Use of spinosynes as soil insecticides

Details Use of spinosynes as soil insecticides Use of spinosynes as soil insecticides

2000-11-17

2003-06-24

Pryor, Alton (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S209000

Reexamination Certificate

active

06583088

ABSTRACT:

This Application is a 371 of PCT/EP99/03318 filed May 14, 1999.
The present invention relates to the use of spinosyns, in particular for treating the soil, for treating seed or plant propagation material, and for drenching and irrigating plants.
It is known that spinosyns can be used for controlling insects (WO 97/00 265, WO 93/09 126, WO 94/20 518, U.S. Pat. No. 5,362,634).
It has now been found that spinosyns have systemic properties and that application via the soil or via plant irrigation is possible. They may also be used for treating seed and plant propagation material.
The spinosyns are known compounds. The fermentation product described in U.S. Pat. No. 5,362,634 (A 83543) is composed of a variety of compounds termed Spinosyn A, B, C and the like (cf. WO 97/00 265, WO 93/09 126 and WO 94/20 518). The spinosyns may be represented by the following formulae (I) and (II):
(I)

Compound
R
1′
R
2′
R
3′
R
4′
R
5′
R
6′
R
7′
Spinosyn A
H
CH
3
C
2
H
5
CH
3
CH
3
CH
3

Spinosyn B
H
CH
3
C
2
H
5
CH
3
CH
3
CH
3

Spinosyn C
H
CH
3
C
2
H
5
CH
3
CH
3
CH
3

Spinosyn D
CH
3
CH
3
C
2
H
5
CH
3
CH
3
CH
3

Spinosyn E
H
CH
3
CH
3
CH
3
CH
3
CH
3

Spinosyn F
H
H
C
2
H
5
CH
3
CH
3
CH
3

Spinosyn G
H
CH
3
C
2
H
5
CH
3
CH
3
CH
3

Spinosyn H
H
CH
3
C
2
H
5
H
CH
3
CH
3

Spinosyn J
H
CH
3
C
2
H
5
CH
3
H
CH
3

Spinosyn K
H
CH
3
C
2
H
5
CH
3
CH
3
H

Spinosyn L
CH
3
CH
3
C
2
H
5
CH
3
H
CH
3

Spinosyn M
H
CH
3
C
2
H
5
CH
3
H
CH
3

Spinosyn N
CH
3
CH
3
C
2
H
5
CH
3
H
CH
3

Spinosyn O
CH
3
CH
3
C
2
H
5
CH
3
CH
3
H

Spinosyn P
H
CH
3
C
2
H
5
CH
3
H
H

Spinosyn Q
CH
3
CH
3
C
2
H
5
H
CH
3
CH
3

Spinosyn R
H
CH
3
C
2
H
5
H
CH
3
CH
3

Spinosyn S
H
CH
3
CH
3
H
CH
3
CH
3

Spinosyn T
H
CH
3
C
2
H
5
H
H
CH
3

Spinosyn U
H
CH
3
C
2
H
5
H
CH
3
H

Spinosyn V
CH
3
CH
3
C
2
H
5
H
CH
3
H

Spinosyn W
CH
3
CH
3
C
2
H
5
CH
3
H
H

Spinosyn Y
H
CH
3
C
2
H
5
CH
3
CH
3
H

Spinosyn A 17-Psa
H
CH
3
H
C
2
H
5
CH
3
CH
3
CH
3
Spinosyn D 17-Psa
CH
3
CH
3
H
C
2
H
5
CH
3
CH
3
CH
3
Spinosyn E 17-Psa
H
CH
3
H
C
2
H
5
CH
3
CH
3
CH
3
Spinosyn F 17-Psa
H
H
H
C
2
H
5
CH
3
CH
3
CH
3
Spinosyn H 17-Psa
H
CH
3
H
C
2
H
5
H
CH
3
CH
3
Spinosyn J 17-Psa
H
CH
3
H
C
2
H
5
CH
3
H
CH
3
Spinosyn L 17-Psa
CH
3
CH
3
H
C
2
H
5
CH
3
H
CH
3
and
(II)

