivatives of said alkyl, cycloalkyl, and halogenated cycloalkyl, nitro, and phenyl, X and Y are both oxygen atoms, and R is a hydrogen atom;

(2) N-(2,6-dichlorobenzyl)-N'"'"'-(4-cyanophenyl)urea;

(3) N-(2-monochlorobenzoyl)-N'"'"'-(3,4-dichlorophenyl)urea.

2. The composition of claim 1, wherein:

A is a hydrogen atom, a chlorine atom, a fluorine atom, or a methyl group;

B also is a hydrogen atom, a chlorine atom, a fluorine atom, or a methyl group;

X and Y each are an oxygen atom;

R is a hydrogen atom;

R₁ is a hydrogen atom or a lower alkyl group that may be substituted with lower alkoxy; and

R₂ is a substituted or unsubstituted phenyl group.

3. The composition of claim 2, wherein A is a halogen atom and B is a hydrogen atom.

4. The composition of claim 2, wherein A and B are both halogen atoms.

5. The composition of claim 1, wherein X and Y are the same.

6. The composition of claim 1, wherein the active ingredient comprises a compound that is not a N-(2-monohalobenzoyl)-N'"'"'-3,4-dichlorophenyl)urea.