UNITED STATES ENVIRONMENTAL PROTECTION AGENCY 

WASHINGTON, D.C. 20460 

OFFICE OF 

PREVENTION, PESTICIDES AND 

TOXIC SUBSTANCES 

MEMORANDUM 

DATE: June 17,2008 

SUBJECT: Drinking Water Degradates Identification Memorandum for Spirotetramat 

(PC Code 392201)@P353728) 

FROM: Jos6 Luis Melhdez, Chemist 

Environmental Risk Branch V 

Environmental Fate and Effects Division (7507P) 

TO: George Kramer, Ph.D., Senior Chemist 

Registration Action Branch I 

Health Effects Division (7509P) 

This memorandum identifies the environmental degradates of spirotetramat that may be 

of exposure concern for drinking water assessment. These data are provided to help 

inform determinations of which environmental degradates are of risk concern for 

drinking water assessment in support of human health risk assessment. If you have 

questions about this memorandum, please e:mail Jos6 Meldndez or contact at 787-977- 

5856 or 787-799-3021. 

Spirotetramat (Table 1) is a new systemic broad spectrum insecticide intended for the 

control of sucking pests. It belongs to the chemical class of tetramic acid derivates 

(ketoenoles). According to the label, it is active primarily by ingestion against immature 

insect life stages and fertility of adult female insects may be reduced. Spirotetramat 

moves "through phloem and xylem to all plant tissues including new shoot, leaf and leaf 

growth.. ." This active ingredient is advised to be used as "a preventative treatment or 

timed to coincide with early threshold level in developing populations." The products 

MOVENTOTM, BY1 8330 150 OD and ULTORTM are formulated as a suspension 

concentrate or as an oil dispersion containing 1.25 lb a.i. per gallon or 2 lb a.i. per gallon, 

respectively. The maximum total application rate in a season is 0.4 lb a.i./A. The 

chemical may be applied by air, ground equipment or through chernigation. 

Two stereo isomers of spirotetramat, cis- and trans-isomer, are possible. The cis-isomer is 

the active substance. 

TEXT SEARCHABLE DOCUMENT
IWAC: cis-3-(2,5-dimethylpheny1)-8-methoxy-2- 

oxo-l-azaspiro[4.5]dec-3-en-4-y1 ethyl carbonate 

8-methoxy-2- oxo-l-azaspiro[4.5]dec-3-en-4-yl 

All the following appear to be major routes of degradation1 transformation for 

spirotetramat: hydrolysis in basic media, photolysis in natural water and biodegradation 

in aerobic and anaerobic environments (DT5O's range 4-23 days). Hydrolysis in 

neutral and acidic environments and photolysis in sterile water (8.6-32.5 days) are routes 

of transformation of less importance. Spirotetramat degrades to spirotetramat-en01 

(product of cleavage of the ester link), which also degrades moderately rapidly in aerobic 

environments and under photolytic conditions, and subsequently forms numerous 

degradates most of which have the basic backbone structure of spirotetrarnat (the most 

important are spirotetramat-ketohydroxy and spirotetramat-MA-amide in soils). It 

appears that spirotetramat's residues may be of higher concern than the parent due to 

spirotetramat's lability. Spirotetramat's residues have a potential to contaminate surface 

waters for a period of weeks to months posttreatment, and a relatively low potential to 

move subsurface and contaminate groundwaters. 

Spirotetramat has a moderate solubility in distilled water (33.4 mg/L) and a high 

solubility in various common organic solvents. Spirotetramat has a low vapor pressure 

and Henry's Law constant (4.2~10-l1 mm Hg at 20°C and 6.90 atm-rn3/mol at 20°C and 

pH 7, respectively). It is not likely to volatilize substantially. Spirotetramat's 1- 

octanoVwater partition coefficient is 324, indicating a low tendency to bioaccumulate. 

The hydrolysis behaviour of spirotetramat is strongly pH and temperature dependent. 

The rate of reaction increased with increasing pH. At 25"C, the experimental half-lives 

for the chemical were 32.5, 8.6 and 0.32 days at pH's of 4,7 and 9, respectively. In 

addition, hydrolysis rates increased with increasing temperature. The major hydrolysate 

is spirotetramat-enol, which appeared to be stable to hydrolysis in this and in a separate 

study conducted on the metabolite at pH's 4,7 and 9 and 25°C. 

Spirotetramat photolyzes relatively rapidly. Spirotetramat photolyzes with hydrolysiscorrected half-lives (DT5O's) of 3.0 and 0.22 days, in sterile buffer (pH 5) solution and 

natural water (pH 7.9), respectively. These half-lives (DT5O's) correspond to 9.3 and 
0.50 days, respectively, under environmental conditions (summer light in Phoenix, AZ). 

