LT3198B - Substituted bicycloheptandione derivatives - Google Patents

Abstract

This invention describes new changed bicycloheptadione derivatives, which have great herbicidal activity and can generally be formulated (I), <IMAGE> where R1 means lower alkyl group, phenyl group, which can be changed, aralkyl group, which can be changed, or heterocyclic group, which can be changed; R2 is the same or different and means halogen, alkoxyl group, alkylyte group, alkylsulfonyl group, alkyl group, alkoxyalkyl group or alkoxycarbonyl group, and n is from 0 to 4; R3 and R4, the same or different, mean hydrogen or lower alkyl group.

Description

The present invention relates to novel modified bicycloheptanedione derivatives, processes for their preparation, and herbicides containing said derivatives which function as effective components.

Many species of herbicides have been introduced in agriculture and horticulture to control weeds and to avoid high labor costs for weeding, but in some cases the phytotoxicity of herbicides can damage the crop or cause herbicides remaining in the fields to cause environmental contamination.

It follows that chemicals that are highly effective and less harmful to mammals are awaited.

Known patents relating to compounds analogous to the compounds of the present invention include patents EP-137963, EP-135191, EP-186118, EP-186119, EP-186120, Japanese Patent Application Ser. Sho 62-123145, EP-278907, EP-268795 and EP-264737.

The compounds of the present invention are included in DE patent no. 3902818 (corresponding to GB 2215333 and Japanese Patent No. Hei 2-1422). However, the compounds of the present invention are not described in that specification.

The object of the present invention is to provide herbicides which can be readily synthesized industrially, which are in fact effective in lower doses, which are safe to use and which are sufficiently selective for cereals.

Substituted Bicycloheptandione Derivatives of Formula (1)

(1) wherein R represents a lower alkyl group, a phenyl group which may be substituted, an aralkyl group which may be substituted or a heterocyclic group which may be substituted;

R, the same or different, represents / halogen, an alkoxyl group, an alkylthio group, an alkylsulfonyl group, an alkyl group, an alkoxyalkyl group or an alkoxycarbonyl group, and n is 0 to 4;

n ³ 'r /

R and R 1 are hydrogen or salts.

the same or different denotes a lower alkyl group) or their

The aforementioned phenyl substituents are the same or different, hydroxyl, nitro, cyano, genalkyl, haloalkenyl, aralkyl, and heterocyclic groups, halogen, alkyl, alkenyl, haloalkoxyl, haloalkoxyl, haloalkenyloxy, alkylthio, alkenylthio, alkynylthio, monoalkenylthio, monoalkenylthio, dialkylamino alkoksialkiltio, alkiltioalkiltio, alkoxycarbonyl, alkilkarbonilalkoksilo, alkylcarbonyl, alkoxyamino, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl alkoksialkilsulfonilo, alkiltioalkilsulfonilo, alkilsulfonilalkilsulfonilo, haloalkylsulfonyl, alkoksikarbonilalkiltio, alkoksikarbonilalkilsulfinilo, alkoksikarbonilalkilsulfonilo, alkylamide and fenilaralkoksilo group which may be substituted, an aralkyl group which may be substituted, heterocyclic group which may be substituted and alkyl substituted with heterocyclic group which may be substituted.

Said non-cyclic groups may include pyridyl, pyrimidyl, thienyl, furyl, pyrazolyl, pyroyl, imidazolyl, pyridazinyl, pyrazinyl, indolyl and the like.

The compounds of the present invention exhibit high herbicidal activity in mountainous areas when applied to soil or plant leaves. They are very effective in combating different types of weeds in the highlands, such as the toad, the gypsy knotweed, the galen and the burbot, by spraying directly on the leaves of these plants. These compounds exhibit selectivity for certain cereal species, such as wheat and soybeans.

Some of these compounds have growth retardant properties on cereals, ornamental potted plants and fruit trees.

Some of them are highly selective for rice and have a high herbicidal effect on creepers, small-flowered umbrella plants, seedlings and Japanese parasols.

In addition to the above, the compounds of the present invention may be adapted to combat weeds in areas such as gardens, lawns, railroad slopes, empty plots, and the like. t.

In their composition, the compounds of the present invention can be obtained by the following routes.

Method of production (a)

(when R ¹ , R ² , R® R ⁴ and n has above specified 10th values, and Q is falling apart group) • In this process years compound i (I) are formed in response

Compound (II) in a solvent using 2 moles or excess of base in a temperature range of -20 ° C to the boiling point of the solvent for consumption. This temperature is preferably between 0 ° C and 50 ° C. The reaction lasts from 30 minutes to several tens of hours.

The leaving group may be halogen, alkylsulfonate and phenylsulfonate.

The bases used may include alkali metal hydroxides such as KOH and NaOH, alkaline earth metal hydroxides, tri- (C 1 -C 6 alkyl) amine, pyridine,

DBU, t-BuOK, Triton B, sodium carbonate, sodium phosphate and the like. The solvents used may be water, alcohol, methylene chloride, benzene, toluene, ethyl acetate, dimethylformamide, THF, dimethoxyethane, acetonitrile and the like.

Method of production (b)

Mono-substituted compounds within the scope of the compounds of this invention, other than those in which the alkoxycarbonyl group is in the fifth position on the bicyclic ring, can be obtained by the following reaction:

where r represents an alkyl group.

If these compounds have different substituents at the fifth position, as in the case of (I) 'or one substituent at the fifth position, as in the case of (I)', with respect to the cyclopropane ring, stereoisomers exist.

When (I) '' is obtained directly by the above-described preparation of (a), a trans form is generally formed.

In the synthesis (I), it is possible to distinguish between eis and trans forms. With proper selection of the methods of obtaining, (I) '' trans and eis forms can be obtained.

The parent compound and the compound (I) of the present invention have optical isomers and a large number of tautomers of the following forms may exist:

(wherein R ¹ , R ² , R ³ , R ⁴ and n have the meanings given above). All compounds of this form are included in the present invention.

If the compound (I) formed in the above manner contains a free hydroxyl group, the salts of the said compound, which are used in agriculture and horticulture, the enamines and their analogues, acrylate, sulfonate, carbonate or ether can be obtained.

The corresponding salts used in agriculture and horticulture include sodium, potassium, calcium, ammonium and similar salts.

Ammonium salts are examples of such salts in which the ion can be expressed by the formula N ⁺ R ^a R ^b R ^c R ^d (wherein R ^a, R ^b, R ^c and R ^d are respectively selected from hydrogen and in some cases _Ο χ _ ₁₀ alkyl groups may be replaced, for example, by a hydroxyl group). When any of R ^a , R ^b , R ^c and R ^{d may} in some cases be substituted by alkyl groups, it is desirable that that group has from 1 to 4 carbon atoms.

Suitable enamines and their analogs include those whose OH groups are appropriately converted into a group represented by the formula NR ^e R ^f (wherein R ^e may be, for example, an alkyl or aryl group having from 1 to 6 carbon atoms, which in some cases may to be substituted or, for example, a phenyl group, 0R ^f denotes hydrogen or, for example, an alkyl or aryl group having 1 to 6 carbon atoms, which may in some cases be substituted or, for example, a phenyl group), halogen or SR ^g ( wherein R ^g represents the same group as R ^e ) described above.

Suitable acrylate or ether derivatives include compounds wherein their OH groups can be converted into the groups represented by the formulas - OCOR ^h or - OR ^h , respectively (where R ^h is the same group as the R ^e group described above).

Suitable carbonate derivatives are compounds wherein the OH groups may be converted into a group represented by the formula - OC (O) NR ^{1 R]} (wherein R ¹ and R ³ respectively represents hydrogen or is the same as defined above and R ^e).

These derivatives can be obtained by conventional means.

The structure of the compounds of this invention is determined by methods such as infrared spectroscopy, nuclear magnetic resonance and mass spectroscopy.

The following is a detailed description of the present invention with reference to the following examples.

Example 1

- (2-nitro-4-chlorobenzoyl) bicyclo [4,1,0] heptane-2,4-dione. (Compound 1 - 97).

Dissolve 0.5 g (1.44 mmol) of 5-mesyloxymethyl-2 (2-nitro-4-chlorobenzoyl) cyclohexane-1,3-dione in 15 ml of ethanol, to which 2 ml of aqueous sodium hydroxide solution are added with stirring at room temperature. (Sodium hydroxide: 0.17 g, 4.31 mmol). The resulting mixture was stirred at room temperature for another two hours. At the end of the reaction, the solvent is distilled off. Dilute the resulting precipitate with 50 ml of ethyl acetate and 10 ml of water. Then dilute hydrochloric acid is added until the aqueous layer becomes acidic. The organic layer is washed with brine and dried over magnesium sulfate. The solvent is distilled off. The resulting precipitate is purified by silica gel column chromatography (eluent: chloroform). 0.38 g (86% of theory) of the product was obtained in the form of light yellow crystals, m.p. 132-134 ° C.

Example 2

3- (2-Chloro-4-methylsulfonyl-3-methoxybenzoyl) -cis-5-methyl-cis-bicyclo [4,1,0] heptane-2,4-dione. Compound 1-195.

1.19 grams (2.6 mmol) of 3- (2-chloro-4-methanesulfonyl-3-methoxybenzoyl) -trans-5-ethoxycarbonyl-cis-5-methyl-cisbicyclo [4,1.0] heptane-2,4- The dione is dissolved in 7.8 mL (7.8 mmol) of IN-NaOH under ice-water cooling. The reaction was then carried out at room temperature for 4 hours. At the end of the reaction, an additional 20 mL of ice water and 20 mL of ethyl acetate neutralized with IN-HCl were added with ice-water cooling followed by decarboxylation. The organic layer was washed with water, followed by brine, and finally dried over MgSO ₄ , and the solvent was distilled off. The resulting precipitate was purified by silica gel column chromatography (benzene: ethyl acetate = 5: 1). 0.29 grams of the expected product are obtained in the form of white crystals and m.p. t. 132-135 ° C. The resulting cis and trans forms were synthesized in the manner described in Example 1 and examined by nuclear magnetic resonance.

Tables 1-3 show optional examples of the corresponding compounds, together with the previously obtained compounds.

R ^x , R ^Y and R ^z are substitutes in the corresponding tables. The trans and cis forms given in the Physical Properties section are spherical configurations of the fifth position of the bicyclic ring and the cyclopropane ring.

