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Adverse
Effects
Abstracts
ACTIVITY:
Insecticide
(oxadiazine)
CAS Name:
methyl (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-
(trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate
EPA,
as of June 9, 2004, Indoxacarb:
(S)-methyl 7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]
amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate
EPA, as of June 9, 2004,R-enantimomer:
(R)-methyl 7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]
carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate
Structure
of Indoxacarb:
Adverse
Effects:
Anemia
Ataxia
Blood
Body
Weight Decrease
Bone
Brain
CNS
Cytotoxic
Developmental
Endocrine: Thymus
Heart
Kidney
Liver
Lung
Spleen
Tremors
|
Environmental
Effects:
Moderately
to Very High Toxic to freshwater and estuarine/marine fish
and invertebrates
Risks to Bees: High Toxicities via contact routes
|
Regulatory
Information
(only comprehensive for the US) |
US
EPA Registered: |
Yes |
US
EPA PC Code: |
067710 |
California
Chemical Code |
5331 |
US
Tolerances: |
CFR
180.564 |
Registered
use in
(includes only a limited list of countries)
|
Australia, India, New Zealand,
US
Africa:
Burkina Faso, Cameroon, Cape Verde, Chad, Gambia, Guinea-Bissau,
Mali, Mauritania, Niger, Senegal, South Africa, Taiwan,
Tanzania |
US
Maximum Residue Levels permitted
in food commodities
|
Indoxacarb
and
its R-enantimomer are
permitted in or on 67 food commodities,
including:
Apple, Brassica, Cattle, Corn,
Cotton gin byproducts,
Cotton, undelinted seed,
Goat, Hog, Horse,
Lettuce (head & leaf),
Milk, Milk fat, Pear, Sheep,
Vegetables (fruiting group)
Experimental Use Permit:
Cherry (sweet & tart) to
May 2007
Peaches from May 2003 to May
2006
Time-limited
tolerances:
Collards to June 2006
Cranberry to Dec 2007 |
Other
Information |
Molecular
Formula: |
C22H17Cl
F3 N3O7 |
Manufacturers: |
DuPont |
Other
Names: |
Indoxycarb
Avaunt
Steward
DPX-MP062
352-EUP-166
DPX-KN128 |
Manufacture
site: |
US:
DuPont, Alabama 36505
Asturias,
Spain |
Of
special interest: |
PAN
Data |
Material
Safety Data Sheets and labels. |
June
8, 2005 - Multi-national giant DuPont
is planning to enter India's infrastructure industry in a
big way besides expanding its agriculture seed and coating
and colour technologies business in the country, its chief
executive said on Wednesday. "India has been our traditional
base where we have been trying to enter the coating technology
market in a big way. Now, the infrastructure sector was opening
up and we would also be keen to register our presence,"
DuPont chairman and chief executive officer Chad Holliday
told PTI Nagoya, Japan.... Later briefing visiting reporters,
Holliday said DuPont's market in China was around $1 billion.
Referring to the company's achievements in the agricultural
seed sector, Holliday recalled that Indian
farmers were amazed at the results on utilising Indoxcarb,
a branded cotton insecticide. "Similarly in Argentina
we helped farmers fight Asian Soyabean Rust, a devastating
new disease with our best-in-class fungicide Flusilazole,"
company vice-president Uma Chowdhry told PTI. Powell said
the company earned 42 per cent of its revenue from USA, 28
per cent from Europe and 17 per cent from Asia.
Ref: DuPont eyes India's core sector; by Priyadarshi Siddhanta
in Nagoya | June 08. rediff.com
June
9, 2005 - Production in Gujarat. India, Mr Holliday, said,
presented a huge market in agriculture protection and insecticides.
In particular, the chemical insecticide (Indoxacarb)
for cotton sold under the brand name DuPont Avaunt has
done exceedingly well. The company has
a production centre at Savli in Gujarat where it has two units
for some other crop protection products. In the same
area, DuPont has one for liquid packaging systems and for
its `Refinish' blending facility.
Ref: DuPont goes where the market is, says CEO by Ashok Dasgupta,
The
Hindu. |
July
18, 2002 -
Opinion of the Scientific
Committee on Plants on specific questions
from the Commission concerning the evaluation of Indoxacarb.