In sterilized natural water the major products observed were spirotetramat-enol(81.9% at 

1 day), methoxycyclohexanone (17.5% at 8 days) and methoxy-cyclohexylamino 

carboxylic acid (1 1.3 % at 10 days). In sterile buffer solution (pH 5), the major 

transformation products were spirotetramat-photo-cyclopentyl (maximum 42.9% at 7 

days), spirotetramat-photo-methyl (maximum 22.9% at 6 days), spirotetramat photoformyl (maximum 11.5% at 3 days) and spirotetramat-photo-methyl (maximum 19.3% at 

6 days). All these metabolites are the result of rearrangement of the parent. 

The soil photodegradation study available on spirotetramat was found to have certain 

deficiencies. Definite conclusions on the rate of photodegradation could not be derived 

fiom it. However, useful information on the identity of the degradates in the study may 

be obtained fiom the study. The following degradates were identified: spirotetramat-en01 

(maximum 10.1% at 1 day), spirotetramat-ketohydroxy (maximum 20.9% at 2 days), 

methoxycyclohexanone (maximum 10.0% at 2 days) and dimethylbenzoic acid 

(maximum 4.8% at study termination, 7 days). Methoxycyclohexanone and dimethylbenzoic acid were observed only in the irradiated samples. 

The major degradation pathway for spirotetramat under aerobic soil condition is 

hydrolytic cleavage of the ester bond, yielding spirotetramat-en01 (theoretically 

quantitatively). The latter is oxidized at the benzylic carbon to spirotetramatketohydroxy (maximum 24.0% at 1 day), which is hydrolytically opened to 

spirotetramat-MA-amide (maximum 5.2% at 1 day, one sample). In another possible 

pathway, demethylation of spirotetramat-en01 occurs to yield spirotetramat-desmethylen01 and subsequently spirotetramat-0x0-enol. Furthermore, oxidative spirotetramat-en01 

dimerization may occur to yield spirotetramat-en01 dimer 1 and spirotetramat-en01 dimer 

2. 

Spirotetramat degraded under aerobic conditions very quickly, with half-lives (DT5O's) 

of <l day in four soils. Furthermore, spirotetramat-en01 also degraded very quickly, with 

calculated half-lives DT5O's) of <l day in a separate study, in four soils. The half-lives 

DT5O's) for spirotetramat-ketohydroxy (range 1 -5-1 6.7 days) and spirotetramat-amide 

(range 0.03-5.4 days) were calculated fiom the results obtained in the study conducted on 

spirotetramat-enol. Carbon dioxide formation was 9.7-19.4% by 50 days in the study 

conducted with spirotetramat and 10.9-34.9 by 60 days in the study conducted with 

spirotetramat-enol. Volatiles were insignificant while non-extractable residues were 

important (both cases). In an outdoor metabolism study spirotetramat degraded with 

calculated half-lives (DT5O's) of 1.2 and 2.9 days. Spirotetramat-en01 was a maximum 

of 7.8%. The degradates spirotetramat-glyoxylic amide and dimethyl-benzoic acid were 

observed besides the aerobic soil metabolites. The latter two compounds were also 

observed in the soil photodegradation studies. 

In aquatic environment, under aerobic aquatic conditions, spirotetramat degraded with 

calculated half-lives (DT5O's) of 0.7 and 0.9 days in the total system. Spirotetramat was 

initially mostly associated with the aqueous phase. The metabolite spirotetramat-en01 

reached a maximum at 14 days at 99.0%, and decreased to <LOQ to 21 .O% at 120 days. 
The degradate spirotetramat-ketohydroxy was a maximum of 50.8% at study termination. 

It appeared to be relatively stable in the aerobic aquatic system. Minor transformation 

products included spirotetramat-MA-amide, spirotetramat-0x0-en01 and spirotetrarnatdihydroxy (58.7% in total system). Non-extractable residues increased throughout the 

study to a maximum of 33.9% at 120 days. Mineralization was a maximum of 13.5- 

24.0% at 120 days. 

In the anaerobic soil metabolism study, the metabolites observed were also generally 

consistent with the ones for the aerobic soil metabolism studies for spirotetramat and 

spirotetramat-enol, with respect to the metabolites observed. Under these conditions, 

spirotetramat dissipated quickly with a calculated half-life of <<I day. The major 

degradates were spirotetramat-enol, which increased throughout the study (maximum 

54.6% at 180 days) and spirotetramat-ketohydroxy (maximum 19.3% at 1 day). 

Mineralization was very low. Non-extractable residues were a maximum of 1 7.5% at 0.6 

days. In contrast, in an anaerobic aquatic metabolism system, spirotetramat completely 

degraded to spirotetramat-enol, which was found to be stable thereafter. The half-life for 

(DT50) the transformation of spirotetramat was calculated to be 2.8 days in the total 

anaerobic system. 

