JPS58164550A - Cyclohexan-1,3-dione derivative, manufacture and herbicide - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed Description of the Invention] +The invention is a cyclohexane-1,3-dione conductor,
Its production method and its chemical threat'+/J'ft active substance@
Regarding herbicides with.

Cyclohexane-1,3-dione 44? It is well known that it can be applied to properly exterminate undesirable carnivorous plants in wide fruit cultivation (1976).
No. 19945@i).

By the way, formula 1: [During the ceremony.

The element is substituted by one or more salt atoms, bromine atoms, alkyl or alkoxy groups each having 1 to 3 carbon atoms, or a phenyl group. 3 to 6 carbon atoms 't-
A cycloalkyl group, or a chlorine atom by J#@,
A bromine atom is interrupted by one or more alkyl or alkoxy groups or phenyl groups each having from 1 to 41 carbon atoms.

A cycloalkyl group containing all 7 to 1211 subatomic atoms.

Bicycloalkyl group 1 A tricycloalkyl group, cycloalkenyl group, bidicloalnanyl group or tricycloalkenyl group.

y represents a hydrogen atom, a methoxycarbonyl group or an ethoxycarbonyl group.

R' represents an alkyl group having 1 to 4 carbon atoms, and R' represents an alkyl group having 1 to 3 carbon atoms.

artenyl group with 3 or 4 carbon atoms, 3 or 4
represents a halogen alkenyl group or propargyl group having 1 to 3 carbon atoms and 1 to 3 helogen tM substituents]. !II') It has been discovered what has good herbicidal action against a number of other species that challenge knowledge. At the same time, the new additions mentioned in the separate article are highly sensitive to a large number of cultivated and other species that are not found in other species and other species.
Boss.

Furthermore, specific compounds! ? IJ has selectivity for some cultivated plants, such as rice or wheat.

Compounds of formula I can be produced in a number of tautomeric forms, which are encompassed within the range of six obvious 'c+ = 8* requirements: FFOR'0 Cycloalkyl, bicycloalkyl or tricycloalkyl group having 7 to 12 carbon atoms 9 Examples include cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, bicyclohebutyl Examples include bicyclo[ 2, 2, 1]
-to] butyl-2bicyclooctyl, tricyclooctyl, bicyclononyl, tricyclononyl, bicyclononyl.

Tricyclodecyl, bicyclododecyl, tricyclododecyl, or a cycloalkenyl group having 7 to 12 carbon atoms, a bicycloalkenyl group, or a tricycloalkenyl group 9 For example, a cycloartenyl group, a cycloalkagenyl pongee, a cycloalkenyl group trienyl or cycloalkatetraenyl groups and di- and tri-horizontal groups having 1 to 4 double bonds, such as cycloheptenyl, cyclooctenyl, cyclooctagenyl, cyclononenyl, cyclodecenyl, cyclododecenyl, cyclododecagenyl, such as cyclododeca dien-1,5-yl-9, cyclododecatetraenyl e.g. cyclododecatetraene-1
,3,5,7-yl-1o.

Bicyclohebutenyl example is bicycloC2,2,1]-hebuten-2-yl-5,bicyclooctenyl.

Bicyclononenyl, bicyclodecenyl. Contains tricyclodecenyl and bicyclododecadienyl.

These groups include a salt atom, a carbon atom, an alkyl group having 1 to 4 carbon atoms such as methyl, an alkoxy group having 1 to 4 carbon atoms such as methoxy, or a phenyl group with one or more carbon atoms. It may be possible to cooperate. This kind of base lending auction is 3,7. '7-Dorimethylbicyclo[4,
1,0]-to]butyl-42,6.6-)limethylbicyclo[3,1,1]butyl-3,'7.7-dichlorobicyclo[4°1.0]butyl-3, 4-methyl-7
,7-dichlorobicyclo[4,1,0:]]butyl3. tricyclo5.2.0”・6]decen-8-yl-
4, tricyclo[5,2,1,0',d]]decene-8-yl-37.7-dibrombicyclo(4,1,O)
Hebutyl-3.

