CN112040774A - Use of tetramic acid derivatives for reducing nematode populations - Google Patents
Use of tetramic acid derivatives for reducing nematode populations Download PDFInfo
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- CN112040774A CN112040774A CN201980025627.3A CN201980025627A CN112040774A CN 112040774 A CN112040774 A CN 112040774A CN 201980025627 A CN201980025627 A CN 201980025627A CN 112040774 A CN112040774 A CN 112040774A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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Abstract
The invention relates to the use of tetramic acid derivatives of formula (I) for reducing the population of nematodes living in the soil after treatment of the soil.
Description
The invention relates to the use of tetramic acid derivatives of formula (I) for reducing the population of soil-dwelling (soil-dwelling) nematodes after soil treatment. The compounds of formula (I) are known from WO 2006/089633. WO 2006/089633 describes its use for controlling animal pests. Mixtures of compounds of formula (I) with other insecticides and/or acaricides are also known, for example from WO 2009/039951. It is also known to control nematodes by specific tetramic acid derivatives after foliar treatment (WO 2009/085176).
It has now been found that the compounds of formula (I) are suitable for reducing soil-dwelling nematode populations after soil application,
wherein
W and Y are independently hydrogen, C1-C4-alkyl, chloro, bromo, iodo or fluoro,
x is C1-C4Alkyl radical, C1-C4-alkoxy, chlorine, bromine or iodine,
d is hydrogen or a methyl group,
A. b together with the carbon atom to which they are attached is saturated C3-C6-cycloalkyl, wherein one ring member is optionally replaced by nitrogen, and which is optionally substituted by C1-C4-alkoxy is monosubstituted, or
A. B together with the carbon atom to which they are attached is C substituted by alkylenedioxy3-C6-cycloalkyl, said alkylenedioxy group being optionally substituted by C1-C4-alkyl or C1-C4-alkoxy-C1-C2-alkyl is substituted and forms, together with the carbon atom to which it is attached, a five-or six-membered ketal,
g is hydrogen (a) or one of the following groups
Wherein
E is a metal ion or an ammonium ion,
m is oxygen or sulfur, and M is oxygen or sulfur,
R1is straight chain or branched C1-C6-an alkyl group,
R2is straight chain or branched C1-C6-an alkyl group.
Preference is given to active ingredient combinations comprising compounds of the formula (I) in which the radicals are defined as follows:
w is preferably a methyl group, and W is preferably a methyl group,
x is preferably chlorine or methyl (especially methyl),
y is preferably chlorine, bromine or methyl,
d is preferably hydrogen, and is preferably hydrogen,
A. b and the carbon atom to which they are attached are preferably saturated C6Cycloalkyl substituted with an alkylenedioxy group which, together with the carbon atom to which it is attached, forms a five-or six-membered ketal,
g is preferably hydrogen (a) or one of the following radicals
Wherein
M is oxygen, and M is oxygen,
e is a monovalent metal ion or ammonium ion (especially sodium or potassium),
R1preferably straight or branched C1-C4-an alkyl group,
R2preferably straight or branched C1-C4-an alkyl group.
Particular preference is given to compounds of the formula (I) in which G ═ hydrogen.
Very particular preference is given to active ingredient combinations comprising compounds of the formula (I) in which the radicals are defined as follows:
method and use
The invention also relates to a method for reducing a population of soil-dwelling nematodes, wherein a compound of formula (I) is allowed to act on the population of soil-dwelling nematodes and/or its habitat. Preferably reducing soil-dwelling nematode populations in agriculture and forestry.
In view of good plant tolerance and favourable toxicity to warm-blooded animals as well as good environmental tolerance, the active ingredients of formula (I) according to the invention are suitable for protecting plants and plant organs against biotic and abiotic stress factors, thereby increasing harvest yields, improving the quality of the harvested material, and controlling soil-dwelling nematode populations encountered in agriculture, horticulture, forestry and garden and leisure facilities.
The compounds of formula (I) according to the invention can preferably be used for controlling soil-dwelling nematode populations. They are active against normally sensitive and resistant species and against all or specific developmental stages. The above nematodes include:
plant pests from the phylum nematoda, i.e. plant parasitic nematodes, in particular the wild Tritylenchus species (Aglenchus spp.) such as the farmer wild Tritylenchus (Aglenchusa), Ditylenchus species (Anguina spp.) such as the wheat grain nematode (Anguina tritici), the Aphelenchus species (Aphelenchus spp.) such as the peanut leaf nematode (Aphelenchus arachidis), the strawberry leaf nematode (Aphelenchus fragaria), the nematodiella species (Belnolalexus spp.) such as the nematode fines (Belnolales gracilis), the Gilles longus (Bellululus longicaudatus), the Nodosa (Bellulus persicus), the Trichophyllus species (Burserpens), the Trichophyllus spp.) such as the nematode (Burserpens), the Trichophyllus spp (Burserpens), the Trichophyton species (Burserpens), the Trichophyton sp.), the Trichophyton species (Burserpens), the species (Burserpigeonia spp.) such as the nematode (Burserpens), the nematode (Burserpigeonia spp (Burserpens), the species (Burserpens), the nematode (Burkellus spp.) such as the species (Burserpens), the species (Burserpigeonia spp (Burserpens), the species (Burserpigeonia spp.) such as the species (Burserpens), the species (Burserpigeon, Cyclotylenchus scripta (Criconemella onansis), Cyclotylenchus decorus (Criconemella ornata), Cyclotylenchus malformation (Criconemella ruscus), Cyclotylenchus gracilis (Criconema xenoplax), Cyclotylenchus species (Criconema filiforme), e.g. Cyclotylenchus floridum (Criconema ferriensis), Cyclotylenchus fragrans (Criconema filiformis), Cotylenchus striatus (Criconema pallidus), Cotylenchus rougherius (Criconema pallidus), Cotylenchus rougheri (Criconema pallidus), Cotylenchus bifidus (Ditylenchus bifidus), e.g. Heterophyllorum (Heterophyllocrea), Cotylenchus striatus species (Heterophyllorula), Cotylenchus striatus sp (Heterophyllorus), Cotylenchus striatus (Heterochaetocerorum sp), e.g. Spodopterocarpus (Heterochaetocerorum), Cotylenchus fasciatus (Heterochaetocerorum), Cochloa (Heterochaetocerorum), Cochlamygda), Cochlamycolza (Hexoplasma spp), Cochloa (Hexoplasma sp) Soybean cyst nematodes (Heterodera glycines), beet cyst nematodes (Heterodera schachtii), rhizophilus spp (Hirschmaniella spp.), neodesmodium spp (hopolaimus spp.), strongyloides spp (longido spp.) (e.g. longus spp.) (longus africanus), Meloidogyne spp (Meloidogyne spp.) (e.g. Meloidogyne gilvus (Meloidogyne chinensi.), pseudomeloidogyne pseudochinensis (Meloidogyne fallax), Meloidogyne hapla (Meloidogyne hapla), Meloidogyne incognita (Meloidogyne incognita), Meloidogyne tenus (Meloidogyne spp.) (Meloidogyne incognita), Meloidogyne tenus (Meloidogyne cuneata), Meloidogyne species, phyllodera (parynia), Meloidogyne tenus spp. (paranoid, pseudolepta), Meloidogyne tenus spp (paradendron spp.) (parakeratoides spp.) (species), Meloidogyne spp (parakeratoides spp.) (parakeratoides spp.) (species), pseudoleptia spp (parakeratoides spp.))) Species of the genus Pseudohalenchus, species of the genus Leptodermus (Psilenchus spp.), species of the genus Sphaeria (Punctodera spp.), species of the genus Strobilanthus (Quinisulcus spp.), species of the genus Rapholitus (Rapholus spp.), species of the genus Rapholitus (Rapholitus spp.) (e.g., Scleroderma citri (Raptophlus), Scleroderma cinerea (Rapholitus similis)), species of the genus Nepholitus (Rotylenchulus spp.), species of the genus Sphaerothecium (Rotychus spp.), the species pelteobagrus (brullema spp.), the species nematodiasis (subangunya spp.), the species trichoderma (trichoderma spp.), such as the blunt-bristled nematode (trichoderma obliquus), the original-bristled nematode (trichoderma primaticus), the species tylenchus (tylenchus spp.), such as the dwarf type of circled nematode (tylenchus lanuginosus), the species nematodiasis (tylenchus spp.), such as the dwarf type of nematode (tylenchus lanuginosus), the species nematodiasis (tylenchus spp.), the nematode (tylenchus spp.), the species of nematodiasis (tylenchus semipennyx (e), and the species of nematodiasis (xipholus spp.) (e.g. such as the marker xiphotylenchus spp.).
Nematode (nematode)
In the context of the present invention, the term "nematodes" includes all species of the phylum nematoda, and in this context in particular as parasites on plants (e.g. species of the order aphelencholia (Aphelenchida), meloidogyne, tylenchus (Tylenchida) and other species).
The expression "reducing the nematode population" means preventing or making more difficult their development or growth, thereby reducing the infection pressure.
Herein, the efficacy of a compound is determined by the following method: the number of nematode eggs per unit soil volume and/or the mortality rate per unit soil volume, gall formation, cyst formation and/or nematode density per root and/or nematode motility is compared between plants or plant parts or treated soils with the compounds of the formula (I) according to the invention and untreated plants, plant parts or untreated soils (100%). Preferably, a reduction of 20 to 50%, particularly preferably of 51 to 79% and very particularly preferably a substantially complete prevention of development and growth of the nematode population by a reduction of 80 to 100% is achieved relative to untreated plants, plant parts or untreated soil. Reduction of nematode populations as described herein also includes reduction of nematode reproduction (development of galls, cysts and/or eggs).
The person skilled in the art is aware of methods for determining mortality, gall formation, cyst formation, nematode density per soil volume, nematode density per root, number of nematode eggs per soil volume, motility of nematodes.
Use of the compounds of formula (I) can keep plants healthier and also include reduction of nematode damage and increase of harvest yield.
In the context of the present invention, the term "nematode" refers to plant nematodes, which include all nematodes that damage plants. Plant nematodes include plant parasitic nematodes and soil-dwelling nematodes. Plant parasitic nematodes include ectoparasites, such as the species nematodiasis (xiphilinema spp.), the species nematodiasis (Longidorus spp.), and the species nematodiasis (Trichodorus spp.); hemiparasites, such as the species nematodiella hemipenetrans (Tylenchulus spp.); migratory endoparasites, such as the species Pratylenchus spp, the species Radopholus spp and the species scutellariae ema spp; non-migratory parasites such as species of the genus Heterodera (Heterodera spp.), the species of the genus Heterodera globosa (Globodera spp.), and the species of Meloidogyne (Meloidogyne spp.); and endoparasites of stems and leaves, such as the species diptera (Ditylenchus spp.), the species Aphelenchoides (Aphelenchoides spp.) and the species Heterodera (Hirschmaniella spp.). Particularly harmful soil nematodes parasitic on roots are, for example, cyst-forming nematodes of the genus Heterodera or Heterodera globiformis, and/or root-gall nematodes of the genus Meloidogyne. Harmful species of these genera are, for example, Meloidogyne incognita (Meloidogyne incognita), Heterodera glycines (Heterodera glycines) (soybean cyst nematode), potamophoides tuberosa (Globodera pallida), and potamonocarpus solani (Globodera roserachis) (yellow potamotosus globulosa), which are effectively controlled by the compounds described herein. However, the use of the compounds described herein is in no way limited to these genera or species, but extends in the same way to other nematodes.
