Phytochem Rev (2012) 11:543–566 DOI 10.1007/s11101-013-9273-9

Phytochemical feeding deterrents for stored product insect pests Jan Nawrot • Juraj Harmatha

Received: 10 August 2012 / Accepted: 9 January 2013 / Published online: 20 January 2013 Ó Springer Science+Business Media Dordrecht 2013

Abstract This review summarises information on compounds of plant origin and plant products as feeding inhibitors for stored product insects. More than 200 compounds (mostly sesquiterpenes) and over 160 plant extracts have been tested to date. Indeed, we did not consider substances stimulating olfactory receptors (repellents) or compounds just toxic to insects. The main scope of the review is to enable best choice for the most active, as well as biorationally suitable substances, for evolving further rational experiments in future. Feeding inhibitors may be used along with food or sex attractants in biorational control of the stored food pests. However, each semiochemical should be submitted to a formal registration process before its use in practice. Keywords Insect feeding deterrence  Antifeedant phytochemicals  Isoprenoids  Sesquiterpene lactones  Polyphenols

J. Nawrot Institute of Plant Protection, National Research Institute, ul. W. We˛gorka 20, 60-318 Poznan, Poland J. Harmatha (&) Institute of Organic Chemistry and Biochemistry, v.v.i., Academy of Science of the Czech Republic, 166 10 Prague, Czech Republic e-mail: [email protected]

Introduction The group of insect species associated with postharvest products are commonly called stored product pests. Approximately 1,660 insect species may be found in agricultural products during storage, processing, transportation, and marketing (Hagstrum and Subramanyam 2009). Stored product insects are cosmopolitan pests which have been distributed throughout the world by international trade. In developed countries, these insects can cause losses of up to 9 %. In developing countries the losses can be more than 50 % (Pimentel 1991). Pests develop large populations, consume food commodities, and contaminate the goods with cast skins, faeces, hairs, webbing, dead bodies, and toxins. Additionally, allergic reactions to insect proteins have become very common recently (Wirtz 1991; Arlian 2002). Chemical control of these pests with fumigants or contact insecticides can be a health risk because of the pesticide residues. These chemicals can pose a real danger to humans, but we should remember that even the alternative natural compounds may not be entirely safe. An integrated pest management (IPM) method which incorporates sanitation, trapping, or deterrence of insects using semiochemicals may be a modern, safer solution (Cox 2004; Phillips and Throne 2010). The whole process of insect searching for food is divided into well defined behavioural stages (Miller and Strickler 1984). The final acceptance of food follows some steps (first bite, swallowing and continuous

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feeding). Positive and negative factors, such as olfactory, visual, mechanical, and gustatory stimuli are involved. The positive reaction of the receptors is a base for the initiating swallowing and ingestion, or oviposition. Feeding deterrents have been known for many years to play a more important role in insect food selection than feeding attractants or stimulants. Thus, accepting any product as food is easier in the absence of feeding deterrents, than in the presence of attractants (Jermy 1983). So a simple solution would be to add some additional deterrent components to a product, which would then protect the product against insects. Grain or seed, unlike leaf or root plant tissue, does not possess any defensive secondary compounds against insects. Chemical composition of grain and food quality is usually stable for insects during the whole storage period. However, some volatile compounds associated with grain are produced by micro flora (fungi, bacteria) occurring on the grain surface (Kamin´ski et al. 1974). Feeny (1976) published a catalogue of all compounds corresponding with plant–insect communication. Antifeedants, known as allomones, are defined as substances produced by an organism, which provide adaptive advantage for the organism. In simple terms, an antifeedant or feeding deterrent or feeding inhibitor is a compound (of natural or synthetic origin) that reduces food intake by an insect. Isman (1994) gave the most precise definition: ‘‘A peripherally mediated behavior–modifying substance (i.e., acting directly on the chemosensilla in general and deterrent receptors in particular) resulting in feeding deterrence’’. According to this definition, any compound that affects the central nervous system following ingestion or which affects the central nervous system through the olfactory receptors should be excluded from this review. We have taken into consideration the methods of testing, and we did not insert volatile compounds because in the literature already exist many good reviews on repellent or fumigant action of phytochemicals (mainly essential oils) against stored product insects (Bakkali et al. 2008; Rajendran and Sriranjini 2008; Ukeh and Mordue (Luntz) 2009; Nerio et al. 2010, Regnault-Roger et al. 2012). Recently, an improved method for testing the feeding deterrent activity of volatile compounds against stored product insects was published (Stefanazzi et al. 2011). A model of behavioral reaction of stored grain beetles differs from a feeding model on green plant specialists,

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because grain insects can uninhibitedly infest new parts of grain mass, so often they do not need to search long distances for food. Each natural or synthetic compound selected for experiments on deterrent action against stored product insects should fulfill several necessary requirements and possess some special properties (van Beck and de Groot 1986; Ascher 1992), such as: 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11.

being non-toxic to people, animal and beneficial insects not changing the taste, smell or other aspects of the protected product inhibiting feeding of a wide range of stored product insect species being toxic to pests to be controlled being efficient at very low doses being active for a long period (relative to products storage period) not leaving any residues or metabolites being easy to apply/use having low production costs being compatible with the use with other insecticides in IPM being a stable chemical

Taking into accounts antifeedant chemical properties and the duration of their activity, they may be categorized into two groups: (1) absolute (long-lasting feeding deterrence and ultimately starvation), and (2) relative (showing feeding deterrence over defined time) (Koul 1982). Compounds from the first group act by suppressing the activity of neurons in general. Compounds from the second group are perceived by specialized receptors which lead to a change in insect behavior (Chapman 1974). Each insect species has its own specific peripheral nervous system (different type of receptors adapted to the texture of a food surface) and also a specific central nervous system which integrates receptor signals. Therefore, it is possible to predict that each insect species may react to each compound occurring in food in a different manner. A compound acting as deterrent for one species may be a neutral or stimulant factor for another one. For example, azadirachtin, a triterpene isolated from Azadirachta indica, is a very active antifeedant against 90 % of the more than 600 tested herbivorous and stored product insect species (Morgan 2009). However, in the case of some important species (Epilachna varivestis, Spodoptera littoralis

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and Oryzaephilus surinamensis), the antifeedant activity of this compound is weak or ineffective (Ascher 1992; Mordue and Blackwell 1993). The problem of antifeedants and antifeeding activity being specific to herbivore insect species was reported broadly in many reviews by Chapman (1974), Koul (1982, 2005, 2008), Schoonhoven (1982), Norris (1986), Isman (2002, 2006). However, there is only little information on antifeedants as concerns stored product insects (Nawrot and Harmatha 1994).

Methods of testing In the designing of bioassay tests, all critical parameters, especially the following, should be considered: the substrate used for chemicals, lighting, temperature and relative humidity in a test room, number of insects, their age or larval instar, dose of chemical/extract and duration of test. A large number of substances are suitable for antifeedant carriers in these bioassays. The most commonly used are: starch, cellulose or flour cake, elderberry pith, whole grain or seeds. A general rule for the identification of antifeedant activity is to compare the difference between the consumed amount of treated and untreated food eaten by insects. Experiments can be carried out using choice and nochoice tests. Conclusions drawn from choice tests are usually improved by comparing the results to those from no-choice tests. In tests where the quantity of eaten food is being determined, the number of insects used is very important. Since individual stored product pests ingest only a small amount of food, too small a number of individuals in the bioassay will only give positive results over an extended time period. In such cases, the stability of a compound may change (decrease). On the other hand, overcrowding of the pest population may result in the food being crushed by insect movement and food loss due to insect feeding could not be measured. In our opinion, wheat flour wafer is the best material to be used as the antifeedant carrier (Nawrot et al. 1986a). Many authors have modified this method and for testing, they used pure compounds and plant extracts (AlonsoAmelot et al. 1994; Talukder and Howse 1995; Xie et al. 1996; Huang and Ho 1998; Chiam et al. 1999; Liu et al. 2002; Tripathi et al. 2003a, b; Omar et al. 2007). Wheat, maize or rice grain treated with plant extracts prepared with different solvents (water,

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hexane, chloroform, ethanol) were also often used (Roychoudhury 1993); Schmidt and Streloke 1994; Owusu 2001). Product treatments using seed, root or leaf powder were less popular (Niber 1994; Roychoudhury 1993 ; Kestenholz et al. 2007). Insects developing on fabrics were tested using woollen cloth (Gerard et al. 1992; Han et al. 2006). To date, terms for effective doses of antifeedants have not been standardized. Most authors use their own units of compound/extract concentration. We used: mg/kg of food (ppm), lmol/kg of food or lmol/ cm2 of wafer discs. Active doses were calculated for a 50 % or 95 % reduction of food intake or extent of food intake (Ascher 1979). A wafer disc method adapted to stored product insects was suggested by Harmatha and Nawrot (1984). This method is based on the calculation of three coefficients: relative (from choice tests), absolute (from no-choice tests) and total (the sum of two previous values). Classification of the total coefficients enables a precise evaluation of compound activity. The different composition of active substances in plants collected under different climatic conditions makes consistent screening of antifeedant activity with plant extracts particularly difficult. It is worth mentioning, that the presence of antifeedants in food may also cause some changes in insect behaviour. Observed changes include increases in the mobility of an individual over several food intake trials. The activity of chemical compounds may also be evaluated using the electroantennogram (EAG) technique (Shang et al. 1993), electronic sensors (Jones 1979) or a video camera (camcorder) connected to a PC (Bowdan 1984). The most recent method is the in vitro detection of ligands between dendritic membrane lipoproteins and biologically active chemicals (Spector and Glendinning 2009). There are no reports of such modern methods used in experiments with stored product insects.

