SU955677A1 - Lactam and transition metal salt metallic complexes having fungicide activity against late blight tomatoes, anticeptic and fungicide activity against late blight-of, anticeptic and fungicide activity against potato brown patch - Google Patents

Lactam and transition metal salt metallic complexes having fungicide activity against late blight tomatoes, anticeptic and fungicide activity against late blight-of, anticeptic and fungicide activity against potato brown patch Download PDF

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SU955677A1
SU955677A1 SU802944459A SU2944459A SU955677A1 SU 955677 A1 SU955677 A1 SU 955677A1 SU 802944459 A SU802944459 A SU 802944459A SU 2944459 A SU2944459 A SU 2944459A SU 955677 A1 SU955677 A1 SU 955677A1
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activity against
fungicide activity
anticeptic
late blight
compounds
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SU802944459A
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Russian (ru)
Inventor
С.И. Шестакова
С.С. Кукаленко
Е.И. Андреева
Т.А. Уланова
В.И. Монова
Е.К. Юхнина
Н.И. Шувалова
Л.А. Филимонова
Н.Б. Полякова
А.И. Белкин
Б.А. Заикин
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Предприятие П/Я Р-6225
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Priority to SU802944459A priority Critical patent/SU955677A1/en
Priority to DE19813123208 priority patent/DE3123208A1/en
Priority to CH398781A priority patent/CH644491A5/en
Priority to JP9238681A priority patent/JPS5728044A/en
Priority to GB8118738A priority patent/GB2078740B/en
Priority to FR8112005A priority patent/FR2485010B1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
    • 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
    • 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
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
    • C07D201/14—Preparation of salts or adducts of lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D223/08—Oxygen atoms
    • C07D223/10—Oxygen atoms attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Complex salts of lactams or thiolactams and halides or nitrates of heavy metals have the following general formula: <IMAGE> wherein: Me is Cu<II>, Zn, Mn, Hg<II>, or Ni<II>; Y is O or S; X is Cl, Br, or NO3; m = 1 or 2; n = 3 or 5; p = 2 or 4; k = 0 or 1; a = 1,2,3, or 4; and R is H, <IMAGE> Such compounds which are fungicides are prepared by reacting a lactam or thiolactam with a halide or nitrate of a heavy metal in an organic solvent at a temperature of from 20 to 80 DEG C, followed by isolation of the desired product.