Furthermore, R' can be a salt atom, a certain atom, an alkyl group having 1 to 3 carbon atoms, such as methyl, an alkoxy group, such as methoxy, or a phenyl group, each having 1 to 311 carbon atoms. That's all for now.

3-6 (cycloalkyl group having +- carbon atoms.

tlJ Examples include 2,2-dichlorocyclopropyl, 3-phenyl-2,2-dichlorocyclopropyl, 4-methoxy-cyclohexyl, 2,2,6-)dimethylcyclohexyl. 4-chloro-cyclohexyl, 2-phenyl-4
-Methyl-cyclohexyl can be used.

Nobi in formula l is an unbranched or branched alkyl group having 1 to 4 carbon atoms, i.e. methyl, ethyl,
n-propyl, 1-propyl, n-butyl 5ec
-Butyl, i-butyl, tert-butyl.

The radicals in formula I include propargyl radicals, alkyl radicals having 1 to 3 carbon atoms, alkynyl radicals having 3 or 4 carbon atoms, or 3 or 4 carbon atoms and up to 3 halogen substituents. halogenalkenyl groups with 1 such as methyl, ethyl, n-propyl, 1-propyl, n-butyl, 5ec-butyl91-butyl, tert-butyl, allyl, 1-chloroproby-1-en-3-yl, 2-chloroproby 1-en-3-yl, 1,3-dichloroprob-1-en-3-yl, 1. 1, 2-trichloroprob-1-en-3-yl.

Salts of the compound of formula I include alkali metal salts.

Especially potassium salts or sodium salts, alkaline earth gold salts, especially calcium salts, magnesium salts or barium salts,
This includes manganese salts, copper salts, zinc salts, and iron salts.

The compound of formula 1 is formula 1: 0 R.

[In the formula, R', R' and ? represents the above-mentioned compound] The compound represented by hydroxylamine compound: 0-NH5Y (wherein, 0-NH5Y represents the above-mentioned compound)
represents an anion) and anti-hc:.

The anti-H6 is preferably a heterogeneous phase in an inert bath agent with a range of 0 to 80
C. or O.degree. C. to the boiling point of the anti-1+6 compound in the presence of a base. Commercially available bases include, for example, those compiled by Alkali Publishing Co., Ltd. or alkaline earth fluorophores, especially sodium, potassium, magnesium, and calcium cadaver salts, hydrogen salts,
uF, acid salt, alcoholade.

It is a water drink or an oxide. Additionally, organic bases such as pyridine or tertiary amines may be used in the pH range 2-8. In particular, it progresses particularly well between 4.5 and 5.5. Adjustment of the pH range is advantageously carried out using acetate.

This can be done, for example, by adding an alkali metal acetate, in particular sodium acetate or potassium acetate, or a mixture of both salts. Alkali metal acetate has the formula: R
For example, 0 for the ammonium compound of '0-NH8Y.
．． Add a key of 5 to 2 moles.

Examples of m-agents include dimethyl sulfoxide.

Alcohols include methanol, ethanol, isopropanol, benzene, chlorinated alcohols such as chloroform, dichloroethane.

Hexane, cyclohexane, esters such as acetic acid ethyl ester, ethers such as dioxane, tetrahydrofuranka are suitable.

The reaction is complete after a few hours and the reaction product is then mixed, mixed with water and extracted with a non-inertial bath agent such as methylene chloride, and the bath agent is distilled off under reduced pressure. It is possible to perform a single function.

Furthermore, 1 compound of formula I is a compound of formula 2 compound of formula H: Formula: R'0-N
It can be obtained by reacting a hydroxylamine represented by H2 (in the formula, represents the above) in an inert diluent at a temperature of 0°C to the boiling point of the anti-oxidant mixture, especially 15 to 70°C. . Optionally, hydroxylamine can also be used as a water bath liquid.

Suitable bath agents for this reaction are, for example, alcohols such as methanol, ethanol, isopropanol, cyclohexanol, optionally chlorinated carbonized ice creams such as hexanes, cyclohexane.

