Agrow New Generics 2015 - 2020
Chapter 1
1. Introduction
1.1 Summary
Agrow’s New Generics 2015 - 2020 is a guide to herbicide, fungicide and insecticide active ingredients
coming off-patent (key patents covering the active ingredient per se, i.e. composition of matter) over the
period between 2015 and 2020.
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The report comprises profiles covering 7 herbicides, 15 fungicides and 5 insecticides.
A brief background to patents and data protection is given.
The information to be found in the active ingredient profiles is described.
1.2 Introduction
1.2.1
Active ingredients
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Agrow’s New Generics 2015 - 2020 is a guide to herbicide, fungicide and insecticide active ingredients
coming off-patent (key patents covering the active ingredient per se, i.e. composition of matter) over the
period between 2015 and 2020.
Active ingredients have been included if:


They have been allocated ISO common names.
At least one of the patents of composition of matter granted under the Patent Cooperation Treaty,
by the United States Patent and Trademark Office or by the European Patent Office are due to
expire in this period.
The report comprises profiles covering 7 herbicides, 15 fungicides and 5 insecticides.
1.2.2
Duration of patent and data protection
The expiry dates of the identified patents are noted in the active ingredient profiles and in the summary
tables at the beginning of the chapters covering herbicides, fungicides and insecticides. These are the
dates 20 years on from the filing dates of the relevant same or related patents.
In recent years, intellectual property offices have recognised that agrochemical (“plant protection products”)
and pharmaceutical active ingredient inventions cannot be exploited commercially until regulatory approval
has been obtained and that this can be a lengthy process. As a result, in compensation, special forms of
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Chapter 2
Agrow New Generics 2015 - 2020
2. Herbicides
2.1 Summary
This chapter includes profiles of herbicide active ingredients with composition of matter patents expiring
over the period 2015 – 2020.
The herbicides covered are flufenpyr-ethyl, foramsulfuron, metamifop, oxaziclomefone, penoxsulam,
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pinoxaden and topramezone.
2.2 Introduction
Each profile starts with a concise statement on the active ingredient as a crop protection product, its
chemical structure and official chemical nomenclature. The active ingredients included in this chapter are
listed along with some key details in Table 2.2.1.
Table 2.2.1. Major herbicide active ingredients with patents expiring 2015 – 2020
PCT/EU patent
US patent expiry
EU
US
ingredient
expiry date
date
Registration?
Registration?
Flufenpyr-ethyl
19 February 2018
No
Yes
Foramsulfuron
12 April 2015
25 February 2019
Yes
Yes
Metamifop
24 July 1999
24 July 1999
No
No
Oxaziclomefone
4 December 2016
4 December 2016
No
No
Penoxsulam
23 September 2017
23 September 2017
Yes
Yes
Pinoxaden
11 March 2019
11 March 2019
Yes*
Yes
Topramezone
29 October 2018
29 October 2018
Yes*
Yes
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Active
* Pending at EU level; national Member State authorisations
The next section covers formulation: significant and recent products that have been placed on the market,
based on the active ingredient alone or significant mixtures, and their compositions
Key physico-chemical properties relevant to formulating the active ingredient are listed. The material safety
data sheet (MSDS) of an example product is highlighted.
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Chapter 2
2.6.1
Agrow New Generics 2015 - 2020
Formulation
Oxaziclomefone has been developed in a large number of mixture products.
Some more recent
formulations are shown in Table 2.6.1. These include products from a number of different companies.
Table 2.6.1. Oxaziclomefone formulations
Company
Brand
Composition and comments
Hokko Chemical
A-one
Oxaziclomefone + tefuryltrione
Naginata Jumbo,
Oxaziclomefone + pyrimisulfan + benzobicyclon
Industry
Kumiai
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Naginata Mametsubu
Kumiai
Zantetsu Mametsubu
Oxaziclomefone + pyrimisulfan
Nissan
Sirius Exa
oxaziclomefone+pyraclonil+pyrazosulfuronethyl+benzobicyclon
Source: Agrow
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Physico-chemical properties related to formulation:
Melting point: 149.5oC
Log P (log Kow): 4.01 at pH 7, 20oC
Water solubility: 0.18 mg/L at 20oC
Vapour pressure: 1.33 x 10-
02
mPa at 25oC
Source: University of Hertfordshire Pesticide Properties Database
2.6.2
Patents
Major patents covering the intellectual property around oxaziclomefone are listed in Table 2.6.2.
