, 8 A in Biom- 2,14–16 . associated Lymnaea and values of these 50 Pueraria peduncularis , Bulinus Wedelia trilobat and , against GAS in rice fields a A. artemisiifolia ,and In addition, many species may be useful for population species have molluscicidal activity. have a molluscicidal effect on ,andthe24-hLC 11–13 Biomphalaria A. artemisiifolia and significant molluscicidal activity against Chenopodium quinoa Ambrosia . 9 a Mikania micrantha Hualiang He , A. artemisiifolia d A. artemisiifolia Ambrosia Ambrosia maritima Sesquiterpene lactones and thiophenes have been found ; molluscicidal activity 10 , while the weights, lengths and widths of GAS were –1 Correspondence to: Y Li,China. E-mail: [email protected] Hunan Agricultural University, Changsha 410128, Hunan Provincial Engineering & Technologyand Research Formulation Processing, Center Hunan for Agricultural University, Biopesticide Changsha, China HunanCo-InnovationCenter for Utilizationof Botanical Functional Ingredients, Changsha, China Changsha Plant Protection & Quarantine Station, Changsha, China State Key Laboratory for Biology ofPlant Plant Protection, Diseases Chinese and Academy Insect of Pests, Agricultural Institute Sciences, Beijing, of China ∗ c a d b compounds of some Extracts of fields. to be the bioactive compoundsactivity responsible of for the molluscicidal phalaria alexandrin have been found to have potentialtrolling value as GAS, molluscicides such for as con- snail species of the genera Jatropha elliptica as a potential resource 8 3 In (Lamarck) 1 Con- 4 Zhongshi Zhou, Pomacea canaliculata (Lamarck)] is a,c L., is native to North , an invasive in and , is highly toxic to the golden apple snail (GAS; powders did not negatively affect the growth and development of rice but they reduced plant material has stimulated Naylor reported that the crop ; golden apple snail; 2 Rui Huang, Pomacea canaliculata 90% when the density of GAS was ≥ a,b Ambrosia ) in laboratory tests. However, little is known about the chemical components of : 944–949 www.soci.org © 2017 Society of Chemical Industry ) of the extracts against GAS was 194.0 mg L 2,5–7 50 74 Ambrosia artemisiifolia a,b* 2018; Ambrosia artemisiifolia Ambrosia artemisiifolia

Common , and under laboratory conditions. RESULTS: damage to riceconcentration caused (LC by GAS. Extracts had moderate acute toxicity but potent chronic toxicity. The 24-h 50% lethal with the molluscicidalmolluscicidal activities activity of powders, methanol or extracts, and about individual compounds from its potential application for GAS control in rice fields. This study evaluated the America. It can grow rapidly and spread aggressivelysoil in types a and it variety is of a problematic invasive weed in Europe and Asia. studies aiming to evaluatechemistry. Previous the studies have reported potential that the secondary usefulness plant of its plant Pest Manag Sci The ready availability of GAS control isluscicides, mainly but achieved the using molluscicidenon-target products synthetic organisms, are chemical and expensive, harmful mol- toxic to to the rice ecosystem. The golden apple snail [GAS; 1 INTRODUCTION a serious pest on riceto and be other one aquatic of plants the and 100 is worst invasive considered alien species in the world. Abstract BACKGROUND: Wenbing Ding, Pomacea canaliculata Ambrosia artemisiifolia for management of golden apple snails, Pomacea canaliculata (wileyonlinelibrary.com) DOI 10.1002/ps.4792 Research Article Received: 28 June 2017 Revised: 22 October 2017 Accepted article published: 17 November 2017 Published online in Wiley Online Library: 16 January 201 standcouldbereducedby sequently, some studies have evaluated the potentialmolluscicides of because they botanical biodegrade more rapidly and areronmentally envi- friendly. rice paddy fields, the GAS hascan high increase fecundity, and rapidly its under populations pletely defoliate favorable and conditions. kill young GAS riceing can seedlings, rice significantly com- yields reduc- and farmer profits. significantly affected by exposure toidentified a as sublethal the concentration most (100 mg/mL). active Psilostachyin, molluscicide psilostachyin components B, in and the axillaxin aerial were parts of 8 per square meter and snail length ranged from 10 to 40 mm. Youzhi Li Keywords: Supporting information may be found in the online version of this article. purified compounds were 15.9, 27.0, and 97.0 mg/L, respectively. CONCLUSION: The resultsmanagement indicate of GAS that in rice chemical fields. © 2017 compounds Society of produced Chemical Industry by