Description

Изобретение относитс  к новым химическим соединени м- металличес ким комплексам лактамов и солбй пе реходных металлов, про вл ющим фун гицидную активность против фитофтороза томатов, аНтисептимескую активность и фунгицидную активност п рот ив р изоктониоза ка ртбфел . Известны соединени  общей форму у - о, S; X - Мп С1, ZnCI, CuClj, CuB которые эффективны в качестве Фунгицидов на чистых культурах . pj. Однако известные соединени  не .про вл ют антисептическую актив-, ность. Целью изобретени   вл етс  расш рение арсенала химических средств защиты растений, а также спектра фунгицидного действи . ; Предлагаютс  металлические комплексы лактамов и солей переходных м,еталлрв общей фд1рмулы 1 01 ( СН2)а ИН J m. где а) р 0; П « 3 или 5; Ш 1 или 2; Х-СоС1л или SnCln; S) Р ; п 3 или 5;; m 2; X-N1C12 NKNO). При вышеуказанных значени х р, т, X соединени  формулы I про вл ю фунгицидную активность против фито фтороза томатов. В случае, если П 5; m 2; X - р п . 3 гп « 1 ил 2; X - р п « 3, m 2, , р Ь 7 , :. соединени  формулы 1 про вл ют антисептическую активность. В случае, если п « 3 m 2, :Х-СоС1 п - 5, m « 2, X-NIC),2, р « 1, соединени  формулы I про вл ют фунгицидную активность против ризоктониоза картофел . Предлагаемые соединени  получают, .взаимодействием лактама с солью металла при комнатной температуре или при;, .нагревании в абсолютном спирте ,. Строение полученныхсоединений подтверждено данными ИК-спектров и дериватографии. Пример 1. К1,7 г пирролидона в абсолютном спирте при нагревании добавл ют 2,38 г NfCl2 6H,jO в абсолютном спирте, смесь перемешивают при комнатной температуре в течение 1 ч и спирт упаривают.Остаютс  кристаллы же товато-зеленоватоо цвета. Вес 2,8 г (88%), т.пл. 250 С. Найдено,: С 29,97; Н 5,23; N 8,69; С1 21,89. . бь1числено,%: С 30,19; Н 5,03; N 8,81; С1 22,33. П р и м е р 2. К 1,7 г пирролидона в абсолютном спир(ге при нагревании добавл ют 2,91 т N1 (NO) в абсолютном спирте. Перемешивают при 78°С в течение 1 ч, охлаждают и упаривают спирт Остаютс  кристалш зеленого цвета. Вес их 3 г (81) т.пл. 55-57°С. Найдено, I: С 25,9б; Н 1,82; N И,98. . Вычислено,: С 25,88; Hi,31; N 15,09. Остальные соединени  синтезированы по аналогичным методикам. Их свойства приведены в табл.1. Дл  всех синтезированных соединений сн ты ИК-спектры. Наиболее-характерные полосы поглощени : 3290 , см. Наличие воды в соединени х 5-8 (табл.1) подтверждено методом дёриватографии.The invention relates to new chemical compounds, the m-metal complexes of lactams and transition metals, which exhibit fungicidal activity against tomato late blight, anti-septic activity and fungicidal activity of rt bfell isoctoniosis. Compounds of the general form y - o, s are known; X - Mn C1, ZnCI, CuCl, CuB which are effective as Fungicides on pure cultures. pj. However, the known compounds do not exhibit antiseptic activity. The aim of the invention is to expand the arsenal of plant protection chemicals as well as a spectrum of fungicidal action. ; Metallic complexes of lactams and salts of transition m are available, with total complex of common formula 1 01 (СН2) and IN J m. where a) p 0; P «3 or 5; W 1 or 2; X-CoCl or SnCln; S) P; p 3 or 5 ;; m 2; X-N1C12 NKNO). With the above values of p, t, x of the compound of formula I, the fungicidal activity against phytophorosis of tomatoes is shown. In the event that P 5; m 2; X - p p. 3 gp "1 or 2; X - р п «3, m 2,, р L 7,:. compounds of formula 1 exhibit antiseptic activity. If p 3 m 2,: X-CoC1 p - 5, m 2, X-NIC), 2, p 1, the compounds of formula I show antifungal activity against potato rhizo-toniosis. The proposed compounds are prepared by the interaction of the lactam with the metal salt at room temperature or with ;, heating in absolute alcohol,. The structure of the compounds obtained is confirmed by the data of IR spectra and derivatography. Example 1. To 1.7 g of pyrrolidone in absolute alcohol, 2.38 g of NfCl2 6H, jO in absolute alcohol are added with heating, the mixture is stirred at room temperature for 1 hour, and the alcohol is evaporated. The crystals remain in the same greenish color. Weight 2.8 g (88%), so pl. 250 C. Found: C 29.97; H 5.23; N 8.69; C1 21.89. . without,%: C 30.19; H 5.03; N 8.81; C1 22.33. EXAMPLE 2: To 1.7 g of pyrrolidone in absolute alcohol (2.91 tons of N1 (NO) in absolute alcohol are added while heating). Stir at 78 ° C for 1 hour, cool and evaporate the alcohol. crystal green color. Their weight is 3 g (81) TPL 55-57 ° C. Found, I: C 25.9b; H 1.82; NI, 98. Calculated: C 25.88; Hi , 31; N 15.09. The remaining compounds were synthesized by the same methods. Their properties are listed in Table 1. The IR spectra are the most characteristic absorption bands for all synthesized compounds: 3290, see Water in compounds 5- 8 (table 1) confirmed by the method of denat ography.