(will)

Table 1.

Structural formula:

Table (continued)

Physical properties 1st 128-130 ° C (trans) m I mm rn mmmmr \ H | -l tiM »- _Γ * • H * T * hr *» Ή N. ' | JL | | JL | pl μ] _ | Μ-, Ml U-4 CN uuuuuuuo CNCNiMOJOJCNCSIrn OOOOOOOT ωωωωωωωΛ „1 1 1 1 1 1 1 | re u ....... i 9 ffi <n 'u oooo uouo Toj u oooo ooww • ΓΊ <N CN <N <N <NCN <NCNCN J? ω no Ιΐΐΐΐΐχχ H ioo ω ουοοοοου X Λ III 1 1 1 1 1 1 1 1 97 sr sr sr nroronrococom 'm III 1 1 1 1 1 1 1 | rr! σισισιηησίΓηιησισίΓΠίΌΛ 1 ZjhhhfLKKEffiffiKKKK MOUOOOU OUOOOOUO PQ 1 1 1 1 1 1 1 1 1 1 1 1! 1 ICNCN <NCM {NCNOJO] C \ J {N {N <N {N {\ J {V <n iiiikiikiūkiiuiiii m Pi m II ISIIIIIIKIKI-IUII c CN Pi m She's 5 ω. O I - U 1 - - 'm m LT) O o I I 1 - II II O O v) m c C 1 1 - - 1 1 1 1 1 1 1 1 LO i — ILDrHIII Well o r-ι <\ i <n sr m <0 rHOjnsrin ^ Or'OOCni-li-li-li-IrHrHrH 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

Table (continued)

m - <D Λ > (1 co m -0) c Ή X r- | N Ή of those powder m.p. 178-180 ° C (trans) E X • H '-' · Η r- nf χ kkk χ k kj? uuuuuuu _m <? r ⁰³ ™ CM CM CM c \ l CM CM J? JT UUS AND ^1- IOOOOOOO K ffi CM CM U υυωωωωωωω-πωυοοο liiiiiii to U o co co ω ω 'cr'cr'cr ^ T'cr'cr ^ r' ^ i ^ iiii ι i 1 | | | 1 II 1 I · 7Γ ST ST sT ψψ ^ 'τ'ψψυυυυυυυυυυυ ^{1 1 1} ι ι I 1 1 1 1 ι ι 1 ι 1 ι (nfOrOfOfnmmmmrOmfnmrOfn ^ ^{1 1 1} llll 1 ll ι ι l ι li ►JT JT ¹ J? IJ ?, J? UJ? 07 {nfncninm {OfO (O THOUGHNOWvuooooooou J, J, ^{1 1 1 1 1 1 1 1} lil 1 1 1 CNCmICmICNCmICmICNCmJCNCmJCmJCmJCNCNCMCN sr et n m D c CN n 5 n O K - UI— m m - 'LO O o K K 1 - II || o o m m c c II <<- llllLDr-ιιη ^ ΙΙΐιιιιιι (d 2 f ® 2 2 ^{H r} ' ^m O c4 Γ \ | -igic-icNnjcNC'jcsjcNęNCNCNiMnfncn l 1 1 1 1 1 1 1 l | ι | | ι ι i ι-II-IH-II-II-II-1 MH || —1 | —II — II — ΙΜΙ — II — IM

Table (continued)

Physical properties M.p.151-3 ° C M.p.77-8 ° C (trans) 1.t.177-180 ° C (decomposition) ε X -H r ~ - -r-) et - mm m r- skmk et • H r) r) cm m 31 „~ CM CM UOU Ά J? QQ CM CM Csl Λ tt ω ω OOO χ r j r j j _m iiu ω m ω rji ιγγγγ UOOOOOOO i ψ -i ¹ iiii ωωωωωωωω '® S rj rj r r r r 1 1 1 1 1 1 1 I TVVVVVV ^{1 1 1} ' ¹ ' * 1 1 1 1 1 1 1 1 fOcocofnrommcO lilllll KKKWWWWWHrHrHrHHHHH υυυυυυυυυοουυυου 1 1 1 1 1 1 1 1 i 1 1 1 1 1 1 1 (NCMCMCMCMCMCJC'CMCNC'C) et m et Oh K O ί-C fC X X m ps m K t-H FiH hrt FfM t-rl FjH Hrt r \ FrH Fr-t Frt Fi-t Frt Fy-I »- »» -H bH b-M FM FM FM FM b-M O FM FM FM FM FM | JL | bM b ^ M c m ™ y Et u et u I - m m '' LO O et et i <ii U U LO LT) g II · · - ' 1 1 1 LO t — 1 LO t − 1 1 1 1 1 1 1 1 1 1 d 2 m'rt ^, iOLO> oocnorHC \ ifO'TLr) LO> oo cofocnnmnrosrsrsr'ir '^ rsr' ^ 'rsr 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 F1 Fl F11-1 HH FII-1 Fl F1 H F1 H FII-II-1

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m it m 2 O CN o u O CN CN co | O O ω I ω | v rH 1 • ST 1 1 m K r- 2 cn cn m m 2 u CN CN m 2 o CN o u O i-1 O o O ? ? co u 2 φ co ro | co Λ sr l-1 • —1 1-1 1-1 i-1 i-1 i-1 o I O I o | u u o u CM CM CM CM CM CM CN

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Table (continued)

CN 0Ί m 2 U CN n cn 2 o 2 2 o 1 O 1 m m * LO O cn cn LO o 2 2 1 K II 2 2 1 II U U LO UO G U U LO uo 'G 1 1 *. - ' 1 1 K LO l-1 LO rH 1 1 LO t-1 LO , —1 1

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ΟΊ O rH CH CO LO LO Γ- 00 OO O rH CH CO | LO | UO J uo | UO | LO I LO I LO I ΙΟ I LO I LO AO LO LO LO LO HH HH HH 1-H HH 1 1-H 1 1-H 1 H 1 H 1 H 1 HH 1 H 1 H 1 1-H 1 H 1 HH

Table (continued)

Physical properties m.p. 46-8 ° C ε X co K u CN O 0Ί if) ω kk jp | O CN CO OOX 1 Γ-4 ΓΊ • -m CN CN Γ) σ, υων] θθθ | ffi ι ι o ω φ cn J? u '' i H zN ii «T Ό ¹ ν 'Π U <\ inm 1 1 1 1 a J? KKKHHHHU S _m ουυουυυο y ¹ jp ι ι ι ι ι ι ι τ Λ μη ωωωηωωωω ι m SI 1 1 1 1 1 1 1 OU CNCNOJiNiNOJCMCNCNCNCsi a aoo ooooooooooo uNoNCNCNC Λ ffiKKKEKKffittffiKŪlttlIlCcIK tn> oh χκκκπακκκκκκκϋΐ-κκκκ c CM Oops m m O m a ii u u β 1 i 1 1 1 1 1 1 LO rd 1 1 1 1 1 | | | (0 2 ΐΌ '^' η-οοσίο, -ίΓΜοο ^ Γΐη'Χ'Γ-αοσϊο ΌΙΟΙΟΙΟΌΓ'-Γ-Γ— [- ^ {--- (- (- [-. r - r— m) 1 1 1 ........ 1 1 1 1 1 HHHHHHHHHHHHHHHH

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Table (continued)

X m K O CN ι-1 υ O u J o to I sr 1 1 sr I 1 sr I 1 Cn 1 cn 1 n K sq K u o u Q. u Q. T cn 1 T CO 1 T co I 1 CM 1 CM 1 CM O O o 2 I X I | CM CN CM

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Table (continued) m

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Table (continued)

Physical properties powder (trans) E X O Ή m O you o L? u O u Q Q u e ^υ u υ L? "Ό; OO 33 K <nm cn m 2 / // 'new to you t? te te rH 2 omuuoo Siuuuuuuoooo ^ St ^ '- r.' /. Done ^ 5 = {£ ί5? 9ΐ ^{υουυυυ (} ~> υυυυ ΟΟΟΟΟωωωωωωωωωω ΤΤΤΤΤιιιιιιιιιιιι ¹ 1 1 1 1 1 r 1 L / L / L / L? 'N CN oi oi nu η h HH? H CMCNCMCMCMf \ I {\ IC \ l {\ l <\ l (NCMCMCNC \) CM m LCH teeteetetetetetet n 07 rc COOPERATION OPERATIONS c <4> oh 07 07 KW V - i _ K lo oo Si! L ° KK 1 £ c, uu to ^{1-1 1 1} iiiiiiiiii ιη Λ lo (0 S ClVLO '^ r-'OOC'IOi — ICMCO ^ m'Ot ^ OO rjr-ji-l - l ^ li-4r-l {\ <NCMCMOJCNCslCsJ (N ^{1 1 1 1} 1 1 1 1 ll 1 1 1 lii mhmmhhhhhi-ihmhhhh

Table (continued)