Table 2.6.2. Key patents covering oxaziclomefone
Patent type
Patent claims
PCT/EU patent
US patent number
number and expiry
and expiry date
date
Composition
1,3-oxazin-4-one derivatives as herbicides
WO9721688
US6046135
4 December 2016
4 December 2016
of matter
Source: European Patent Office
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Chapter 2
2.9.2
Agrow New Generics 2015 - 2020
Patents
Major patents covering the intellectual property around topramezone are listed in Table 2.9.2.
Table 2.9.2. Key patents covering topramezone
Patent type
Composition
Patent claims
Novel benzoylpyrazole compounds
Process
Method and novel intermediate products for
producing isoxazolin-3-yl-acylbenzenes
Source: European Patent Office
2.9.3
Use
Activity and application:
US patent
number and
number and
expiry date
expiry date
WO9923094
US6147031
29 October 2018
29 October 2018
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of matter
PCT/EU patent
WO0029394
US6469176
12 November 2019
12 November 2019
Topramezone is a post-emergence herbicide controlling BLW and certain
grasses in maize, turf and ornamentals. Key weeds include the BLW wild mustard (Sinapis arvensis),
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volunteer canola (oilseed rape) and the grass weeds (Echinochloa crus-galli) and green foxtail (Setaria
viridis). It is intended for use with a mixture partner or as part of a weed control programme, e.g. with
atrazine or tritosulfuron + dicamba. BASF has recommended the addition of the proprietary adjuvant Dash
in the US.
More details can be found on the product label of which an example (AMVAC’s Impact) can be found here
Crops: Maize, turf, ornamentals
Targets:
Amaranthus palmeri, Mollugo verticillata, Xanthium strumarium, Datura stramonium, Kochia
scoparia, Chenopodium album, Hibiscus trionum, Ipomoea spp., Chorispora spp., Sinapis spp., Solanum
nigrum, Solanum ptycanthum, Amaranthus blitoides, Amaranthus retroflexus, Amaranthus hybridus,
Amaranthus albus, Ambrosia artemisiifolia, Ambrosia trifida, Sida spinosa, Polygonum persicaria,
Polygonum pensylvanicum, Helianthus annuus, Cirsium arvense, Abutilon theophrasti, Amaranthus rudis,
Amaranthus tuberculatos, Echinochloa oryzicola, Digitaria sanguinalis, Setaria faberi, Setaria viridis, Setaria
glauca, Galium aparine, Sorghum halepense, Panicum miliaceum, Panicum dichotomiflorum, Brachiaria
platyphylla
Mode of action and resistance: Topramezone’s mode of action is to inhibit HPPD (HRAC category F2),
the same as other families of herbicide chemistry including triketones, isoxazoles and pyrazoles.
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Chapter 3
Agrow New Generics 2015 - 2020
Material safety datasheet:
An example (Cosine, UK) can be found here
3.5.2
Patents
Major patents covering the intellectual property around cyflufenamid are listed in Table 3.5.2.
These
include European and US patents covering the molecule itself and its manufacture.
Table 3.5.2. Key patents covering cyflufenamid
Patent type
Patent claims
PCT/EU patent
US patent number
number and
and expiry date
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expiry date
Composition
Benzamidoxime derivative, process for
of matter
production thereof and agrohorticultural
bacericide
Others
Agricultural/horticultural fungicidal
compositions
US5847005
18 December 2015
18 December 2015
WO9746097
US6156796
3 June 2017
3 June 2017
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Source: European Patent Office
WO9619442
3.5.3
Use
Activity and application: Cyflufenamid provides protective and curative control of powdery mildew. It
comes from the amidoxime class of fungicides and has a mode of action that has yet to be defined. It is
active against all strains of powdery mildew, including those resistant to demethylation inhibitors,
strobilurins and benzimidazoles.