Пример 3. Антисептическую активность определ ют на мицелии гриу бов Asperglllus nlgeti Chaetomium globodum, Cladosporlum НегЬагйгаExample 3. Antiseptic activity was determined on the mycelium of the Asperglllus nlgeti mushroom. Chaetomium globodum, Cladosporlum Negygiga

Препараты раствор ют в ацетоне и в стерильных услови х ввод т в расплавленный картофельный агар, ко торый разливают по чашкам Петри из Расчёта 20 мл среды иа чашку.The preparations are dissolved in acetone and, under sterile conditions, are introduced into melted potato agar, which is poured into Petri dishes at a rate of 20 ml of medium and a dish.

Кбицентраци  0,003% по действующему веществу (д.в.).The cubicration is 0.003% for the active substance (AI).

Через 18-20 м после разлива ага- , ровую пластинку иноКулируют кусочком мицели ,. Чашки выдерживают сутоКAfter 18–20 m after the spill of aga-, the gray plate is inoculated with a piece of mycelium,. Cups can withstand a day.

при . Затем определ ют размер колоний треет-объектов и по формуле Эббота процент подавлени  роста мицели  :at. Then, the size of the colonies of the treating objects and the percentage of suppression of mycelium growth are determined by the Abbott formula:

1Пп«---- 100,1PP "---- 100,

где Пп - процент подавлени ;where Pn is the percentage of inhibition;

а - рост.мицепи  грибов в контроле;a is the growth of the fungal mycene in the control;

Ь - рост мицели  грибов с препаратом ..B - growth of fungal mycelium with the drug ..

|Результаты испытани  приведены в табл.2.The test results are shown in Table 2.

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ь Пример k. Испытани  провод  на растени х томатов сорта Грибовекие в возрасте 2-3 недель после пикировки . Опыты закладывают в трех повторност х. Соединени  испытывают в концентрации 0,1% по действующему веществу, расход жидкости 3-6 мл На одно растение. Через 1 ч после обрабртки препаратами растени  инокулируют водной суспензией спор гриба Phytophtora infestans. Концентраци  зооспор в суспензии составл ет 50 тыс. в 1 мл воды. После зараже ни  растени  помещают во влажнул камеру на 2k ч. Подавление развити  болезни рассчитывают по формуле Эббота. Результаты испытаний приведены в табл.2. , Пример 5. Оценку соединений в отношении возбудител  ризоктониоза картофел  провод т на клубн х сорта Дружный С естественным фоном заражени . Клубни обрабатывают суспензией соединений и термостатируют в услови х влажной камеры в т ечение 3- дней. Затем определ ют степень развити  болезни путем подсчета по .общеприн той методике. 9 ,12 В табл.2 приведены результаты испытаний соединений в борьбе с ризоктониозом картофел . ,Фунгицидное действие испытываемых соединений такое , же, как у эталонного соединени -поликарбацина или даже несколько выше. Соединени  обладают более высоким фунгицидным действием, чем используемый дл  этих целей в СССР в cenji г скохоз йственной практике препарат ТМТД. Новые соединени  в отличие от известных обладают широким спектром фунгицидного действи , про вл   акстив ность как против возбудител  фитофтороза томатов и ризоктониоза кйртофел , так и в отношении мицели  грибов Aspergillus niger, Chaetomlum globosum , Cladosporium herbarum. Кроме того, преимуществом предлагаемых соединений  вл етс  их ниэка  токсичность дл  теплокровных (ЛД ООIBlO мг/кг) , в то врем  как известный фунгицид на основе соединений олова трифенилоловоацетат (3) имеет токсичность 125 мг/кг, а соединени  9-12 - ЛД5о5200; 6100; 780 и Ибо мг/кг соответственно.l Example k. Testing the wire on the plants of the variety Griboveki at the age of 2-3 weeks after picking. Experiments are laid in triplicate. Compounds are tested at a concentration of 0.1% active ingredient, liquid flow 3-6 ml per plant. 1 h after treatment with the preparations, the plants are inoculated with an aqueous suspension of spores of the fungus Phytophtora infestans. The concentration of zoospores in the suspension is 50 thousand in 1 ml of water. After an infection, the plants are placed in a dampened chamber for 2k hours. The suppression of the development of the disease is calculated using the Abbott formula. The test results are shown in table 2. , Example 5. Evaluation of compounds in relation to the pathogen rhizoctoniosis of potatoes is carried out on tuber sorts Druzhny With a natural background infection. Tubers are treated with a suspension of the compounds and thermostatted under moist chamber conditions for 3 days. The extent of disease progression is then determined by counting according to the generally accepted method. 9, 12 Table 2 shows the results of tests of compounds in the fight against rhizoctoniosis of potatoes. The fungicidal action of the test compounds is the same as that of the reference compound — polycarbacin or even slightly higher. The compounds have a higher fungicidal effect than the TMTD preparation used in the USSR in the USSR for practical purposes. The new compounds, in contrast to the known ones, possess a wide range of fungicidal action, showed aptitude both against the tomato late blight and rhizoctoniosis of the gertofel and against the mycelium of Aspergillus niger, Chaetomlum globosum, Cladosporium herbarum. In addition, the advantage of the proposed compounds is their niek toxicity to warm-blooded animals (LD OOIBlO mg / kg), while the known fungicide based on tin compounds triphenyltin acetate (3) has a toxicity of 125 mg / kg, and compounds 9-12 - LD5 -5200; 6100; 780 and Ibo mg / kg, respectively.