Plant nematodes include, for example, the agro-wild-type root-knot nematode (Aglenchus agricola); wheat grain nematode (Anguina tritici); peanut root-knot nematodes (Aphelenchoides arachidis), strawberry root-knot nematodes (Aphelenchoides fragariae), and endoparasitic species of the stem and leaves (Aphelenchoides spp.); thoraco parvus (Belolaimis gracilis), thoraco praecox longus (Belolaimis longicaudatus), thoraco nortonia (Belolaimis nortoni); cocos nucifera (Bursaphelenchus coccophilus), Aphelenchus similis (Bursaphelenchus ereus), Bursaphelenchus xylophilus (Bursaphelenchus xylophilus) and Aphelenchus species (Bursaphelenchus spp.); harmful necrotic nematodes (Cacopaurus pestis); the nematodes of the curvata sinuses (cricetonella convvata), the orbicularis scripta elegans (cricetonella onoensis), the orbicularis decora (cricetonella ornata), the orbicularis malformation (cricetonella ruscum), the orbicularis gracilis (cricetonella xenoplax) (═ ring-rot nematodes (mesocricetonema xenoplax)) and the species strongyloides (cricetonella spp.),
tricycloid fungi of the genus Tricycloid (Cryonemobides ferriae), Tricycloid fungi (Cryonemobides onoense), Tricycloid fungi (Cryonemobides ornatum), and Tricycloid species (Cryonemobides spp.); rot stem nematode (Ditylenchus destructor), Ditylenchus dipperscus (Ditylenchus dipsaci), Trichostylenchus nematus (Ditylenchus myceliophagus), and endoparasitic species of stems and leaves (Ditylenchus spp.); heterodera sinensis (Dolichorus heterocephamus); white potato nematode (Globodera pallida) (═ potato cyst nematode (Heterodera pallida)), potato nematode (Globodera rostochiensis) (yellow potato cyst nematode), Heterodera solani (Globodera solanacearum), tobacco cyst nematode (Globodera tabacum), glogyria virginiana (Globodera virginii) and non-migratory cyst-forming parasite species of the species Heterodera parasitica (Globodera p.); bicontinuous helical nematodes (helicopterus chrysoticus), bicontinuous helical nematodes (helicoptera), dicorotrichum erythraeum (helicopterus erythraeum), pleomorphic helical nematodes (helicopterus multicinctus), hemipleus spirochetus (helicopterus nannus), hemipleus giganteus (helicopterus pseudomonius), and spirochetus species (helicopterus spp.); hemicyclonematode (hemicericolides); coleoptera cochinchinensis (heterocladia artemia), heterocladia numata (heterocladia parvana), heterocladia avenae (Heterodera avenae), heterocladia brassicae (heteroclada cruifera), heterocladia sojae (heteroclada glycines) (soyama bean cytodermoides), heterocladia oryzae (heteroclada oryzae), heterocladia betanae (heteroclada schactiii), heteroclada zeae (heteroclada zeae), and the non-migratory cyst-forming species of parasite species (heteroclada spp.); latent root nematodes (Hirschmaniella gracilis), latent root nematodes (Hirschmaniella oryzae) of rice, helminthic nematode (Hirschmaniella spinosa) and endoparasitic latent root nematode species of stems and leaves (Hirschmaniella spp.); nematodes of the Egyptian (Hoplolimus aegyptii), Caninium (Hoplolimus californicus), Columbia (Hoplolimus columbus), Cap (Hoplolimus galeatus), Anethopathia (Hoplolimus indicus), Anethorum (Hoplolimus indicus), Dactyla magnus (Hoplolimus), pseudoxyna (Hoplolimus parastulus), Angora africana (Longidorus africanus), Longidosus (Longidorus brevianum), Longidosus (Longidorus elongatus), Longidosus (Longidorus elongtus), Longidobearing nematode (Longidorus longissimus), and Extrinoblongus species (Loplophora sp); root-knot nematodes (Meloidogyne acriae), African root-knot nematodes (Meloidogyne africana), peanut root-knot nematodes (Meloidogyne arenaria), Meloidogyne arenaria (Meloidogyne thraustaria), Meloidogyne cayensis, Meloidogyne saccharina (Meloidogyne erecta), Meloidogyne chianus (Meloidogyne chinewoodchuck), Meloidogyne coffei (Meloidogyne cofeicla), Meloidogyne setosum (Meloidogyne thiopica), Meloidogyne parvum (Meloidogyne exigua), Meloidogyne lobata (Meloidogyne fallax), Meloidogyne graminis (Meloidogyne graminea), Meloidogyne graminea (Meloidogyne graminea), meloidogyne gramineae (Meloidogyne graminis), Meloidogyne hapla, Meloidogyne incognita (Meloidogyne hapla), Meloidogyne incognita (Meloidogyne incognita), Meloidogyne javanica (Meloidogyne javania), Meloidogyne gemmifera (Meloidogyne kikugyensis), Meloidogyne minor (Meloidogyne minor), Meloidogyne hapla (Meloidogyne naasi), Meloidogyne balanopsis (Meloidogyne paraensis), Meloidogyne hapla (Meloidogyne paraensis), Meloidogyne tha (Meloidogyne thasias), Meloidogyne thapsis (Meloidogyne thamsis), and species of non-migratory nematodes (Meloidogyne spep.); coccinella species (Meloinema spp.), Heterocladus nematodes (Nacobber aborans), Neotylenchus virussi, Erythroculter pseudochinensis (Paraphelenchus pseudolaris), Bursaphelenchus pseudochinensis (Paralichororus allius), Bursaphelenchus pseudochinensis (Paralichororus auriculatus), Bursaphelenchus parvus (Paralichororus lobaus), Bursaphelenchus parvus (Paralichororus subulatus), Bursaphelenchus brevicaulis (Paralichororus porosus), Bursaphelenchus callosum (Paralichororus porosus), Bursaphelenchus glabreus (Paralichororus teres) and Bursaphelodermacopeus spp.; hookworm (species hamatus), nonsmozzling (species minutus), epididymis (species), and nematodiasis (species spp.); brevibacterium agilis (Pratylenchus agilis), Brevibacterium ehreni (Pratylenchus alleni), Brevibacterium