944 945 )on Each 100%. MeOH 2 deaths × − plastic boxes ) on the other 3 6 m, previously C with a 12:12 h plants were col- ∘ Glycine max × 2 ± 20 cm values, respectively). L. sativa × A. artemisiifolia 50 25 C with a 12:12 h (light:dark) ∘ × 2 ± ) plants (variety: Xianyou 63) were was applied to each plot, respec- , juvenile (7-day-old) snails were 2 wileyonlinelibrary.com/journal/ps mortality rate of control group) Ambrosia artemisiifolia − Oryzasativa (total deaths in the treated group = www.soci.org P. canaliculata powder/667 m immersed in aqueous suspensionsnegative of control tea groups were saponin24 immersed h, (4 mg/L) in the and treated distilled snails water.100 were mL After of placed distilled water in to recover. Snails a thatan did separate not additional recover container after 24 with h in distilled water were scored as dead. transplanted at a density of 180to rice the plants experiments, in each all testwere snails plot. manually Prior naturally removed. present in each test box extract against exposed to sublethalwere concentrations equal (50 to 1% and and 100 6% mg/L, of which the 72-h LC (light:dark) photoperiod. 2.4 Sublethal toxicityTo assay determine the chronic toxicity of the tively. Each plot had independent irrigation andto drainage avoid systems spreading the powderstreatments. and Other contamination field of the cultivationand other processes, pesticide applications, including were conducted fertilizer innon-experimental the plots. same The way pesticides used as were in directedspecies at other pest than snails. Seven days7-day-old after juvenile treatment, snails a were total placed of in 50 used each to plot. Plastic cover film each was plotwithout snails bed and the to dry prevent powder were snail used ashad escape. controls. a The randomized Three study complete plots block design andreplicated each three times. treatment The was eggs laid were collected dailyplot from each before all GAS died. Theproduction, number of and surviving the snails, total yields egg of rice were recorded at the end of and immersed in 1 L of theAnother liquid group of of each 50 treatment snails concentration. was maintainedas in dechlorinated the water negative control.temperature was maintained During at 26 the experiment, the laboratory photoperiod. The snails were3daysofeachweekandonfreshlettuce( fed on soybeandays. ( The individual wet weightwidth of of each the shell snail were and measured every theexperiment 5 length days. was The and duration 35 days. of the Toxicity wasmortality expressed rate as calculated the corrected usingmortality rate the (%) following formula:in the adjusted control group)/(1 Before measuring the wet weight of GAS,of the water the on the snails surface wasthe dried snail with was filterwere examined weighed paper using the with three Moticam 2306 times,Electric an stereomicroscope (Motic Group and analytical Co.,Ltd., then Xiamen, balance. China)and and width The the of equatorial the shells length shellsPLUS were 2.0 calculated software using (Motic Electric the Group MOTIC Co.,Ltd., IMAGES Xiamen, China). 