Methylene chloride, toluene, dichloroethane, esters such as acetic acid ethyl ester, nitriles such as acetonitrile, cyclic ethers such as tetrahydrofuran.

Alkali gold j of the compound of formula 1! The 6-salt can be obtained by treating the compound with woodblock sodium or potassium hydride in ml of water or an organic bath such as methanol, ethanol, acetone A.

Sodium and potassium alcoholades can also be used as bases.

The fluorine salts, such as manganese, copper, zinc, iron, calcium, magnesium and barium salts, can be prepared from the sodium salts by reaction with the corresponding metal chlorides in aqueous solution. .

Compounds of formula 1 can also exist in tautomeric forms 111a and lb. (Tetrahedr
29, 2491 (1975)].

Optionally, the compound of formula ■ may be used in the reaction of formula H! It is produced as a mixture of A and is rearranged in the presence of imidazole or pyridine conductors (Japanese Patent Publication No. 54-630).
No. 52) It is also possible to produce it through an intermediate step of enol ester.

Combination of 2■? ! HaCOOC
U The method for producing the cyclohexane-1,3-dione compound of formula 1 will now be described in Examples. In the example, 亘力都 and 过翫都 have a relationship between kilograms and liters.

¥Example 1 2-butyryl-5-cyclooctylcyclohexane-1
, 3-dione 4.9 nuts, ethoxyamine 1.
Stir 1 plate of Judu and 80 volumes of ethanol in Shikai for 1z hour. The bath agent was distilled off under 0R pressure, the residue was collected in 150 parts of dichloromethane, the bath solution was rinsed twice with water and sulfuric acid), and the bath agent was dried over IJum and the bath agent was removed under reduced pressure. To leave. Oily? /l (nD=1.5234)9
2-(l-ethoxyamino-butylidene) in 4% yield
-5-cyclooctylcyclohexane-1,3-dione (Compound Shop 1) is obtained.

C2oHasNO3 (335) Calculated value: C71,6H9,9N 44 Actual value: C'
72. OH9,9N 4.1 Example 2-proionyl-5-(2,6,6-dimethylbicyclo[3,1,1]to1-methyl)-cyclohexane-
1,3-dione'7.5 coulometric m, allyloxyammonium chloride 2-9]tkhd, anhydrous sodium chloride 2.21 IL parts and ethanol-yvBOmlk at draft temperature 12
The time was stirred. The bath agent was distilled off under completely reduced pressure, and the residue was dissolved in water 12
9. Stir 0 and 100 methylene chloride in one vessel, and remove all the contents.9. The aqueous phase was extracted with 50 methylene chloride and the combined organic phases were washed with water, dried over sodium sulfate and concentrated under reduced pressure.

2-(1-allyloxyaminopropylidene)- in 91% yield as the precursor (nfi6 = 1.5317)
5-(2,6,6-drimethylbicyclo[3,1゜1]
-Hept-3-yl)-cyclohexane-1°3-dione (Compound Shop 2) is obtained.

C22HasNO3 (360) Calculation 1M: C73,5H9,2N 3.9 Actual measurement 1m
: C'73.9 H9, I N 3.8 Similarly, the following compound stock f was obtained.

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ω85
//H86
〃H87/T
H88〃
H89 Cyclo-P-traen-1,3,5,H7-yl-10 90〃 H91
cyclooctatriene-1,3,5-Hyl-7 92〃 H93 cyclooctadiene-1,3-yl-6H94〃
H96〃
H97 cyclohebutyl
H98〃
H99〃
Hloo 1.43)-dimethyl-cyclohexene H-3-ylethyl ethylallyl 3-chlorallyl Vg-dishin-7b ethylallylethyl; For example, solutions, powders, suspensions, and even aqueous, oily or other suspensions or dispersions, emulsions, which can be used as a cough reliever.

It can be applied in the form of oily dispersions, pastes, dusts, spreaders or granules by blasting, misting, dusting, spreading or injection. The format for the application depends entirely on the intended use; in each case it should be ensured that the active substance of the invention is as fine as possible.