andersum (Pratylenchus andins), Brevibacterium divaricatum (Pratylenchus brachyurus), Brevibacterium cerealis (Pratylenchus cerealis), Brevibacterium coffeensis (Pratylenchus coeffeae), Brevibacterium nickelatus (Pratylenchus crenatus), Brevibacterium germanica (Pratylenchus delatteri), Brevibacterium colubricola (Pratylenchus gibbicatatus), Brevibacterium gulus gigantis (Pratylenchus giganticola), Brevibacterium gulus giganteus (Pratylenchus goodyli), Brevibacterium gracilium (Pratylenchus gracilis), pratylenchus hexaensis (Pratylenchus hexius), Pratylenchus brasiliensis (Pratylenchus loxsi), Pratylenchus elongatus (Pratylenchus neglicus), Pratylenchus penetrans (Pratylenchus penetans), Pratylenchus pratensis (Pratylenchus pratensis), Pratylenchus brasiliensis (Pratylenchus scriber), Pratylenchus terus (Pratylenchus terus), Pratylenchus somnus (Pratylenchus thornei), Pratylenchus destructor (Pratylenchus vulus vus), Pratylenchus maydis (Pratylenchus zeae), and promyelochus immaturus species (Pratylenchus spp); pseudohalenichus minutus, large-tooth smooth-edged nematode (Psilenchus magnens), swollen smooth-edged nematode (Psilenchus tubidus), chalco-dermal nematode (puncotora chalcoensis), fifth-furrow nematode (quisulcus acutus), citrus nematode (radius citrophilus), nematode (radius similis), and migratory endoparasite of the genus nematode (radius spp.); northern reniform nematodes (Rotylenchulus borealis), tiny reniform nematodes (Rotylenchulus parvus), reniform rotifers (Rotylenchulus reniformis) and reniform nematode species (Rotylenchulus spp.); helicotylenchus (Rotylenchus laurentinus), cysticercus magnus (Rotylenchus macroodoratus), strongylius robustus (Rotylenchus robustus), strongylius simplex (Rotylenchus uniformis), and strongylius species (Rotylenchus spp.); caudad nematode (Scutellonema brachyurum), scoutello nematode (Scutellonema brachyss), caudad nematode (Scutellonema cladheraudum), and migratory endoparasitic scutellariae species (Scutellonema spp.); root gall nematodes (Subanguina radiata), tabacum tenuiana (tetylenchoceanica), drum burr nematodes (tricholorus cylindricus), micro burr nematodes (tricholorus minor), primitive burr nematodes (tricholorus primativus), neighboring burr nematodes (tricholorus proximitis), similar burr nematodes (tricholorus similis), rare burr nematodes (tricholorus spissus) and ectoparasite burr species (tricholorus spp.); farmland dwarf nematodes (Tylenchus agri), vegetable dwarf nematodes (Tylenchus brassicae), clear dwarf nematodes (Tylenchus clarus), Kleinden dwarf nematodes (Tylenchus claytoni), finger dwarf nematodes (Tylenchus digitatus), British dwarf nematodes (Tylenchus ebriensis), maximum dwarf nematodes (Tylenchus maximums), naked dwarf nematodes (Tylenchus nulus), common dwarf nematodes (Tylenchus vulgaris) and dwarf species (Tylenchus spp.); meloidogyne citrulli (Tylenchulus semiependerans) and the hemiparasitic species xylaria gracilis (Tylenchulus spp.); canaryworms (xiphilia americanum), brevicola (xiphilia brevicola), secatella (xiphilia dimorphicaudate), tagetes (xiphilia index), and ectoparasite sword nematode species (xiphilia spp.).
Nematode populations that may be reduced using the compounds of formula (I) of the present invention include: nematodes of the genus Meloidogyne (Meloidogyne), such as Southern root-knot nematode (Meloidogyne incognita), javanica root-knot nematode (javanica), Northern root-knot nematode (Meloidogyne hapla) and peanut root-knot nematode (Meloidogyne arenaria); nematodes of the genus diptychus (Ditylenchus), such as the potato rot nematode (putrescence stem nematode) and the stem and bulb nematodes (stem and bulb wolform) (xylem dipsacia aspera (Ditylenchus dipsaci)); nematodes of the genus Pratylenchus (Pratylenchus), such as corn root-rot-division nematodes (cobra nematodes) (Pratylenchus penrans), chrysanthemum root-rot nematodes (chrysanthus root-division nematodes) (Pratylenchus fallax), coffee root-rot nematodes (coffeeroot-rot nematodes) (Pratylenchus coffees), tea root-rot nematodes (tea root-rot nematodes) (Pratylenchus roseus) and walnut root-rot nematodes (walnut root-rot nematode) (Pratylenchus pratylus); nematodes of the genus Heterodera globiformis (Globodera), such as yellow potato cyst nematode (Potato Anoectochilus roxburghii) and white potato cyst nematode (white potato cyst nematode) (Globodera pallida); nematodes of the genus Heterodera (Heterodera), such as soybean cyst nematode (Heterodera glycines) and beet cyst nematode (Heterodera betacellum) (Heterodera schachtii); nematodes of the genus Aphelenchoides (Aphelenchoides), such as rice white-tip nematodes (Aphelenchoides besseyi), Chrysanthemum nemum nematoda (Aphelenchoides ritzemabosi) and strawberry nematodes (strawberry nematoda) (Aphelenchoides strawberry nematode); nematodes of the genus euglena (Aphelenchus), such as the herbivorous nematodes (fungivorous nematoda) (Aphelenchus avenae)); nematodes of the genus nematoda (Radopholus), such as burrowing nematodes (like Radopholus similis); nematodes of the genus heminematoda (tylnchulus), such as the citrus root nematodes (citrus heminematoda); nematodes of the genus reniform (Rotylenchulus), such as reniformis (reniformis), reniformis (Rotylenchulus reniformis); tree-dwelling nematodes such as pine wood nematode (Bursaphelenchus xylophilus) and red ring nematode (Cocos nucifera) and the like.