2.5 Field experiments Field experiments were conductedProvince, in China, Pingjiang during County,October the Hunan 2014. rice Eighteen growing cementconstructed ponds season for rice of from breeding, 4 wereThree-week-old m July rice selected ( to for the experiment. lected and placed inground the into shade fine to powder with dry, particlemesh. and sizes At the ranging 7 days from dried after 20 parts rice toA. transplantation, 40 were 0, artemisiifolia 5, 10, 15, and 20 kg of A total of 50 snails were placed in 35 treatment was replicated three times. Duringlaboratory the temperature experiment, was maintained the at 26 A. L.) we investi- against GAS A. artemisiifo- 20 C with a 12:12 ∘ 12’ E) in August 5%), the newly 2 ∘ Lactuca sativa and isolated plant ± ± flowering season, the Pomacea canaliculata 51’ N, 113 ∘ A. artemisiifolia exhibited high toxicity against powder to control GAS on this ) were collected from Beisheng 10.0 kg) were used for labora- = A. artemisiifolia A. artemisiifolia and a patent has been applied for in Aqueous suspensions of the methanol plants were placed in the shade to dry. 200.0 kg) were used for the field exper- 16 = for management plants were collected from Huangshi Town, 21 C; relative humidity 70 : 944–949 © 2017 Society of Chemical Industry ∘ A. artemisiifolia P. canaliculata A. artemisiifolia 2 74 powder or the chemical components associated ± 25’ E). After indoor hatching of the egg masses ∘ 2018; material against GAS. The assay was a slightly mod- Little else is known about the potential field effectiveness and demonstration of molluscicidal activity, 17 15’ N, 113 ∘ A. artemisiifolia 18,19 Ambrosia artemisiifolia Based on our previous phytochemical studies of 60 mesh, and then macerated with 3 folds of methanol (To 1500 (light:dark) photoperiod and fed fresh lettuce ( 2012 and 2014. During the hatched GAS were reared in an incubator at 26 average plant height wasAugust about 2012 60 (total cm. dry The weight plants collected in (temperature 28 Town, Liuyang City, Hunan(28 Province, People’s Republic of China tory experiments, including plant identification, methanolpreparation, extract and compound isolation. Plants2014 collected (total in dry August weight 2.3 Molluscicidal activity A molluscicidal bioactivity assay was used to test the efficacy of iment. A voucherHunan specimen Agricultural University. (No. 20120821) was depositedThe at dried parts were ground into< a fine powder with particle sizes mL of methanol addat 500 room g temperature of for the 24 h.paper, powder) and The in then extract concentrated a was to filtered 3000-mL drynessin using beaker under filter a reduced rotary pressure evaporator. Thespecimen jar. dried extract was stored in a labeled artemisiifolia ified version of the methodnization described by (WHO, the 1965). World Health Orga- compounds were freshlythe prepared results in of distilled preliminary experiments,to water. the Based 800, extracts on were 400, diluted and 200, solutions 100 of and12.5 the and 50 compounds mg/L 6.25 were mg/L inwere diluted in immersed distilled in distilled to water each water 100, treatment. (50 (5 mL), 50, Positive mL). control 25, Twenty-five groups snails were China for the use of basis. Pest Manag Sci 2.1 Snails EggmassesofGAS( GAS in a laboratory test, 2 MATERIALS AND METHODS 2.2 Plant material Ambrosia artemisiifolia for 7 days. Seven-day-old juvenile snailsbetween that 1.0 had and a 3.0 shell mm were length used of for further experiments. Miluo City, Hunan Province, China (28 Ambrosia artemisiifolia few saponins and alkaloids haveactive been components. One identified study as demonstrated theing water that effective extracts of cold and boil- gated the application of plant powders in riceWe fields to also control GAS. studied the molluscicidaland activities purified single of compounds methanol from extracts under laboratory conditions. The results mayregarding, and stimulate suggest new new approaches ideas to, the useand of the active powders compounds to manage GAS in rice fields. of with GAS toxicity. lia extracts from the aerial parts of ) 2 et al. 1.2 c 1.1 a 0.9 a 0.3 a 0.6 d 0.7 b 3.5 c 4.5 a 0.2 d 2.4 d 0.6 d 5.2 b ± 0.05), a ± ± ± ± ± ± ± ± ± ± ± : 944–949 < )valuesof P (kg/24 m 74 Yield of rice A. artemisi- 50 a standard error. ± 2018; 2.9 c 74.0 7.1 a 98.7 1.7 a 100.0 a goodness of fit tests, 0.6 d 1.0 1.7 d 6.0 4.0 b 91.0 software (version 9.5) 2 ± ± ± ± ± ± 𝜒 DPS c