Physical properties m.p. 98-100 ° C E X 1 i — 1 LO r — 1 UO KJ CN -H U ω O 0 O <ng U> 1 - υ r, Ό j? o et> J?, /? G? Λι-Ii-tr-Ii-IHi-IOO · —1 Λ * H SOUOUUOOO- LJ LJ NU CsICMCMCMCMCMCMCslt- ') OO ft ω κκκκκκκκκκ τ9- · ^ </ ΧΓυυοουυοοοο Ul μ.L, UM. JCM (MCsJ (NCM <N υυυυυοοοοοοοοοο ωωωωωωωωωωωωωωω 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 CNCNCNCNCNCNCNCNCNCNCNCNCNCNCNCNC 1 1 1 1 1 1 _o ^u NOICN (N {NNCS | {M (\ (NM (NM (MCMtM 'SH et K a cn m m K K c CM rn m U m U Y m - 1 - U 1 - LO O m m LO O - II K ffi 1 »II LO C U U LO LT) c *> II N fc. v-1 1 1 1 1 1 1 LO T — 1 LO Γ — 1 1 1 1 1 (i.e. s ChOi-ICNCO'rtOlOr'OOOlOi-IC-JfO cMnmconntomnnn'Lr ^ T'T ^ rl-1 * —Ii-Ii-ll-Ii-Ii-Ii-ll-Ii-Ii-Ii-Ii-Ii-1 I —1 1 1 1 1 1 1 1 i 1 1 1 1 1 1 1 1 — ll — II — II — II— | In — ll · —II—) | —11 — II — ΐμ_ || _ || _ || _ |

table (continued)

n (D Λ > (0 co co d) C • H • H N • H et et 2 υ 2 d et m 2 1-1 et 2 1-1 O υ 2 υ U I O I ω | O | o I co co e X you are o CO 1 m E U 1-1 u 1-1 p 1 Ct 2 co 1 m 2 co 1 (Ώ 2 co 1 re 2 et 2 co 1 m 2 co 1 m 2 et 2 U CM 1 et al u 1 et al u kO kO kO kO U O U U U U O O o o 1 et 2 O O O O co co co co co co 2 2 2 2 Id CM 2 CN 2 CM 2 CM 2 CM 2 CM 2 CM 2 CM 2 CM al CN al U 1 O U | O U O | O U U U O U O U υ u CN CN CN CN CN CN <N Λ CN CN CN CN CN CN 1 CN 1 CN co (0 2 (D 0) co to m CO CO CO co to CO CO CO co co co co fO (0 (0 aj Π3 <C5 <d (0 oh ed <d (U cd cd u cd > N G c G G C c C C G G c c G G G G • H ♦ d • d • d • d d • d • d * d • d • d • d 0 2 T! 2 2 2 2 2 2 2 2 2 2 2 2 M • H • d • d • d • d • d • d • d • d -G • d • d Q) P M G G G G G G G G G G G G G G -p • H • d d • d d • d • d • d • d d • d • d (D 07 I a 1 a To 07 1 07 07 I a a a a a a a a m n n co co co co 00 co co co co co 1 co 1 co 1 co 1 co * r oh Ct 2 et 2 et 2 et 2 co 2 m 2 et 2 m 2 et 2 et 2 et 2 et et 2 et £ U et al et al u U U U U O U U U U υ u U u u u et Oops et K m 2 n 2 n 2 m 2 m 2 et 2 et 2 et al et 2 et 2 et 2 et 2 et 2 et 2 et al u U U U U U U υ u O υ U O O U u C S— * et m et et O CM Oops '' «M * 2 2 2 2 II υ U U U c 1 1 1 1 'S LO LO LO LO 1 1 1 1 1 1 1 1 1 1 1 1 (Ό v LO CO Γ 00 σ o d CN co M ¹ 2 co 00 P ΟΊ σι O O σ σ σ o o O o o O o o o 2 d To 5-1 | d 1 t-1 | d | —1 | t-l To CN | CN CN CN CN CN CN CN CN d H Id Id Id H d d d H d d d d 1 d 1 d d d d Id Id Id d d d d d d d d d d

table (continued)

tn • (D t! > 1 > tn tn • <1> G • r-i λ: • H N • H t) cn 1-1 cn m z o u z t: i-1 u CN cn 1 u u u o Z z IO o to cn CN CN cn u o | CN CN en Z Z Z Z CN CN ε m Z K z l-1 z u u u U O o cn X m u u υ u u o cn tn cn cn cn z u i-1 o o Ί> kO LO <0 LO LO co to co LO LO 1 1 co 1 1 1 1 1 1 1 1 1 1 1 <0 <0 CN m m ΓΌ cn m cn cn cn cn cn cn cn 1 1 m Z m Z Z m Z z z Z z Z Z z z Z U I u u o | u Ό u u u u u u o u u U CM Λ Λ CM Λ Λ CM Λ Λ CM CM Λ Λ CM CM CM tn (0 'ύ tn tn tn tn tn tn cn tn tn cn tn tn tn tn tn tn (U <u <U a) <Tj ftj (U you to <t) (0 <u (0 to to > KJ c c c c c c G G G G C G G G c G • r- | • H • H • «—1 • H • H • H • r- | • r-1 • r- | ♦ rH • Γ-Ι • H • H • H • 1-1 τί Ό Ό Z τ) T! τ) Ό T) τί T) t) Ό τ) τ) ts • H Ή • H • H • H • H Ή • H • H • H • H • H • H • H • H Ή cu G G G G G G G G G G G G G G G G Ή Ή • H • H H • H Ή Ή • H • H • H • H • H • H • H • H (D z I CL CL 1 CL CL CL CL | CL CL | CL CL CL CL CL CL CL Z n co n ro 00 ro 00 00 00 co 00 co co co co co cn cn n cn cn cn cn cn cn cn cn cn cn cn cn cn z Z z Z z z z Z Z Z Z Z Z • Z z z z u u o u u u υ u u υ u u u u υ o cn m m n cn cn m cn cn m cn cn cn <n m cn cn et z Z Z m m z Z Z z z Z z K z z u u u u u u u o u u u U  u υ u u c o CN lt Z 1 1 c 1 1 1 1 1 1 1 1 1 1 1 1 1 1 σι o t-1 CM ro sr LD co r- co σι o t-1 CM co sr μ o 1-1 t-1 r ^- 1 t-1 1— f t-1 i-1 r-1 5-1 t-1 CM CM CM CM CM Z CM Os] CM CM CM CM CM CM I CM I CM CM CM CM CM CM CM M I-f H H H H H H Hl H H H H H H H M l 1-1 H) i-i M 1-1 1-1 1-1 M M H M M 1-H 1-1

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t-1 CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CO (0 T5 (D CO CO CO CO CO CO to CO to CO C0 to CO CO CO CO (fl (fl (fl (0 rt rt (fl (fl (fl (0 (fl (fl (fl (fl (fl rt > N c c C C G c C C G C C C c C C c H • H -r4 • H • H • H -H H • H • H 0 Ό Tfl Tfl Ό Ό TS TS TJ Tfl TS Ό G • H • H • H • H • H • H • H H • H • H • H • H H Φ H H H G G G G G G G G G G G G G + j • H • H • H • H • H • H • H Ή • H • H Ή • H Ή • r | Φ E 1 & t & J a a & E 1 E E E E E E E E E m co n co co co co co co co 00 co C0 co CO ro t co ΥΓ 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 n 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 C CO co Π0 CO 2 2 2 2 2 O υ O υ 1 1 1 1 1 1 1 1 1 1 1 1 t-l t-1 t-1 r-l σ O r-1 CM co sr LO LO r- 00 σ o t-1 CM co v μ CM co CO CO co co CO CO co co co LT v LT v = T 2 C l-1 J t-1 | t-1 J t-1 t-1 t-1 t-1 t-1 t-1 t-1 t-1 t-1 t-1 t-1 t-1 H 1-1 H H H H H H H H H M H l-l H I H t-l t-H M t-l t-i 1—! t-l 1-1 l-l t-1 l-l l-l t-l M I-1 t-l

table (continued)

co • 0) t) ί> 1 > (U co co • Φ c • H Λ! H N • i-1 A CO m No. i-1 m O | O l-1 co co 1-i o No. i-1 u Ed No. υ ω U u kO co 1 u U 1 i 1 1 co o CO ro CO kO co co 1 CM CM CO No. e 1 1 1 1 No. No · No. co No. No. No. rN Z U X co co n CO co o o o No. O U U U U O 1 Ed No. No. No. No. CM CM CM O 1 1 1 1 1 ο υ U U U O O O O co CO co CO co co ο o co co CO co co co co 1 1 1 1 1 1 CM CM CM CM CM CM CM CM CM co co (O (O co No. No. No. No. No. No. No. No. No. No. No. Ed No. No. No. No. υ 1 U O O U O O U O U U o U U O O (Ν CN CN CN CN CN CN CN CN CN CN CN (N CM CM 1 CM co G xi φ C0 CO CO CO CO CO CO CO CO CO CO CO . co m co co G G G G (0 G G (d <d G G G G G G G > N C C c C C G G G G G G G C G G G • Η • H • H • H H • H • H • 1-1 • r-l • H • H • rl • r-l 0 χ) X) xs X) X) X) TS XI XI XI XI XJ XI X5 XI XI μ • Η • H • H • H • H Ή • r-l ·· —1 • H Ή • H • H • H • r-l • H Φ Η G G G M G G G G G G G G G G G j_> • r — 1 • H • H • H • H -H Ή • H • H H • H • H H • r- | • H φ α I & h A g h h z g a a A A A A A No. co co CO co co co CO co co co ω co co m 1 ro 1 co τ No. Κ No. No. No. No. No. No. No. Ed No. No. No. No. No. No. No. m (i.e. SC No. Z No. No. Z No. No. No. No. No. No. No. No. No. No. c co m m m CO CO CO CO CO co CO co CO CO ΰύ No. No. No. No. No. No. No. No. No. No. No. No. sd No. No. No. U O | O j U | U | U | O j O J O 1 U | O U u U U u γ-1 1-1 i-1 t-1 i-1 r-l i-l , - | 1-1 1-1 I-1 i-1 i-1 i-1 i-1 1 i-1 tn co θ ' OO σι O i-1 CN co sr LO co r- 00 σ O G 'J' sr N ¹ m LT) m lo LO LO LO LO LO LO co Ζ i-1 Γ-Ι | r-4 i i-1 1 Ί — 1 J i-1 I i-1 I i-1 I i-1 Γ-1 r-1 rH T-l i-l 1-1 1-1 H 1-1 t-l HH Hl H Hl l-l H H H 1-1 l-l 1 l-l H 1 M H H H M H H M 1-1 M Hl H H l-l l-l l-l Hl

continuation) • e;