Occurrence of natural antifeedants More than 240 pure compounds of plant (148), fungi (53) or commercial (39) origin were tested against 17 insect species (Table 1). The majority of them belong to the group of terpenoids and particularly to sesquiterpene lactones (77). Sesquiterpene lactones are characteristic for the family Compositae (Asteraceae)

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but also occur sporadically in other plant families and in some liverworts and fungi. They are bitter in taste and are known as anti-tumor, cytotoxic, anti-microbial, phytotoxic, human-allergic, and insect feeding deterrent agents (Picman 1986). Furthermore, 15 triterpenes, 11 lignans, 11 alkaloids, 10 saponins, and 5 monoterpens were checked as feeding deterrents. The variety of chemical structures responsible for feeding deterrent activity is very extensive. Nearly all types of low molecular substances have been identified among antifeedants. The most abundant types are simple aliphatic substances: terpenoids, steroids, alkaloids, simple and complex phenolic substances, quinones, phenylpropanoids and their relatives, e.g. lignans, coumarins, flavonoids, rotenoids, and several unique types of compounds. They sometimes are simple hydrocarbons, but more frequently they are oxidized forms, such as alcohols, aldehydes, ketones, carboxylic acids, lactones or epoxides with one or more hydroxyl-, oxo- or oxygroups and also with one or more isolated or conjugated double bonds. In some cases, the functional groups are conjugated with aliphatic acids, carbohydrates or alcohols to form corresponding derivatives, i.e. esters, glycosides or acetals. The insect species used for antifeeding tests are displayed in Table 1. A tabular list of natural compounds tested as feeding deterrents against stored product insects is surveyed in the Table 2. The Table 3 summarizes various plant products and extracts which were tested as antifeedants against stored product insects, too. It shows a list of 162 plant products (powders or extracts) tested as feeding deterrents. The authors identified the most frequently tested indigenous plants (see Table 3), which are mainly medicinal plants or those traditionally used against insect pests.

Structure–activity relationship Antifeedant activity strongly depends on the number and position of the functional groups in the molecule, and often also on the configuration at chiral centers present in the molecules. Very interestingly, there is no direct relationship between chemical reactivity and feeding deterrent activity (Nawrot and Harmatha 1994). This problem was discussed in many publications dealing with antifeedant experiments, as well as in several general or detailed reviews (Koul 1982,

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Phytochem Rev (2012) 11:543–566 Table 1 Insect species tested Species

Family

Order

Attagenus unicolor japonicus Reiter (A.u.j.)

Dermestidae

Coleoptera

Trogoderma granarium Ev. (T.g) Carpophilus hemipterus L. (C.h.)

Nitidulidae

Callosobruchus maculatus F. (C.m.)

Bruchidae

Callosobruchus chinensis L. (C.ch.) Zabrotes subfasciatus Boheman (Z.s.) Lasioderma serricorne F. (L.s.)

Anobiidae

Prostephanus truncatus Horn. (P.t.)

Bostrychidae

Rhyzopertha dominica F. (R.d.) Sitophilus granarius (L.) (S.g.)

Curculionidae

S. oryzae L. (S.o.) S. zeamais (Motsch.) (S.z.) Tenebrio molitor (L.) (T.m.)

Tenebrionidae

Tribolium anafe Hinton (T.a.) T. castaneum Herbst (T.ca.) T. confusum Duv. (T.co) Tineola biseliella Hummel (T.bis.)

Tineidae

Lepidoptera

2008; Schoonhoven 1982; Norris 1986). However, there is still a lack of basic information concerning the exact mode of action and even less information available for explaining the chemical mechanism of activity. A great variety of structures and functional groups are involved in the structure–activity relationship study, but often with a low specificity of feeding deterrence for particular insect species. For these reasons, it is obvious, that there are several different interactions with various molecular receptors in the sensory system of insects, which may differ depending on insect species, on kind of food eaten, and on physiological condition. A wide variety of structures are known to be responsible for antifeedant activity with markedly varied explanations of their chemical mechanism. Moreover, the species specific food search and intake limit any possibility of transfer or extrapolation of

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Table 2 Natural compounds from plants tested as feeding deterrents against stored product insects Compound

Plant source

Insect species

Reference

1. Acetopiperone (phenolic compound)

Commercial

T.co., T.g., S.g.

Harmatha and Nawrot (2002)

2. Acroptilin (sesquiterpene lactone)

Centaurea bella Trautv.

T.co., T.g., S.g.

Nawrot et al. (1986a)

3. Aesculetin (coumarin)

Commercial

T.co., S.g., T.g.

Harmatha et al. (1991)

4. Ageratriol (sesquiterpene lactone)

Achillea ageratum L.

T.co., T.g., S.g.

Nawrot et al. (1986a)

5. Aguerin B (sesquiterpene lactone)

Rhaponticum pulchrum Fisch.et Mey.

T.co.Tg., Sg.

Cis et al. (2006)

6. Alatolide (sesquiterpene lactone)

Jurinea alata (Deaf)

T.co., T.g., S.g.

Nawrot et al. (1982)

7. Acetylisomontanolide (sesquiterpene lactone)

Laserpitium siler (L.)

T.co., T.g., S.g.

Nawrot et al. (1986a)

8. Alantolactone (sesquiterpene lactone)

Parthenium hysterophorus L.

T.ca.

Stipanovic (1983)

9. Alantolactone (sesquiterpene lactone)

Lophocolea heterophylla (Schrad.) Dum

T.co., T.g., S.g.

Nawrot et al. (1986a)

10. Alantolactone (sesquiterpene lactone)

Commercial

T.ca.

Picman et al. (1978)

11. Allyl disulfide (organosulfur compound)

Allium sativum L.

T.ca., S.z.

Chiam et al. (1999)

12. 2b-angelolyleremophilanoide (sesquiterpene lactone)

Petasites hybridus (L.)

T.co., T.g., S.g.

Nawrot et al. (1984a, b)

13. 2-angelolybakkenolide A (sesquiterpene lactone)

Homogyne alpina (L.) Cass.

T.co., T.g., S.g.

Harmatha et al. (1991)

14. Archangelolide (sesquiterpene lactone)

Laserpitium archangelica Wulf.

T.co., T.g., S.g.

Harmatha and Nawrot (1984)

15. Arctolide (sesquiterpene lactone)

Arctotis grandis Thunb

T.co., T.g., S.g.

Nawrot et al. (1986a)

16. Artecanin (sesquiterpene lactone)

Chrysanthemum macrophyllum W.K.

T.co., T.g., S.g.

Nawrot et al. (1982)

17. a-asarone (phenylpropanoid)

Acorus calamus (L.)

T.co., T.g., S.g.

Popławski et al. (2000)

18. b-asarone (phenylpropanoid) 19. b-asarone (phenylpropanoid)

Acorus calamus (L.) Acorus calamus (L.)

T.co., T.g., S.g Pr.tr.

Popławski et al. (2000) Schmidt and Streloke (1994)

20. Azadirachtin (triterpene)

Azadirachta indica A.Juss.

S.g., T.ca.

Jacobson et al. (1984)

21. Azadirachtin (triterpene)

Azadirachta indica A.Juss.

T.co., S.g., T.g.

Harmatha and Nawrot (1988, 2002)

22. Baccatin 2 derivatives (diterpenes) see Fig. 1

Taxus baccata L.

T.co., S.g., T.g.

Daniewski et al. (1998)

23. Bakkenolide A (sesquiterpene lactone), see Fig. 1

Homogyne alpina (L.) Cass.

T.co., S.g., T.g.

Nawrot et al. (1984a, b)

24. Bisaboloangelone (sesquiterpene lactone)

Angelica sylvestris L.

T.co., S.g., T.g.

Nawrot et al. (1984a, b)

25. Bergapten (furocoumarin)

Commercial

T.co., S.g., T.g.

Harmatha et al. (1991)

26. Betuligenol (phenyl alkane)

Taxus baccata L.

T.co., S.g., T.g.

Daniewski et al. (1998)

27. Canin (sesquiterpene lactone)

Chrysanthemum macrophullum W.K.

T.co., T.g., S.g.

Nawrot et al. (1982)

28. Carthamoside (lignan), see Fig. 1 29. l-carvone (monoterpene)

Leuzea carthamoides D.C.

T.co., T.g., S.g

Harmatha and Nawrot (2002)

Synthetic

S.o., T.ca., R.d.,

Tripathi et al. (2003a)

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Table 2 continued Compound

Plant source

Insect species

Reference

30. a-chaconine (alkaloid)

Solanum tuberosum L. Aconitum episcopale Le´veille´

T.g.

Gomah (2011)

31. Chasmanine (alkaloid)

T.ca.

Liu et al. (2011)

32. Chlorojanerin (sesquiterpene lactone)

Rhaponticum pulchrum Fisch.et Mey

T.co., T.g., S.g.

Cis et al. (2006)

33. 1,8-cineole (monoterpene)

Arthermisia annua L.

T.ca.

Tripathi et al. (2001)

34. Cinnamaldehyde (phenylpropanoid)

Cinnamonum aromaticum Nees

T.ca., S.z.

Huang and Ho (1998)

35. Clerodane 14 derivatives (diterpenes) 36. Corollin (glucose nitropropionate), see Fig. 1

Baccharis sagitalis (Less.) DC.

T.m.

