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US 2019/0047937 A1Published application
Insect repellent compounds and compositions, and methods thereof
AssigneeIowa State University Research Foundation, Inc.
InventorsJoel R. Coats, Edmund J. Norris, James Scott Klimavicz
Life of this patent
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Abstract
The present invention relates to monoterpenoid and phenylpropanoid containing derivative compounds, methods of making the compounds, compositions comprising the compounds, and methods of repelling pests using the compounds and/or compositions.
Claims48
A compound of formula (A) as follows:
- wherein
- R1 is a monoterpenoid or phenylpropanoid moiety;
- R2 is substituted or unsubstituted and is selected from the group consisting of H, C1-C7 unbranched or branched alkyl, C2-C7 unbranched or branched alkenyl, C3-C7 unbranched or branched alkynyl, C3-C7 unbranched or branched cycloalkyl, aryl, heteroaryl, —(CH2)n-heteroaryl, and C3-C7 unbranched or branched cycloalkenyl;
- and
- n is an integer from 0-3, with the proviso that when R1 is a monoterpenoid moiety R2 is not a tert-butyl group.
2 more elements
A compound of formula (B) as follows:
- wherein
- R5 is a monoterpenoid or phenylpropanoid moiety and
- R6 is substituted or unsubstituted and is selected from the group consisting of C3-C7 unbranched or branched alkyl, C2-C7 unbranched or branched alkenyl, C3-C7 unbranched or branched alkynyl, C3-C7 unbranched or branched cycloalkyl, C3-C7 unbranched or branched cycloalkenyl, C3-C7 unbranched or branched heterocycle, C2-C7 saturated or unsaturated hydroxyalkyl, and —(CR11R12)p—O—(CR11R12)q—OH;
- R11 and R12 are individually selected from H or C1-6 alkyl;
- p is an integer from 1 to 4;
- and
- q is an integer from 1 to 4, with the proviso that the compound is not selected from the group consisting of
4 more elements
A method of making a compound of formula (A) or formula (B),
- (i) said method of making the compound of formula (A) comprising:
- reacting
- (I) R1—OH with R2—COOH;
- (II) R1—OH
- with in the presence of a base;
- or
- (III) R1—OH with
- under conditions effective to form an ester having a structure of formula (A)
- wherein
- R1 is a monoterpenoid or phenylpropanoid moiety;
- R2 is substituted or unsubstituted and is selected from the group consisting of H, C1-C7 unbranched or branched alkyl, C2-C7 unbranched or branched alkenyl, C3-C7 unbranched or branched alkynyl, C3-C7 unbranched or branched cycloalkyl, aryl, heteroaryl, —(CH2)n-heteroaryl, and C3-C7 unbranched or branched cycloalkenyl;
- n is an integer from 0-3;
- and
- X is a halide;
- or
- (ii) said method of making the compound of formula (B) comprising:
- reacting
- (I) R5—COOH with R6—OH;
- (II)
- with R2—OH in the presence of a base;
- or
- (III)
- with R6—OH;
- under conditions effective to form an ester having a structure of Formula (B)
- wherein
- R5 is a monoterpenoid or phenylpropanoid moiety and
- R6 is substituted or unsubstituted and is selected from the group consisting of C3-C7 unbranched or branched alkyl, C2-C7 unbranched or branched alkenyl, C3-C7 unbranched or branched alkynyl, C3-C7 unbranched or branched cycloalkyl, C3-C7 unbranched or branched cycloalkenyl, C3-C7 unbranched or branched heterocycle, C2-C7 saturated or unsaturated hydroxyalkyl, and —(CR11R12)q—OH;
- R11 and R12 are individually selected from H or C1-6 alkyl;
- p is an integer from 1 to 4;
- q is an integer from 1 to 4;
- and
- X is a halide.
29 more elements
A composition comprising:
- a carrier and
- (i) a compound of formula (A) as follows:
- wherein
- R1 is a monoterpenoid or phenylpropanoid moiety;
- R2 is substituted or unsubstituted and is selected from the group consisting of H, C1-C7 unbranched or branched alkyl, C2-C7 unbranched or branched alkenyl, C3-C7 unbranched or branched alkynyl, C3-C7 unbranched or branched cycloalkyl, aryl, heteroaryl, —(CH2)n-heteroaryl, and C3-C7 unbranched or branched cycloalkenyl;
- and
- n is an integer from 0-3, with the proviso that when R1 is a monoterpenoid moiety R2 is not a tert-butyl group;
- or
- (ii) a compound of formula (B) as follows:
- wherein
- R5 is a monoterpenoid or phenylpropanoid moiety and
- R6 is substituted or unsubstituted and is selected from the group consisting of C3-C7 unbranched or branched alkyl, C2-C7 unbranched or branched alkenyl, C3-C7 unbranched or branched alkynyl, C3-C7 unbranched or branched cycloalkyl, C3-C7 unbranched or branched cycloalkenyl, C3-C7 unbranched or branched heterocycle, C2-C7 saturated or unsaturated hydroxyalkyl, and —(CR11R12)p—O—(CR11R12)q—OH;
- R11 and R12 are individually selected from H or C1-6 alkyl;
- p is an integer from 1 to 4;
- and
- q is an integer from 1 to 4, with the proviso that the compound is not selected from the group consisting of
13 more elements
A method of repelling a pest, said method comprising:
- applying to a target area a composition comprising a compound of formula (A) or a compound of formula (B);
- wherein, in the compound of formula (A),
- R1 is a monoterpenoid or phenylpropanoid moiety;
- R2 is substituted or unsubstituted and is selected from the group consisting of H, C1-C7 unbranched or branched alkyl, C2-C7 unbranched or branched alkenyl, C3-C7 unbranched or branched alkynyl, C3-C7 unbranched or branched cycloalkyl, aryl, heteroaryl, —(CH2)n-heteroaryl, and C3-C7 unbranched or branched cycloalkenyl;
- and
- n is an integer from 0-3, with the proviso that when R1 is a monoterpenoid moiety R2 is not a tert-butyl group;
- wherein, in the compound of formula (B),
- R5 is a monoterpenoid or phenylpropanoid moiety;
- R6 is substituted or unsubstituted and is selected from the group consisting of C3-C7 unbranched or branched alkyl, C2-C7 unbranched or branched alkenyl, C3-C7 unbranched or branched alkynyl, C3-C7 unbranched or branched cycloalkyl, C3-C7 unbranched or branched cycloalkenyl, C3-C7 unbranched or branched heterocycle, C2-C7 saturated or unsaturated hydroxyalkyl, and —(CR11R12)p—O—(CR11R12)q—OH;
- R11 and R12 are individually selected from H or C1-6 alkyl;
- p is an integer from 1 to 4;
- and
- q is an integer from 1 to 4;
- and
- wherein said applying is carried out under conditions effective to repel a pest.
12 more elements
Dependencies are inferred from the claim text.