Spirotetramat is moderately mobile in five sterilized soils, with & values ranging from 

3.58-5.52 mLlg, Gc values between 184-437 mL/goc (mean 289 mLlgoc), KF values 

ranging from 3.70-4.79 (pglgoc)l(pglm~)lln, KFoC values ranging fi-om 1 59-43 5 

(pglgoc)/(pglm~)'" [mean 28 1 (pglgoc)/(pglm~)l"], ranging from 0.823 to 1.042 [(mean 

0.94 1 (pglgoc)/(pg/m~) lIn)l. 

Spirotetramat-enol, spirotetramat-ketohydroxy and spirotetramat-MA-amide were found 

to be more mobile than the parent, spirotetramat. The mobility of spirotetramat-en01 was 

assessed using a soil column leaching study. The chemical was found mostly in the 0-6 

cm soil depth (9.6-16.5%) and at low levels in the 6-12 ern soil depth (0.1-1.4%). In the 

leachate fractions, spirotetramat-en01 was a total of 0.1-2.8%. The estimated bc values 

for spirotetramat-en01 were between 27-99 mL/goc (mean 55 mL/goc) over four soil 

types (mobile). No definitive batch equilibrium test could be conducted on spirotetramaten01 because the chemical was labile during the adsorption phase. The degradate 

spirotetramat-ketohydroxy is mobile in five sterilized soils, with & values ranging fi-om 

0.529-2.28 mLIg, Koc values ranging fi-om 43.1-99.7 mL/goc (mean 65.3 mL/goc), KF 

values ranging fi-om 0.516-2.21 (pglg)/(pg/m~)ll~ KFoC values between 41 .O-99.1 

(pglgOc)l(pglm~)l" [mean 63.7 (pg/goc)l(pglm~)l/n] and l/n values close to unity (range 

0.915-0.929, mean 0.922). The Gc values were similar to the Freundlich adsorption 

constants KFOC. The degradate spirotetramat-MA-amide is highly mobile in five viable 

soils, with & values ranging fkom 0.064-0.179 rnLIg, results ranging fi-om 4.2-25.6 

mL/goc (mean 9.6 mLlgoc), & values ranging fi-om 0.075-0.179 (pglg)l(pglm~)lln, KFoc 

values 4.4-25.5 (pglgoc)/(pglm~)lln [mean 9.3 (pglgoc)l(pglm~)l~n] and lln results from 

0.80- 1.07 (mean 0.95, for four of the five soils the range 0.93- 1.07). The Koc results for 

the degradates spirotetrarnat-en01 dimer 1 and spirotetramat-en01 dimer 2 were estimated 

using HPLC methods in supplemental studies. The respective mean values were 

1624 mllgoc and 3208 ml/goc (both are slightly mobile). 
Spirotetramat, at approximately 0.39 lb a.i./A, formulated as an oil dispersion, was 

applied once to four plots (most of which included bareground and planted, total of 7 

trials), located in the USA (FL, CA, NY and WA), dissipated rapidly with calculated 

half-lives of 0.3-1.0 days. These half-lives are consistent with the ones observed in 

laboratory trials. No carryover from year to year is expected for spirotetramat. Due to 

the low storage stability of spirotetramat-enol, which degraded to spirotetramatketohydroxy during storage, individual quantification of these metabolites is not possible. 

Instead, the combined residues of spirotetramat-en01 and spirotetramat-ketohydroxy were 

calculated. Those residues presented calculated half-lives (DTSO,s) of 4.6-3 1.6 days. In 

addition, the combined residues of spirotetramat, spirotetramat-en01 and spirotetramatketohydroxy were found to degrade at moderate rates with half-lives @T50,~) ranging 

from 5.0-23.4 days. Spirotetramat and its residues remained in the top 0-15 cm soil layer, 

except for detections in the 15-30 cm soil layer at the Florida site; the chemicals observed 

above the LOQ in 15-30 cm soil layer were spirotetramat-en01 and spirotetramatketohydroxy at days 1 and 7. The residues went below the LOD and the LOQ by the next 

test interval. 

Since this is a new chemical, there are no monitoring data available. The effects of water 

treatment on the pesticide and degradates is uncertain. Spirotetrarnat and its major 

metabolites, spirotetramat-enol, spirotetramat-ketohydroxy and spirotetramat-MA-amide, 

were highly mobile to moderately mobile, and low levels of binding are expected. It 

appears that spirotetramat metabolites spirotetramat-ketohydroxy and spirotetramat-MAamide are of higher concern because the parent and spirotetramat-en01 degrade relatively 

fast in most environments (particularly in aerobic media). Spirotetramat is not readily 

biodegradable. 