Compound
R
1′
R
2′
R
3′
R
4′
R
5′
Spinosyn A 9-Psa
H
CH
3
C
2
H
5
H

Spinosyn D 9-Psa
CH
3
CH
3
C
2
H
5
H

Spinosyn A aglycone
H
CH
3
H
C
2
H
5
H
Spinosyn D aglycone
CH
3
CH
3
H
C
2
H
5
H
There have also been disclosed semisynthetic spinosyns of the formula (Ia)
(WO 97/00 265) in which
A and B each represent a single bond, a double bond or an epoxide unit,
R represents
R
1
represents hydrogen or methyl,
R
2
, R
3
and R
4
independently of one another represent C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkylcarbonyl or protected hydroxyl,
R
5
represents hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkylamino or represents alkylhydroxylamino of the formula
 in which
R
10
and R
11
independently of one another represent hydrogen, C
1
-C
4
-alkyl or C
1
-C
5
-alkylcarbonyl,
R
6
represents hydrogen or methyl,
R
7
, R
8
and R
8′
independently of one another represent C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl or C
1
-C
4
-alkylcarbonyl, or represent protected amino, and
R
9
represents methyl or ethyl.
The term “spinosyn” as used herein encompasses the compounds disclosed in WO 97/00 265.
Individual spinosyns, but also mixtures of the abovementioned spinosyns of the formulae (I), (Ia) and (II) may be used according to the invention.
Mixtures comprising at least one spinosyn of the formula (I) or (II) are preferably used.
Mixtures comprising a mixture of spinosyn A and spinosyn D in which the ratio of spinosin A to spinosyn D is generally between approximately 80:20 and approximately 98:2, a value of approximately 85:15 being preferred, are preferably used. Spinosad (see, for example, DowElanco trade magazine Down to Earth, Vol. 52, No. 1, 1997 and the literature cited therein), which comprises essentially a mixture of spinosyn A and spinosyn D in a ratio of approximately 85:15, is especially preferably used.
In particular, the fermentation product A 83543, which comprises approximately 85 to 90% of spinosyn A, approximately 10 to 15% of spinosyn D and minor amounts of spinosyns B, C, E, F, G, H and J and which is disclosed in U.S. Pat. No. 5,362,634, is used.
The acid addition salts described therein may also be used.
The following types of seed and plant propagation material are preferably treated according to the invention:
Maize, cereals (such as, for example, wheat, barley, oats, rye), rice, seed potatoes, cotton, oilseed rape, sunflower, beet (such as, for example, sugar beet), vegetable seed (such as, for example, onion, cabbage, tomato), (fodder) legumes, peanuts, soya, sorghum.
The following general treatment methods are preferably suitable for carrying out the seed treatment, or plant propagation material treatment, according to the invention:
dry treatments (preferably with addition of adhesion promoters such as, for example, liquid paraffin or talc), and, if appropriate, colorants,
slurry treatments (preferably with addition of wetters, dispersants, emulsifiers, adhesives, inert fillers and colorants),
aqueous liquid treatments (preferably with addition of emulsifiers, dispersants, thickeners, antifreeze agents, polymers, adhesives and colorants),
solvent-based liquid treatments (with addition of solvents and colorants), emulsion treatments (with addition of emulsifiers, solvents and colorants).
The total active compound content in the spinosyn treatment formulations preferably amounts to 10 to 80% by weight.
Preferably, 1 to 300 g of active compound are applied to every 100 kg of seed or plant propagation material in the form of a treatment.
The treatment method according to the invention is carried out in customary treatment apparatuses or drum mixers as are customary, for example, in the construction industry.
Seed (or plant propagation material) and seed treatment formulation (or treatment formulation for plant propagation material) are mixed intimately in a conventionally used treatment apparatus.
After the seed (or plant propagation material) has been treated, it is dried to a sufficient degree in the case of the wet treatments, and the resulting treated seed (or plant propagation material) is then packaged in portions.
When applying the seed or plant propagation material which has been treated according to the invention, 1 to 5000 kg of treated seed (or plant propagation material) are generally employed per hectare of area under cultivation, preferably 100 to 300 kg of seed (or plant propagation material) per hectare of area under cultivation.
Surprisingly, it has been found that the spinosyns have systemic properties and, when applied via the soil, are very effective against the animal pests mentioned further below.
It is advantageous to apply granules comprising the active compound(s) into or onto the soil. Examples of suitable applications are broadcast, band, furrow and planting-hole application. Broadcast application is to be understood as superficial application of the active compound over the entire area to be treated and subsequent mechanical incorporation into the soil.
The use in seed boxes in rice cultivation may be mentioned especially (nursery box treatment).
It is particularly advantageous to emulsify or dissolve the spinosyns or their salts in water and to use this for irrigating the plants.
Examples of suitable applications are spraying onto the soil, drenching, i.e. irrigating the plants with active-compound-containing solutions, and drip irrigation, and also use in hydroponic systems, in particular in the production of vegetables and ornamentals.
The spinosyns may also be applied via the stem, for example by means of stem injection.
The seed treatments according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which are found in agriculture and in forests. They are effective agains

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