In order to produce directly splashable bath liquids, milk powders, pastes and oil dispersions, medium to high non-point mineral oil fractions such as coal oil or diesel oil, as well as coal tar oil, etc., as well as other physical properties or Before Animal Sources, Aliphatic, Cyclic & Aromatic &
Yobi Hyouka such as Penzol, Dorol, Kijiroll,
paraffin.

Tetrahydronaphthalene, alkyl 7m naphthalene or its derivatives Examples include methanol, ethanol, propatool, butanol, chloroform.

carbon tetrachloride, cyclohexanol, cyclohexanone,
Chlorbenzole, isophorone, etc. Strong solvents such as dimethylformamide, dimethylsulfoxide, etc.
N-methylpyrrolidone and water are used.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders), oil dispersions by addition of water. To produce emulsions, pastes or oil dispersions, the substances may be mixed homogeneously in water, either as such or dissolved in oil or solvents, with the aid of wetting agents, dispersing agents or emulsifying agents. can. In addition, it is also possible to prepare concentrates consisting of the active substance, wetting agents, coating agents, dispersants or emulsifiers and optionally solvents or oils, which are then diluted with water.

Clothing dryness v! The following substances can be mentioned; lignin sulfone and naphthalene sulfone.

Alkaline salts of phenolsulfone, alkaline earth mm
, ammonium salt, alkylarylsulfonate,
Alkyl sulfates, alkyl sulfonates, alkali and alkaline earth salts of diptylnaphthalene sulfonic acid, lauryl ethyl sulfate, fatty alcohol sulfates.

Fatty acid alkali salts and alkaline earth salts, sulfated hexadecanol, heptadecanol, octadecanol salts,
Condensation products of sulfonated fatty alcohols, salts of recall ethers, sulfonated naphthalenes or naphthalene derivatives and formaldehyde.

Polyoxyethylene-octylphenol ether, a condensation product of naphthalene or naphthalene sulfonic acid, phenol and formaldehyde.

Ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohol, isotridecyl alcohol *j= Fatty flucol ethylene oxide constrictor.

Ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol ester, lignin, sulfite waste liquor and methyl cellulose.

Powders, dusting powders and sprinkles can be prepared by mixing or milling the active substance and solid carrier material together.

Granules such as V pseudo-1 permeation and homogeneous granules.

They can be produced by binding the active substance to a solid carrier material. Solid support materials are, for example, minerals such as silica gel, silicic acid, silicic acid gel, silicates.

Talc, kaolin, Atakure 1 limestone 5 lime, chalk.

Agulose granular soil 1 Lime trade yellow clay, '16 earth, dolomite, silica earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic W fat, fertilizer such as ammonium sulfate') A, m
[Ammonium, ammonium nitrate.

Urea and other physical products such as grain flour, bark, wood and walnut shell flour, textile flour and other solid carrier materials.

The use form contains active substance o, 1 to 95%, in particular 0.5 to 90% by weight.

Examples of formulations are as follows.

1.903 When the active substance Al at the edge is mixed with 10Nf part of N-methyl-α-pyrrolidone, a bath liquid is obtained which is suitable for use in the form of very small drops.

■, 10 parts of active substance @A2, 90 mthltts of kijirole, 6 parts by weight of an adduct product obtained by adding 8 to 10 moles of ethylene oxide to 1 mole of olein i[-N-monoethanolamide, dodecylpenzole 2 parts of the calcium salt of sul7onic acid and 40 moles of ethylene oxide are dissolved in a mixture consisting of 2 parts by weight of the addition product in 1 mole of castor oil.

m, 2oz = parts of active substances, 60 parts of cyclohexanone vinegar, 30 parts of isobutanol, 5 mjt parts of an additive product of 7 moles of ethylene oxide added to 1 mole of octylphenol, and 40 moles of ethylene oxide, 1 mole of castor oil. OIV dissolved in a fart θ monolayer consisting of 5 adjunct products added to , 20 Jyuto's effective 'WV Jitsuya 2 was added to cyclohexanone 25, and Natsu 2 was added to cyclohexanone 25.
A mineral oil fraction of 65 M M MIS at 10 DEG to 280 DEG C. and 40 moles of ethylene oxide are dissolved in a mixture consisting of 10 parts of the additive product '+9IJ added to 1 mole of castor oil. By pouring this molten g into 100,000 ml of water and finely distributing it, an aqueous dispersion containing 0.0211 L of effective Wl content is obtained.