The following tables present physico-chemical and fate data of interest to the Health 

Effects Division (HED). 

Anaerobic soil: 

Hydrolysis (pH 7): 91.8 

Photolysis water: 81.9 

Aerobic waterlsed.: 79.7 / 41.2 
Spirotetramatketohydroxy 

Spirotetramatdi-hydroxy 

Spirotetramatdesmethyl-enol 

Spirotetramat0x0-en01 

CAS: cis-3-(23- 

Dimethylpheny1)-3- 

hydroxy-8- 

methoxy-lazaspiro[4.5]decan2,4-dione 

IUPAC: 2 cis-1 - 

[[(2,5- 

Dimethylpheny1)hydr 

oxyacetyl]amino]-4- 

methoxycyclohexanecarboxylic acid 

IUPAC: (5s,8~)-3- 

(23- 

dimethylpheny1)-3,4- 

dihydroxy-8- 

methoxy-lazaspiro[4.5]decan2-one 

IUPAC: (5s,8~)-3- 

dihydroxy-lazaspiro[4.5]dec-3- 

en-Bone 

IUPAC: 3-(2,5- 

dimethylpheny1)-4- 

hydroxy-lazaspiro[4.5]dec-3- 

ene-2,8-dione 

ierobic soil: 24.0 

Aerobic outdoor: 25.3 

Anaerobic soil: 19.3 

=ield soil: naa 

Soil photolysis: 20.9 

iydrolysis: 

Jhotolysis water: 

4erobic waterlsed.: 17.4 1 42.8 

4erobic soil: 5.2 

4erobic outdoor: 6.2 

4naerobic soil: 7.2 

Field soil: 4.5 

Soil photolysis: 

Hydrolysis: 

Photolysis water: 

Aerobic waterlsed.: 7.8 12.1 

Aerobic soil: . Aerobic outdoor: 

Anaerobic soil: 3.2 

Field soil: 

Soil photolysis: 

Hydrolysis: 

Photolysis water: 

Aerobic waterlsed.: 4.3 15.5 

Aerobic soil: 2.0 

Aerobic outdoor: 

Anaerobic soil: 

Field soil: 

Soil photolysis: 

Hydrolysis: 

Photolysis water: 

Aerobic waterlsed.: - 

Aerobic soil: 

Aerobic outdoor: 

Anaerobic soil: 

Field soil: 

Soil photolysis: 

Hydrolysis: 

Photolysis water: 

Aerobic waterlsed.: 
- . - . . . - . - IUPAC: 2.5- Dlmernyl-DenzO'c Dimethyl-benzoic u 150.18 

acid acid 

CH, 

Spirotetramatglyoxylic amide 

Methoxycyclohexanone 

Methoxycyclohexylaminoc 

arboxylic acid 

Spirotetramat0x0-ketoh ydroxy 

IUPAC: (ls,&)-1- 

w5- 

dimethylphenyl) 

(oxo)acetyl]amino~ 

4- 

methoxycyclohexanecarboxylic acid 

Aerobic outdoor: 3.3 

Anaerobic soil: 

Field soil: 

Soil photolysis: 21 .8b 

Hydrolysis: 

Photolysis water: 

Aerobic waterlsed.: - 

Aerobic soil: 

Aerobic outdoor: 2.3 

Anaerobic soil: 

Field soil: 

Soil photolysis: 4.1 

Hydrolysis: 

Photolysis water: 

Aerobic waterlsed.: - 

IUPAC: 3-(2,5- 

dimethylphenyl)9- 

hydroxy-lazaspiro[4,5]decane 

-2,4,8-trione 

CAS: 4-methoxycyclohexanone 

~hotolisis water: 11.3 

Aerobic waterlsed.: - 

Aerobic soil: c4 0.5 

Aerobic outdoor: 

Anaerobic soil: 

*--CH, 

0 

I FH 

Field soil: 301.35 1 Soil photolysis: 

CAS: 

Cyclohexanecarboxylic acid 

I ~~drol~sis: 

Photolysis water: 

28'17 

Aerobic soil: 

Aerobic outdoor: 

Anaerobic Field soil: soil: 

Soil photolysis: 10.0 

Hydrolysis: 

Photolysis water: 17.5 

Aerobic waterlsed.: - 

Aerobic soil: 

Aerobic outdoor: 

73'21 

Anaerobic soil: 

Field soil: 

Soil photolysis: 

Hydrolysis: 

Spirotetramatphoto-cyclopentyl 

IUPAC: (ls,&)-8'- 

hydroxy-4-methoxy5'-methyl-P'Hspiro[c~clohexane1 ,l '-indeno[l,2- 

clpyrroll-3'(8'H)-one 

299.4 

CH, 

H 

Aerobic waterlsed.: - 

Aerobic soil: 