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ω s 3 • d) 3 S Λ G G + to D > Π5 ω , —T cP sr ω o CM kO • φ i-t c • H λ: J 4-J • d • d N co CO Ή P 2 fe t t d l-1 i-i after co PO PC i-1 o o PC PC l-1 u 1 kO u u u o PC PC ω o CO CM CM PO o (J 1 CM CM co PC PC PC PC CM CM ε m PC PC PC d 2 o υ υ u o O PO X PC u o o i u I u u u o co co co co co 2 υ 1 i-1 u 1 LO LO LO LO kO LO kO kO kO kO kO ω 1 1 1 1 1 1 1 1 1 LO LO CM ro CO co CO co co co co co 1 1 PC PC PC PC PC PC PC PC PC PC PC PC PC 2 2 2 o i u t u 1 u I o o u u υ υ υ u υ O u U CM CM CM CM CM CM CM CM CM CM CM CM CM CM 1 CM 1 CM CO <d Φ CO CO CO m CO CO co co CO CO CO co co co W W id rd (0 to (0 id (0 (0 <d id (d rd (d (d (d fd > N c G C C C c C c G c G C c c G c • d • d • d • d • d • d d • d • d • d G 0 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 d • d • d • d • d • d • d • d • d d • d • d • d Φ G G G G G G M s G G G G G G G G oh • d • d • d d • d • d • d • d • d • d -d ♦ d • d d) Qm I a i Pm 1 a I & 2 h a h h 2 a 2 2 h PC n co n co co co co co ro co co co co 1 co 1 co 1 co «R 2 PC PC PC PC PC PC PC PC PC PC PC PC PC PC 2 2 m 2 PC PC PC PC PC PC PC PC PC PC PC PC PC PC 2 2 c m m n co CO CO co CO co co co 2 PC PC PC PC PC PC PC PC PC PC PC PC PC PC 2 2 u I o I o I u I o υ υ u o u o u u o O U LO m LO to LO LO LO uo LO LO LO LO LT) t m 1 LC 1 LO σ o i-1 CM co LT LO LO r- 00 σ o i-1 CM s co o o O o o O O o o o rd rd d 2 σ> | ΟΪ J σ » j rd | I - Vol rd rd r "1 , -! »—1 rd d , —1 d d d d td d t-l t-l d td td td M M td Id 1 Id 1 td 1 d d M td t-l d td H H d td 1—) M td td Id d

table (continued)

to d) t! >, > (0 CO co • d) C • d 44 Ή N • H fcl 07 co et 07 et 00 U J O J , - | 07 07 Z 1-1 u et 1-1 υ z et u o co u u kO kO J 1 u υ 1 1 1 1 1 | kO o co kO kO kO kO kO 1 CN CN e l-1 1 1 1 1 1 et et et 07 et et X o 07 07 07 00 co 07 07 (J (J (J et υ υ 1 1 et et et et et et et CN CN CN u 1 co υ u u o u o o O O O o kO kO 1 o o o o co co co co co co co 1 1 07 07 CN CN CN CN CN CN CN CN CN CN CN 07 Cm Cm et et et et et et et et et et et et et et O I υ u O 1 u u u u u Ό o u u o υ u Csl Csl Csl Ch Csl Csl Csl Csl Csl Csl Csl Csl Ch Ch CSJ CH co (0 Ti Φ CO co CO co co co co CO CO co co co CO co CO co • H <0 (i.e. <ti (0 (i.e. (i.e. (i.e. (i.e. (i.e. (i.e. (i.e. (i.e. (i.e. (i.e. (i.e. (i.e. > N C c C it c it c G G G G c G G G G • H • H • H • H • H • H • H • H • H • H • H • d G o Ό Ti Ti T3 Ti T) Ti Ti Ti T) Ti Ti Ti Ti Ti Ti d • H • H • H • H • 1-1 • H Ή • H • H • d • H • «H • H • d • d -d d) s G G G g oh G G G G G G G G G 1) -d • H • d Ή • r-1 'D ·> —1 • H • d • H • H Ή • rH • d • d d) t g no no | no n no no no no no no no no no et co co co co CO CO co CO co CO CO CO co CO co 1 co 'T ie Z Ct et et et et et et et et et et et et et et 07 it Z Ct et et et et z et et et et et et z et et C o o CN See II C II G 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 co V ¹ Lithium kO Γ 00 στ o rH Csl co sr LT) kO r- 00 G rd , —1 rd rd t-1 rH r-1 Ch Ch Ch Csl Csl Csl (N Cs) Csl Z τ ^- I | 1-1 To , —1 J i-1 | t-1 | rH i-1 t-1 rH rH rH i-1 i-1 rH i-t rH H H H H H M H H M H H 1-H HH 1-H 1 HH 1 HH H 1-H 1— f hH 1-H M HH M 1-H M H HH HH 1-H 1-H HH

table (continued)

Physical properties ε X m mm cn t-ί? i2f ?? * ^ 5 Φ m K ud 5d {\ J O O / p K in 5d «U ac ™ υ o m <? ® u a / oi oi (J cn m cn m <N <\ j5dC) cncnO OOUOOEOiZhttKtJOOOO ωωωωωοζυοοοωωωωω i l l l l l l i i i i i i ιηΐΌΐηΐΓ) ΐηΐΓ) ΐηΐΓ) ΐηΐΌΐηΐΓ) ΐΓ> ιθΐΌΐο The hetero ring coconcocococAcricococnincAcoKitn (0 {ΰ {ΰπ3 {0 (ΰ {ΰ {0 (ΰ {ΰ {ΰ {ΰ {ϋ {ϋ (ϋί GGGGCGCCCGCGCGGG • jJ zd 'N Ή ^-r I H · ΗΉH) 'ΌΌΌτίΌτίΌ'ύτίτίτ! • d -d -d -d -d -d -d -d -d -d -d -d -d -d -d -d ddddddi-ii-idddddddd • d -d -d -d -d -d -d -d -d -d -d -d -d -d -d -d ........... IIIII CM CM CM CM CM CM CM {M CM CM CM CM CM CM CM CM cd ^^^ cncnmnDmmcofrjmfnfnrn GGGGGGGGGGGGGGPGGGGGGGGGGGGGGGGG uouuuuuuuuuouuoo n υυουυυυ.... c CN cnmcnmcnmonm FAQEffiKKK ouuoouuu I I I I I I I I '' f f I I I I i-1 i-1 r-i t-1 i-1 i-1 rH rH S m'nr ^ aocTiOrHCMco ^ rmcor-oocyio ^ Ο'Χϊ ^ Ο ^ Ο ^ ΟΓ'Γ ^ Γ ^ Γ ^ Γ ^ -Γ'Ι—> Γ'- 00 l l l l 1 1 1 1 1 1 1 1 1 1 1 1 ΜΙ — II-IMI-II-II-IMHMMMMMHH MMMMMMMMMMHMMMMM

table (continued)

Physical properties £ X m b? K -1 cn J. mrlri 3 rH U aC> —1 II UU ω UO ώ ώ ¹¹¹ 1 I 1 τ kO kO kO kO kO _m mm d iii ι i ac ac ac n Yb? B? B? BPb? B? b? OUO tense i ac ac ac ac ac ac ac cm cm cm cm kOUOUUUUUOOO t) ιοοοοωωωωωω cm m cm mm cm cm cm cm cm cm cm cm cm oacosxxacacacacacacacacacac ωοζοοουοοουουοου 1 1 1 1 1 1 1 1 1 1 1 1 inir) iniOM {\ l {N {M {kJ {N {kJMMMC4 (N The hetero ring toncotococococotomtotomcocom (ύ {0 {ΰπ3 {ϋ {ϋ {ϋ {0 {ϋ {ΰπ3 {ΰ {ϋ <ϋπ3 CCiCiCCCCCCCCCtCCSCC • H · Η Ή - «- Ί -H-H-H-H-H -H -H -H -H -H ^Γ H ^Γ ΰτίΌΌτίτ! Τ3τ! Τ5 ^Γ ύ ^Γ θτΐτί'ύ • H -H -H -rd -H -H -H -H -H Ή · Η -rd -rd · Η · Η Ή MU> - | UUkqi-lUMHUi-lU> -iįqU Ή Ή · Η -rd -rd -rd * rd -rd -rd -rd -rd -rd -rd -rd -rd -rd biibsbiącagazggcacaacagcag 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 CMrMOjmcoroncofOmnnmromn M ¹ oi n en m m ffi Oh 00 01 uuuuacacacacacacacacacacacacac n Oops D m m m m oo oo oo oo ouuuacacacacacacacacacacacacac c (N £ acacacacacacacacactcacacac.acacacac υυυυυυυυ.... I 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 τ-dr-di — IrdlOLOLOLOLOLOLOLOLOLOLOLf) No. T-dCMinsrmkor-oooov-iCkin οοοοοοοοοοοοοοοοοοσι <τισ »σι <7ισισι 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Hl-II-II-II-dl-II-dl-II-II-dl-dl-II-dl-II-II-1 bdl-dbdl —Dbdbdbdbdbdl — Ib-dl — Ihdl — Ibdbd

table (continued)

Physical properties E X un cn cn 2 2 ρί tn hĮ-. OO O ¹ 2 UD 2 A CN CD CN C3CNC \ 2OcNCN O CN mc \ l 02022WK000000202 coo20000cococococqcoo20 ^{1 1 1} 1 1 llll 1 llll 1 1 LO LO LO LO LO LO LO LO LO LO LO LO LO LO LO The hetero ring oooocncncntncncncncncocncncn {d {d {ū {d {d {O {ti {d {d {dfd {d {({({ ⁽ {d 5SS55 ^c : ^c : ^cccccccc ! gc G 3 3 3 J -j -H -h -d -H -H -G -H -H -H TJO'tn'OTi'OOOO'ŪTiTlOTl'b • H -H -H -H -H -H -GG -G -H -G -H -rd - G -rd -G GGGGGGGGGGGGGGGG AAA 'to' ^H ' ^d ' ^H · + Ή ąaaaaaaaaaaaaaaa ^{1 1 1 1} lll 1 1 1 1 1 1 1 1 1 CMCMCMCMCMCMOJCNCNCMCMOJCMCdCslCsl 2 222222222222222222 cn 222222222222222222 c <N ^ nncncncncncncncncnncn 2 22222222222 ooouoooooooo .... ^{1 1 1 1 1 1 1 1 1} 1 ^{1 1 1 1} 1 IrdrGrdrdrdrdrdrdrdrdrdrdrd No. covtOLOr'OochOrdcNnv'LOLor ^ co concofofocofovv'vv'vv'v'v'v ¹ i ¹ iiiiiiiiiiiii HHHHHHHHHHMtGHHHH ΜΜΜΜΗΗΙΗΗΜΜΗΙΗΗΙΜΗΙΗ

table (continued)