European Commission. Health & Consumer Protection Directorate-General. |
Sept
17, 2004 - Updated
Summary of Toxicology Data, California EPA |
March
11, 1999 - Summary
of Toxicology Data - Indoxycarb. California
EPA Department of Pesticide Regulation, Medical Toxicology Branch. |
October
30, 2000 - Pesticide
Fact Sheet. US EPA |
March
21, 2002 - Registration
approval of Avaunt Insecticide in New York State.
|
March
5, 2001 - Australia:
Amendment to the MRL standard: Allows
20 mg/kg in dry apple pomace for animal feed. Also, change for
asparagus. |
Abstracts |
August
2001 -
IR-4: New
Products/Transitional Solution List - This
list contains brief descriptions of numerous new pest control
materials that have been introduced over the last several years.
Additionally, it contains information on some "older"
crop protection chemicals that are believed to have room for
new uses. This List includes:
Indoxacarb |
October
2001 - Glossary
of Pesticide Chemials. A listing of
pesticides subject to analysis of residues in foods and feeds
by the US Food and Drug Administration. |
Insecticide
products - partial list |
Metabolites
and other names for Indoxacarb |
Metabolite |
CAS
No. |
Scientific
Name(s) |
USEPA
/OPP PC Code: |
R-
enantiomer |
173584-44-6 |
[(R)-methyl
7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4- (trifluoromethoxy)
phenyl] amino] carbonyl] indeno [1,2-e]
[1,3,4]oxadiazine-4a(3H)-carboxylate] |
067710 |
DPX-MP062
(Steward¨30%WG) |
173584-44-6 |
75:25
mixture of Indoxacarb
and its R-enantiomer |
- |
DPX-KN
128 |
173584-44-6 |
Indoxacarb
METHYL 7-CHLORO-2,5-DIHYDRO-2-
{{(METHOXYCARBONYL){4-
(TRIFLUOROMETHOXY)PHENYL}AMINO}
CARBONYL}-
INDENO{1,2-E}{1,3,4}OXADIAZINE-4A(3H)-
CARBOXYLATE
California
Index Name:
INDENO{1,2-E}{1,3,4}OXADIAZINE-4A(3H)-
CARBOXYLIC ACID, 7-CHLORO-2,5-
DIHYDRO-2-{{(METHOXYCARBONYL){4-
(TRIFLUOROMETHOXY)PHENYL}AMINO}
CARBONYL}-, METHYL ESTER, (S)- (9CI) |
067710 |
DPX-JW062
(Steward¨30%WG) |
- |
Contains
50% Indoxacarb
- Ref: DuPont MSDS |
- |
IN-MK638 |
82971-90-2 |
UREA,
[4-(TRIFLUOROMETHOXY)PHENYL]
- (CAS NAME)
(METABOLITE OF INDOXACARB) |
667710 |
IN-MK643
|
None
available as of April 2003 |
DIHYDRO-5-(TRIFLUOROMETHOXY)-2H-
BENZIMIDAZOL-2-ONE
(METABOLITE OFINDOXACARB) |
667711 |
US
Federal Register
••
Note: Due to length, the following is a partial
list. Click here
to see full list of FR entries.
|
Published
Date |
Docket
Identification Number |
Details |
July 11, 2007 |
EPA-HQ-OPP-2005-0149 |
E.I. du Pont de
Nemours and Company and IR4.
Pesticide
tolerance. FINAL RULE.
Tolerances are established for the combined
residues of the insecticide indoxacarb and its R-enantiomer,
(R)- methyl 7-chloro-2,5-dihydro-2[[(methoxycarbonyl)[4(trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4][oxadiazine-4a(3H)-carboxylate,
in or on the following raw agricultural commodities:
DOCUMENTS AVAILABLE WITH
THIS FINAL RULE: |
NOF: Indoxacarb in/on cucurbit vegetable
group 9, stone fruit, and cranberry
Docket: EPA-HQ-OPP-2005-0149-0003 |
Indoxacarb. Health Effects Division (HED)
Risk Assessment for Grapes; Vegetable, Brassica, Leafy,
Group 5; Turnip Greens; Vegetable, Leafy, Except Brassica
(Group 4); Pome Fruits (Group 11, except pear); Tuberous
and Corm Vegetables (Subgroup 1C); Cucurbit Vegetables
(Group 9); Stone Fruits (Group 12); Cranberry; Mint; Okra;
Southern Pea; and Fire Ant Bait.