Cifuente et al. (2002)

Coronilla varia L.

T.co., T.g., S.g.

Harmatha et al. (1992)

37. Coronillin (glucose nitropropionate), see Fig. 1

Coronilla varia L.

T.co., T.g., S.g.

Harmatha et al. (1992)

38. Coronarian (glucose nitropropionate) 39. Coronopilin (sesquiterpene lactone)

Coronilla varia L.

T.co., T.g., S.g.

Harmatha et al. (1992)

Iva xanthifolia Nutt.

T.co., T.g., S.g.

Nawrot et al. (1982)

Angelica sylvestris L. Aconitum episcopale Le´veille´

T.co., S.g., T.g.

Nawrot et al. (1986a)

T.ca.

Liu et al. (2011)

40. Coumarin (benzopyrone) 41. Crassicauline A (alkaloid) 42. Cubebin (lignan), see Fig. 1

Piper cubeba L.

T.co., S.g., T.g.

Harmatha et al. (1991)

43. Cucurbitacin B (steroid)

Citrullus colocynthis Schrad

T.m.

Tallamy et al. (1997)

44. Cynaropikrin (sesquiterpene lactone)

Rhaponticum pulchrum Fisch.et Mey

T.co., T.g., S.g.

Cis et al. (2006)

45. Daphnoretin (coumarin) 46. Daucosterol (triterpene)

Coronilla varia L. Junellia aspera (Gillies ex Hook)

T.co.T.g., S.g. S.o.

Harmatha et al. (1991, 1992) Pungitore et al. (2005)

47. Deoxy-cubebin (lignan)

Derivative of cubebin

T.co., S.g., T.g.

Harmatha and Nawrot (2002)

48. Deacyladenostylone (sesquiterpene lactone)

Adenostyles alliariae (Gouan) Kern

T.co., S.g., T.g

Nawrot et al. (1984a, b)

49. 8-deoxylactucin (sesquiterpene lactone)

Picris echioides L.

T.co., S.g., T.g

Daniewski et al. (1989)

50. 14-deoxylactucin (sesquiterpene lactone)

Reichardia tingitana L. Roth.

T.co., S.g., T.g

Daniewski et al. (1988)

51. 9-deoxymuzigadial (terpenoid)

Synthetic

T.bis.

Gerard et al. (1992)

52. 12-deoxyphorbol (diterpene)

Euphorbia fischeriana Steud.

T.ca., S.z.

Geng et al. (2011)

53. Deoxyvasicine (alkaloid)

Adhatoda vasica (Ness.)

T.ca.

Saxena et al. (1986)

54. Deoxyvasicinone (alkaloid)

Adhatoda vasica (Ness.)

T.ca.

Saxena et al. (1986)

55. Desacetyl matricarin (sesquiterpene lactone)

Reichardia tingitana L. Roth.

T.co., S.g., T.g

Daniewski et al. (1988)

56. Desacetylo arctolide (sesquiterpene lactone)

Laserpitium siler L.

T.co., S.g., T.g

Nawrot et al. (1985)

57. Dictamnine (limonoid lactone)

Dictamnus dasycarpus Turcz.

T.ca., S.z.

Liu et al. (2002)

58. Dihydroxy-cubebin (lignan)

Derivative of cubebin

T.co., S.g., T.g

Harmatha and Nawrot (2002)

59. Ent-isoalantolactone (sesquiterpene lactone)

Lophocolea heterophylla (Schrad.) Dum.

T.co., T.g., S.g.

Nawrot et al. (1986a)

60. Eucannabinolide (sesquiterpene lactone)

Eupatorium cannabinum L.

T.co., T.g., S.g.

Harmatha et al. (1991)

61. 8-deacyl-eucannabinolide (sesquiterpene lactone)

Eupatorium cannabinum L.

T.co., T.g., S.g.

Harmatha et al.. (1991)

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Table 2 continued Compound

Plant source

Insect species

Reference

62. Eugenol (monoterpene)

Commercial

T.ca.

Alonso-Amelot et al. (1994)

63. 3-hydroxy-grandiolide (sesquiterpene lactone)

Arctotis grandis Thunb.

T.co., T.g., S.g.

Nawrot et al. (1986a)

64. 6 b-hydroxy-eremophilanolide (sesquiterpene lactone)

Petasites albus L.

T.co., S.g., T.g.

Nawrot et al. (1984a, b)

65. Erivanin (sesquiterpene lactone)

Balsamita major Desf.

T.co., T.g., S.g.

Nawrot et al. (1986a)

66. Erysopine (alkaloid)

Erythrina variegata var. orientalis

S.z

Liu et al. (2012)

67. Erysovine (alkaloid) 68. Eulantanaefolide (sesquiterpene lactone)

Erythrina variegata var. orientalis Eupatorium lantanaefolium, Griseb.

S.z. T.co., T.g., S.g.

Liu et al. (2012) Harmatha et al. (1991)

69. Eupatoriopicrin (sesquiterpene lactone)

Eupatorium cannabinum L.

T.co., T.g., S.g.

Nawrot et al. (1982)

70. Eupatolide (sesquiterpene lactone) 71. Eupatolide-NEt2 (sesquiterpene lactone)

Eupatorium cannabinum L.

T.co., T.g., S.g.

Harmatha and Nawrot (1984)

Eupatorium cannabinum L.

T.co., T.g., S.g.

Harmatha and Nawrot (1984)

72. Eupatolide-OMe (sesquiterpene lactone)

Eupatorium cannabinum L.

T.co., T.g., S.g.

Harmatha and Nawrot (1984)

73. Fraxinellone (limonoid lactone) 74. Furandiol (sesquiterpenoid)

Dictamnus dasycarpus Turcz.

T.ca., S.z.

Liu et al. (2002)

Lactarius sp.

T.co., T.g., S.g.

Daniewski et al. (1995)

75. 3-0-ethylfurandiol (sesquiterpenoid)

Lactarius sp.

T.co., T.g., S.g.

Daniewski et al. (1995)

76. 8-epi-furandiol (sesquiterpenoid)

Lactarius sp.

T.co., T.g., S.g.

Daniewski et al. (1995)

77. 8-epi-9-epi-furandiol (sesquiterpenoid)

Lactarius sp.

T.co., T.g., S.g.

Daniewski et al. (1995)

78. Furanol (sesquiterpenoid)

Lactarius sp.

T.co., T.g. S.g.

Daniewski et la. (1995)

79. Furantriol (sesquiterpenoid)

Lactarius sp.

T.co., T.g., S.g

Daniewski et al. (1995)

80. Gedunin (triterpene)

Cedrela odorata L.

S.o.

Omar et al. (2007)

81. Geigerinin (sesquiterpene lactone)

Cephalophora aromatica (Hook.) Schrader

T.co., T.g. Sg.

Błoszyk et al. (1989)

82. Glaucolide A (sesquiterpene lactone)

Vernonia acunnae Alain.

T.co., T.g. Sg.

Harmatha et al. (1991)

83. Glycoalkaloids (alkaloids) 84. Gossypol (polyphenolic aldehyde)

Solanum tuberosum L. Commercial from Gossypium hirsutum L.

T.g. T.co., T.g. Sg.

Gomah (2011) Harmatha et al. (1991)

85. Gradolide (sesquiterpene lactone)

Laserpitium siler L.

T.co., T.g. Sg.

Harmatha and Nawrot (1984)

86. Grossheimin (sesquiterpene lactone) 87. Helenalin (sesquiterpene lactone)

Grossheimia macrocephala Muss.

T.co., T.g., S.g.

Nawrot et al. (1986a)

Helenium aromaticum (Hook.)

T.co., T.g., S.g.

Nawrot et al. (1986a)

88. Hinokinin (lignan)

Derivative of cubebin

T.co., T.g., S.g.

Harmatha and Nawrot (2002)

89. Hirsutolide (sesquiterpene lactone)

Venidium hirsutum Berol.

T.co., T.g., S.g.

Nawrot et al. (1982)

123

550

Phytochem Rev (2012) 11:543–566

Table 2 continued Compound

Plant source

Insect species

Reference

90. Homogynolide A (sesquiterpene lactone), see Fig. 1

Homogyne alpina (L.)

S.g., T.co., T.g.

Nawrot et al. (1986b)

91. Homogynolide B (sesquiterpene lactone)

Homogyne alpina (L.)

S.g., T.co., T.g.

Nawrot et al. (1986b)

92. Humilinolide C (triterpene)

Swietenia humilis Zucc.

S.o.

Omar et al. (2007)

93. Humilinolide B (triterpene)

Swietenia humilis Zucc.

S.o.

Omar et al. (2007)

94. Humilinolide D (triterpene)

Swietenia humilis Zucc.

S.o.

Omar et al. (2007)

95. Hyrcanoside (cardenolide) 96. Degluco-hyrcanoside (cardenolide)

Coronilla varia L. Coronilla varia L.

T.co., S.g., T.g T.co., S.g., T.g

Harmatha et al. (1992) Harmatha et al. (1992)

97. Imperatorin (furocoumarin)

Angelica sylvestris L.

T.co.T.g., S.g.

Harmatha et al. (1991)

98. Isoalantolactone (sesquiterpene lactone)

Inula helenium L.

T.co.T.g., S.g.

Streibl et al. (1983)

99. Isolactaranes, 6 compounds (sesquiterpenes)

Lactarius sp.

S.g., T.co., T.g.

Daniewski et al. (1993)

100. Isolactarorufin (sesquiterpene lactone)

Lactarius rufus (Scop.)