(2) 80 parts by weight of the active substance A2 were mixed with 3 parts by weight of the sodium salt of diisobutyl-naphthalene-α-sulfone, 10 parts by weight of the sodium salt of ligninsulfonic acid from the sulfite waste solution and 7N parts of powdered silicic acid gel. Mix thoroughly and grind in a hammer mill.

Vl, 5 parts by weight of active substance A1 were added to finely granulated kaolin 95
Mix intimately with heavy weights. A noodle spray containing 5% of the active substance is thus obtained.

vl, 30 Jidōto's effective q9/J pawnshop 11 is mixed with honeydew with powdered silicate gel 92i * jt part and a thigh joint made of paraffin oil 8N soybean coated on top of this silicate gel. do. Thus, the load movement has good layer contact! +
/I actual formulation is obtained.

Vllll, 20 summer effective supplies store 5, dodecyl penzole sulfonate calcium F4' 2 N
Jt m, 1m MJj Alcohol-Polyglyfurney f A/ 8 Teidou s.

Phenolsulfonic acid - draft - 7 It is mixed with 2ffKffi parts of the sodium salt of omaldehyde silk compound and 68 parts of baraffinic mineral oil. A stable oily dispersion is obtained.

Application can be carried out by pre-emergence or post-emergence treatment methods. Is it effective after germination of undesirable plants? ! It is advantageous to apply the substance I or the agent containing the active substance after the plants have germinated. If the active substance has low compatibility with a particular cultivated plant, the herbicide can be applied to the sensitive leaves of the cultivated plant using a rusting machine to avoid contacting the sensitive leaves of the cultivated plant as much as possible. Post-directed spraying (lay-by method) can be applied to reach the unfriendly fruits of other plants growing underneath or the exposed soil surface.

The application rate of the active substance is 0.025-5 ky/ha based on the science, target plant and growth stage.

The effect of the compound of formula I on the growth of other plants of the Poaceae family (Poaceae) and other plants cultivated by Mr. Hiro and others was shown in a heated experiment.The cultivation container had a volume of 300 d, and local rice soil was used as soil. A plastic yuzu drumstick containing loam sand having approximately 1.5% is used. Dividing other types of yuzu for testing, shallow < -1 <. In the sigma treatment method, the effective substance is immediately sprayed onto the surface of the castle. In this case, the active substance is dispersed or emulsified in a paddy field as a distributing agent and then dispersed or emulsified in a paddy field using a subdividing nozzle. fog. The amount of application is based on the active substance3. O1y/ha. After applying the chemical, add 1 ounce of water to the container to promote germination and growth.

The container is then covered with a clear plastic hood until the seeds germinate. This cover guarantees uniform germination of the Test 4114 products, as long as the Test products are not completely poisoned by the active substances.

For post-emergence treatment, 3 to 1
A test specimen that had grown to a height of 5 cm was adopted and the site was used. The rice, dice, and beets grown at the Kabutoga Shun site grow on the gold-crystalized cultivation soil. There is no need to be afraid of consequential revenge in order to apply blood and fruits. For post-emergence treatment, old,
f! : Select other plants grown in the same container, or use them as separate plants first. 2.3.
Transplant into experimental containers on a daily basis. Application rates for post-emergence treatment methods vary from plant to plant. This amount is effective @ 0
．． 125, 0.25.

0.5 and 1. okf/ha. In the post-emergence treatment method.

Do not cover.