Docket: EPA-HQ-OPP-2005-0149-0005 |
Indoxacarb: Acute and Chronic Dietary
Exposure and Risk Assessments for the Proposed Section
3 Registrations and Petitions for Tolerances on Grapes;
Vegetable, Brassica, Leafy, Group 5; ...; Pome Fruits
(Group 11, except pear); Tuberous and Corm Vegetables
(Subgroup 1C); Cucurbit Vegetables (Group 9); Stone Fruits
(Group 12); Cranberry; Mint; Okra; and Southern Pea.
Docket: EPA-HQ-OPP-2005-0149-0006 |
Indoxacarb. Petitions for Tolerances
on Vegetable, Leafy, Except Brassica (Group 4), Pome Fruits
(Group 11, except pear), Tuberous
Docket: EPA-HQ-OPP-2005-0149-0007 |
Commodity |
Parts
per million |
Apple, wet pomace |
3.0 |
Alfalfa, forage |
10 |
Alfalfa, hay |
50 |
Cattle, fat |
1.5 |
Cattle, meat |
0.05 |
Cattle, meat byproducts |
0.03 |
Corn, sweet, forage
|
10 |
Corn, sweet, kernel plus cob with husk
removed |
0.02 |
Corn, sweet, stover |
15 |
Cotton, gin byproducts |
15 |
Cotton, undelinted seed |
2.0 |
Cranberry |
0.90 |
Fruit, pome, except pear, group
11
This group includes
10 commodities.
apple • apple, dried pomace • apple, juice
• apple, wet pomace • crabapple •
fruit, pome • loquat • mayhaw •
pear • pear, oriental • quince
|
1.0 |
Fruit, stone, group
12
This group includes
14 commodities.
apricot • cherry, sweet • cherry, tart
• fruit, stone • fruit, stone, except
plum, prune, dried • nectarine • peach
• plum • plum, chickasaw • plum,
damson • plum, japanese • plum, prune
• plum, prune, dried • plum, prune, fresh
|
0.90 |
Goat, fat |
1.5 |
Goat, meat |
0.05 |
Goat, meat byproducts |
0.03 |
Grape |
2.0 |
Grape, raisin |
5.0 |
Hog, fat |
1.5 |
Hog, meat |
0.05 |
Hog, meat byproducts |
0.03 |
Horse, fat |
1.5 |
Horse, meat |
0.05 |
Horse, meat byproducts |
0.03 |
Milk |
0.15 |
Milk, fat |
4.0 |
Okra |
0.50 |
Pea, southern, seed |
0.10 |
Peanut |
0.01 |
Peanut, hay |
40 |
Pear |
0.20 |
Pear, oriental |
0.20 |
Peppermint, tops |
11 |
Sheep, fat |
1.5 |
Sheep, meat |
0.05 |
Sheep, meat byproducts |
0.03 |
Soybean, aspirated grain fractions |
45 |
Soybean, hulls |
4.0 |
Soybean, seed |
0.80 |
Spearmint, tops |
11 |
Turnip, greens |
12 |
Vegetable, Brassica, leafy, group
5
This group includes
16 commodities.
broccoli • broccoli raab
• broccoli, chinese • brussels sprouts
• cabbage • cabbage, chinese, bok choy
• cabbage, chinese, mustard • cabbage,
chinese, napa • cauliflower • collards
• kale • kohlrabi • mustard greens
• mustard spinach • rape greens •
vegetable, brassica, leafy, group
|
12 |
Vegetable, cucurbit, group
9
This group includes
19 commodities.
balsam apple • balsam pear • cantaloupe
• chayote, fruit • cucumber • cucumber,
chinese • cucurbits • gherkin, west indian
• gourd, edible • melon • melon,
citron • muskmelon • pumpkin • squash
• squash, summer • squash, winter •
vegetable, cucurbit, group • watermelon •
waxgourd, chinese
|
0.60 |
Vegetable, fruiting, group
8
This group includes
17 commodities.
chili, postharvest • eggplant • groundcherry
• pepino • pepper • pepper, bell
• pepper, nonbell • pepper, nonbell, sweet
• tomatillo • tomato • tomato, concentrated
products • tomato, dried pomace • tomato,
paste • tomato, puree • tomato, wet pomace
• vegetable, fruiting • vegetable, fruiting,
group
|
0.50 |
Vegetable, leafy, except Brassica,
group 4
This group includes
37 commodities.