S.g., T.co., T.g

Nawrot et al. (1986a)

101. Isomontanolide (sesquiterpene lactone)

Laserpitium siler L.

T.co., T.g., S.g.

Harmatha and Nawrot (1984)

102. Tetrahydroacetylo-iso montanolide (sesquiterpene lactone)

Laserpitium siler L.

T.co., T.g.S.g.

Nawrot et al. (1986a)

103. Isoonoceratriene (triterpene)

Lansium domesticum Corr.Serr

S.o.

Omar et al. (2007)

104. Isopetasin (sesquiterpene lactone)

Petasites kablikianus Tausch ex Bercht

T.co., T.g., S.g.

Nawrot et al. (1984a, b)

105. Isosilerolide (sesquiterpene lactone)

Laserpitium siler L.

T.co., T.g., Sg.

Nawrot et al. (1986a)

106. Jacquinelin (sesquiterpene lactone)

Picris echioides L.

S.g., T.co., T.g.

Daniewski et al. (1989)

107. Janerin (sesquiterpene lactone)

Rhaponticum pulchrum Fisch. et Mey.

T.co., T.g., S.g.

Cis et al. (2006)

108. Jolkinolide B (diterpenoid)

Euphorbia fischeriana Steud.

T.ca, S.z.

Geng et al. (2011)

109. 17-hydroxyjolkinolide (diterpenoid)

Euphorbia fischeriana Steud.

T.ca, S.z.

Geng et al. (2011)

110. Karakin (glucose nitropropionate)

Coronilla varia L

T.co., T.g., S.g.

Harmatha et al. (1992)

111. Karakoline (alkaloid)

Aconitum episcopale Le´veille´

T.ca.

Liu et al. (2011)

112. Kaurenic acid (diterpene)

Commercial

T.ca.

Alonso-Amelot et al. (1994)

113. Lactaranes, 30 compounds (sesquiterpenes)

Lactarius sp.

S.g., T.co., T.g

Daniewski et al. (1993)

114. LactarolideA (sesquiterpene) 115. 5-deoxy-lactarolide (sesquiterpene)

Lactarius sp. Lactarius sp.

S.g., T.co., T.g S.g., T.co., T.g

Daniewski et al. (1995) Daniewski et al. (1995)

116. Lactarolide B (sesquiterpene)

Lactarius sp.

S.g., T.co., T.g

Daniewski et al. (1995)

117. Lactarorufin A (sesquiterpene lactone), see Fig. 1

Lactarius rufus (Scop.)

S.g.T.co., T.g.

Nawrot et al. (1986a)

118. 8,9-anhydro-lactarorufin A (sesquiterpene lactone)

Derivative of lactarorufin A

S.g.T.co., T.g

Daniewski et al. (1995)

123

Phytochem Rev (2012) 11:543–566

551

Table 2 continued Compound

Plant source

Insect species

Reference

119. 8-epi-lactarorufin A (sesquiterpene lactone)

Derivative of Lactarorufin A

T.o., T.g., S.g.

Daniewski et al. (1995)

120. Lactarorufin A-8-epi-acetate (sesquiterpene lactone)

Derivative of Lactarorufin A

T.o., T.g., S.g.

Daniewski et al. (1995)

121. Lactarorufin A-8-stearate (sesquiterpene lactone)

Derivative of Lactarorufin A

T.o., T.g., S.g.

Daniewski et al. (1995)

122. Lactarorufin B (sesquiterpene lactone)

Lactarius rufus (Scop.)

S.g., T.co., T.g

Daniewski et al. (1995)

123. Lactarorufin D (sesquiterpene lactone)

Lactarius rufus (Scop.)

S.g., T.co., T.g

Daniewski et al. (1995)

124. Lactarorufin E (sesquiterpene lactone)

Lactarius rufus (Scop.)

S.g., T.co., T.g

Daniewski et al. (1995)

125. Lansiolic acid (triterpene)

Lansium domesticum Corr.Serr

S.o.

Omar et al. (2007)

126. Lansiolic acid A (triterpene)

Lansium domesticum Corr.Serr

S.o.

Omar et al. (2007)

127. 3-keto-lansioloc acid (triterpene)

Lansium domesticum Corr.Serr

S.o.

Omar et al. (2007)

128. Laserolide (sesquiterpene lactone)

Laser trilobum (L.) Borkh.

T.co., T.g., S.g.

Nawrot et al. (1986a)

129. Latifolon (phenyl propanoid)

Commercial

T.co., T.g., S.g

Harmatha and Nawrot (2002)

130. Demethyl-latifolon (phenyl propanoid) 131. Linifolin A (sesquiterpene lactone)

Commericial

T.co., T.g., S.g.

Harmatha and Nawrot (2002)

Helenium aromaticum (Hook.)

T.co., T.g., S.g.

Nawrot et al. (1986a)

Synthetic

S.o., R.d., T.ca.

Tripathi et al. (2003b)

132. D-limonene (monoterpene) 133. Lucernic acid (saponin)

Medicago sativa L.

T.m.

Pracros and Corajou (1988)

134. Marasmanes, 7 compounds (sesquiterpenes)

Lactarius sp

S.g., T.co., T.g

Daniewski et al. (1993)

135. Medicagenic acid (saponin)

Medicago sativa L.

T.m.

Pracros and Corajou (1988)

136. Meliternatin (polyoxygenated flavone)

Melicope subunifoliata (Stapf)

S.z.

Ho et al. (2003)

137. Mexicanin I (sesquiterpene lactone)

Helenium aromaticum (Hook.)

T.co., T.g., S.g.

Nawrot et al. (1986b)

138. Neoadenostylone (sesquiterpene lactone)

Adenostyles alliariae (Gouan) Kern

S.g., T.c., T.g.

Nawrot et al. (1984a, b)

139. 3-ntropropionic acid (nitroalkane), see Fig. 1

Coronilla varia L.

S.g., T.co, T.g.

Harmatha et al. (1992)

140. Nobilin (sesquiterpene lactone)

Anthemis nobilis L.

S.g., T.co., T.g.

Harmatha et al. (1991)

141. Onoceradienedione (triterpene)

Lansium domesticum Corr.Serr.

S.o.

Omar et al. (2007)

142. Onoceratriene (triterpene)

Lansium domesticum Corr.Serr.

S.o.

Omar et al. (2007)

143. Onopordopicrin (sesquiterpene lactone)

Onopordon ancanthium L.

T.co., T.g., S.g.

Nawrot et al. (1982)

144. 3-oxo-grandiolide (sesquiterpene lactone)

Arctotis grandis Thunb.

T.co., T.g.S.o.

Nawrot et al. (1986a)

145. Parthenolide (sesquiterpene lactone)

Tanacetum parthenium L.

T.co., T.g., S.g.

Harmatha et al. (1991)

146. Paclitaxel (sesquiterpenoid) 147. Petasolide (sesquiterpenoid)

Taxus baccata L. Petasites hybridus (K)

T.co., T.g., S.g. T.co., T.g., S.g.

Kopczacki et al. (2001) Nawrot et al. (1984a, b)

123

552

Phytochem Rev (2012) 11:543–566

Table 2 continued Compound

Plant source

Insect species

Reference Arnason et al. (1992)

148. Phenolics

Zea mays L

P.t., S.z.

149. a-pinen (monoterpene)

Commercial

T.ca

Alonso-Amelot et al. (1994)

150. b-pinen (monoterpene) 151. Piperonal (phenol deruvative)

Commercial Commercial

T.ca. T.co. T.g., S.g.,

Alonso-Amelot et al. (1994) Harmatha and Nawrot (2002)

152. Piperonylbutoxide (phenypropanoid

Commercial

T.co.T.g., S.g.,

Harmatha and Nawrot (2002)

153. Piperonylideneacetic acid (phenypropanoid)

Commercial

T.co., T.g.S.g.

Harmatha and Nawrot (2002)

154. Podophyllotoxin (lignan)

Synthetic

T.co., T.g., S.g

Harmatha and Nawrot (2002)

155. Polhovolide (sesquiterpene lactone)

Laserpitium siler L.

T.co., T.g., S.g.

Harmatha and Nawrot (1984)

156. Polygodial (terpenoid)

Polygonum hydropiper L.

T.bis.

Gerard et al. (1992)

157. Psolaren (furocoumarin)

Commercial

T.co. T.g., S.g.

Harmatha et al. (1991)

158. Rotenol (isoflavonoid)

Derivative of rotenon

T.co., T.g., S.g.

Nawrot et al. (1989)

159. Rotenone (isoflavonoid)

Derris eliptica (Sweet) Benth.

T.co., T.g., S.g.

Nawrot et al. (1986b)

160. 80 -chlororotenone (isoflavonoid)

Derivative of rotenone

T.co., T.g., S.g.

Nawrot et al. (1989)

161. 80 -12a-chloromethylrotenone (isoflavonoid)

Derivative of rotenone

T.co.T.g., S.g

Nawrot et al. (1989)

162. r80 -formyloxyrotenone (isoflavonoid)

Derivative of rotenone

T.co.T.g., S.g

Nawrot et al. (1989)

163. Sachaconitine (alkaloid)

Aconitum episcopale Le´veille´

T.ca.

Liu et al. (2011)

164. Safrol (phenyl propanoid), see Fig. 1

Commercial

T.co., T.g., S.g.

Harmatha and Nawrot (2002)

165. Salonitenolide (sesquiterpene lactone)

Centaurea salonitana Vis.

T.co., T.g., S.g.