Plants which can be protected using the compounds of formula (I) according to the invention include the following plants: for example, cereals (e.g., rice, barley, wheat, rye, oat, corn, etc.), beans (soybean, red bean, kidney bean, broad bean, pea, peanut, etc.), fruit trees/fruits (apple, citrus, pear, grape, peach, japanese apricot, cherry, walnut, bitter almond, banana, strawberry, etc.), vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, welsh onion, pepper, etc.), root crops (carrot, potato, sweet potato, radish, lotus root, turnip, etc.), plants used as industrial raw materials (cotton, hemp, paper mulberry, trident, rape, beet, hops, sugarcane, sugar beet, olive, rubber, palm, coffee, tobacco, tea, etc.), cucurbitaceae (pumpkin, cucumber, watermelon, melon, etc.), herbaceous plants (duck grass, sorghum, timothy-grass), clover, alfalfa (alfa), etc.), (, Turfgrass (zoysia japonica, glume clippings, etc.), spice plants (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), etc., and flowers (chrysanthemum, rose, orchid, etc.).
The compounds of the formula (I) according to the invention are particularly suitable for controlling coffee nematodes, in particular Brevibacterium pratylum, Brevibacterium coffeelings, Meloidogyne brevicaulis, Meloidogyne incognita, Cofferdaria, Helicoverpa species and Parana, Nematoda, Endocodaria, Pratenseus and Strongyloides.
The compounds of the formula (I) according to the invention are particularly suitable for controlling potato nematodes, in particular pratylenchus praecox, pratylenchus spinosus, pratylenchus penetrans, pratylenchus coffea, pratylenchus fasciatus and pratylenchus ehrens, pratylenchus andex, pratylenchus cerealis, pratylenchus destructor, pratylenchus falcatus, pratylenchus praecox, pratylenchus somi, pratylenchus somnatus, pratylenchus destructor, pratylenchus praecox, praecotylenchus praecotylus, Meloidogyne javanica, Heterokeda, Heliothis virescens, Heliothis tuberosa, Heterostemma rot, Parathelynchus, Heterotylenchus, Heteroclipus isoaphrodisiae, Pseudodactylenchus pratense, and Heteroclida species.
The compounds of the formula (I) according to the invention are particularly suitable for controlling tomato nematodes, in particular of the species Meloidogyne arachidis, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Breynoderma penetrans and Breynia pratensis, Breynia coffea, Breynia stewartii, Breynia destructor, Paradera minutissima, Meloidogyne brevicaulis, Heterodera aberraca, Heterodera pomorum, Heterodera cephalospora and Royledontia reniformis. The compounds of the formula (I) according to the invention are very particularly suitable for controlling soil-dwelling nematode populations in tomato, in particular Meloidogyne incognita.
The compounds of the formula (I) according to the invention are particularly suitable for controlling nematodes of cucumber plants, in particular of peanut root-knot nematodes, northern root-knot nematodes, javanica, southern root-knot nematodes, rotifers nephrotylans and pratylenchus sojae.
The compounds of the formula (I) according to the invention are particularly suitable for controlling cotton nematodes, in particular nematodes of the species Gingstrongylus longipedunculatus, Meloidogyne incognita and Rotylenchus renosus.
The active ingredient combinations according to the invention are particularly suitable for controlling corn nematodes, in particular pratylenchus praecox, pratylenchus spinosus, pratylenchus penetrans, pratylenchus maydis, pratylenchus parvus, thoracotylenchus norvegicus, dactylenchus brevicaulis, Meloidogyne arenaria thamsis, Meloidogyne graminis, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne nasalis, heterodera avenae, heterodera oryzae, heterodera zeae, heterodera chardona, heterodera teasel, caenorhabditis elegans, heterodera macrotylenchus, caenorhabditis, heterodera digitorum, heterodera bicoloris, heterodera longum, heterodera ruscus, heterodera, The nematodes include, but are not limited to, nematodes such as praecox, reniform, cromatoid, clear dwarf, Kletto dwarf, maximum dwarf, nude dwarf, common dwarf, fifth groove nematode, nonsmoneedle nematode, Microcoleoptile, Mesorethorn wild-type rageensis, Triticum aestivum, Ceratodes arachidis, Microcoleoptidae and Geotrichum goides .