amaranth, leafy • arugula • cardoon •
celery • celery, chinese • celtuce •
chervil • chervil, fresh leaves • chrysanthemum,
edible leaved • chrysanthemum, garland •
corn salad • cress, garden • cress, upland
• dandelion, leaves • dock • endive
• fennel, florence • fennel, florence,
fresh leaves and stalk • kale, sea • lettuce,
head • lettuce, leaf • orach • orach,
leaves • parsley • parsley, leaves •
purslane, garden • purslane, winter •
radicchio • rhubarb • spinach •
spinach, chinese • spinach, new zealand •
spinach, vine • swiss chard • tampala
• vegetable, leafy • vegetable, leafy,
except brassica, group
|
14 |
Vegetable, tuberous and corm, subgroup
1-C
This subgroup includes
22 commodities.
arracacha • arrowroot • artichoke, chinese
• artichoke, jerusalem • canna, edible
• cassava • chayote root • chufa
• dasheen • ginger • leren •
potato • potato culls • potato granules
flakes • potato peel, wet • potato processed
potato waste • potato, specialty • sweet
potato • tanier • turmeric • yam
bean • yam, true
|
0.01 |
|
April 12, 2006 |
EPA-HQ-OPP-2005-0149 |
IR-4.
Pesticide
petition: PP 5E6991 for Indoxacarb and its R-enantiomer
-- vegetable, cucurbit, group 9
at 0.5 ppm
This group includes 19 commodities.
balsam apple • balsam pear • cantaloupe •
chayote, fruit • cucumber • cucumber, chinese
• cucurbits • gherkin, west indian • gourd,
edible • melon • melon, citron • muskmelon
• pumpkin • squash • squash, summer •
squash, winter • vegetable, cucurbit, group •
watermelon • waxgourd, chinese
-- fruit, stone, group
12 at 1.0 ppm
This group includes 14 commodities.
apricot • cherry, sweet • cherry, tart •
fruit, stone • fruit, stone, except plum, prune, dried
• nectarine • peach • plum • plum,
chickasaw • plum, damson • plum, japanese •
plum, prune • plum, prune, dried • plum, prune,
fresh
-- cranberry at 1.0 ppm. |
August
31, 2005 |
OPP-2005-0223 |
Pesticide
Emergency Exemptions:
•
Massachusetts. EPA authorized the use
of indoxacarb on cranberry to
control cranberry weevil; May 12, 2005 to June 30, 2005. Contact:
(Stacey Groce) |
June
30, 2005 |
OPP-2005-0149 |
IR-4
& DuPont.
Pesticide Petition
for Indoxacarb and its R-enantiomer; in or on the following
raw agricultural commodities:
Pesticide
Petition |
Commodity |
PPM |
PP
5E6911 |
leafy
greens, except spinach, subgroup
4A
This
subgroup includes 24 commodities.
amaranth, grain • arugula • chervil •
chrysanthemum, edible leaved • chrysanthemum,
garland • corn salad • cress, garden •
cress, upland • dandelion • dock •
endive • lettuce • lettuce, head •
lettuce, leaf • orach • parsley •
purslane, garden • purslane, winter • radicchio
• spinach • spinach, chinese • spinach,
new zealand • spinach, vine • tampala |
10 |
PP
5E6911 |
spinach
|
3 |
PP
5E6911 |
leafy
petioles subgroup
4B
This
subgroup includes 8 commodities:
amaranth, leafy • cardoon • celery •
celery, chinese • celtuce • fennel, florence
• rhubarb • swiss chard |
1.5
|
PP
5E6911 |
fruit, pome, except pear, group
11
This
group includes 14 commodities:
pricot • cherry, sweet •
cherry, tart • fruit, stone • fruit, stone,
except plum, prune, dried • nectarine •
peach • plum • plum, chickasaw • plum,
damson • plum, japanese • plum, prune •
plum, prune, dried • plum, prune, fresh |
1.0 |
PP
5E6911 |
vegetable,
tuberous and corm, subgroup
1C
This
subgroup includes 22 commodities:
arracacha • arrowroot • artichoke, chinese
• artichoke, jerusalem • canna, edible •
cassava • chayote root • chufa • dasheen
• ginger • leren • potato •
potato culls • potato granules flakes •
potato peel, wet • potato processed potato waste
• potato, specialty • sweet potato •
tanier • turmeric • yam bean • yam,
true |
0.01 |
PP
5E6911 |
okra |
0.5
|
PP
5E6929 |
pea,
southern |
0.1 |
PP
5E6929 |
peppermint,
tops |
10 |
PP
5E6929 |
spearmint,
tops |
10 |
Residue
Chemistry. The
active ingredient in the end-use formulation,
DuPont\TM\ Avaunt[reg] insecticide, is a 75:25 mixture of
two isomers, indoxacarb (DPX-KN128) and IN-KN127. Only one
of the isomers, indoxacarb (DPX-KN128), has insecticidal activity.