Nawrot et al. (1982)

166. Schkuhriolide (sesquiterpene lactone)

Schkuhria schkuhrioides (Link et Otto)

T.co.T.g., S.g.

Nawrot et al. (1986a)

167. Scopoletin (coumarin)

Coronilla varia L.

T.co.T.g., S.g.

Harmatha et al. (1992)

168. Securacaside A (saponin)

Securidaca longepedunculata Fresen

S.z., C.m.

Stevenson et al. (2009)

168. Securacaside B (saponin)

Securidaca longepedunculata Fresen

S.z., C.m.

Stevenson et al. (2009)

170. Sezamol (phenylpropanoid)

Commercial

T.co.T.g., S.g.

Harmatha and Nawrot (2002)

171. Solamargine (alkaloid)

Solanum khasianum C.B.Clarke

T.ca

Weissenberg et al. (1998)

172. a-solasonine (alkaloid)

Solanum tuberosum L.

T.g

Gomah (2011)

173. Sparteine (alkaloid)

Commercial

T.ca.

Alonso-Amelot et al. (1994)

174. Spirocaracolitone B (triterpene)

Ruptilocarpon caracolito L.

S.o.

Omar et al. (2007)

175. Spirocaracolitone D (triterpene)

Ruptilocarpon caracolito L.

S.o.

Omar et al. (2007)

176. Spirocaracolitone E (triterpene)

Ruptilocarpon caracolito L.

S.o.

Omar et al. (2007)

177. Solasonine (alkaloid)

Solanum khasianum C.B.Clarke

T.ca.

Weissenberg et al. (1998)

178. Stilbeneamorphogenin (phenylpropanoid)

Derivative of rotenon

T.co., T.g., S.g.

Nawrot et al. (1989)

179. Stizolin (sesquiterpene lactone)

Eupatorium lantanaefolium, Griseb.

T.co.T.g., S.g.

Harmatha et al. (1991)

123

Phytochem Rev (2012) 11:543–566

553

Table 2 continued Compound

Plant source

Insect species

Reference

Derivative of stizolin

T.co.T.g., S.g.

Harmatha et al. (1991)

181. Syringin (sesquiterpene lactone)

Rhaponticum pulchrum Fisch. et Mey.

T.co., T.g. S.g.

Cis et al. (2006)

182. Tagalsin A (diterpenoid)

Ceriops tagal (Perr.) C.B. Robinson

T.ca.

Du et al. (2011)

183. Tagalsin B (diterpenoid)

Ceriops tagal (Perr.) C.B. Robinson

T.ca.

Du et al. (2011)

184. Tagalsin H (diterpenoid)

Ceriops tagal (Perr.) C.B. Robinson Aconitum episcopale Le´veille´

T.ca.

Du et al. (2011)

T.ca.

Liu et al. (2011)

180. Stizolin-Net lactone)

2

(sesquiterpene

185. Talatisamine alkaloid) 186. Taxacustin (diterpene)

Taxus baccata L.

T.co., T.g. S.g.

Daniewski et al. (1998)

187. Taxicin 2 derivatives (diterpenes)

Taxus baccata L.

T.co., T.g. S.g.

Daniewski et al. (1998)

188. Taxine A-deaminoacyl (diterpene)

Taxus baccata L.

T.co., T.g. S.g.

Daniewski et al. (1998)

189. Tetrahydroyatein (lignan)

Derivative of yatein

T.co., T.g., S.g.

Harmatha and Nawrot (2002)

190. b-thujaplicin (phenypropanoid)

Commercial

T.co., T.g., S.g.

Harmatha and Nawrot (2002)

191. Tomatine (alkaloid)

Solanum khasianum C.B.Clarke

T.ca.

Weissenberg et al. (1998)

192. Tracheloside (lignan)

Leuzea carthamoides DC

T.co., T.g., S.g

Harmatha and Nawrot (2002)

193. Trilobolide (sesquiterpene lactone), see Fig. 1

Laser trilobum (L.) Borkh.

T.co., T.g., S.g.

Nawrot et al. (1983)

194. Tribromoyatein (lignan)

Derivative of yatein

T.co., T.g., S.g

Harmatha and Nawrot (2002)

195. Umbelliferone (coumarine)

Coronilla varia L.

T.co., T.g., S.g

Harmatha et al. (1992)

196. Ursiniolide (sesquiterpene lactone)

Ursinia anthemoides (L.) Poiret

T.co., T.g., S.g.

Nawrot et al. (1986a)

197. Vachanic acid (sesquiterpene lactone)

Dittrichia viscosa (L.) Greuter

T.ca., R.co.

Daniewski et al. (1986)

198. Vasicine (alkaloid) 199. Vasicinol (alkaloid)

Adhatoda vasica (Ness.) Adhatoda vasica (Ness.)

T.ca. T.ca.

Saxena et al. (1986) Saxena et al. (1986)

200. Vasicinone (alkaloid)

Adhatoda vasica (Ness.)

T.ca.

Saxena et al. (1986)

201. Velleral (sesquiterpene)

Lactarius sp.

T.co., T.g., S.g

Daniewski et al. (1995)

202. Iso-velleral (sesquiterpene), see Fig. 1

Lactarius sp.

T.co. T.g. S.g.

Daniewski et al. (1995)

203. Velutinal (sesquiterpene), see Fig. 1

Lactarius sp.

T.co., T.g., S.g.

Daniewski et al. (1995)

204. Xanthotoxin (furocoumarin)

Commercial

T.co., T.g., S.g.

Harmatha et al. (1991)

205. Xerantholide (sesquiterpene lactone)

Xeranthemum cylindraceum Sibth.et Smith

T.co., T.g., S.g.

Nawrot et al. (1982)

206. Yatein (lignan lactone)

Libocedrus yateensis Guillaumin

T.co., T.g., S.g.

Harmatha and Nawrot (2002)

207. Yateindiol (lignan)

Libocedrus yateensis Guillaumin Aconitum episcopale Le´veille´

T.co., T.g., S.g.

Harmatha et al. (1991)

T.ca.

Liu et al. (2011)

208. Yunaconitine (alkaloid)

A.u.j.—Attagenus unicolor japonicus, C.h.—Carpophilus hemipetrus, C.ch.—Callosobruchus chinensis, C.m.—Calosobruchus maculatus, L.s.—Lasioderma serricorne, P.t.—Prostephanus truncatus, R.d.—Rhyzopertha dominica, S.g.—Sitophilus granarius, S.o.—Sitophilus oryzae, S.z.-Sitophilus zeamais, T.a.—Tribolium anafe, T.bis.—Tineola biseliella, T.ca.—Tribolium castaneum. T.co.—Tribolium confusum, T.g.—Trogoderma granarium, T.m.—Tenebrio molitor, Z.s.—Zabrotes subfasciatus

123

554

Phytochem Rev (2012) 11:543–566

Table 3 Plant products and extracts tested as antifeedants against stored product insects Plant species

Solvent/product

Insect species

Reference

1. Acorus calamus L.

Turmeric oil

R.d.

Jilani and Saxena (1990)

2. Acorus calamus L.

Rhizome powder

P.t.

Schmidt and Streloke (1994)

3. A.calamus var.angustatus Besser 4. Acorus gramineus Solander

Methanol extract Methanol extract

A.u.j A.u.j.

Han et al. (2006) Han et al. (2006)

5. Agastache rugosa (Fischer et Meyer) O.Kuntze

Methanol extract

Au.j.

Han et al. (2006)

6. Allium sativum L.

Methanol extract

A.u.j.

Han et al. (2006)

7. Allium sativum L.

Bulb powder

T.g.

Jood et al. (1993)

8. Alpinia conchigera Griff.

Essential oil

S.z., T.ca.

Suthisut et al. (2011)

9. Alpinia galanga (L.) Wildenow

Methanol extract

T.ca., S.z.

Liu et al. (2007)

10. Angelica dahurica Betham et Hooker

Methanol extract

A.uj.

Han et al. (2006)

11. Aphanamixis polystachya Wall and Parker

Petroleum ether extract

T.ca

Talukder and Howse (1995)

12. Aquilaria agallocha Roxburgh

Methanol extract

A.u.j.

Han et al. (2006)

13. Arthemisia absinthium L.

Water extract

S.g.

14. Arthemisia absinthium L.

Powdered leaves

R.d.

Ignatowicz and Wesolowska (1994) Kłys´ (2004)

15. Arthemisia argyi Leveille et Vaniot

Hexane extract

T.ca., S.z.

Liu et al. (2007)

16. Arthemisia argyi Leveille et Vaniot

Methanol extract

T.ca., S.z.

Liu et al. (2007)

17. Arthemisia princeps var. orientalis (Pampanini) Hara

Methanol extract

A.u.j.

Han et al. (2006)

18. Arthemisia tridentata Nutt.

Leaf powder

Z.s., S.o.

Weaver et al. (1995)

19. Azadirachta indica A.Juss.

Hexane ? isopropyl alkohol extract

T.ca., S.o.

Owusu (2001)

20. Azadirachta indica A.Juss

Powder

P.t., S.o.

Niber (1994)

21. Azadirachta indica A.Juss

Powder

T.g.

Jood et al. (1993)

22. Azadirachta indica A.Juss

Oil

T.g

Jood et al. (1993)

23. Azadirachta indica A.Juss

Oil

R.d.

Jilani and Saxena (1990)

24. Balsamorhiza sagittata Pursh (Nutt.)

Leaf powder

Z.s.S.o.

Weaver et al. (1995)

25. Brucea javanica (L.) Merrill

Methanol extract

T.ca., S.z.