Mortality of GAS (%) Pest Manag Sci 0.7 c 16.7 0.6 b 17.8 ± ± 4.6 c 51.0 2.9 a 97.0 0.6 d 1.0 1.2 d 5.0 8.5 b 94.7 9.2 b 76.0 ± ± ± ± ± ± Inhibition of spawning (%) 62.7 (GAS) as well as on the yield of rice under field 0.05 level. Means within a column followed = P software, version 9.5). The 95% confidence interval, b Molluscicidal activity of a methanol extract from DPS P. canaliculata 0.05 level. Median lethal concentration (LC goodness of fit was found to be significant ( against 10-day-old GAS = 2 P 𝜒 Tea saponin (4 mg/L) served as the positive control. Thedatainthetablearemeansofthreereplications Control 0 d 0 d 1.0 Table 2. ifolia Treatment (mg/L)800 24 h 48 h 95.0 a 72 h b Data within a column followed bydifferent the at same the letter 5% are level not according significantly to Duncan Multiple Range Test. 200 20.0 400 58.0 50Tea saponin 1.0 100 4.0 0.6 c 95.9 1.2 a - 15.2 0.7 b 88.4 the significance of differences using heterogeneity correction factor was used inconfidence the limits. calculation of the compounds and extracts againstanalysis GAS ( were calculated by probit and regression equation arethe shown in Table 2 (see later). When values and degrees of freedom of the (Hangzhou Rui Feng Information Technology Co.,China) Ltd., Hangzhou, at the by different letters (Tablesthe 1 and 2) are significantly different at ± ± ± Total egg A. )and masses of GAS (g) www.soci.org W Ding 2 100%. × standard error. Data within a column followed by the same letter are not significantly different © 2017 Society of Chemical Industry ± total egg masses of − ), psilostachyin B ( 0.05) was used to deter- 1 < ) column chromatography 0.4 c 3.6 1.3 a 0 d 100 a 18.3 0.1 e 87.3 1.4 d 10.1 0.2 b 0 d 100 a 18.4 P - - - 18.4 18 ± ± ± ± ± powder on the mortality rate and egg masses of 0.4 -test were utilized to determine Mortality 77.6 95.3 t 57.4 91.6 rate of GAS (%) Psilostachyin ( 18,19 A. artemisiifolia was accomplished by activity-directed fractionation 1)-transformed, and the mortality rates were arcsine 2 2 2 ) possessed the greatest molluscicidal activity, with 2 2 Effect of a + x 12 The chemical structures of three active compounds. b (total egg masses of the control group 13.0 software (SPSS Inc., Chicago, IL, USA) was used for sta- = Control: no snails and no ragweed powder. The data in the table are means of three replications Inhibition of spawning was calculated on the basis of the egg masses of GAS, as described in the Methods. Percentages were transformed to arcsine square root values for 15 kg/667 m 10 kg/667 m 0 kg/667 m b c a Treatment 20 kg/667 m Table 1. conditions at the 5% level according to Duncan Multiple Range Test. 5 kg/667 m Control 2.7 Data analysis the respective mortality being 95.0,to 100 a and 100 60% mg/L after solutionInformation exposure Table of S1). The each structures compound ofshowninFigure1. the for three 24 compounds h are (Supporting axillarin ( the treated group)/total egg masses of the control group 2.6 Active chemicalPurification components in of the methanol 15 extracts compounds from the methanol extracts of with octa decylsilyl silicion (ODS-C artemisiifolia wileyonlinelibrary.com/journal/ps SPSS the growing seasons. Spawning inhibition was expressedcentage as according a per- to the following(%) formula: spawning inhibition Figure 1. tistical analysis. One-way analysisto of variance determine (ANOVA) the was significance used est of significant treatment difference effects. (HSD) test Tukey’smine hon- ( the significance of meantreatments. differences among The more data than for two theand wet width weight of the of shell, thewere the snails, log( total the egg length mass and grain yields of rice square-root-transformed to meet homoscedasticity assumptions. ANOVA. Scheffe’s test and the (CC), silica gel CC, Sephadex LH-20Uppsala, (GE Sweden) Healthcare CC Bio-Science or high-performance AB, liquid chromatography (HPLC). Chemical structures were confirmedresonance by (NMR) nuclear spectrometry magnetic as in previousInformation studies Figure (Supporting S1).