Since the insecticidal efficacy is based on the concentration
of indoxacarb (DPX-KN128), the application rates have been
normalized on an indoxacarb (DPX-KN128) basis. The
proposed tolerance expression includes both indoxacarb (DPX-KN128)
and IN-KN127, and the residue method does not distinguish
between the enantiomers. Therefore, residues are reported
as the sum of indoxacarb
(DPX-KN128) combined with IN-KN127. Residues of indoxacarb
(DPX-KN128) combined with IN-KN127 will be referred to as
KN128/KN127.
Acute
neurotoxicity study.
•
In an acute neurotoxicity study, indoxacarb exhibited
decreased forelimb grip strength, decreased foot splay, and
some evidence of slightly reduced motor activity, but only
at the highest doses tested. The no
observed adverse effect level (NOAEL) was 100
milligrams/kilogram (mg/kg) for males, and
12.5 mg/kg for females,
based on body weight effects in females 50 mg/kg.
Reproductive
and developmental toxicity.
• In
a 2-generation rat reproduction study, the parental NOAEL
was 1.5 mg/kg/day. The parental NOAEL was based on observations
of reduced weight gain and food
consumption for the higher concentration groups of the F 0
generation and potential treatment-related
changes in spleen weights for the higher groups of
the F 1 generation.
•
The NOAEL for fertility and reproduction was 6.4 mg/kg/day.
The offspring NOAEL was 1.5 mg/kg/day, and was based on the
reduced mean pup weights noted
for the F 1 litters of the higher concentration groups.
•
Developmental studies conducted in rats and rabbits demonstrated
that the rat was more susceptible than
the rabbit to the maternal and fetal effects of DPX-
MP062.
•
The NOAEL for maternal and fetal effects
in rats was 2 mg/kg/day based on body
weight effects and decreased food consumption at 4
mg/kg/day.
•
The
NOAEL for developmental effects in fetuses was >4 mg/kg/day.
In rabbits, the maternal and fetal NOAELS were 500 mg/kg/day
based on body weight effects,
decreased food consumption in dams and decreased
weight and delayed ossification in fetuses at 1,000
mg/kg/day.
Chronic
toxicity.
•
The
chronic
NOAEL
in male rats was 5 mg/kg/day based on body
weight and nutritional effects. In
females, the NOAEL of 2.1 mg/kg/day was based
on body weight and nutritional changes, as well as biologically
significant hematologic changes at 3.6 mg/kg/day and above.
Hemolytic effects were present only through the 6-month evaluation
and only in females.
•
In
mice,
the chronic NOAEL of 2.6 mg/kg/day for males was based on
deceased body weight and weight gain effects and food efficiency
at 13.8 mg/kg/day and above. The NOAEL for females was 4.0
mg/kg/day based on body weight nutritional effects, neurotoxicity,
and clinical signs at 20 mg/kg/day. In dogs, the chronic NOAEL
was about 2.3 and 2.4 mg/kg/day in males and females, respectively
based on hemolytic effects similar to those seen in the subchronic
dog study.
Subchronic
toxicity.
•
Mice
were less sensitive to indoxacarb than the rats or dogs.
NOAELs (23 mg/kg/day, males, 16 mg/kg/day,
females) were based on mortality
(males only); increased reticulocytes and
Heinz bodies and decreased body weight, weight gain, food
consumption, food efficiency; and increased clinical signs
(leaning to one side and/or with abnormal gait or mobility)
(females only).
In a 28-day repeated dose dermal study, the NOAEL was 50 mg/kg/day
based on decreased body weights, body weight
gains, food consumption, and food efficiency in
females, and changes in hematology parameters,
the spleen and clinical signs of toxicity in both sexes in
rats. |
••
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