Physical properties ε X et et et et Pi Pi et lo · ψ * EP Pi OOJ? 2 m 2 ™ OO O ω vp 2 _υ 2 UO ω <? et CN CN d LJ CM CM LJ CM Ct CM et CM CM Pi 2220000002022220 000ωωωωωω020000ω IIIIIIIIIIIIIIII 2222222222222222 The hetero ring mcommoiwmwtn Mrawno3m «<0 <ϋ <ΰ {ύ <ϋ <ϋ {ΰπ3 <ϋΓβ {ϋ {ϋ (ϋ <ΰ {ϋ <ΰ CCCGCCCGGCGGGGGG Ή -G -G -G * G -G -G -G -G - G -G -G -G * G -G -G 2222222222222222 G -G -G -G -G -G * G -G -G * G -G * G -G -G -G -G GGGGGGGGGGGGGGGG G -G -G -G -G -G -G -G * G -G * G -G -G 'G -G -H aaaaaaaaaaaaaaaa I I I I I I I I I I I I I I I I CMCMCMCMCMCMCMCMCMCMfMCNCMCNCMCM • ^ r 2 feed the feed the feed OOOOOOOOOOOOOOOO et 2 ethetetetetetet et et et et 000OOOOOOOOO _; OOOO C CN Pi to feed a feed κκκχκκεκλκκκ ii oooooooooooo c 1 1 1 1 1 1 1 1 1 1 1 1 - 222222222222 1 1 1 1 G S 0 ^ 0 ^ 22 ^ 20 {- OOOOi-1 (22 ^ ¹ > ^ 222222222200000 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1, HHHHHHHHHHHHHHHH ΗΙΗΙΗΙΗΗΗΜΡΙΗΙΗΜΜΗΗΙΗΗΙ

table (continued)

CM

Physical properties X CO CO -rH -Λ lO CO (O Ul Ul, η MH In-In-t oo P? Z m Z ci uu Οω '^ Ζυκ ^ ο o ω - jr 7 oniz ^? Ί?: ^ ^{Οοοοοχ;} οζζζζυ οοοωωωωωωο ^ ουυοω ^{1 1} ι ι ι ι ι OL OL OL OL OL OL OL The hetero ring cootoLocococoonooonototo S5555SS ^GCCCCCCCC i 'tdid' ^H ' ^H ' ^H · ^Η ' ^H ' H -H -H -H -H -H ΖΖΖΖΌΖ'ΰτίτίτΙτίΌΖΌ'σΖ i] T ¹ T ¹ T ¹ ' ^H ' ^H ' ^d ' ^{H - H} ' ^H -H -H -H -H -H' to 't' t ' ^H ' ^{H -r4} ' ^Η -H -H -H -H -a -H -H -rH -H ^{1 1 1} ι ι 1 l 1 ll 1 1 1 l 1 1 CMCMCMCMCMCMCMCMCMCMCMCMCMCMCMCM 'T (X zzzzzzzzzzzzzzzz CO & zzzzzzzzzzzzzzzz c Csl Oops zzzzzzzzzzzzzzzz ουυουουυυυουοουυ to L ^{1 1 1 1 1} ι ι ι ι ι ι ι ι i lOlOlOlOlOlOlOlOlOlOlOl060606060 No. O rH CM CO V LO 60 rHCSJC0 <šrLO6O> 00 ^ rHrHrHrHrHrHr-H 1 1 ^{1 1 1} lll 1 l 1 l 1 lll 1 ηηηημι-ηηηηηι-ηι-ιι-ηι-ηι-ηι-ηι-η HHM -1 -1

table (continued)

Physical properties ε X m σι m σι lo rr! it it mm j? it m it m υ u j? it m it ® U it ~ O O ω «O it. * U CN CN (_) CN 0Ί {N m CN CN 35 LJ cn cn U oooooitozitititooooo ωωωωωοζοοοοωωωωω 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 LDmmmmLOLOinLommmLnLnmm The hetero ring mmranrarammoj-o -rararannco <d <ū <ti {0 <d {d <TJ {fl <ū <0 <drd <0 <0 <d <d GGGGGGCGGCGGGCGC • H Ή -G -G -G * G -H -H - H * G -G * G * G -G * G -G 73737373737373731373730373731373 • G -G -G -G -G -G -G * G 'G' G * G * G -G -G -G GGGGGGGGGGGG GGGG -G -G -G -G -G -G -G 'G -G * G * G -G * G * G * G * G 1 1 1 1 I 1 1 1 1 1 1 1 1 1 1 1 CN (NCN (Nf \ JCNOJCNCNf \ J <NCNfNC> JCN (N vr it ttttititttEtititKititEt'ititEiG cn Λ »—I— · h ^- · h · hm M hm hm hm hm hm» T- · · —r * hm hm hm hm hm HM hM {M | M tM {J-4 »M In-L1 {M Uh Ml 'HM HM HM HM c CM oncncncncncncnmO O κ m it tt it tt it tt n ii υυουυυυζζ c 1 1 1 1 1 1 1 I - ldldldldloldloloi i i i i i i i G Z [^ oocioiGcsicosrLntūr'-ooo ^ oTGCsi toGrGrGOJCNlCNCNCNCNCNCNCslCNCOCOCO 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 HGHHHHHHHHHHHHHHH ΜΜΜΗΜΜΜΗΗΜΗΗΜΜΜΜ

Table (continued) co

! T!

> 1>

(fl

CO co • Φ c

• H

-H

N

Ή

E

U

co υ L_i LO A Λ 1 00 C o CM CO x (fl G 0 0 Λ 2 2 CO 1-1 <—1 2 CM -G -G • -— u 1 00 Ch c-1 * CO m • co 2 U e 0 2 x 2 • G 0 0 2 • G • H u -G CO σ 1-1 co • co CO n n CO O 1 ! G E c 0 X X O co g co σ (fl (fl 1-1 r-4 g frt X sr LO G 73 X G φ 44 (fl 44 X 'U C 73 τ-1 i-1 2 2 X 1 — i m co 73 X G • 1 “1 __i X '—1 2 2 i-1 co G to G «—1  H -G • G co (fl (0 CO (fl (fl 44 G G 1 f 4 (ow G G G (0 G rt Ή Λί (fl 44 CO CO g 44 g CO 2 73 2 44 CO CO 0 0 • H CO • 1-1 G co rt CO G g > 1 g X 1-1 • r-1 G G 1-1 • H G T! c (fl U _θ Ο i— ^J Ό _o u G G u 0 G 73 73 n 44 73 44 G CM 0 CM 0 73 0 X X CO E co • G 2 LO LO Ch G 1-1 1-1 - 2 —- 1-1 CM 1-1 CM E t-1 2

E (N

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re

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υ

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07 2 U 1 2 07 2 U 1 2 07 2 U 1 2 07 2 υ 1 2 07 2 U 1 2 07 2 U 1 2 07 2 O 1 2 07 2 U 1 2 LO X 00 σ O CM m (U LO LO LO LO x X X r * · E CM | CM | CM CM CM CM CM CM 2 H) l-l 2 l-l H 1 l-l

180 C (decomposition) (will go)

-274 5-CH ₃ HH 2 -Cl-3-OCH ₃ -4-SO ₂ CH ₃ 1'2 Ca salt m.p. t. >

225 ° C (dec) (eis)

-275 5-CH ₃ HH 2 -Cl-3-OCH ₃ -4-SO ₂ CH ₃ 1'2 Cu salt m.p. t. 210-221 ° C (no sec)

Table 2. Structural formula. 1-hetero ring, . • V- Xm _ / _. ΥΧΞ -A

Table (continued)

Physical properties melting t.151-2 ° C (trans) melting t.129-132 ° C (trans) melting t.70-4 ° C melting 1.129-131 ° C melting tl40-2 ° C (trans) powder (trans ) powder (trans) melting t.115-7 ° C (trans) powder (trans) powder (trans) powder (trans) melting t.47-150 ° C (trans) melting t.163-5 ° C (trans) powder (trans) powder n _D ²³ 1.5842 s »m et zz o» co co U „► £ O ^{1 1} z? 9 zmu _m sr v * z 'OZ co et. , ¹ ? 1 IU cn r) ον r 7 n HJ? d ¹ V ¹ O m Z 9m OUUKŪJOCdi — ICOOOO · —1 r — 1 r — 1 {—1 zcocouucoęo i co co co o υ υ υ i ¹ iiii T iiiii | | i 'šr ^ srcnco ^^ co i ν' sr vvvv ¹ v 1 1 1 1 1 1 1 1 <? i | iiiii i ¹ dd J dd S kkk, k <N <NCs] {N {N {N {N (NC \ lCNOsl <N {M {M <NC \ Csl 'T ie zzzzzzzzzzzzzzzz 07 Cd ZZZZZZZZZZZZZZZZ c CN Z i? <N „OZO - / OUO £% gg £ MMJTS vm M ⁿ J d ¹ m 1 nn 30 32 30 I υΖΖΖΖΖΖΖίΟ'τ'ν'τ ¹ οοοίησοφουουυυοουυυ ii ¹ ·· ^{1 1} 'flower 1 1 iiii LOLn - iir). LnLnLnLnLnLr) LnLr) LnLni-ii-i Well C ~ CO (T) O i — 1 CH CO LT) kO r- · »ro r ~ o —j // I ^ OJCSICNICsICNCNCNCNCMCNCMCNCN ^{1 1 1 1 1} ll 1 1 1 1 iiiii μμηηηηηηηηηηηηηη

Table (continued)

Physical properties powder powder powder powder powder (trans) powder m.p. 152-6 ° C (eis) powder ointment melting t. 172-4 ° C (trans) Well the salt melts. mp.230 ° C (decay) (will go) Well the salt melts. mp 180-2 ° C (decay) (will go) Well the salt melts. mp 223 ° C (decay) (will go) powder (trans) xF JP JP ^m HH m H oo ac jp jp n m ^M jp u tb š cj% OKNUO 'G ip a ^m on, oj; j; h ac oki jp n ι ω oo S SGOTOiyUi sr · l Y x G κ 7 ac 7 υ ac 7 ι i 7 otfou'uiccu'ac jp β 'δ φ ΰ ι ι ι ι 7 ¹ ® ι ι' ι 7 ι 7 CM CM m CM 1 CMCMCMCMOOfn 1 fO 1 OOhO ^ OOOOiaC H CC H ZZUSUSOZZhU UUU 1 1 1 1 1 1 T 1 1 1 l ι 1 1 CNCNCNCNCNCNCNCNCNCNCN CN CN CN • T (i.e. acacacacacacacacacacac ac ac ac 07 oh acacacacacacacacacacacac ac e ac c cj; ie 07 m m 07 m O 07 O 07 co co m co ac ac ac ac ac 11 ac 11 ac ac ac ac ac new part u u υ u υ 1 1 1 1 1 - 1 - || | | | 1 — IH. — ii — ilOIlDIIlolo lo tn lo Well CNfO'Ttn ^ or-cDcnoHCN n sr m ιηιηιηιηίηιηιηιηΌΌΌ to co co <N <NCNCNCNCNCN <NCNCNCN CN CN CN 1 1 1 1 1 1 1 1 1 1 1 1 1 | 1-II-II-II-II-II-II-II-II-IHII-1 Hl H H