Liu et al. (2007)

26. Capsicum annuum L.

Methanol extract

A.u.j.

Han et al. (2006)

27. Cassia sophera L.

Leaf powder

S.o., C.m.

Kestenholz et al. (2007)

28. Cassia sophera L.

Hot-water extract

S.o.C.m.

Kestenholz et al. (2007)

29. Centaurea alba L.

Methanol extract

T.co.

Kiełczewski et al. (1979)

30. C. banatica Hayek

Methanol extract

T.co.

Kiełczewski et al. (1979)

31. C. calestropa L.

Methanol extract

T.co.

Kiełczewski et al. (1979)

32. C. carniolica Host.

Methanol extract

T.co.

Kiełczewski et al. (1979)

33. C. carpatica Formanel 34. C. ceratophylla Ten

Methanol extract Methanol extract

T.co. T.co.

Kiełczewski et al. (1979) Kiełczewski et al. (1979)

35. C. dichroantha A. Kern.

Methanol extract

T.co.

Kiełczewski et al. (1979)

36. C. maelithensis L.

Methanol extract

T.co.

Kiełczewski et al. (1979)

37. C. micranthos S.G.Gmel.

Methanol extract

T.co.

Kiełczewski et al. (1979)

38. C. nemoralis Jord.

Methanol extract

T.co.

Kiełczewski et al. (1979)

39. C. nicaensis All.

Methanol extract

T.co.

Kiełczewski et al. (1979)

40. C. paniculata L.

Methanol extract

T.co.

Kiełczewski et al. (1979)

41. C. pannonica (Heuff.) Hayek

Methanol extract

T.co.

Kiełczewski et al. (1979)

123

Phytochem Rev (2012) 11:543–566

555

Table 3 continued Plant species

Solvent/product

Insect species

Reference

42. C. polyacantha Willd.

Methanol extract

T.co.

Kiełczewski et al. (1979)

43. C. pratensis Thuill.

Methanol extract

T.co.

Kiełczewski et al. (1979)

44. C. pseudophrigia C.A. Mey 45. C. pullata L.

Methanol extract Methanol extract

T.co. T.co.

Kiełczewski et al. (1979) Kiełczewski et al. (1979)

46. C. salicifolia M. Biel ex Wild.

Methanol extract

T.co.

Kiełczewski et al. (1979)

47. C. scabiosa L.

Methanol extract

T.co.

Kiełczewski et al. (1979)

48. C. seridis L.

Methanol extract

T.co.

Kiełczewski et al. (1979)

49. Chaenomeles sinensis Koehne

Methanol extract

A.u.j.

Han et al. (2006)

50. Chenopodium ambrosioides L.

Acetone extracts

R.d.

Malik and Mujtaba-Naqvi (1984)

51. Chromolaena odorata (L.)

T.ca., S.o.

Owusu (2001)

52. Chromolaena odorata (L.)

Hexane ? isopropyl alcohol extract Powder

P.t., S.o.

Niber (1994)

53. Chrysanthemum balsamita L.

Methanol extract

T.co.

Kiełczewski et al. (1979)

54. Chrysanthemum coronarium L.

Essential oil

T.co.

Haouas et al. (2012)

55. Chrysanthemum fuscatum Derf.

Essential oil

T.co

Haouas et al. (2012)

56. Chrysanthemum grandiflorum Tzvelv.

Essential oil

T.co.

Haouas et al. (2012)

57. Cinnamomum cassia Blume

Acetone extract

C.m., L.s., S.o., T.co.

Su (1985)

58. Cissampelopsis owariensis Beauv. ex DC.

Powder

P.t., S.o.

Niber (1994)

59. Citrus limon L.

Hexane ? isopropyl alcohol extract

T.ca., S.o.

Owusu (2001)

60. Citrus limon L.

Leaf powder

T.g

Jood et al. (1993)

61. Clematis armandii Franchet

Methanol extract

T.ca., S.z.

Liu et al. (2007)

62. Clerodendron fragrans (Vent.) R. Br.

Pertroleum ether extract extract

S.o.

Roychoudhury (1993)

63. Clerodendron siphonanthus R. Br.

Methanol extract

S.o.

Roychoudhury (1993)

64. Cnidium officinale Makino

Methanol extract

A.u.j.

Han et al. (2006)

65. Cocos nucifera L.

Leaf extracts

Rani et al. (2011)

66. Coriaria nepalensis Wall.

Petroleum ether extract

S.o.R.d., R.ca., C.ch. S.o.

Roychoudhury (1993)

67. Curcuma longa L.

Essential oil

S.o., R.d., T.ca.

Tripathi et al. (2002)

68. Curcuma longa L.

Essential oil

R.d.

Jilani and Saxena (1990)

69. Curcuma zeodaria (Berg.)

Essential oil

S.z., T.ca.

Suthisut et al. (2011)

70. Cymbopogon citratus Stapf.

Essential oil

S.o., T.ca

Stefanazzi et al. (2011)

71. Datura stramonium L.

Powder

P.t., S.o.

Niber (1994)

72. Dictamus dasycarpus Turcaz

Hexane extract

T.ca., S.z.

Liu et al. (2007)

73. Dictamus dasycarpus Turcaz

Methanol extract

T.ca., S.z.

Liu et al. (2007)

74. Didymocarpus podocarpa C.B. Clarke

Chloroform extract

S.o.

Roychoudhury (1993)

75. Dioscorea hypoglauca Palibin

Hexane extract

T.ca., S.z

Liu et al. (2007)

76. Dioscorea batatas Decaisne

Methanol extract

A.u.j.

Han et al. (2006) Liu et al. (2007)

77. Dryopteris crassirhizoma Nakai

Hexane extract

T.ca., S.z.

78. Echiochilon fruticosum Desf.

Essential oil

T.co.

Zardi-Bergaoui et al. (2008)

79. Elletaria cardamonum (L.) Maton.

Essential oil

T.ca., S.z.

Huang et al. (2000)

80. Elyonurus muticus (Spreng)

Essential oil

S.o., T.ca.

Stefanazzi et al. (2011)

123

556

Phytochem Rev (2012) 11:543–566

Table 3 continued Plant species

Solvent/product

Insect species

Reference

81. Entandrophragma candollei Harms (Kosipo)

Chloroform extract

T.co. T.g. S.g.

Błoszyk et al. (1995) Błoszyk et al. (1995)

82. Entandrophragma caudatum Sprague

Chloroform extract

T.co. T.g. S.g.

83. Erythrophleum suaveolens (Gull &Perr.)

Powder extract

P.t., S.o.

Niber (1994)

84. Eugenia caryophyllata Thunberg

Methanol extract

A.u.j

Han et al. (2006)

85. Evodia rutaecarpa Hook f. et Thomas

Essential oil

T.ca., S.z.

Liu and Ho (1999)

86. Evodia rutaecarpa Hook f. et Thomas

Hexane extract

T.ca., S.z.

Liu et al. (2007)

87. Evodia rutaecarpa Hook f. et Thomas

Metanol extract

A.u.j.

Han et al. (2006)

88. Foeniculum vulgare Gaertner

Metanol extract

A.u.j.

Han et al. (2006)

89. Geranium viscosissimum Fisch. & C.A.Mey.

Leaf powder

Z.s., S.o.

Weaver et al. (1995)

90. Gleditsia gabra L. 91. Glycyrrhiza gabra L.

Metanol extract Metanol extract

A.u.j. A.u.j.

Han et al. (2006) Han et al. (2006)

92. Grosshaimia macrocephala L.

Methanol extract

T.co.

Kiełczewski et al. (1979)

93. Hypericum ascyron L.

Ethanol extract

T.ca.

Liu et al. (2007)

94. Hyptis spicigera Lam.

Powder extract

P.t., S.o.

Niber (1994)

95. Illicium verum Hooker

Methanol extract

A.u.j.

Han et al. (2006)

96. Inula helenium L.

Methanol extract

A.u.j.

Han et al. (2006)

97. Jurinea alata Cass.

Methanol extract

T.co.

Kiełczewski et al. (1979)

98. Kaempferia galanga L.

Methanol extract

A.u.j.

Han et al. (2006)

99. Khaya anthoteca A. Juss

Chloroform extract

T.co. T.g. S.g.

Błoszyk et al. (1995)

100. Lantana camara L.

Petroleum ether

C.ch.

Saxena et al. (1992)

101. Lathyrus sativus L.

Flour

T.a.

Hasan and Khan (1988)

102. Litsea cubeba (Loureiro) Persoon

Hexane extract

T.ca., S.z.

Liu et al. (2007)

103. Litsea cubeba (Loureiro) Persoon

Methanol extract

T.ca., S.z.

Liu et al. (2007)

104. Lysimachia davurica Ledebour

Methanol extract

A.u.j.

Han et al. (2006)

105. Matricaria chamomilla L.

Water extract

S.g.

Ignatowicz and Wesolowska (1994)

106. Melaleuca quinquenervia (Cav.) S.T.Blake

Essential oil

T.ca.

Alonso-Amelot et al. (1994)

107. Melia toosendan Siebold et Zuccarini

Hexane extract

T.ca., S.o.

Liu et al. (2007)

108. Melia toosendan Siebold et Zuccarini

Methanol extract

T.ca., S.z.

Liu et al. (2007)

109. Mentha spicata L.

Leaf powder

T.g.

Jood et al. (1993)

110. Minthostachis mollis (Kunth) Griseb

Essential oil

T.ca.

Alonso-Amelot et al. (1994)

111. Momordica charantia L.

Hexane extract

T.ca., S.z.