Place the experimental container in the greenhouse. At this time, the temperature should be set at a temperature of 20 to 35°C for thermophilic plants, and 10 to 25°C for plants that prefer a mild climate. Indeed, the time is between 2 and 4'JJM. During this time, the plant's reactions to the individual treatments are evaluated. Evaluations are made at schools ranging from 0 to 100. In this case, 1
00 indicates that the other plants do not germinate, or at least the surface of the ground has died. represent.

'h1wJ used in the 'tnA'7 experiment consists of the following crystal phases: Oat (Avena fatua) +
Oats (Avena 5ativa).

Chard (Beta vulgaris) *Bromus tectorum
.

Himeshi/< (Digitalia sanguina)
lis).

Golden millet (Echinochloa crus-gal)
li) l dice (Glycine max,) *
Gossypium hirsutum
*Lolium multifloru
m).

Rice (0ryza 5ativa).

Cowpea (Phaseolus vulg, )
+Core 9 (5etaria 1talica) Sorghum halepense
) l Wheat (Triticum aestivum)
).

Corn (Zea mays) In testing the herbicidal effect of pre-emergence treatment.

For example, compound? IA1', 2, 5.6. 10.13.2
0°22, 23. 24.25. 26.27. 32
．． 34.35 and 37 are active substances 3. Oky,/ha
It exhibits outstanding herbicidal activity against the diversionary herbaceous plant at an application rate of .

In the test on selective herbicidal properties in the post-emergence treatment method, 9 examples showed compound scores of 20.32 and 33.
．． 125 ky or 1. Oky/ha and 木ふ糾佾吻?
Conditioned to exterminate effectively. Similarly, is KA-8-吻6應22 valid? ! It exhibits good herbicidal activity against undesirable cultivars and other cultivated plants at 0.25 k/ha, and is compatible with wheat and rice. Compound points 32 and 33 have good compatibility with broad-leaved cultivation and other plants at an application rate of 1.0 g/ha of the active substance, but at the same time, they cause strong phytotoxicity to plants of the family Hematinaceae.

Uninvented compounds, taking into account their compatibility and the diversity of their applications, may still be used as weeds that are undesirable in a large number of cultivated plants, or in the cultivation of Paulowniaceae only if undesired in a particular situation. Can be used to exterminate. For example, the following cultivation I@other items apply: Onion (AAllu cepa) Binary 1 (AAllu cepa)
Ananas comosus ) Tenquin bean (Ar
achis hypogaea) asparagus (As
paragus officinalis ) Swiss chard (Beta vulgaris spp, altis
sima) Satojisha (Beta vulgari)
s spp, rapa) red sugar beet (Beta v
ulgaris spp, esculenta) Brassican
apus var, napus) Brassica napus (Brassica napus)
us var, napobra-ssica) napus var, rapa) brassy force
pus var, 5ilvest-r18) Camellia 5inensis
Safflower (Carthamus tinctorius)
) Caryaillinensis
inoinensis) Malpushkan (C1trus limon) Grapefruit (C1trus maxima) Daidai (C1trus reticulata) Japanese oak (C1trus 5insnsis) Coffee Tsuki [
Coffee arabica (Coffea can)
ephora + Coffeeliberica)
] Cucumis melo Cucumber (Cucumis 5ativus) Carrot (D
aucus carota) Elaei
s guineenis) Strawberry (Fragaria
vesca ) Soybean (Glycine max) Paddy rice [Gossypium hirsutum (Go
ssypiumarboreum Gossypium
herbaceum gossypiumvitif
olium)) Sunflower (He1ianthus annuus) Jerusalem artichoke (He1ianthus tuberosus)
) Hevea brasiliensis
) Large 9 (Hordeum vulgare) Humulus 1upulus (Ipomoea batatas) Japanese walnut (Juglans regia) Lactu (Lactu)
ca 5ativa) Lentil (Lens cul)
inaris) Flax (Linum usitatis)
simum) tomato (, Lycopersic
on lycopersicum) Apple M (
Malus spp, ) Chara mackerel (Manihot
esculenta) Purple Alfalfa (Med
icago 5ativa) Hatsuka (Mentha)
piperita) r Musa 5p
p,) Tabacum: l [N1cotiana tabacum (
N, rustica) ] Olive (01ea e
uropaea) Rice (Oryza 5ativa)
) Adzuki bean (Phaseolus 1unatus) Cowpea (Phaseolus mungo) Cowpea (Phaseolus vulgaris) Betrotherium cristium (Petr
oselinum crispum spp.