Table (continued) m

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• -P 4-) 4-1 d d • G <d • G CO -c — i d CO 0 d d 0 S Φ Φ g > 1 4J P kO T) i-1 d Ό -H • d After

K rd t — I O CM o u o 1 1 co l ΠΊ G ¹ G ¹ 2 1 1 υ CN cn 2 en 2 1 d O O ω 1 U ? υ ? 1 co G ¹ 1 co 1 00 I 1 CN CN Cm ' »—1 O O o O | s | 2 I 1 CM CM CM CM

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G 4-1 co 4-1 '- • G - υ υ O υ o - o o o o (j LO σ kO LO o 1 1 1 1 CM CO r- G < 1 LO σ 00 G * O G • d id i-1 i-1 σ • U • • 4-1 - 4-1 -P 4-1 4-1 • d • G (d • G • d • G • G CO • d to ω CO 0 i-1 0 0 0 0 e (D ε ε ε ε After • P After After After After T! <—1 Ό Ό τ) T) After • d After After After After i-1 S 1-1 l-1 i-1 i-1

CN

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m 2 U 1 LO m 2 O 1 LO m 2 U 1 LO 1 LO LO n 2 U 1 ! —1 n 2 U 1 LO l-SCH; m 2 U 1 LO cn 2 U 1 LO n 2 U 1 LO 2 υ 1 LO m 2 U 1 LO 1 m 2 U 1 LO 1 m 2 υ 1 LO m 2 U 1 LO m 2 U 1 LO r- 00 σ O d CM co G ¹ LO LO r- 00 σ o CM o O i-1 i-1 i-1 d i-i d i-1 d d CM CM CM CM | CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM d d G d d d d G d d d d d d d 1 d

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m G i —i G A Φ 4-1

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e X Z z t) o 1 Z K CM Z Z z υ CM O z z u CM O n Z u CM O , —1 Ν ' i-i u Z co ω CO u 1 m K O U o u 1 Ν ' 1 Ν ' 'ST 1 Ν ' Z s CM I Z 1 Z 1 Z 1 z l-1 o 1-1 1-1 1- ( o z z z No. u 1 u 1 1 co • d u i-1 o u 1 u 1 u 1 co 1 o 1 o 1 o O Ό 1 1 Ν ' 1 1 m CO co * <r -nT 1 co | 00 J T co CO 1 CM CM z 1 CM CM CM CM Z Z 1 p p u rd id O O O O z z rd z z z o I O O s £ Z s u u u u CN CN CN CN CN CN Λ CN CN CN CN CN CM 'Z z Z Z Z Z Z Z z Z Z Z Z Z z n z z Z z Z z z z z z Z Z z z

Table (continued)

Z (N

t) (N

I m

i (Ό

Z u

o

CM z

u

Z) z u 1 LO z z o 1 140 Z) z u 1 140 Z z u 1 LO Z z u 1 140 G m 1 140 CM Z u 1 140 z u CO 1 LO z z u 1 140 z z o 1 140 Z z u 1 LO z z u 1 140 z z u 1 140 CO Ν ' L40 CO r- 00 σ O d CN CO Ν ' 140 G CN CN CN CN CN CN CN CO co CO CO CO CO Z CM | CM CM CM CM CM CM CN CN CM CN CN CN d H d H Id Id Id d d H d d d

table (continued)

Physical properties oil S X , / 7 · —i 7 ^ U cb £ 0 r) bpob 5 5 yv? y ooooo j? p 7 7 7 7 yyyyysvy = i in to * 1 γ γ ld kO kO ii V> UUOOOO bbbbbbbškkbbbbbb OOUUOOOOOOQ _UOOOU ^{1 1} lliilllllll 1 1 1 {Ν {ΝΟ4 {Ν0 \ Ι {Ν04ίΝ {Ν {Ν <Ν {Ν {Ν (ΝΓΜ (\ Ι The hetero ring cocncocococotncocococococococococo ^ Φ ^^ ΦΦΦαΙαΙσίιτίαίπϊσίίΰαΐ CCCCCCCCCGCCCcgg 'JJ' J 'J' J zj zj -H-P -P -P -P -p -p -PP TSbbbibbbbTiTiTSTiHi-pH-p-p. _{H. d} , _H , _H , _H , _{H. H} , _H , _H , _H PPPPP ppp., - 1., - to -h., _)., _)., _) (^ Ρ ^ ΡΐίΙΐίΙΐϋίϊιΟίϋίΙΐίΙΐΟΐϋΐίΧίΙΐίΧ ^{1 1} ll 1 1 liiiliii 1 1 COCObCOPOrOrOfOfOcObCObPOCOb fbcbibibfbfbfbfb bbbbbbbbSSuuuuuu (b oh <brb {bcb {b <bcb {b bbbbbbbbUUUOOUUU y— «. CN b bbbbbbbbb ¹ bbbbbbb φφφυυυυ ^{1 1 1 1 1} ll 1 lll 1 1 1 1 llll PPPPPPPrHLnLDLDLOLOLOLOLO P b PC'JfON'LOkOr ^ OOCFlOPCNcnN'lOkO kO kO kO kO kO kO kO kO kO Γ '' * Γ * · r * - r * - r ** 0- r ^ · PPPPPrHPPr-IPPPPrHPP ¹ ...... 1 1 1 1 1 1 l | | PPPHHHMHPPPHPHHP PPPHHHHHHHHHPHPP

table (continued)

Physical properties m z Z, JT z or) z mm Z r \ Z,, U ZZ 'U m t) co 60' OO Z o Z I | , GO oo <after J? Oh 60mmm IJ? ' ^m ZcmZZoj IZZZ ⁰³ ZZZzzOZOOO ^ 'OOO'-F ΟΟΟΟΟΟΟοωω Z mmm OIIIIIIWII | OOOOO 606060606O60I606060 ui cn cn tn cn iiiiiicoiii (NCNCNC'jcMmmmmmmmi mmm ZZZZZZZZZZZZ rn zzz ooouoooooouuzooo IIIIIIIIIIIIOIII CMCMCMCMCMCMCMCMCMCMCMCMCMCMCMCMCMCMCMC The hetero ring wwmnnmnmmmww nntnw (tJ (ū (ū (ū (O (O (O (t3 (O (ū (tj (dfd (t)) ttJ -G -G * G -G 'G ΌΌ'ϋΌτίτί'Ό'ύ'ύ'ΰτίτίτίΌ'ΟΌ • G -G -G -G -G * G -G -G * G -G -G -G * G * G -G -G • G -G -G -G -G -G -G * G -G -G * G -G -G -G * G * G CLCLaCLCLCLCLCLCLftO.ft CLCl.CLCL I I I I I I I I I I I I I I I I mcncOcOcncnmcnmmcncOrocomcn V & cncnfOmfnncncnmfnmcnmcncom ZZZZZZZZZZZZ-ZZZZ οουυυυουοοοουοοο (Ώ & fncncncnnnnnmmcncncnmmcn zzzzzzzzzzzzzzzz 000000000000: 0000 C CN cnmcncnmfncnmmmcnmmmmfn zzzzzzzzzzzzzzzz oooooooooooooooo I I I I I I I I I I I I I I I I ιηιηζιηίηιηΐΏίηΐοϊΌΐηΐΌΐΌΐΌΐηίη G Z OaOOlOTGCMCOsrLnCOOOOOlOrGCM 00000000000000000000000060606 r It-And-It-It-It-It-Ir-1T-1R-1T-ItGtGtGtG 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 i HHHHHHIGIGHHHHIHHHIG hz hhhhhhhhhzhhhh

Table (continued)

G

-φ

X> 1>

G

G

G • φ

C • H

H

N

G

U

LO σ

LO

-G

G • G i — I Φ -G i — 1

G ε

-G

G ε

Εί T Εί I — I u

I

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* k 1 co co co CO CO EE EE EE 2 2 2 O O U U O U CM CM CM CM CM CM O O O O O O CO | ω ω ω Uh Uh * Sat. m ¹ CM CM CM CM CM O O O O O o z I 2 2 2 2 2 CM Λ Λ CM Λ CM □ T EE EE 2 2 υ 2 co ►t- » EE EE 2 2 Uh o 2

U

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table (continued)