Liu et al. (2007)

112. Monarda fistulosa L.

Leaf powder

Z.s., S.o

Weaver et al. (1995)

113. Myristica fragrans Houtt.

Essential oil

T.ca., S.z.

Huang et al. (1997)

114. Narcissus tazetta L.

Hexane extract

T.ca., S.z.

Liu et al. (2007)

115. Narcissus tazetta L.

Methanol extract

T.ca., S.z.

Liu et al. (2007)

116. Nardostachys chinensis Batalin

Methanol extract

A.u.j.

Han et al. (2006)

117. Nicotiana tabacum L. 118. Ocimum basilicum L.

Alkaloid fraction Hexane ? isopropyl alcohol extract

T.ca. T.ca., S.o.

Archna et al. (1995) Owusu (2001)

119. Ocimum viride Wild

Hexane ? isopropyl alcohol extract

T.ca., S.o.

Owusu (2001)

120. Paeonia suffruticosa Andrews

Methanol extract

A.u.j.

Han et al. (2006)

121. Phaseoulus vulgaris L.

Whole meal

C.m.

Karbache et al. (2011)

123

Phytochem Rev (2012) 11:543–566

557

Table 3 continued Plant species

Solvent/product

Insect species

Reference

122. Picris echioides L.

Chloroform extract

T.co., T.g., S.g.

Daniewski et al. (1989)

123. Pisum sativum L.

Protein, fibre, starch fractions

S.o., T.ca., C.f.

Fields et al. (2001)

124. Pisum sativum L.

Protein fraction

S.o., T.ca. R.d.

Pretheep-Kumar and Mohan (2004) Liu et al. (2007)

125. Polygonum aviculare L.

Hexane extract

T.ca., S.z.

126. Polygonum aviculare L.

Methanol extract

T.ca. S.z.

Liu et al. (2007)

127. Punica granatum L.

Hexane extract

T.ca., S.z.

Liu et al. (2007)

128. Punica granatum L.

Methanol extract

T.ca., S.z.

Liu et al. (2007)

129. Quasia. africana Bail.

Chloroform extract

T.co.T.g.S.g

Błoszyk et al. (1995)

130. Quisqualis indica L.

Hexane extract

T.ca., S.z.

Liu et al. (2007)

131. Rhaponticum pulchrum Fisch et Mey.

Chloroform extract

T.co., T.g., S.g.

Cis et al. (2006)

132. Rheum coreanum Nakai

Methanol extract

A.u.j.

Han et al. (2006)

133. Rhododendron molle G.Don.

Hexane extract

T.ca., S.z.

Liu et al. (2007)

134. Rhododendron molle G.Don

Methanol extract

T.ca., S.z.

Liu et al. (2007)

135. Ricinus communis L. 136. Salvia officinalis L.

Powder Water extract

P.t., S.o. S.g.

Niber (1994) Ignatowicz and Wesolowska (1994) Kłys´ (2004)

137. Salvia officinalis L.

Powdered leaves

R.d.

138. Sambucus nigra L.

Water extract

S.g.

139. Sapindus saponaria L.

Cexane, chloroform

T.ca.

Alonso-Amelot et al. (1994)

140. Schizonepeta tenuifolia Briquet

Methanol extract

A.u.j.

Han et al. (2006) Liu et al. (2007)

Ignatowicz and Wesolowska (1994)

141. Scutellaria baicalensis Georgi

Methanol extract

T.ca., S.z.

142. Securidaca longepedunculata Fresen

Powdered root bark

S.z., C.m.

Stevenson et al. (2009)

143. Schunus molle L. var. areira (L.)DC.) 144. Sida acuta Burm.

Leaf anf fruit essential oils Powder

S.o. P.t., S.o.

Benzi et al. (2009) Niber (1994)

145. Solanum nigrum L.

Powder

P.t., S.o.

Niber (1994)

146. Sophora flavescens Aiton

Hexane extract

T.ca., S.z.

Liu et al. (2007)

147. Sophora flavescens Aiton

Methanol extract

T.ca., S.z.

Liu et al. (2007)

148. Sorgum bicolor L.

Phenolic fraction

S.o.

Ramputh et al. (1999)

149. Stemona japonica Miquel

Methanol extract

A.u.j.

Han et al. (2006)

150. Stemona sessifolia (Miquel)

Hexane extract

T.ca., S.z

Liu et al. (2007). Stefanazzi et al. (2011)

151. Tagetes terniflora Kunth

Essential oil

S.o., T.ca.

152. Stemona sessifolia (Miquel)

Methanol extract

T.ca. S.z.

Liu et al. (2007)

153. Tephrosia candida CD

Methanol extract

S.o.

Jha and Roychoudhury (1989)

154. Terminalia catappa L.

Leaf extract

Rani et al. (2011)

155. Theobroma cacao L

Hexane ? isopropyl alcohol extract

S.o., R.d., T.ca.C.ch. T.ca., S.o.

156. Tripterygium wilfordii Hook f.

Hexane extract

T.ca, S.z.

Liu et al. (2007)

157. Tripterygium wilfordii Hook f.

Methanol extract

T.ca., S.z.

Liu et al. (2007)

Owusu (2001)

158. Torreya grandis Fortune

Hexane extract

T.ca., S.z.

Liu et al. (2007)

159. Zanthoxylum piperitum de Candolle

Methanol extract

A.u.j.

Han et al. (2006)

160. Zanthoxylum planispinum Siebold. & Zucc.

Methanol extract

S.o.

Jha and Roychoudhury (1990)

123

558

Phytochem Rev (2012) 11:543–566

Table 3 continued Plant species

Solvent/product

Insect species

Reference

161. Zanthoxylum schinifolium Siebold et Zuccarini

Methanol extract

A.u.j.

Han et al. (2006)

162. Zingiber zerumbet Smitt

Essential oil

S.z., T.ca.

Suthisut et al. (2011)

A.u.j.—Attagenus unicolor japonicus, C.h.—Carpophilus hemipetrus, C. ch.—Callosobruchus chinensis, C.m.—Calosobruchus maculatus, L.s.—Lasioderma serricorne, P.t.—Prostephanus truncatus, R.d.—Rhyzopertha dominica, S.g.—Sitophilus granarius, S.o.—Sitophilus oryzae, S.z.—Sitophilus zeamais, T.a.—Tribolium anafe, T.bis.—Tineola biseliella, T.ca.—Tribolium castaneum. T.co.—Tribolium confusum, T.g.—Trogoderma granarium, T.m.BearingTenebrio molitor, Z.s.—Zabrotes subfasciatus

results obtained for another species. Molecular modeling may help to solve this problem in the future. Such trends determined as QSAR—(Quantitative Structure–Activity Relationship) can be described as a mathematical searching for the relation between the expected biological activity and the corresponding chemical structure. Any reliable model combining the biological activity with the chemical structure of examined substances would be useful for predicting associations. Moreover, appropriate interpretation can provide information on general functioning of studied biological properties, e.g., mapping shape of the active area of the receptor, designing different chemical substances that structurally better fit a receptor, and finally resulting in a stronger feeding deterrence. Antifeedant activities of the compounds can differ between two developmental stages. Experiments with larvae and adults of Tribolium confusum frequently indicate that larvae were more sensitive to most compounds than adults. Data to date definitely confirms previously reported opinion, that there are no specific structures or structural moieties responsible for the antifeedant activity (Nawrot and Harmatha 1994). It is still more evident, that nearly all structural types of low molecular substances (predominantly secondary metabolites) are involved in this biological effect. The most abundant structural types are simple aliphatic substances, terpenoids, steroids, simple and complex polyphenols, quinones, phenylpropanoids and their biogenetically related derivatives, e.g. lignans, coumarins, flavonoids, rotenoids, and several other specific types, such as alkaloids, organo-sulfur compounds, nitroalkanes, and others (as indicated in Table 2). They occur most frequently in oxidized forms, as alcohols, aldehydes, ketones, carboxylic acids, esters or lactones, often also as epoxides, peroxides and other oxo- or oxyderivatives, occasionally containing one or more isolated or conjugated double bonds. In some cases, the

123

functional groups can form certain conjugates (e.g., esters or glycosides), as well as oligomers (widespread in polyphenols or phenyl alkanoids). The chemical reactivity and/or stability of such compounds depend on the number and position of functional groups. This may reflect generally also in their biological activity. However, a direct relation between the chemical reactivity and antifeedant activity, have not yet been reported, watching publications coming from various laboratories, including ours (Koul 1982; Norris 1986; Vigneron 1978; Nawrot and Harmatha 1994). Some generalizations, however, are possible. For example, many antifeedants possess oxidized functional groups (carbonyls) conjugated with a double bond or other unsaturated structural moiety. Such molecules usually form Michael adducts with the amino, sulfhydryl, or even hydroxyl nucleophilic moiety of the receptor binding side. Reversibility of such reaction, namely in the case of sesquiterpenic exomethylene lactones (e.g. eupatolide or helenalin, Table 2) preferentially generate feeding deterrence, rather than direct toxicity (Harmatha and Samek 1982, Nawrot and Harmatha 1994). Michael addition can also explain the mechanism of activity of quinones (Norris 1986), as well as other structurally activated carbonyls. In the case of unsaturated dialdehydes (as polygodial in Table 2, or isovelleral in Fig. 1), produced antifeedant activity in insects, as well as a hot taste to humans (Kubo and Ganjian 1981), which can be explained by mechanism other than that one derived from Michael addition (Cimino et al. 1987). Interesting chemical reactions between active sesquiterpene dialdehydes (see isovelleral in Fig. 1), their inactive hemiacetal precursors (see stearoylvelutinal in Fig. 1) and furano or lactone antifeeding active artifacts (e.g., lactarorufin type derivatives, Fig. 1; Table 2) were observed, and their role in the