946 947 P. 50 A. P. canaliculata .(A)Mortalityrateof standard error; those within a ± A. artemisiifolia wileyonlinelibrary.com/journal/ps www.soci.org exhibited chronic toxicity against GAS. The mortality Compared with the positive control (tea saponin), only the max- 3.2 Acute toxicityThe assay of the methanol methanol extracts extracts7-day-old GAS (Table showed 2). The mortality molluscicidal ofafter GAS was exposure activity 95% within to 24 h against thewas 20% 800 mg/L in the MeOH 200 mg/L extracts,at MeOH 72 while extract h after treatment. mortality exposure GAS to mortality at the 400 24 g/L h. extract Similar wasThe higher results molluscicidal than that were activity of obtainedtime-dependent the effect. in MeOH the extract other had treatments. a dose- and imum concentration (800 mg/L) exhibited excellentactivity among molluscicidal the five concentrations of the extract. The 24-h LC value of the extracts againstTable 2, GSA, was based 194.0 on mg/L. the mortality data in 3.3 Sublethal toxicityThe of the methanol sublethal extracts treatmentsartemisiifolia with the methanolof extracts GAS from increasedto slowly a and sublethal dosage reachedMortality (100 28.5% mg/L was methanol during only extract) 2.4% exposure for when 35 days. GAS were exposed to 50 mg/L 2 A. ,the 2 ,GAS 2 0.05) in the total powder at 5 and in the untreated ≤ 2 P treated with sublethal concentrations of a methanol extract of Pomacea canaliculata and the control (0 kg pow- 2 snails). There were no differences P. canaliculata + 2 Ambrosia artemisiifolia for management : 944–949 © 2017 Society of Chemical Industry 74 caused a significant reduction ( 2018; snails) (Table 1). powder treatments. Snail viability was significantly 0.05) in relation to the control (Table 1). When the 2 + ≤ treated with concentrations of 50 and 100 mg/L for 35 days. (B–D) Growth indicators, (B) weight, (C) length and (D) width, of 2 P Growth inhibition of Moreover, the average grain weight of rice was 18.4 kg/24 m in the averagements of grain 15 and weights 20 kg powder/667 of m rice among the dose treat- Pest Manag Sci in the control (no snails) and 15.2 kg/24 m affected ( artemisiifolia dry powder dosage was 0, 5, 10, 15 and 20 kg powder/667 m 3RESULTS 3.1 Field experiments Three indexes, namelytotal the egg percentage mass of mortality GAS, of and GAS, rice yield, the were measured after Figure 2. canaliculata treated with concentrations ofcolumn 0, followed 50 by the and same 100 letter mg/L are for not 35 significantly days. different at The the data 5% in level according the to figure Duncan Multiple are Range means Test. of three replications Ambrosia artemisiifolia plots (0 kg powder/667 m mortality of GAS was 0.4,The 57.4, mortality 77.6, 91.6 of and snails 95.3%, amongdose-dependent respectively. different effects. treatments showed clear 10 kg/667 m egg mass (10.1 and 3.6, respectively) compared withgroup the untreated (87.3); at dosages of 15 and 20 kg powder/667 m der/667 m stopped laying eggs (Table 1). Theof corresponding spawning inhibition obtained rates for each treatment are shown in Table 1. ) 35 2 val- 𝜒 et al. have 50 Pomacea : 944–949 identified 74 is a possible ,withLC 2018; This study is the first Chenopodium quinoa A. artemisiifolia 36 A. artemisiifolia spp., and display bioactivi- A. artemisiifolia trypanocidal and leishmani- They are representative com- 59.0) 5.27 1290.3) 5.34 106.6) 4.61 33 Pest Manag Sci Psilostachyin and psilostachyin − − A. artemisiifolia 31 − . (95% CI) 29,30 Ambrosia 90 based on quinoa ( were therefore screened for molluscici- values, we found that psilostachyin and :310–319 (2008). cytotoxic, These data, combined with the toxicity to 50 27 32 DC in 1966. , with mortality of 73.3 and 50% following 15 O. hupensis DNA damage checkpoint. . [Online]. Available: http://www.iucngisd.org/gisd/ They inhibit nitrite accumulation in cell cultures, 2 Crop Prot 34 ; mg/L) at 24 h 90 A. artemisiifolia saponins. canaliculata speciesname/Pomacea. [13 April 2005]. Pomacea canaliculata and LC 50 Previous phytochemical studies on We conclude that methanol extracts of 1 Robert H, Global Database, Species profile: 2 Martín RS, Ndjoko K and Hostettmann K, Novel molluscicide against sesquiterpenes and sesquiterpene lactones ascompositions the main of chemical this species. GAS, indicate that psilostachyin and psilostachyinspectrum B of have a molluscicidal broad activitymore sensitive than and that GAS appears to be molluscicidal activity againstthe GAS. The snails mode ispsilostachyin of associated