CO • Φ n > 1 > (U m co • 0) c • H • r-j N • H t-l 07 07 you rd oh you rd ! -C U 07 you 1-1 O I u | l-1 u 07 you 07 υ o co u u kO kO 1 u u 1 1 1 1 1 | 1 kO o co kO kO kO kO kO 1 CM CM E i—! 1 1 1 1 1 you you you 07 you you X O 07 07 07 07 07 07 07 0 n you o o 1 you you you you you you you CM CM CM u 1 1 kO u o u u o o u O O O o kO kO 1 o o o o co co co co co co co 1 1 n 07 CM CM CM CM CM CM CM CM CM CM CM 07 k Uh you you you you you you you you you you you you you you O I O | O I U | O u u u u u u u u u u o CM CM CM CM CM CM CM CM CM CM CM CM CM CN CN 1 CN co co Ό φ CO co m co co to co CO CO co co CO co co co co Id (d (0 ra (0 Π3 d (0 efl flj td <d aJ no rd > N c c C c c C c C C c c c C c e c • d • d • d • d d • d d • d • d • d • d • d o XS XS Xf X) Xi XS X Ti X X X X X X X! M • d • d • d • d • d • d • d • d • d • d • d • d • H • d • d (D M M M R M M M M M M > q N H H t-l M j_> d • d • d -d • d • d • d • d d • d • d • d • d d • d (D CL J CL | CL j a | CL | SL L L L L L L L L L L you n n n co 00 co co co co co 00 CO CO 1 co 1 co 1 co D 07 07 07 07 07 07 07 07 07 07 07 07 et you you you you you you you you you you you you you you you you u u u u o u u u u o u u u o u u 07 m 07 07 07 07 07 07 07 07 07 07 07 07 07 07 (L you you you you you you you you you you you you you you you you u u u u u u o u υ u u υ u υ u u c 07 07 07 07 07 07 07 07 07 07 07 07 07 07 you you you you you you you you you you you you you you you you O | O O J U O U O o u o υ u υ u u υ T-1 rd <—1 i-1 T-1 I-1 r-1 d rd id td i-1 i-1 t-1 t-1 i-1 LO kO r- 00 ΟΊ o t-1 CM co sr m kO r- 00 σι o M CM CM CM CM CM Γ0 CO CO co co co co co co co T S CM | cm CN CN CN CM CN CN CM CN CM CM CM CM CM CM Id l-l M Id d H hd Id M H Id Id Id Id Id Id Id H1 M t-1 Id l-l Id Id Id Id Id Id H Id Id Id

table (continued)

to - <D X! > 1 > (U to n 0) c H • H N • H Pm co et u i-1 u CM CO o o et et CO CM CM co (J o co et et et et CM CM E et r — i u u o u O O CO X u 1 u 1 U 1 o 1 ω 1 ω 1 to 1 co 1 to 1 K O rd O LO LO LO LO LO LO LO LO LO 1 1 CO no? 1 1 1 1 1 1 1 1 1 LO LO CO et o en CO co co CO co co co co 1 1 co et u et et et et et et et et et 2 s s (d u o o O 1 o o U u u u u u U u u u Uh Uh Uh O] CM CM CM CM Λ CM CM CM CM CM CM 120 ΙΌ LO LO U) fd to to to to Ό (0 Π3 (0 (C G) m m CO CO to to to CO to CO to to G G c G • H (U (0 (U (0 tti (U (i.e. (0 (0 (0 (0 (0 • d • d • d • d > N t c G G G G G c G G G C τί τί τί τί • H • d • H H • H H H • d • H • H d • H • d 0 τί τί τί τί Ό τί τί τί τί s S g g μ • d • d • H • d Ή Ή • H H Ή H • H • d d • d 'd • d Π) s d d d d d d d d d d d d d d d Ij • d H Ή • H • H • H Ή • H • H • H • H • H • d • d • d • d 0 & f a I I et To et t et I et I et 1 et et et et et et et et K n co CO co co co co co CO co co co CM CM CM Cm] co co co co co co co co co co co co et et et et et et et et et et et et et υ u o u o o u u o u u u et et et et m co co CO CO co co co co co co co co et et et et et et et et et et et et et υ u o u u u u o υ o υ u et et et et C co CO co m co co CO co co . co co co o et et et et et et et et et et et et II u υ o u u u u o υ o o u G 1 1 1 1 1 1 1 1 1 1 1 1 · «» - * , - | rd i-1 i-1 1-1 rd I-1 rH rd 5-1 rH rd 1 1 1 1 rd CM CO V m LO r- co σι O rd CM co V ¹ 120 LO s ν ' v ¹ ν ' ν ' V V ν ' V v LO LO LO 120 120 120 120 S CM j CM | CM To CM | CM | CM CM CM CM CM CM CM CM CM CM CM H H H H M H hd M H H H Hd hd H H M H H H M H H H H H H H M H H H H

table (continued)

Physical properties E X m ^m mm m ►J S UN et -t -tm etetm ooetiųte n _E, et ™ uu et uuetbj (χιωουουωοοοου ωουυοι ι ι I 1 III 1 ^{1 1} ι ω I li <n (Ncm (N (M (N (N (ncncmi C \ 1C \ 1C \ IC \ 1C \ 1IIII |||||| (M 1 1 1 | | mmmcnmmmtOmmi jrjpj? j7j? iitetetetetet ettetetetuuuuuuuuuuet υυυυυοΟΟΟΟωωωωωυ l 1 1 1 l 1 l 1 1 1 1 1 1 1 '3''3 ^, M ^, ^ sr'Ts}'«3'sr ^ ^, srsl '^ r'3'srsr The hetero ring OC0tGW (Qū) CŪC0CQWC /) in (Z] ū} cQcfl {ύθ {ΰίΰ {ΰ {ύίΰ {ύ {θ {θπ3 {ΰ {τ3 ^ {ΰ {ΰ cccccccccccccccc; d; d ed zj -J -J -J -J -J -J -J -J -J -J -J -J -J -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h -h H -HH -H -H -H -H -H -H -H-d HH -HH -H -H -H 'd' d 'd' ^H ' ^H -h Ή ΡιΛίλΩ, ίλζΧίλο, ϋο, ϋο, ο , ϋο, α iiil I l 1 1 ll 1 l I iii lOmcsiLnLoiOmmieLnLOLomLOi-OLf) ττ feed the feed the feed 0Ί to feed a diet c CM o II £ 1> 1 1 l 1 l 1 l l l 1 l l l l R 2 Γ'ΟΟσΥΟι — ICNfO'TLO'sOr'OOOVOi — l {\ l inLDLOkOkOkOLDkOLOkOLDROROr ^ r'r- (NCNCNCMCNCNCNCNCMCNfMiCslCsIfMfMlCN ¹ I ll lIl-II-ll-II l-ll-II l-l l l l l l l l l l l l l l l l l l l l l l l l l l l i l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l i l l i l l i l l i l l i -IMI-1 HHHHHHHHHHHHHHHH

table (continued)

to m • G u - <D t) o X! > 1 > O O o to G LO i-1 1 LO (0 00 1 G Lf) 0] CO + J r-1 O) • 0) • • G + J + J H a: • H G • rH co co Payment: 0 T! 1-1 tu -G r-H 0 t) > 1 • rH > 1 r-1 ε i-1 CN O m co s m CO CO n? PC 1 E u PC Pu CN rH u ν ' X o 1 u 1 υ 1 O 1 υ 1 1 co CM CM CM CM LO 1 PC 1 1 1 1 1 co u n CO CO CO co PC 1 fe you fe Ph PC u o I U u u u o s v V v v * CM CM rH to (U T5 co tO m to (0 (U (0 (ΰ (U G G G G to to • H • H • G • rH (tj co (s) > N Ό Ό T) G (s) t-1 • H • H • rH • H • H «—1 0 o ε ε ε ε TS o N With • H • H • H • H • H N (0 (U G G G G G td G • Γ-1 • H • rH • H • H • H • d (D fe 1 fe fe fe fe -P fe E m LO Lf) tn co Lf) co 'T Pi X PC PC PC PC PC PC co Pi K PC PC PC PC PC PC c CO co CO CN (X PC PC PC o u u 1 1 1 1 lf) Lf) rH n v LO LO r- 00 O) S_l r- Γ r- r- r- * z> CM CH CH CH CM CM CM H H H H H H H M H H HI l-H HI M

table.

Structural formula:

No. R ¹ (r ² ) n R ³ R ⁴ Physical properties III-1 ch ₃ 1,5,5- (CH ₃ ) ₃ H H III-2 c ₂ h ₅ 1,5,5- (CH ₃ ) ₃ H H III-3 C ₃ H ₇ 1,5,5- (CH ₃ ) ₃ H H III-4 ch ₃ 5, 5- (CH ₃ ) 2 H H III-5 c ₂ h ₅ 5.5- (CH ₃ ) ₂ H H III-6 C ₃ H ₇ 5.5- (CH ₃ ) ₂ H H III-7 ch ₃ 5-CH ₃ H H III-8 c ₂ h ₅ 5-CH ₃ H H III-9 C ₃ H ₇ 5-CH ₃ H H III-10 ch ₃ i-ch ₃ H H III-III c ₂ h ₅ i-ch ₃ H H III-12 C ₃ H ₇ i-ch ₃ H H ΠΙ-13 ch ₃ - (n = 0) H H n _D ²⁵ · ⁰ 1.5489 n _D ²⁵ 1.5489 III-14 c ₂ h ₅ - H H III-15 C ₃ H ₇ - H H n _D ²⁵ ' ⁰ 1.5260 n _D ²⁵ 1.5260 III-16 ch ₃ -ch ₃ ch ₃ III-17 c ₂ h ₅ - ch ₃ ch ₃ III-18 C ₃ H ₇ - ch ₃ ch ₃ III-19 ch ₂ r ^x - H H n _D ²⁵ ' ⁰ 1.5810 n _D ²⁵ 1.5810

As mentioned previously, these compounds have a high herbicidal activity. They can be applied directly to the soil before germination, for treatment purposes, or sprayed on the leaves, treated as post-emergence treatment. In addition, they can be very well mixed with soil. These compounds can be applied to soil or plant foliage using 4 ha (10 acres) of 1 gram or more.

The herbicidal composition comprising the compound of the present invention as an active ingredient can be prepared by mixing suitable carriers, usually in the form of agricultural chemicals, such as water-soluble powders, water-soluble powders, emulsifiable concentrates and flowable materials. From solid carriers, talc, white soot (silica), bentonite, clay, diatomaceous earth and the like can be used. Liquid carriers include water, alcohol, benzene, xylene, kerosene, mineral oil, cyclohexane, cyclohexanone, dimethylformamide, and the like. If necessary, additional surfactants may be added to provide a homogeneous and stable derivative.

When mixed with other chemicals used in agriculture and horticulture, compatible compounds can also be used. Such chemicals may be included in, but not limited to, the classes known as fungicides, insecticides, acaricides, herbicides, and plant growth regulators. Specifically, mixing these compounds with other herbicides can reduce the dose required and the amount of labor required. In addition, greater synergistic effects of both chemicals can be expected.