Cyflufenamid as Cosine is recommended for use at 0.5 L/ha (maximum 2 applications) on apples and pears
in the UK. The pre-harvest interval is 28 days. The same formulation is sold as Cyflamid for use on
cereals. The 5% oil-in-water emulsion is active against strains of disease, which are resistant to other
commonly used fungicides such as strobilurins, demethylation inhibitors, and benzimidazoles.
Cyflufenamid will usually be tank-mixed with broad-spectrum fungicides. Protectant applications are likely
to be effective at 0.25 L/ha or less, and good curative activity may be achieved from 0.5 L/ha.
Cyflufenamid is reported to have vapour and translaminar activity that contribute to its overall efficacy.
Cyflufenamid (as NF-149) has demonstrated good control of powdery mildew on grape clusters in field trials
in the USA, but only moderate effects on foliage. A lower rate of 1.8 oz/acre was just as effective as 3.6
oz/acre.
More details can be found on the product label of which an example (Cosine, UK) can be found here
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Chapter 3
Agrow New Generics 2015 - 2020
Table 3.9.1. Key patents covering flumorph
Patent type
Patent claims
PCT/EU patent
US patent number
number and
and expiry date
expiry date
Composition of
Fluorine-containing diphenyl acrylamide
matter
antimicrobial agents
3.9.3
US 6020332
9 Feb 2018
Use
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Activity and application: Flumorph is a systemic carboxylic acid amide (CAA) fungicide whose chemical
structure closely resembles that of dimethomorph. It is systemic, with protectant, curative and antisporulant
activity.
Flumorph is used for the control of oomycete diseases such as cucumber downy mildew
(Pseudoperonospora cubensis), brassica downy mildew (Peronospora parasitica), grape downy mildew
(Plasmopara viticola) and tomato late blight (Phytophthora infestans).
Some resistance has been reported in Phytophthora capsici, P. infestans and Pseudoperonospora
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cubensis; as well as cross-resistance with other CAA fungicides such as dimethomorph and iprovalicarb.
Crops: Cucumber, lychee, melon, pepper, potato, tomato, vegetables, grapevines
Targets: Oomycete fungi, Peronospora parasitica, Phytophthora infestans, Plasmopara viticola,
Pseudoperonospora cubensis
Mode of action and resistance: Flumorph’s mode of action is to inhibit cellulose biosynthesis and cell wall
deposition
(FRAC
target
site
H5,
code
40:
CAA-fungicides).
This
group
includes
other
valinamide carbamates (iprovalicarb), cinnamic acid amides (dimethomorph, flumorph) and mandelic acid
amides (mandipropamid). Risk of resistance is known in Plasmopora viticola, but not in Phytophthora
infestans and the risk is estimated as low to medium. A resistance management strategy is required.
3.9.4
Registrations and markets
EU registration
Flumorph is not registered in the EU.
US registration
Flumorph is not registered in the US.
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Chapter 3
Agrow New Generics 2015 - 2020
3.13.1 Formulation
Metrafenone’s main commercial formulations are shown in Table 3.13.1. Key physico-chemical properties
relating to formulation and an example of an MSDS can be found below.
Table 3.13.1. Representative commercial formulations of metrafenone
Company
Brand
Composition and comments
BASF
Attenzo, Flexity
Metrafenone 300 g/l SC (UK, Netherlands)
BASF
Vivando
Metrafenone 500 g/l SC (Australia, Chile, France,
BASF
Vivando
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Germany)
Metrafenone 300 g/l SC (US)
Source: Agrow and company websites
Mixtures have been developed with fenpropimorph (Ceando) and with fenpropimorph plus epiconazole
(Capalo) for use on cereals. The addition of metrafenone and fenpropimorph to epoxiconazole provides
additional control of eyespot, mildew and septoria while protecting the triazole chemistry against resistance.