Aerobic outdoor: 

Anaerobic soil: 

Field soil: 

Soil photolysis: 

Hydrolysis: 

Photolysis water: 42.9' 

Aerobic waterlsed.: - 
IUPAC: ethyl 2- 

[(5~,8~)-8-methoxySpirotetramat- 2-0x0-1- 

photo-2- azaspiro[4.5]dec-3- 373.4 

methylcarbonate en-3-yl]-4- 

methylbenzyl 

carbonate 

IUPAC: (5~,8s)-3-[2- 

Spirotetramat- (h~drox~"'eth~')dphoto-Phydroxy- methylphenyll-8- 301.4 

methoxy-1 - methyl azaspiro[4.5]dec-3- 

en-Pone 

IUPAC: 2-[(5~,8~)-8- 

methoxy-2-0x0-1- 'pirotetramat- -spiro[4.5]dec-3- 299.4 photo-2-formyl ~11-4- 

methylbenzaldehyde 

I I I 

a Not applicable owing to distinct storage instability of spirotetramat-enol (degrading to spirot 

Spirotetramatenol-dimer 2d 

Aerobic outdoor: 

Anaerobic soil: 

Field soil: 

Soil photolysis: 

Hydrolysis: 

Photolysis water: 19.3' 

Aerobic waterlsed.: - 

Aerobic soil: 

Aerobic outdoor: 

Anaerobic soil: 

Field soil: 

Soil photolysis: 

Hydrolysis: 

Photolysis water: 22.9' 

Aerobic waterlsed.: - 

Aerobic soil: 

Aerobic outdoor: 

Anaerobic soil: 

Field soil: 

Soil photolysis: 

Hydrolysis: 

Photolysis water: 11.5' 

Aerobic waterlsed.: - 

Not available 

Aerobic soil: 5.0 

Aerobic outdoor: 1.5 

Anaerobic soil: 7.0 

Field soil: < 0.2 

Soil photolysis: 2.3 

Hydrolysis: 

Photolysis water: 

Aerobic waterlsed.: - 

kfl Aerobic soil: 3.6 

Aerobic outdoor: 0.9 

Anaerobic soil: 4.6 

Field soil: < 0.2 

Photolysis water: 

Soil photolysis: 

Hydrolysis: 

Aerobic waterlsed.: - 

nat-ketohydroxy during frozen 

600 

storage). 

In an outdoor metabolism study, conducted with the formulation on bare soil including natural sunlight, dimethyl-benzoic acid was 

shown not to exceed 3.3 % of AR. 

Photo-rearrangement products produced in sterile buffer solution. 

Possible artifacts owing to hot-spot application in the laboratory; formation under environmental conditions (formulated a.i.) was low. 



Monitoring 

Datamxp 

Concern 

No/No 

No/No 

No/No 

Norno 

NoIYes 

Study Type 

Soil Column Leaching 

Terrestrial Field Dissipation 

Aerobic Soil Metabolism 

Outdoor Metabolism 

Aerob Soil Spirotet-en01 

Anaerobic Soil Metabolism 

Aerobic Aquatic Metabolism 

Soil Column Leaching 

Terrestrial Field Dissipation 

Anaerobic Soil Metabolism 

Aerobic Aquatic Metabolism 

Aerobic Soil Metabolism 

Aerob Soil Spirotet-en01 

Aerobic Soil Metabolism 

Aerob Soil Spirotet-en01 

Aerobic Aquatic Metabolism 

Soil Photolysis (suppl. study) 

Spirotetramat Degradation Products 

% of Applied at Study 

Termination 

11.2 (5 days) 

Not available due to instability 

1.1 (50 d) 

1.0-2.8 (127 d) 

0.1-0.9 (119 d) 

7.2 (180 d, ave of two samples) 

<LOQ (120 d, entire system) 

7.5 (5 days) 

<LOD (120-542 d) 

2.7 (180 d, ave of two samples) 

<LOQ (120 d, entire system) 

1.6-2.3 (50 d, for additnal samples) 

1.0-1.8 (119 d) 

0.4 d (14 d) 

2.3-6.0 (120 d, entire system) 

21.8 (7 d, ave of two samples) 

Table 4. Maximum 

Degradate 

SpirotetramatMA-amide 

Spirotetramatdi-hydroxy 

Spirotetramatdesmethyl-en01 

Spirotetramat0x0-en01 

Dimethyl-benzoic 

MRID or source 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Reported Amounts of 

Maximum % of ~~~likd 

11.2 (5 days) 

Not available due to instability 

6.4 (179 d, ave of two samples) 

6.2 (28 d) 

5.2 (4 d) 

7.2 (180 d, ave of two samples) 

9.2 (60 d, entire system) 

7.5 (5 days) 

4.5 (14 d) 

3.2 (90 d, ave of two samples) 

9.8 (9 1 d, entire system) 

3.8 (179 d, ave two samples) 

2.0 (4 d) 

2.7 (7 d) 

1.1 (observed) 

6.0 (120 d, entire system) 

21.8 (7 d, ave of two samples) 
Monitoring 

Data/Exp 

Concern 

NoINo 

NoIYes 

Nones 

NoINo 

MRID or source 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetrarnat. 