tuberosum) Spruce (Picea abies) Fir (Abies alba) Pine weave (Pi
nus spp,) Pishm sativum, Prunus avium, Prunus spp.
domestica ) Prunus dulcis (Pru
nus dulcis) peach (Prunus per
sica) Pear (Pyrus communis)
Currant (Ribes 5ylvestre) Hawthorn (Ribes uva-crispa) Castor bean (
Ricinus communis ) sugarcane (S
accharum officinarum ) rye (5ecale cereale ) rubber (8esa
mum indicum) Potato (8o1anu
m tu, berosum) Sorghum (8org
hum dochna) spinach (8pinac)
ia oleracea) Theobr
oma cacao) Trifo
lium pratense) wheat (Triticu)
m aestivum ) Vaccini
um corymbosum) Cowberry (Vacci
nium vitis-1daea) Broad bean (Vi
cia faba) Vigna sinensis (Vigna sinensis) (Vigna faba)
gna 5inensis (V, unguicul
ata) ] Grape (Vitis vinife, r
a) In order to expand the spectrum for 1.1 and to couple the synergistic effect, the cyclohexane-1,3-cyone derivative of formula 1 can be used with other herbicidal or growth-regulating active substances [many representatives of the group Can be mixed with and distributed together.

Examples of mixed components include diazine, 4H-3,1-benzoxazine bleached conductor, benzothiadiazinone, 2.6-
Sinitroaniline.

N-7 el carbamate, thiol calcmate,
Halogen carboxylic acids, triazines, amides.

Urea, diphenyl ether, doriazinone, uracil,
This applies to benzofuran conductors and others.

Furthermore, new active substances or drugs containing said active substances or combinations with other herbicides'e71: Other protection agents 9 For example, insects or germs It may also be advantageous to mix and apply the same with agents that control the genus. In addition, it is used to compensate for the lack of honor and weight, and the number of salt baths is already attached, and the sacrificial value is also low. You can also add

Continuation of page 1 Priority claim @May 25, 1982 ■West Germany (DE
)■P 3219490.0 0 Inventor Hart Ziegel, Federal Republic of Germany 6720 Schweier-Hansupurmann-Allee 5 0 Inventor Bruno Würther Federal Republic of Germany 6701 Oterstadt Rüdeigerstrasse 13

Claims (1)