It is recommended to use benzocarb, molinate, MY-93 (S- (2,2-dimethylbenzyl) 1-piperidinecarbothionate) or other carbamate-type herbicides, thiocarbamate-type herbicides, butachlor, pretilachloric acid or other admixtures in admixture with known herbicides amide-type herbicides;

chloromethoxynil, biphenox or other diphenyl ether herbicides; atrazine, cyanazine or other triazine herbicides; chlorsulfurnone, sulfometuron-methyl or other cides; MCP, MCPB or sulfonicurea type herbicides phenoxyalkanecarboxylic acid type herbicides; diclofop-methyl or other phenoxypropionic acid type herbicides; benzoylprop-ethyl, flamprop-ethyl or other benzoylamino herbicides and others such as dimron, benzathone, difenzoquart, 4-ethoxymethoxybenzo-2 ', 3'propiomnes piperophos, naproanilide, HW-52 dichloroanilide, 1- (3- ( methylphenyl) -5-phenyl-1 H -1,2,4-triazole-3-carboxamide), dichloro-8-quinolinecarboxylic setoxidine, alloxydim sodium sandionic herbicides. These quinchlorac (3.7 acid) and other herbicides can also be combined in oil or in an oil concentrate.

with the addition of cyclohexa various vegetable

The concentration of the active component in the herbicidal compound may vary depending on its composition. For example, in a moisture absorbing powder, this concentration may be from 5 to 70 percent by weight, but preferably from 10 to 30 percent. It may be present in the emulsion concentrate in an amount of from 3 to 70 percent, but preferably from 5 to 20 percent. The granules may have a concentration of 0.01 to 30 percent by weight, but preferably 0.05 to 10 percent by weight.

The moisture-absorbing or emulsifying concentrates thus obtained can be diluted with water to the desired concentration. For the treatment of soil or plant foliage they may be used in the form of a liquid suspension or emulsion. In addition, the pellets can be spread directly in water or mixed with soil.

The following are non-limiting examples of herbicide composition.

Example 3. Moisture-absorbing powder parts by weight

The compound of the present invention in its composition 20 White soot 20 Diatomaceous earth 52 Sodium alkyl sulfate 8

These materials are thoroughly mixed to fine particles. A moisture-absorbing powder containing 20% of the active ingredient is obtained. When used, the powder is diluted with water to the desired concentration and sprayed as a suspension.

Example 4. Emulsion concentrate parts by weight

In its composition, the compound of the present invention 20 Xylene 55 Dimethylformamide 15 Polyoxyethylene phenol ether 10

These substances are thoroughly mixed and dissolved to form an emulsion concentrate containing 20% of the active ingredient. For use, it is diluted with water to the desired concentration and sprayed as an emulsion.

Example 5. Pellet parts by weight

In its composition, the compound of the present invention 5

Talc 40

Clay

Bentonite Sodium alkyl sulphate

10 7

Thorough mixing of all these materials gives pellets containing 5% active ingredient.

The herbicidal activity of the following compounds can be illustrated by the following tests:

Test 1. Post-emergence treatment test

The seeds of Henry's glove, the foxglove, the galen, the vetch, the amaranth and the corn were planted in pots (200 cm ² ) filled with loam soil and grown in a greenhouse. When the plants reached a height of 5-10 cm, an aqueous suspension was sprayed on their leaves, prepared by diluting the forming emulsion concentrate with water to the indicated concentration (250 ounces). The dose size is 100 liters / 4ha (10 acres).

Three weeks after spraying, observations were made for damage to each plant species. the rating was made on a scale from 0 to 10, which has the following values:

Scores Degree of impairment 0 0% 2 20-29% 4 40-40% 5 60-69% 3 80-89% : o 100%

Scores of 1, 3, 5, 7, 9 grade an intermediate grade ranging from 0 to 2.2, 4.4, 6.6, 8.8 and.

(plant weight non- - (plant weight in cultivated area) rotcme area) xl00

Degree of damage (%) = ---------------------------------- Plant weight in the untreated area

The results obtained are shown in Table 4.

table

The compound No. Degree of impairment (points) Henry fingertip Wow- shit Fibrous galenium Burno- tis The bride vixen Corn zai 1-10 10th 10th 10th 10th 10th 3 1-20 10th 10th 10th 10th 10th 0 1-21 10th 10th 10th 10th 10th 0 1-35 10th 10th 10th 10th 10th 0 1-36 10th 10th 10th 10th 10th 0 1-48 10th 10th 10th 10th 10th 1 1-49 10th 10th 10th 10th . 10th 0 1-50 10th 10th 10th 10th ^10th 0 1-54 10th 10th 10th 10th : 10 0 1-55 10th 10th 10th 10th . io 1 1-56 10th 10th 10th 10th 10th 0 1-57 10th 10th 10th 10th ^10th 0 1-65 10th 10th 10th 10th 10th 1 1-81 10th 10th 10th 10th 10th 0 1-85 10th 10th 10th 10th 10th 1

table (continued)

The compound No. Degree of impairment (points) Henry fingertip Cooler- shit Fibrous galenium Burno- tis The bride vixen Corn zai 1-97 10th 10th 10th 10th 10th 2 1-98 10th 10th 10th 10th 10th 2 1-99 10th 10th 10th 10th 10th 0 1-100 10th 10th 10th 10th 10th 0 1-101 10th 10th 10th 10th 10th 3 1-109 10th 10th 10th 10th 10th 0 1-133 10th 10th 10th 10th 10th 0 1-143 10th 10th 10th 10th 10th 0 1-144 10th 10th 10th 10th 10th 1 1-145 10th 10th 10th 10th 10th 0 1-146 10th 10th 10th 10th 10th 0 1-168 10th 10th 10th 10th 10th 0 1-169 10th 10th 10th 10th 10th 0 1-170 10th 10th 10th 10th 10th 2 1-172 10th 10th 10th 10th 10th 0 1-173 10th 10th 10th 10th 10th 2 1-176 10th 10th 10th 10th 10th 0 1-177 10th 10th 10th 10th 10th 0 1-178 10th 10th 10th 10th 10th 0 1-179 10th 10th 10th 10th 10th 3 1-180 10th 10th 10th 10th 10th 2 1-181 10th 10th 10th 10th 10th 3 1-183 10th 10th 10th 10th 10th 3 1-184 10th 10th 10th 10th 10th 3

table (continued)

The compound No. Degree of impairment (points) Henry fingertip Esh- shit Fibrous galenium Burno- tis The bride vixen Corn zai 1-185 10th 10th 10th 10th 10th 0 1-186 10th 10th 10th 10th 10th 0 1-187 10th 10th 10th 10th 10th 2 1-188 10th 10th 10th 10th 10th 3 1-189 10th 10th 10th 10th 10th 0 1-190 10th 10th 10th 10th 10th 2 1-191 10th 10th 10th 10th 10th 0 1-192 10th 10th 10th 10th 10th 0 1-193 10th 10th 10th 10th 10th 0 1-195 10th 10th 10th 10th 10th 0 1-196 10th 10th 10th 10th 10th 0 1-197 10th 10th 10th 10th 10th 3 1-198 10th 10th 10th 10th . 10th 0 1-200 10th 10th 10th 10th 10th 0 1-201 10th 10th 10th 10th 10th 0 1-202 10th 10th 10th 10th ^10th 0 1-203 10th 10th 10th 10th 10th 0 1-204 10th 10th 10th 10th 10th 1 1-205 10th 10th 10th 10th 10th 1 1-207 10th 10th 10th 10th 10th 2 1-208 10th 10th 10th 10th 10th 0 1-209 10th 10th 10th 10th 10th 0 1-210 10th 10th 10th 10th 10th 2 1-211 10th 10th 10th 10th 10th 0

table (continued)

The compound No. Degree of impairment (points) Henry fingertip Wow- shit Fibrous galenium Burno- tis The bride vixen Corn zai 1-212 10th 10th 10th 10th 10th 2 1-214 10th 10th 10th 10th 10th 0 1-215 10th 10th 10th 10th 10th 3 1-216 10th 10th 10th 10th 10th 0 1-217 10th 10th 10th 10th 10th 0 1-218 10th 10th 10th 10th 10th 0 1-219 10th 10th 10th 10th 10th 0 1-220 10th 10th 10th 10th 10th 0 1-222 10th 10th 10th 10th 10th 0 1-224 10th 10th 10th 10th 10th 3 1-225 10th 10th 10th 10th 10th 3 1-228 10th 10th 10th 10th 10th 0 1-229 10th 10th 10th 10th 10th 0 1-230 10th 10th 10th 10th 10th 0 1-231 10th 10th 10th 10th 10th 0 1-232 10th 10th 10th 10th 10th 0 1-233 10th 10th 10th 10th 10th 0 1-234 10th 10th 10th 10th 10th 0 1-237 10th 10th 10th 10th 10th 3 1-238 10th 10th 10th 10th 10th 0 1-240 10th 10th 10th 10th 10th 0 1-241 10th 10th 10th 10th 10th 0 1-244 10th 10th 10th 10th 10th 2 1-245 10th 10th 10th 10th 10th 2

table (continued)

The compound No. Degree of impairment (points) Henry fingertip Esh- shit Fibrous galenium Burno- tis The bride vixen Corn zai 1-249 10th 10th 10th 10th 10th 3 1-250 10th 10th 10th 10th 10th 0 1-251 10th 10th 10th 10th 10th 0 1-254 10th 10th 10th 10th 10th 0 11-102 10th 10th 10th 10th 10th 3 11-109 10th 10th 10th 10th 10th 0 11-130 10th 10th 10th 10th 10th 0 11-137 10th 10th 10th 10th 10th 0 11-277 10th 10th 10th 10th 10th 3 Reference compound A 6th 7th 8th 4 5 7th Reference compound B 6th 5 8th 2 8th 6th

Reference compound A:

(DE 3902818)

Reference compound B:

(DE 3902818) * 0

Claims (3)

DEFINITION OF INVENTION .T ' A substituted bicycloheptadione derivative of formula (I) wherein R 'represents a lower alkyl group, a phenyl group which may be substituted, an arylalkyl group which may be substituted or a heterocyclic group which may be substituted; R, the same or different, represents a halogen, an alkoxyl group, an alkylthiol group, an alkylsulfonyl group, an alkyl group, an alkoxyalkyl group or an alkoxycarbonyl group, and n is from 0 to 4; R ^J and R ⁴ , the same or different, represent hydrogen or a lower alkyl group or a salt thereof. 2. A process for the preparation of a compound of formula (I) (I) wherein R @ 1, R @ ² , R @ ³ , R @ ⁴ and n have the meanings as defined above, in which they undergo a ring closure reaction in the compound. , having a composition according to formula (II) (ii): wherein R 1, R 7, R + and n have the above meanings and Q is a leaving group in the presence of a base. 3. A herbicide comprising one or more compounds represented by the general formula (I) in which R ^x , R, R ', R ¹ and n have the meanings indicated above for the function of the active components.