B.8 Fate and 

Behaviou 

' 

Study Type 

Outdoor Metabolism 

Soil Photolysis (suppl. study) 

Outdoor Metabolism 

Aq. Photolysis Natural Water 

Soil Photolysis (suppl, study) 

Aq. Photolysis Natural Water 

Hydrolysis 

 able 4. ~a&mum 

Degradate 

acid 

Spirotetramatglyoxylic amide 

Methox ycyclohexanone 

Methoxycyclohexylaminocarboxylic acid 

Spirotetramat0x0-ketohydroxy 

Reported Amounts of 

Maximum % of Applied 

3.3 (7 d) 

4.1 (2 d, ave of two samples) 

2.3 (7 d) 

17.5 (8 d) 

10.0 (2 d, ave of two samples) 

11.3 (10 d) 

1<0.5 (observed) 

Spirotetramat Degradation products 

% of Applied at Study 

Termination 

0.3-0.5 (127 d) 

1.1-3.4 (7 d, ave of two samples) 

<LOQ (127 d) 

16.0 (10 d) 

6.1 (7 d, ave of two samples) 

11.3 (10 d) 

- - - 
Monitoring 

DataIExp 

Concern 

Noff ossible 

NoIPossible 

NoIPossible 

NoIPossible 

NO/NO~ 

MJUD or source 

OECD 

Monograph 

Annex B. 

Spirotetrarnat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

- 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Table 4. Maximum 

Degradate 

Spirotetramatphoto-cyclopentyl 

Spirotetramatphoto-2- 

methylcarbonate 

Spirotetramatphoto-2-hydroxymethyl 

Spirotetramatphoto-2-formyl 

Spirotetramatenol-dimer 1 

Spirotetramat Degradation Products 

% of Applied at Study 

Terniiitation 

39.2 (7 d, ave two radiolabels; 

35.4-42.9 for individual 

radiolabels) 

17.7 (7 d, ave of two labels) 

14.7 (7 d, ave of two labels) 

5.3 (7 d, ave. of two labels) 

0.0-0.8 (7 d, ave. two samples) 

0.5 (360 d, ave of two samples) 

<LOQ (127 d) 

1.0-3.7 (1 19 d) 

Reported Amounts of 

Maximam % of Applied - 

39.2 (7 d, ave two radiolabels) 

19.3 (6 d, ave of two labels) 

22.9 (6 d, ave of two labels) 

11.5 (3 d, ave. of two labels) 

1.9 (2 d, ave. two samples; 2.3 

for an individual sample) 

12.7 (7 d) 

1.5 (28 d) 

5.0 (60 d) 

' 

Study Type 

Aqueous Photolysis 

Aqueous Photolysis 

Aqueous Photolysis 

Aqueous Photolysis 

-- 

Soil Photolysis (suppl. study) 