The compounds of the formula (I) according to the invention are particularly suitable for controlling soybean nematodes, in particular pratylenchus praecox, pratylenchus penetrans, pratylenchus schoensis, pratylenchus praecox, heterodera glycines, nema colubriformis and pratylenchus cofacis, pratylenchus hexalyticus, pratylenchus destructor, pratylenchus nickelatus, pratylenchus destructor, pratylenchus maydis, pratylenchus destructor, pratylenchus parvus, pratylenchus cerealis, meloidogyne arachidis, meloidogyne incognita, meloidogyne javanica, meloidogyne hapla, columbia, caenorhabditis and renia reniformis.
The compounds of the formula (I) according to the invention are particularly suitable for controlling tobacco nematodes, in particular Meloidogyne incognita, Meloidogyne javanica and Brevibacterium divaricatum, pratylenchus praecox, Brevibacterium hexalyticum, Brevibacterium punctatum, Brevibacterium farinaceae, Brevibacterium crepidium, Brevibacterium sojae, Brevibacterium destructed, Brevibacterium zeae, Brevibacterium elongatum, Pseudoperonospora schizophyllum, Burkholderia species, Meloidogyne incognita, Heterodera globosa, Heterodera virginiae (Globodera virginiae), Clerodera dipterex, Anastrophelus species, Periploca species, Heterodera glomerata, Heterodera crinita, Klettii, Brevibacterium parvum species and tobacco mats.
The compounds of the formula (I) according to the invention are particularly suitable for controlling citrus nematodes, in particular Brevibacterium coformis and Brevibacterium flavum, Brevibacterium atraumatic, Ceratopterus longus, Microtrichinellidae, Bursaphelenchus callorum, Bursaphelenchus, Meloidogyne incognita, Meloidogyne javanica, Heterodera macrocephala, Ceratoptera brevicaulis, Gloeostertagi, Cyclotylenchus species, Cyclotylenchus hemipilus, Peroideus similis and Citrus hemiperforans, Coloraria sciformis, Hemicliophora nudata and Citrus hemiperforans.
The compounds of the formula (I) according to the invention are particularly suitable for controlling banana nematodes, in particular pratylenchus coffea, pratylenchus similis, pratylenchus destructor, meloidogyne species, pleomorphus, helicteres bigemina and reniform nematodes.
The compounds of the formula (I) according to the invention are particularly suitable for controlling pineapple nematodes, in particular pratylenchus maydis, pratylenchus, pratylenchus maydis, pratylenchus gulus, meloidogyne spp, rotiline reniform and extended-longhead nematodes, pratylenchus, protobrex, microdosiphon, heterodera spp, phomopsis longissima, caenorhabditis elegans, pseudodyclonus, lemonella indica, caenorhabditis obliquus, helicotylenchus brevus, helicotylenchus fasciatus, helicotylenchus erythrinae han, Ensiformis pratensis, Peroideus similis, Debreda digitalis, British Breda, Astrabeculoides robusta, Globodera magna, Leptoterus magnus, Pseudohalenchuus minutus, Trichinella furiosus, Trichinella russianus and Thonematodinus.
The compounds of the formula (I) according to the invention are particularly suitable for controlling grape nematodes, in particular pratylenchus destructor, pratylenchus arachidis, meloidogyne incognita, meloidogyne javanica, canarium encephalus, tagetes, and pratylenchus pratensis, pratylenchus schoensis, pratylenchus decipiens, pratylenchus shortest tail, pratylenchus sojae and hemithorny citrus nematodes.
The compounds of the formula (I) according to the invention are particularly suitable for controlling the woody crop, renocarpus, in particular pratylenchus penetrans and pratylenchus vestigialis, longhorn nematodes, meloidogyne incognita and meloidogyne hapla.
The compounds of the formula (I) according to the invention are particularly suitable for controlling the woody crop species nematodes of the drupe type, in particular pratylenchus penetrans, pratylenchus destructor, pratylenchus arachidis, pratylenchus andrus, meloidogyne javanicus, meloidogyne incognita, nectylenchus, and pratylenchus shortest tail, pratylenchus coffeacus, pratylenchus schlegelii, pratylenchus maydis, pratylenchus longissinus, spirodiculus diculus, canaria virens, dactylenchus sinuatus, clendon dwarfish, ancyloides crocodiella, strongyloides juvenia, pratylenchus juvenialis and nema capsulatus.
The compounds of the formula (I) according to the invention are particularly suitable for controlling nematodes, in particular Burkholderia species, Microcyclodex species and Brevibra species, Bursaphelenchus species, Meloidogyne species, Helicosaphus species, Bretylenchus species, Gloeostereum species, Heterodera species, Endocarpus species and harmful necrotizing nematodes, in woody crops, in sugar cane and in rice.
Preparation
Conventional formulations are, for example, water-soluble Solutions (SL), Emulsion Concentrates (EC), aqueous Emulsions (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), Granules (GR) and capsule Concentrates (CS); these formulations and other possible formulation types are described, for example, by International Crop Life (Crop Life International) and in the Pesticide Specifications (Pesticide Specifications), the United nations food and agriculture organization and the world health organization handbook of Pesticide development and use (Manual on maintenance and use of FAO and WHO Specifications for pesticides), the United nations food and agriculture organization Plant Production and Protection document 173(FAO Plant Production and Protection document 173) (established by the United nations food and agriculture organization/world health organization in relation to the Joint conference on Pesticide Specifications 2004, ISBN: 9251048576). In addition to one or more active ingredient combinations according to the invention, the formulations optionally comprise further agrochemical active ingredients.
Preference is given to formulations or use forms which comprise auxiliaries, such as extenders, solvents, spontaneous accelerators, carriers, emulsifiers, dispersants, antifreeze agents, biocides (biochides), thickeners; and/or other adjuvants.
These formulations are prepared in a known manner, for example by mixing the active ingredient combinations according to the invention with auxiliaries (for example extenders, solvents and/or solid carriers) and/or further auxiliaries (for example surfactants). The formulations are prepared in a suitable apparatus, either before or during administration.