Claims (1)

Новые соединения в отличие от известных обладают широким спектром фунгицидного действия, проявляя актив ность как против возбудителя фитофтороза томатов и ризоктониоза картофеля, так и в отношении мицелия грибов Азрегд! Пиз * гидег, СЬае£отп1ит д!оЬозит, С1адо5рог!ит ЬегЬагит.New compounds, in contrast to the known ones, possess a wide spectrum of fungicidal action, showing activity both against the causative agent of late blight of tomatoes and potato rhizoctoniosis, and with respect to the mycelium of the fungi Azregd! Pease * Gideg, CHiae £ replies to d! Ozoz, Sadohog! Um bjagit. Кроме того, преимуществом предлагаемых соединений является их низкая\ токсичность для теплокровных (ЛД^бОО1340 мг/кг) , в то время как известный фунгицид на основе соединений олова ·? трифенилоловоацетат (3) имеет токсичность 125 мг/кг, а соединения.In addition, the advantage of the proposed compounds is their low toxicity for warm-blooded animals (LD ^ bOOO1340 mg / kg), while the known fungicide based on tin compounds ·? Triphenyltin acetate (3) has a toxicity of 125 mg / kg, and compounds. 9-12 - ЛД5О5200; 6100; 780 и9-12 - LD 5O 5200; 6100; 780 and 1160 мг/кг соответственно.1160 mg / kg, respectively.
SU802944459A 1980-06-18 1980-06-18 Lactam and transition metal salt metallic complexes having fungicide activity against late blight tomatoes, anticeptic and fungicide activity against late blight-of, anticeptic and fungicide activity against potato brown patch SU955677A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
SU802944459A SU955677A1 (en) 1980-06-18 1980-06-18 Lactam and transition metal salt metallic complexes having fungicide activity against late blight tomatoes, anticeptic and fungicide activity against late blight-of, anticeptic and fungicide activity against potato brown patch
DE19813123208 DE3123208A1 (en) 1980-06-18 1981-06-11 COMPLEX HEAVY METAL HALOGENIDES AND NITRATES WITH LACTAMES OR THIOLACTAMEN, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES
CH398781A CH644491A5 (en) 1980-06-18 1981-06-17 COMPLEX SALTS OF LACTATES OR THIOLACTAMES WITH HALOGENIDES OR NITRATES OF HEAVY METALS, METHOD FOR THEIR PRODUCTION AND FUNGICIDES CONTAINING THE SAME.
JP9238681A JPS5728044A (en) 1980-06-18 1981-06-17 Complex salt comprising heavy metal halide or nitrate and lactam or thiolactam
GB8118738A GB2078740B (en) 1980-06-18 1981-06-18 Complex salts of lactams or thiiolactams and halides or nitrates of heavy metals
FR8112005A FR2485010B1 (en) 1980-06-18 1981-06-18 COMPLEX SALTS OF LACTAMS OR THIOLACTAMS AND HEAVY METAL HALIDES OR NITRATES, PROCESS FOR THEIR PREPARATION AND THEIR USE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU802944459A SU955677A1 (en) 1980-06-18 1980-06-18 Lactam and transition metal salt metallic complexes having fungicide activity against late blight tomatoes, anticeptic and fungicide activity against late blight-of, anticeptic and fungicide activity against potato brown patch