[Claims] Formula (1): [In the formula. R' can be defined as one or more salt atoms, chain atoms, alkyl groups or alkoxy groups having approximately 1 to 3 carbon atoms, or phenyl groups. a cycloalkyl group capping 3 to 6 carbon atoms, or a chlorine atom, a bromine atom, an alkyl or alkoxy group having 1 to 4 1ilX2 atoms, respectively, or a phenyl group with 11 or more && A cycloalkyl group, a bicycloalkyl group, a tricycloalkyl group having 7 to 12 carbon atoms, which may optionally be or represents an ethoxycarbonyl group. ? represents an alkyl group having 1 to 4 carbon atoms, and the subscript represents an alkyl group having 1 to 3 carbon atoms. An alkenyl group having 3 or 4 carbon atoms. , 3 or 4
a halogen alkenyl or propargyl group having 1 to 3 carbon atoms and 1 to 3 halogen groups. (2J 2- (1-ethoxyamino-butyritene)-
5-(Cyclotochika-1,5-dien-9-yl)-cyclohexane-1,3-dione. mark) j! 811/I as stated in Clause 1 of Claim F. (312-(1-oxyaminobutyritene)-
5-(Cyclododec-1,5-dien-9-yl)-cyclohexane-1,3-dione. The compound according to claim 1. +4'1 formula; [in the formula. The loan is replaced by one or more alkyl or alkoxy groups, each containing 1 to 3 carbon atoms, or a phenyl group. A cycloalkyl group having 3 to 6 SS atoms, or a chlorine atom, a purple atom, an alkyl group or an alkoxy group having ~4 longitudinal atoms, or a phenyl group with one or more 11L atoms 7 to 12 (cycloalkyl group, bicycloalkyl group, tricycloalkyl group having any number of carbon atoms in IJ. Cycloalkenyl group, bidicloalnanyl group or tricycloalkenyl bt-coated). atom, methoxycarbonyl group or ethoxycarbonyl group. y represents an alkyl group having 1 to 4 carbon atoms, and y represents an alkyl group having 1 to 3 carbon atoms. alkenyl group having 3 or 4
represents a halogen alkenyl group or propargyl group having 1 to 3 carbon atoms and 1 to 3 halogen substituents. a) ammonium compound represented by the formula: Fe0-NH,, Y (wherein the rating is as above and Y represents an anion); or b) reacting the compound in the presence of a base in an inert bath agent, optionally in the presence of water, at a temperature of 0 to 80° C., or b) optionally present in the water bath liquid: FPO-NH
. It is characterized in that it is reacted with a hydroxylamine represented by the formula (in which the symbols represent the above) in an inert bath agent. A method for producing a cyclohexane-1,3-dione derivative. tj1 A compound of formula H is reacted with an ammonium compound of the formula: 0-N8Y at a pH value in the range of 2-8. Feature #'F Claim No. 1. A method according to claim 1. (6) Formula: [In the formula. One or more atoms are substituted by a chlorine atom, a bromine atom, an alkyl or alkoxy group having 1 to 3 carbon atoms, or a phenyl group. one or more substituted by a cycloalkyl group having 3 to 6 carbon atoms, or an alkyl or alkoxy group having 1 to 4 carbon atoms, respectively, or a phenyl group; Cycloalkyl, bicycloalkyl, tricycloalkyl groups having 7 to 12 carbon atoms. Represents a cycloalkenyl group, bicycloalkenyl group, or tricycloalkenyl group. The description refers to a hydrogen atom, a methoxycarbonyl group, or an ethoxycarbonyl group. y represents an alkyl group having 1 to 4 carbon atoms; and y represents an alkyl group having 1 to 3 carbon atoms. artenyl group with 3 or 4 carbon atoms, 3 or 4
A herbicide containing a cyclohexane-1°3-dione derivative represented by the following formula: a halogenalkenyl group having 1 to 3 carbon atoms and 1 to 3 halogen substituents or a propargyl group. (7), 2-(1-ethoxyamino-butylidene)-5
-(cyclododeca-1,5-dien-9-yl)-cyclohexane-1,3-dione. A herbicide according to claim no. 11rl Patent l featuring 2-(1-allyloxyamino-butylidene)-5-(cyclododeca-1,5-dien-9-yl)-cyclohexane-1,3-dione
The herbicides specified in the scope of the request. (9) Inert additive and formula: [in the formula. One or more atoms are substituted by a chlorine atom, a bromine atom, an alkyl or alkoxy group capping 1 to 3 carbon atoms, or a phenyl group. One or more cycloalkyl groups having 3 to 6 return atoms, or alkyl or alkoxy groups having 1 to 4 carbon-tooth atoms, respectively, or phenyl groups. A cycloalkyl group, a bicycloalkyl group, a tricycloalkyl group containing 7 to 12 carbon atoms, which may be mixed. Covering a cycloalkenyl group, bicycloalkenyl group or tricycloalkenyl group. Represents the oxycarbonyl group. ``ma'' represents an alkyl group having 1 to 4 carbon atoms, and ``ma'' represents an alkyl group having 1 to 3 carbon atoms. Artenyl group having 3 or 4 carbon atoms, 3 or 4
A herbicide containing a cyclohexane-1°3-dione b conductor represented by a halogen alkenyl group having 1 to 3 carbon atoms and 1 to 3 halogen groups or a propargyl group.