The adjuvants used may be substances which are suitable for imparting specific properties (for example certain physical, technical and/or biological properties) to the formulations of the active ingredient combinations according to the invention or to the use forms prepared from these formulations (for example ready-to-use pesticides, such as spray liquors or seed dressing products).
Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, such as aromatic and nonaromatic hydrocarbons (for example paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), ketones (for example acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, unsubstituted and substituted amines, amides, lactams (for example N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (for example dimethyl sulfoxide), carbonates and nitriles.
If the extender used is water, it is also possible to use, for example, organic solvents as cosolvents. Useful liquid solvents are mainly: aromatic compounds, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as petroleum fractions, mineral oils and vegetable oils; alcohols (e.g., butanol or ethylene glycol) and ethers and esters thereof; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents such as dimethylformamide and dimethylsulfoxide; a carbonate (e.g., propylene carbonate, butylene carbonate, diethyl carbonate, or dibutyl carbonate) or a nitrile (e.g., acetonitrile or propionitrile).
In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons such as cyclohexane, paraffin, petroleum fractions, mineral oils and vegetable oils; alcohols, such as methanol, ethanol, isopropanol, butanol or ethylene glycol, and ethers and esters thereof; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethyl sulfoxide; carbonates (such as propylene carbonate, butylene carbonate, diethyl carbonate, or dibutyl carbonate); nitriles (e.g., acetonitrile or propionitrile); and water.
In principle, all suitable carriers can be used. More specifically, suitable carriers include: for example ammonium salts and crushed natural rocks (e.g. kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth), and crushed synthetic rocks (e.g. finely divided silica, alumina) as well as natural or synthetic silicates, resins, waxes and/or solid fertilizers. Mixtures of such carriers can likewise be used. Useful carriers for granules include: for example, crushed and fractionated natural rocks (for example calcite, marble, pumice, sepiolite, dolomite), and synthetic granules of inorganic and organic powders, and granules of organic materials (for example sawdust, paper, coconut shells, maize cobs and tobacco stalks).
Liquefied gaseous extenders or solvents may also be used. Particularly suitable extenders or carriers are those which are gaseous at standard temperature and atmospheric pressure, such as aerosol propellants (e.g. halogenated hydrocarbons), and butane, propane, nitrogen and carbon dioxide.
Examples of emulsifiers and/or foaming agents, dispersants or wetting agents, or mixtures of these surface-active substances, of ionic or nonionic character are: salts of polyacrylic acids; salts of lignosulfonic acid; salts of phenolsulfonic or naphthalenesulfonic acids; polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols, preferably alkylphenols or arylphenols; a salt of sulfosuccinic acid ester; taurine derivatives (preferably alkyl taurates); a derivative of isethionic acid; phosphoric esters of polyethoxylated alcohols or phenols; fatty acid esters of polyhydric alcohols; and derivatives of compounds including sulfates, sulfonates and phosphates, such as alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulfite waste liquors and methylcellulose. The presence of a surfactant is advantageous if one of the active ingredient combinations of the invention and/or one of the inert carriers is insoluble in water and when applied in water.
Other adjuvants which may be present in the formulations and the use forms obtained therefrom include dyes such as inorganic pigments, for example iron oxide, titanium oxide and prussian blue; and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes; and nutrients and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Further components which may be present are stabilizers (e.g. low-temperature stabilizers), preservatives, antioxidants, light stabilizers or other agents which improve the chemical and/or physical stability. A foaming or defoaming agent may also be present.
Furthermore, the formulations and the use forms obtained therefrom may also comprise the following as further auxiliaries: binders, such as carboxymethyl cellulose; and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate; or natural phospholipids (e.g., cephalins and lecithins) and synthetic phospholipids. Other adjuvants may be mineral and vegetable oils.
If appropriate, further auxiliaries may also be present in the formulations and the use forms obtained therefrom. Examples of such additives are fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrating agents, retention promoters, stabilizers, chelating agents, complexing agents, wetting agents, spreading agents. In general, the active ingredient combinations of the invention can be combined with any solid or liquid additive customarily used for formulation purposes.
Examples of the use
Example 1:
tomato plants of the "Rentita" variety were treated to be resistant to Meloidogyne incognita in six replicates. The plants in the growth stage (BBCH 13) were planted in standard soil (sandy loam, consisting of 56.3% sand, 12.3% clay, 31.5% silt, 1.8% humus, pH 7.1) in 11 pots. The water content of the soil is 60-80% of the water holding capacity of the field. The growth conditions were set at 25 ℃, 60-70% relative humidity and 14 hours of light/day (sodium vapor lamp). Three days after planting, each plant was infested with 4000 (J2) juvenile stages (4ml) of Meloidogyne incognita at four sites at a depth of 2 cm. One day after infection, the active ingredient is applied. At this point, the active ingredient of example (I-2) (SL200) and a commercial standard spirotetramat (SC240) were applied by watering at a liquid volume of 60 ml/plant at the application rate indicated. Evaluation was carried out 34 days after infestation by determining the number of eggs/gram of root mass as a measure of nematode reproductive performance.
Example 2:
tomato plants of the "Rentita" variety were treated to combat Meloidogyne incognita in three replicates. The plants in the growth stage (BBCH 13) were planted in standard soil (sandy loam, consisting of 55.5% sand, 11.1% clay, 33.3% silt, 1.6% humus, pH 6.8) in 11 pots. The water content of the soil is 60-80% of the water holding capacity of the field. The growth conditions were set at 25 ℃, 60-70% relative humidity and 14 hours of light/day (sodium vapor lamp). Two days after planting, each plant was infested with 2000 (2ml) or 4000 (4ml) (J2) juvenile stages of Meloidogyne incognita at four sites at a depth of 2 cm of the plant. The active ingredients were tested in two different cases: one day before infection (before infection) and one day after infection (after infection). At this point, the active ingredient of example (I-2) (SL200) was applied by watering at a liquid volume of 60 ml/plant at the application rate indicated. Evaluation was carried out 32 days after infestation by determining the number of eggs/gram of root mass as a measure of nematode reproductive performance.