Publications (1)

Publication Number Publication Date
SU955677A1 true SU955677A1 (en) 1983-06-15

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SU802944459A SU955677A1 (en) 1980-06-18 1980-06-18 Lactam and transition metal salt metallic complexes having fungicide activity against late blight tomatoes, anticeptic and fungicide activity against late blight-of, anticeptic and fungicide activity against potato brown patch

Country Status (6)

Country Link
JP (1) JPS5728044A (en)
CH (1) CH644491A5 (en)
DE (1) DE3123208A1 (en)
FR (1) FR2485010B1 (en)
GB (1) GB2078740B (en)
SU (1) SU955677A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0257063B1 (en) * 1986-01-31 1992-06-17 WHITBY RESEARCH, Inc. Compositions comprising 1-substituted azacycloalkanes and their uses

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2854458A (en) * 1954-07-15 1958-09-30 Basf Ag Complex heavy metal salts
US3085931A (en) * 1960-03-17 1963-04-16 Monsanto Chemicals Plant virus growth inhibitors
US3077477A (en) * 1960-05-12 1963-02-12 Rohm & Haas Lactams and methods of preparation
US3235455A (en) * 1962-02-09 1966-02-15 Procter & Gamble Synergistic antibacterial compositions
US3499867A (en) * 1965-06-22 1970-03-10 Toyo Boseki Stabilized polyamide composition
US3488732A (en) * 1967-02-21 1970-01-06 Mobil Oil Corp Heterocyclic ring compounds and preparation of same
US3828028A (en) * 1971-04-30 1974-08-06 Ube Industries Process for preparing lactam complexes
US3868354A (en) * 1973-12-13 1975-02-25 Firestone Tire & Rubber Co New catalyst for hydrogenation of elastomers and the process of hydrogenation
US3872072A (en) * 1973-12-13 1975-03-18 Firestone Tire & Rubber Co New hydrogenation catalyst for elastomers, and the process of hydrogenation
US4069038A (en) * 1975-03-28 1978-01-17 Stauffer Chemical Company Acyclic and alicyclic N-substituted halo-2-pyrrolidinones and their utility as herbicides
BR8000986A (en) * 1979-02-22 1980-10-29 Chevron Res FUNGICIDE COMPOUND, PROCESS TO CONTROL THE GROWTH OF FUNGI, COMPOSITION OF FUNGICIDES AND PROCESS FOR THE CONTROL OF FUNGI

Also Published As

Publication number Publication date
JPS5728044A (en) 1982-02-15
CH644491A5 (en) 1984-08-15
GB2078740B (en) 1985-06-05
FR2485010A1 (en) 1981-12-24
DE3123208A1 (en) 1982-04-08
FR2485010B1 (en) 1985-10-18
GB2078740A (en) 1982-01-13

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