Phytochem Rev (2012) 11:543–566

559

Fig. 1 Chemical structures of selected compounds representing various structural types of antifeedants

O O H O

R

O

OAc

O O

O

OH OH

O O bakkenolide A, R: H homogenolide B, R: tigloyl

O

trilobolide

OH

OR CHO

O

O CHO

O velutinal, R: H stearoylvelutinal, R: stearyl

isovelleral OH

lactarorufin A

O OH

HO

BzO AcO

R

O

H HO

O HO

O O

safrol, R: CH2CH=CH2 R: various propanoids

10-deacetyl-baccatin A OH

O CH3O

O O

O RO

O H

H

OCH3

O O

OCH3 O

carthamoside, R: Glc O + N

cubebin OR

O 3-nitropropionic acid (NPA), R: H ; corollin / coronillin, R: Glc-(NPA)2

chemoecological defense system was proposed by Sterner et al. (1985), and for the stored products insect pests tested by Daniewski et al. (1995). The wide variety of unrelated structures active as antifeedants, the rather insufficiently examined biogenetic origin of the active metabolites, their possible phytoalexine character, and the different chemical reactivity related to their mechanisms of activity,

together with the special feeding and ecological characteristics of stored product insects, still prevent any generalization and extrapolation of results reported to date. Further screening and targeted tests are required for accumulating sufficient knowledge in this field. Nevertheless, some findings related to particular structural types were already observed and discussed (Nawrot and Harmatha 1994). Selected

123

560

examples corroborating our own experience are presented also here in the Fig. 1. The most extensively studied structural type in our own and some collaborating laboratories were sesquiterpene lactones (see references in Table 2). The feeding inhibitory action of these compounds, as mentioned above, is mainly due to their specific reactivity (Michael addition). However, this concerns only the a-exomethylene-c-lactones. If comparing such lactones with other types possessing unconjugated exomethylene double bond (as in bakkenolide A, Fig. 1; Table 2), or containing specific diol moiety (as in trilobolide, Fig. 1; Table 2), one can observe, that the conjugated a-exomethylene moiety is not so important for the feeding deterrence, as has generally been assumed. Moreover, the a-exomethylene-c-lactones are prevailably cytotoxic, in contrary to the above mentioned nonconjugated or substituted lactones. Thus, the less active antifeedant trilobolode (Fig. 1; Table 2) could be more suitable for a practical use, especially if taking into consideration its immunostimulatory activity (Kmonı´cˇkova´ et al. 2010), that is beneficial for protecting the stored food products. The solubility effect, influenced by the often present ester side chains in sesquiterprnoids, may play a more significant role for the activity. The highest activity has often been recorded in compounds lacking any polar groups or substituents, as can be demonstrated by the simple spirolactone bakkenolide A (Fig. 1). It is largely evident that lipophilicity may increase the antifeedant activity. Very similar experiences have been observed with selected polyphenols. Namely, simple phenylpropanoids, such as safrol (see Fig. 1; Table 2), and their various derivatives, as reported by Harmatha and Nawrot (2002), or methoxylated analogues of asarone type reported by Poplawski et al. (2000), as well as their specific dimer compounds, lignans, displayed the highest activity when containing nonpolar substituents. Butyrolactone or hemiacetal type of lignans, such as cubebin and carthamoside (Fig. 1; Table 2), were more active than their reduced diols (Harmatha and Nawrot 2002) or other transformed derivatives, as reviewed earlier (Nawrot and Harmatha 1994; Harmatha and Dinan 2003). Lignans with nonpolar methoxy or methylenedioxy substituents located at the benzyl moiety were in many cases more active, than their related hydroxy or glycosidic derivatives, e.g., comparing activities of carthamoside with its aglycone

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Phytochem Rev (2012) 11:543–566

carthamogenin (Harmatha et al. 2007). In particular, the methylenedioxyphenyl (piperonyl) structure moiety significantly increased the activity. Evidently, the well-known synthetic synergist, piperonyl butoxide, a structurally transformed analogue of safrol (see Fig. 1), is the most efficient antifeedant up to now tested in our model (Harmatha and Nawrot 2002). Biogenetically related coumarins and furocoumarins from Angelica sylvestris and Coronilla varia have also been tested (Harmatha et al. 1991, 1992). The strongest antifeeding activity was observed with the simplest structures: coumarin, psoralen and bergapten (Table 2). Their activities are comparable with the strongest sesquiterpene or lignan type antifeedants, as well as with the mostly recognized antifeedant azadirachtin (Harmatha et al. 1991; Morgan 2009). Structurally related rotenone (Table 2) and its derivatives with chloro, chloromethyl and formyloxy substituents and even some deoxy, dehydro or seco derivatives were also tested (Nawrot et al. 1989). Evaluation of their structure–activity relationships confirmed, that the natural rotenone was more effective than any of its structurally modified polar derivatives. Rotenone showed the best activity in both choice and no-choice tests. The 3-nitropropionates of glucose (Fig. 1), along with coumarins and cardenolides, as main constituents of Coronilla varia, were also tested as antifeedants (Harmatha et al. 1992). The best activity was achieved by the free 3-nitropropionic acid itself (Fig. 1; Table 2), the most important defensive compound of this plant. The wide variety of relatively different chemical structures that are active against stored product insects is not surprising, considering the complexity of inhibitory biochemical profiles, and often also substantial differences of these profiles between the insect species (Jermy 1983). Such profiles, generally constituted of several substances, are presumably interactive with each other acting as agonists, antagonists or synergists in their effect on the sensory system of insects. Probably, only a combination of antifeedants will better fulfill the many criteria for an ideal antifeedant (van Beck and de Groot 1986). Another similarly relevant criterion, concerning mainly the potential application as a practically used antifeedant, is the low toxicity level, or even high pharmacological potential. This may be a deciding factor for selecting optimal antifeedants, as indicated

Phytochem Rev (2012) 11:543–566

above in the case of trilobolide (see Fig. 1). Even more attractive example is the diterpenoid, 10-deacetylbaccatin A (see Fig. 1; Table 2), structurally related to the clinically used antitumor drug Taxol. Series of diterpenes from Taxus baccata were effective when tested against storage pest insects by Daniewski et al. (1998). Similarly, our selection of lignans was based upon the above mentioned criterion; carthamoside (Fig. 1) comes from a widely used medicinal plant Leuzea carthamoides, and cubebin (Fig. 1) from nutraceutically valuable plant Piper cubeba (Harmatha et al. 2007; Harmatha and Nawrot 2002).

Perspectives for research and practical use Some papers on the practical use of antifeedants against butterfly larvae appeared in the 1960s and 1970s (Ascher and Nissim 1965; Wolfenbarger et al. 1968; Ascher 1979). Some derivatives of azadirachtin were tested against arable crop pests (Isman 2002). In order to perform field experiments, a sufficient amount of the tested substance is needed. The simplest use of feeding inhibitors is a direct application as a row plant powder, or application as water or oil extracts. Golob and Webley (1980) described more than 160 materials used for the protection of small amounts of agricultural products against pests. Such products are being used now and will be used in the future on small farms in developing countries. The plants mentioned in this review are palearctic, nearctic and tropical in distribution, and readily available to phytochemists all over the world for chemical analysis and structural identification of new compounds. Till now, antifeedant activity of about 1,000 plant compounds have been tested against insects significant in agriculture, forestry, public health, and animal breeding. The most active of these need to be further tested. Based upon the known activity and chemical structure, the best molecules can be chosen and commercialized. Hopefully, this review might help achieve this goal. At the present stage of research, it is difficult to predict what may be possible in the practical application of antifeedants. One can hope that they may be used for protection in the sowing seed and packaging of commodities (Błoszyk et al. 1990). Antifeedants may not be likely to replace insecticides and become the only products used for insect control, but in the

561

future, several techniques (alternative methods) might be used together to control pests in storehouses with antifeedants as one component of an integrated pest management program (Weaver and Subramanyan 2000). In addition to it, toxicological studies are needed to determine the safety of antifeedants as food protectants. The modern approach in stored product protection is the integration of methods with the ultimate goal of eliminating insecticides and fumigants. Feeding or egg-laying inhibitors may be synchronized for use together with attractants to cause substantial behavior change. The presence of these inhibitors in stored food may be the reason for insect migration, delay of egg deposition or reduction of food intake (Cox 2004). In natural ecosystems, desensitization (habituation) of insects to feeding deterrents (Jermy 1990; Suthisut et al. 2011) and variation in resistance (Arnason et al. 1994) can be expected, as well as rapid decomposition of natural compounds. Similarly, all this is likely in the ecosystems of storage insects, too. The potential for commercialization of botanical pesticides and their possible future utilization are described in some of the latest reviews (Isman 2006; Isman et al. 2011; Talukder 2006; Guleria and Tiku 2009; Rajashekar et al. 2012). The first step is to find activity under laboratory conditions. The next step is the isolation and identification of the molecular structure, synthesis and structural modification of a molecule, and finally formulation of commercial forms. Success depends on the financial costs, the commercialization process, and expected profits. Acknowledgments We thank Drs. Zofia and Don Griffiths for improving English and Dr. David W. Hagstrum (Kansas State University) for correcting final version of the manuscript.

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