and action psilostachyin with against B, containedmolluscicidal the in property sesquiterpenes, indicates the that extracts. in This natural particular source that couldproducts. be It used could to be developsynthetic molluscicides used new for either integrated snail snail alone control management. or in combination with report that psilostachyin and psilostachyin B possess molluscicidal activity against GAS. Supporting information may be found inarticle. the online version of this REFERENCES and inhibit the G ACKNOWLEDGEMENTS This work was supported by theFoundation Hunan Provincial of Natural China Science (No.Science Foundation 2017JJ3114) of and China (No. the 31171908). National Nature SUPPORTING INFORMATION ponents of sesquiterpenes in ties such as anti-tumor, cidal activities. psilostachyin B were the mainfor bioactive the compounds responsible molluscicidal activity of extracts affected thecating growth the and presencechronic development of toxicity. Fifteen active of compounds ingredients GAS,extracts isolated of from associated indi- the with methanol the B, which areAmbrosia sesquiterpene psilostachya dilactones, were first isolated from ues of 27.0 andpsilostachyin 15.9 B mg/L, also respectively. have BothOncomelania molluscicidal hupensis psilostachyin activity and against theexposure to snail 100 mg/L. dal activity. Based on LC (LC 33.2) 63.4 (45.5 20.1) 37.0 (27.5 127.6) 455.7 (255.7 − − − (95% CI) LC A. 50 www.soci.org W Ding powder. , signifi- P. canaliculata 2 A. artemisi- values were: 50 © 2017 Society of Chemical Industry A. artemisiifolia powder was toxic 100 mg/L (100 ppm). > . The decreased fecun- A. artemisiifolia 2 demonstrated weak acute powder has the potential for values 50 A. artemisiifolia The powder was a strong inhibitor 17 A. artemisiifolia A. artemisiifolia 3%. < The mechanism of this phenomenon warrants 22 powder on rice field plants. The results suggest that Molluscicidal activity of active compounds against so we evaluated the possible allelopathic effects of 23–28 , Methanol extracts of Many reports have documented the allelopathy of The methanol extracts significantly inhibited GAS growth. There The lengths of GAS were significantly affected by exposure to Compound Slope LC Psilostachyin B 3.46 27.0 (21.9 CI, confidence interval. Psilostachyin 3.50 15.9 (12.6 Table 3. Axillarin 1.91 97.0 (73.6 use as a potent molluscicide in riceis fields. However, needed more research todetermine understand if the how powder affects non-target the organisms such powder as fish. affects GAS and to toxicity against GAS, with 72 h LC The powder may not haveand direct development negative but effects may on havedetrimental rice positive influences growth effects of by GAS. reducing Inclusively the summary, show the field that studies con- artemisiifolia the rice grain yield was not affected by ifolia further study. wileyonlinelibrary.com/journal/ps 4 DISCUSSION The field trial showed that methanol extracts for 35 daysthe (Figure controls 2A). was The mean mortality in dity and reproductive performancemainly in attributable the to rice a paddy declinewould fields in be the was an snail effective population,on method and egg for this mass snail productionof control. was A chromium. produced similar by effect high concentrations of snail spawning. At a treatment dose of 5 kg/667 m psilostachyin, 15.9 mg/L; psilostachyin B,97.0 27.0 mg/L mg/L; (Table and 3). axillarin, cant spawning inhibition100% (88.4%) at occurred. a This dose inhibition of was 15 kg powder/667 m to GAS, and thesevious results laboratory were consistent study. with those of a pre- 3.4 Active substances The toxicities of the active compounds psilostachyin, psilostachyin B and axillarin isolated from the MeOH extracts of was a significant decreasement in at snail 5 days weight compared in withreached the the control, 29.9% 100 and mg/L (Figure the 2B). treat- inhibition rate However,snail no weights was significant observed difference between in the the control. 50 mg/L treatment and sublethal concentrations of the extract.were Snail significantly lengths, shorter at in 29control. the days, 100 Snail mg/L lengths treatment in thanwere the in similar the 50 (Figure mg/L 2C). The treatmenton treatments and snail produced width the (Figure similar 2D). control effects (Figure 1) were determined in the laboratory. The LC However, the weights, lengthsicantly and affected widths by of the GAS sublethal were dosages signif- of the extracts. The

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