Back to results
US 8,940,942 B2Granted
Synthetic navel orangeworm pheromone composition and methods relating to production of same
AssigneeSuterra, LLC
InventorsAndrew Thompson, Xiongzhi Zhang, Lonnie Robarge
Life of this patent
Estimating the term…
Abstract
One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.
Claims20
A method for synthesizing a sex attractant pheromone comprising:
- producing a compound of formula Y′—R1—X (2) in step A, wherein step A comprises an oxidation reaction on a compound of formula Y—R1—X (1);
- producing a compound of formula
- (3) in step B, wherein step B comprises an alkylation reaction on (2);
- producing a compound of formula
- (4) in step C, wherein step C comprises an alkylation reaction on (3);
- producing a compound of formula
- (6) in step E, wherein step E comprises reacting (4) with a compound of formula R3—R5—X′ (5b), wherein (5b) is synthesized from a compound of the formula R3—R4 (5a) through a halogenation reaction;
- and
- producing a final compound of formula R3—R7—R1—Y′ (7) in step F, wherein step F comprises a reduction reaction and a hydrolysis reaction on (6),
- wherein:
- X is chlorine,
- X′ is bromine,
- Y is —OH,
- Y′ is ═O,
- R1 is [—CH2—]m,
- R2 is —C≡CH,
- R3 is CH3—[CH2]n—,
- R4 is —C≡CH,
- R5 is [—C≡C—]p,
- R6 is [—C≡C—]q,
- R7 is R8,
- W is —O—CH2—CH3,
- R8 is the geometric cis configuration represented by structure
- m is 10,
- n is 1,
- p is 1, and
- q is 2.
24 more elements
A method for synthesizing a sex attractant pheromone comprising:
- producing a compound of formula Y′—R1—X (2) in step A, wherein step A comprises an oxidation reaction on a compound of formula Y—R1—X (1);
- producing a compound of formula
- (3) in step B, wherein step B comprises an alkylation reaction on (2);
- producing a compound of formula
- (6) in step H, wherein step H comprises reacting (3) with a compound of formula R3—R5—R10-M (8b);
- and
- producing a final compound of formula R3—R7—R1—Y′ (7) in step F, wherein step F comprises a reduction reaction and a hydrolysis reaction on (6),
- wherein:
- X is chlorine,
- Y is —OH,
- Y′ is ═O,
- R1 is [—CH2—]m,
- R3 is CH3—[CH2]n—,
- R5 is [—C≡C—]p,
- R6 is [—C≡C—]q,
- R7 is R8,
- W is —O—CH2—CH3,
- R8 is the geometric cis configuration represented by structure
- R9 is —CH3,
- R10 is ≡C(−),
- M is sodium,
- m is 10,
- n is 1,
- p is 1, and
- q is 2.
22 more elements
A method for synthesizing a sex attractant pheromone comprising:
- producing a compound of formula Y′—R1—X (2) in step A, wherein step A comprises an oxidation reaction on a compound of formula Y—R1—X (1);
- producing a compound of formula
- (3) in step B, wherein step B comprises an alkylation reaction on (2);
- producing a compound of formula
- (6) from a reaction comprising (3);
- and
- producing a final compound of formula R3—R7—R1—Y′ (7) in step F, wherein step F comprises a reduction reaction and a hydrolysis reaction on (6),
- wherein:
- X is chlorine,
- Y is —OH,
- Y′ is ═O,
- R1 is [—CH2—]10,
- R3 is CH3—[CH2]1—,
- R6 is [—C≡C—]2,
- R7 is the geometric cis configuration represented by structure
- and
- W is —O—CH2—CH3.
14 more elements
Dependencies are inferred from the claim text.