Some of the standard active ingredient formulations described in the examples are commercially available; some can be prepared by standard methods.
SL formulations of compounds of formula (I-2) (SL200) may be prepared analogously to the formulations described in WO 2009/115262.
Claims (7)
1. Use of a compound of formula (I) for reducing the population of soil-dwelling nematodes after soil application,
wherein
W and Y are independently hydrogen, C1-C4-alkyl, chloro, bromo, iodo or fluoro,
x is C1-C4Alkyl radical, C1-C4-alkoxy, chlorine, bromine or iodine,
d is hydrogen or a methyl group,
A. b together with the carbon atom to which they are attached is saturated C3-C6-cycloalkyl, wherein one ring member is optionally replaced by nitrogen, and which is optionally substituted by C1-C4-alkoxy substituted, or
A. B together with the carbon atom to which they are attached is C substituted by alkylenedioxy3-C6Cycloalkyl, said alkylenedioxy being optionally substituted by C1-C4-alkyl or C1-C4-alkoxy-C1-C2-alkyl is substituted and forms, together with the carbon atom to which it is attached, a five-or six-membered ketal,
g is hydrogen (a) or one of the following groups
Wherein
E is a metal ion or an ammonium ion,
m is oxygen or sulfur, and M is oxygen or sulfur,
R1is straight chain or branched C1-C6-an alkyl group,
R2is straight chain or branched C1-C6-an alkyl group.
2. Use according to claim 1, wherein the compound of formula (I) has the following definition:
w is a methyl group, and W is a methyl group,
x is chlorine or methyl, and X is chlorine or methyl,
y is chlorine, bromine or methyl,
d is hydrogen, and the compound is shown in the specification,
A. b together with the carbon atom to which they are attached is saturated C6-a cycloalkyl group substituted with an alkylenedioxy group which together with the carbon atom to which it is attached forms a five-or six-membered ketal,
g is hydrogen (a) or one of the following groups
Wherein
M is oxygen, and M is oxygen,
e is a monovalent metal ion or an ammonium ion,
R1is straight chain or branched C1-C4-an alkyl group,
R2is straight chain or branched C1-C4-an alkyl group.
3. Use according to claim 1, wherein the compound of formula (I) is selected from the following compounds:
4. the use according to claim 1, wherein the compound of formula (I) has the following structure:
5. use of a compound of formula (I) according to claim 1 for reducing the soil-dwelling nematode population after soil application in tomato.
6. Use of a compound of formula (I) according to claim 1 for reducing soil-dwelling meloidogyne incognita populations after soil application.
7. Use of a compound of formula (I) according to claim 1 for reducing the population of soil-dwelling meloidogyne incognita after soil application in tomato.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18167241.1 | 2018-04-13 | ||
| EP18167241 | 2018-04-13 | ||
| PCT/EP2019/059436 WO2019197616A1 (en) | 2018-04-13 | 2019-04-12 | Use of tetramic acid derivatives for reducing nematode populations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112040774A true CN112040774A (en) | 2020-12-04 |
Family
ID=62001974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201980025627.3A Pending CN112040774A (en) | 2018-04-13 | 2019-04-12 | Use of tetramic acid derivatives for reducing nematode populations |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP3772957A1 (en) |
| CN (1) | CN112040774A (en) |
| BR (1) | BR112020019819A2 (en) |
| MX (1) | MX2020010685A (en) |
| WO (1) | WO2019197616A1 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101160049A (en) * | 2005-02-22 | 2008-04-09 | 拜尔农作物科学股份公司 | Spiroketal-substituted cyclic ketoenols |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006007882A1 (en) * | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | New cyclic keto enol derivatives useful for controlling animal pests and/or unwanted plant growth |
| DE102006057036A1 (en) * | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | New biphenyl substituted spirocyclic ketoenol derivatives useful for the manufacture of herbicides and for combating parasites |
| EP2039248A1 (en) | 2007-09-21 | 2009-03-25 | Bayer CropScience AG | Active agent combinations with insecticide and acaricide properties |
| ES2398315T3 (en) | 2007-12-20 | 2013-03-15 | Bayer Cropscience Ag | Use of tetramic acid derivatives to fight nematodes |
| EP2103615A1 (en) * | 2008-03-19 | 2009-09-23 | Bayer CropScience AG | 4'4'-Dioxaspiro-spirocyclic substituted tetramates |
-
2019
- 2019-04-12 MX MX2020010685A patent/MX2020010685A/en unknown
- 2019-04-12 BR BR112020019819-6A patent/BR112020019819A2/en not_active Application Discontinuation
- 2019-04-12 EP EP19716428.8A patent/EP3772957A1/en not_active Withdrawn
- 2019-04-12 WO PCT/EP2019/059436 patent/WO2019197616A1/en active Application Filing
- 2019-04-12 CN CN201980025627.3A patent/CN112040774A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101160049A (en) * | 2005-02-22 | 2008-04-09 | 拜尔农作物科学股份公司 | Spiroketal-substituted cyclic ketoenols |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3772957A1 (en) | 2021-02-17 |
| BR112020019819A2 (en) | 2021-01-05 |
| WO2019197616A1 (en) | 2019-10-17 |
| MX2020010685A (en) | 2020-11-06 |
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