Physico-chemical properties related to formulation
Log P (log Kow): 4.3 at pH 7, 20oC
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Melting point: 100oC
Water solubility: 0.492 mg/L at 20oC
Vapour pressure: 1.53 x 10-
01
mPa at 25oC
Source: University of Hertfordshire Pesticide Properties Database
Material safety datasheet:
An example (Attenzo, Flexity) can be found here
3.13.2 Patents
Major patents covering the intellectual property around metrafenone are listed in Table 3.13.2,
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Chapter 3
Agrow New Generics 2015 - 2020
Material safety datasheet:
An example (Headline, US) can be found here
3.17.2 Patents
Major patents covering the intellectual property around pyraclostrobin are listed in Table 3.17.2. These
include European and US patents covering the molecule itself and its manufacture.
Table 3.17.2. Key patents covering pyraclostrobin
Patent claims
PCT/EU patent
number and
expiry date
Composition
2-[(dihydro)pyrazolyl-3′-oxymethyl]anilides,
of matter
their preparation and their use
Source: European Patent Office
3.17.3 Use
Activity and application:
US patent number
and expiry date
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Patent type
WO9601256
US5869517
21 June 2015
21 June 2015
Pyraclostrobin is a broad-spectrum fungicide with protective, curative,
eradicative, translaminar and locosystemic properties. The active ingredient itself is branded as F500. It is
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taken up rapidly by the plant and is largely retained by the waxes in the leaf cuticle. It demonstrates good
translaminar movement through the leaf, resulting in disease control on both leaf surfaces by inhibiting
spore germination and mycelium development. Acropetal and basipetal transport in leaves and vapour
phase activity is very limited.
After a curative or, against some diseases, an eradicative treatment, mycelium development is inhibited.
Pyraclostrobin is also reported to have beneficial effects on plant growth and yield and these are attributed
to enhanced nitrate reductase activity leading to improved nitrogen assimilation during the stages of rapid
crop growth (GS 31 - 39) and decreased ethylene production resulting in delayed senescence.
Dose rates are in the range 50 – 500 g/ha
More details can be found on the product label of which an example (Headline, US) can be found here
A large number of two-way and three-way pre-mix formulations have been developed. Mixture partners
include: boscalid, epoxiconazole, folpet, fenpropimorph, fipronil, kresoxim-methyl, mancozeb and
triticonazole.
BASF received US approval (October 2014) for the fungicide, Xanthion, for in-furrow use on maize.
Xanthion comprises pyraclostrobin and the former Becker Underwood biofungicide, Integral (Bacillus
subtilis strain MBI 600). BASF acquired Becker Underwood in late 2012. Xanthion controls soil-borne
diseases and BASF claim that it provides improved cold tolerance and promotes seedling growth.
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Chapter 4
Agrow New Generics 2015 - 2020
Physico-chemical properties related to formulation:
Melting point: -54oC
Log P (log Kow): 5.03 at pH 7, 20oC
Water solubility: 0.67 mg/L at 20oC
Vapour pressure: 1.8 mPa at 25oC
Source: University of Hertfordshire Pesticide Properties Database
4.5.2
Patents
Major patents covering the intellectual property around metofluthrin are listed in Table 4.5.2.
Patent type
Patent claims
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Table 4.5.2. Key patents covering metofluthrin
Composition
Esters of 2,2-dimethyl-
of matter
cyclopropanecarboxylic acid
Source: European Patent Office
4.5.3
Use
PCT/EU patent number
US patent number
and expiry date
and expiry date
EP0939073
US6225495
24 February 2019
24 February 2019
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Activity and application: Metofluthrin is a pyrethroid insecticide and repellant sold into household,
personal protection and animal health markets.
Further information about an example product and its use (Off! Clip-on Mosquito Repellent, US) can be
found here
Crops: Not applicable
Targets: Spodoptera litura, Tineola biselliella, Diptera, Musca domestica, Coleoptera, Thysanoptera,
Blatella germanica, Aphis gossypii, Culex pipiens palleus
Mode of action and resistance: Metofluthrin is a sodium channel modulator (IRAC group 3).
4.5.4
Registrations and markets
EU registration
Metofluthrin is not registered in the European Union.
US registration
Metofluthrin is registered in the US and is currently in the EPA’s registration review process.
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