Aerobic Soil Metabolism 

Outdoor Metabolism 

Aerob Soil Spirotet-en01 
Table 4. Maximum Reported Amounts of Spirotetramat Degradation Products 

~~~1e~$~~~,o~~@~e~fica17:qnd;d@ate ~i~amete1:s*of~SphO:t;etramat andi~eg'1adati0.n 'Rsod%i(L"~t"s De@cte&b~SubJnitted Environmental Rate -&xidies 

Monitoring 

DatalExp 

Concern 

NO/NO~ 

Major degradates and maximum amounts >lo% are in bold. Unacceptable data were not reported. Refer to Table 1 for chemical names and structures. 

Considered as artifacts owing to hot-spot application in the laboratory, formation under environmental conditions (w. formulated a.i.) was negligible. 

MlUD or source 

Behaviour 

OECD 

Monograph 

Annex B. 

Spirotetramat. 

B.8 Fate and 

Behaviour 

ad- " ' ~od&he@iical agd ~&$&Para~eiers 

Melting point = 142°C 

Boiling point = NA, decomposition at 235OC 

Solubility in organic solvents at 20°C 

Soliient I Solutiility &a) 

Ethanol 44 

- -7.: - k. A, r , 4$ s* ,wade$$): + 

Parent spirotetramat 

IUPAC: cis-3-(2,5- 

dimethylpheny1)-8-methoxy-2- 

0x0- 1 -azaspiro[4.5]dec-3-en-4-y1 

ethyl carbonate 

CAhde,: Carbonic acid, cis-3-(2,5- 

dimethylpheny1)-8-methoxy-2- 

0x0- l-azaspiro[4.5]dec-3-en-4-yl 

ethyl ester 

Study Type 

Anaerobic Soil Metabolism 

Soil Column Leaching 

Terrestrial Field Dissipation 

Aerobic Soil Metabolism 

Outdoor Metabolism 

Aerob Soil Spirotet-en01 

Anaerobic Soil Metabolism 

Soil Column Leaching 

Terrestrial Field Dissipation 

A\ " " T$- ~ stru~tufk?"~ * 

% of Applied at Study 

Termination 

0.3 (180 d, ave of two samples) 

13.7 (5 days) 

0.8 (360 d, ave of two samples) 

<LOQ (127 d) 

1.2-3.3 (1 19 d) 

4.6 (180 d, ave of two samples) 

10.8 (5 days) 

Degradate 

Spirotetramatenol-dimer 2 

Maximum % of Applied 

7.0 (6 d, ave two samples) 

13.7 (5 days) 

<0.2 

9.2 (30 d) 

0.9 (7 d) 

3.6 (14 d) 

4.6 (180 d, ave of two samples) 

10.8 (5 days) 

<0.2 

Dissociation constant pK, = 5.2 

Estimated Koc values from the soil column leaching studv. For 

spirotetramat-en01 from the column experiments: Arithmetic mean Koc 

= 55 Llkg (mobile). 

AdsIDes of transformation product: two SL's, two Sics, and L. No 

definitive test data regarding the adsorption/desorption characteristics 
IUPAC: 2 cis-1-[[(2,5- 

Dimethylphenyl)hydroxyacetyl] 

log Koc obtained by HPLC method: 

IUPAC or CAS name not 

log Koc obtained by HPLC method: 

pH6.0 logKoc =3.49; Koc ~3115 

pH 4, 20°C, ave. of two labels 

Name: Spirotetramat-en01 pH 7,25"C, ave. of two labels 

CAS name: cis-3-(2,5- 

Transformation Product 2: 

Name: Spirotetramatketohydroxy 

labels, entire system) 

99.0 (7 d, ave two 

labels, entire system 

Amount in soil (%) 

10.2 

9.6 

11.6 

17.9 

labels, entire system) 

<LOQ (120 d, ave of 

two labels, entire 

system) 

Amount in leachates (%) 

2.8 

1.3 

2.7 

0.1 

163-1 

NA owing to distinct storage instability of 

spirotetramat-enol, degrading to 

spirotetramat-ketohydroxy during fi-eeze 

storage stability. 

164-1 

161-3 

162-1 

20.9 (2 d, ave 2 

samples) 

14.2 (126 d) 

16.3 (1 d) 

15.0 (1 d) 

14.7 (0.25 d) 

aquatic 

metabolism 

Soil column 

leaching 

12.4-16.7 (7 d, ave two 

samples) 

13.6 (360 d) 

5.9 (50 d) 

5.6 (50 d) 

6.0 (50 d) 

Loamy sand, water pH 7.16 

Totals 5 DAT 

Sandy loam 

Loam 

Silt loam 

FL sandy loam 

The study was conducted with spirotetramat-enol. 

Terrestrial 

field 

dissipation 

Soil 

photolysis 

Aerobic soil 

metabolism 

NY loamy sand 

FL sand 

FL sand; Cropped 

CA sandy loam 

CA SL; Cropped 

WA sandy loam 

WA loamy sand; Cropped 

Supplemental study, useful to identify possible 

photolysates. A fine sandy loam and a loam. 

FL sandy loam 

Sandy loam 

Silt loam 

Silt - 
:AS name: cis-3-(2,s- 

)imethylphenyl)-3-hydroxy-8- 

nethoxy- 1 -azaspiro[4.5]decan- 

!,4-dione 

162-1 Aerobic soil FL sandy loam 

metabolism of Sandy loam 

spirotetramat- Silt loam 

en01 Silt 

Non- Outdoor Loam 

guideline metabolism FL sandy loam 

study 

162-2 Anaerobic Sandy loam 

soil 

metabolism 

162-4 Aerobic Loam, water pH 6.8 

aquatic 

metabolism Loamy sand, water pH 7.16 

19.3 (1 d, ave. two 7.7 (180 d, ave. two 

values, entire values, entire system) 

system) 

40.5 (120 d, ave two 40.5 (120 d, ave two 

labels, entire system) labels, entire system) 

27.5 (60 d, ave two 25.4 (120 d, ave two 

labels, entire system); labels, entire system) 

[50.8 (60 d) for one 

label] 

Amount in soil (%) 

8.4 

3.3 

6.7 

11.0 

Amount in leachates (%) 

2.9 

7.5 

2.0 

0.2 

163-1 Soil column 

leaching 

Totals 5 DAT 

Sandy loam 

Loam 

Silt loam 

FL sandy loam 

The study was conducted with spirotetramat-enol. 
Name: Spirotetramat-MA-amide 

NA owing to distinct storage instability of 

spirotetramat-enol, degrading to 

spirotetramat-ketohydroxy during freeze 

storage stability. 

IUPAC name: 2 cis-1-[[(2,5- 

Dimethylphenyl)hydroxyacetyl] 

amino] -4- 

methoxycyclohexanecarboxylic 

acid 

164-1 

7.2 (180 d, ave. two 

values, entire 

system) 

2.2 (9 d, ave two 

labels, entire system) 

8.7 (60 d, ave two 

labels, entire system) 

9.2 (60 d for one 

6.2 (360 d) 

3.1 (50 d) 

3.3 (50 d) 

1.1 (50 d) 

0.9 (1 19 d) 

0.1 (119 d) 

0.2 (1 19 d) 

0.1 (90 d) 

2.8 (128 d) 

1.0 (128 d) 

7.2 (180 d, ave. two 

values, entire system) 

162-1 

162-1 

Nonguideline 

study 

162-2 

<LOQ (120 d, ave two 

labels, entire system) 

1.0 (120 d, ave two 

labels, entire system) 

Terrestrial 

field 

dissipation 

Aerobic soil 

metabolism 

Aerobic soil 

metabolism of 

spirotetramaten01 

Outdoor 

metabolism 

162-4 

NY loamy sand 

FL sand 

FL sand; Cropped 

CA sandy loam 

CA SL; Cropped 

WA sandy loam 

WA loamy sand; Cropped 

FL sandy loam 

Sandy loam 

Silt loam 

Silt 

FL sandy loam 

Sandy loam 

Silt loam 

Silt 

Loam 

FL sandy loam 

Anaerobic 

soil 

metabolism 

Aerobic 

Sandy loam 

Loam, water pH 6.8 

aquatic 

metabolism Loamy sand, water pH 7.16 

IUPAC name: (5s,8s)-3-(2,5- 

dimethylpheny1)-3,4-dihydroxy-8- 

methoxy- 1 -azaspiro[4.5]decan-2- 

Transformation Product 5: 

Name: Spirotetramat-desmethyl-. 
Transformation Product 6: 

Name: Spirotetramat-0x0-en01 

IUPAC name: 3-(2,5- 

dimethylpheny1)-4-hydroxy-1- 

azaspiro[4.5]dec-3-ene-2,8-dione 



Yame: Spirotetramat-oxocetohydroxy 

[UPAC name: 3-(2,5- 

1imethylphenyl)-3-hydroxy- 1 - 

tzaspir0[4,5]decane-2,4,8-trione 
Transformation Product 12: 

Name: Spirotetramat-photoIUPAC name: (1~~4s)-8'- 

hydroxy-4-methoxy-5'-methyl2'H-spiro[cyclohexane-l , 1'- 

indeno[l,2-clpyrroll-3'(8'H)-one 
Transformation Product 13: 

Name: Spirotetramat-photo-2- 

methylcarbonate 

IUPAC name: ethyl 2-[(5sY8s)- 

8-methoxy-2-oxo-lazaspiro[4.5]dec-3-en-3-y1]-4- 

methylbenzyl carbonate 

18.3 (6 d, ave two 

labels); 19.3 (6 d for 

one radiolabel) 

17.7 (7 d, ave two 

labels) 

Aqueous 

photolysis at 

pH 5 

rest temperature: 25OC. 



0.9 (7 d) 0.3 (63 d) Non- Outdoor -f"I 0.9 (7 d) <LOQ (127 d) guideline metabolism ."-. <- study 

4.6 (180 d) 4.7 (1 80 d) 162-2 Anaerobic 

soil 

PU metabolism 

2(-2H) 

Amount in soil ('33) Amount in leachates (%) 163-1 Soil column 

4.8 NA leaching 

5.9 NA 

6.1 NA 

10.8 NA 

164-1 Terrestrial 

field 

dissipation 

-- 

NA = Not analyzed. 

Loam 

FL sandy loam 

Sandy loam 

Totals 5 DAT 

Sandy loam 

Loam 

Silt loam 

FL sandy loam 

The study was conducted with spirotetramat-enol. 

NY loamy sand 

FL sand 

1 FL sand; Cropped I CA sandy loam 

CA SL; Cropped 

WA sandy loam 

ND = Not detected. 

Major degradates and maximum amounts 110% are in bold. Unacceptable data were not reported.